2 comments/ 167883 views/ 46 favorites Teaching My Wife Ch. 01 By: jdrew2001 After nearly 25 years of marriage our sex life had become more and more conservative and predictable. Somewhere along the way the woman who indulged many of my fantasies and kinks had grown more and more plain vanilla in her sexual preferences. I fondly recall in years past suggesting that we fill a condom with water and freeze it and watching her go upstairs, return with a condom, fill it with water from the kitchen sink, tie the end to prevent leaks and put it into the freezer. I remember watching her fill the condom with a fair amount of water and telling her that water expanded when it froze and her telling me that she knew that and seeing the twinkle in her eyes that let me know she was looking forward to feeling the icy dildo inside of her pussy. Watching her fuck herself to orgasm with the frozen condom was always a turn on as was fucking her after while the walls of her pussy were still chilled from the icy dildo. I remember sending her out to the sporting goods store to buy a ping pong paddle to use on her lovely ass and later sending her to the adult store to buy a whip. She returned with a black leather flogger that we still have to this day. I used to tell her to go to the bedroom, get the flogger and the ropes and to strip naked. I would then tie her feet to the foot board. I would also take a belt and cinch it around her slender waist and then take two ropes, run them under the belt and tie her to the footboard so she could not scoot her ass away from the edge of the bed. Finally, I would tie rope around each knee and tie the ends to the posts on either side of the bed spreading her wide open. For a finishing touch I would jam a pillow under her ass which had the effect of lifting her pussy higher and make it even more exposed. Once she was secured in place I would get a deck of cards. I would ask her for a number from one to 54 (two jokers) and I would draw six cards starting with the number she gave me. The numbers on the cards would indicate how many strokes she would get with the flogger with one card for each breast, one for each inner thigh and two for her pussy. Black cards were for harder blows and red were for medium. If a joker came up I would pick another card and the card would be doubled. I would then blindfold her and the flogging would begin. First one breast to the number on the card, then the other, next the inner thighs and finally her pussy. If I was feeling particularly diabolical, I would first finger her pussy to get her even wetter and then spread her pussy lips open before administering the strokes to her pussy. The flogging itself was actually pretty tame and definitely not hard enough to break the skin or to raise welts that lasted any length of time, just enough to get her to jump and grunt from each blow. Sometimes while we were doing this she started to get really turned on and I would keep flogging her pussy and tell her I would stop once she had an orgasm. I would tell her that if she wanted to reach orgasm from the strokes of the flogger that she had to ask for more strokes. Hearing her say "please" and "again" over and over again as I flogged her pussy is a memory that gets me hard to this day. If she did not come from the flogging I would finish her off with one of our sex toys or my mouth or cock. We did the flogging scene for several years before she decided she was not into that anymore and we stopped. We also stopped doing other kinky things that we enjoyed as somewhere along the way the sexually adventurous woman who was my wife became less and less daring as far as our sexual activities and this story is about how I went about changing that. Before getting into the story I should describe my wife. Her name is Ann and she is 5'2" tall and weighs 115 pounds. She has brown hair and eyes. Her breasts are a natural B cup and she has a very, very thin waist which gives her a very curvy hourglass figure and an ass to die for. Although I had talked her into shaving her pussy a couple of times in the past she has in recent years kept a full bush. We never had children so her pussy is still nice and tight. As I said, somehow over the years our sex life became more and more routine. We had sex maybe once a week usually on Sunday morning in our bed and although I still used some toys on her and we pleasured each other orally (although Ann rarely swallowed), the kinky, out there aspect was gone. It was as much my fault as it was hers and the tipping point was my developing a medical condition that caused high blood pressure leading to ED that fortunately reversed once the condition was treated and my blood pressure returned to normal. This episode made me realize that I had a limited number of years of serious fucking left and that I better use it before I really did lose it. I started to try to have sex with Ann more often but she resisted and we would sometimes argue about how often we had sex and what we did to each other when we "played" as we called it. I finally got fed up and told her that either she satisfy me by going back to the woman she once was or that I would find someone else who would and that maybe that would lead to more than just a sexual relationship. I told her that I wanted her to go back to the time when she told me that she wanted to be a lady outside the bedroom but a whore in the bedroom. I told her that she needed serious whore training to regain her former mojo and she eventually agreed. When she agreed to the training, Ann thought that I was going to do the training but I told her to remember the disasters we had when I tried to teach her to ski and to play golf. Maybe it is just us but it always seems difficult for a spouse to teach the other how to do something. For us, it is just causes one argument after another. My showing Ann how to swing a golf club just never seemed as effective as when a golf instructor told or showed her the same thing. In addition, I knew that I would be more susceptible to her pleas to stop or slow down than would a stranger thus keeping the boundaries of our sexual activities largely where they were. I could see the wheels turning as Ann realized that her training would be at the hands of other men and the look of horror that came across her face. Ann tried to bargain with me, telling me that she already knew how to be a whore in the bedroom but I would not have any of it. When she saw that she would not change my mind she started to cry but I told her that either she would be trained by other men or our relationship would likely be in trouble. Ann ran up to the master bathroom and closed the door. I could hear her crying softly but the next morning she woke me with her lips on my cock and told me that she would do whatever it took to insure that we would stay together. Ann works for a business consulting company and has to travel about once every four to six weeks to various locations in the US for a couple of days on each trip. I decided that having her training occur during these trips would be the best because the men involved would likely never see her again and she could protect her anonymity. Ann was relieved when I told her this part of the plan although she failed to realize that if the men she choose did not know her beforehand and understood it was a one time deal they would likely just fuck her brains out and otherwise use her more harshly than I would. Ann was about to find out the difference between having someone make love to her and fucking her. Ann had a trip to Atlanta coming up in about two weeks so I got busy putting things in place. I bought a compact video camera and a small tripod. The camera had pretty good low light capability although I told Ann that whenever possible she should leave lots of lights on in her room. Besides the camera Ann would take various sex toys with her depending upon the scenes she was to enact with her trainer. This meant that Ann would have to check at least one piece of luggage unless she wanted to run the risk of having to answer a lot of embarrassing questions at airport security. I would also give Ann a letter outlining what her "trainer" was to do to her and she was to give this letter to the guy she picked. Normally, Ann would come back from her business trips on Friday afternoon or evening but to allow time for her training we decided that she would stay over on Friday night and come back late Saturday instead. We would have to pay for the extra night but it would be a small price to pay. Ann would tell her company that she was staying on to visit with some old friends who had recently moved to Atlanta and just deduct the Friday night hotel and expenses from her reimbursement request. A few days before she was to leave, I asked Ann to get her clothes ready for the trip and when she was ready I would review what she had selected. She picked out her usual conservative selection of business wear and I went through it and took out all of the panties she had selected. I let her keep the bras as she did not want to have her nipples pointing out at clients and colleagues so as to diminish her professional demeanor. I added a pair of CFM heels, a garter belt and stockings as well as a Victoria's Secret push up bra and a short skirt with a slit up the side. I told Ann that she was to dress up in garter and hose, CFM heels, the push up bra, slinky top and short skirt and find a guy on Friday night, flirt with him enough to let him know that she was up for a wild time and once she was sure he was interested to tell him the story of how we wanted her trained sexually by strangers and tell him about the letter. If he continued to be interested she was to give him the letter and ask him if he was willing to do to her what the letter said. I let Ann read the letter before she left so she knew upfront exactly what would be happening to her if she picked up a guy and took him back to her room. Besides having the guy do the things in the letter to her Ann also understood that all three of her holes were to be available to the guy and that she was to do her best to please him. The only conditions were that she had to video the encounter and he had to use a condom when he was in her pussy or ass. The letter I gave her read as follows: "If Ann has given you this letter then things have progressed pretty far and she wants you to use her and fuck her. Ann is my wife and she has agreed that she needs to be trained to be more of a slut in the bedroom. She is yours for the night and tomorrow morning provided that you allow her to video your session and use a condom when you are in her pussy or ass. Other than that she is yours to do with as you see fit. Ann does not like to swallow cum nor does she like cum on her face. She has agreed to try to learn to do both so you should definitely cum in her mouth and on her face. I included a toy kit in Ann's luggage. In the kit is a bandana you can use as a gag, a flogger, a tube of lube, a deck of cards and assorted lengths of rope. I used to tie Ann with her legs open and flog her tits, pussy and inner thighs. When I say "flog" I mean hard enough to get a yelp out of her but not hard enough to break the skin or raise welts that last more than a few minutes. Once you get started you should get the hang of how hard she can take it without being damaged. After you get done with the warm-up flogs ask Ann to pick a card from the deck and take it and the next six cards. The numbers on the first four cards will tell you how many strokes Ann is to get on each breast and each upper, inner thigh and the last two cards will be the number for her pussy. If a joker comes up pick another card and double the card(s). For the flogging, you should tie Ann up so that her breasts, inner thighs and pussy are exposed and open to the flogger. The object is to position Ann so that her pussy is facing up as though she had drawn her knees up to he chest. Then you can bring the flogger down on it. Putting a pillow under her ass will also sometimes make her pussy an easier target. You can leave her hands free as she used to know enough to keep them out of the way. Take your time in tying Ann up as I used to do this along with fingering her pussy a bit and/or playing with her nipples. I would also make comments about how it would feel when the flogger came down on her more intimate parts. Ann would quiver and sometimes even moan as her mind anticipated what her body would soon feel. Ann would sometimes come just from having her pussy flogged and you should watch her reactions to see if this is the case when you flog her. Her pussy getting wetter is usually a good sign that she may be up to coming from the flogging. If she is getting wetter and wetter ask her if she wants to come from the flogging and if she says "yes" make her ask for the additional strokes and then gag her and flog her enough to make her cum. If she does not come from the flogging then give her an orgasm by fucking her (condom required) before untying her. You will be amazed how kinky is to have your skin against hers and feel how warm her skin is in spots from the flogging. I also included a tube of lube as Ann used to let me fuck her in the ass but that has been off limits for a while now but if you are into anal then fuck her ass. We also used to play with a condom filled with water that had been frozen. Ann used to fuck herself with it and then I would fuck her. I know you cannot do exactly that but you should have her slip on a little something revealing and go to the ice machine. When she gets back you can fill her ass and pussy with ice cubes or you can have her do it. She will carry on and try to talk you out of it but do not take "no" for an answer and as the ice takes effect you can finger her to an orgasm and then fuck her refrigerated pussy and/or asshole. Ann would come like gangbusters from the fucking I would give her after we chilled her pussy even though she said the walls of her pussy did not feel my thrusts as much as they did when they were at a normal temperature. Ann used to be very hot in bed and I hope training sessions like these get her back to that state. She is your slut for tonight so make good use of her. When Ann gets hot she likes the side of her neck (below her ear) licked and kissed. If she really is getting into it you can lick her ear also. Remember, Ann has selected you and she is your fuck toy for this evening. You are not making love to her, you are fucking her. Do not do anything to permanently damage her but otherwise use her for your pleasure." The guy Ann was sitting with at the bar to whom she had given the letter took a deep breath and asked for the check. He asked her if she was sure and whether she had read the letter. Ann said that she had read the letter and knew what would happen to her if she took him back to her room. They discussed the letter a bit more and Ann answered some questions the guy had about how we used to do the things listed in the letter and finally they walked out of the bar and took the elevator up to her room. From the video I could see that the guy she picked, Lou, was about 6 feet tall with a stocky build and around 200 pounds. He looked to be Italian and had black hair and a moustache. He seemed confident but not arrogant which was good as Ann would soon be tied with all of her charms open to him as he wielded the flogger and otherwise used her. Ann and I had talked about the risks in letting a stranger do these kinds of things to her but Ann finally decided that there was no more risk than there would be if she had just picked up a guy for casual sex on one of her trips. As we talked about it Ann pointed out that most guys in this kind of a situation would be happy with just regular sex. Here the guy would be able to fuck her pussy, ass and mouth as well as do some more kinky things with and to her. Ann reasoned that they guy would be so happy with having access to all three of her holes and doing the kinky stuff in the letter that he would be unlikely to do other things that could harm her. She had me almost convinced and vetoed any suggestions I made that we put other less aggressive activities on the menu for the first session. Ann also reasoned that the flogging would be among the most intense things she experienced and if she got it out of the way she would be more likely to accept further training sessions in the future. The next few hours were an experience for Ann and Lou gave her a real workout. Ann turned on the video camera and Lou started off by nodding at Ann and saying "Show me what you got honey". Ann then slowly took off her skirt and top and put them aside. He told her to leave the garter belt, hose and heels on. He then had her undress him and that was when she first saw that his cock was larger than she had experienced before. Lou's cock turned out to be nearly nine inches and very thick when fully erect. Lou got Ann on her knees in front of him and he said "start sucking baby, your husband wants me to teach you to swallow cum". Ann went to work and tried mightily to take his full cock into her throat but it was just too big for her even though she has been able to deep throat my standard size cock for years. When he was about to come he took her head in his hands and held her tight. Ann told me that he fired six or seven good shots of cum into her mouth and then held her in place until she swallowed. She said swallowing was not as bad as she feared and thought that maybe that was due to the fact that she was with a stranger who may not let her spit out his cum as I do. I was happy to see that she was beginning to understand the difference between making love and fucking. He let her rest and clean up and then sent her out to get some ice. When she returned he had her strip again and then told her to start putting ice cubes into her ass and pussy. Ann got three cubes into her ass and four into her pussy when she begged him to let her stop. Lou told her that she had to get a dozen cubes inside of her and what hole was her choice. She cried and whimpered but kept trying and eventually got six cubes into her pussy and five into her ass. He told her she could use the twelfth cube on her nipples and she rubbed it over them until they hardened into little points. He made her keep the ice inside until it melted and then he fucked her pussy while it was still chilled from the ice. Ann said that she came like crazy even though her pussy felt like it was frozen and she could barely feel his thick cock against the walls of her cunt. After this they slept for a while and woke up about four in the morning. Lou said "OK, honey, first I cooled you off and now it is time to warm you up." Ann knew that this meant that her flogging was at hand. Lou then tied Ann spread open on the bed as described in the letter, had Ann pick out the six cards from the deck and flogged her tits, thighs and pussy until he saw that she was getting wet. He asked her if she wanted him to continue flogging her pussy until she came and she said that she did. He said that although he would enjoy hearing her beg for more strokes he was going to gag her so she would not disturb the other guests. He forced the gag between her lips and tied it behind her head which was a new experience as I had never gagged Ann before. He then stepped back and zeroed in on her wet pussy. Blow after blow landed on her exposed, defenseless, open pussy and it seemed to go on forever. Ann would make a sound or a grunt whenever the flogger hit her pussy. Every ten strokes or so Lou would stop and finger her pussy and Ann would moan and try to hump his fingers deeper into her. Ann must have been enjoying herself because she never made a move with her hands to protect her pussy although she later told me that she did not move her hands to intervene in her pussy's punishment because she did not want Lou to tie her hands as she wanted to feel at least a little bit in control. Teaching My Wife Ch. 01 Eventually Ann started to rotate her ass around the bed as much as she was able being tied like she was. She also tried to raise her hips up as if to offer her pussy up for more punishment. She was no longer making the grunting sounds whenever a blow landed but was now moaning almost continually. She was right on the edge and Lou saw this and told her he was going to give her five hard strokes and that she should come before he was done. Ann made it to the third stroke when she exploded in an orgasm so strong she almost pulled her out of her ropes. Before Ann could come down from her orgasm Lou had a condom on and was buried up to his balls in her cunt. He fucked her hard and fast and Ann had another big orgasm followed by a series of smaller tremors. Surprisingly despite the kinky stuff he had just done Lou lasted for a while and Ann said that she had never come for such a long period of time as one orgasm would melt into the next. They fell asleep until the next morning and Lou told Ann he wanted to fuck her ass. She got the tube of lube and forced some of it into her ass followed by one, two and then three fingers. Ann later told me that she wanted to lube and otherwise get herself ready because she knew it would be a struggle to accept Lou's thick cock in her ass. Ann was not sure about having such a big cock up in her ass but before she could think too long Lou bent her over a chair, slipped on a condom, lined up with her asshole and pushed himself through her sphincter with one strong thrust. Ann said she saw stars and started to scream and Lou clamped his hand over her mouth to muffle her screams. He told her to relax and to get used to the fullness. He held her for a while and eventually she calmed down as her ass grew accustomed to the cock that was splitting her wide open. Of course, the fingers he used to play with her clit also helped Ann to relax. When he sensed that she was able to better accommodate him he started to fuck her ass with long hard strokes. Ann was getting the ass fuck of her life and I could see on the video how her knuckles were white from her holding on tightly to the chair she was draped over. Fortunately or unfortunately, Ann hasn't told me which, Lou was able to last a long time because Ann had made him come a couple of times in the past few hours. When he finally exploded in her ass Ann said that she could feel every shot even through the condom and still remembers the "pop" sound she heard when he finally pulled out of her ass. Ann got close but did not come from her anal fucking because she was pretty tired after the many orgasms she had already had with Lou. She said that they then kissed farewell and Lou left. Ann said that it took more than an hour after Lou left for her ass to fully close up and she spent most of that time sitting around and idly fingering herself. I was already seeing the signs of the changes in her that I had hoped to see. Ann then packed her stuff, went to the airport and flew home. When she arrived I greeted her warmly, made her a drink of her favorite adult beverage, popped the video she took into the CD player and told her to tell me about her experience. Overall she was OK with had happened to her saying the fear she had of what an unknown stranger might do to her was actually a powerful turn on once Lou started to put her through her paces. She said that she would be willing to do it again if I wanted and I said that I definitely wanted. In the weeks following her trip I was able to fuck Ann's ass a couple of times. She even swallowed my cum on two occasions. One day when I came home from work Ann greeted me naked in the bedroom with the ropes and flogger beside her on the bed. She is still far from where she was earlier in our marriage but I believe that in time my bedroom whore will be again at my side. Teaching My Wife Ch. 02 For a full background readers should review Part 1 before reading this chapter. Basically, this is the story of how my wife Ann, who used to be sexually adventurous, became more and more conservative and how I set out to change things back to and beyond the way they were. Besides the activities described in Part 1, Ann in the past had allowed me to use a wide variety of vibrators and dildos on her. A favorite of mine was to insert a fairly large inflatable vibrating butt plug into her ass and an inflatable dildo into her pussy. I would turn the butt plug on low and Ann would be on her way. In a few minutes I would pump the bulb on the butt plug a few times and give the dildo a few pumps as well. As the toys inflated inside of her, Ann would tremble and let out a very sexy moan. She would writhe on our bed and push up her pelvis as though trying to fuck an imaginary lover instead of just the toys inside of her. After a few more minutes I would man the pumps again and turn up the speed of the vibrator in Ann's ass. If I got it right and did not push Ann beyond what she could comfortably take she would continue to moan and slide her ass from side to side and move her pelvis up and down. If I went too far she would open her eyes, even though her eyes appeared to have rolled back in her head, and put her hand over the hand in which I was still holding the offending inflation bulb. That was her signal for no more, right now and she would keep her hand on mine until she got comfortable with, or at least accepting of, the larger size of the sex toys inside her. It was at this point that I would usually straddle Ann's chest so that my cock was at her lips. She would take me in her mouth and suck for all she was worth. Whenever I further inflated either of the toys while she was sucking me I could immediately feel the effect in how she used her tongue and how she sucked. It was at times like these that I particularly wished that Ann would swallow because my coming in her mouth would have been a terrific climax to her triple penetration. I never let myself come because I knew that would cause a break in the action as Ann cleaned up and I did not want to interfere with Ann's progress towards an orgasm. Sometimes if I inflated the toys too much Ann would say, "That's too big," or, "That's too much," and I would let some air out slowly until she said, "OK, that's good." After giving her a few minutes, I would start to inflate the toys further. Often Ann would hit the wall a second time and I would have to again release some air. Whenever this happened I would take the inflation bulbs and put them into her hands and tell her to do it. There was something very sexy about seeing Ann lying on her back with her legs drawn up and spread with the hoses from the toys coming up from between her legs to the inflation bulbs that she was now holding in her hands. Her labored breathing and the muffled sound of the vibrator in her ass added to the erotic aura. Once Ann had control of the bulbs I would tell her, "This one needs to go up" and touch the hand in which she was holding the bulb for the toy that I had just partially deflated. Ann would tense with each pump of the bulb and when she was done I would touch her other hand and say, "OK, now this one." I would let her get used to the new sizes and then touch one of her hands again and say, "More." I don't know if it was because Ann felt better being in control of the inflation process or if she got off on doing things to herself but she often took the toys further than she would let me go. As I increased the speed of the vibrator in her ass to its maximum and the size of the toys inside of her continued to increase Ann would get close and closer to orgasm. She would literally be panting and moaning deeply and as she got closer would rub her hands through her bush just above her clit. That area has always been one of her erogenous zones so when she starts to go there an orgasm is not far away. She would sort of keep her hands on the inflation bulbs while taking a few fingers off of each to run through her bush. She would also start to rub her thighs together tightly. I would either be watching or touching her breasts or sucking on her nipples. Most of the time I would let her get to orgasm without more but on a few occasions I would place my hand over hers and give the bulb for the dildo in her pussy a squeeze or two. This would always send her over the edge into a screaming, writhing orgasm. For those of you wondering if I had an ulterior motive besides enjoying theses scenes the answer is, "Yes." I hoped that these scenes would get Ann receptive to the idea of a twosome or threesome but she never went that far. We also would on occasion play where Ann would have a vibrator in her ass or pussy and she would suck me off. Once after we were done using the inflatable toys I deflated then and took them out of Ann's pussy and ass. I then closed the valves and started to pump them up and asked Ann if she wanted to see how big they got. She said that she did not need to see as she felt how big they were when they were inside of her but she did get an amazed look on her face when I was done inflating the toys. When inflated to the size it was when inside of her the butt plug had to be the size of a navel orange/small grapefruit and the dildo in her pussy was the size of a large cucumber. Another toy that we played with on one occasion was a huge vibrator that I purchased on the internet. It was supposedly modeled after the cock of a major porn star whose name escapes me. It was pink and was made of the latex type of material that is supposed to feel like human skin. I took it out of the box and washed it and showed it to Ann. She gulped and her eyes got wide. "I can't take something that big up inside of me," Ann said. I told her to touch it and when she felt it she said that she could not believe how much it felt like real skin. The thing was huge, at least ten inches and very thick and she felt it and the fake balls at the bottom for a few minutes. I think she knew I would try to get it inside of her and was trying to delay the inevitable or at least get more warmed up by playing with her soon to be intimate friend. Anyway, after a lot of preparation and lube it did go in Ann's pussy to about seven inches. The whole time it was in her Ann's eyes were wide open as though she were shocked that she had something that big inside of her. When I tried to fuck her with it she stopped me saying that when I pulled it out it felt like her whole insides were being pulled out with it. I slowly pushed it back in and turned the speed up to the maximum. Ann lasted only about a minute before having one of the most intense orgasms I ever saw her have. Unfortunately that was one and done with that toy and I was never able to get Ann to let me use it on her again. She would say that it was too big and I would counter that she had already taken it once but it was her pussy so she won. As I described in Part 1, over the years Ann had become more and more conservative and plain vanilla as far as sex went. The adventurous woman I described above had left the building. Vibrators, if we used them at all, were smallish and used mostly on her clit. We began to argue more and more about sex and I eventually told Ann that if she were not willing to be a whore in the bedroom I would find someone who would. Being a whore in the bedroom are her words as she told me shortly after we were married that she wanted to be a lady outside of the bedroom but a whore in the bedroom. I told Ann that she needed to be taught how to once again be a whore in the bedroom but that because she had over the years pulled back the sexual boundaries we once had that these lessons would be from other men. I knew that if we tried to become more adventurous and Ann objected to something that I was doing to her that I would slow down or stop because I loved her while a stranger would likely say, "Come on, baby, you can take it" and keep going. Ann would not be as free with a stranger to impose her boundaries. Because Ann travelled out of town on business about every six weeks we decided that her lessons would be during these trips. Most of her trips started early in the week and she would be home late Friday afternoon or evening. I told her that I would pack a kit of the items to be used for each lesson along with a video camera and an instruction letter she was to give the man she selected. For this trip, I told Ann that she was not to read the letter or open the kit unless the man she selected allowed her to do so. So as not to interfere with her job, Ann would extend her trip for an additional night at our expense and tell her company that an old college friend, etc. lived in the town she was visiting. The additional night would be lesson night. About a month after her first lesson trip Ann came home and told me that she had to go to Chicago in about two weeks. I told her I would get her travel kit and the letter ready. Ann knew from her experiences on her first trip that her lesson would be based on things we used to do in the past with a few extra kinks thrown in. As on her first trip, I told Ann that she was to find a guy on Friday night and flirt with him for a while making it clear that he could have he if he wanted her. She was to fix her hair and makeup, dress up in garter and hose, CFM heels, top and short skirt and when she had picked the guy, tell him about how she wanted whore lessons and give him the letter, let him read it and ask him if he was willing to do what the letter said. If he agreed, she was to do whatever he wanted for the rest of the night and into the middle of the next day except that she had to video the encounter and he had to use a condom whenever he was in her pussy or ass. The letter I gave her read as follows: "If Ann has given you this letter then things have progressed pretty far and she wants you to use her and fuck her. Ann is my wife and she has agreed that she needs to be trained to be more of a whore in the bedroom. She is yours for the night provided that you allow her to video your session and use a condom when you are in her pussy or ass. Other than that she is yours to do with as you see fit but you must at least do the things listed in this letter to her. Ann does not like to swallow cum nor does she like cum on her face. During the course of things you must come in her mouth and make her swallow. If you come on her face leave it there for a while and then make her scoop it up with her fingers and lick her fingers clean. There is a toy kit in Ann's luggage. In the kit is a tube of sex lube, condoms, an inflatable butt plug, an inflatable dildo, a large vibrator, a ball gag, handcuffs and assorted lengths of rope. When we did the things you are going to do with Ann she did not need to be restrained but as I want you to push her limits further than she let me the restraints are there if you need them. Because I love Ann I was reluctant to push her limits and would usually back off when she wanted to stop or slow down. You, on the other hand, have no emotional attachment to Ann and hopefully all she is to you is an attractive woman with whom you are going to engage in hot kinky sex. During the course of the night, Ann may object to certain things you are doing and she will carry on and try to talk you out of it but do not take "no" for an answer. Ann understands that she cannot say "no" except for violations of the video and condom rules or to any activity that would permanently hurt or mark her. Ann used to be very hot in bed and I hope her training gets her back to that state. She is your slut for tonight so make good use of her. When Ann gets hot she likes the side of her neck (below her ear) licked and kissed. If she really is getting into it you can lick her ear also. Another of her erogenous zones is the pussy hair above her clit. When Ann gets close to cumming she will run her fingers through that part of her bush and she gets off on having that done to her. OK, now for the things you are to do to Ann: 1) Lube up the butt plug and insert it into Ann's ass. Next, lube up the inflatable dildo and put it into Ann's pussy. Turn the vibrator in the butt plug to a low setting and close the valves on the inflation bulbs. Give each bulb three pumps to get things started and then let Ann get used to the size. Continue pumping and slowly increase the speed of the vibrator. Around five pumps Ann will start to whine and complain but keep on going but give her some breaks and/or let some air out as needed. The most she ever took when we did this was seven pumps in her ass and seven in her pussy. I want you to get her to ten pumps in both her ass and pussy. Keep track of the pumps, if you let any air out you may want to completely deflate that toy and then start counting from zero. Once you reach ten pumps in each toy, leave the toys inflated inside of her until she comes. If she does not come a few minutes after you reach the maximum fuck her mouth until you come and be sure she swallows. 2) Fuck her with the large vibrator and make her fuck herself with it. It will be a struggle to get it in and Ann will say it feels like you are pulling her insides out when you make an outstroke. Just keep going and restrain her if you have to. Fuck Ann to orgasm with the large vibrator and once she has come take it out and put it on a chair or other hard surface. Tell Ann to get on top of it and fuck herself to another orgasm with it. When we used this toy Ann was able to get about seven inches of it inside her. If you get her to take more that's great but not absolutely necessary. Otherwise you can fuck Ann in any of her holes provided you use a condom when in her ass or pussy. Remember, Ann has selected you and she is your fuck toy for this evening and tomorrow morning. You are not making love to her; you are using her and fucking her." The guy Ann was sitting with at the bar to whom she had given the letter took a deep breath and asked if she was sure she wanted to do this. She responded by asking him if was capable of doing everything to her the letter said. He asked her again if she was sure and whether she had read the letter. Ann said that she had not read the letter and was not supposed to see unless he showed it to her. Ann again asked if the guy could do the things described in the letter and he smiled and said, "Hell, yea, I'll make sure you get everything you want and more." Now that they were both in agreement as to what was to happen between them the guy paid the check and he and Ann walked out of the bar and took the elevator up to her room. She said he took her hand as they walked down the hall to her room and politely escorted her inside. For those of you who have not read Part 1 or forgotten the description of Ann, she is 5'2" tall and weighs 115 pounds. She has brown hair and eyes. Her breasts are a natural B cup and she has a very, very thin waist which gives her a classic hourglass figure and an ass to die for. Although I had talked her into shaving her pussy a couple of times in the past she has in recent years kept a full bush. We never had children so her pussy is still nice and tight. Ann does not have any tramp stamps or piercings. The guy she selected, who I saw on the video she brought home, was about 6'2" and about 210 pounds. He looked like he worked out and had pretty well defined arms, chest and abs. He had black hair and was clean shaven. He was an executive for some company and he had an air of confidence about him which made him the perfect choice to administer the lesson to Ann. His name was Frank and he was divorced and unattached at the moment so he was horny as it had been a while since he had sex. For those of you into impossibly large, humongous, fire hose sized cocks, sorry, he was around six or seven inches. Once in the room Ann said Frank hugged her firmly and kissed her on the neck. She looked up wanting him to kiss her on the lips but he said, "Sorry, baby, the first place you are going to kiss me is on my cock." I would have loved to have heard that exchange but Ann had not had a chance to turn on the video camera. Once she got the camera on Frank told her to get the toy kit I had prepared and to open it and put the items out on the bed. The look on Ann's face as she saw the items in the kit was one of apprehension as she did not need to see the letter to know what was in store for her. Frank next told Ann to strip and she took off her blouse and skirt and laid them on top of her suitcase. Ann was not wearing a bra or panties and was left with only a garter belt, black hose and black shoes on. Frank told her to slowly turn around for him so he could see all of her. As she did he stepped up behind her and ran his hands over her body, evaluating her tits, ass and pussy. He gave her a slap on the ass and told her to go and use the bathroom because, as he put it, "She would be pretty full very soon." When Ann returned from the bathroom Frank was already naked and he took her hand and led her over to the bed and positioned her lying on her back with her head off of one side of the bed. Frank stepped up to Ann's face put his already semi-hard cock into her mouth and said, "Time for that first kiss baby." Ann started to suck and Frank got fully hard almost immediately. He started to saw in and out of her mouth and was quickly moving into and out of her throat due to both Ann's ability to deep throat reasonably sized cocks and the position her head was in. This is another example of the difference between my doing things to Ann and a stranger. When Ann gives me a blow job she usually controls the depth of penetration and works up to the deep throat part at her pace. With Frank, there was no warm up period. He was in her mouth, a few strokes and then into her throat. Frank continued to fuck Ann's mouth for a few minutes and the frequency and intensity of his groans increased. Ann, meanwhile, was making the most delightful gurgling and sucking noises. Frank was right at the edge and he looked down at Ann and said, "Your husband's letter said that you do not like to swallow cum and that I should make you do it but don't worry about the swallowing part because I am going to come as deep in your throat as I can get so it will go right into your stomach." With that Frank pushed all the way down Ann's throat and started to ejaculate. When she felt the first spurt Ann stiffened and her hands grabbed at the bed covers while her back came up a bit off of the bed. Frank stayed in Ann's mouth as he softened and told her to suck his cock as he withdrew so she would get every last drop of his cum. They rested for a few minutes and then Frank announced that it was time for the main event. I could see Ann shudder as the impact of these words hit her. Frank positioned Ann on the bed in the doggy position, pushed her shoulders down and started to lube her ass. He put first one, then two and finally three fingers into her ass and then added more lube to the inflatable butt plug. He positioned it at her opening and said, "Push back sweetie, you need to get this inside of you." Ann pushed back and Frank just held the butt plug in the same position. He made no effort to help Ann get it in or to push the thick part past the ring of her asshole. Ann was getting quite a workout from pushing back for so long and finally she grunted and pushed back hard and the fat part of the plug made its way past her sphincter and seated itself in her ass. This is again another difference in how a significant other and a stranger handle the same task. When Ann and I would play with a butt plug I would let her set the pace and work with her to help get it into her comfortably. Usually she would be lying on her side with one leg drawn up. Compare that to the humiliating ass up position Frank put her in and then making her force the plug into her own ass by fucking herself back on it until it was in place. Teaching My Wife Ch. 02 Frank then told Ann to rollover on her back and he started to play with her pussy. He remarked about how wet it was but decided to use some extra lube anyway because, as he put it, "The dildo was going to be in there for quite a while." Once he had both toys in place, Frank told Ann what he was going to do. He told her that the letter said that her previous maximums for pumps were seven but that her husband wanted him to take her to ten. Ann quivered at these words and would have rolled into the fetal position had Frank not stopped her. Frank left Ann for a moment and retrieved the ball gag and restraints from the other bed. He asked her if she thought she would need to be quieted or restrained as doing so now would lessen the time she had the inflated toys inside of her if he had to do it later. Ann said that when we played this way that she was not restrained although she acknowledged that she was going into uncharted territory as far as the degree of inflation was concerned. She opted not to be restrained or gagged although she looked at the ball gag closely as it was a new toy as I had not previously used one on her. "OK, let's get started," Frank said as he switched on the vibrator in the butt plug and set it for low. He told Ann that he would start with three pumps on each and that she was to tell him whether he was to start with her ass or her pussy. If she did not make a choice he said that he would do the pumps simultaneously. I could see Ann's eyes dart back and forth as though she were trying to figure a way out of this. Frank nudged her and said, "I'm waiting." When Ann still said nothing Frank said, "I guess it is simultaneous" and when Ann heard this she quickly blurted out, "No, start with my ass." Frank pumped the bulb for her ass three times making sure to maximize the size of each pump. Ann groaned as the butt plug expanded inside of her. Frank let her alone for 30 seconds and then gave three pumps to the inflatable dildo in her pussy. You could see from the expression on Ann's face and the way she moved that she was already a bit uncomfortable even though there was still a long way to go. Frank put down the inflation bulbs and started to play with Ann's nipples and to rub her clit. She began to respond a bit although the stimulation was not enough to overcome all of her discomfort. In a few minutes Ann had grown used to the size of the toys deep inside of her and sensing this Frank asked if she was ready for round two. He told her the second round would also be three pumps each. Ann trembled at his words and asked if she had to choose and he said that she did. Ann thought about it for a moment and said, "Pussy." No sooner was the word out of her mouth then was Frank pumping away. He only gave her a moment to rest before he put three pumps into the toy in her ass as well. Ann cried out and said, "The toys are too big. I cannot take any more!" Frank said that she had to take four more pumps in each toy and when Ann heard this she tried to get off the bed and away from Frank. Frank grabbed her around the waist and because he was ten inches taller and almost 100 pounds heavier it was no contest. He got Ann back on the bed on her back and said, "Well, I guess you do need to be restrained after all." Ann begged and pleaded for Frank not to tie her but Frank was having none of it. He took some of the ropes I had put into the kit and tied a loop around each of Ann's ankles and tied her legs spread wide apart to the bottom corners of the bed. One benefit of all of these activities for Ann was that it took her mind off of the two growing invaders in her nether regions and gave her time to better get used to their new size. The downside, however, was that it was always more difficult for Ann to reach orgasm when her legs were held wide open. No matter what was between her legs Ann always squeezed and rubbed her thighs together while working her way up to an orgasm and really clamped them together while she was coming. Frank did not know this as in the letter I only told him some things that helped to turn Ann on. After tying her legs Frank sat back and said, "Do I need to tie your hands and gag you as well?" Ann's eyes grew wide as she contemplated how much more she would not be in control if her hands were tied and she was gagged. It was bad enough having her legs tied open but also having her hands tied and being gagged would give her no control over what this stranger did to her, as if she had much control anyway. Ann said, "No, you don't have to tie my hands or gag me, I'll be good, just be gentle the rest of the way." "OK, for the next round you get one pump each to get you to the maximum you have had before with your husband, where do you want it first?," Frank asked. Ann let out a deep breath and meekly said, "Ass." Frank obliged and quickly put another shot of air into the toy in her ass and in the one in her pussy. Even though she was now inflated to her previous maximum, Ann did not react too badly as it was only one pump of air each instead of three as in the previous rounds. Nevertheless, she felt extremely full and did not see how she could ever take three more pumps. Frank again played briefly with her nipples and clit and that seemed to relax her a little. "OK, time to move into uncharted territory," Frank said. Ann started to beg and plead. "Please don't make me take any more. My pussy and ass feel like they are going to explode. I cannot take any more," Ann cried. Frank told her that for the next pumps she was to do the pumping. He pulled her hands down and put an inflation bulb into each and told her the one in her right hand was for her pussy and the one in her left hand was for her ass. Ann shook her head from side to side and said, "No, no, I can't do it, I can't take any more." Frank said, "If you are not going to use your hands to pump you do not need them and I may as well tie them to the bed." Ann continued to cry and beg and plead and Frank finally took the ball gag and put it in her mouth and tightened the strap behind her head. Now all you could make out were unintelligible sounds but Ann continued to be vocal. Frank said, "One more chance, do you want to pump?" and Ann went rigid and continued to try to talk through the gag. Frank told Ann that she had ten seconds to start to pump and counted down from ten. When she had not moved her hands to the inflation bulbs by the time he reached "zero" he took the handcuffs, cuffed her hands together and tied her hands above her head. You could now really see the fear and panic on Ann's face as she realized that this stranger was going to continue to expand the toys inside of her and that she was now truly powerless to do anything about it. Ann started to sob quietly while she awaited her fate. She did not have long to wait. Frank took the bulbs and said, "You know, this is taking too long. I am going to give you the remaining three pumps all at the same time and since I did not notice which bulb goes to which toy when I picked them up I am just going to pump the one in my right hand first and see which toy grows." Ann started to thrash around on the bed and Frank put his left hand on her stomach and said, "Be still." He gave her three quick pumps with his right hand and as he saw a slight rise under her bush he knew that he had pumped the toy in her pussy. Ann lurched up on the bed as best she could being restrained the way that she was and let out a cry that was loud even though she was gagged. Her whole body trembled and was covered with a light sheen of perspiration as she continued to moan and cry. Frank gave her a minute and then said, "Time to finish the job." He quickly put the final three pumps into the toy in her ass. Ann must have been exhausted by this point because she did not react as violently as she had to the pumps to her pussy. All she did was to shake her head from side to side and cry out loudly. Frank turned up the vibrator in the butt plug to its maximum and sat back to admire his handiwork. Ann just lay limply on the bed as if all of the fight had been drained out of her. After a few minutes Ann had pretty much quieted down and Frank took a chance and took out her gag. He told her that the toys would stay in her fully inflated until either she had an orgasm from the vibrator in her butt or she sucked him off and swallowed every drop. Ann told Frank that she had always had trouble coming when her legs were tied apart and that she could hardly feel the vibrator because of the size of the balloon that surrounded it. Frank smiled and said, "That's OK, I never turn down a blowjob from a pretty lady." Frank then untied and uncuffed Ann's hands so he would have better access to her mouth. He straddled her chest, looked down at her and told her that she would have to ask him to fuck her mouth and tell him that she wanted to swallow his cum. Even though Ann is vocal in bed with moans and assorted groans she was never one to say things like, "Fuck my brains out." I knew doing what Frank wanted would be out of character for her. Ann just lay on the bed with Frank's cock just inches from her mouth and said nothing. Frank looked down at her and said, "Well." When Ann still said nothing Frank reached behind him and took one of the inflation bulbs and told Ann that the letter had suggested ten pumps but said nothing about not going beyond ten. Ann started to plead and tell Frank that she could not take any more air in the toys and he said, "Then you know what you have to do." Ann blinked away the tears in her eyes and quietly said, "Please Frank fuck my mouth and make me swallow your cum." Frank told her that he did not hear her and that she would have to repeat what she said. Ann took a deep breath and repeated her entreaty and Frank told her that she could do better. Ann took another deep breath and then virtually screamed for Frank to fuck her mouth and make her swallow his cum. His cock was in her mouth before she got the last word out of her mouth. Because Frank had already come earlier he was able to last and Ann had to work for several minutes to get him close to orgasm. When he was close Frank pulled out of Ann's mouth and said, "Keep your mouth open. I' m going to shoot on your tongue." This would again be a new experience for Ann as when I came in her mouth I was always inside of it and not shooting in from the outside. Ann did as Frank told her and a minute later he shot five good shots of cum onto Ann's tongue. Frank told Ann to close her mouth and keep the cum there and he took his cock and squeezed the last few drops of cum out and wiped them over her cheeks and lips. He told her to swallow and she did knowing that her reward would be to have the toys deflated and removed from her orifices. Frank made quick work of deflating and removing the toys and Ann barely moved and was silent during the process. With her body empty of the toys Ann rolled over and fell asleep. As it was nearly 4AM Frank lay down next to her and did the same. Frank woke up first at about 9AM and went to shower. Ann was just stirring when he came out of the bathroom and when he saw she was awake Frank walked over to her, ran his hand through her hair and kissed her on the lips. Ann smiled and said, "Not bad for our second kiss." I saw that as a good sign because despite what she had been through the night before Ann had not lost her sense of humor. Frank told Ann to get cleaned up and that he would order breakfast. He told her to keep the bathroom door open so the room service guy could see her naked. For Ann, this again would be new territory as using our hot tub naked was as close as she got to being exposed to people. Ann was standing in front of the bathroom mirror fixing her hair when there was a knock on the door. Frank opened the door and Ann could see the room service guy look at her as he went past the bathroom door. Frank had the guy set up their breakfast on the table and while he was doing that the guy got a good look at the sex toys that were still on the other bed. Frank fumbled around pretending to go through his pockets to find the guy a tip and, of course, found nothing. He called out to Ann asking if she had any small bills to tip the guy and she told Frank to look in her purse. Frank replied that he was not comfortable looking in her purse as they had only just met the night before. This made Ann's status very clear to the room service guy. Frank insisted that Ann come out and find a tip for the guy and he met her as she came out of the bathroom door and took away the towel she had wrapped around herself saying, "You won't be needing this." Ann was totally mortified and you could see her getting red from embarrassment on the video as she stood naked while going through her purse in front of another stranger who was not only looking her up and down but who had seen the sex toys that had and would be used on her and who knew that she and her current male companion had only just met the night before. Ann eventually found a couple of bills and Frank had her give them to the guy. While she was standing in front of the room service guy Frank walked up behind her and grabbed both her arms and held her tightly. He said to the room service guy, "Go ahead, have some fun, she wants it." The guy, his name was Jack according to his name tag, reached out and played with Ann's nipples and her breasts. Despite her embarrassment and the fact that she was essentially being forced to let herself be groped, Ann's nipples hardened. Jack then turned his attention to her pussy and ran his hands through Ann's lush bush. He was surprised to feel that Ann was wet but she had not had an orgasm during any of the things she did with Frank the night before and she was very horny. Jack put one then two fingers into Ann's pussy and started to finger her vigorously. Ann started to hump back against his fingers and as she got weak in the knees it was a good thing that Frank continued to hold her. The fingering continued for a few minutes and Ann was moaning louder and louder. She finally came on Jack's hand and trembled for a few moments as her orgasm subsided. Frank told Ann, "Suck his fingers clean." Ann dropped to her knees and without embarrassment (after all, how can you be embarrassed after a guy has seen you naked, groped you and fingered you to an orgasm) she took each of his fingers into her mouth and licked them clean. This was something that Ann would do with me and she always told me that her pussy tasted sweet which it does and is one of the things that makes me able to eat her to multiple orgasms. Jack excused himself and Ann and Frank had breakfast with Ann, of course, remaining naked. During breakfast Frank reminded Ann that they had one more toy to play with before he left but that she was going to fuck him before that. His choice of words was interesting but I did not realize exactly what he meant until he put Ann on her knees and had her suck him to a full erection. Frank then had Ann put a condom on him and he lay down on the bed and said to her, "Get up here; you have some fucking to do." Ann got up over Frank, positioned his cock at her pussy and slowly lowered herself down taking its full length deep inside of her. He told her that she was going to do all of the work and she started to slowly move her hips up and down. Ann got going pretty good and you could hear the sloshing of her wetness on the video with each stroke. As Frank had come twice in the last few hours his stamina was back and he was able to delay his orgasm for nearly 30 minutes. Ann, on the other hand, had only had a small orgasm when Jack fingered her and she went wild. On the video you could hear her say, "I'm coming, I'm coming!" at least five separate times and as she always has a number of smaller secondary orgasms after most major orgasms, I knew that she got quite a workout both from the orgasms as well as from having to work to bounce up and down on Frank's cock for so long. After Frank came he told Ann to take off the condom and drain his cum into her mouth. Ann was appalled but eventually did it when Frank pointed out that the sooner they finished the sooner she would be on her way home. The fucking over that left one more scene for Frank to enact with Ann. Frank told Ann to get the large vibrator, the one that was supposedly modeled after a porn star's cock. She trudged over to the other bed and returned with the toy and some lube. Frank told her that the letter said that he should fuck her to orgasm with it and then make her fuck herself to a second orgasm with the toy affixed to a hard chair by the suction cup at its base. Frank chuckled and said, "I bet you are going to have to work pretty hard to come twice more after coming as much as you did while riding my cock." Ann never realized the consequences of coming as much as she did while riding Frank's cock as all she was thinking about was to get some needed relief after not having an orgasm during last night's session. Frank knew exactly what he was doing as he held himself off for as long as he did during the fucking giving Ann ample time and opportunity to come and now Ann had to come twice more to be allowed to leave for home. Frank told Ann, "Lie down on the bed and put a pillow under your ass." He fingered her cunt and pushed in a fair amount of lube. He then put the head of the vibrator between her pussy lips and started to push it in. Despite having had her pussy stretched by the inflatable toy the night before and Frank's cock just a while ago it was slow going. Ann panted as if she were in child birth as she struggled to accommodate the huge toy being pushed inside of her. After some persistence the toy was lodged as far as it would go in Ann's cunt. Frank smiled and said, "Get ready to feel your insides being pulled out." Ann knew what she was going to feel as she had complained about that feeling when I fucked her with the same toy. Frank slowly pulled the vibrator out and Ann quivered and said, "Oh my God." He pushed it back in and then pulled it out again. Ann tried hard to stay as calm as possible but the vibrator did look as if it was pulling her insides out. Ann would moan, beg Frank to stop and pound her fists on the bed. Nothing she did stopped Frank from pumping the toy in and out of her. After about ten minutes of having the toy shoved in and pulled out of her, Ann's cunt began to loosen up and she began to feel the faint stirrings of an orgasm. Even so, it took her another ten minutes to reach orgasm. When I next look at the video I want to count the number of strokes Frank gave her with the vibrator but it has to be well into the hundreds. Once Ann had come down from her orgasm, Frank pulled the vibrator out of her and said, "OK, baby, just one more orgasm and you are done." Frank pulled out the wooden desk chair and mounted the vibrator on it with the suction cup at its base. He turned to Ann and said, "Saddle up." By this time having had an orgasm at the hands of Jack, numerous orgasms while fucking Frank and another while Frank fucked her with the vibrator Ann knew that she would have to work hard to wring one more orgasm out of her tired and used body. She reluctantly padded over to the chair, straddled it with her legs, lined up the head of the vibrator with her cunt and lowered herself down. She immediately realized that if she let herself down all the way that the vibrator would reach deeper inside of her than it or anything else had before. As I mentioned earlier, the vibrator was about 10 inches long with a diameter of over two and a half inches. When I had used it on Ann she had taken maybe seven inches and it did not look like Frank had gotten any more of it into her earlier. Ann started to slowly and carefully fuck herself with the vibrator always taking care not to go too low. Unfortunately time was not on Ann's side as it was going to take some doing for her to have another orgasm. She fucked the vibrator up and down for about ten minutes when the first moan escaped her lips. It took another five minutes before her breathing quickened and although she was starting to get warmed up you could tell she was getting tired. Her legs were feeling the strain of first having to fuck Frank and now having to fuck herself with the vibrator. Teaching My Wife Ch. 02 Ann continued on like a trooper but it was growing increasingly clear that she would have to sit down on the chair for a break soon to take the strain off of her legs. She tried easing herself down gently but as the toy got to new depths she would get a second wind and spring up quickly. "Can I get off this thing and take a break?," Ann asked Frank. "No, you have to stay on until you come," Frank replied. Ann whimpered at his response and went back to trying to get herself off. She continued to move herself up and down on the monster that was between her legs but she was clearly running out of gas. Fortunately she was also getting closer to having an orgasm. Ann continued pumping and on one of the upstrokes she came violently. Her orgasm caused her legs to finally give out and she collapsed on the chair taking the remaining length of the vibrator into her tired body. Having the toy reach its full depth caused Ann to have another more violent orgasm and if Frank had not held her up she might have fallen off of the chair. Ann just sat there for a few minutes with the ten inches of the vibrator buzzing in her cunt. She looked down at where it disappeared into her and said, "Wow, I did take all of it." Frank asked, "Do you need help getting up?" Ann said, "Just let me sit here for a few minutes." She found the control for the vibrator, increased it to maximum and just sat there taking in all of the stimulation. Amazingly she had another earth shattering climax a few minutes later and as she came she pulled her knees up towards her chest taking her feet off of the floor leaving her perched on only the vibrator meaning that if there was any length outside of her it was now fully in her. Frank helped Ann off of the chair and she went to get cleaned up. While she was in the shower Frank got his stuff together and when Ann came out he told her he waited because he wanted a good bye kiss. She asked him if he wanted a kiss like their first or their second and he said, "Both." They French kissed for a few minutes and then Ann dropped to her knees in front of Frank and sucked him off. She swallowed without any prompting from Frank and even sucked the last few drops of cum out of his dick. She swallowed those as well and then wiped his dick over her face to dry it off. Ann came home in a better mood than after her first experience because this time she had come many, many times. Ann also appeared to be learning from her experiences because since she has been home she has always swallowed my cum and I have used all of the toys on her a couple of times without her complaining or whining. Once she even put in the last two pumps on the inflatable toys in her ass and cunt without any prompting from me. I think that she is well on her way back to being the whore in the bedroom that she was earlier in our marriage and look forward to her next out of town trip. Teaching My Wife Ch. 03 WARNING--This story has BDSM elements in it so if that is not for you then you should move on. I wanted to get that out there because a few people complained that Chapter 1 of this series was mis-categorized as a loving wife story. To me, the stories in this series are primarily loving wife stories but I wanted to give people who may think that stories should encompass only one genre a heads up. * For a full background readers should review Chapters 1 and 2 before reading this chapter. This is the story of how my wife Ann, who used to be sexually adventurous, became more and more conservative and how I set out to change things back to and beyond where they were. As I described in Chapter 1, over the years Ann had become more plain vanilla as far as sex went. The adventurous woman I described earlier had seemingly left the building along with Elvis. Vibrators, if we used them at all, were smallish and used mostly on her clit. We began to argue more and more about sex and I eventually told Ann that if she were not willing to again be a whore in the bedroom I would find someone who would. "Whore in the bedroom" are her words as she told me shortly after we were married that she thought an ideal wife was a lady outside of the bedroom but a whore in the bedroom. I told Ann that she needed to be taught how to once again be a whore in the bedroom but that because she had over the years pulled back the sexual boundaries we once had that these lessons would be from other men. I knew that if we tried to become more adventurous and Ann objected to something that I was doing to her that I would slow down or stop because I loved her while a stranger would likely not stop and say something like, "Come on, baby, you can take it." Ann would not be as free with a stranger to impose her boundaries and would be taken beyond those limits. Because Ann went out of town for three or four days at a time in her job about every six weeks we decided that her lessons would be during these trips. I would pack her a kit of the items to be used for each lesson along with a video camera and an instruction letter she was to give the man she selected. So as not to interfere with her job, Ann would extend her trip for an additional night at our expense and tell her company that an old college friend, etc. lived in the town she was visiting. The additional night would be lesson night. On each of her first two trips Ann engaged in activities with other men that we had done together earlier in our marriage such as having her pussy lightly flogged to orgasm, filling her ass and pussy with ice and then getting fucked when it melted, anal sex, having her ass and pussy stuffed with inflatable toys that were then inflated beyond her previous maximums, being fucked with a porn star sized vibrator and plain old fucking and sucking. Ann was also exposed to a room service waiter by one of the men and forced to endure being groped and fingered by him to orgasm. She also swallowed more cum than she had in a long time with me. Because of these experiences Ann was gradually returning to the sexually adventurous woman she had been earlier in our marriage. However, I told her when we started this that her training would encompass both things we had done as well as new things that she had not experienced before. I decided that on her third trip it was time for some more of those new things. Ann and I had talked a lot about what happened on her first two trips and watched the videos she brought back numerous times. It was a terrific turn on for both of us but we realized that we had been risky in what we had her do with strangers and lucky that none of them had harmed her. Ann admitted that she was scared at times during each of the previous encounters but said that the fear in her stomach had actually turned her on more than she would have normally been. She also said that she now realized that it was best to have strangers with whom she had no prior relationship do her training because she realized how easy it was for her to say "stop" or "slow down" to me. As Ann experienced in her first two sessions, strangers did not listen nearly as well to "stop" or "slow down." As I mentioned in an earlier chapter, I had often stuffed Ann with a vibrator in her ass and pussy and then fucked her mouth. I had also fucked her ass while she had a vibrator in her pussy and vice versa. She really got off on having two or all three of her holes filled but never agreed to take the next step and to have a threesome or moresum. That was about to change as I told her that on her next trip she was to have sex with a group of guys. Ann gave me a concerned look and said that she would be afraid to be with a group of men because she would really be at their mercy. She explained that she always found men to be competitive when they were with other men especially around women and that she was afraid that the guys would try to "one-up" each other at the expense of her pussy, ass and mouth. She also said that it would be harder for her to find a group of guys. Ann said that in any group there would be at least one guy that she would not be 100% comfortable with but that she would have to take him or turn down the whole group. She also pointed out that she only had one night to do this at the end of her trip so she would have limited time to find and recruit more than one guy. I was a bit surprised that her objections were not to a group but to what might potentially go wrong so I asked her if she was comfortable with taking on a group of men. Ann said, "A few months ago before we started this I would have told you no effin' way. Since then I have been fucked and more by two strangers so I am no longer the faithful wife I once was and as we both want me to be a whore in the bedroom and you obviously want the next step for me to be with a group of men and I agreed to do this to improve our relationship I am willing to give it a shot." I told Ann that I had a solution to her concerns and that was that I would be one of the guys in the group. I told her that I had always wanted to get her into a threesome, foursome, etc. and that I was damn well going to participate in her first one. Ann was silent for a moment and then said that my participation would make her feel better but she asked what I would do if she asked the guys to stop or slow down and they keep going. I told her that I would follow the lead of the other men and would only intervene if they wanted to do something that would permanently hurt or mark her or violated the condom, video or other rules. As far as fucking, sucking and other sex she was on her own and she would have to take whatever they, and I, dished out. Ann thought over what I said for a few seconds and said she thought it was a good idea. She said she would definitely be more comfortable with me in the group and that if I was going to let the other men take the lead that she would still be used as a whore which was the whole point of her training. We talked a bit more about the details of how to make this happen and decided that we should use the letter routine again. I would write a letter for Ann that she would give to the men that she picked that she would say was from her husband. It would outline what was to be done to and with her and refer to a kit of toys that she had that they were to use on her. She would also tell the other guys that she had met a man at lunch (me) and wanted him to also be part of the group that would fuck her. Once it looked like Ann had the rest of the guys lined up she would call me on her cell and ask me to come down to the hotel bar. We planned on getting separate rooms in the hotel so that none of my stuff would be in her room and we would take out any pictures, etc. we had of each other in our wallets so that there would not be any way to link us together as Ann had kept her maiden name after we married. We took these precautions because my standing to intervene would be compromised if I were thought to be a cuckold husband. If I was just another of the guys I would be able to say, "Hey, that's not the deal," if one of the other guys went too far. Alternatively, if Ann started to yell about being seriously hurt or assaulted I could grab the offending guy, get in his face and say, and "Knock it off asshole, I am here for a night of fun and do not want to wind up in jail because of you." I would still be outnumbered but the more tools I had to keep everyone on the reservation, the better. While on the subject, I do not consider myself a cuck. Admittedly I get off on having other men do things to my wife but those things are generally my idea, not hers. She is not telling me to stay at home and keep my hands off of my little dick while she goes out and fucks other guys and brings me a cream pie. There will never be a cream pie because we firmly believe in safe sex and anytime anyone other than me comes in her ass or pussy they will be wearing a condom. What I get from all of this is a better sex partner with whom to share my bed at home. Ann's new outlook has also caused her to agree to swapping and last weekend traded with an attractive couple who live near to us (but that is another story). Looks like I will be getting a lot of sex from my newly sexually open wife and other women as well. If that makes one a cuck I think most guys would ask, "Where do I sign up?" For those of you who have not read Chapter 1 or 2 or forgotten the description of Ann, she is 5'2" tall and weighs 115 pounds. She has brown eyes and medium length brown hair that at times looks reddish in certain light. There must be some redhead in there somewhere because Ann's skin is very white and she has a lot of reddish freckles on her tits and shoulders. Her breasts are a natural B cup topped with light brown/pinkish nipples which get about a half an inch long when she is aroused. Ann has a very, very thin waist which gives her a classic hourglass figure and an ass to die for. Although I had talked her into shaving her pussy a couple of times in the past she has in recent years kept a full bush. Ann does not have any tattoos or piercings. We never had children so her pussy is still nice and tight and, of course, she does not have stretch marks. Ann had a business trip coming up in about a month and we decided that, as before, she would extend her stay by an additional day giving her time to take care of her job responsibilities and leave her free for fun on the extra day. Fortunately for our wallet this trip was to a city only a little over a two hour drive from where we lived and as her company did not permit employees to fly unless the trip was over 200 miles, Ann would be driving out Tuesday morning. Ann did not mind driving and said that she would also avoid the hassle of having to check the bag with her "toy kit" to avoid having to answer embarrassing questions from the TSA folks at the airport. I would take our other car and drive up on Friday morning and we would meet for lunch so that Ann would be telling the truth when she told the other men that she had met a guy for lunch that she wanted to include in the group. All that was left to do was to write the letter and put the toy kit together. As Ann had already picked up a guy on each of her prior trips we did not need to talk about how she should dress or act to do that but we did talk about various ways she could recruit a group of guys. I suggested that Ann make eye contact with a guy in her target group, smile and if he smiled back then walk over to the group and ask if she could join them. She thought this would be too aggressive for her but said she would keep it in mind as a fall back strategy. Ann said what she thought she would do is to make eye contact, smile and exchange glances towards one guy in a group and hope that he eventually came over to her while she was sitting at the bar. If he did she could talk and flirt with him for a while. If she liked him and things were going well she could suggest that they go back and sit with his friend(s) or wait for his invitation to do so. She would talk with his friend(s) and see if she was comfortable in recruiting them to gang bang her. If she was, she would tell them the story of how she had gotten too conservative in bed for her husband's tastes and how he had convinced her that she needed to learn how to be more of a whore and that the best way for that to happen was for her to find other men to handle her whore training. If they reacted positively, as if there were a group of guys that would not to a petite, attractive woman making such an offer, Ann would say that they had to agree to let her video what they did and that they had to wear a condom if they were in her pussy or ass. She would also tell them that she had met a guy at lunch who she wanted to include in the group. After giving them a few seconds Ann would take out the letter, give it to them and explain that the letter was from her husband and detailed what he wanted to see done to her. Once they finished reading the letter she would ask if they were OK with the conditions and limits in the letter and if they were they would be off to her room. The letter I gave her read as follows: "If Ann has given you this letter then things have progressed pretty far and she wants you to use her and fuck her. Ann is my wife and she has agreed that she needs to be trained to be more of a whore in the bedroom. She is yours for the night provided that you allow her session with you to be videotaped and use a condom when you are in her pussy or ass. Other than that she is yours to do with as you see fit but you must at least do the things listed in this letter to her. Ann understands and has agreed that once the door to her room closes with all of you inside she is not allowed to say "no" to anything other than violations of the video and condom rules or activities that could cause permanent injury or damage to her or result in her being permanently marked. Scat and water sports are also off limits. There is a toy kit in Ann's luggage. The kit contains a large tube of sex lube, a blindfold, condoms, a vibrator, a ball gag, handcuffs, a ping pong paddle and assorted lengths of rope. You should not have to restrain Ann but the restraints are there if you need them because some parts of this experience will be new to her in many ways. Because I love Ann I was reluctant to push her limits and would usually back off when she wanted to stop or slow down when we were having sex. You, on the other hand, have no emotional attachment to Ann and hopefully all she is to you is an attractive woman with whom you are going to engage in hot kinky sex. During the course of the night, Ann may object to certain things you are doing and she will carry on and try to talk you out of it but do not take "no" for an answer. Ann used to be very hot in bed and I hope her training gets her back to that state. She is your slut for tonight so make good use of her. When Ann gets hot she likes the side of her neck (below her ear) licked and kissed. If she really is getting into it you can lick her ear also. Another of her erogenous zones is the pussy hair above her clit. When Ann gets close to cumming she will run her fingers through that part of her bush and she gets off on having that done to her. Ann likes to be able to rub her thighs together during sex and says it makes her get off better. She would have a harder time cumming if I held her legs apart or tied them open. Keep this in mind as you may want to facilitate her orgasms on some occasions and prolong her wait on others. OK, now for the things you are to do to Ann: 1) Put her on her knees and tell her she has two minutes to get to know each of your cocks using only her mouth. If she does not keep her hands away use the handcuffs. Tell Ann that during the two minutes she is to get to know each of your cocks as after she had sucked everyone she will be blindfolded and then have to identify the owner of each cock again using only her mouth. If she guesses right she will only have to suck off the guy and swallow his cum. If she guesses wrong, the guy(s) she guessed wrong about should put her over their knee or otherwise bend her over and give her 10 swats each on her ass with the ping pong paddle. Once she had been paddled she should suck off the guy(s) who she guesses wrong and swallow their cum. 2) Single, double and triple penetrate her. Put her in whatever positions you want and make her take your cocks (with condoms on when in her ass or pussy). Try to find positions where Ann has to fuck you, make her do the work whenever possible. Her pussy and ass are pretty tight so double anal or double vaginal may not work but if you are into it you can give it a try. Be sure to use lots of lube in Ann's ass and pussy to keep her comfortable. Remember, Ann has selected you and she is your fuck toy for this evening and tomorrow morning. You are not making love to her; you are using her and fucking her." I did not show Ann the letter as I would be participating and that would be her safety margin as opposed to the first session where she knew 100% up front what was going to be done to her. The next few weeks dragged by but it was finally Tuesday morning and Ann had finished packing her car. I went down to say good-bye and I kissed her deeply. I pulled up her skirt and found she was not wearing panties. I rubbed her cunt and when I went to slip a finger inside of her it slid in without resistance because she was that wet. "Hmmmm, looking forward to Friday night?" I said. Ann replied that she had gotten hornier and hornier as her trip got closer. I waved to her as she pulled away and I could not help but marvel about how far she had come in the last few months. Friday was going to be a big day for both of us, especially her. Ann and I phoned each other a couple of times during the time she was gone and teased each other about what was going to happen Friday night. Friday morning came not soon enough and I packed my car and left to meet Ann for lunch and more. As planned, we had lunch together and agreed that she would call me later once she had picked the other guys that were to be in her first gang bang. When we talked about doing this I told Ann that she should get at least two more guys for our adventure. Any more than that was up to her but I cautioned her that the more guys that there were the longer she would get fucked and have to suck without a break. As Ann had never been with more than one guy before I found her some gang bang videos on the internet so she could see what it might be like. I tried hard to find some that were realistic as opposed to those where some skank covered with tats kept spitting on guys' cocks and moaning inanely. I also found her some stories written from a woman's perspective about what it felt like to be used for hours by a group of guys. Ann took well to this homework assignment and when I checked her browsing history I saw that she had looked at every video and every story, some of them several times. While definitely not the same as the real thing, looking at the videos and reading the stories at least gave Ann a preview of what she might expect. Ann's business meetings took longer than expected on Friday afternoon and it was almost 9:45 PM when she finally got to the hotel bar after freshening up. She looked hot in her short skirt and tight top as she maneuvered through the bar on her CFM heels and onto a bar stool where she would be able to cross and uncross her legs playing peek-a-boo with whichever guy she wanted to notice her lack of panties. Ann quickly got the attention of three guys who were sitting at a table not far from the bar. After a few minutes of eye contact, glances and smiles one of the guys got up and walked over to the bar and sat down next to Ann. He introduced himself and offered to buy her another drink which she accepted. They talked and flirted for a few minutes before the guy, Tony, asked if she wanted to meet his friends. Ann said "yes" and Tony helped her down off the bar stool and guided her by the elbow as he escorted her over to where his friends were sitting. Teaching My Wife Ch. 03 I was a little surprised that Ann had picked a group of three as she had said she would have preferred to start with just three guys including me. She later told me that she was worried because besides these guys there was only one other small group of guys in the bar and they were not that attractive. Ann said that she thought that these guys may be her only shot. She also told me that she thought that she could handle more than three guys if she had to because, after all, she had the same equipment as the girls in the videos she had watched. Tony introduced his friends, Bob and Cliff to Ann and she hugged each of them and did the air kiss routine. Ann sat down with Bob on her left and Tony slid in on her right. Before moving on, let me describe Ann's new friends. Tony was about 6'3" tall, broad shouldered and around 220 pounds. He had dirty blond hair, blue eyes and was clean shaven. Tony, like every guy doing pick-up duty in a bar, claimed to be single despite the lighter line on his ring finger which the wedding ring he had stashed in his pocket normally covered. He and his friends were in town for a conference that was to start with a golf outing Saturday afternoon. Bob was 6' tall and weighed in around 190. He had brown, curly hair, brown eyes and a mustache. Cliff was the smallest of the group, around 5'6", and looked to have the lithe, sleek, athletic body type that you would normally find on a gymnast. Turns out he actually was a gymnast in college and now owned a gymnastics school. Cliff had black hair (crew cut) and brown eyes. Ann never asked whether Bob and Cliff were attached or had significant others and they did not offer that information. Bob was wearing a ring that could have been a wedding band but its design was a bit unusual so it could have been just a piece of jewelry. Ann was wearing her wedding band and that, coupled with her dress and demeanor, soon had her trio of new friends flashing knowing smiles to each other that they had lucked on to a proverbial hot wife, something they hoped existed but that could have been just an urban legend. Tony ordered another round for the table with Ann asking for a tonic water and lime while Tony, Bob and Cliff had something more potent. Ann could tell from the used glasses and the signs on the table promoting the happy hour special of "two-fers" that Tony, Bob and Cliff were feeling no pain. Ann and I had not factored into our discussions the possibility that her gang bang crew could be even more aggressive due to the effects of alcohol. Ann said that she worried about this for a few minutes but relaxed when Tony, Bob and Cliff acted like they were sane and reasonable. Because the sexual tension in the air was already palpable at their table Ann said she was not surprised when she felt first Tony and then Bob place a hand on her thigh and slowly start to rub higher and higher soon getting above the tops of her stockings. Just as Tony was about to reach Ann's panty less pussy Ann broke the mood and said, "Let's talk about the obvious." She told the guys about how she had become less and less adventurous sexually and how she and her husband had come up with her having these types of encounters as a way to learn to be more of a whore in the bedroom. She said that she wanted the guys to be part of her next encounter provided they agreed to the three conditions of allowing the session to be videotaped, wore a condom when they were in her pussy or ass and followed the instructions in a letter her husband gave her. Ann then took out a copy of the letter from her purse and gave it to the guys. They read it and passed it back and forth for a while. When they were done Ann asked each of them if they agreed to video, condoms and letter instructions and they said that they did. Ann then told them that she had met another guy for lunch that she wanted as part of the group and if they were OK with it she would call him now. The guys, of course, agreed and Ann called me on my cell and said to meet her in the bar. I waited about five minutes and made my entrance, walked up to the table, leaned over, gave Ann a peck on the lips and introduced myself to the guys. I sat down and there was an uncomfortable silence at the table as though everyone was waiting for someone else to say something. Tony broke the silence by announcing that he would take care of the check and went in search of our waiter. Bob asked if I had seen the letter and I said that Ann had shown it to me at lunch. With the bill settled Ann got up and we all started to follow her out of the bar. We were half way out of the bar when we heard a voice from one of the tables we passed calling out Cliff's name. We slowed and looked in the direction of the voice and saw a black guy coming towards Cliff. When Cliff recognized him he opened his arms and they hugged for a few seconds and were clearly happy to see each other. Cliff introduced Gary to the group as someone against whom he competed in college and said that they were together on several AAU gymnastics teams and even made it to the Olympic trials together one year. Gary was just a bit taller than Cliff and still looked like he could pommel a horse or something. Gary and Cliff talked for a minute or two and the whole time Gary was glancing over at Ann and the other guys that were with her. He seemed to have figured out what was up. Gary moved closer to the rest of us and asked "So where you folks going now?" Cliff sort of hemmed and hawed as did Bob. Gary, obviously looking for an invitation to come along, repeated his question and still did not get a coherent answer from anyone. He looked right at Ann and said, "Oh, I get it; some women just do not like black guys." You could tell Ann was getting uncomfortable as the bar had started to fill back up and we were standing in front of a couple of tables that were full and people were beginning to listen more intently to the conversation we were having. Ann later told me that she was afraid that because of the way she was dressed and that she was leaving with four guys that everyone in the bar was watching her and would think that she was going to let the four guys she was leaving with all fuck her. Gary could sense her discomfort and continued to press the race angle saying, "OK, well why don't you four guys and the lady go ahead and..." when Ann interrupted and said, "I don't care if you are black or not. You can join us if you want." Ann later told me that she thought that Gary was going to finish his sentence by saying something like, "have fun fucking" or something similar. Just as we turned to continue to leave the bar the guy Gary was sitting with stood up and called out "Hey wait, I'd like to go along too." We slowed our pace and he blended into the group and Ann did not raise any objection nor did anyone else. I later learned that his name was Will. He was about 6' tall, 185 pounds and also black. This was really going to be a night of firsts as Ann had never had sex with a black guy and now there were two black guys in her first ever gang bang group of six. Ann was really going from zero to sixty in a big hurry. When I think about this little scene I really see how Ann is a lady outside of the bedroom but a whore in it. She was leaving a bar dressed provocatively with four guys following her and was leading them up to her room to fuck her but she did not want the other people in the bar to know that. She wanted the people in the bar to think of her as a lady rather than as a whore who would soon be spreading her legs for a bunch of guys she just met. Gary and his friend, Will, played that together with the race angle to become part of the evening's fun. Ann led her now growing group out of the bar and over to a quieter area of the hotel lobby. She said "We all know what is going on and I was not sure I wanted two more guys but do not want to make a scene so Gary and Will are in." She then gave Gary and Will a crash course in why she was doing this, the condom and video rules and the letter. She gave them another copy of the letter from her purse and when they were done reading it made each of them acknowledge that they would do what it said and adhere to the video and condom rules. My mind was running a hundred miles an hour during this time. I was turned on as hell that Ann was going to get banged by six guys including me but was worried about things getting out of hand, as if they hadn't already. However, there was nothing I could do except go with the flow and be ready to step in if anyone tried to do anything to truly hurt Ann or otherwise break the rules and hope that I would not be outnumbered five to one if I did. While my mind was trying to process all of this we made our way to the elevator, up to the correct floor and walked down the hall to Ann's room. She opened the door and led us in and when the lock clicked behind us we both knew that her fate had been sealed. I knew it better than Ann because I knew what the letter said about her not being allowed to say "no" to anything other than violations of the video and condom rules or activities that could cause permanent injury or damage to her. Ann had not yet seen the letter. Tony waited until we were all well inside of Ann's room and said, "OK, let's go over the instructions one more time before we start" and read the letter out loud. Ann blanched and shot me a glance when he read the part about her not being to be able to say "no" to anything except violations of the video and condom rules or to anything that would permanently hurt or damage her or scat or water sports. She cringed when he read the part about the cock ID contest and that she would be swallowing a load from everyone there. "No, no you can't make me do that," Ann interrupted. Tony looked at her and said, "The deal works both ways. You made us promise that we would follow the video and condom rules and the instructions in the letter and you are going to do the same thing." Ann just hung her head and said nothing. Bob suggested that if anyone needed to use the facilities that they do it now before things got going. As Ann had used her hotel points to get tonight free and to upgrade her room she had a suite with a full bath off of the bedroom and a half bath off of the sitting room. That made things easier as Ann used the main bath and us guys used the one off of the sitting room. We all reassembled in the sitting room and Bob set up the video camera. Tony, who seemed to have put himself in charge, took Ann by the hand and helped her up on the coffee table. Tony stepped away and said, "Show us what you got honey." I could see Ann's fingers trembling as she fumbled with the buttons on her top and she finally got them open, slipped it off of her shoulders and handed it to Tony. She next opened the clasp on her push up bra and her tits popped into view prompting hoots and hollers from the guys. She handed the bra to Tony as well. Ann rubbed her hands over her tits and I think she was just doing it to buy a few more moments before being fully exposed to everyone. It had an immediate effect on the guys who urged her on and I could see the startled look in her eyes when she realized she had been acting like a stripper. She put her hands down at her sides and stood still for a while until Tony said, "Finish the job." Ann paused for a moment and then undid the button on the side of her short skirt, opened the zipper and slid the skirt down her legs. When it hit the top of the table she stepped out of it and Tony moved it out of the way. All of the guys cheered and applauded and I joined in. It was hard to read the expression on Ann's face. She was standing there on a coffee table in front of six men, five of them complete strangers, naked except for a garter belt, hose and CFM heels. She had heard what the letter said and knew that her ability to say "no" was very limited. She knew that she was going to get a workout like she never had before and that she was going to have to fuck and suck and more until these guys were satisfied and done with her. Her expression was a mixture of apprehension, lust and determination. When I described Ann I did not talk about her emotional makeup. She is often hard to convince to do something but once she makes up her mind she is one of the most determined people I know. It looked as though Ann knew she would need all of her determination to get through the next couple of hours. Tony turned to the rest of us and said, "OK, let's show Ann what we have for her." There was a flurry of zippers opening and clothes flying off until there were six naked men standing around Ann. Cliff helped Ann down from the coffee table, took her into his arms and kissed her deeply. When he was finished he said, "I wanted to do that before you drank everyone's cum." Ann trembled slightly at his words and her eyes darted back and forth across the array of cocks that would soon be in her mouth and other orifices. Meanwhile Tony had gotten a copy of the letter and reread the first thing that we were to do to Ann. He walked to the center of the room and dropped one of the pillows on the floor. Then in a decent imitation of a game show host he said in a booming voice, "Lady and gentlemen, it's time to play 'name that cock.' Our first contestant from Room 457 of the Marriott Hotel is (pause for tension to build) Annnnnnnnnnnn, come on over here and kneel down." This cracked everyone up including Ann and she ran to the middle of the room doing her best impression of a ditzy game show contestant grabbing at Tony's arm and jumping up and down. Tony then explained the rules of Name That Cock. Ann would have two minutes to suck and otherwise use only her mouth to get to know each of our cocks. She would then be blindfolded and given an additional two minutes with each of us to try to identify the owner of each cock. Tony took Ann by the elbow and positioned her over the pillow. "Kneel," he said as he firmly pushed down on her shoulders. The rest of us lined up in the order that Ann had picked us to participate which meant that I was first, then Tony, Bob, Cliff, Gary and Will. Cliff was wearing a sport watch that we would use for the timing and he said, "Ready, set, go." Ann opened her mouth and took my cock into it. She should already know my cock as she had been sucking it since before we were married but she still did a good job of using her lips and tongue to get a feel for the shape of its head and other aspects that she may be able to use to identify it while blindfolded. "Time's up," Cliff called and I stepped away from in front of Ann and Tony took my place. Cliff again said, "Ready, set, go" and Ann started to minister to Tony's cock. This process continued until Ann had had a chance to such each cock for two minutes. Because I had gone first and grabbed the chair closest to Ann I had a good view of Ann sucking each of the other cocks. Like most straight guys I did not spend a lot of time looking at other men's cocks but when they are in your wife's mouth it is hard not to notice. I thought that Ann might have a hard time telling some of the cocks apart because, for example, Bob and I were about the same size, we were both cut and I was just a bit thicker. Gary and Cliff had similar uncut cocks that looked a shade less than six inches. Will and Tony were bigger at 7.5 and 8.5 inches respectively but about the same thickness and both were cut. Because Ann could not use her hands she would have to deep throat some fairly big cocks to tell the length difference between Tony and Will. Tony told Ann to stand up and put the blindfold on her. He then spun her around a few times, held her and stuck a finger or two into her pussy and worked them in and out until she moaned a little. He then handed her off to another of the guys and she was passed back and forth like that to all of the guys getting fingered and otherwise groped in the process. The last guy, I think it was Bob but will have to look at the video again, led her over to the pillow and pushed her down to her knees. Tony gestured to all of us not to talk and pointed at Cliff to go over and stand in front of where Ann was kneeling. When Ann sensed that someone was standing in front of her she started to move her head around trying to get him in her mouth and eventually found his cock and sucked it into her mouth. When the two minutes were up Tony gestured to Cliff to step away and he did. Tony then said to Ann, "Name that cock." Ann thought for a moment and said, "I think it was Gary." A good guess considering the similarities between Cliff and Gary but wrong. This continued until Ann had sucked everyone for an additional two minutes each and she was able to guess me, Bob and Will correctly. Under the forfeit system in the letter she was to get paddled 10 times each by the guys she missed. Tony came over to her and took her blindfold off, told her the final results, led her over to a chair and draped her over it. Some of the other guys quickly tied her legs and arms to the chair so that her ass was sticking up and out as an inviting target. Tony asked Ann if she needed to be gagged and she said, "No, I can take it, my husband used to use that paddle on me." Although Ann had experience being paddled when we used to play more aggressively she was about to find out that strangers hit harder than husbands. Tony stepped away and Gary took up a position behind Ann and started to spank her ass with the ping pong paddle. She was silent for the first two strokes and then started to grunt with the third stroke. By the fifth stroke she was getting louder and by the seventh she was sobbing loudly. Gary gave her the last two blows and on the last she yelped pretty loudly. With 20 spanks left to go Tony decided that Ann would not be able to keep quiet and gagged her. She protested and sputtered but he forced the ball gag into her mouth and tied the strap behind her head. It was a good thing he did because Cliff and Tony himself really let her have it. She bucked and shrieked through her gag with each blow and her ass got redder and redder. When she had received the final blow Tony untied her but warned her not to rub her ass because he wanted her to continue to feel the fire. I admit I got a little worried about how hard they were paddling Ann but decided that I should not intervene because the paddling, although much more than she had experienced before, would not result in permanent damage or leave marks on her. That was the standard for my intervention that Ann and I had agreed upon before we started this adventure. After she was untied Ann just stood there moving from one leg to the other with tears still running down her cheeks. I could tell that she desperately wanted to rub her burning ass but she stoically bit her lower lip and kept her hands at her side. She clearly did not want to disobey Tony. Tony walked over to Ann, took her by the hand and again led her over to the pillow on the floor. He got her down on her knees and said that she now had to suck each guy off until they came and swallow his cum. Even though Ann was swallowing my cum more often and had swallowed on her first two trips I could tell from the look on her face that she was not in love with the idea of having six loads of cum go down her throat and into her stomach. Will said that six loads of cum were enough for a cocktail and that Ann should collect the cum and save it in a glass until all six of the guys had cum and then drink it all down at once. Upon hearing this I thought that Ann was going to spring up off of the pillow on which she was kneeling but Tony had his hands on her shoulders and kept her in place. The rest of the guys loved this suggestion and one of them got a water glass from the other room. Teaching My Wife Ch. 03 Ann was horrified by all of this but Tony would not let her up and soon Bob stepped in front of her and stuck his cock in her face. Ann decided that she should start sucking while she tried to figure a way out of things and took Bob into her mouth. Bob eventually came in Ann's mouth and Tony gave her the glass and told her to spit it out. She did and the next guy stepped forward and the process was repeated. I could not help but think how ironic it was that Ann who normally did not like to swallow and spit out my cum for years was now being forced to save what she spit out in order to swallow it later. After a few more loads in the glass, later came. Ann looked absolutely aghast when she handed the glass to Tony after she had spit out the last load of cum. The bottom inch or so of the glass was filled with a mixture of cum and Ann's saliva and it really was a slimy gooey mess. Tony put the glass on the desk and helped Ann to her feet. He led her over to the desk, pointed at the glass, smiled and said, "Bottoms up." Ann started to shake and whine and finally blurted out, "I cannot swallow that much cum at one time. I will get sick." "Either you swallow it yourself or we will hold you down and pour it into your mouth," Tony said. Ann continued to beg and plead and looked for all the world like a trapped animal that knew its fate was at hand. Tony was unmoved by her pleas and said, "Last chance to do it yourself." Ann reluctantly picked up the glass and with shaking hands put it to her lips twice but could not bring herself to tip it up to start the cum flowing into her mouth. She put the glass back down on the desk and broke down sobbing saying, "I can't, I can't." Tony nodded to the rest of us and we went over to Ann and surrounded her. Hands reached out and grabbed her. She tried to squirm away but had no where to go. She was led over to the bed and laid on her back. Hands held each of her limbs and Will knelt over her head and held her head in place with his thighs. I was holding her right leg and had a clear view of what was happening. The glass with our cum was placed on the nightstand by Tony who then told Ann, "Open your mouth." Ann clamped her lips shut and struggled harder than ever but being held by five men she was unable to get anywhere. Tony suddenly realized that unless Ann cooperated it would be hard to get the cum into her mouth without spilling a lot of it. Tony went to his briefcase and came back with two one inch binder clips. He showed them to Ann and said, "I will put these on your nipples and leave them there until all of that cum is in your belly." Ann's eyes opened wider than ever and you could see the look of fear on her face. "Well, are you going to swallow that cum?" asked Tony. Ann stayed silent except for some quiet sobbing. "OK, we do it the hard way." Tony picked up one of the clips and put it on Ann's right nipple. Will covered her mouth with his hand to muffle her screams. Tony waited about a minute and then put the other clip on her left nipple. Will kept his hand over her mouth as Ann continued to shriek in pain. After a few minutes she started to calm down and Tony reminded her that the clips would stay on until she swallowed the entire glass of cum. Ann knew from experience in our play sessions with various nipple clamps and clothespins that the pain would continue to grow the longer the clips were left on and that it would double when the clips were removed. She knew that she had run out of choices and time. Ann forced herself to calm down and when Tony saw this he nodded at Will who took his hand off of her mouth. "OK, you win dammit, I will drink it because my nipples are killing me," Ann cried out. We let go of her and she sat up on the bed by the nightstand where the glass of cum was sitting. Ann shakily reached over and took the glass in both hands. We could see the revulsion on her face as she lifted the glass to her lips and tipped it into her mouth. We watched her throat move each time she swallowed and saw the glass getting empty. After six swallows, she was done. Ann dropped the glass on the bed and immediately took off the clip on her right nipple. She started to rub it vigorously for a few moments and then took off the clip on her left nipple and did the same. We gave her a few minutes and then Tony said, "We will keep the clips handy just in case we need them again." He picked the clips up off of the bed and put them on the nightstand. We let Ann go to the bedroom bathroom to freshen up and we used the one next to the sitting room. When everyone had once again assembled in the sitting room Tony read the second item in the letter and sort of smirked at Ann when he finished saying, "You will probably like this part better." Ann knew that she would because the letter said that she was going to be fucked in whatever combinations the guys wanted. She had not had an orgasm thus far and was extremely horny. Ann walked out of the sitting room and into the bedroom, laid down on the bed on her back, drew up her legs and spread them open. Ann later told me that even though she had said that she had the same equipment as the girls in the gang bang videos she had watched that once she started doing things with the guys she was concerned about whether she could take six guys but she knew she really no longer had a choice. Ann said that she was extremely horny by this point and needed to get fucked. She was also worried about having the clips used on her again if she refused to do what the guys wanted. Will won the race to the bed and slipped his condom covered cock into Ann and started to fuck her pussy hard. Ann responded almost immediately and within a minute was fucking Will back as hard as he was fucking her. About 30 seconds later Ann exploded in what would be the first of many orgasms. One thing that neither Ann nor I had thought about when deciding for her to have sex with more than one man was that her pussy became very sensitive after she came and most of the time I would have to stop fucking her for a few seconds or longer after she came. I realized while Will was fucking her that there would be no breaks for Ann tonight and saw Will keep pounding away after Ann's first orgasm. I think Ann realized it too as her eyes rolled back in her head and she started to come again. By the time the third guy was done fucking Ann she had a dreamy distant look on her face that did not change much even when she came and she came often. She later told me the sensations were almost excruciating as the walls of her cunt became extremely sensitive and stayed that way as one guy after another kept on fucking her. The only time her super sensitive pussy got a break was when she was fucked in the ass. In the first round, Will, Gary, Cliff and Tony fucked Ann in her pussy while Bob and I fucked her ass. As the sixth guy crawled off of her Ann thought that she would get a break but looked up and saw that Will, Tony and Gary were ready to go again. Will lay down on the bed on his back and told Ann to get up on his cock. She got his cock wedged into her well fucked pussy and they got a nice rhythm going. Will pulled her down so her chest was against his and held her. Meanwhile Tony had lubed up the condom on his cock and had gotten up on the bed. He lined up with Ann's ass and pushed into her in one stroke. "Oh my God," Ann cried as she experienced for the first time a cock in her pussy and her ass at the same time. She established a good rhythm with Will and Tony and a minute later she was airtight as Gary got in front of her and fed her his cock. They fucked this way for about five minutes before first Gary, then Will and finally Tony came. Ann later told me that she was too tired from all of her earlier orgasms to have much more than a small tremor during her triple penetration but that nevertheless she had enjoyed it. For those of you who want to know, "Yes she did swallow Gary's cum." She said that for the rest of the night she was going to swallow anyone and everyone because she did not want those binder clips anywhere near her again. Bob and I got on the bed next and positioned Ann on her hands and knees. He put his cock in her mouth and I thrust into her pussy. She looked so sexy being spit roasted by the two of us. "Let's make her do the work," Bob said and we positioned ourselves so that when my cock was fully in her pussy Bob's cock would be almost out of her mouth. When she moved forward my cock would partially withdraw and Bob's would go deeper into her mouth. Because we had both come twice already we had good stamina and Ann had to work for a long time to get us off. She grunted and groaned as she pushed herself back and forth and had a couple of nice orgasms along the way. Her body was eventually covered in a light sheen of perspiration because of her exertions. Bob and I finally came and Ann swallowed another load. That left only Cliff who had not fucked her a second time and he laid down on his back and told Ann to get up over him. She started to lower her pussy down on his erect cock and he said, "No, put it in your ass." Ann shifted forward a bit and after a try or two to correct her aim had Cliff's cock firmly seated in her ass. "Now, fuck me hard." Ann started to push herself up and down on Cliff's cock. She grunted and groaned and moaned as she speared her own ass over and over again with Cliff's raging erection. Cliff too had come twice already so his stamina was impressive as well. Ann moved up and down, up and down on his cock for almost twenty minutes before Cliff finally announced that he was coming. When he was finished Ann rolled off of him and collapsed on the bed. Her body glistened with perspiration from her workout and her crotch area was damp and slimy from her own secretions and the lube that was used on her. Everyone was pretty fucked out by this point, especially Ann, and we all fell asleep. I lay down next to Ann on the bed and Cliff was on her other side. The rest of the guys fell asleep on several of the chairs and couches in the sitting room. I was startled awake by Tony yelling,"Fuck, it is already 11AM." He, Bob and Cliff had to be at the clubhouse for their golf outing by noon so there was a flurry of activity as they hastily got dressed and got their stuff together. Gary and Will also had a lunch meeting set for noon so they joined in the frenzy. I was disappointed because I had hoped for another session for Ann in the morning but that was not to be. It was, however, a kinky sight to see Ann standing there naked with all five of the other men fully clothed and me in one of the hotel robes. Even though she looked totally fucked out she still looked sexy as hell. Each of the guys kissed her deeply and took a final opportunity to fondle her tits and pussy. Bob said to Ann, "I left one of my business cards on the night stand in case you ever get to my hometown and want to get together again." The other guys thought this was a good idea as well and fished cards out of their pockets or briefcases and put them with Bob's card. This got my mind spinning with the future possibilities. The last two guys finally left and the door had no sooner clicked shut when I grabbed Ann and kissed her deeply. I led her to the bed and fucked her. I did not make love to her, I fucked her and she fucked me back just as hard. We lay in bed after that and snuggled and talked about her just completed adventure. Ann said that although there were parts that she did not like, guess which ones, she had never been fucked so hard and for so long and understood why many women who have been gang banged liked it so much. Ann went to shower and when she came out she started to get her stuff together. She picked up the business cards from the night stand and put them in her purse. She turned and started to walk away. "You forgot the clips," I said. Ann gave me a startled look followed by a small smile. She turned back to the night stand, picked up the clips and put them into her purse as well. Teaching My Wife Ch. 04 WARNING--This is a loving wife story meaning it is about a married woman who has sex with men other than her husband. If that is not for you then please move on and spare me the comments about how you respect your wife too much to have similar things happen to her, etc. I always get a good laugh out of guys who post the wife respect stuff but are reading porn (which generally objectifies women) on the internet, especially porn of the loving wives variety. Although this is a multi-part story the chapters are largely self contained and it is not absolutely necessary to have read the previous chapters before reading this one although reading the earlier chapters does give you the best background. This is the story of how my wife Ann, who used to be sexually adventurous, became more and more conservative and how I set out to change things back to and beyond where they were. As I described in the first chapter, over the years Ann had become more plain vanilla as far as sex went. The adventurous woman I loved so much had seemingly left the building along with Elvis. * I told Ann that she needed to be taught how to once again be a whore in the bedroom. The words "whore in the bedroom" were hers as shortly after we were married she told me that she always thought the ideal wife was a lady outside of the bedroom but a whore in the bedroom. Because Ann had over the years pulled back the sexual boundaries we once had I told her that these lessons would be at the hands of other men. I knew that if we tried to become more adventurous and Ann objected to something that I was doing to her that I would slow down or stop because I loved her while a stranger would likely not stop and say something like, "Come on, baby, you can do it." Ann would not be as free with a stranger to impose her boundaries and would be taken beyond those limits. Because Ann went out of town for three or four days at a time in her job about every six weeks we decided that her lessons would be during these trips. I would pack her a kit of the items to be used for each lesson along with a video camera and an instruction letter she was to give the man or men she selected. So as not to interfere with her job, Ann would extend her trip for an additional night at our expense and tell her company that an old college friend, relative, etc. lived in the town she was visiting. The additional night would be lesson night. On each of her first two trips Ann engaged in activities with other men that we had done together earlier in our marriage such as having her pussy lightly flogged to orgasm, filling her ass and pussy with ice and then getting fucked after it melted, anal sex, having her ass and pussy stuffed with inflatable toys that were then inflated beyond her previous maximums, being fucked with a porn star sized vibrator and plain old fucking and sucking. Ann was also exposed to a room service waiter by one of the men and forced to endure being groped and fingered by him to orgasm. She also swallowed more cum than she had in a long time with me. On her third trip she was the center of a six guy gang bang with me as one of the six. We originally planned on only three guys, one of them me, but events got out of hand and Ann really made up for lost time as this was her first experience with more than one man. For more, see Chapter 3. Ann and I had talked a lot about what happened on her first three trips and watched the videos she brought back numerous times. It was a terrific turn on for both of us but we realized that we had been risky in what we had her do with strangers on the first two excursions and lucky that none of them had harmed her. Ann admitted that she was scared at times during each of the first two encounters but said that the fear in her stomach had actually turned her on more than she would have normally been. She also said that she now realized that it was best to have strangers with whom she had no prior relationship do her training because she understood how easy it was for her to say "stop" or "slow down" to me. As Ann experienced in her first three sessions, strangers did not listen nearly as well to "stop" or "slow down." We also talked a lot about what happened on her third trip even though I was there. Ann said that she enjoyed being the center of attention with a group of guys working her pussy, ass and mouth over. She did not enjoy drinking down a glass with six loads of cum in it or having binder clips put on her nipples to motivate her to do so. Ann even said that despite having the walls of her pussy get super sensitive after she came having the guys who were fucking her keep on going caused her to have stronger secondary orgasms than she usually had. Those of you who read the earlier parts will remember that whenever Ann had a major orgasm she usually had a series "after shocks" and that her pussy became extremely sensitive after she had come for the first time. Ann said that she knew that the guys who were fucking her during her adventures would not stop so she forced herself to just lie back and take it. She said that having her super sensitive pussy continually fucked led her to have one major orgasm after another. Ann had obviously learned something because whenever I fucked her after her gang bang I did not have to pause like I used to after she came and just kept banging away at her wet pussy. Ann came like gang busters and kept coming as I continued fucking her. We talked a lot about how she felt emotionally and Ann said that at first she was very hesitant about picking up a stranger for sex but that she got over her hesitation because I was helping to arrange things and she had my approval. She also quickly saw that I was right that a stranger would better push her limits and that she had learned the difference between making love and fucking. Finally, she admitted that it was a turn on to be able to pick up good looking men because as she grew older she thought that she was not as attractive or sexy as she was when she was younger. Her experiences had definitely transformed Ann into a better lover and our sex became hotter as I did not have to hold back as I sometimes did in the past. Ann had even agreed to swap and we had already traded partners with a few couples we met at a local club. No orgy, just she with the husband and me with the wife. Once in separate rooms and twice in the same room. Because of these experiences Ann was definitely returning to the sexually adventurous woman she had been earlier in our marriage. We talked about whether we should stop for a while and see how things went. We decided that with our swapping activities that we would just slow down and not arrange a "lesson" for Ann every time she went out of town. After her second trip without a lesson Ann told me that she missed the anticipation and trepidation she felt in the days before one of her out of town adventures. She also admitted that she had gotten off being used by strangers for their pleasure and often not knowing in advance what they were going make her do or do to her. On a few occasions during our marriage I had thought that I had detected signs that Ann could have a submissive side to her personality. When I tried to explore this she never really wanted to talk about it or otherwise go there. Perhaps her sessions with strangers had allowed this aspect of her personality to come to the surface because she allowed herself to be put into situations where someone else was in control of what happened to her. The more I thought about it the more I became convinced that Ann had a submissive side to her and where things had gone wrong was when I had talked about it in terms of her being "submissive" or being a "slave." Whenever I suggested to Ann that we do something where I would be in control and used the wrong words she would object and refuse to go along. I found that if I tried submissive scenes with her without labeling them as such I had a better chance of having her go along. So far I had gotten things right on this level when setting up Ann's sessions with strangers and filed this away in my brain to be sure that I would remain cognizant of this going forward. When Ann told me she missed not having a lesson on her last two trips I suggested that she could just pick up a guy on her own. She said that she had thought about that but that there was something about the planning and preparation of her previous sessions that turned her on more. She said she knew that by adding a day onto her trip that she was setting aside time for sex and would get a tingle in her pussy when she told her assistant to arrange for the extra night in the hotel. Ann said that the tingling would continue when she put the toy kit I had prepared into her luggage along with her garter belt, hose, short skirt, CFM heels and other "hunting" clothes. She said her pussy would also tingle when she put the letter I had prepared for her into her purse. Apparently anticipation was a big part of the appeal of her sessions to Ann. Because it was now apparent that there would be another lesson in the near future for Ann we talked further about how to make that happen. Ann said that she liked it better when she was not permitted to read the letter or look in the toy kit until her training session actually started. She said that before her second and third trips not knowing what was in the letter left her almost constantly wondering about what was going to be done to her. She admitted that she had even fingered herself to an orgasm a few times after her pussy grew wet from her pondering the mystery of what would be done to her in the near future by a man or men she had never met before. Ann's next trip was coming up in about three weeks so I set about coming up with what to put in the letter. I thought about having her pick up a woman but as one of the wives we had already swapped with was bi I thought that there would be an opportunity there later. I thought about the first three sessions and saw that Ann had been worked over pretty good in the first two and her first gang bang, with six guys, would also be hard to top. Time was running out and I still did not have a solid idea of what to put in the letter. As it were, fate would intervene and an opportunity would drop into my lap. I was working at our home pc and I noticed Ann's itinerary for her upcoming trip on the desk next to our computer. When I saw the name of the hotel I had my answer. I had stayed at this hotel several times in the past few years and knew that they had a very nice indoor pool with a separate hot tub area. In addition, the hotel kept the pool open until midnight and even turned down the lights to give it a more intimate feeling. I thought that in this day and age of lawsuits about everything that they would be worried about a guest who had had a few too many drowning but they had it posted pretty well with signs that there was no lifeguard on duty and they even had a small sign at the front desk saying the same thing. The health club was also next to the pool and there seemed to be some activity there most of the time with people coming in and out and there was an attendant at the club desk close enough to the pool to hear any loud commotion. When I had stayed at this hotel I had used the pool late one night and was surprised to hear and see a couple having sex in the hot tub area. The hot tub area is separate from the pool and had some potted plants and smallish room divider screens between it and the main pool that screened it from full view from the pool but they did little to conceal what was happening. As soon as I learned that Ann would be staying at the same hotel I knew that the letter I wrote for her would have her fucking by the hot tub. I had thought about having Ann also take the video camera we used on her previous adventures but decided it would be too cumbersome for her to try to use it in various areas around the pool and hot tub. I had a better alternative anyway. A few years earlier when I had first stayed at this hotel I was having a drink at the bar. One of the other patrons had apparently had too much and was getting pretty loud at the other end of the bar. I heard the bartender tell him that he could not legally serve him any more because he was already drunk. This really pissed the guy off and he started banging his fist on the bar and yelling, "I want a goddamn drink." The bartender again refused and started to walk away from the guy. Suddenly the guy reached across the bar and grabbed the bartender and tried to pull him over the bar. One of the waiters saw what was going on and stepped in to try to intervene. The guy let go of the bartender and sucker punched the waiter flush to his jaw dropping the waiter to the floor. With the waiter on his hands and knees trying to get up the guy started to kick him violently to the ribs. It only took me a few seconds to get off of my stool and get down to where the guy was. I pulled him by the shoulder and when he saw me he swung wildly. As I was expecting it I was able to step out of the way unlike the waiter who never saw the punch coming. The guy lost his balance from the missed swing and as he was falling toward me I landed a solid right to his stomach. He doubled over and as he started to try to stand up again I landed a left on the side of his head that put him on his knees. I was on him quickly and pushed him down to the floor. I twisted one of his arms up behind his back and told him to calm the fuck down or I would break it for him. Not that I am that macho but I had some experience in boxing in a local PAL when I was growing up and still got to the gym to work out once or twice a week. Hotel security was there a minute later followed a few minutes later by the cops. They took the drunk into custody and as they led him away he started to yell that the cops should arrest me too because I had assaulted him. Even though the bartender and waiter backed up my story of what had happened I started to get nervous when two of the cops again asked me to tell them what had happened. I started to repeat my story when one of the hotel security guys came over and introduced himself to us as the head of the hotel's security. He then said, "Officer you do not have to ask what happened, you can see for yourself." He said that the hotel had cameras in all public areas and that he would show them the video of what had happened in the bar. He led us out of the bar, through the lobby and down a hall to a door labeled "Hotel Security." We went into what was a pretty sophisticated control type room with about ten monitors displaying various areas of the hotel. He sat down at the control panel, flipped a few switches and played the video of the bar incident on the center monitor which was larger than the others. When it was over the cops said that I was in the clear and free to leave. They also asked the hotel security guy not to erase the tape as the prosecutor would likely want it as evidence. The cops left and the hotel security guy extended his hand to me and said, "Thanks for what you did. The waiter that the drunk was kicking the shit out of is my nephew. I got him this job for the summer and my sister would not be happy if I let something happen to him as she thought he should get an office type job." We finished our introductions, his name was Jack Williams, and he said, "I noticed you never got to finish your drink, let me buy you another." Well, one turned into a few and Jack and I spent the next two hours talking and drinking. When we called it a night Jack thanked me again and said to let him know if he could ever do anything for me. Jack also apparently put me on the VIP list of the hotel because after that whenever I stayed there my room would be automatically upgraded and I would get coupons for free breakfasts and drinks and other perks. On two other occasions when I stayed at the hotel Jack must have noticed my name on the guest list and invited me for drinks. I would not say that we were friends but we were getting close. I realized that my knowing Jack made this the perfect set up for Ann. Jack could keep an eye on things remotely to make sure the guys who would be fucking Ann did not get out of hand. He would be able to video tape Ann's adventure for me and he would be able to keep Ann from getting thrown out of the hotel or arrested in case anyone complained about people having sex by the hot tub. My plan in place I picked up the phone and called Jack. He immediately took my call and we chatted a bit and then I said, "I have a favor to ask." As Ann and I wanted to keep her activities as anonymous as possible I did not tell Jack that Ann was my wife. Instead, I explained to Jack how there was a group of guys I hung around with to watch football at a local bar on Saturday afternoon. I said that there was also a woman who often watched with us and that over the years we had started to put some side bets on the games. The woman actually knew football pretty well and wound up winning more than she lost. I said that the woman was also not a gracious winner and took every opportunity to rub it in whenever she won. Anyway, I continued, "One Saturday the woman had a very bad run of luck and wound up losing a couple of hundred dollars to each of the guys in our group." Turns out she did not have enough to pay off her losses and eventually one of the guys suggested that she could work it off on her back. She said, "I am not going to fuck you guys, I know you and have to look at you." We guys reluctantly agreed and said if she did not want to fuck us then she could fuck strangers. Although we would have enjoyed fucking her we thought that having her brought down a few pegs by fucking strangers to make up for all of the crap she gave us when she was winning would be worth it. "What does all of this have to do with me?" Jack asked. I told Jack that we wanted the woman to have to fuck guys by the hotel hot tub so that he could video it for us and also keep an eye on things so she would not be hurt. Fucked, yes, hurt no. Jack laughed and said, "Yea, I can do that for you." "What does this woman look like anyway?" Jack asked. I described Ann saying she was 5'2" tall and weighed 115 pounds. She has brown eyes and medium length brown hair that at times looks reddish in certain light. Her skin is very pale and she has a lot of reddish freckles on her tits and shoulders. Her breasts are a natural B cup topped with light brown/pinkish nipples which get about a half an inch long when she is aroused. Ann has a very, very thin waist which gives her a classic hourglass figure and an ass to die for. Jack said, "Hmmm, I wouldn't mind having a go at her myself." "Go ahead," I said, "She has to stay by the pool for three hours and do anything a guy asks her to do. The only rules are that the guys have to wear a condom when they are in her pussy or ass and cannot do anything that would permanently mark or hurt her." "Damn that sounds inviting," Jack said and we both laughed. Although tempted Jack said, "It would not be a good idea for the head of security to get caught with his pants down so I will have to pass and just watch." I gave him the details about when Ann would be staying at the hotel and we hung up. With everything set at the hotel it was time to write the letter for Ann. The letter I gave Ann read as follows: "Tonight we are changing things up. You are not going to give a guy you pick this letter. This letter is for you. Look in the toy kit in your luggage. You will find scissors, a razor and shave cream. The first thing you are going to do is to shave your pussy bare. I know you have done this in the past for me on a few occasions but tonight is the start of you keeping your pussy trimmed and shaved going forward. Teaching My Wife Ch. 04 Put this letter down and go and shave yourself so that your pussy and ass are free of any hair. When you are finished come back and read the rest of your adventure. Now that you are reading again your pussy must be bare and smooth. Look further into the kit and you will find one of your more revealing bikinis modified to make you even more exposed. I have cut out the linings in the bra and bottoms so that now when you get the suit wet all of your charms will be clearly visible. Get dressed in your bikini, put on the hotel robe along with your CFM heels and go down to the pool. Be sure to take the tube of sex lube and the condoms with you. Get your bikini wet and come on to any guys that are in the pool or hot tub. Tonight you are going to fuck in public. Anyone who is around will be able to hear your moans of pleasure and to see how you writhe and buck as your pussy and ass are filled and used. Once you are naked you are to stay that way and you are to remain in the pool area for the next three hours. You cannot say "no" to anything anyone wants to do to or with you except for the rule about condoms or anything that would permanently mark or injure you. If anyone asks why you are doing this tell them that you lost a bet and have to make yourself available to whomever for whatever for three hours at the pool to pay it off. You have a hot body and know how to use it. Tonight you will use it in a more public way than you have before." Ann was never an exhibitionist and she would always get embarrassed whenever she inadvertently exposed anything interesting. Those of you who have read Chapter 2 will recall how she got red with embarrassment when the guy she was with forced her to stand naked before the room service waiter and let him finger her to orgasm. If things went according to plan, Ann was going to be exposed to who knows how many people and her boundaries were really going to be pushed further out and in a new direction. I knew that Ann would not expect public sex and I was right as when she returned home she said, "I can't believe you set it up so I would be fucked in public." I asked her to tell me about her adventure even though I would be getting the tape from Jack and Ann told me how she had shaved her pussy bare and said that she thought that I would have one of the guys she was with do that. She told me how she trembled when she resumed reading the letter and learned that she was going to be on display and would be fucked publically. Ann told me how a part of her wanted to slip away but another told her that she had to go through with it. She told me how she had fingered herself while putting on the bikini and knew that the wetness between her legs gave her no choice but to go through with the adventure I had planned for her. She recounted how she had walked down the hall to the pool on her CFM heels wearing only her bikini and hotel robe with condoms and a tube of sex lube in her pocket. Each click of her heels on the tile floor seemed to resonate loudly like a clock ticking down the seconds until her next adventure began. Ann said that she felt her pussy getting wetter and wetter both with the anticipation and trepidation of what she was about to do as well as the added sensations from having just shaved herself smooth. With the linings removed from her swim suit Ann worried that her juices would make a telltale wet spot between her creamy thighs and that as soon as she took off her robe everyone in the pool area would know how hot she was. When she arrived at the pool there were two guys swimming laps and Ann slipped off her robe and heels and went into the pool. The water was cooler than she expected and her nipples hardened immediately. With the lining gone from her bikini top her hard nipples stood out boldly and it was not long before one of the guys swimming in the pool came over to her and struck up a conversation. After a few minutes Ann remembered that she was to be the aggressor tonight and slid her hand down and cupped the guy's dick and said, "The water is cold; let's go over to the hot tub." They walked over to the hot tub and the guy took Ann into his arms and kissed her deeply. Ann stood silently with her arms at her sides as the guy untied her bikini top and exposed her still hard nipples. He ran his hands over her tits and down her torso stopping only to hook his thumbs under the sides of her bikini bottom. In one smooth move he slid that garment down her legs and let it drop to the floor. Ann stepped out of her bikini panty and kicked it aside. She was now naked in a public place in front of a guy she had just met and whose name if he had mentioned it she did not remember. Ann said that she was in almost a trance like state with her mind and emotions swirling. The sound of more people coming in to the pool area broke her spell and she recalls looking over to see how many more people would likely see her in all her nude splendor. Ann recalls glancing at the clock on the wall and noticing that it was a quarter to nine. You could see Ann shudder as she thought," Oh, my God, I am going to be naked here in public until nearly midnight." The guy she was with got her attention with some gentle pressure on her shoulders and Ann slowly sank to her knees. The guy ran his hands through her brown tresses and then held her head firmly as he aimed her mouth directly at his now hardening cock. Ann reached up and pulled his swim trunks down and looked up at the first cock that would be inside of her tonight. Ann started by licking the head and underside of his cock before sucking it into her mouth. Even on the video from the hotel "spy" cameras you could make out some slurping sounds as she worked on the guy with her mouth. Ann was just getting a good rhythm going with her head bobbing up and down on the cock in her mouth when the guy again put his hands on the side of her head. "Time to take it all honey," he said as he pushed the whole length of his cock into Ann's mouth and into the beginning of her throat. Later Ann told me that even though she expected him to do that she was caught a little off guard and gagged and sputtered until she got used to the fullness in her throat. From her previous adventures Ann knew that strangers would use her mouth and force their cocks into her throat when they were ready and not when she was ready as happened when we made love. After a few more minutes of sucking the guy was clearly ready to fuck Ann. He helped her to her feet and went over and got one of the chair cushions that he put on the floor next to where Ann was standing. "Lie down," he directed. "We have to use a condom," Ann said, "I have some in the pocket of my robe over by the pool." You could tell that Ann was expecting, or at least fervently hoping, that the guy would go and get her robe. The guy looked at her sternly and said, "Look, baby, you are going to get fucked. If you want it to be with a condom then you are going to have to go and get them." Ann looked over at the pool area and could see that there were now about five or six guys using the pool. Because her instructions were that once she was naked she was to stay that way for the next three hours she knew that she could not put her swimsuit back on. While Ann was trying to figure out what to do the guy had gotten down on the cushion and he started to pull her down on top of him. Ann pulled her hand away from his grip and said, "We have to use a condom." "Then you better go and get one," the guy said. Ann's shoulders slumped as she slowly exhaled. She collected herself and then took what she later described as the longest walk of her life. Even though she had been naked when she sucked and fucked and more in her previous sessions and had even been exposed to a room service waiter this was very different. She was now going to have to parade her nudity before five or six guys who she had never met before let alone seen before. Ann slowly turned and started to walk towards the pool area. She emerged from behind the potted plants and light screens that separated the hot tub from the pool and had taken only a few steps when one of the guys in the pool saw her. "Well, all right," he yelled and soon five more pairs of eyes were feasting on her body. "It felt as though their eyes were burning me." Ann later said. Ann continued over to where she had left her robe, picked it up and walked back to the hot tub area. As she rounded the corner spontaneous applause broke out from the guys at the pool. "Sounds like you have some admirers," the guy who was waiting for her said. As she knelt down to join him on the cushion on the floor, Ann said that she suddenly realized how wet she was. She said that her pussy was so wet that she had even leaked a little onto the tops of her inner thighs. Apparently her exposure and concomitant humiliation had triggered a positive response in her nether regions. The guy was lying on his back on the cushion and she handed him a condom and he put it on. He helped her climb on top of him. Ann took his cock in her hand, lined it up with her pussy and slowly sank down. She was amazed at how easily he slid in but was not surprised because she knew how wet she had become. They fucked slowly at first and Ann bit her lip several times because she did not want to be vocal and attract even more attention from the guys at the pool. She was successful for a while but as the fucking increased in intensity the first moan escaped her lips. As she continued to ride the guy's cock she got closer and closer to what she knew would not be a silent orgasm and Ann grew more and more vocal. Like many women, Ann usually keeps her eyes closed when she has sex and tonight was no exception. At one point she opened her eyes and was startled to see that she now had an audience. The guys from the pool had heard them fucking and came over to get a better look. "Again, I could feel their eyes burning through me," Ann said. This time, however, her embarrassment lasted only for a few moments because she was rapidly getting close to a mind blowing orgasm. Ann said that it was like someone had flipped a switch in her brain because she went from being embarrassed one second to feeling like a porn star the next. I thought to myself Ann said, "You want to see fucking, I'll show you fucking." She started to really pound the cock she was riding and screamed when she came for the first time, collapsing onto the guy's chest. The guy, however, had not made it and after a few seconds said to Ann, "Get on your hands and knees, I want you doggie style." Ann arranged herself on the cushion and the guy got behind her. He said, "Put it in," and she reached through her legs and guided him home. When he was in to the hilt the guy said, "Now show me how hard you can fuck." Ann started to push herself back and forth on the guy's cock. Ann had not fully come down from her orgasmic high and it did not take long before she was approaching her second climax. She shuddered as she came but did not stop fucking herself back on the guy. She came a third time before the guy grabbed her by the hips, gave her about six good thrusts and came deep inside her pussy. They sort of fell onto their sides together with the guy still inside of her. A minute or two later Ann opened her eyes and saw that the audience had dwindled to only two. Apparently the other guys had thought that Ann and her companion were exhibitionists and not that she was there to take on all comers for the next three hours. The guy Ann had just fucked got up and put his swim trunks back on. He went over to where Ann was still laying on the cushion, knelt down and gave her a deep kiss. "You were great, babe," he said. "I hope I run into you again someday." This was all the two guys watching needed to hear and they soon were kneeling on the cushion on each side of Ann. They were still somewhat reserved and one of them asked Ann, "Are you interested in some more fun?" "I don't have a choice," Ann replied. "What do you mean you do not have a choice?" Ann then gave them the story about how she had lost a bet and that her forfeit for not being able to pay was to stay at the pool and fuck anyone who wanted to have her for three hours. She looked over at the clock and said, "And I still have almost two hours to go." The two guys were on her in a flash and Ann had hands on her tits, fingers twisting her nipples and other fingers invading the two openings of her crotch. She was starting to get quickly turned on again because she had still had not had that much experience with multiple partners and having more than one pair of hands and more than one mouth working on her soon had her writhing and moaning. The guys got Ann up on her knees, stripped off their swim trunks and presented her with their cocks. She licked and sucked one and then the other, going back and forth between them. Because the guys were already turned on from having watched Ann fuck the first guy they were soon close to cumming. The guy whose cock she had in her mouth said, "Here it comes," and thrust deep into Ann's mouth and fired off five or six shots of cum. Ann struggled to keep up but was able to swallow his load. The first guy had no sooner finished when the second guy pulled Ann's mouth onto his cock and fed her another load. She swallowed his load as well. After the two guys left Ann was alone so she slipped into the hot tub to relax. She must have fallen asleep because she said she was startled by the sound of a guy getting into the other side of the hot tub. "Hope you don't mind if I join you," he said. "The more the merrier," Ann replied. After a few minutes the guy's eyes adjusted to the light and he could finally see through the steam rising from the surface of the water that Ann was naked. They made small talk for a few more minutes and the guy periodically would adjust the jets and other controls on the tub, each time moving closer to Ann. When he saw that she was receptive he moved closer and sat next to her. He put one of his hands on her left thigh and slowly slid it up towards her pussy. When he got there he realized that Ann's pussy was shaved and he said, "I love women who shave themselves bare." He continued to rub his hand around Ann's pussy and she started to respond to him. They kissed a few times and then he said, "I just have taste you." He positioned Ann on the ledge of the tub and he remained in the tub. He put Ann's feet on his shoulders and went to work. He nibbled on her clit and stuck his tongue inside of her as deep as it would go. Normally Ann takes a while to warm up from having her pussy eaten but not this time. She said she was not sure whether it was because she had just shaved, because she was letting a stranger do it, because they were in a public place or all three. It only took the guy about five minutes before Ann was clenching her fists and pounding them on the deck next to her. Only seconds later she erupted in a blistering orgasm and a minute later had another, harder climax. They guy let Ann rest for a minute and when she opened her eyes said, "That is my favorite thing to do to a pretty woman." Ann smiled and said, "And what is your second favorite thing?" "To fuck them in the ass," the guy replied. Ann took the guy by the hand and led him over to the cushion that the first guy had put on the floor. She got a condom and the lube out of the pocket of her robe and laid them next to the cushion. Ann then got down on the cushion on her hands and knees and lowered her shoulders and waited. She did not have to wait long. The guy lubed up her ass and then worked one, two and finally three fingers into her. He spent time getting her comfortable and ready and Ann said that he was so gentle that he was almost like a lover. When she was ready the guy slipped on a condom and lined his cock up with her ass. In one hard, arrogant thrust he was buried balls deep in her ass. Ann yelped a little as she realized that gentle was apparently over. The guy fucked her ass mercilessly pounding her so hard that she had to strain to hold her ass up position. He had good stamina so Ann's ass took a real beating. The good news for Ann was that he also started to finger her clit and she began to feel the warmth of an approaching orgasm spreading through her pussy and ass. Finally, Ann reached the breaking point and cried out, "I'm coming." "So am I," the guy responded and gave one huge thrust pushing Ann down onto the cushion as he came deep in her ass. He was gone a few minutes later and Ann was again left alone. She got back into the hot tub to sooth her freshly fucked ass and just soaked. No one else came to the pool for the next 20 minutes and when Ann next looked up at the clock she realized that the three hours were up. She got out of the hot tub, retrieved her bikini and put it on along with her robe. She walked out to find her CFM heels and when she had them on walked down to hall to the elevator and went up to her room. She took a hot shower and climbed into bed. Ann went to sleep thinking her adventure was over but that would not be the case. It was the next morning when Ann was packing her things and getting ready to check out when there was a knock on the door to her room. As she was not expecting anyone she asked who was there and heard "Hotel security" in response. She looked out through the peephole in the door and saw a guy standing there in a blue blazer with the hotel logo on the pocket. Ann opened the door and the guy introduced himself as Jack Williams, Head of Hotel Security. He asked if he could come in as he had something to discuss with her. Since he looked official and presented himself well Ann said "OK" and opened the door fully to let him into her room. Jack explained that the hotel had a sophisticated system of monitoring cameras throughout the facility that were used to keep an eye on things to insure guest safety including several in the pool and hot tub area. He said, "You put on quite a show last night." Ann blushed knowing that not only had the people at the pool watched her performances last night but so had this guy and who knows who else. Jack reached into the pocket of his jacket and pulled out a video tape and laid it on the desk. "I thought you might want a copy of your trysts last night. Oh, and don't worry, I kept a copy as well," Jack said to Ann. He let this sink in for a while and then said, "I damn near came in my pants last night watching you get fucked in the ass. My wife is not in to that kind of stuff so it has been a long time since I got a chance to tap some prime ass. So, here is the deal. You let me fuck your ass now and every time you stay at this hotel in the future and the video tape copy I have will stay in a safe place." "Look at it this way," Jack continued, "you said last night that you did not have a choice because you were paying off a bet so let's say that you do not have a choice now either. Or should I just send a copy of the tape to and he named her company?" "If you saw what happened last night then you know my ass is too sore to take you that way right now," Ann whined. "Sore or not, you know my terms," Jack replied. "Please, no," Ann begged. Jack got up off of the bed and said, "I gotta get going because the mail pick up is in about a half an hour." He was half way to the door when Ann cried, "OK, you bastard, you can fuck me in the ass." Jack returned to the center of the room smiling and said, "Get the lube and get yourself ready." Ann slowly padded over to the nightstand and pickup up the tube of lube and a condom. She took off her nightshirt and stood naked in front of Jack before getting on the bed. Ann squeezed out a dollop of lube and slowly started to work it into her ass. First one finger and then a second. She tried for a third but could not bring herself to stretch her poor abused ass that much. Teaching My Wife Ch. 04 Jack watched her intently and then started to get undressed. He stripped off his blazer, shirt and tie and then his shoes and socks. He stood close to the bed where Ann was preparing herself and took off his pants and underwear in one fell swoop. Ann looked between his legs and said, "Oh my God." She later told me that Jack was not that long, only about six or seven inches but he was as thick as her wrist and he was not even fully hard. "I can't take something that wide in my ass, it will tear me up," Ann said. Jack just smiled and said, "You really have no choice little lady now do you." Ann knew he was right and resigned herself to her fate. Jack pulled her off of the bed and got her down on her knees in front of him. Try as she might Ann could only get a few inches of his fat cock into her mouth and getting it into her throat was not going to happen. Jack let her lick and suck for a few minutes until he was rock hard and then led her back to the bed. Jack said, "I know you are going to have a hard time taking my cock in your ass and I cannot have you yelling and carrying on so I am going to gag you because we cannot have a call go into hotel security now can we?" Ann said she was almost in a trance as she heard his words but just could not respond. She watched Jack walk over to her bag and pull out a pair of her panties and one of her nylon stockings. She did nothing to resist as he forced the panties into her mouth and then tied them in place with the stocking. Ann now knew that her fate was sealed. Jack then led her over to one of the plush chairs in her room and positioned her in front of it and told her to bend over. Ann did as he said and he told her she may want to hang onto the arms of the chair. She did as he suggested and gripped the arms of the chair tightly in her hands. Jack then played with her ass forcing first one, then two and finally three fingers into her ass. Ann grunted and groaned with each new invasion of her ass. He stopped playing with her ass and Ann knew the moment of truth was at hand. Jack arranged his thick cock directly in line with Ann's ass and pushed forward. Ann tried to move away but positioned as she was against the back of the chair she had no where to go. Jack pushed forward and as Ann felt his cock slip through the ring of her sphincter she screamed in pain into her gag as she had never had anything so wide in her ass before. "Get used to it baby," Jack said as he pushed another inch of his cock into her ass. Ann said that she literally saw stars as Jack pushed the rest of his thick cock into her resisting ass. With Jack's balls resting against her Ann thought the worst was over but when Jack started to pull back she knew that was not the case. Ann said that she felt every excruciating inch as Jack sawed his thick cock into and out of her. Ann whimpered into her gag as the invasion of her ass that she was powerless to stop continued. Jack fucked Ann's ass for a few minutes and then when he felt her loosening up a bit reached around in front of her and started to finger her clit. Ann said that she responded almost immediately and started to fuck herself back on Jack's cock. A minute or two later Ann exploded on Jack's cock and had a powerful orgasm that caused Jack to go over the edge and have his own climax. Jack lay over the top of Ann for a few minutes and then slowly withdrew his softening cock from her ass. Ann told me about the popping sound Jack made when he withdrew from her ass and how her ass felt wide open for a few minutes after he pulled out. Ann let Jack turn her around and kiss her deeply. He reminded her that this was not a one time thing and she murmured her response. Jack got dressed and as he was leaving reminded Ann that if she did not want the tape of her activities disseminated that she would let him know whenever she was going to stay at the same hotel again so he could fuck her ass again. I thought about putting a stop to Jack fucking Ann in the ass whenever she visited his hotel but decided that I could incorporate those sessions into her adventures and never did anything to stop it from happening. I must admit that I continue to be surprised at how much and how quickly Ann had changed. It was as though the flood gates had opened and once she started fucking other guys she had no problem with getting kinkier and kinkier. After her fourth adventure she even started to kid me about when I would come up with something that would actually be a challenge for her to do. I assured her that would not be a problem but that is a story for another day. Teaching My Wife Ch. 05 WARNING--This is a slut wife story meaning it is about a married woman who has rough, kinky sex with men other than her husband. The woman does not make love to the other men nor do they make love to her. They fuck, pure and simple, with some kinks thrown in such as bdsm, spanking and paddling in this chapter. The sex is not gentle. The husband is not a cuckold and there are no cream pies. If any of that is not for you then please move on and read something else and spare me the comments about how you respect your wife too much to have similar things happen to her, etc. If you respect your wife so much why are you reading porn in the first place especially porn of the slut wives variety? Although this is a multi-part story the chapters are largely self contained and it is not absolutely necessary to have read the previous chapters before reading this one although reading the earlier chapters does give you the best background. * This is the story of how my wife Ann, who used to be sexually adventurous, became more and more conservative and how I set out to change things back to and beyond where they were. As I described in the first chapter, over the years Ann had become more plain vanilla as far as sex went. The adventurous woman I loved so much had seemingly left the building along with Elvis. I told Ann that she needed to be taught how to once again be a whore in the bedroom. The words "whore in the bedroom" were hers as shortly after we were married she told me that she always thought the ideal wife was a lady outside of the bedroom but a whore in the bedroom. Because Ann had over the years pulled back the sexual boundaries we once had I told her that these lessons would be at the hands of other men. I knew that if we tried to become more adventurous and Ann objected to something that I was doing to her that I would slow down or stop because I loved her while a stranger would likely not stop and say something like, "Come on, baby, you can do it." Ann would not be as free with a stranger to impose her boundaries and would be taken beyond those limits. Because Ann went out of town for three or four days at a time in her job about every six weeks we decided that her lessons would be during these trips so as to maintain discretion and anonymity. I would pack her a kit of the items to be used for each lesson along with a video camera and an instruction letter she was to give the man or men she selected. So as not to interfere with her job, Ann would extend her trip for an additional night at our expense and tell her company that an old college friend, relative, etc. lived in the town she was visiting. The additional night would be lesson night. On each of her first two trips Ann engaged in activities with other men that we had done together earlier in our marriage such as having her pussy lightly flogged to orgasm, filling her ass and pussy with ice and then getting fucked after it melted, anal sex, having her ass and pussy stuffed with inflatable toys that were then inflated beyond her previous maximums, being fucked with a porn star sized vibrator and plain old fucking and sucking. Ann was also exposed to a room service waiter by one of the men and forced to endure being groped and fingered by him to orgasm. She also swallowed more cum than she had in a long time with me. On her third trip she was the center of a six guy gang bang with me as one of the six. We originally planned on only three guys, one of them me, but events got out of hand and Ann really made up for lost time as this was her first experience with more than one man. On her fourth trip Ann had public sex for the first time. Ann and I had talked a lot about what happened on her first four trips and watched the videos numerous times. It was a terrific turn on for both of us but we realized that we had been risky in what we had her do with strangers especially on the first two excursions and lucky that none of them had harmed her. Ann admitted that she was scared at times during each of the first two encounters as well as on her third and fourth but less so. She said that the fear in her stomach had actually turned her on more than she would have normally been. She also said that she now realized that it was best to have strangers with whom she had no prior relationship do her training because she understood how easy it was for her to say "stop" or "slow down" to me. As Ann experienced in her first four sessions, strangers did not listen nearly as well to "stop" or "slow down." We also talked a lot about what happened on her third trip even though I was there. Ann said that she enjoyed being the center of attention with a group of guys working her pussy, ass and mouth over. She did not enjoy drinking down a glass with six loads of cum in it or having binder clips put on her nipples to motivate her to do so. We talked a lot about how she felt emotionally and Ann said that at first she was very hesitant about picking up a stranger for sex but that she got over her hesitation because I was helping to arrange things and she had my approval. She also quickly saw that I was right that a stranger would better push her limits and that she had learned the difference between making love and fucking. Finally, she admitted that it was a turn on to be able to pick up good looking men because as she grew older she thought that she was not as attractive or sexy as she was when she was younger. Her experiences had definitely transformed Ann into a better lover and our sex became hotter as I did not have to hold back as I sometimes did in the past. Ann even agreed to swap and we have since traded partners with a few couples we met at a local club. No orgy, just she with the husband and me with the wife. Sometimes in separate rooms and sometimes in the same room. Because of these experiences Ann was definitely returning to and going well beyond the sexually adventurous woman she had been earlier in our marriage. Her experiences had transformed her quickly into the slut wife I always wanted her to be. Ann told me that she was like a moth drawn to a flame when it came to the anticipation of her next adventure. She knew that she would do new things and have her boundaries pushed. She also knew that she would not like all of those things but somehow that added to how much she would get turned on. Ann said that there was something about the planning and preparation of her previous sessions that turned her on something fierce. She said she knew that by adding a day onto her trip that she was setting aside time for sex and would get a tingle in her pussy when she arranged for the extra night in the hotel. She said that the tingling would continue when she put the toy kit I had prepared into her luggage along with her hose, short skirt, CFM heels and other "hunting" clothes. Ann said her pussy would also tingle when she put the letter I had prepared for her into her purse. Apparently anticipation and trepidation were a big part of the appeal of her sessions to Ann. Ann said that she liked it better when she was not permitted to read the letter or look in the toy kit until her session actually started. She said that not knowing what was in the letter left her almost constantly wondering and fantasizing about what was going to be done to her. She admitted that she had even fingered herself to an orgasm a few times before her last trip after her pussy grew wet from her pondering the mystery of what would be done to her in the near future by a man or men she had never met before. The other change in Ann was that she started to push me to up the ante as it were. When we first started with her training sessions I had to almost coerce her into participating. As time went on she became more and more a willing participant. Now that once reserved woman was sitting across from me at the dinner table and saying, "I hope you are finally able to come up with something tough for me to do on my next trip." She then smiled demurely. "Be careful what you wish for," I said and returned the smile. Wow, in a little less than a year a woman who had been all about limits in the bedroom was now challenging me to test her sexually. Ann had a trip coming up in three weeks and I set about coming up with her challenge. Those of you who have read Chapters 1 and 2 will recall that much of what the strangers did to Ann in those sessions was based on things we used to do earlier in our marriage. I decided to return to that pattern for Ann's fifth session. Earlier in our marriage we had experimented with spanking and the use of belts and a riding crop on Ann's lush ass. But let me describe that ass and the rest of Ann before I get further into the story. Ann is 5'2" tall and weighs 115 pounds. She has brown eyes and medium length brown hair that at times looks reddish in certain light. Her skin is very pale and she has a lot of reddish freckles on her tits and shoulders. Her breasts are a natural B cup topped with light brown/pinkish nipples which get about a half an inch long when she is aroused. Ann has a very, very thin waist which gives her a classic hourglass figure and an ass to die for. She does not have any tattoos or piercings but does keep her pussy shaved, a nice new development from her training. We never had children so Ann's pussy is nice and tight and there are no stretch marks. Our experimenting with spanking sometimes focused on Ann giving me a blow job and I would periodically pull her mouth away and give her a few spanks to give her more motivation to do a better job. After feeling my hand coming down on her ass Ann would take my cock back into her mouth and suck like a woman possessed. Her head would bob up and down frenetically and her cheeks would be indented from the sucking she was doing. Sometimes I used a ping pong paddle instead of my hand. I would have liked to do the same pattern, sucking, spanks for motivation, repeat for a longer time but Ann did not like getting her ass spanked more than 10 or 12 times so I never pushed her too far for fear that my blowjob would not get finished. I decided that a stranger would get to push her limits in this regard on her next trip. Admittedly I never understood Ann as far as spanking was concerned. She did not seem to enjoy the actual spanking that much but she willingly bought instruments that she knew would be used to spank and otherwise abuse her ass. I once told her to buy a ping pong paddle to use on her ass and when I got home the next day there was a ping pong paddle laying on my side of the bed. On another occasion I told her to go to the local sex toy shop and buy a whip. The next day she came home with a short black leather flogger. The most erotic part of that was that she told me that as she was walking to her car after leaving the store a guy came up to her and said, "I saw what you bought and would like to talk with you." Ann told me that she did not reply and kept walking. She got in her car and drove home. I wonder to this day whether the guy wanted to have Ann use the flogger on him or whether he wanted to use it on her. Once we were shopping at a store that sold pottery, linens and other house type stuff. They had a small area of leather accessories and I was surprised that they had a bin full of riding crops. I took one out and playfully slapped it against Ann's ass. She got a little embarrassed when she realized that there were two guys behind her at the end of the aisle and that they had heard if not seen what had just happened. I decided to buy the riding crop and got in line at the cashier. Ann stood beside me and we slowly moved up to the register. The clerk gave Ann a sort of knowing glance when she rang up our purchase as the crop was the only thing we bought. The riding crop never really worked out as Ann thought it was too intense and it got lost somewhere over the years. For adventure number five I decided that Ann would get her ass worked over and spanked and more to a crimson red. I thought that Ann might figure out what I had in mind for her because one of the videos I had flagged for her to look at before her trip was a five minute clip entitled "Sucking," (ya gotta love the originality of porn movie makers). In it the woman or girl, you never see her face, is positioned on a bed on her stomach with two pillows bunched under her with her skirt flipped up and her panties pulled down. The guy kneels in front of her and she starts to suck him off. As she does he takes his belt and uses it on her ass until he cums and she swallows his load. Ann said she did not make the connection until she found herself in a similar position with a guy using his belt on her ass while she struggled to suck him off. She then realized what her fifth adventure would be about. The letter I gave Ann read as follows: "If Ann has given you this letter then things have progressed pretty far and she wants you to use her and fuck her. Ann is my wife and she has agreed that she needs to be trained to be more of a whore in the bedroom. She is yours for the night provided that you allow her to video your session and use a condom when you are in her pussy or ass. Other than that she is yours to do with as you see fit but you must at least do the things listed in this letter to her. There is a toy kit in Ann's luggage. In the kit is a tube of sex lube, condoms, a ping pong paddle, a ball gag, handcuffs and assorted lengths of rope. When Ann and I played around with corporal punishment of her ass she did not need to be restrained but as I want you to push her limits further than she let me the restraints are there if you need them. Because I love Ann I was reluctant to push her limits and would usually back off when she wanted to stop or slow down. You, on the other hand, have no emotional attachment to Ann and hopefully all she is to you is an attractive woman with whom you are going to engage in hot kinky sex. During the course of the night, Ann may object to certain things you are doing and she will carry on and try to talk you out of it but do not take "no" for an answer. Ann understands that she cannot say "no" except for violations of the video and condom rules or to any activity that would permanently hurt or mark her. Also no scat or water sports. Ann used to be very hot in bed but over the years our sex had gotten stale and we decided on sessions like these to spice things up. Ann has had four sessions like this one with various strangers. Those sessions have gotten her back to and beyond the sexually adventurous woman she was earlier in our marriage and I hope her session with you will continue to guide her down that path. OK, now for the things you are to do to Ann: 1) Position Ann on the bed on her stomach and put some pillows under her to raise her ass. Make it so her naked ass is as perfect a target as possible. Take your belt and get on the bed in front of her. Put your cock in her mouth and tell her she is to suck it until you cum and she swallows your cum. Start to spank her ass with the belt and continue until she has finished with you. 2) For the rest of the night use spankings as a way to motivate Ann to do whatever she is doing better. For example, if she is fucking you stop periodically and give her a couple of hard spanks on the ass with your hand, belt, paddle or whatever and tell her she can do better. Stop a few times during each activity and blister her ass even if she is doing a great job at pleasuring you. I want her to be pushed further than she has been pushed before. Otherwise you can fuck Ann in any of her holes provided you use a condom when in her ass or pussy. However, the focus is on punishing Ann's ass while you are doing other things to her and with her. Remember, Ann has selected you and she is your fuck toy for this evening and tomorrow morning. You are not making love to her; you are using her and fucking her." Unlike her previous four trips this trip was going to be to a medium sized college town as opposed to a major city. I figured that there are guys everywhere looking for an easy fuck and that Ann would not have any difficulty is finding a guy to administer her fifth lesson. We decided that unlike on her previous trips where Ann stayed on in the same hotel and reimbursed her employer for the extra night of her stay that Ann should check out of her hotel to close the books on her business expense when she would have normally and then either immediately check back in or use a different hotel for her lesson night. We got worried about her using the "I stayed over to see some friends, etc." line too many times at work. When we talked on her second night out of town Ann told me that she had decided to change hotels because she found a bar in another hotel that seemed to always attract a crowd in the evenings. Ann finished her business meetings about mid-day on Friday and got settled in her new room. She took a shower and otherwise freshened up and did her make-up to perfection. She next looked in her bag for the "hunting" clothes I had packed for her and saw that I had included a pair of black fishnet thigh high hose instead of the usual garter belt and hose. I had opted for the thigh high hose because I wanted her ass totally open to the punishment it would be receiving. She also noticed that I had packed one of her shortest and tightest skirts. It was best describes in terms of inches below the bottom of her butt, there were not many, and it fit her like a second skin showing off every inch and curve of her succulent ass. I did not let Ann pack any panties but the skirt was so tight that she would not have been able to wear them anyway because the panty lines would clearly show. The top I selected was rather filmy and in the right light you would be able to see Ann's breasts and nipples as she would not be wearing a bra. Ann got dressed in her top and skirt and then slipped on her four inch CFM heels. She later told me that when she stood up after putting on her heels it felt as though her butt was even more prominent in her tight short skirt. A final shot of perfume and she left her room and headed for the hotel lounge. She found a seat at one end of the bar and ordered a drink. Ann positioned herself so that she was mostly facing into the lounge area of the bar and essentially pointed her knees straight out towards the main seating area. When she sat down her short skirt rode up on her hips a few inches and you could actually see the tops of her thigh high fishnet hose and a bit of naked thigh above that. Ann sipped her drink and surveyed the room looking for a candidate to pick up for her fifth lesson. Ann crossed and uncrossed her legs periodically each time lingering and leaving them open for a few moments so that her lack of panties would be evident. Ann had just reached back to pick up her drink from the bar when she heard a voice from behind her saying, "I just have to meet the sexiest woman I have seen in a long time." She was startled by the very direct approach and turned towards the voice and saw that it came from a guy who was at best in his early twenties. Ann said that she gulped when she realized that a guy less than half her age was looking to pick her up. The guy, his name was Kevin, turned out to be about 6'2" and around 195 pounds. He was as Ann described him, "a hunk." He had dirty blonde hair and piercing blue eyes. He played lacrosse for the local college which explained his sculpted physique. Ann said that she could feel her pussy getting wetter and wetter as she realized that Kevin was looking to spend the night with her. Ann and Kevin chatted for a bit and Ann unabashedly flirted with him. After a second round of drinks Ann decided that she would see if Kevin was game to be the trainer for her fifth session. She told him the whole history of how we had started down this road and summarized what had happened to her during her first four sessions. Ann said that her tale was obviously getting Kevin's attention as she caught him several times trying to surreptitiously adjust the hardening cock in his trousers. Teaching My Wife Ch. 05 "Let me do that," Ann said as she reached out and discretely cupped Kevin's cock in her hand and felt it through his trousers. Ann said, "From what I am feeling it looks like at least part of you is interested so let me show you the letter from my husband." She reached in her purse and gave Kevin the letter. Kevin read the letter and said, "Are you kidding me, some of my fraternity brothers must have set this up to yank my chain." "No," Ann replied, "I am completely serious. I need to know if you are willing to do what the letter says." "Do you know what the letter says," Kevin asked. "No, my husband and I decided after the first session that I would not know what would happen to me beforehand and dreaming about what will be done to me keeps me hot for a week before my trip," Ann said. "OK, then let's get out of here," Kevin said. "You understand the rules about letting me video tape the session and using a condom, right?" Ann asked. "Sure, no problem," Kevin replied. He continued, "My whole frat has a rule about using condoms because a few years ago a guy who had graduated about ten years earlier died of AIDS and since then the national office has pushed safe sex on all of its chapters. They show us a movie every year featuring interviews with people dying of AIDS and it usually scares the shit out of everyone." Just then the bartender came by and asked if Ann and Kevin wanted another round and Kevin asked for the check. The bartender put the check on the bar and Kevin started to reach for his wallet when Ann said, "No worries, I will just put it on my room; I remember being in college and not having a lot of money." Kevin just smiled and said, "Thanks." I got as terrific kick out of the whole episode because here was my wife picking up a guy who would soon be blistering her ass with his hands, belt and paddle and later fucking her and she was buying his drinks to boot. Ann and Kevin got up and walked out of the bar together, the attractive mature MILF and the twenty something hunk. They walked out of the bar and made their way to Ann's room. Ann said she remembers hearing the door click shut because she knew that sound meant that she could no longer say "No," except to violations of the video and condom policy or to anything that would permanently hurt or mark her. Ann set up the video camera and said, "OK, what's it going to be?" Kevin came over, took her in his arms and kissed her and said, "Let it be a surprise." They kissed deeply for a while and Kevin got Ann's top off and he sucked first one and then the other of her nipples into his mouth. Ann started to moan and she was clearly turned on at the thought of this young hunk fucking her and more. Her skirt came next and Ann stood naked before a guy less than half her age except for her black fishnet hose and CFM heels. Kevin took Ann by the hand and led her over to the bed. He moved two pillows down to the center of the bed and positioned Ann over them on her stomach so that her lovely ass was elevated. He rubbed her ass a bit and then reached under her and played with her clit until he had her close to an orgasm. He stopped just short of making her cum and went over to where his trousers lay and took out his belt. Ann said that she immediately knew that she was going to be the girl in the "Sucking" clip she had watched. Kevin finished undressing and got on the bed in front of Ann and said, "I am going to use my belt on your ass until you make me cum with your mouth and swallow it down." He held his cock up for a second and Ann took it into her mouth and went to work. Ann later told me that as soon as she realized that Kevin was using her as the suck whore in the "Sucking" video she tried to suck his cock as hard and as fast as she could to spare her ass as much punishment as possible. Despite her best efforts, it took a little over four minutes for Kevin to shoot his load and you could hear Ann yelp and grunt around Kevin's cock each time his belt struck her upturned ass. Ann easily took over 50 stripes on her ass before she made Kevin shoot down her throat. Once Ann moved one of her hands down to rub or protect her ass and Kevin grabbed her wrist and said, "Keep your hands away or I will handcuff you." When she moved her hand away Kevin gave her an extra hard slap with his belt. Ann let Kevin soften in her mouth and then sucked the last few drops of his cum as he withdrew. They were lying in bed when Kevin's cell phone rang. He got out of bed and retrieved his cell phone from his pants. On the video we could hear only one side of his conversation. "Yo, Kevin here." "What cha' doin"?" "You aren't going to belief this but I am at the hotel with this incredible MILF." "She already sucked me off and I have a letter from her husband saying he wanted me to paddle her ass for the rest of the night." "Geez, Guinevere, I hadn't thought of that." "So it's you and George and his girlfriend, Angie." "OK, I will see you in a while." Kevin turned to Ann and said, "Get dressed; we are going over to my frat house." Ann protested both about going somewhere besides her room and getting other people involved but Kevin picked up the letter and said, "I don't see anything in the letter that says you don't go where I want you to go and do whatever I want you to with whomever I want you to you." She took the letter from his hand and scanned it quickly. When she was done she slumped her shoulders as she said, "You're right," I have to go where you want me to go and do whatever you want me to do." She also rubbed her still stinging ass with one hand and shuddered because she now knew from reading the letter that her ass was in for more punishment. Ann put her filmy top back on and her nipples protruded enticingly. She had not cum during her spanking and was still turned on from the other attention Kevin had paid to her body. She stepped into her skirt and gently tugged it up over her hips and pulled the zipper up. The tightness of her skirt further pressed against her otherwise naked and now reddened ass again focusing her feelings on the part of her that would continue to be abused. Ann put the video camera into her purse and said, "What about the toy kit?" "We have everything we should need at the house." Kevin opened the door and they walked into the hall and out of the hotel. Kevin led Ann over to his car and opened the passenger door for her. He got in the other side and they were off. They had driven only a mile when Ann said, "Shit, I forgot the condoms. You have some at the house, right?" she asked. "Actually we don't as we had a couple of wild parties recently. I was supposed to pick some up on my way back tonight. Don't worry there is a drugstore a few blocks from here." Kevin turned right and then left and pulled into the parking lot of a drugstore. It was one of the national chains and the lot was brightly lit. He parked the car and Ann assumed that he would leave her waiting in the car. Kevin got out of the car and walked around to Ann's side and opened the door. Ann stammered for a second and said, "Can't you just go and get them? I'm not sure I'm dressed for this." "Sure you are," Kevin said as he took Ann's hand and pulled her out of the car. "Besides, I want everyone to see the attractive woman I am spending the night with." Ann said that she could feel her face flushing as her embarrassment mounted as they walked across the parking lot. She said that the bright lights of the parking lot felt as though they were going right through her filmy top and she knew that in the brightly lit store her top would do little to hide her nipples or the outline of her tits. It got even more humiliating once they were in the store. "On the tile floor my heels made a sharp click with every step and without a bra my tits jiggled. The lights left no doubt that I was bra less and my nipples were even harder than they were back at the hotel," Ann later told me. Kevin led Ann over to the condom display, paused for a few moments and then selected two 36 condom packages. He reached into his pocket, counted out some bills and gave the bills and the condoms to Ann saying, "Here, buy these." Ann felt like running away as her humiliation mounted. She was going to have to walk to the cashier, wait in line holding two big boxes of condoms and nothing else and then complete her purchase. Her almost see through top, very short skirt, fishnet hose and CFM heels made her look sexy as hell and left little doubt that she was going to get fucked. Having this young hunk standing next to her while she bought six dozen of condoms only made it only worse. Despite her humiliation Ann said that her pussy was soaked and she could feel her juices leaking down the insides of her thighs. She said that even her breathing had grown more rapid. Shopping done, Kevin got Ann back in the car and they were off again. In a small voice Ann asked, "How many people will be at your fraternity?" Kevin knew Ann was worried about becoming the center of an all hands on deck gang bang so he said, "Well, it's Friday night and there is usually a party so I would say 40 or 50." "Oh my God," Ann replied. Kevin talked about how wild their parties were for a few minutes and then said, "I'm just kidding you. The college is closed for the break between quarters and most of the guys have gone home. It is only me and two other guys and the girlfriend of one of the guys." Ann breathed a sigh of relief and said, "I thought there were two girls because you mentioned Angie and Guinevere on the phone." Kevin smiled and said, "Well we call her Guinevere and assume she is a girl." He paused for a few seconds before continuing, "Don't worry, you will meet Guinevere soon enough." In another minute they were at the house and Kevin led Ann inside. Introductions were made with Kevin introducing Stan and George, his two fraternity brothers, and Angie, George's girlfriend, to Ann. Stan went and got five bottles of beer and handed them out and Kevin set up the video camera. Kevin looked over at Ann and said, "Why don't you tell everyone how you happen to be here." Ann started at the beginning of how her training sessions had been arranged and what she had done and had done to her during each. She even told them about what Kevin had done to her earlier in the evening. Finally, she said that Kevin had the letter that detailed what was to happen to her tonight and the rules about condoms and permanent marks. "The letter basically says that we are to punish Ann's ass until she sucks and fucks us to our satisfaction," Kevin said. You could see Ann visibly tremble at his words. "Well let's get this show on the road," Stan said. He walked over to where Ann was standing and said to her, "Show us what we are going to be working with tonight." Ann's hands slowly moved up and she started to open her filmy top. When it parted in the front everyone could see her hard nipples and her breasts moving up and down on her chest with every breath. Ann pulled the top completely off and stood topless in front of four college students less than half her age. She said that she felt a mixture of embarrassment, lust and satisfaction knowing based on the bulges she saw forming in the guys' pants that she still had what it took. Ann next opened the button on the side of her skirt and pulled the zipper down. She wriggled as she pulled the skirt down over her hips and stepped out of it when it hit the floor. As she bent down to pick it up you could see that her ass was still red from the strapping Kevin had given her earlier. "Time to meet Guinevere," Kevin said and Stan and George went over to the corner and pulled an old wooden spanking horse into the center of the room. You could tell it has been around for a while as the wood was worn in spots as were the various leather straps. "Guinevere has been in the fraternity for over fifty years," Kevin said, "She gets used when we initiate our pledges." He led Ann over to Guinevere and said, "Let me show you how it works." Kevin showed Ann the various straps and how the person who was going to be paddled was positioned. He also showed her how they had modified it to fit a vibrator in a strategic place for when it was used on a girl. He explained that one of the sororities had started to borrow it for their initiations and had come up with the idea. Ann stood silently and listened to him and offered no resistance when he positioned her behind the horse and pushed her down over it. Hands quickly put the leather straps around Ann's ankles and above her knees. Two other straps went over her back and shoulders and two more secured her hands. Ann said that she had reached the moment that she both dreaded and looked forward to in her sessions. That is, the moment when she knew that she had no choice but to have her limits pushed further than they had been before. Ann silently bit her lower lip as she awaited her punishment to begin. Kevin reached under her butt and turned the vibrator on. Ann jumped a bit as she felt the vibrations hit her already engorged clit and then settled down, pushing herself against the vibrator as hard as she was able. Ann watched as Kevin walked over to a rack on the wall and took down the wooden paddle that was hanging there. As Kevin walked over to where Ann was restrained in a trembling voice she said, "Please remember what the letter said about not doing anything that would permanently hurt or mark me." "Don't worry about that, we have done this before and know how hard we can hit. Your ass will stay red for a while and it will be uncomfortable for you to sit for a few days but other than that you will be fine," Kevin replied. "When we do this to the pledges we usually give each a set number of strokes with the paddle. However, the letter says the punishment is to motivate you to suck and fuck better so here is how it will go. One of us will get behind you and give you three swipes with the paddle. Someone else will get in front of you and after the third swipe you will start to service them with your mouth. The person getting serviced will, if they are satisfied with your efforts, hold up their hand which will tell the person paddling you to stop. Otherwise your ass will continue to be paddled. When you have made all four of us cum with your mouth we will move on to the fucking part." You could see Ann's eyes open wide in surprise. Four to service meant that she was going to have to make Angie cum with her mouth as well. Ann later told me that she had assumed all along that Angie was going to just watch. As Ann had never licked or sucked another woman's pussy before this night was going to have another first. Stan got undressed and walked around the front of the horse and George picked up the paddle. "Here we go," he said as he landed the first blow across both of Ann's butt cheeks. Ann said that the first blow stunned her more than anything and that the pain did not immediately start to register. On the second and third blows Ann let out an "Owwww," as each blow landed. On cue, Stan took his hard dick in his hand and pushed it into Ann's mouth. It was no sooner in than a fourth blow landed and Ann's "Owwww" was muffled by the large cock pushing its way into her mouth. A fifth blow landed and Ann again voiced her muffled displeasure and she realized that the only way to stop the punishment of her ass was to suck like she had never sucked before. Ann started to suck as hard as she could and you could see her cheeks indented from the effort. She also started to move her head up and down on the dick in her mouth as fast as she could. Because of the way that she was restrained Ann could not move her head enough to run the full length of Stan's cock in and out of her mouth but she did what she could. Another blow landed on her ass and Ann tried to suck even harder. Stan raised his hand to stop the spanking and let Ann minister to his cock. Ann was doing her best to maintain her frenzied pace but it was tiring and whenever she slowed down for a respite Stan would drop his hand resulting in another blow to Ann's now reddening butt. Stan started to help Ann by pushing his cock in and out of her mouth. On one out stroke he pulled all the way out and Ann said, "Push it all the way into my throat." Stan obliged and in one hard thrust had his balls resting against Ann's chin. Ann later told me that she knew she could not keep up the pace for long enough to protect her butt so she decided to get the guy she was sucking to deep throat her because he would do the work and she would get a break. Her strategy worked on two levels as Stan took over the work of moving his cock into and out of her mouth and got so aroused by being deep throated that he blew his load shortly thereafter. Stan pulled out of Ann's mouth and she gasped for air and hoped that she would get a few moments to rest. Her rest was short lived as Angie stripped off her jeans and top and had one of the guys bring an ottoman and put it in front of the horse. Angie climbed on the ottoman and presented her pussy to Ann, virtually shoving it under Ann's face. Ann could see the cunt in front of her glistening with the juices Angie was secreting and said that she could also smell Angie's arousal. Stan, meanwhile, had picked up the paddle and administered the first three blows. Ann grunted loudly with each. Angie said, "I will help you out because your hands are tied," and she opened herself up with her fingers. Angie was about 5'6" and very slender with almost a boyish figure except for her medium sized breasts that protruded enticingly from her chest. Angie had green eyes and although her hair was blond it looked from the darker roots that it was chemically engineered. Angie was shaved and had a small tattoo of a rose just above her pussy. Ann was still taking all of this in when Stan let her have two more blows with the paddle. Ann squealed with each of the blows and quickly got her focus back to the matters at hand. Ann had never eaten a pussy so she was not sure of exactly what to do but decided that she would do the things that the men who had eaten her pussy had done to her and hope they also worked on Angie. Ann started to lick Angie's pussy up and down and when she found her clit pushed her tongue against it. Angie started to respond but she had not yet raised her hand so the blows continued to rain down on Ann's ass. Ann yelped or squealed with each blow and you could hear her clearly because unlike when she had a cock in her mouth there was nothing to muffle the sound as she licked Angie's cunt. Ann then pressed her lips to Angie's cunt and started to suck the folds of her labia into her mouth. Angie must have liked that because she soon raised her hand giving Ann a respite from the blows that Stan was delivering to her ass. Angie started to rotate her hips and in the process rubbed her cunt over much of Ann's face. When Ann pulled away for a second you could see Angie's pussy juice on Ann's cheeks, lips and chin. "Suck my clit," Angie directed and Ann found the little nub and sucked it into her mouth. Ann would suck Angie's clit into her mouth and then keeping the pressure on she would move her head back letting it slip out of her mouth. "Stick your tongue inside of me," was Angie's next directive. "Deeper," Angie said and you could see Ann's lips plastered up against Angie's cunt as Ann tried to force as much of her tongue into Angie's slick tunnel as she could. "You can get deeper than that," Angie said and dropped her hand. Stan immediately gave Ann two blows with the paddle and although Ann jumped on each she kept her lips firmly planted against Angie's cunt and continued to try to force her tongue further in. Teaching My Wife Ch. 05 "Come on, deeper," Angie said and she kept her hand down. Ann sucked even harder and you could see her lips start to disappear into Angie's cunt and her tongue must have gotten in further as well. Nevertheless another two blows had descended on Ann's ass. Angie seemed satisfied with Ann's efforts and raised her hand again stopping the paddling. Angie let Ann suck on her cunt for a few more minutes. "Lick my ass," Angie said. Ann did not move and Angie said more firmly, "I want you to lick my ass." I knew that this would be tough for Ann because she had never licked anyone's asshole before and was now being ordered to do so by a girl less than half her age who she had only met less than an hour ago. Angie dropped her hand and Stan started to paddle Ann's ass again. After the third blow Ann was panting in pain and said, "OK, please stop, I'll do it. Just give me some time." Angie kept her hand down as Ann slowly slid her tongue down from Angie's pussy and made contact with her asshole. Ann licked Angie's ass a few more times and then stopped for a second and plaintively said, "Please, my ass is on fire." Angie raised her hand and said, "Put your tongue into my ass." Ann hesitated for a second and Angie lowered her hand resulting in another blow across Ann's butt cheeks. "Put your tongue in my ass or I will never raise my hand," Angie said. Ann knew that she had no choice and put her lips close to Angie's asshole and slowly forced her tongue inside. Ann had no sooner slipped her tongue into Angie's ass when Angie said, "Suck my ass." Ann slowly pressed her lips around Angie's asshole and when they were firmly seated started to suck. Her sucking forced more of her tongue into Angie's ass and Angie exclaimed, "That's it, you fucking bitch, suck my ass. Get that tongue way up in there." Ann later told me she felt totally mortified and humiliated but knew that she had no choice so she just kept putting suction on Angie's ass and forcing her tongue as deep inside as it would go. Angie started to buck her hips and said, "That's it you bitch, keep pushing that tongue inside of my ass." A few more gyrations and Angie came hard with Ann's tongue in her ass. Angie slowly got up off of Ann's face and it was only seconds before George was forcing his cock down Ann's throat. It took Angie a few seconds to get hold of herself and to get her hands on the paddle. Angie made up for lost time as she quickly delivered three sharp blows to Ann's upturned ass. Ann shrieked around the dick that was in her mouth but somehow kept on sucking. Angie delivered two more blows and then George raised his hand and let Ann suck his cock. Ann was clearly out of her mind with pain and lust as she had not yet cum and after the last few blows the heat in her ass had finally started to make its way to her pussy. Ann continued to inhale George's dick down her throat and managed to position herself so that her clit was now directly on top of the vibrator. Ann slid her clit up and down on the vibrator and somehow managed to keep working on the dick that was making its way down her throat. After a few more strokes Ann exploded into an orgasm and actually convulsed as she came. George had not yet come and Ann kept sucking his dick deep into her throat. Ann kept her face against his crotch so that his entire dick was in her mouth and throat. George had not previously experienced the joys of having his cock deep throated. He moaned as he pumped his cock vigorously into Ann's mouth and deep into her throat. Another thrust in to the hilt and George finally reached his limit and exploded. His seven plus inch cock shot its load directly down Ann's throat and into her stomach. I did not notice it the first time I watched the video but later saw that Angie appeared to be getting jealous as Ann sucked her boyfriend's cock. I noticed that Angie's mouth was in sort of a smirk or a sneer and you could see that as her boyfriend's blowjob progressed the blows Angie delivered to Ann's ass got harder and harder. Even though George had cum he was still moaning as though his orgasm had aftershocks or something. You could see that Ann kept sucking him even though his dick was getting soft. His dick finally softened some more and he pulled out of Ann's mouth. "That was fucking fantastic. No one has ever taken me down their throat before." George ran one of his hands through Ann's hair and said, "You were great, honey, I can't remember when I ever came that hard." This really set Angie off and she yelled at George, "Fucking fantastic, huh? Maybe you should look this slut up the next time you want a blowjob." George tried to reason with his girlfriend but she was having none of it. "Maybe I should use this paddle on your ass," Angie said as she swung and landed a good one on George's naked butt. George grabbed his girlfriend and wrestled the paddle away from her. He held her for a few seconds and when he released her she pounded her fists on his chest. He grabbed her again and Angie struggled some more. It was easy to see that she was pissed and wanted to take it out on George. Angie finally tired and stopped struggling and when George sensed that she had calmed down he let her go. When it looked like things had settled down Kevin got in front of Ann. Stan got the paddle and got ready to start paddling Ann again. Just as Stan was about to deliver the first blow Angie said, "Give me that fucking paddle and took it out of his hands." George thought that Angie was going to try to hit him again with the paddle but she stayed where she was and said to George, "If I cannot paddle your butt then your blowjob slut's ass will have to do." With that Angie reared back and delivered three hard blows to Ann's ass. They were harder than any Ann had received thus far and Ann shrieked in pain. "Put your dick in this slut's mouth and fuck her throat," Angie said to Kevin as she landed two more hard blows on Ann's ass. Ann shrieked around the dick in her mouth and tears rolled out of her eyes and down her cheeks. Kevin saw that Angie was out of control and he raised his hand to give Ann a break. Angie stopped the paddling but stood at the ready "Come on, Kevin, this bitch is hardly sucking," Angie said. Ann was still whimpering from the earlier hard blows and you could tell that she was having a hard time focusing on sucking the dick that was in her mouth. Kevin finally noticed this too and dropped his hand. "Fucking bitch," Angie said as she unloaded another hard blow on Ann's ass. Angie landed two more in rapid succession before Kevin again raised his hand. Despite the fire burning in her ass Ann had somehow found new strength and was now vigorously sucking Kevin's cock. Like she did with Stan, on one of Kevin's out strokes Ann got his dick completely out of her mouth and said, "Fuck my throat." Kevin obliged and shoved his entire cock back into Ann's mouth and down into her throat. He fucked her mouth this way for a few minutes and then finally exploded. Kevin left his cock in Ann's mouth as it softened and then finally pulled out. As Kevin pulled his dick out of Ann's mouth Angie said, "Bitch," and let loose with another hard spank to Ann's ass. Stan quickly got the paddle away from Angie and George started to release the straps that held Ann to the spanking horse. He helped Ann to her feet. Ann was wobbly for a while because she was both sore from her paddling but also stiff from being strapped down in the same position for so long. Stan helped Ann to the bathroom and left her alone so she could clean up. Ann said that she winced when her hot ass touched the cool toilet seat. Ann showered and a few minutes later rejoined the group in the other room. Kevin handed Ann a cold beer and before she even took a sip she rolled the cold bottle against her right butt cheek. When Ann had finished her beer Stan came over to her and started to kiss her and play with her nipples. He slipped a finger into her pussy and found that she was still wet, very wet in fact. Ann said that even though she had come from the vibrator during her paddling the heat in her ass seemed to radiate to her pussy and make it hotter as well. "I want to fuck you," Stan said as he led Ann out to the center of the room to some cushions someone had put on the floor while she was getting cleaned up. Stan led Ann to the center of the cushions and said, "Get on your knees." Ann knelt down in front of him and dutifully took his cock in her mouth. She used her hands to caress his balls and soon had him hard. Stan pulled out of Ann's mouth and said, "Get down on your hands and knees, I want to do it doggie style." Ann complied and moments later, after Stan had slipped on a condom, was rewarded with Stan's cock plunging into her pussy. Ann later said that one of the things she got off on the most, besides being used by guys less than half her age, was how direct they were in telling her what to do. It was as if they knew how to treat a girl as a "boy toy" and Ann wondered if sex had changed that much in the younger generation as she remembered guys being less direct and less demanding when she was younger. You could see Ann wince every time Stan plunged in to the hilt and he brushed up against her still crimson ass. Ann said it was a contest between what would win out, the pain of her sore butt or the orgasm building inside of her as Stan continued to piston his dick in and out of her pussy. The orgasm won and Ann yelled, "I'm coming," and ground her ass hard against Stan, trying to get every last millimeter of his dick into her pussy. Stan kept right on going and he wrested two more significant orgasms from Ann. While this was going on George got in front of Ann and said, "Suck my cock." Ann took him into her mouth and she was now spit roasted between the two guys who were fucking her from each end. Stan finally reached the breaking point and exclaimed, "Fuck," as he drove his cock into Ann one more time as he came. Stan pulled out and George took his place in Ann's pussy. George had just started fucking Ann when Kevin got in front of her and presented his cock. Ann sucked him into her mouth and her double fuck continued. Ann looked like she was getting tired and Kevin said, "Suck better than that or we will get the paddle." Ann immediately redoubled her efforts and started to push herself back and forth between the two cocks that impaled her at each end. George fucked Ann hard and fast and although he was vocal he kept away from making any comment that would further piss off Angie who was sitting on the couch watching the whole thing. Angie looked as though she was fascinated with what she was watching but you could also tell she was not happy that her boyfriend was about to get his rocks off fucking another girl. Ann meanwhile was getting the fucking she had craved since this adventure began and she had several nice orgasms from the pounding that George gave her. During one particularly intense orgasm Ann's pussy tightened its grip on George's cock putting him over the edge. George slammed his cock in one more time and came hard. Even through the condom Ann said she could feel the jets of cum. George withdrew and Kevin immediately plunged in. Ann had just about stopped cumming from the fucking George gave her when she started again as Kevin's cock bored its way into her depths. Because Kevin had come twice already in Ann's mouth his stamina was good and he fucked Ann both hard and long. Ann came hard a few more times and then just whimpered as Kevin continued his assault on her pussy. Ann later said that towards the end she no longer even noticed the pain whenever the guy she was fucking brushed up against her ass. Kevin reached around in front of Ann and started to play with her clit. This got her going again and in a few moments she cried, "Fuck, I'm cumming again." Kevin made it shortly after Ann and they collapsed together on the cushions. When Ann finally opened her eyes and looked up she saw Angie standing there staring down at her. "My turn, bitch," Angie said as Kevin got up and out of the way. "On your back," Angie instructed as she forced a pillow under Ann's head. When she was satisfied with Ann's position Angie climbed up over Ann and sat on her face, plastering her wet soupy pussy directly on Ann's lips. "Now, make me cum as hard as you did my asshole boyfriend." Ann started to gently tongue Angie's pussy lips but Angie was not interested in gentle. Angie started to grind her pussy hard against Ann's face and mouth smearing her juices across Ann's face and lips. Ann could do little except lay there and let Angie essentially masturbate herself against her face. Fortunately for Ann, Angie was apparently pretty worked up from watching Ann fuck the three guys so it was not long before Angie was moaning indicating that her orgasm was approaching. "Stick your tongue out," Angie told Ann. When Ann did Angie started to pump her pussy up and down on it as though she was fucking a really small cock. You could see how hard Angie was mashing her pussy against Ann's mouth and hear Angie's moans get louder and more intense. In another minute Angie announced that she was cumming and really impaled herself on Ann's face. Ann later told me that she could not breathe for a few moments because Angie had covered both her nose and mouth with her pussy. Angie climbed off of Ann's face and Kevin helped Ann to her feet. Ann went to get cleaned up again and emerged about 20 minutes later. Ann said that she thought there would be more when she came out of the bathroom and was surprised to see that everyone had gotten dressed. Ann was still naked except for her hose and CFM heels and she said that she somehow felt conspicuous in her nudity even though she had just spent the last several hours having sex with these people. Kevin handed Ann her top and skirt and said, "Get dressed; I will take you back to the hotel." Ann put her top on and then stepped into her skirt. It was slow going as she pulled it up over her still painful ass because the fabric was coarse and the skirt was so tight. Ann said her goodbyes and Kevin led her out to his car. He opened the door for her and watched her wince as she sat on her still heated ass. Ann said that all the way to the hotel she kept shifting from one cheek to the other trying to find a position that did not exacerbate the pain of her sore butt. During the drive Kevin told Ann that she had taken many more strokes with the paddle than any of their pledges and that he thought that at least made her a little sister of his fraternity. He said as such she could attend their parties and Ann said that as long as she did not have to deal with Guinevere she would think about it when she was in town again. Kevin pulled up to the hotel lobby entrance and helped Ann out of the car. They embraced and he gave her a long good night kiss. Ann slowly walked into the hotel and through the lobby. It was slow going because each step caused her skirt to press against her wounded ass. She said that she saw the reflection of the desk clerk in one of the mirrors and he was looking at her butt as though he knew what had happened to her. Ann slowly made it up to her room and even more slowly slipped her skirt down over her ass. She said that she slept in the nude that night on her stomach on top of the covers as she could not tolerate the feel of anything against her still blazing ass. The next morning the heat had subsided a bit in her ass and she flew home later that day. When she walked through the door I was waiting for her and handed her a drink. She stood and started to tell me how her adventure went. She related the story of her paddling and how red it had made her ass. "Show me," I said and she put down her drink and slipped off her skirt. Ann turned around and I saw that her ass was still a bright red. I got up and walked over to where she was standing and put my arms around her and pulled her close. I slipped my hands down and grabbed both of her butt cheeks and gave them a squeeze. "Owwww," Ann said. "So, was this adventure challenging enough for you?" I asked. Teaching My Wife Ch. 06 WARNING-- This story depicts group sex, a lot of bdsm and forced sexual activities, extramarital sex, and several fetishes such as spanking (ass and pussy) and bukkake all engaged in by a slut wife. The wife does not make love to the other men nor do they make love to her. They fuck, pure and simple. If you are looking for the monogamous couple spicing thing up with each other type of story while rainbows and butterflies appear overhead there are a few good ones that were recently posted. This is not one of them. The husband is not a cuckold and there are no cream pies. If any of that is not for you then please move on and read something else and spare me the comments that show you were unable to even comprehend this first paragraph. I purposely typed this paragraph slowly so that those who persist in posting and sending childish comments can follow it better. I will respond to all sensible e-mails but if you feel compelled to send a childish e-mail when you do please also send me a link to the stories you have contributed here or elsewhere so that I can learn how to improve my writing. Although this is a multi-part series the chapters are largely self contained and it is not absolutely necessary to have read the previous chapters before reading this one although reading the earlier chapters does give you the best background. * This is the continuing story of how my wife, Ann, who used to be sexually adventurous, became more and more conservative and how I set out to change things back to and beyond where they were. I told Ann that she needed to be taught how to once again be a whore in the bedroom. The words "whore in the bedroom" were hers as shortly after we were married she told me that the ideal wife was a lady outside of the bedroom but a whore in the bedroom. Because Ann had over time pulled back the sexual boundaries we once had I told her that these lessons would be at the hands of other men. I knew that if we tried to become more adventurous and Ann objected to something that I was doing to her that I would slow down or stop because I loved her while a stranger would likely not stop and say something like, "Come on, baby, you can do it." Ann would not be as free with a stranger to impose her boundaries and would be taken beyond those limits. Ann went out of town about every six weeks on business. We decided that her lessons would be during these trips so as to maintain discretion and anonymity. I would prepare a kit of the items to be used for each lesson along with a video camera and an instruction letter she was to give the man or men she selected. So as not to interfere with her job, Ann would extend her trip for an additional night at our expense and tell her company that an old college friend, relative, etc. lived in the town she was visiting. The additional night would be lesson night. On each of her first two trips Ann engaged in activities with other men that we had done together earlier in our marriage such as having her pussy lightly flogged to orgasm, filling her ass and pussy with ice and then getting fucked after it melted, anal sex, having her ass and pussy stuffed with inflatable toys that were then inflated beyond her previous maximums, being fucked with a porn star sized vibrator and plain old fucking and sucking. Ann was also exposed to a room service waiter and forced to endure being groped and fingered by him to orgasm. She also swallowed more cum than she had in a long time with me. On her third trip she was the center of a six guy gang bang with me as one of the six. We originally planned on only three guys but events got out of hand and Ann really made up for lost time as this was her first experience with more than one man. On her fourth trip Ann had public sex for the first time. Her fifth adventure featured her getting paddled, fucked and more by a group of fraternity guys. Ann admitted that she was scared at times both before and during each of her adventures but said the fear in her stomach had actually turned her on more than she would have normally been. We talked about how she felt emotionally because all of this was new territory as Ann had only had one other partner besides me before these adventures started. Ann said that at first she was very hesitant about picking up a stranger for sex but that she got over her hesitation because I was helping to arrange things and she had my approval. She also quickly saw that I was right that a stranger would better push her limits and she had learned the difference between making love and fucking. Finally, she admitted that it was a turn on to be able to pick up good looking men because as she grew older she thought that she was not as attractive or sexy as she was when she was younger. Her experiences had definitely transformed Ann into a better lover and our sex became hotter as I did not have to hold back as I sometimes did in the past. Ann even agreed to swing and we have since traded partners with a few couples we met at a local club. Her experiences had transformed her quickly into the slut wife I always wanted her to be. Ann told me that it was as though a dam had burst inside of her and that she wanted more and more to experience the full range of sexual possibilities. She said that she was like a moth drawn to a flame when it came to the anticipation of her next adventure. She knew that she would do new things and have her boundaries pushed. She also knew that she would not like all of those things but somehow that also added to how much she would get turned on. Ann said that there was something about the preparation for her sessions that turned her on something fierce. She said that her pussy would tingle when she put the toy kit I had prepared into her luggage along with her hose, garter belt, short skirt, CFM heels and other "hunting" clothes. Her pussy would also tingle when she put the letter I had prepared for her into her purse. Apparently anticipation and trepidation were a big part of the appeal of her sessions to Ann. Ann liked it better when she was not permitted to read the letter or look in the toy kit until her session actually started. She said that not knowing left her almost constantly wondering and fantasizing about what was going to happen. She admitted that she had fingered herself to several orgasms before her last two trips after her pussy grew wet from her pondering the mystery of what would be done to her by a man or men she had never met before and would likely never see again. The other change in Ann was that she started to push me to up the ante as it were. When we first started with her training sessions I had to almost coerce her into participating. As time went on she became more and more a willing participant and she told me that she now wanted to make up for lost time due to her prior limited sexual experience. Before her adventure with the fraternity guys she challenged me to "to come up with something tough for her to do on that trip." Apparently I succeeded because Ann's ass stayed red for almost a week from the paddling she got at the fraternity and she said that it was uncomfortable to sit for almost as long. She also must have gotten her fill because she did not ask for me to come up a scene for her during her next two out of town trips. A few days after Ann arrived home after her second trip without an adventure she said, "You know, I really missed not having a training session during my last two trips. Without the anticipation of that as well as the sex itself they were just routine, dull, boring business trips." "Sure you can handle another adventure?" I asked. "The last one seemed to be too much for you." Ann replied, "The last one was more than I expected and it was a struggle to get through parts of it but I think I am ready for another session." "I don't know, what if I come up with something equally difficult for you to do next time?" I asked. My comments were calculated to challenge the part of Ann that was very determined once she decided to do something. I knew that if I acted as though I did not think she could do something that she would do her best to prove me wrong. The strategy worked as the next day Ann again pestered me about having a training session on her next trip. Again, I demurred saying I didn't know if she could handle it and I could see her determination to prove me wrong growing. We went back and forth a bit more but again I did not commit to coming up with a session for her. The next night at dinner Ann started on me again about putting together a session for her and again I resisted until finally she said, "I can handle anything you come up with for me to do, I just don't think you have any more ideas left." "Be careful what you wish for," I said and reminded Ann that I had said the same thing before her fraternity adventure. "But I got through that didn't I?" Ann asked with a smug look on her face. "True, you did, but you didn't ask to have a session on your last two trips so I figured you were afraid of what I might come up for you to do," I challenged. "OK, so I didn't ask for another adventure right away but I am asking now," Ann replied. "If you insist I will come up with a session for your next trip, just remember your words when you are being forced to do things you do not like by a stranger." Ann smiled as she saw she was going to get what she wanted and I asked, "OK, so when is your next trip?" Ann said that it would be in about a month to a national conference of doctors and medical professionals, was at a warm weather resort and would be for an entire week. I smiled to myself knowing that it would be perfect for what I had in mind. Before getting on with the story let me describe Ann for those of you who may not have read the previous chapters. Ann is 5'2" and weighs 115 pounds. She has brown eyes and medium length brown hair that at times looks reddish in certain light. Her skin is very pale and she has reddish freckles on her tits and shoulders. Her breasts are a natural B cup topped with light brown/pinkish nipples which get a little more than a half an inch long when she is aroused. Ann has a very, very thin waist which gives her a classic hourglass figure and an ass to die for. She does not have any tattoos or piercings and now keeps her pussy shaved. We never had children so Ann's pussy is nice and tight and there are no stretch marks. Ann has a killer smile and while she was in college finished as first runner-up in the Miss (fill in name of college cause I'm not going to tell you) competition. Those of you who have read the previous chapters and my other story will recall that in Chapter 3 Ann was gang banged by six guys including me and in a separate story she took on nearly a dozen black guys in an anal session. I had been there for both which gave her some comfort as she felt that I would protect her if things got out of hand. With her challenging attitude I decided that for her next adventure Ann would be gang banged by a group of guys and she would be on her own while it happened. The conference Ann was going to attend was scheduled to start on a Sunday and end on a Saturday allowing enough time for everything to take place. Previously we had set things up so that Ann would spend an extra day at the end of her trips for her sex training but with a week that would not be necessary. I looked up the conference agenda on the internet and saw that the schedule allowed for a lot of "down" time which I planned to have Ann put to good use. Because the conference was to be at a warm weather resort I ordered Ann a bright neon yellow micro bikini from the folks at Wicked Weasel. Although Ann would normally wear a medium top I ordered an extra small which would barely cover half of her breasts. The bottom style was Microminimus and the name is appropriate. It is a thong that would leave her ass and hips completely exposed and the very small rectangle of fabric in the front started just above her pussy and would barely cover her labia. The fabric is called Satin Sheer and it is virtually see through even without being wet. Ann's nipples would protrude enticingly and her shaved pussy would also be on prominent display. As her trip approached Ann would playfully taunt me inquiring whether I had come up with something challenging for her to do. I just smiled and said, "You will see." Her next line of attack was to ask me what I had come up with for her to do. She said that she was almost constantly fantasizing about what would happen to her and the suspense was killing her. One night I walked into our bedroom to find Ann naked on our bed watching one of the videos from one of her previous adventures. She had one of our bigger vibrators buried deep inside of her and was close to cumming. I walked over, put my fingers on her clit and started to rub gently. That was enough to send her over the edge into a loud orgasm. When she finally came down Ann said, "Please, you have to tell me what you have planned. The suspense is killing me and I cannot keep my fingers off of myself." I smiled and said, "OK, I will give you a hint. One of the things that will happen to you will be a repeat of something that happened in one of your previous sessions." "Thanks for nothing," Ann said. I could, however, see from the furrows on her brow that she was mentally running through the various things that had happened, trying to figure out which one would be repeated. She continued to think about the possibilities for the next few days and spent more time watching the videos of her previous sessions trying to figure out what I was going to have her repeat doing. This made her even hornier despite her giving me and our many sex toys a thorough workout. The day for Ann to leave finally arrived and I put the new bikini I had bought, her other "hunting clothes" and the sex toys, equipment and condoms that would be needed for her next training session into Ann's luggage. I also included the video camera. I gave Ann the two letters I had prepared. Ann was surprised that there were two letters and I explained that the one in the blue envelope was for her and that she was to open it when she got to her hotel. The first letter would explain when the second letter was to be opened. I gave Ann a deep kiss and helped her with her luggage out to the cab that would take her to the airport. Ann said that she fidgeted the entire trip as her pussy stayed very wet as she contemplated what would soon be happening to her. Ann got to the hotel and checked in to her room. She did not bother to unpack and instead tore open the first letter and read it. Here is what it said: "Well, my dear, the moment of truth has arrived. Your training will be another gang bang but you will be alone this time with the men who will be using you. Neither I nor anyone you know will be there and you will have no choice but to take whatever the men dish out to you. You said you wanted something that would be a challenge so consider yourself challenged. When we set up your first gang bang we talked about how it could be hard for you to get an acceptable group of guys together but I looked at the agenda for your conference and have a solution. You are going to audition the guys one at a time for your gang bang. Your schedule is free Tuesday and Wednesday night as is Thursday afternoon. Those will be the times for the preliminaries and as your schedule is open Friday evening as well, that will be the time of your gangbang. On Tuesday and Wednesday night you are to get dressed in your "hunting" clothes and go out and pick up one man at a time, take him back to your room and let him fuck you and otherwise do whatever he wants to you. On Thursday afternoon you are to put on the bikini that is in your bag and your CFM heels and nothing else and go down to the pool for a hunting session. You are to get the bikini wet as soon as you get to the pool and each time that you return. You are to pick up at least three guys individually during each hunting session. If a man you pick up on one of your hunting sessions makes you cum at least twice you are to invite him to your gangbang. It does not matter if a man makes you do things you do not like or is rough with you. If he makes you come at least twice you must invite him. You are also to tell each man that you invite that he must bring a friend to your gangbang. You can invite men who did not make you cum at least twice and allow men to bring more than one guest but those men and/or guests cannot be instead of a man or guest who otherwise would have been invited. Each hunting session is to be four hours long and consist of three separate assignations. I know you are thinking that is not enough time but it can be done if you are aggressive and make it clear to the guys what you want to happen. You may have to come right out and invite a guy to your room or even say that you need to get fucked. There will also be less time for small talk so the men you select will continue to be mostly strangers. In order to meet the time deadline you must have returned to the place of your meeting with the third guy before the four hours are up. The four hour clock starts when you first walk out of the door of your room. If you do not make the deadline you must pick up an additional guy on that preliminary session. If you wind up with more than one guy during any session each orgasm counts for each guy so, for example, if you cum twice while you are with two guys each guy gets invited and can bring a guest. Multiple guys together count only as a single session of the three. The same rules apply as in your previous training sessions. The guy must allow the session to be videotaped and must wear a condom when he is in your pussy or ass. The guy cannot do anything that would permanently mark or hurt you and water sports and scat are off limits. Other than that the guy can do anything he wants to or with you and all three of your holes are open to him. Other than these limits, once the door to your room closes you cannot refuse or say "no" to anything the guy wants to do. You are to make this clear to the guy when you go over the limits with him. When you have finished a session with a guy you are to get dressed and tell him you want him to take you back to where you met. Hold his hand as you walk back to the spot where you met him and once you get there turn toward him, take the hand you are holding and put it on one of your breasts, on your ass, etc. and give him a deep kiss. Make it clear to anyone that may be watching that you have just fucked the guy. Not sure if you have noticed yet but I packed a bright yellow slinky top and your yellow CFM heels. The color will make you stand out and people will notice you more. The bikini I just bought is much smaller than any you have worn before and the fabric is sheer so it will be almost transparent even before it gets wet. It is likely that you will be even more conspicuous in the bikini because any marks from your sex sessions such as hand prints on your thighs, butt and breasts will be clearly visible. This will be embarrassing and humiliating but remember how turned on you were when you were walking out of the bar with six guys before your first gang bang and you felt as though every eye was on you and you thought that everyone knew you were taking the guys to your room to fuck you. Despite the humiliation you will feel there is an advantage to all of this. Looking recently fucked will make it easier for you to more quickly attract the second and third guy during your hunting sessions as anyone paying attention will notice and your availability and willingness will be obvious. Now three hunting sessions with at least three guys each means a total of at least nine and if each of them gets invited to your gang bang and brings a friend you could be facing a total of 18 guys. I don't think it will come to that because obviously not every guy will make you cum at least twice so you will not invite everyone. Not every guy invited will show up and not every guy who shows up will bring a friend although because the guys should all staying at the conference hotel there may be fewer no-shows than would otherwise be the case. Teaching My Wife Ch. 06 I don't know how many guys you think you can handle but you did tell me before your first gang bang that you had the same equipment as the women in the gang bang videos I had you watch where it was not uncommon for there to be more than a dozen guys and just one woman. You took on six during your first gang bang, eleven during your anal gangbang and three plus a girl in your fraternity adventure so you have some reference. Whatever number there are you will be alone with them and be at their mercy. By having you audition some of the men first you will get some solace because at least some of the men there will be men you at least were comfortable picking up and who did make you cum at least twice. That familiarity is, however, a double edged sword. On the one hand you will know those guys to some extent. On the other hand because they have already had sex with you they will know that they can do what they want and some of them may be more aggressive and demanding of you than they were the first time. The friends they bring are an open question. You will have no choice as to who these men are and they will not have passed the initial screening you used with the men you audition. Basically the guests will simply introduce themselves and then join in fucking and otherwise using you. Other than their name and who invited them you will not know anything about them. There are two sets of toys in your luggage. You are to open the beige bag before the guys start to arrive for your gang bang and put on the contents and your CFM heels. You are not to wear anything else and are to open the door for your guests that way. At 8PM on Friday night you are to open the second letter and read it aloud to the men who will be there for your gangbang. Leave the blue bag of toys out for the men. Of course, you can just decide to call this off if it is too much of a challenge. Smiles." Ann dropped the letter on the bed when she finished reading it and felt the bottom of her stomach fall away. She said that her hands were visibly shaking as she got a drink from the mini-bar. When Ann finished her drink she carefully re-read the letter and said that she trembled even more the second time through it. Ann dialed the phone and when I answered she said, "I just finished reading the letter a second time." "And," I replied. "I don't know if I can do it, the thought of being alone with that many guys scares me." "You don't have to; you can always say that the challenge was too much." "Bastard, I knew you would say that." "Well, it's true; you can always just call it off and enjoy your conference in other ways." "Why didn't you tell me you wanted me to have another gang bang instead of just saying this session would include something that was done in a previous one?" Ann asked. "Now if I told you what was planned it would ruin the surprise, wouldn't it?" I replied knowing that this was not the activity to which I was making reference when I gave Ann my cryptic hint. "Let me think things through and see what is worse, the gangbang and everything associated with it or having you smirking at me because I finally chickened out," Ann responded and we said our goodbyes. I did not hear from Ann until early Tuesday evening when she sent me a picture of herself that she took with her phone. She looked gorgeous and was wearing the yellow top and CFM heels. The message with the picture said, "I made my decision." Ann later told me that she could not believe how conspicuous her yellow top made her look. She said that she thought that almost all eyes were on her when she walked into the hotel lounge and took a seat on one of the bar stools. Ann said that she knew she would have to work fast to pick up her quota of three guys and she immediately started to cross and uncross her legs so that her lack of panties would be evident to the guys that were sitting around her. It did not take long for a guy to notice and soon he was at the bar getting another drink and offering another to Ann as well. His name was Yoshi and he was a Japanese American from the West Coast. Ann said that he was very polite and based on that decided to invite him up to her room. Despite her growing number of adventures, Ann had not had sex with an Asian man before. She said that she found his skin particularly smooth and his thinner pubic hair made his average sized organ look larger than it was. Ann said he fucked her to three nice orgasms before pulling out, taking off the condom and cumming on her face. Ann invited Yoshi to her gang bang and told him to bring a guest. "My two colleagues are travelling with me so I will bring two guests," Yoshi said, "and we will do bukkake." Ann said she was a bit taken aback with her first guy asking to bring an additional guest but because Yoshi was so gentle when he fucked her she told him it would be OK. Yoshi escorted Ann back to the bar and she gave him a deep kiss when they said their goodbyes. She took her place on a bar stool and sent me the following text message; "Yoshi, 3x, p, 2g, btw, wht is bukakee?" Although cryptic I was able to figure out that the guy's name was Yoshi, he had fucked Ann's pussy and made her come three times so he was her first invitee. I was surprised that she had agreed to allow two guests but assumed she had her reasons. I was intrigued that Ann did not know what a bukkake was but as her sexual metamorphosis had only been during the last ten months it made some sense. Even though Ann was getting more receptive to swallowing cum doing so, and having cum on her face, were not among the activities that she found particularly appealing. Not wanting to ruin the surprise of her first bukkake, I sent Ann a longer e-mail talking about things that had happened at work and around our home and ignored her question. Apparently she was busy with other things because about seventy five minutes later I received a message saying: "Chet, 4x, m, p, a." Translated, Chet had fucked her mouth, pussy and ass and made her cum four times so he was also invited to the gang bang. The third and last message of the night came in shortly before the four hour window was to close and read: "Loser, 0x, p, called himself pistolpackinpete, little pistol, fired too soon." Translated, the third guy was not much in the size or stamina department and had not gotten Ann off despite fucking her pussy. That made the total for the first night, five, with two guys and three guests. The session Wednesday evening worked out about the same with two guys making the cut and two guests. When added to Tuesday's number that made it a total of nine if everyone showed up Friday night. Late Wednesday night the phone rang and when I answered it Ann said, "You cannot be serious about me wearing that thing you called a bikini in public." "Aw, come on, you are at an international resort. Lots of the European ladies will be topless at the pool," I replied. "I would be better off naked because the fabric is so sheer you can see every bump on my nipples and if you are within ten feet of me you can see every bit of my pussy," Ann said. "Sounds like good advertising for what you are at the pool to find," I replied. "Look, if wearing the bikini is too much of a challenge just call the whole deal off. Of course, you will have to explain to the guys you already invited to your gang bang why you are calling it off," I continued. "Why do you always make things so hard for me," Ann whimpered. "You were the one who wanted a challenge, the one who taunted me until I agreed to come up with a scenario for you. Just admit you cannot go through with this adventure and I will only call you a 'quitter' and a 'chicken' for, oh, maybe, six or seven years," I countered. I knew that this would push Ann's buttons because she is very determined and even though quitting would be the easy way out Ann's pride would never let her do it. "I hope the hotel throws me out," Ann spat out and hung up. Despite having several drinks during her adventures on Wednesday night Ann set the alarm for early Thursday morning so she could prepare herself to wear the most revealing swimsuit she had ever worn. She shaved her pussy twice and made sure she got around her asshole because the only thing covering it would be the string that went up between her butt cheeks to the string that would go around her waist. When she was done Ann put on more traditional business wear and went to her meetings and seminars. She said that her pussy was extremely wet and that she thought that anyone near her would be able to smell her arousal. Ann knew she would feel humiliated with everything she had to offer essentially on display once she put the bikini on but also said that it turned her on at the same time. Apparently she had gotten over her fear of the hotel throwing her out. Ann finished her last seminar and went back to her room. She stripped off her business wear and stood naked holding the bikini in her hands. The bikini consisted of about three square inches that would cover her pussy and not much more that would cover her breasts and nipples. Because the fabric was sheer and almost transparent, whatever was covered would not be covered that well. Ann put on the bikini and walked in front of the mirror. Her nipples protruded enticingly through the sheer fabric as did the outline of her pussy. Ann trembled as she realized how much of her would be on display at the pool. Another dab of perfume and Ann finally had enough worked up enough courage. She took one more look at her visage in the mirror and flipping her hair back she strode towards the door. Ann opened the door to her room and stepped out into the hall. She said that she felt extremely vulnerable as she walked down the hall to the elevator. The elevator arrived and Ann was happy to see that there was no one on it and she pressed the button for the pool level. Ann exited the elevator and walked out onto the deck surrounding the pool. Ann felt as though everyone was staring at her as she walked over to an empty lounge chair. She stood patiently while a pool attendant put fresh towels on the lounge and took her drink order. She was going to lie down when she remembered that the letter said that she was to get the bikini wet each time she arrived at the pool. Ann slipped off her CFM heels and then made her way over to the shallow end of the pool. Ann walked down the steps and descended into the cool water until it was almost up to her shoulders. Her nipples, which had already been sharp points due to her embarrassment and arousal, hardened further due to the cool water. It seemed like only seconds before a man appeared next to her and started to strike up a conversation. The conversation, for what it was worth, was about her swimsuit and how hot she looked in it. "Would you like a drink," the man, whose name was Jack, asked. "I ordered one before I got into the pool. It should be by my chair now," Ann said. "Great, I will get my drink and join you," Jack replied. He took her by the hand and helped her up the steps and out of the pool. As they started to walk across the deck Ann looked down and saw how transparent her bikini had become due to it being wet. She gulped as her already high level of embarrassment grew. Ann was sure that everyone could see her nipples and pussy. Ann sat down on her lounge and closed her thighs in an attempt to shield her pussy from wandering eyes. Jack sat down on the lounge next to her and they continued to chat. After a few minutes Jack said, "Now I know who you are. You were in the bar last night wearing a yellow top and yellow heels, weren't you?" Ann pleaded guilty and Jack continued, "I was there with a few of my co-workers and was going to come over and try to meet you but it seemed that you were always either coming or going with a different guy on your arm." Ann smiled weakly as she realized that people had noticed her slutty behavior. Knowing that she had to get started to make her quota, Ann decided to be more forward and said, "Would you like to be the one who goes with me now?" Jack readily agreed and Ann explained the rules about videotaping, condoms and the other limits she had. Jack stood up and helped Ann to her feet and into her heels. He put his arm around her waist and let his hand rest on her hip as he escorted her from the pool and into the hotel. As they were walking into the hotel, Ann saw Jack look over at a group of guys and noticed that they were smiling and giving him the thumbs up sign and realized that again people had taken notice of her slutty behavior. While they were waiting for the elevator that Jack pulled Ann towards him, hugged her and kneaded her naked butt cheeks. When they got on the elevator she said that he took one of her nipples between his thumb and forefinger and squeezed it hard enough for her to cry out. Despite her cry, Jack held on to her nipple firmly until the elevator got to Ann's floor. Ann said that she then knew that Jack would be a rough fuck. Jack followed Ann into her room and the door clicked shut. Ann said that every time she heard that sound she would shudder because she knew that her options to say "no" had just become very limited. Ann got the video going and Jack pulled down his swim trunks and pushed Ann to her knees saying, "Start sucking, bitch." Ann took the first couple of inches of Jack's cock into her mouth and reached up with her hands to hold the rest. "No hands," Jack said as he pushed Ann's hands away. "Just use your fucking mouth." Ann redoubled her efforts to satisfy Jack with her mouth but before long he had grabbed her hair and was roughly face fucking her. She sputtered as she tried to keep up with his efforts to force his cock into her throat. Suddenly Jack released his grip on her hair and grasped a nipple in each hand and squeezed and twisted roughly. Ann shrieked around the cock in her mouth and Jack slipped into her throat. Jack released one of her nipples and put that hand at the back of Ann's head keeping his dick lodged deeply in her throat. "Now, milk me with your throat," Jack directed Ann and she did what she could to bring him off. Ann pushed her hands against Jack's thighs trying to dislodge the dick that was now fully in her throat. "Put your hands down," Jack commanded, "that dick stays where it is until you make it cum and you will be sorry if it doesn't." At this point Ann became truly frightened of what Jack might do to her and she decided that she had better get him off as quickly as possible. She started to suck harder and use her tongue on the base of his cock and it seemed to be working as Jack started to moan. Jack continued to hold on to the back of her head keeping his dick wedged as far into her throat as it would go. Jack moans grew louder and Ann knew that he was getting close to cumming. She continued to suck as hard as she could and to use her tongue on the base of his cock. Jack took his right hand off of the back of Ann's head and used it to grab her left nipple. He squeezed it roughly and twisted it as far as it would go. Ann shrieked in pain around his cock and suddenly Jack started to spurt down her throat. As Jack started to soften he told Ann, "Be sure to suck every drop of cum out of my cock." Ann did what he wanted and he finally withdrew from her mouth and wiped his dick dry on her cheeks. "That was good, baby," Jack said, "Now it's my turn to return the favor." Jack helped Ann to her feet and led her over to the bed. "Get rid of the bikini," Jack told Ann and she pulled the top over her shoulders and slid the bottom down her legs. Jack positioned Ann on the bed so that her pussy was right at the edge of the mattress and knelt down in front of her. He spread Ann's nether lips open and put his tongue on her clit. Ann said she was hoping that Jack would not make her cum because she was afraid of him and did not want to have to invite him to her gangbang. Her body, however, betrayed her as Jack no sooner had his lips around her clit sucking the little bud into his mouth when she started to gyrate her hips on the bed. Jack continued his assault on Ann's clit and she held out for only a few more minutes before she came hard on his tongue. One more orgasm and Jack would likely be at her gang bang. Jack spun Ann around on the bed so that her head now hung over the edge. He put his dick into her mouth and said, "Get me hard so I can fuck you." Ann started to minister to his cock and Jack soon began to get hard again. Jack kneaded Ann's tits roughly while she sucked his cock. His handling of her tits was rough enough to redden Ann's tits and leave hand prints so that anyone who saw her tits in their current condition would know that her tits had recently been roughly handled. Jack let Ann suck on his cock for a few minutes before saying, "Do you want me to fuck your pussy or your ass?" "It's your choice," Ann told him before she put her mouth back on his cock. "My wife doesn't let me fuck her ass so it is your ass," Jack told Ann. Ann took her mouth off of his cock long enough to say, "There is some lube over on the dresser." Jack pulled away and got the lube from the dresser. "Lie across my lap and I will get you ready," Jack told Ann. She draped herself over his lap and waited for him to lube her ass. Instead of feeling the cold lube being applied to her asshole Ann felt a sharp sting as Jack brought his hand down on her left butt cheek. "Ow," Ann said both from the pain and the surprise. "Gotta warm up that ass a little bit first," Jack said and he proceeded to give Ann another three hard spanks on each of her butt cheeks. Because Ann knew these spanks were coming she was able to bit her lip and keep silent for the most part with only a "mnffff," escaping every now and then. Ann started to kick her legs and brought her right hand around in an attempt to protect her butt. Jack grabbed her by the wrist and told her to keep her hands where they were. He reminded her that she said he could do anything he wanted to her with a few exceptions and a hard spanking did not fit into any of the exceptions. Hearing this Ann forced herself to calm down and knew that she was in for one of those moments in her adventures where something would happen to her that she did not like but because she had agreed to the session subject only to the specified limits she had no choice. "OK, I am going to give you twenty more on each cheek and you better stay still and not try to protect your butt or I will start over," Jack told Ann. "Do you understand," Jack asked. "Yes," Ann meekly replied. Jack then gave Ann the promised spanks and you could hear a sharp crack each time his hand hit her butt. After the first couple of spanks Ann began to grind pussy against Jack and you could tell she was beginning to get aroused. About half way through Ann started to sob and begged Jack to stop but made no attempt to interfere with the blistering of her butt and kept grinding her pussy against his leg. Jack ignored her pleas and gave her the last ten which seemed even harder than the first ten. Ann convulsed and came on Jack's leg right before he delivered the last two spanks. Ann's ass was now a bright red and you could make out the outline of several hand prints on each cheek. "Wow," Jack said, "you just came while I was spanking you." Ann just sighed and acknowledged that she had and knew that she now had to invite Jack to her gangbang. Picking up the tube of lube Jack squeezed a generous dollop on Ann's ass and worked it inside using one, two and finally three fingers. Jack positioned Ann on the bed in the doggie position, slipped on a condom, lined up his cock with Ann's asshole and pushed his full seven inches to the hilt in one thrust. Teaching My Wife Ch. 06 Ann squealed with the pain of both the invader in her ass and the pain of having Jack's body pushing against her still flaming ass. Jack pulled almost all the way out and then gave Ann another hard thrust. She was better prepared for this one and just grunted when Jack hit home. He got a good rhythm going and sawed in and out of Ann's ass for several minutes. Jack reached around and found her clit with his fingers. Jack rubbed and pinched Ann's clit while he continued to piston his cock in and out of her ass. All of the stimulation proved to be too much for Ann to resist and as she came she exclaimed, "Oh, shit, I'm cumming again." Jack gave her ass a few more strokes and then pulled out, stripped off the condom, got in front of Ann and shot his load in her face and hair. Ann winced as the hot cum hit her face. Ann went to clean up and when she looked at her ass in the mirror saw that it was still red from the spanking Jack had given her and that several of his handprints were still visible. Ann felt mortified because she knew that everyone at the pool would see her ass and know that she, an adult woman, had just been spanked. The marks from Jack's rough handling of her tits had also not faded entirely and Ann tried to adjust the top of her bikini to cover them but there was just too little fabric to work with. Ann glanced once more at her abused ass and tits, took a deep breath to gather herself and took Jack by the hand and led him out of her room. They got to the pool and Jack escorted Ann over to the lounge she had used earlier. Ann reached up and gave Jack a deep kiss and Jack hugged her and kneaded her bare butt while she did. The kiss drew even more attention to Ann and she said that she was sure that everyone at the pool could see the handprints on her ass and her reddened tits and knew that she had just fucked the guy who had abused her body. Ann remembered that she was to go into the pool each time she came to the pool and she quickly slipped off her heels and went over and got into the cool water. Ann thought that the cool water would soothe her marks and would also shield her a bit from the eyes that were focused on her. Because of the limited time Ann had to complete her tasks she could only stay in the pool for a few minutes and eventually made her way back to her lounge. When she got there she found two of Jack's friends waiting for her. The taller one spoke first and said, "I thought I would just come over and see if I could be next." The shorter one said, "I should be next because Jack and I saw you last night at the bar going in and out with different guys and he told me what he did with you in your room." Ann said she was completely humiliated at this point because she thought that everyone within earshot would figure out that "next" meant "next to fuck her." Ann tried to steer the conversation in another direction but the two guys were clearly impatient and looking for a quick fuck so they did not take the bait. As the arguing between the two guys grew in intensity and volume Ann could see that more and more people at the pool were tuning in and paying attention. With her embarrassment mounting Ann just wanted to get away but she knew the only way she could do that was with a guy going back to her room. She also knew that picking one of these guys was not going to be a decision that the other accepted quietly so she took each of the two guys by the hand and said, "Let's go." Assuming that these two guys made her cum at least twice, and they did, Ann had just increased the number of men at her gangbang by four instead of two. Looking at the video later I could see that these two guys gave Ann a real workout using all three of her holes repeatedly. Although they were not gentle they did not treat Ann as roughly as Jack did. Ann got back to the pool with a little less than an hour in which to find and fuck a third guy. As before she first went into the water to make her bikini transparent although she admitted that because she had been exposed for so long she did not even feel embarrassed anymore. Returning to her lounge chair Ann again found another guy waiting for her. "I work with Jack," he said and before he could say anything more Ann took his hand and said, "Come with me." Ann said that she knew that time was running out so she said that she fucked the guy hard and fast and made him cum twice, once in her mouth and once in her pussy. He returned the favor giving Ann the required two orgasms to earn himself and a guest an invitation to the gang bang. "I literally had to drag the guy back to the pool," Ann told me and she made the four hour deadline with only minutes to spare. With the time pressure Ann had not been able to send me any messages as to what had happened Wednesday or Thursday. She brought me up to date on Thursday when we spoke and I was surprised that the total had reached 17. Ann was now facing a gang bang in which she would be the only woman with as many as 17 guys, all of them virtual strangers. Ann was going to pull a train and it was going to be a long one. "Are you sure you want to go through with this?" I asked Ann pointing out that because they guys were all staying at the hotel it was unlikely that any would drop out due to family commitments, etc. "I thought I had to because I already started," Ann replied. "Normally that would be the case but in the past you had only one session with the man or men and you could decide not to go ahead at anytime up to when the door of your room clicked shut and then you could only say "no" in very limited circumstances. Here even though you have already recruited the men for your gang bang it has not started," I explained. "What's the matter, afraid that I will handle your challenges?" Ann taunted. "No, I just wanted to be sure you understood your options." "I admit that I am still apprehensive because there will be a lot of men and I will be alone and at their mercy but my pussy just oozes when I realize that once I start I will have to fuck and suck and otherwise perform until every guy is satisfied. Besides, I plan to fuck their brains out and be wanting more when there are no guys left who can still get it up." "Be careful about having your words write checks your sexy little body will have to cash," I said. "Want me to at least tell you what the second letter says," I asked. "Don't you dare. When this started weeks ago I was dying to know what was going to happen to me. But now I know that it is going to be a gang bang and that I am going to be standing virtually naked in front of a group of guys reading a letter that tells them how they are to use and abuse me. I just cannot get that image out of my mind and know that my hands will be shaking and voice breaking as I learn my fate." "There will be some surprises and some things you will not like doing in the letter," I told Ann. "Aren't there always?" she replied. "By the way, I ordered a party set up for your guests, mostly liquid refreshments. It will help lower their inhibitions and make things more interesting for you," I said to Ann. "You're so sweet, you think of everything," she replied sarcastically. We talked for a few minutes about other things and Ann said that she would call me when her adventure was over, likely sometime Saturday morning. Ann said that she slept fitfully Thursday night and woke up several times to the image of her reading the letter to her gang bang crew. Her last seminar ended at 1:00PM on Friday and she went back to her suite to prepare for the night's adventure. She used her Jacuzzi tub for about an hour and then took a short nap. She awoke to find that it was about 5:30PM, or less than two hours until her guys began to arrive. When she issued the invitations she told the guys to plan to arrive around 7:30PM but that the main event would not start until eight. Even though she had done it the day before prior to donning her new bikini Ann shaved her pussy and legs leaving her silky smooth. She applied body lotion and did her hair and make-up to perfection. She knew that soon after her gang bang started that she would be a mess but wanted to at least start looking her best. When she was finished she put on the hotel robe and waited. Around 7:00PM room service delivered the party set up I had ordered. Ann had the guy set it up in the sitting room part of her suite. She said that when she saw bottle after bottle of scotch, gin, vodka, whisky, etc. she knew that the men would not be thirsty and would likely be less reticent about using her. When the room service guy left Ann decided to finish getting ready and opened the beige bag I had put in her luggage. According to the first letter, Ann was to wear only the contents of the beige bag and her CFM heels for her gang bang. Ann gasped when she saw what was in the bag. There was a set of leather cuffs for her wrists and a set for her ankles. There was also a larger set to go around her thighs just above her knees. The final items were a wide leather belt that went around her waist and a matching collar for her neck. Each of the items had metal loops through which ropes could be run and clips that allowed the items to be joined together. Ann said that she knew that if she greeted the guys wearing these bondage items that she would likely spend a good portion of the night restrained in some fashion. Even though she could still call things off she knew that she could not do so without causing at least a bit of a scene and when she glanced over at the desk and saw the second letter she knew that she had to feel what it would be like to be reading it aloud before a group of guys. She put on the leather items buckling each tightly. Ann checked the beige bag again to be sure it was empty and found several lengths of rope that she took out and lay on the desk next to the letter, the video camera and the second blue bag of toys. She went to the closet and put on her CFM heels. Ann sat down to wait. She did not have to wait long as at 7:30PM there was a knock on the door and she opened to admit the first two guys who would be fucking her that evening. One had fucked her earlier in the week and the other was his guest. They were astonished and delighted with how Ann was "dressed" and ran their hands over her naked body as she showed them to the bar. Ann shuddered as she suddenly realized that a man she had not even met had already seen her naked and rubbed his hands over her breasts and ass. She also knew that he would not be the first total stranger to do that and more to her tonight. This was when the reality of her situation finally hit Ann. Unlike her previous adventures, where she had time to flirt and chat with her soon to be lovers, this time she had to work fast to fit three guys in (pun intended) within the four hour periods for her hunting sessions. There had not been as much time for verbal foreplay as it were and with Jack's friends on Thursday at the pool there was no conversation, just let's get up to my room before I get even more embarrassed. Ann realized that even though she had already fucked at least half of the men who would be here tonight that she really knew very little about any of them. She knew that she would know nothing about the guests they would bring. That meant that she really would be getting gang banged by a room full of strangers and would be utterly alone and at their mercy while it happened. When we had first talked about having Ann do a gang bang she said that her biggest fear was being alone with a group of strangers who would try to one up each other in how hard they used and abused her. She said she had visions of being fucked by one guy while the others cheered and urged him on to, "Fuck her harder," and when that guy was done trying to fuck her even harder to prove they could do better. As these thoughts ran through Ann's mind her fear increased exponentially and despite the air conditioning running full blast a sheen of nervous perspiration soon covered her naked body making it even shinier that it was from the body lotion she had used. At the same time Ann later told me her lust also seemed to go off the chart and she said she could not believe that her pussy became even wetter. Ann's thoughts were interrupted by a knock on the door and Yoshi and his two colleagues were next to arrive. They had trouble bowing to Ann because they could not take their eyes off of her naked form. These men also passed their hands over Ann as they entered her room and did not introduce themselves until they were inside. Ann had again been manhandled by men whose names she did not even know. Jack and his co-workers and their guests were next and Ann watched as a group of ten guys piled into her suite. They were boisterous and Ann felt many hands on, and fingers in, her body for what would be the first of many times this night. A few minutes later one more guy arrived and explained that his guest had to go back home due to a business emergency. That made it a total of 16 guys milling about and drinking in Ann's suite and as she had invited 17 the turnout was pretty impressive and meant that she would have a lot of fucking and sucking to do as the night wore on. Despite knowing that no other guests were expected Ann waited until 8PM because that was the time we had decided would be the equivalent of the door clicking shut in her previous sessions. At a little after 8PM, Ann herded everyone into the sitting room part of her suite and got them quieted down as best she could considering that more than one of them had had a couple of drinks already and some in Jack's group appeared to have had a few before they arrived. She got her glasses and put them on. The glasses actually made her look even sexier. Picture a hot school librarian naked and dressed in bondage gear and heels. Ann said that she was nervous and the feelings of fear and lust were overwhelming. She said that she could see her own juices leaking out of her exposed pussy and onto her thighs. With trembling hands Ann opened the letter and announced to the assembled guys that it was from her husband. She started to read the letter aloud in a quiet voice: "The woman standing before you is my wife, Ann. Up until 10 months ago she was your typical unassuming wife in a monogamous relationship and with not much prior sexual experience. Like many of you I was long tired of the same old, same old and began to pressure Ann to open her sexual horizons. She eventually agreed and started out by having sex sessions with guys she picked up on her business trips. For each session I prepared a letter like this one that outlined what the man or men were to do to Ann. At first Ann was a reluctant participant but somewhere after her first gang bang with six guys it was if a dam burst. Ann began to crave her adventures and to dare me to come up with more and more challenging scenarios for her. That is why all of you are here; tonight you are Ann's challenge. The rules are simple. The entire session is to be videotaped and one of you should follow the action at all times with the camera. Safe sex is required and if you are in Ann's ass or pussy you must be wearing a condom. No scat or water sports and nothing that would permanently mark or injure Ann. You cannot invite any additional men to join the party once it starts and the party is over when the last of you has decided he has had enough. All activities must take place in Ann's room. Other than that Ann is yours to use however you see fit. If Ann refuses to do something you want to do you are free to force her to do it. She will sometimes complain, whimper and bargain to try to talk you out of things she may find objectionable but just ignore her. She understands that her right to say "no" except for violations of the rules ended at 8PM. Like I had up until 10 months ago many of you probably have wives and girlfriends who deny you sexual activities you would like to do. Well, here is your chance. You can take out all of your frustrations of those denials on Ann. You are free to use Ann's mouth, pussy and ass and can do so singly or in double and triple penetration. For each of Ann's previous adventures I also listed in the letters a few specific things that should be done to her and here they are for this adventure: 1) Ann has not experienced having two dicks in her mouth at the same time or in having double vaginal intercourse. You should make sure that she does both before the night is over. 2) In the weeks before this adventure Ann pestered me to find out what I had planned for her. I gave her a hint saying that one of the activities would be something that had happened before. When she learned that I had planned her second gang bang she thought that was the repeat but it isn't. During her first gang bang the guys made Ann suck them until they came in her mouth and then had her spit their cum into a water glass. When all of their cum was in the glass they forced Ann to drink it by putting binder clips on her nipples until the pain became unbearable and she did what they wanted." Ann's hands started to shake even more as she read this part of the letter and her throat became dry making it even harder for her to get her words out. "Please," she said, "don't make me do that." Ann looked out plaintively at the assembled men and saw that no one was going to speak up to tell her she would not have to do it. She kept looking out looking for some support when someone said, "Finish the letter so we can get started." Tears welled up in Ann's eyes as she returned to the letter: "Tonight whenever any of you cums in Ann's mouth you are to make her spit it out into a glass. Whenever any of you cums in a condom you are to drain the condom into the glass as well. When you think there is enough cum in the glass give it to Ann and tell her to drink it. If she refuses there is a ball gag with a breathing tube through it and a funnel in the blue bag Ann has left out somewhere. Force the gag into her mouth, tighten the strap behind her head and attach the funnel. Hold or restrain Ann on her back and pour the cum into the funnel. Otherwise do what you want and be sure that you use Ann to the max. She wanted a challenge so give it to her." Ann dropped the letter on the desk and just stood there silently with a tear running down her left cheek for a few moments. She said her mind was racing thinking that she should have called things off and been less arrogant in demanding a challenging scenario but she knew that she now had to live with the consequences of her decision. She did not stand there alone for long. In a few moments Jack and his group surrounded her. Jack ran his hands over her breasts and pussy. In one quick motion he slipped two fingers into Ann's cunt and when he felt how wet she was announced that fact loudly. Jack fingered Ann a few times and she grabbed onto his arm and held on. In another few seconds her mouth opened and she moaned as she came for the first time that night. Ann's moans brought cheers and applause from many of the guys and one of them said, "Sounds like this bitch is ready." Two of the guys with Jack led Ann over to a table and laid her across it on her stomach with her pussy on one side and her head on the other. Within seconds a guy was buried balls deep in her cunt and another was deep in her throat. Ann had not fully come down from her first orgasm and the cocks hammering away at her pussy and mouth soon had her over the edge and as she came a second time she gurgled her cries of pleasure around the cock that was in her throat. This set off the guy whose cock she was sucking and he fired his load deep into her throat. There would be no cum to spit out.