0 comments/ 142181 views/ 17 favorites Rachel's Dilemma By: bondmaster I had been dating Rachel for 3 month when she told me of her dilemma. She had received an offer from her ex-husband. He was extremely wealthy. He made his money during the PC revolution. Anyway, during the divorce, she got screwed. He hired expensive lawyers and left her penniless. Her ex had heard she finally had boyfriend. And he was ready to make a deal. Money for pain. Rachel had hurt him badly and now he wanted retribution. He was willing to give her the money she wanted if she would be willing to be punished. BY ME! He had called her and told her he would be willing to renegotiate their divorce agreement. He would be willing to give her 1 million dollars if she would accept 1 hour of punishment per day for the next year. Now I was in the middle! She wanted to do it. I didn't. She said it was an opportunity to get what she deserved. I said it could destroy our relationship! Her ex sent a first class airline ticket to London for me if she was interested. I went to London! He told what he wanted and that all sessions would be video-taped so he would know what he was buying. I told him he could dictate to her but not to me. He could determine what she wore and the punishment plan, but I was responsible for the actual punishment. We agreed. He gave me 3 bags; one contained clothes for Rachel to wear during her punishment, one contained sophisticated video equipment and one contained implements of punishment; whips, paddles, clamps and various other devices I wasn't sure about. I prayed I wouldn't get stopped at customs. I returned to Rachel and again voiced my disapproval. I described his plan to her. Each day, we would video me punishing her for 1 hour. She would do whatever I commanded her. At the end of each month, she would receive a check for $100,000. She agreed. Rachel has a classic hour-glass figure…big tits, thin waist, wide hips and a big ass that was going to be a lot of fun to spank. She was very self-conscious of her wide caboose and always wore loose fitting skirts or pants. She also knew that her large tits attracted men like moths to light. She always wore tight tops which were usually low cut. She had a overactive libido, always wanting me to do her. Her ex-husband knew she used her tits to attract men and his plan for her punishment paid special attention to them. At least half of each session was devoted to punishing her big breasts. The deal was finalized. The money was put in escrow. She would be my slave for 1 hour each day. I would receive an email each day describing the plan for that day's punishment session. Rachel unpacked the bag of clothes while I set up the video equipment. When I finished, I went to review the clothes. Her ex definitely wanted her to be dressed like a slut for her punishment! The clothes were all tight with the tops low cut and revealing and the skirts very short and revealing. To complete the outfits, there were garter belts, stockings and several pairs of 4 to 5" pumps. Rachel had a distressed look on her face. We went through the toy bag together. I figured she should know what she was getting into. It contained several leather whips including one small one, two wooden paddles, a riding crop, a large wooden hair brush, a wooden spoon and a long, heavy metal spatula, several pairs of alligator clips, several boxes of binder clips of varying sizes, a pair of pliers, two adjustable vice wrenches and a bag of wooden clothespins. It also contained wrist and ankle cuffs and several coils of rope. Rachel was white as a sheet. I tried one final time to dissuade her although I secretly wanted her to do it now. "No," she said, "I need this money. Besides, I might even enjoy it." We begin. The email from her ex stated she was to wear a tight, very short and very low cut black dress with spaghetti straps and black stockings with 5" black heels. I told her and she went to change. While she went to dress, I reviewed the rest of the email. I was to begin by whipping her tits. Then the alligator clips were to be clamped on her nipples while I gave her a hand spanking. Next, her tits were to be punished with the riding crop. Finally, her pussy was to be whipped. I didn't share this part of the email with Rachel. I wanted her punishment sessions to be a surprise. I made a final check of the video equipment. Finally, after nearly an hour, she entered the room. She took my breath away. The outfit made her look more naked then if she actually was. Her large tits were barely covered as the dress was open in front to her navel. I noticed with amusement that her nipples were already hard, pushing on the thin fabric of the dress. She had done her makeup to perfectly compliment her outfit. All in all, she looked like a very sexy slut. Before we started, I told her if at any point she could not go on, she should simply say 'monkey' and it would all be over. I turned on the video camera. "OK Rachel, your first punishment session will begin now," I said. "Place your hands behind your head." She looked at me with a puzzled expression on her face but complied. "Rachel, for the next hour, you will be my slave. You will do everything I tell you to do immediately and without question. You will not speak unless ordered to do so. When you do speak, you will address me as Master or Sir," I finished. "You are going a bit over the top, don't you think?" she said. "These are the rules for your punishment sessions. If you question me again, your punishment tonight will be extended to 2 hours," I replied sternly. Her face showed concern and a little fear. I knew she was wondering what she had gotten herself into. However, all she said was, "Yes Sir." I walked over to her, grabbed her hair and pulled her head back. "That's a good slave." Then I released her hair and took her nipples between my thumb and forefingers and pinched them hard. "Aggghhh," she moaned. I pinched and pulled and twisted her engorged nipples for several minutes. By the time I finished, she was moaning loudly and gyrating her hips. Her eyes had glazed over. Was she enjoying this? It was hard to tell. I knew one sure way to find out but decided to wait awhile before venturing there. I released her nipples and took a step back to admire her. Her nipples were rock hard and fully an inch long. "Hands at you sides," I commanded. She complied immediately. I took the straps of the dress and slid them down off her shoulders exposing her large, white breasts. The contrast to the rest of her well tanned body was dramatic. Soon I knew those white tits would sport red stripes. "Put your hands back behind your head," I ordered. Slowly, hesitantly she did as she was told. It was then she realized that her tits were about to receive more punishment. I went over to the table with the implements on it and selected the small whip. It was all leather with a braided handle attached to 4 thin thongs. I returned to her and took the whip in my right hand grabbing the thongs with my left hand. I brought in up to shoulder height and flicked my right wrist down as I released the thongs. CRACK. The whip came down on her left breast leaving a red mark. I repeated the process another nine times hitting different spots on the top of her left tit. By the tenth stroke, there was a nice red glow. I repeated the process to her right breast. This done, I grabbed one of her breasts and squeezed hard. Again, the process was repeated to the other breast. Next, I used a sidearm motion to whip the side of her large tits. Ten stokes to the right and using a backhand motion, ten to the left. By the time I had completed these punishment, Rachel was crying and screamed with each new stroke. I now took her left nipple between the thumb and forefinger of my left hand and used it to lift her breast. With an upward flick of my wrist, I whipped the underside of her breast. She yelped. Ten on each breast. Finally, I again grabbed the thongs of the whip in my left hand and with the whip slightly lower, let if fly. THWACK. The thongs of the whip landed direct on her already sore and swollen nipple. She moaned. Twenty times I whipped her left nipple and twenty times I whipped the right nipple. Again, I took a couple of steps back to admire her. Her tits were well used and abused with several many red stripes. And her poor nipples were purple. And they were about to be abused further. I went to the implement table, dropped the whip and picked up the two alligator clips. Squeezing the handles together for the first time, I realized that the spring was very tight. The wicked looking teeth on the jaws were going to dig deep into her swollen areola. I returned to her and cruelly showed her what I had in my hands. Her eyes grew wide as she recognized my intention.. "Oh no, I can't take that," she cried. I reached out and slapped her right breast hard. "I told you not to speak unless you were told," I scolded. Then I slapped her left breast. She cried out more in horror of what was about to come. I again grabbed one of her nipples with the thumb and forefinger of my left hand and pinched it. With my right hand, I squeezed the handles of the alligator clip opening the cruel looking jaws, placed the jaws over the nipple and slowly released my grip on the handles. She began screaming when I was only half done and began shaking her breasts madly when I had completely released the little torture device trying to throw it off. Quickly though, she realized that this only increased her agony. I grabbed the other nipple and quickly snapped on the other clip. She howled again. After several minutes, she composed herself. I decided to test this new found composure. Quick as a snake, I shot my hand out and flick both clips. She jumped in pain and cried out again. Then she turned trying to shield her breasts from me. I grabbed one of the clips and pulled her straight. "OWWWWWW," she screamed. "Don't try to pull away from me or your punishment will be much worse," I said. I left her to ponder this while I went into the kitchen to get a glass of water. This was thirsty work. I returned to find her with her eyes closed. "You will be happy to know that we are finished with your tits for now," I said. "I want you to go over and stand in front of the dining room table." Very slowly she walked over to the table so as not to shake her tortured tits least they hurt more. Once she was there, I followed and stood behind her. "Spread your legs," I commanded. She moved here legs about two feet apart. I gave her ass a hard swat and said, "Wider!" Quickly she spread then further apart. "Now bend over the table," I said. She slowly bent at the waist, moaning as she did because her tits were now hanging down. I put a hand in her back and pushed her down until here tits were pushed flat by the table. She screamed as the alligator clips dug in deeper when they made contact with the wooden table. She struggled to raise herself off the table but my hand easily kept her in position. The combination of her legs spread wide and the obscenely short skirt caused her entire ass and pussy to be exposed when she bent over. Now was the opportune time to see if she was enjoying this. I took my index finger and ran it along her cunt. It was soaked. The slut was turned on like I had never seem her before. She was literally dripping. When she felt the contact with her pussy, she pushed her hips back trying to bury my finger deep. But I was too quick for her as I retracted my finger and gave her another hard swat on her now exposed and vulnerable ass. "This is punishment, slut. If you are very good and take you punishment like a good slut, maybe I will permit you pleasure when we are done," I said looking into the camera with an evil grin. Let the bastard suffer a little at the thought of me banging his ex-wife when this was over. "Now it is time for a good old fashion spanking, slave," I said. With that, I drew back my hand and brought it down hard on her large ass. It jiggled nicely and left a nice red hand print. I began to spank hard and fast. Soon she was crying again as another part of her anatomy was punished. Again and again my hand landed on her vulnerable ass. Soon she was gyrating her hips in a vain attempt to relieve the burning. I gave her about 300 swats although to be honest I lost count early on. Suffice it to say, I didn't stop spanking her until I couldn't lift my arm anymore and my hand was really sore. I made a note to talk with her ex about coupling hand spankings with paddling or whipping in the future. When I could spank no further, I roughly rubbed her ass. It was very hot to the touch and extremely red. My fingers wandered down to her pussy and I found her clit rock hard. Again, she tried to buck her hips in order to plunge my finger inside. Again, I anticipated her move and she received several hard swat on her thighs for her trouble. "Alright slut, stand up," I said. Slowly without removing her hands from behind her head, she stood up straight. "Turn around," I commanded as I walked over to the implement table and retrieved the riding crop. Again, I showed her the next instrument of her pain and saw a look of panic come over her when she realized the probable target. I was sure I was going to hear 'monkey' in the next moment. But I didn't. I reached out and removed the alligator clips from her nipples. As the blood began to return to her tortured nubs, she screamed in pain. When the waves of pain subsided, I swung the crop and landed it on the top of her breast. Ten to the top of each breast, ten to the side and ten to the bottom. The first one that landed on her poor nipple caused her to scream again. Again, I thought I might hear the safeword but no. Twenty stokes to each nipple and she nearly collapsed to the floor when it was over. I gave her a minute to compose herself. The hour was nearly up and I needed to complete her punishment. I went to the implement table and retrieved the small whip. "Sit on the table," I commanded. Somewhat confused and unsure of what was coming next, she hopped onto the table. The minute her sore, red ass touched the table, she jumped. "Now lay back," I said. She did as I commanded still confused and a little concerned. "Now raise your legs and grab your ankles." Suddenly, she realized what was in store for her. "Noooo," she squealed. I gave her ass a few good, hard swats. "You will receive fifty lashes on your pussy. Forty as you are and for the last ten, you will spread your cunt lips wide so I can punish your clit." "Oh please, haven't I had enough?" "This is the last of it," I said sympathetically. I moved in front of her and without hesitation, raised the whip and brought it down on her exposed cunt. She cried out but held her position. I landed the whip there again and again. She wriggled and squirmed and cried. Finally I was done except for the last ten. "Now, I want you to reach your hands down and spread you lips," I commanded with a stern voice. With a resigned look on her face, she placed one hand on the back of each thigh and spread her cunt wide with her index fingers. Taking careful aim, I landed the whip square on her hard, throbbing clit. She screamed but held on. Again I landed the whip on her clit. Again she screamed. After three more licks on her clit, Rachel began to convulse wildly. She was cumming. Quickly, I landed five more directly on her exposed clit. She continued to convulse for the next several minutes as wave after wave rolled over her. Her punishment complete, I quickly went to turn off the video camera. I needed release and I would be damned if that rich bastard was going to get any more than he paid for. I quickly stripped off my clothes and shoved by pulsating cock into her sore pussy. She screamed and we both exploded together in an incredible orgasm. Rachel's Dilemma Ch. 2 When I arrived home the following day, there was a package waiting for me. I opened the package to find two items; an old-fashioned clothes hanger designed for a woman's suit and weights. The hanger was wooden with a metal rod going across the bottom. The rod had two spring clamps on it from which to hang a skirt. The clamps could be moved along the rod to adjust their position. The spring clamps were very tight so even heavy wool skirts would be securely fastened. The other item was a small bungee cord with the standard hook at one end and weights attached to the other. It must have weighed 2 pounds at least. I had a good idea what these devices were to be used for and got hard just thinking about it in spite of myself. Rachel's poor tits were in for another long evening! I then went over to my PC to retrieve my email. The first one was from Rachel's ex-husband. Here is what it said: The slut is to wear the white cocktail dress with white stocking and the 5" white pumps. Her punishment will begin by having her tits spanked with a hairbrush. The hairbrush will then be used to spank her ass and inner thighs. Next, the suit hanger will be attached to her nipples and the weights hung from the hanger. Standing with her legs spread wide, her pussy will be whipped. Finally, with the hanger still attached, her tits will be whipped. I could feel my excitement mount as I read this. When I had agreed to this little arrangement, I had not planned on getting turned-on by punishing my beautiful and sexy girlfriend. Was I weird? I had certainly heard about guys who got turned-on by causing women pain. But I had never been one of them! But here I was, excited and hard just thinking about my next punishment session with Rachel. I called Rachel and told her I would be over in an hour to begin the session and relayed the dress code. A little over an hour later, I rang her doorbell. She opened the door and took my breath away. She was stunning. The tight, low cut dress displayed her large, luscious tits perfectly. The tight skirt came to just above her ankles but was slit up to her waist on both sides. Each step she took gave me a great view of her stocking covered legs. And since she was not wearing panties, her ass swayed and jiggled invitingly as she led me into the dining room. Her make-up was done perfectly to accentuate her natural beauty. "Go stand by the dining table," I commanded. I went to the implement table and deposited my new toys then went over to the video equipment and started recording. I then went over to my willing victim. "Hands behind your head," I told her. As she did this, I ask, "How are your nipples feeling today?" "They are a little sore," she replied. I reached out and slapped each of her breasts hard. She gasped. "They are a little sore, SIR!" I said. ""They are a little sore, SIR!" she repeated demurely. "Well, they are about to get a lot more sore," I said. With that, I grabbed each of her nipples between my thumb and forefinger and pinched them hard. "Aggghhhh," she groaned. Again, as with the first session, I spent the next five minutes twisting, pinching and pulling her nipples eliciting moans of pleasure/pain. Releasing her nipples, I commanded, "Remove your dress and then return your hands behind your head." I went over to the implement table and retrieved the large, wooden hairbrush. It was an impressive instrument, wide and heavy. I turned and saw Rachel clad only in white stockings and heels. Gorgeous. Her large tits stood out proudly topped by rock hard nipples. "Spread your legs," I demanded. As she meekly complied, I was treated to a nice, clear view of her pussy lips peeking out from beneath her triangle of hair. I grabbed one of her nipples and twisted it cruelly. "Are you excited, slut?" I asked. "No, it hurts!" she exclaimed. With a smile on my face, I said, "Then your pussy won't be dripping like last night, right?" She didn't answer. I'm sure she knew how wet she was. I confirmed it by running my index finger over her pussy. It came away drenched as expected. "You enjoy having you tits punished, I see. Well, you will be beside yourself by the time this nights work is complete." With that, I whacked the side of her left breast hard with the hairbrush. I followed this up with several more swats in the same spot. I then smacked the right breast several times. By the time this little warm up was done, she was moaning loudly with her eyes closed. I moved to stand beside her and landed the hairbrush smack in the middle of her large tit. I continued whacking her breasts and engorged nipples with the hairbrush for several more minutes. Now she was crying out with each stroke. "OK slut, turn around and bend over the table. Your ass needs a little attention," I said. She did as she was told but I was not satisfied. I gave her a whack all my strength. She jumped off the table. "Owwwww!" she screamed. "Spread your legs, slut," I commanded. Rachel spread her legs but again, not to my satisfaction. I whacked her inner thigh hard. "Oh god that hurts," she cried. "Spread your legs wider slut. I want to see your cute little asshole which I plan to fuck good tonight after I finish punishing your sexy body," I said. Reluctantly, she spread her legs wide so her pussy was wide open and her anus peeked out. "Good girl! Now I think you need a good, old-fashioned paddling." And so, I started to spank her ass hard and fast with the cruel hairbrush. I landed the hairbrush ten or fifteen times in the same spot and then would move to the other cheek. Over and over I landed that brush on her ass. Rachel's reaction went from moaning to crying to screaming as her ass went from pink to red to scarlet. Once I was satisfied with the condition of her ass, I moved down to the sensitive area on the back of the thighs. The hairbrush made quick work of this area. Before long, they were also an angry red color on both sides. "Alright Rachel, now I want you to get up and sit on the table." She stood up and turned around and her tear stained face was a mixture of pain and pure lust. She very carefully got up on the table. Sitting on the solid oak surface on her battered butt must have been pure agony. "Good slut. Now I want you to place the bottom of your feet together," I said with a cruel smile. She looked at me with horror on her face. I think my beautiful slut thought I was going to spank her vulnerable cunt with the nasty hairbrush. But no, the pussy punishment would have to wait. My current target was her creamy white inner thighs. I raised the heavy brush and brought it down hard on her right inner thigh. She howled and immediately closed her legs. Annoyed that she moved form her position, I slammed the hairbrush on each breast. "Get back into position and if you move again, I will tie your legs down and use the hairbrush bristle side up on your pussy after I've finished with your thighs," I commanded with another whack on her tit with the bristles of the hairbrush. "Owwww," she screamed. And quickly she returned her legs to their position. I noticed with satisfaction that her right thigh was pink where the hairbrush had landed. I knew she was going to have a very difficult time holding this position as I paddled her sensitive inner thighs. Well, she was the one who wanted this, not me (although I certainly was enjoying myself). WHACK. I brought the hairbrush down on her other thigh. WHACK. WHACK. WHACK. I continued paddling her poor thighs. After about 5 minutes of this treatment, she was begging me to stop. "Oh, pleaseeeeee stop. I can't take anymore," she begged. Indeed, her thighs were an angry shade of red and very hot to the touch. Even though I thought she had enough, I was determined to continue a little longer so she didn't think her pleas were effective. I landed about ten more swats on each thigh. By the time I had finished, she was screaming in agony. To give her a few minutes to calm down and get control of herself, I went into the kitchen to get a drink of water. Returning about five minutes later, she was still sitting with her legs wide apart. The screaming and crying had stopped and she had calmed down. I went to the implements table, dropped the hairbrush and picked up the coat hanger and weights. Looking over my shoulder, I commanded, "Alright, Rachel. Stand up with your hands behind your head and your legs spread wide." She slowly got off the table and obeyed. I turned and approached her carrying the hanger and weights, watching her closely for her reaction. At first, she just stared at the stuff in my hand with a confused look on her face. Then, as she realized what was about to happen, she cried, "Noooooo. Please, Peter, you can't be serious." I reached out quickly and slapped her tits hard with my free hand several times. "I don't want to have to tell you again, slut. You will address me as Master." Then, without waiting for a reply, I grabbed her right nipple, pinched it tight to get it hard and quickly slipped one of the clamps from the hanger over it and released. She moaned loudly as the tight clamp crushed her sensitive areola. I slid the other clamp so that it lined up with her other nipple and quickly clamped it. Her moaning grew louder. I pulled the hanger away from her, stretching her nipples cruelly. "Nooooooo," she screamed again. "Oh, you want me to stop?" I asked. I let go of the hanger. The heavy wooden hanger dropped yanking her nipples down. She yelped. I then held up the weights for her to get a good look at. "Guess where these go," I teased. "Oh Master, haven't I had enough?" she whined. "I don't make the rules in this game, sweetness. I am just the hired help, remember?" "You certainly seem to be enjoying yourself," she spat. "There is no law that says a man can't enjoy his work," I said. I hooked the weights on the hook of the hanger and let go slowly. When I was no longer supporting the weight, her poor nipples were being pulled downward in a most painful fashion. "Oh, my poor breasts," she cried. I lifted the weights a little. "I must agree with your ex-husband. You use your beautiful tits to get your own way. Therefore, it is only fitting that they be punished severely." With that, I dropped the weights. "Aggggghhhhhh," she screamed. "OK, I'll leave your tits alone for now. It's time to whip your pussy." I returned to the implement table and selected a leather whip with 4 braided thongs. I returned to her, whip in hand. "Now Rachel, I want you to spread your legs wider," I said quietly. She slid them a few inches further apart. With my arm hanging down, I brought the whip up sharply with a flick of my wrist. The leather thongs whipped her exposed and spread cunt. She jumped and then howled as her tits bounced and suit hanger and weights bounced with them. "Oh my tits!" she wailed. "Interesting. I am whipping your pussy and you complain about your tits. Well, I'll let you in on a little secret. Once I am done whipping your cunt, I am going to finish by whipping your tits," I said cruelly. She looked up at me in horror even as I flicked my wrist again. Again she jumped a little and again the movement was enough to cause the weighted hanger to bounce further torturing her nipples. As I continued to whip her pussy hard, she tried hard not to move. Towards the end, the pain to her pussy got the better of her and she jumped, trying unsuccessfully to ignore the pain it caused her tits. After about 30 strokes, I stopped. I went over to her and roughly fingered her newly punished pussy. Again she jumped, both in pain and lust. Her cunt was dripping and her clit was rock hard. When my fingers ran over her clit, she bucked her hips trying to increase the pressure. I immediately removed my hand. "Your pleasure needs to wait. It's time to finish. And, like last night, we finish off by whipping your tits. Unfortunately for you, your ex specified that this whipping was to be done with this device still attached," I said I indicating the coat hanger clamped to her nipples. Teasingly, I flicked the whip at the weights causing them to bounce slightly. Each time they came back down, she moaned loudly. I noticed that her eyes were closed. Did she not want to see the whip striking her already red and sore tits or was she turned-on? I raised the whip and brought it down on her right breast. A loud moan escaped her beautiful lips as she thrust her hips out. I brought the whip down on her left breast and again she thrust out her hips like she was trying to fuck something. I repeated this process a few more times but I was so hard and excited myself, I needed to get this done so I could get relief. I moved to her side and brought the whip across her tits, the leather thongs striking both her nipples simultaneously. After a few more of these, Rachel suddenly began convulsing and gyrating wildly. I couldn't believe my eyes. She was having an orgasm. Again and again the convulsions ran through her body as I continued to whip her tits. Finally, I could not take anymore. I dropped the whip and quickly went over to the video camera and shut it off. "On your knees, slut," I commanded. "But the session is over," she protested. I lifted the weights hanging from the hanger and dropped them. Rachel screamed. "It is over when I say it is over. Now get on you knees." She quickly complied to my demand. I slowly undressed as she watched, mesmerized. When I was completely naked, my hard cock stood proudly erect. My lovely slave/slut was staring right at it, licking her lips. I took a step closer and before I knew what was happening, she had the entire length of my hardness in her mouth. Soon, I came like a volcano erupting. I discharged so much cum that Rachel could not swallow it fast enough and it dribbled down her chin and onto her breasts. When I was done, I told my lovely girlfriend to stand and I removed the suit hanger from her nipples. As the blood returned to her deprived nipples, she experienced a new wave of pain. The fact that I was pinching them to get the blood circulating again only stimulated her more. Before I was done, she was moaning and thrusting her pussy out again. It was going to be a long, erotic night! Rachel's Dilemma Ch. 3 This is the continuing story of my luscious girlfriend's bizarre deal with her ex-husband. In a nutshell, he would pay her one million dollars if she allowed me to punish and torture her for a year. He provided all the props, instructed me on what to do and each session was videotaped so he could verify it was done. If you haven't already done so, you really must read the first two chapters before reading this story. In the past two days, my life has been irrevocably changed. As the result of a deal my beautiful and sexy girlfriend made with her ex-husband, I was punishing her per his instructions. What surprised and confused me was that I enjoyed it. I really got turned-on by torturing her big tits, spanking her ass and whipping her pussy. Before this began, I pictured myself as a fairly normal guy who loved normal sex. The kinkiest things I ever fantasized about was getting it on with Rachel and her sister Jamie together. Now I found I enjoyed dominating and disciplining women. Another big surprise was that apparently Rachel enjoyed the pain. During our first two sessions, her pussy was constantly wet. And when we fucked afterwards, not only did she have multiple orgasms but she also came very hard. I was anxiously awaiting our next session! What would that cruel bastard have me do to her luscious body tonight? Well, I wouldn't have long to wait. I hurried home after work and found a package waiting for me. The only thing it contained was a box of old fashioned, metal thumbtacks; I would guess the box contained about 100 tacks. I could only make a wild guess at what devious purpose they were going to serve. I ran inside and immediately logged into my email. His instructions were as follows: The cunt is to wear the white tank top, the leather miniskirt and the 5" black pumps with the strap around the ankle. After your usual warm-up, I want you to blindfold her then place all the tacks close together on her dining room table. Pull up her top and have her bend over the table so her tits are above the tacks. You will then push her down onto the table and cuff her wrists to the legs on the opposite side to the table. Have her spread her legs and cuff them to the other legs of the table. Then you are to whip her ass, pussy and thighs until the are very red. Follow this by whipping her back before releasing her. Next, cuff her hands behind her head and whip her tits paying special attention to her nipples! I called Rachel and told her the required dress code for this evening's fun, then got myself ready and went over. When she answered the door, my heart was in my throat and my cock got hard immediately. Her big, firm tits were literally spilling out of the tight top and her exquisite, long legs look superb encased in black fishnet stockings and beautifully displayed with the pumps. In spite of myself, I was going to really enjoy this evening. "Hello Rachel, you still want to do this?" I asked hoping for an affirmative. "Yes," she replied. "You know what I can do with the money." "OK, go stand in front of the dining room table, legs spread with you hands linked behind your neck," I commanded. I set up the video equipment and started recording. I went over to my slutty, apparently submissive girlfriend and asked her if she was ready. "Yeah, I guess," she replied. "He has come up with a really interesting scenario for tonight," I exclaimed. Before she could answer, I grabbed her hair, pulled her head back and kissed her roughly. My tongue began to fuck her pouty mouth. She was breathing hard when I released her. Without allowing her to catch her breath, I grabbed both of her now hard nipples between my thumb and forefingers and pinched. She moaned loudly and pushed out her hips. I continued to twist and pull and pinch her engorged nipples and her moaning got louder and louder. "OK slut. Turn around and pull up your top." I went over to the implement table and retrieved the blind fold, two sets of leather cuffs, some rope and the box of tacks. I first place the blindfold over her eyes making sure she can't see a thing. Next I place cuffs on her wrist then kneel down and place cuffs on her ankles. As I rise, I can't resist caressing her tight ass and slip my finger down her crack to find her already hot and wet pussy. I linger a few seconds rubbing her clit and listening to her groan as she pushes down trying to impale herself on my finger. What a slut! I tie lengths of rope to the legs of the table. I slide a length of rope through the D ring on one of the ankle cuffs, pull tight and cinch it off. When I repeat the process on the other ankle, her legs are drawn at least three feet apart causing her short skirt to ride up displaying the top of her stocking and just a hint of her lovely ass. "Bend over the table and put out your hands," I commanded. I slide a length of rope from the other side of the table through the D ring on one if the wrist cuffs and slowly pull it tight. I want to watch as she is slowly pull down onto the tacks. As I keep pulling the rope, her tits make contact with the tacks. She screams and tries to pull back. I pull the rope tight, forcing her heavy tits down hard onto the tack covered table. "Aggghhhhhh," she cried. "Please stop. My tits feel like they are on fire." "If you are ready to put a stop to this madness, I will let you up and it is over. Otherwise, my instructions are to whip your ass and pussy." "I can't quit. I want the money…it is rightfully mine," she whined. I tied down her other wrist and pulled extra tight forcing her tits down even harder into the tacks. She had forced me into this and I wanted it to end…I think. On my way over to retrieve the leather flogger, I place my hand between her shoulders and pushed her down even hard. "Owwwww," she screamed. As you can imagine, bent over the way she was, her short skirt was up around her waist giving me a great view of her gaping cunt and puckered anus. I was amused to see her pussy juice leaking down her leg. "Ah, the lady doth protest too much," I said laughingly. I retrieved the whip and placed it in front of her lips. "Kiss the whip slut," I demanded still amused. "Fuck you," she spat. I placed my hand between her shoulders again. Her tongue immediately began caressing the handle of the whip. "Good choice!" I commented. I go behind her and begin to whip her ass. Over and over I landed the whip. She tried very hard not to move because it would move her tits over the tacks. But as I began to target her vulnerable asshole, she couldn't remain still. Then I brought the whip down on her spread pussy and she screamed. "Oh, please stop. My tits are hurting so much," she cried. "These things are sticking me something awful." "You love it slut," I said and whipped her pussy again. "You are so turned-on, your cunt juice is leaking down your leg." I whipped her pussy as few more times. Then on a whim, I ran the handle up her slit and sank it deep into her pussy. I wasn't expecting what happened next although I guess I should have. She came hard! Very hard! After she calmed down, I brought the whip handle to her mouth. "Suck it, slut. Taste your own juices," I commanded. This time she didn't hesitate. She eagerly took the handle into her mouth and sucked for all she was worth. After a few seconds, I pulled it out. Then I raised it and brought it down hard on her back as instructed. She wasn't expecting it and again pushed her sore tits into the tacks. After she came, I really wasn't into whipping her much anymore. I needed relief myself. I knew I wasn't going to last the entire hour. I half-heartedly whipped her back a few times. Then I released her wrists and allowed her to stand up. Several tacks remain imbedded in her tit and they had a bunch of tiny puncture marks. While I undid her ankles, she picked off the remaining tacks. Lastly, I removed the blindfold so she could see her lovely tits. Even with the pinpricks everywhere, they were beautiful. "Alright slut, turn around and put your hands behind you neck again!" I commanded. "Oh, no more, please!" she cried. "Your choice," I replied callously. I went over to the implement table and selected a leather strap to complete her torment. As I approached, I could see in her eyes that she knew what coming next. "Kiss it," I ordered proffering the strip of leather. She looked me in the eye defiantly and kissed the strap. I raised it and brought it down hard on the top of her right tit. I repeated the process on her left breast. After giving the tops, sides and bottoms are good working over, I slap her red, swollen nipples. As when we started, she pushed out her hips. I paddled her nipples until I couldn't stand it anymore. I swiped the tacks off the table. "Turn around and bend over the table again," I ordered. "Oh please, I have had enough!" "Do it NOW," I yelled. She turned around. Spread her legs and bend over the table. My pants were down in a jiffy and my cock was buried to the hilt in her hot pussy. I pulled it out, place it up to her anus and entered her ass. "Oh yes, that feels so good," she managed to moaned just before we both came in explosive waves of lust and pleasure.