0 comments/ 241179 views/ 8 favorites From a Lady to a Tramp Ch. 1 By: MasterJack Wendy Monroe sat at the table with her head held in her hands and sobbed gently, she had been sobbing all night. She had been crying for 2 days ever since he found out that her husband had falsified some informational a loan document, the Bank was threatening to have her arrested and tried for fraud. Her attorney told her that she had no recourse, the only thing she could do was come up with the $10,000. She had tried to borrow money against her BMW, but she found out her husband had already borrowed money against the car and there was no equity left. She had checked with a real estate agent to see if she could get some money out the House equity, but he had also took a second mortgage on that too. All of the nearly quarter million dollars her father had left her was gone too, and she was penniless without it even a job. Wendy poured herself another glass of bourbon and began sipping on it, while praying for a miracle that she knew would never come. A friend had told about a man that everybody just called Mr. W, he loaned money to people without collateral, because if they didn't pay he would show them the error of their the ways. Wendy brushed her blond hair out of her eyes. At 38 years old she still had a very good figure with a nice 34 C bust line that no sag even without her bra. She was proud that she only weighed a 128 lbs., and stood 5 ft. 11 in High. What she was sorry about was that she had put so much trust in the man that she though was her husband, only to find out the he was a bastard. Wendy did not know what she was going to do she was afraid to go and see Mr. W, but she was more afraid of spending time in jail for fraud. With trembling fingers Wendy picked up the phone and dialed the number, then she almost hung up when someone answered at the other end of the line. The secretary gave her appointment that afternoon at 2:00 p.m., and then gave her the address down town to come to. Wendy parked her BMW on the street in front of building and then followed the directions to the office, where she was greeted by the secretary seated behind her desk. There was only one other door in the office, and the secretary told Wendy to go on in she was expected. Mr. W turned out to be a man about 6 ft. tall, about 220 lbs., but slightly graying hair in his mid 40's. He waved her to a chair across the desk from him and waited for her to sit. He was the first to speak, " I hear that you need to borrow some money, and you must go to unconventional source because of your lack of collateral. The people I represent also must have some form of collateral; the days of breaking bones for nonpayment are over. We are now just businessmen making living, sometimes we except different forms of collateral and a bank would, but we still need some form collateral. How much money you need? " Wendy wished she had some bourbon now as her throat felt dry, " I'm in a bad way right now, my soon-to-be ex-husband ran off with another woman. He borrowed money against my BMW, House, and hocked all of my good jewelry. The worst thing he did though was he borrowed $10,000 from the Bank, and he falsified the papers then had me to sign them, but I trusted him. Now the bank says I have less of a week to come up with the money in full or they will turn the papers over to the state's attorney. I've talked to my attorney and he told me that if I don't come up with the money I will go to jail. I have exhausted all my other forms of Finance, and you're my last hope. I don't have anything left for collateral except my word that will pay you back. I hope you can find some way to help me. " Mr. W leaned back at his desk, " Well Mrs. Monroe or would you rather me call you Wendy? " " You may call me Wendy, I just hope you can help me. " Mr. W continued, " OK Wendy, you are in deep trouble. Lets go over the fact's, you don't have any material collateral, you have a very short amount of time to come up with the money, or go to jail. You seem like a rather well educated lady, but I would guess that you never worked a job in her life other than charity work at the hospital. So if I did loan you to the money how are you going to be able repay it? My associates charge 10% interest per month on in the unpaid balance that means that the interest each month on $10,000 will be a $1,000 your not going to be able to pay that interest working at McDonald's. I'm sorry that I have to ask these questions of my associate’s demand it. Have you given any thought to repayment of this loan? " Wendy sat stunned for several minutes, he was right she had never worked other than for charity in her life, and now the interest she would have to pay would be sizable. " No, I have not given much thought to how to repay it, my first concern has been how to stay out of jail. I will do whatever I have to pay the alone back to you. " Wendy felt her last chance slipping away, and she began to sob. Mr. W handed Wendy a Kleenex before speaking; " Well your alternatives for coming up with the money to repay a loan are going to be very few. I can only think of one, and I'm not sure your suited to that way of paying off the loan. " " Mr. W I will do whatever I have to do, because anything is better than going to jail. If you know a way of getting and repaying the loan, please tell me what it is? " " The only way I can think of is as an entertainer. " Wendy had a blank look on her face, " what do you mean entertainer, I can't sing and dance I don't understand what you mean? " " I wasn't talking about that kind of entertaining I was referring to something of a more personal nature. I will understand if you're not interested, but that's the only way that I can suggest that will allow you to pay off the loan. The choice is yours to make, but I can't consider loan unless there's a way of being repaid. " Wendy looked down their hands, she understood what he was getting at, and she was not that kind of woman, but she didn't want to go to jail either. What was she to do become prostitute, or go to jail, she didn't like either choice. Mr. W was the first one to speak, " I'm sorry Wendy, but you’re not cut out for this kind of work. I would have really liked to help you, but I don't feel you’re at all comfortable with this, and it really probably would not work out. Please tell my secretary to send in my next appointment on your way out. " He then turned its attention to papers on his desk. Wendy felt a twinge of panic, this was her only hope, and he had given up on her. " Please Mr. W I don't have any other option, please give me a chance I can do it, you tell me what I have to do and I will do it. I don't care what I have to do. " " OK Wendy, here's the deal every time you entertain a person you get a hundred dollars off of your of your account, if you entertain two people at the same time you get a $150 off your account. Because your interest-rate is 10% per month or for $10,000 is $1,000 the first month. That means you have to earn at least a thousand dollars just to pay the interest each month. Every dollar over the thousand dollars goes against the principle until the debt is paid in full. " Mr. W waited for the meaning to sink in. Wendy's head was swimming when she answered, " I've never done any thing like that before, but I don't have a choice, because without the money I go to jail. " " OK Wendy, stand up right where you’re at and take off your clothes. " Wendy stood and slowly and undone her blouse one button at time, and dropped it to the floor. She kicked her shoes off, then unzipped are skirt sliding it downer her legs. Her panties followed her skirt down legs, and she kicked them both away at the same time. She reached behind her to unclasp her bra, and dropped it to the floor also. She stood there in front of him totally nude, except for her garter belt and nylons, waiting for her next instruction. Wendy said, " shouldn't you lock the door in case someone would walk in, Mr. W? " " Now listen to me, when I tell you do something don't worry about anything else. Anyway I count on my secretary coming in, because I just called her. " Just as the finish speaking the door opened and the secretary walked in closing the door behind her. " Yes Mr. W is there anything I can do for you? " she spoke as if Wendy wasn't even there. " Yes Betty step over and stand in front of Wendy. Wendy, get down on your knees, lift Betty's dress, and began licking her pussy. " Betty walked over to Wendy, and stood there before her with her legs slightly spread. Wendy was trembling as she got to her knees, and lifted the dress to the other's waist. Betty was wearing a garter belt, and nylons, but no panties. Wendy had never gone down on a woman before, and she wasn't really sure what to do. She just tried to do what she wanted a man of to when he was kneeling in front of her. She must have been successful, because Betty soon began to moan, and thrust her pussy harder against kneeling woman's face. Betty grabbed Wendy's hair pulling her face even harder against her pussy, and then she began to gush her girl juice into Wendy's mouth. Wendy swallowed as fast as she could but some ran downer chin dripping to the floor. When Wendy finished she looked to Mr. W for what to do next, " not bad now get up here on my desk, and lift your legs for me to fuck you. " Wendy got up to her feet, and walked to the desk. She sat on the edge and leaned back lifting her legs so that she was open and exposed for his use. Mr. W pulled his cock from his pants and pressed the head the opening to her cunt. It had been several months since her husband had left, and Wendy had felt the wonderful sensation of a cock deep in her pussy. Wendy wrapped her legs around Mr. W pulling him into her as he screwed her. Her juices were flowing as he all the way in her, up against her cervix. The heat of her tunnel told Mr. W that he wasn't going to last very long. Almost on cue as he began to cum in her, she began to thrash on the desk in the throes of an orgasm herself. When it was over Mr. W made her get on her knees to clean him off before putting his cock away. When his pants were zipped up and he was back at his desk he looked up and spoke, " you will be ready any time I summon you, tell Betty to give you a pager, when a page comes through find a phone immediately and call a number. Now get your clothes and get out here dress in the outer office, I have more work to do. " Wendy picked up her clothes, and stepped through the door into the outer office. She was embarrassed at being nude in front of the people sitting in the office. She quickly dressed, then asked Betty for a pager as she had been told to do. Betty had sympathy in her eyes as she handed Wendy the pager, " I know he can be rude but that this is his normal way. A word to the wise, I have been there before, bring an extra set of clothes with you at all times. When you get a page answer it immediately he gets really pissed off if he has to wait, and he can send you on some really nasty ones, so don't piss him off. " Wendy hurried to her car, and drove home in silence. She poured herself bourbon, and then drew hot bath, soaking in it to try to wash off the grime of what she had been forced to do. When she got out of the bathtub she heard the gentle beeping coming from her purse. She grabbed the pager out and looked the number on the screen, she wished she had a choice but she knew she had to call the number. To be continued. . . From a Lady to a Tramp Ch. 2 The voice on the other end of the phone was a man that Wendy assumed was Mr. W, he told her to go to the Alexander motel, and meet two men there in room 204 when he gave her the number, he said, " you have one hour to get there, and do whatever they tell you do without question. " Wendy had two Bourbons while she was dressing, and as she was hurrying out she remembered what Betty had said and grabbed another change of clothes. She drove downtown to the motel, and parked car in a garage next to the rundown motel. She looked at her watch it was one hour and five minutes exactly when she knocked on the door of the room. The door was opened by a man in his mid 40's his brown hair was turning gray at the edges, he was about 6 ft. 2 in. about 240 lbs., and reminded her of football player. He said, " hey Joe our entertainment is here. " With the door open wide she was able to see the other man sitting at the table across the room, he was overweight, and about the same age. Both men were wearing dress slacks, and in their T-shirts. The fat man Joe said, " come on in cunt, you can't take care of us from out there. " Wendy was not used to the crude language of the fat man, and quickly stepped in to the motel room past the other man. She put her bag with the clothes in it, and purse on the dresser, then turned to face the men. The one at the door slammed the door shut behind her, " OK sweet cakes get the clothes off and let's get to having some fun. " Wendy began taking her top off, but evidently she wasn't fast enough because the big man grabbed a hold of her top and ripped it off her shoulders. Wendy hurried and dropped her skirt to the floor; her panties and then her bra followed it. She was glad that she at brought extra clothes with her, because it was embarrassing to have to dress in the outer offices in front of the people there. It would have been much worse to have to go home without a top; she made a note to thank Betty for her advice. Wendy did not have to stand there very long in the nude. The fat man said, " come on over here cunt, I want my cock sucked now. " Wendy walked over to him, but before she could make a move he grabbed her hair, and forced her to bend over to where her face was in his lap. He unzipped his pants pulling his cock out; his cock was not as big as her husband's cock. The cock that was soft but soon began to harden in her mouth becoming about 6-in. long and average thickness. She was not used to the vulgar language, and the abuse they were giving her, mainly the fat man. Wendy had forgot about the other man until she felt his hands on her hips, and he forced her feet apart making her spread her legs. Wendy felt the head of his cock as he tried to force it into her dry cunt, the pain was almost unbearable, and Wendy swore that he would get the son of a bitch who had put her here. Finally at last her juices began the ease the passage, and the man was able to begin an even stroke. Even her body began to betray Wendy as she started to meet his strokes coming back, as he was going in, and grinding her pussy against him. The man in front of Wendy had two handfuls of her hair, and was forcing his cock all way down her throat, making her gag, and her throat muscles contract on his cock. At first she panicked fighting for each breath of air, afraid that she was going to strangle on the invading organ, but then she realized that at the last moment he would pull her head up giving her a chance to gulp some air. Wendy concentrated on getting the man off so that her ordeal would be over soon, she reasoned that she could get him off he would let her go, and She could breathe again. She didn't deserve to be treated like this just because she had trusted a man who said he loved her but really only used her. Then suddenly the fat man pulled her head down to him, and began to cum in her throat making her swallow fast to get it all down. The man at the other end rammed all way inside her, and he too began to cum deep in her cunt. When both men were spent they let her drop like rag doll, where she fell to the floor for in a heap. As she lay there on the floor the man that was behind her grabbed her hair pulling her knees, and as he sat on the edge of the bed made her clean his cock with their mouth. . When his cock was clean he made her continue sucking on it; it was bigger than her husband's almost 9 in. long, and thick as her small wrist. She concentrated on using her tongue to swirl around the head, and lick up and down the length of it on the sides. He pushed her face down to his balls and made her lick him there, first on one, and then on the other. The fat man got behind her, and pulled her up to her knees. Wendy felt his stubby little fingers probing at her virgin anal opening. She tried to tell him no the stop, but the cock the filling her mouth made it impossible. All that came out was, muffled grunts, and groans. Wendy hoped that he would not be able to get his cock up again, because she had never let anyone do what he was trying to do. Then she knew the truth as she felt the head of his cock began forcing his way in where his fingers had just been. She felt her skin tearing and she knew that she would be ruined for life, but he kept on without any mercy. The tall man in front of her at least had more mercy, because he saw what the other was doing and began to stimulate her nipples. Wendy was crying around the cock in her mouth, and she felt like someone was shoving a broom handle up her ass. The fat man did not last long, and then she felt him flooding her insides with hot cum. The other man in front of her took his time, while rubbing her breast and pulling on her nipples he brought her to completion also to a shattering orgasm. When at last he came he pulled his cock for mouth, and shot his load all over her face. The man said, " baby you were well worth every penny. You can get dressed now and beat it. " Wendy used her torn blouse to wipe the cum from her face, and quickly put her clothing on hastily throwing the blouse in the sack. She didn't look at anybody as she walked to the car, and then drove home. Once in her bedroom took the clothes off and threw them way trying to rid herself of the memory. She spent an hour in the hottest water She could stand trying to wash the touch of the men from her skin. After the shower she fixed herself bourbon and put on some sort of music to relax with. Wendy felt almost decent when she was brought back to reality by the sound of the pager going off. She hated the thought of dialing the number, but she knew she had no choice. When the phone was answered it was Betty on the other end. " Hi Wendy, Mr. W wanted me call and tell you that you have done good so far, and to tell you to come by 5 today. He wants to have a session with you and me after we close the office, I hope you don't mind, but I'm kind looking forward to it also. " Wendy said, " No I don't mind, I have to thank you anyway for telling me to take that blouse with me, it came in handy. Thanks I'll see you at five. " Wendy took another long hot shower and downed two more Bourbons while getting ready. She parked her car in the same places before and made her way into the office arriving at 5 exactly. The sign on the door said closed, but when she tried the handle of still open. The outer office where Betty set was empty, and she made her way into the inner office. Mr. W was sitting in his chair with his pants off, and Betty was naked on her knees in front of him giving him a blowjob. Mr. W said, " did you lock the other door on the way in? " " No I did not know you wanted me to, but I will right now. " Wendy headed back to lock the door before returning to the office. When she came back in Betty was still taking his cock deep in her throat; his hands were rubbing her breasts as she worked on him. " Go ahead Wendy get your close off and we will be ready. " Wendy hurried and removed her clothes laying them on the chair next Betty's. When she was naked Mr. W motioned for her to come over to the chair were he was, and bend over for him to suck on her breast one then the other. He was an expert at using his lips and tongue to make her nipple get hard, and then he knew just how to nip the nipple with his teeth. Wendy was in seventh heaven as he worked on her, then he slid his finger and rubbed her clit. She thought her knees were gonna buckle as he worked on her, she should hate him, but he had saved her from going to jail, and she knew deep down that she did not have to do anything, if she didn't want to. No one was holding a gun to her head, and there was only one person to blame her husband, and some how she is gonna get him. Just when she thought she didn't take any more Mr. W came deep in Betty's throat. He stopped rubbing her pussy just as she was ready to cum leaving her ready to scream. He said " Betty you and Wendy get on the couch over there and start making love with each other. " Betty led Wendy to the couch and sat down next to her, then ever so slowly their lips. Wendy found that kissing a woman was no different than a man. Was different was with a man he was taking, but with Betty there was a feeling of sharing. Her hands began to explore Betty's breasts, than her hand began to move down to explore the others pussy. Betty was letting her hands explore Wendy at the same time, and Wendy felt her orgasm beginning again, but this time Betty sensed it and took her over the peak. The time was a blur and soon they were in six to nine position with Betty on top. Then when we thought she couldn't get a higher she looked up between Betty's legs and watched as Mr. W slid his cock deep in Betty's ass. When Mr. W was ready cum he pulled out of her ass and slid it into Wendy's mouth filling her mouth with cum. All three collapsed in a heat and for 10 minutes all was just heavy breathing. Half an hour later of three for sitting around the office having a drink, when Mr. W said, " Wendy that was great you've done very good and I'd like to show my gratitude some how. If there's any way I can help you let me know? " " The only now want now Mr. W is to get that son of a of a bitch that did this to me. " Mr. W said, " I could take care that for you, I have real mean collector that is the best. I could have him find year-old man and teach a lesson in manners, and even have him videotape it so you could have it to watch. He usually charges a grand, but I could probably get him to do it for $500 if you’re interested. " " I don't want any thing broken, I just want him to have to be taken in his ass, and then made to suck the cock clean afterward. " Mr. W nodded his head, " OK consider it done, I will add the 500 on to what you owe. " Then with a smile on his face he said, " hell baby consider it a gift from me, you don't owe any thing for this I will take care of it, OK? " That night Wendy finally slept a good night's sleep something she had been done along time. Wendy knew that tomorrow the pager would go off, and she would be expected to perform, but that was another day. To be continued. . . From a Lady to a Tramp Ch. 3 Wendy got up the next morning and went out shopping for some new clothes, she wanted something she could take off quick, but yet was still decent. She found herself looking at thong panties, and stretch type sports bras for support but easy to remove. She just paid for her purchases and had walked out of the store in the mall when the pager went off again. She went to a pay phone in the middle mall and dialed the number waiting for an answer. It was Mr. W on the other end of the line, and he gave her an address to be at in an hour. Just enough time for her to get into her new thong panties, bra and have a couple Bourbons before she went there. Then 55 minutes later she knocked at the door and was greeted the and by a man in his late 30's. He was tall about 6’ 4” and weighed about 240 all which was solid muscle, but it was this smile that she noticed first when he opened the door. He held the door for to enter, and then closed it behind her locking it. He was the first to speak, "my name is Russell, but everyone just calls me Russ, OK sweet cakes take off all your clothes and lay down on the bed. " Wendy stripped her clothes hanging them on a chair until she was completely naked, and then she walked over to the bed laying down on it. She was unprepared for what happened next because the Russ started kissing her neck and shoulders working his way over shoulders and on her breast. He sucked one nipple and then moved over to the other to suck on it he spent a long time working on nipples till both were hard as rocks. His lips left slight trails moisture over her stomach as he worked his way down to her cunt. Then his thumbs opened her pussy lips letting his hot lips find her clit and began sucking on it. He let his teeth nibble on the inside of her thighs all the way from her knees to her pussy. First he had one finger inside her cunt, and then added another to it. With two of his big meaty fingers delving inside of her she had the most violent orgasm of her life, and when she came he covered her pussy with his mouth sucking her juice from her. The next thing that Wendy knew she felt him sliding his cock inside of her gently slowly inch by inch, until he had all 9 in. deep inside of her. Wendy had no idea how many times she came as he slowly screwed her but when she felt him tense she wrapped her arms legs around and pulled herself tight to him. They both collapsed in each other's arms, and when he rolled over to the side of her she rolled over putting her head on his chest. The bed was wet and sticky when they finally got up, and he kissed her gently on the forehead. The Russ walked to the dresser and turned on the TV, pressing the play button on a tape player next to it so that there appeared a picture on the screen. The image was a long hallway the only person visible was the Russ she watched as he went down the hallway stopping in front of a room. He knocked on a door, when someone inside asked who it was he replied room service, there was some grumbling in the room and someone mistakenly opened the door. Before the person could discover that it was not room service the man shoved the door open by force sending the other person behind the door crashing to the floor. The man entered the room followed by whomever was carrying a camera, and the door shut behind them. On the floor was her husband Frank, and trying to cover herself on the bed was his blond secretary. The Russ reached down, and picked Frank up by his hair till he was standing. The Russ said, " get your clothes off and get on the bed motherfucker! " Frank had very little to get off as the lonely wearing a pair of boxers, which he dropped and set on edge of bed. Russ walked up to the bed and jerked the cover from the trembling secretary’s hands leaving her nude on the bed also. Russ reached into the bag he was carrying and pulled out a strap on dildo that was larger than anything Wendy had ever seen. He tossed it to the scared secretary telling her to put it on. Russ then began undressing neatly folding each garment he had on and laying them on the dresser. Frank's eyes darted to the door several times as he weighed his chances of getting away, just as the Russ finished removing last of his things Frank made his move. Russ was quicker though and a large fist hit Frank square in the side the head knocking him almost unconscious. When Frank regained his senses the Russ standing over in waiting for him to try again, the all the fight was gone as he lay there on the floor. Russ said, " were do you want my cock in your mouth or your ass? " Frank knew he had little choice, but he thought if he could make the man cum in mouth he get it over with without too much pain. He rose to his knees in front of man, and took the cock that was twice the size of his in his hands. The man was 9 in. long and 3 in. thick. He really did not know where to start, but it is started licking the head like he liked for women to do him. He opened his mouth wide taking in the head he began the sucked using his tongue all we could think of was getting it over with as soon as possible. Russ grabbed Frank’s head and began forcing more of his cock it into his mouth, to the very entrance of his throat causing him to gag. Frank tried to push the Ruses' hands away but he received a hard slap to the side of his head for his efforts. When the cock would enter his throat Frank felt bile going up his nose and dripping out, but he had no choice and kept on sucking the cock in his mouth. Russ began to force more and more of the cock down his throat and laughed at his discomfort. Russ said, " now you know how your wife feels, this is what you left for her. She wanted you to know how it feels to be used as a piece of meat, so enjoy your lesson. " Frank coughed sputtered and gagged, but the cock continued ramming its way down in his throat. Try as hard as he could the Russ could not force all of his cock down Frank's throat, it just would not open that wide to take the whole thing. The finally Frank felt the cock tense and then the flood of hot cum the filled his mouth and leaked out around corners of his lips. There was so much he had to swallow fast and still some managed to drip down the front of him. When Russ pulled his cock from his lips the string of cum connected his lips of the head of the cock. If Frank thought is his ordeal was over he was wrong, because Russ grabbed his hair again and dragged him over to the bed forcing him to kneel in the center with his ass in the air. Russ gave the Secretary a tube of Vaseline and motioned for her to get behind Frank with the with the strap on dildo. When she had lubed his ass with the Vaseline she proceeded to put the head of the dildo at the entrance to his tiny asshole. Frank was almost out of it from all the he had suffered and didn't even move until the head of the dildo spread his tiny spinster brutally. Even with the Vaseline the going was slow and the secretary was only able to enter an inch or two at a time and then had to pull back to go again. After 10 minutes of constant sawing and out of his tortured ass Frank was reduced to a moaning piece of flesh. When at last the Secretary finally collapsed on the bed next him everyone could see that Frank had cum several times all over the bedspread under him. Russ finally gave Frank a slap on his ass as he and the cameraman left. When the light Finally dimmed and the tape stopped Russ took the tape from the tape player and gave it to Wendy. Russ said, " I hope that's what you wanted? " Wendy smiled and leaned over giving Russ a kiss on his cheek. " Yes, I wanted him to know how it feels, how he left me, just the way you did him. Thank-you. " Russ said, " Mr. W told me what he had done to you, and asked me if I would take care of this for him. I always check out who I am working for before I do it though, and I found out what happened to you I called in some markers. Here's your contract Mr. W and his friends owed me some favors so I picked up your contract for you. " Russ reached on the nightstand and picked up the piece of paper that Wendy had signed handing it to her. She sat there looking at the piece of paper hands knowing that meant she was free, but then she handed back to Russ. Wendy said, " you hold on to it for a while, I trust you. " Russ put the contract back in the drawer, " you know that means that when I call your pager you have to come take care of me as long as I have your contract don't you? " Mary smiled and said, " it could be worse, anyway you aren't that bad. " Seven months later as a process server delivered the divorce papers to Frank at the flophouse he lived in a Seattle, Wendy and Russ were married in a small chapel on the strip in Las Vegas. The blond secretary had left Frank when the money ran out, and now he lived from one bottle bourbon to the next. The end