Date: Fri, 28 Nov 2008 16:54:13 -0500 From: Joe Limpari <joelimp11@gmail.com> Subject: The making of a Transsexaul Whore Part 1 The Making of a Transsexual Whore Part 1 By Joe Limp This story is fiction. While putting on his makeup to transform himself into Josephine, Joe finally had some time to think about how his life had changed in the past year and a half. He thought back to his senior year of high school. Joking around with his friends and getting laid all the time. Joe wasn't the most athletic guy, he was 5'8" and 145 pounds but it didn't take long for the girls to find out about his 11 inch cock. The word got out after his first gym class freshman year. The boys would shower after class. The very next day Joe had girls coming on to him. The girls where eager to get some of the 11 inches, and Joe would oblige every last one. Then half way thru his senior year his mom was killed in a car accident. Joe never knew his Dad. Suddenly he was all alone. His future looked bleak. Joe wasn't going to college. He hated school work. A matter of fact he hated all work. All Joe wanted to do was fuck. And he had gotten quite good at it. Joe moved in with a friend of his mom's named Susan. She worked as a waitress with Joe's mom. Joe was trying to figure out what to do after high school. He figured he would find some entry level job and see what happens. But until then he decided he was going to have some fun and fuck as many of his classmates as possible. Each day after school he would bring another girl home and bang the shit out of her. On this particular day it was a girl name Beth. Beth was a hot junior that Joe had fucked before. She was the only girl that he had been with that allowed him to fuck her ass. He wanted that ass bad. They came home and went directly to Joe's bedroom. Susan wouldn't be home from work until 5 so they had plenty of time. They immediately began to make out. Joe's hands quickly moved to Beth's tits. She had those nice perky tits. Not that large but she had great nipples. Joe expertly took of her bra and moved his lips to her tits. Those nipples sprang to life. As he sucked on her nipples he moved his hands lower. He reached under her skirt and began to message her clit. She was already wet as can be. He took off her skirt and panties leaving her in her stockings and garter belt. He then pulled away from her and took off his shirt. Beth unbuckled his pants and pulled them off. His boxers were next. She took his limp cock in her mouth slowly began to suck it. She swirled her tongue around the tip and it began to grow. As it became hard she took more and more of it into her mouth. Soon she was bobbing up and down on it. She pushed her head down on it taking as much of it as she could. At the beginning she could only get about half of it in her mouth. She worked it in and out, pushing it deeper into her mouth until she was able to get most of it down her throat. Joe loved it He pulled her head off his cock and said, "I want to fuck you." Beth quickly lied down on the bed and spread her legs. Joe pulled her legs up and put them over his shoulders. He pushed the tip of his cock into her pussy as she moaned. He slowly slid his cock into her. When he got all the way in he stopped, waited a few seconds, and then pulled his cock out of her. He did this two more times. Stretching her pussy for what was to come. Once he felt she was ready he pumped her hard. He fucked her fast and furious. She was moaning and screaming to fuck her harder. This turned on Joe. He continued to fuck her hard until he felt he was going to cum. He pulled out and replaced his cock with his fingers. He finger fucked her until he no longer was on the verge of cumming. He then flipped Beth over and grabbed the KY jelly. He put some lub on her ass as she was begging him to fuck her ass. He lubbed up his cock and then shoved his forefinger up her but. She let out a moan of pleasure. He began stretching her ass. First one finger then another until he had three finger deep in her ass. Beth was begging him to use his dick. So he did. He positioned the tip of his cock on her butt hole. Once again he slowly pushed it in. At first there was pressure pushing against him. As Beth relaxed the muscles of her ass he was able to push in deeper. In no time he was all the way in. Again he waited so Beth could composer herself. She was screaming in pain/pleasure. Her screams slowly changed to moaning. She then began to move her ass pulling slightly away from Joe and back to him. Joe stayed still, letting Beth control the tempo. She started moving slowly eventually picking up the pace. Pretty quickly they were banging away again. Beth begging for faster and harder. Joe was loving it. He was also ready to blow his load. He told her so and pulled out of her ass. She quickly turned around and began sucking his cock. Seconds later he began exploding is sperm in her mouth. She swallowed as quickly as she could. She did a great job but couldn't take it all. Cum was rolling down her cheeks. She looked up at Joe with such a huge smile of satisfaction. He then took his finger and fed her the rest of his cum. Joe then suggested they take a shower to clean themselves up. As they got up to take a shower they were surprised to see Susan standing in the doorway. Susan had come home early from work. When she came in she couldn't help but see what was going on. It was a small apartment and the bedroom was in plain sight from the front door. With all the screaming and moaning the kids never herd her come in. Once Susan saw Joe's cock she was mesmerized. She stood in the doorway watching. She had raised her waitress skirt and was playing with herself. Beth was mortified. She grabbed her cloths and ran to the bathroom. Joe stood there, not knowing what to do. Susan walked over to Joe and whispered into his ear, "You have a beautiful cock." She took it in her hand and started to rub it. Joe decided to go with the flow. Susan was about 40 years old and was beginning to show her age. She was still pretty but as all 40 year olds her body was starting to sag a little. Susan got Joe hard, pushed him to the bed and mounted him. She was still dressed in her uniform. She needed him inside her. She fucked Joe like he was never fucked before. He felt things that he never felt before. He was amazed at how great a fuck Susan was. He held out as long as possible but he soon blew a load deep inside of Susan. They both collapsed on the bed. They laid there in each others arms. Beth had left without saying anything. From that day forward Joe gave up fucking high school girls and moved on to the middle aged women. He realized that women in their 30's and 40's knew how to fuck. Most of the girls in high school didn't. Joe fucked Susan regularly. She taught him the pleasures and techniques of oral sex. She even shared him with her girlfriends. Threesomes, foursomes, the more the merry for Joe. The women didn't have quite the hard bodies that the younger girls did but they had two things high school girls didn't have. Knowledge and money. These women knew how to have great sex and they took pretty good care of Joe. Joe knew what he was going to do after high school. He was going to move to where there were wealthy women. He was going to fuck them for a living. So after high school Joe moved to New York City. He got a room in a boarding house and started to look for middle aged women with money. Joe started to talk to the other guys living at the boarding house and found out that one of them was a bartender. His name was Kevin. Kevin told Joe that if he was looking to get laid to come by later that night. Joe told Kevin that he was only 18. Kevin said that it didn't matter. The owner was not going to be there tonight and he would take care of things. He also made a remark the got Joes attention. Kevin had said, "I hope you like older ladies because the cougars will be out tonight." Joe didn't know what Kevin had meant by cougars but was pretty happy to hear about the older ladies. That night around 10, Joe headed over the bar Kevin was working at. He walked up the bar and ordered a beer from Kevin. Kevin opened a Bud and put in front of Joe and asked him if he wanted to run a tab. At that point a woman a couple stools away told Kevin to put it on her tab. Joe took his beer and went to thank the women. He went and introduced himself and thanked her for the beer. She introduced herself has Stacy. Joe and Stacy talked for a while and had are few more drinks. Stacy insisted on paying for all the drinks. After some flirting Stacy suggested they find a more comfortable setting and invited Joe back to her place. He readily agreed. They left the bar and a limo pulled up. The driver got out and opened the door. Stacy got in so Joe followed her. Joe was thinking to himself, WOW!! The first night in town and I find exactly what I'm looking for. As they drove back to Stacy's place she said, "I hope you don't mind, but my husband likes to watch." The look of confusion was clear on Joe's face. So Stacy continued, "My husband is a wealthy businessman. He likes to watch me fuck young men. Don't worry; you will not have to do anything you don't want to. Just come up and see what happens. It will be well worth it." Well, Joe didn't have much money and the well worth it comment sounded promising so he went ahead and joined them. The limo pulled up to a huge skyscraper and the doorman opened the door. Stacy got out and Joe followed. Into the elevator and up to the penthouse. The elevator opened right into the apartment. Joe was following Stacy when she suddenly turned around and started kissing him. Things moved quickly. Before he knew it they were both naked and he was between her legs giving her the best oral she had ever had. After her second orgasm she pulled him on top of her and they began to fuck. Joe fucked her in every position imaginable. She came multiple times. Finally he told her he had to cum. She told him blow his load all over her face. Joe stopped fucking her, moved into position and blew a huge load in her face. Stacy sucked his cock dry. At this point Joe noticed a man about 50 years old in a business suit sitting in a chair watching. The man said, "Very well done young man. You are very skilled for such a young man." Joe froze. Didn't know what to do or say. The man continued, "Stacy, are you satisfied?" Stacy shook her head in the affirmative. "Great", he said "Now I have a proposition for you young man. Being you satisfied my wife and allowed me to watch I will give you $500.00. If you come over hear and jerk me off, I will give you $5000.00" Joe asked, "Just jerk you off? No blow job or anything?" The man replied, "No blow job or anything, just a hand job." Joe got up, walked over to the man, pulled down his pants and jerked him off. It took about 5 minutes but the man finally blew his load. The man got up and said, "Well done again young man." He pulled up his pants, took out $5000 cash and handed it to Joe. Joe thanked him. The man then left the room. Stacy and Joe dressed and Stacy walked Joe to the door. She knew from their conversation that Joe was new to the city. She thanked Joe for the incredible fuck and told him that she knew the perfect girl for him. She insisted on setting them up the very next day. Joe agreed. Stacy said she would send a car for him. Joe, not wanting Stacy to know where he lived asked her to send it to the bar where they met and she agreed. Stacy's driver took Joe back to the bar. Joe couldn't believe his luck. On his first day in the big city he hooked up with a women, had great sex, made 5 grand (although he wasn't excited about having to jerk a guy off for it) and has a date setup the next night. The next day Joe purchased a suit for his date. He got cleaned up and dressed and headed to the bar. As he walked up to the bar Stacy's car also pulled up. The driver got out and opened the door. Stacy called out to Joe, "Come on Joe, get in the car. I can't wait for you to meet Alexa!" Joe got in the car and Stacy started talking, "Alexa is such a wonderful women. She is 41 years old and runs a very successful business. She works very hard and doesn't have time to meet many men. She is cute 5'10" about 155 pounds and very sweet." Joe herd very sweet and began to worry. Every guy knows that when a woman describes her girlfriend as sweet that means ugly. But what the hell..She has money. They reached the restaurant and were seated immediately. Joe was impressed. Such a fancy place and everyone there knew Stacy. We sat down and ordered drinks while we waited for Alexa. Stacy blurted out, "Here she is!" as she jumped up and greeted Alexa. "Alexa this is Joe, Joe Alex" Joe got up and extended his had while he eyeballed Alexa. Alexa said "Nice to meet you." We went to sit down when Stacy excused herself. She made some bad excuse of why she had to leave and then left. Joe was somewhat pleasantly surprised. Alexa was far from ugly. She was not a beautiful women but cute enough. The two sat and had dinner. They had a great conversation and they both seemed to really like each other. After dinner, which Alexa paid for, they went for drinks. They had a great time together. They really hit it off. It was 4 am before they knew it. Alexa invited Joe up to her place for another drink. They both knew it wasn't for a drink. Joe eagerly accepted. When they got up to her apartment Joe took her in his arms and kissed her deeply. He knew this was the most important sex of his life. If he could get this woman to fall for him he would be all set. Joe made passionate love to Alexa. He took his time and made sure to pleasure her. He pleased her in many different ways. When they were done he held her in his arms as she fell asleep. The next morning they woke and had a nice breakfast together. The conversation was again excellent. Alexa had to leave and go to work but she asked Joe to stay. When she got home they made love again and again. She was hooked. After just 2 weeks Alexa asked Joe to marry her! Joe was shocked and taken aback by the proposal. After all is it not the man's job to propose? But this was exactly what he wanted. He could live the good life and not have to work. The sex with Alexa was not the best, but he could always get a little on the side. He decided to accept the proposal. Alexa was a lot like Joe. She had no family. So they decided that a small wedding, just a couple of witnesses would do. Alexa had a friend that was a reverend and he would marry them. Stacy and her husband would be the witnesses. The wedding took place that Friday. Joe moved in with Alexa and began to live the good life. They had a live in maid Camille. Joe spent most days at home. He and Camille got along great. He was very attracted to her. After a couple of weeks of boring sex with Alexa he decided to flirt a little with Camille and see where things led. Camille very quickly let Joe know that she was up for some fun. Joe began by kissing Camille on her neck. They made out for a while as Joe fondled her breasts. Before long they were in her room, naked and going at it. Joe went right for her pussy. Licking and slurping. He ate her until she was screaming with pleasure. He then slid his tongue from her pussy to her ass. At first he licked the rim. Slowly he pushed his tongue in deeper. They both loved it. Joe ate her ass until she was begging to be fucked. He slid his huge cock into her doggy style. She yelled, "Not my pussy!!! I want it in my ass!!!!" Joe was psyched! He pulled out and looked around for some lub. He didn't see any. He asked Camille if she had any. She replied, "I don't need any fucking lub! I need that huge cock up my ass!!!!" Joe was like, OK and began to push the tip into her bunghole. As he pushed his cock in he couldn't believe that Camille could take his 11 inches so easily. He slid it in and began fucking her ass. She was controlling her ass muscles so well it felt like she was milking his cock with them. It was incredible. Now Joe was very experienced and could normally hold out for a long time. But not in this ass!!! Joe pumped her ass a couple of times and then had the most incredible orgasm of his life. Joe fell on top of Camille and said, "Where did you learn to use your ass like that?" She said, "You will see." Joe didn't understand but he didn't care either. That was the best sex he had ever had. As the weeks went on Joe began going out during the day and picking up women to fuck. He was bored with Alexa. Camille was great and they had sex often, but Joe didn't want to risk Alexa walking in on them. The women were never the same but the hotel was. He got into a nice routine. Pick up a woman, take her to the hotel and fuck. Some days the sex was great other days not so great. Then Joe would go home and do his husbandly duties and fuck Alexa. That was until a package came in the mail for Joe one day. Camille brought it in to Joe first thing in the morning. It was a little strange as Joe never got anything in the mail. Joe waited for Camille to leave and then opened the package. He was shocked at what he saw. In the package were pictures of Joe having sex with the women in the hotel. There also was a note. It read: Come to the hotel. Same room at 10:00 AM sharp. If you don't show I will send these to your wife. Joe started to think. What does this guy want? How am I going to take care of this? He figured he would go to the hotel and try and settle this. Exactly at 10:00 AM Joe knocked on the door. A mans voice said to enter. Joe did. He walked in and the man was sitting at the table. The table had copies of the pictures on it. Joe said to the man, "What do you want?" The man responded, "Shut the fuck up. I'm running this meeting. Sit down and listen." Joe sat down. The man continued, "Alexa hired me to see if you were cheating on her. Obviously you are. I took these pictures. I'm going to give you a choice. Do what I tell you and I will not send Alexa the pictures. Don't and I will and you will be out the door." Joe was between a rock and a hard place. If he didn't give this man what he wanted Joe would be sent packing back to the boarding house. Joe didn't want that so he told the man he would do anything. Just don't tell Alexa. The man told Joe to go into the bathroom. There is an outfit there. Take the cloths that you have on now off and put the outfit on and then come back out here. Joe went to the bathroom to find a pair of stocking, garter belt and bra. Joe thought about it for a minute and decided that he didn't want to lose what he had so he undressed and began to put on the pantyhose. He was a master of getting these things off but struggled to put them on. Once the pantyhose, garter belt and bra were on he turned to go back out. That's when he noticed the high heels. He put them on and stumbled back to the table. When Joe was in the bathroom the man had setup a movie camera on a tripod. He was taping everything. He also had a still camera that he was taking pictures with. He ordered Joe to pose seductively. Joe did. The man then ordered Joe to come stand in front of him. Joe did. He ordered Joe to get on his knees. Joe did. He pulled down his pants and ordered Joe to suck his cock. Joe took the man's limp cock into his mouth and sucked on it. As it got hard Joe continued to suck it. Joe looked out of the side of his eye and could see on the TV what the video camera was recording. He could see himself sucking this mans cock. He was disgusted. At the same time he felt his own cock standing straight up. How could this be? Joe thought. I'm sucking cock and getting hard? At that moment the man pulled out of Joe's mouth and ordered him to get on the bed. Joe did. He took the panties off of Joe. He plopped a wad of lub on his dick, pulled Joe's legs over his shoulders and started to fuck Joe's ass. Joe screamed in pain. The man had an average size penis but it hurt like hell. The man didn't care about Joe screaming. He continued to fuck Joe's ass. After a while the man pulled out and told Joe to get on all fours. Joe did. The man then entered Joe doggie style. Joe was at a 90 degree angle from the movie camera at this point so he had a good view of the man fucking him. Once again Joe saw his cock was rock hard. The pain in his ass had now subsided. It actually was starting to feel good. As the man fucked Joe he found himself liking it. He began to move in unison. A sense of orgasm was coming over Joe. Before he knew it his cock started to spasm. Loads of his cum were squirting on the bed below him. Nothing had even touched his dick, yet he was coming. It was the most intense orgasm of his life. The man then pulled out of Joe's ass and ordered him to turn around. Joe did. The man started to fuck Joe's face. Joe opened wide and took as much of the cock as he could. The man soon blew his load down Joe's throat. Joe swallowed it all without being ordered to do so. The man then took pictures of Joe's stretched ass and cum covered face. He told Joe come back tomorrow at the same time or the pictures go to your wife. He then left. Joe was spent, excited, disgusted, horny and confused. What happened? What should he do? He just was forced to have gay sex and he enjoyed it. If he comes back tomorrow the guy is probably going to fuck him again. But when will it end. Joe decided that he would go back the next day and see where it went. Joe cleaned himself up and went home. He and Alexa had dinner, spent a nice evening together and had sex. The whole time Joe was fucking Alexa he was thinking about what happened earlier and wishing that it was he who was getting fucked. The next morning Joe woke up and had breakfast with Alexa. During breakfast Alexa told Joe that she met a man yesterday that had long hair and she thought it looked nice. She asked Joe if he would consider growing his hair as it really turned her on. Joe told Alexa that he would think about it. Alexa left for work and Joe left for the hotel. He entered the room and the man was sitting at the table again. The man ordered Joe to come and sit down. Joe did. The man said, "My name is Mike. As you know your wife hired me to see if you were fooling around. I'm going to make some money here. Your wife pays me to follow you but how are you going to pay me? I'll tell you. I'm going to pimp you out. You are my little whore now. You are going to show up here everyday at 9:30. There will be an outfit in the bathroom everyday. You will put it on along with the makeup that will be there. Once made up you will be known as Josephine. At 10:30 you will hear a knock at the door. You open the door and let the man in. Don't say anything. Drop to your knees, take his cock out and suck him off. When he is done he will leave and soon after you will hear another knock. You will do the same. This will continue the whole day. Do you understand?" Joe said that he understood. "Good. Now go get dressed." Mike said. Joe did.