Shemale Transvestite

It had been a few years since Amanda had converted himself into a man and still had the urge to just suck a man’s cock so hard the cum would burst out but she just couldn’t attract any gay men because of her womanly figure. She thought she had maybe made a mistake with this shemale transformation and eventually started to become less and less interested in having gay sex and more interested in everyday things such as going to work and watching TV in the evening with a frozen dinner. She eventually stopped masturbating and lost any urge to have sexual encounters ever again.

Amanda felt that the life of a tranny either the wrong approach and wasn’t meant for her or she was doing something terribly wrong. She decided to give it one more try before she completely gave up and took on the life of a normal human being. She signed onto the internet and went to the most popular dating website. She searched for a transvestite category but didn’t really see anything that made her little cock tingle. She thought maybe watching some shemale porn might do the trick and get the fire started which worked for a little while. In fact she got so excited from watching all that hot shemale fucking and transvestite sex that she felt she had a chance and this was the place. At the very bottom of the website there was a live chat room where other interested people were able to have cyber sex and virtually fuck each other through the computer screen. Some people exchanged phone numbers and made love over the phone and others actually exchanged email address’s so that they could meet up in person. Amanda felt this was going somewhere and signed on with the name “Lonely Lady”.

Within a few seconds she received a private message from a “Richard”. He started the normal conversation asking where she was from and if she was interested in cybersex. This did not excite Amanda much since all she wanted to do was cum in some guy’s mouth. She then replied back saying she wasn’t at all interested in cyber sex. Richard read the message and wasn’t so sad since he had received those types of responses normally. Amanda then sent another message saying “All I want to do is cum in your mouth”. Richard’s eyes opened wide and his heart began to race…he was thinking he was going to have some random sex tonight. He quickly responded saying “sure baby, I’d love for you to cum in my mouth”. Of course Richard had no idea that Amanda was a tranny and that he was getting himself into a real surprise.

They exchanged cell numbers and agreed on meeting at Amanda’s place since she felt that he was the guy and that he should travel to come see her. Richard arrived at her door and they were both so nervous. Amanda made herself so beautiful and put on one of her most favorite underwear especially for Richard. She bought these underwear at a Shemale convention where the underwear was really sexy looking but also had enough room to disguise her shemale cock. They started kissing and rubbing each other’s body and Amanda felt that this is what she was missing in her life. She wanted to surprise as many young men as she could and just fuck all of them in the ass. She wanted to cum inside them and then lick the cum out of their assholes. She had such a dirty mind when she thought about it and Richard was so surprised that she had a cock but had the most beautiful female body he had ever been with.

Martin had been working for this porn company that wasn’t do so well. The sales were slowly declining and they were promoting less and less material each week. All the galleries were old and even the sexy girls started not showing up. The company decided they needed to switch things up a little bit and they decided that bringing in a new niche such as transvestites and shemales to bring the company back to life.

He had never really met a fully converted tranny but always fantasized about drinking the cum of a shemale. He had no idea where this idea came from since he had never really watched any sort of tranny porn. The executives brought in some transvestites to audition for the videos they planned on filming later that week. There were a few black shemales, asian shemales, but most of them were just really sexy tranny girls. Martin thought to himself that maybe he wanted to wait around after work to see exactly what these trannies are gonna do for the executives because he had a feeling there might be a little tranny surprise somewhere.

He waited by his computer screen and once the clock struck 5, most of the employees got up and left, but Martin stuck around and not to long after they started to arrive at the front entrance. He couldn’t believe his eyes, they were so beautiful and they had such amazing bodies. He couldn’t believe that they were all men at one point. He in fact was getting turned on by these fucking tranny. There was one shemale in particular that really caught his attention and Martin actually caught her attention. Her name was Randa and she felt this very strong attraction to Martin’s manly appearance. He was unshaven and scruffy looking. Randa really liked that about him and couldn’t get him out of her mind. Through out the entire porn audition, she kept thinking about how much fun it would be to show him her shemale cocktail. She had previously been in a few magazine photo shoots where they featured her shemale cocktail. All she had to do was get on her knees and squeeze her legs together so her shemale cock would stick out behind her like a tail. The fans just love seeing her cocktail hang like that…just drives them nuts.

After the audition, Randa came up to Martin and asked him what he does for work and Martin described how he was the one who reviewed the material and made sure that all the scenes had unobstructed views of what was going on and who was fucking who. He said he liked the job in the beginning a lot because he was a big fan of porn, but he later started to become null to everything and even masterbating wasn’t as fun as it used to be.

Randa was so excited to finally meet the one who does all the editing that she asked him out for a drink at the closest bar. It was after all a Friday night and they were still at work. They made it to the closest bar which was pretty quiet for a Friday night and Randa started telling Martin about her previous work and how it’s always been a porn magazine feature all about her shemale cocktail. Martin was so intrigued by it that he just had to see it and they left the bar to go back to the office where they could use some of the empty studios to really get some good pictures of her shemale cocktail.

Valentino always wanted to be in a porn video but never had the acting skills required. He applied constantly at different studio’s and always checked out the hottest adult movie websites to see if there were any positions available. He read up on the internet on how to become an adult movie star but everything he tried always seemed to fail. He thought to himself that he would never get to fuck some sexy girl and get paid for cumming on someone’s face.

He then decided that maybe acting school would be a good idea since there he would be able to work on his acting skills and maybe even meet some sexy young girls who maybe he could convince to make a porn movie for practice and that he best do these things before he settles down and gets married. Everyone thought this idea was crazy but Valentino thought it was a really original idea and since everyone always made fun of it saying it would never work he figured that no one had actually tried it. He had been going to class for a few weeks now and made friends with some really cute sexy girls who didn’t seem that shy at all. They all seemed really out-going and all had amazing tits and most likely wanted to have hot cum all over their bodies.

Valentino started taking notes on certain things that each of the girls said specifically Melanie who really was a tranny. She didn’t really expose the fact that she was a shemale transvestite and did a really good job because Valentino was well under the impression that she had a tight little vagina. Valentino noticed that whenever sex or fuck was mentioned Melanie was always the first one to comment or even respond back. Melanie had this surprise fantasy when she’s browsing through some of her bookmarked shemale galleries that she would meet some random guy that really wanted to fuck her, and she’s show him her dick and he’d be all surprised but so turned on at the same time that his dick would get even bigger and harder and still want to fuck her tranny ass and have transvestite sex.

Valentino finally built up enough courage to approach Melanie one day to hang out after class. She really wanted to hang out but she also really wanted to go home to her computer where she had just downloaded some hot shemale fucking movies that she was thinking about all day long. She just couldn’t wait to get home so she could masturbate and cum all over the computer. Then she thought that maybe Valentino would be interested in watching the shemale fucking movies as well since he seemed like someone open to new things. They decided to get some pizza after school and walk over to Melanie’s place.

On the walk there, Valentino brought up his idea of making some sort of porn video for their next project since it would be cool and different instead of doing what everyone else was doing. He told Melanie that she didn’t have to participate in the acting if she didn’t want to, but would really appreciate if she could help with the filming. Melanie was completely surprise by his idea but gave it a short moment of thought and agreed to it. She said no sex though but only to hide her true identity. They got home, wrote up a quick script of what they were going to produce and Valentino got undressed. He started touching Melanie in her breasts and then started kissing her neck and up towards her lips. She got so turned on by all this kissing that her shemale dick started to grow. Valentino made his hands down towards her underwear and the moment he put his hand down and felt a cock instead of a pussy he stopped kissing her and pulled away. He couldn’t believe what he was feeling and was in complete surprise. He looked at her in shock and Melanie replied back saying “Don’t you want to fuck me?”. Valentino couldn’t accept the fact that he was so turned on by everything that was going on, his dick was harder than ever so he got down on his knees and started sucking that shemale penis like it was candy.

Paul was always a pretty lonely guy and nothing ever worked out for him in his personal life. He tried online dating like lavalife, he tried responding to postings in craigslist but no one seemed really interested in him. He had a great body but the only thing that others were not attracted to was his multiple personalities. One of his good friends was getting married and Paul was tempted to go, but unfortunately had no date. He had to either find a hot date online or go alone in hopes of finding a sex girl who he could try and fuck.

It was the day of the wedding and Paul shaved his balls making sure they were ready for whatever was about to happen. He figured he would either get slapped really hard and go home to watch some tranny porn or he would get lucky and go home with some sexy girl to have some sex. He got to the banquet hall and looked for his table. Of course it was empty and he imagined the most boring night ever, but shortly after there was this crazy sexy girl with the hottest ass. She sat down right next to Paul and introduced herself as Kristina. Her voice was a bit deep and he hands felt a little rough so Paul had a deja vu that he had seen her somewhere before. He then realized that he remembered masterbating to Kristina in a tranny porn video a few nights ago.

Paul was always into the shemale transvestite videos but had never personally met any of them. This was his first encounter with a tranny so he had plenty of questions. This made the rest of the night really interesting for both of them and Kristina was so happy to finally meet someone that wasn’t afraid to be normal around her. Paul’s split personality didn’t seem to bother Kristina either as she really liked when he would randomly say how badly he wanted to fuck her in the ass.

The more that Paul mentioned wanting to fuck her tranny ass, the more horny Kristina became. She couldn’t wait to put Paul’s cock deep inside her mouth and then into her asshole. Paul on the other hand really just wanted to masterbate and cum all over her face. They managed to escape the wedding early to find a secret room somewhere and just have some wild shemale sex. Kristina asked Paul if she could record them so and pretend they were making tranny porn so that Paul could masterbate to it whenever he wanted to. It was one of the best weddings Paul had even been to.