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.

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.

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.

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.

Kelli was always a really healthy shemale so she was always in the grocery store buying fresh fruits and vegetables since she cooked all her meals always. She always goes to the same grocery store at the same time and usually sees the same people in there. She never really liked to fool around with people she sees on regular basis such as her gym. There are plenty of horny guy’s there just waiting to cum inside her but she just ignores them all. Then it happened, someone new showed up in the grocery store, and it’s a fairly small store as well so he must just be passing by. Kelli kept a close eye on him to see what he was doing but not enough to make him notice that she was looking. Guy’s tend to get all cocky when they see a chick checking them out. This dude however looked like a macho man with his army pants and tattoos. He instantly noticed Kelli and how crazy sexy she was of course not having a single idea that she was a transvestite. Once Jason saw how hot she was, the brain turned of and the penis brain turned on. He didn’t even remember what he was in the store for and all his efforts where now focused on getting in her underwear.

Kelli sensed that she “got” his attention and had this funny feeling in her stomach that this macho man would be a fun fuck and was eager to find out how easy it would be to trick him and how surprised he would be when she starts fucking him in the ass. Kelli went up to Jason and asked him if he was really in the Army and that if he was, how long he was off-duty for. That instantly got Jason turned on and he dropped the apple that he had in his hand. His eyes turned directly towards her, looking her from the bottom up, observing her slim sexy legs which lead up to her short jean skirt. He then made his way up to her tight tank top imaging what her breasts looked like underneath.

Kelli stood there in silence while Jason undressed her mentally until she reminded him that she was still standing there. She asked “Do you like what you see?” and Jason simply nodded his head like a little puppy. She then asked him if he was done shopping and wanted to leave? Of course he just left whatever he was going to buy and followed Kelli like a little dog up to her apartment where she let him suck on her perky nipples. Kelli felt her shemale cock getting a little hard so she went down to give Jason a quick blow job. She took his army pants down and pulled his underwear away to reveal his semi-hard cock with a little bit of cum on the tip. She licked it up like candy. Jason was in heaven as Kelli slowly put his cock in her mouth right till his balls.

Jason started to move his hands towards her inner thigh and removed her underwear while she was sucking him down. She pulled away and showed Jason her shemale dick and asked if he was still interested in some shemale sex. He was completely surprized that Kelli was a tranny but what the heck, he wanted to cum and he wanted to make her cum. He threw her on her stomach and started stroking her cock like he was milking a cow. She loved that he was so rough with his hands like he had never done this before. He was so surprised that she could actually get as hard as him and that her cock was almost as big as his cock. He spit in her ass and said in his mind “this is going to be my first shemale sex experience so I better make it a good one”. He then held his hard cock in his hand and pushed it deep down Kelli’s ass.

Milena first went down to his desk and adjusted her bra so her boobs would be a little more exposed. Reggie who was a pretty handsome man always had hot women approaching him before so he was pretty used to it. He however was not used to the charm that many transvestites possess. She looked him in the eye and asked him a few simple questions about her computer and if he could come help her with her laptop upstairs.

Reggie locked up his computer and followed Milena into the stairwell where she made her move. She started walking up the stairs and Reggie followed trying his hardest not to look up her mini skirt because it was so short. Milena used her shemale charm and walked so hot that each step she took made her ass look so delicious. Reggie’s heart was beating faster and faster and he started to get turned on by this sexy tranny ass.

Milena then stopped on the 3rd floor (which wasn’t her floor) and said she had to make a quick stop to the ladies room which Reggie needed as well to splash some water on his face and cool off. He had just finished drying his hands when he heard the door open and hears the door lock. He looks over and Milena is staring right at him coming closer and closer. She puts her hands out and around Reggie and starts kissing him all over his neck. Reggie instantly puts his hand down the back of the shemale’s skirt and grabs that ass that he was dreaming over. It felt so good and he still had no clue that she was a tranny and that he would be having sex with her soon.

Milena drops his pants and starts sucking on his dick making it harder and feeling it grow in her mouth while she plays with her shemale dick thinking about having wild shemale sex. She’s getting it harder and harder until Reggie gets down on his knees and feels between her legs for her pussy, but instead finds a cock and is so surprised. He doesn’t want to continue but he’s so turned on. Milena says “didn’t you know I was a transvestite?” Reggie replies “I had no idea..you’re so hot and I want you so bad”. Milena just smiles back and let’s Reggie fuck her in her tranny ass until he cums inside her.

The other transvestite, Hilda, works as a dental surgeon by day but also has a family which she spends a good amount of time with after work. Hilda has been living the same life day by day and just really hasn’t had any spice in her life lately. She knew that becoming a shemale would make things a lot different but so far it’s been almost the same except for her transvestite operation. Hilda went online to some shemale personals ads but wasn’t able to find any in her city that really grabbed her attention. She started moving onto other nearby cities and there was one ad that really made her cum. There was this absolute shemale sex listing under the shemale sex listing who was looking for a surprise tranny sex confrontation.

This was the perfect opportunity for Hilda because her office was sending her on a conference to the Big Apple for a few nights. She figured she has nothing to lose, but plenty to gain. She sent a nice sexy private message and attached her favorite shemale movie asking if she was interested in reenacting this movie.

The Law Clerk who was busy working away at the office momentarily after thought she would check her inbox for any new message since she just posted her ad in the shemale personals a few hours ago. Surprised, she saw the message from Hilda and immediately wanted to cum. She made sure no one in the office was around and clicked open. The message was already smelling like shemale cum for some reason and she was dying to know if she was interested in shemale sex. She replied back instantly and included her phone number for Hilda to call.

The instance Hilda got the phone number, she dialed it and they fell in love with each other from that moment on. They talked about what they had in mind to do with each other and they were just dying to taste each other’s cum. The made shemale video’s of each other and emailed back and forth for quite a while up until the date where they were to meet each other.

Hilda was waiting patiently on the side of her hotel room bed for a knock on her door. Staring at the door harder than her cock had ever been, Hilda started to masterbate with her shemale dick. Then knock knock at the door…she was finally here and her moment to finally have shemale sex was here!

They kept it quiet from Larissa from a little while thinking he would go away, but the emails just kept on cumming. It got to the point where he was sending emails with pictures of himself and some famous brazilian shemales including Larissa. The producers couldn’t handle it anymore and had to let the famous shemale transvestite know about her number one fan. She sat down at the computer, and started reading each of the emails from day one. Once the emails with the other transvestites started to show up Larissa got pretty excited and her eyes opened a bit wider.

The producers thought the entire situation was a huge laughing matter, but the tranny had other plans on her mind. She wanted to have tranny sex with this random boy show him what it looks like to have a shemale cum on his face. She turned around and said straight up to the producers, “I want to fuck this horny little pervert in the ass TONIGHT!”. The producers didn’t have a chance to say no, but they knew this was going a great episode so they contacted Freddy by email and arranged for him to come by the studio later that night to meet Larissa the Transvestite.

Larissa got herself all sexy and put on one of her favourite transvestite underwear especially for Freddy since he’ll be taking them off at some point that night. She shaved her small ass hole and made sure it was ready for Freddy’s big dick to fill her up with cum. Freddy was overly excited and had no idea what to do, what to wear or even what to bring. He decided that he would just throw on some jeans and not wear any underware since he figured he wouldn’t be needing any.

It was almost 9pm and Freddy was footsteps away from the studio. Larissa was waiting in Studio Room B and her ass was already filled with lubrication. Her shemale dick was semi-hard and her breasts were getting heavy. Freddy came in and was so nervous but still managed to put his hands around Larissa and kiss her on the cheeks. They went over to the bar and had a small drink and chatted for a short while until Larissa noticed that Freddy couldn’t stop staring at her crotch. She knew what he was thinking and that he wasn’t interested in conversation so Larissa put her Tranny Charm to work and start stroking his arm. Momentarily they were kissing each other and Larissa had her hand down his jeans holding Freddy’s erect penis firmly.

They made their way to the area rug where Larissa tore of her jeans and bra and let Freddy have his way with her. He put her dick in his mouth and felt it grow harder and harder within seconds of him sucking until he couldn’t fit the entire thing in his mouth anymore. Larissa then told him how she wanted to get tranny ass fucked hard so she got up and squatted over Freddy’s now fully erect dick and made sure she was positioned so his dick would enter her tranny ass to start the evening to some hot tranny sex and cum.

Jennifer just had to pick a place, get the tickets and book a place to stay and they were set. Britney thought about the whole idea for a short while and couldn’t decide whether or not the fact that Jennifer was a transvestite would interfere with trying to hook up with random guys or not. She thought about possibly having a threesome but figured most guys would be surprised by Jennifer. Eventually Britney just accepted the fact and appreciated Jennifer for who she is and that she shouldn’t let anything get in the way of them just having because who knows, they might end up having more fun than expected.

Both Jennifer and Britney thought long and hard about where to go and they both agreed that Brazil would be a pretty cool place to visit. Jennifer always wanted to go because she heard there was a huge brazilian shemale group down there and that they have all sorts of hot parties.

Britney was quite amazed at what Jennifer told her about the brazilian shemale population in Brazil and googled enough material to get them on the right path while down there. They actually found out a bunch of cool places to meet other brazilian shemales and even some clubs where they meet just to have quick shemale sex. The trip hadn’t even started and they knew they were going to have one of the best vacations ever!

They got off the plane, checked into their hotel room and both got dressed and headed out to the first tranny bar on their list. Britney was really excited as this was the first time she had ever done anything transexual like this in her life. Jennifer of course was thrilled just to be doing something that involves other hot shemales. She was really hoping for some random surprise tranny sex, but whatever happens during this trip stays on this trip.

The name of the first club was called “Shemale Cocktails” and it was really packed with hot sweaty people of all types. Jennifer was getting so turned on and Britney was mostly in awe by the entire place and that such a place could exist. I guess that’s why Brazilian’s have so much more fun!

Just before he was about to leave the house, Jamal sat down on the edge of his bed and flipped through one of his porn magazines to see if there any last minute tips on how to get laid. As he was flipping through, he found this one article about shemales and how they sometimes hang out at average bars just trying to pick up lonely guys or girls who are looking for some hot spicy tranny sex. Jamal was never really felt that white girls were attracted to him personally, all they wanted was his big dick to fill them out and that’s about it. So the thought of even looking for a black tranny was out of his league but at least worth a try.

Jamal grabbed his wallet and headed out the door to look for the nearest hot spot for the night where he could hopefully get lucky and find someone special. He walked into Zippers which he knew was a gay bar, but had the wildest idea that maybe this was a secret tranny bar, so it was worth a shot. He walked in, grabbed a stool at the bar and ordered a gin and tonic. Jamal took a quick glance across the room and noticed there was only one black girl in the entire place and she was staring right at him. He felt his heart skip a beat and instantly started to picture how the rest of the night would go. He imagined himself sitting at the bar just ordered drink after drink thinking how he wishes he had the balls to get up and go talk to her.

All of a sudden he feels a hand on his shoulder and turns around to be surprised that the black girl was sitting right beside him. She put her hand out and introduced herself as Simone. Her voice was sweet and her hands were so soft. She starred at Jamal as if she had something else on her mind. They chatted for a bit and everything was going great. She was laughing and having an amazing time while Jamal was acting so confident that he knew he was going to get laid this night. Simon then asked Jamal if he wanted to get out of this place and go somewhere a little more private. They ended up going back to Jamal’s place where they both sat down on the couch and Simone took her shirt off to show off her Shemale breasts. Jamal couldn’t believe what was happening right before his eyes and instantly leaned forward to start sucking on them. He put his hand between her leg and felt something a little more than what he thought would be there so curiousity got him to take her pants off and surprisingly Simone had a dick!

Jamal could not believe how he had just thought about hooking up with a black shemale and look at what he has now…a beautiful black tranny! This was Jamal’s lucky night. Shemale Simone asked Jamal if he had ever sucked a shemale dick before or if he had ever fucked a shemale in the ass. Jamal was a complete shemale virgin and the moment he got his dick in her ass, he knew this was his calling.