Shemale Transvestite

Probably one of the best stories and most popular posts on this site are the ones with a tranny surprise ending. Now shemales aren’t always about just finding straight guys who want to have sex with them, they’re looking for fun and excitement to keep their transvestite lifestyle always at maximum capacity. There’s this fucking sexy shemale by the name of Kelli who by far is one of the hottest trannies out there. She could easily pick up almost any random guy and get him begging on his knee’s for a quick nasty fuck in any alleyway.

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 is one of the best shemale’s at tranny trouble and she’s got this absolute talent of just pulling in handsome men who are just waiting to have sex with her. They of course don’t realize that she is a tranny, but that doesn’t really matter because they still end up fucking. It wasn’t to long ago that Milena had a bet with one of her girlfriend that she would be able to cum all over Reggie who was one of the IT guys down in the basement of the building. Milena being the sexy shemale that she is was all in for this bet and went to work on him right away.

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.

Here we have two hot trannies who haven’t yet met, but they’re planning on doing so very soon. In fact they already have a date and place set. The one transvestite is from New York City and works by day as a Law clerk for a highly reputable law firm. She has secretly keep her real identity on the low key just to avoid any sort of confrontation and surprise, but by night she is one hot tranny making some of the best underground tranny sex available.

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!

I’ve never seen a blonde tranny like Larissa that can take a big cock in her ass that easily. Larissa started making trasnvestite movies about two years ago and just keeps making shemales look more and more beautiful. The producers at Tranny Trouble had been getting a few emails from one really horny young male named Freddy. He was completely obsessed and in love with Larissa and has been watching all of her transvestite movies since before she became a star. Freddy’s emails started with thank you’s and talks about how he masterbates to Larissa every second of the day, but lately his emails have somewhat changed to wanting to meet Larissa.

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.