Sex Stories - Shemale - PAGE 19

Slave in Training

There's never anyone that I'm interested in at my school. None of the guys here are hot, and I don't even want to deal with them anyway. That's why I began going out and looking for older guys, ones that know what they're doing. Since I just turned eighteen, that meant that I was fair game for any guy that wanted me. It was an exciting thought, and it often made me feel a bit intimidated, but I'm okay with that. I was done looking for guys at school, so I decided to start looking in other places. Gay bars, no luck. Stores, no luck. The park, you guessed it, no luck. I was about to just give up, until one day I met someone absolutely perfect for my needs. It wasn't a graceful introduction by any means. I was at the mall with some of my friends, going into the ... Read More»

Interlude with a Shemale

John watches her with her legs spread wide and in the air. She closes her eyes as she presses the black rubber dildo against her ass hole. John licks his lips in anticipation as the shiny head of the dildo, slick with lubricant, slowly penetrates her. She moans as her ass hole expands around and engulfs the head. One finger stretches to the end of the dildo to slowly turn on the vibrations. Its soft hum fills the air as her body jumps slightly. Soft ooo's and aaaah's issue from her lips as she positions the base of the dildo against the cushions of the chair. When she is sure it won't slip free, she lets go and relaxes deeper into the chair. More soft sounds of pleasure issue from her as time and the vibrations relax her tender ass. Her eyes open to lock with ... Read More»

Shemale Public Bondage Fantasy

It was a chilly evening, I had arranged to meet him in the city centre. I was wearing a rather skimpy black dress, black lingerie and red high heels. It was my first time dressed in public like this. He was an average looking man, he shook my hand and kissed my cheek, and asked if I was ready. I affirmed, and then he led me to the park in the city. I noticed he had a small bag with him. He opened it and took out several pieces of rope. 'You know what we agreed', he said. 'Yes, I understand,' I nervously replied. I had signed up for an evening of public humiliation at his hands. He led me to a tree which was near enough to the main street. 'Hands over your head', he ordered, and then tied them to a branch above my head, stretching my body out. 'Alright, let's see ... Read More»

Would You Like To Be My Neighbor ?

I first met Robert when his wife and him bought the house across the street and moved their family in. A very nice and quiet couple that seemed to keep to themselves for the most part. One early spring day I was out in the garage working on a project while my wife and son were away visiting some friends across town. I had the garage door open to let the sunshine in to help warm the space as well as my own spirits. During one of my trips out to unload some lumber from the back of my pickup truck I noticed Robert kissing his wife and kids as they were loading into their car. He stood in the driveway and waved goodbye as she backed the car out into the street and drove away. It wasn't long before he was out in his front yard trimming some shrubbery. A while ... Read More»

Me dressed as a Gurl

this happened about 25 years ago when i could half way pass i went to this night club for crossdresser, transexuals and transvestites west of balboa park one thursday night it wasn't has busy has on a friday or week end but there was a nice crowd mustly crossdressers a few trannys it was not to late about 8:30pm the company was fine mainly playing pool and looking around some good conversation us gurls we in back the guys were in front at the bar checking us out i was dressed to kill had on black 4" spiked heels with mesh stocking to my teights with a garter belt and black thong black butt length skirt with a white satin blouse with a black pushup bra with silicon inserts a black wig down to my shoulders and a good make up job done by a friend of mine anyway ... Read More»

How I became a Transexual

I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I went in and opened one up and saw that there was a screen on the back wall and small seat. I went up to the front counter and asked the older gentleman behind the counter how it worked. I paid him and went back and picked out my movie, the cover had a hot looking tranny on the cover with a big didldo up her ass. I've considered myself bicurious, I've used dildos and other toys on myself but have never done anything with another male. I'm a little leary of the whole ... Read More»

Cumming for Christina

I love you and will see you Friday night I told my wife as I hung up the phone. My heart began pumping big time as I hung up from my nightly call and the familiar ring of a new text sounded off. My cock stirred just seeing it was from Christina. The message read that the rendezvous was on for 10:00 with a room number and hotel. I cleaned up nice and fresh grabbed the condoms and lube and headed out. My stomach was in knots as Christina answered the door. I quickly entered and stood frozen staring at her beauty. After months of exchanges on Xhamster we were together. Within seconds our lips met touching soft at first then passionate as our tongues intertwined. I held her tight as we tasted each other. Christina stepped back from my lips “how do I look”? she ... Read More»

Teen pussy rendevous!

Yes, she said she would meet me at the same bathroom stall and would not you know it, she did exactly that! I was already in the ladies room, wahing my hands, and in she walks, absolutely stunning, heels on , short summer dress, beautiful face and hair and what a body, my cock got so hard right then! She went into the furthest stall, good choice baby, and i followed her in immediately. We embraced and kissed and just carressssed out bodies, clothes still on ,yet thet quickly came off and her tits were big and lovely, with large brown nipples, and her pink pussy had but a little pussy hair, i could not wait, so i got to my knees and licked her juicy teen pussy and swollen clit, she had such thick pussy lips, i sucked them like a cock, she began to moan and she ... Read More»

First time dressing and having sex

I had some experiences with men in the past but for the most part I had been living my life as a straight man. I was in a relationship and happy. I was walking through a thrift store one day when I happened upon a form fitting stretch denim jumpsuit. For some reason this garment aroused me. I am not sure if it was the thought of a single zipper enclosing my body or what but I felt extremely horny and the need to buy it. I bought it took it home, tried it on. As I pulled the denim over my body it stretched to fit my shape and as I zipped it closed I could remember feeling extremely aroused as the denim hugged my body. It was a woman's jumpsuit, Jennifer Lopez's JLo brand. For some reason when I had it on I felt the need to be held and fucked, I felt the strange ... Read More»

Popping Lisa's Cherry

The door slammed and Lisa's heart leapt. She was alone, finally alone with all the time in the world to pamper herself. She had hours and hours to look forward to, to be a real lady. It wasn't often that Lisa had such an opportunity, even if she did find herself alone occasionally there was always the certainty that someone would make an appearance before long. Then there was the threat of the unthinkable... being caught. At times Lisa was sure she'd go gaga with the pressure; that she'd end up screaming and running down the street as she foamed at the mouth while screaming obscenities at random passers by ...and all for what? Because she was living a lie, all because she wasn't being true to herself, that's why. Lisa sighed, a heavy, stoop shouldered ... Read More»

The Sneaky Blow Job

Renee and Gina met in person for the very first time at a late afternoon appointment at Phoebe’s Getaway south of Atlanta, Georgia. Both girls had come from far away, and though they were dressed in their boy clothes, underneath the jeans and sneakers there were already twenty painted toes and two sets of pretty lingerie- stockings, panties and frilly girdles. Renee and Gina had been online lovers for a long time, but in real life of course, they would simply be friends sharing each others’ company, getting their makeup, fingernails and hair done, switching into their pretty dresses, spraying a little perfume on their necks and going out on the town for dinner, some drinks and maybe a little dancing. Phoebe was an absolute dear and over the course of a ... Read More»

My encounter with hot sexy crossdresser in Pune

Dear friends Im 6ft tall fair handsome male with big thick cock and mad fan of shemales and crossdressers. I love feminine boys or cross dressers. I was searching for CDs on G4m and while searching I came across this guy who loves to cross dress. his all pics are hot and sexy and he has done a portfolio shoot of his photographs. All in Indian Saree and dress and typical bridal costume, I went mad looking at them and I left message with my contact to him; he called me and we spoke and finalized our date on coming weekend. I went and picked him up from a joint and he was dressed in typical boy clothes then we went to my apartment and he said give me 15 mins to get ready. I was little confused that have I made right decision or not?? but when he cam out after ... Read More»

She-Male Pimp Daddy

I’ve been working the streets for a long time and I know all the ends and outs of the flesh market. I have six she-males that work for me and I get 50% of everything they make plus all the sex I want, any time I want it. I make them work seven days a week rain or shine. I buy their clothes and tell them what to wear and when to wear it. I have a little black book with a lot of clients in it. Some of my special clients are women they love to see the she-males jack their cocks off and eat there cum. One of my clients by the name of Darla loves to hire two of the she-males at once she loves to fuck them with her twelve-inch strap-on cock or have them fuck each other while she watches. One time she had one of them fuck her doggie style while the other one fucked the ... Read More»

Tranny Slave to BBC

I took a drag from my cigarette as I waited on my ride to appear. Looking around it was pitch black outside with only a waning moon and a few stars to light my way in the night. I had been waiting for about ten minutes when headlights finally appeared on the road in front of me, illuminating the sidewalk I was standing on and the stop sign beside me. I could barely contain my excitement. I had been waiting for this moment for a while. I had been fantasizing about it for around five years and I had been trying to get it to happen for about a year. It was a lot of effort, but Lord, I prayed that it would be worth it. I wasn't really concerned though. I knew in my heart that I would have an absolutely amazing night. It was already late at night, and most people ... Read More»

A fantasy of mine with a sexy cd or tranny

i wanna dress you up in a sexy blue fishnet shirt with a red lacy bra under, a short black miniskirt with a pair of red silk panties, some thigh highs and a pair of red high heels and take you out somewhere and fondle you a little here and there then go back to your place and take you to bedroom and lay you on top of me and make out as we feel our cocks grow against another. we then strip off our clothes and go back to what we were doing and feeling precum from our cocks. then i turn you around into a 69 and we start swallowing each other, you making my cock nice and wet for your tight hole. i start fingering your ass then you tell me your cumming and i feel my mouth fill up with your sweet cum. i get you on all fours and rim your ass to get it wet and ready for ... Read More»