Sex Stories - Shemale - PAGE 6

Working Late with my boss

Hello, I want to tell a story...my story, about my first love with a shemale who just happened to be my boss. I worked at a bed, bath, and beyond store. I had worked there for about 1 year and a half, and my boss really liked me. I always went and picked up her lunch with mine, never messed up. Her name was Margaret, but I always called her Maggie. In fact, I was the only worker that was allowed to call her that. I thought she was beautiful, she had slender legs. Her breasts and rear were curved perfectly. However, it wasn't just her body I loved. She had the face of an angel. She always had a bright smile, that was accompanied by her passionate blue eyes. She had short brown hair with blonde highlights. We would always talk about our favorite sit-coms and so ... Read More»

Me and Sabrina

This story is fictional. I was just another normal kid. I'm just small and effeminate. My name is Nick. Im 13 years old. I have always enjoyed dressing in woman's clothing. I have a friend her name is Sabrina. Shes a very hot girl. I thinks she 5'5,110 lbs and 36c. Compared to me I'm 5'4 and 100 lbs. Im small. We were at her house one day. Then we walked up to her room and she got in her dresser. Then she asked me something. "Have you ever wore woman's clothing before Nick?" "No that's for fags and Im not a Fag" In which I was lying. I wore woman's clothing almost everyday. " Do you want to?" " No" I almost screamed. The days pasted and she never said a word to me about that again. When she turned 14 ... Read More»

Lucy change part 1

This is a story I wrote a few years ago, and completely forgot about. I'm thinking of continuing it if it gets any reaction. I was a virgin before I met my girlfriend, mostly because of my crippling shyness. She is the reason I overcame both problems, and I have never loved anyone or anything as much as I love her. She is the gentlest person and most loving soul I have ever come across. We have tonnes in common, and she has helped me through some tough times, and been with me through journeys of self discovery. I couldn’t imagine living without her at this stage. Now that that’s out of the way, how about a little background, please stay with me through it. I was almost 18 when I met Lucy (I’m 20 now).I wasn’t, and am not anything to write home about in the ... Read More»

White fuckslut Tgirl & 3 BIG BLACK COCKS Initiation

You lucky, slutty BBC Tgirl fuckslut, I envy you soooooo much. This is the most erotic and best BBC story on this web site. Pleeease keep writing about your BBC fantasies. What a bargain to get gangbanged by about 30 big black studs for only 15 Euros. I loved it when you begged them to fuck you.\r\n\r\n\"Please, sirs. Fuck my ass. Feed my sissy hole with your big black cocks. I need it, I need it so bad. Fuck me like real men. Fuck me as hard as you can. Please!\"\r\n\r\nI loved that you dressed up very slutty in order to tease those big black studs at the bookstore. I also love your author name \"Lockedupslut\". Ah yes, just what I would want to be, a locked up Tgirl slut for BIG BLACK 12\" COCKS to ravage me brutally. I believe that the ... Read More»

Pleasant final

About a month ago I was away at a course. I noticed a guy across the room named Devin who was well dressed and had very feminine features. I sat with him at lunch because I had a feeling that he was a cross dresser or at least gay. Now I've been bi curious for a long time and have had close encounters, but nothing so far as to satisfy my appetite for cock/cum. Over lunch we had a lot of discussions about the course and finally led to a conversation about what we do for fun. Devin told me he was a real clubber and liked to club as much as time would allow. At this point I felt a little bold and asked, what do you wear at the club? Devin had an intrigued look on his have and asked - why do you ask that? I said that I bet he looked really good out at the clubs. ... Read More»

Hermophroditie

Ι am a pure blood. I know many of you have seen Hermophrodites on television, some may actually know one, but I am different. It all started centuries ago in ancient Greece when the gods ruled… My grandmother was a beautiful woman. She was petite with a nice curvaceous body, the desire of all mortal men and priestess of Aphrodite. Truthfully though, she was the horniest woman ever. She would have sex with anyone or anything to please herself. This is where I begin… As my grandmother was out one beautiful day, she wandered into a forest of live trees. These trees were part human and part tree, a cursed thing created by Pan from hunters poaching he cursed them to be the homes of such animals that they killed. As my grandmother walked through the forest, her ... Read More»

Your Son, My Daughter

I met Brad a couple months shy of both his graduation from high school and his 18th birthday, lucky me yeah. We were both jogging at the local park. Brad was a pale, slender, white-boy that always seemed to wear small shorts, well they weren't exactly small, they were regulation racing shorts. I wore some plain old basketball shorts. Brad was usually at the park before me and when I pulled up, was finishing up his stretches and starting his slow jog. I would stretch and take off at a faster gait to follow his supple young ass, and long shapely legs around the walkway of the park. Brad knew that I followed him on his run. I just couldn't help watching the bounce in his ass when he ran. And I hoped I hadn't scared him as I am a pretty big bald black guy. One day I ... Read More»

Summer sun

Evening sunshine is lovely. For a start I can wear less, no coat, no warm clothes, in fact a skimpy skirt and strappy top that covers not much more than the tops of my hold ups and my bra. I like to walk in countryside and feel the warm breeze gently ruffle my clothes and visit those areas where you know others have been when they have been a bot randy. Walking through the woods you can pick up little signs, in one place there are ropes hanging from tree branches and a rug underneath. My imagination races. Its the first time that I have been here and I am the only car parked. All of a sudden a young man emerges into the area, I was a little surprised "where did you come from?" "I am parked up the road and I am on a break". "I saw ... Read More»

Lucy's Change chapter 2

Chapter 2 Sunday was even darker and rainier than Saturday. We woke up still holding each other from the night before. We were spooning. Lucy’s warmth felt so nice against my back. Her legs only reached halfway down my calves, and I could feel her rubbing my legs with her toes. I could tell that she was awake. I could feel her cock pressing against the back of my thigh. We both had morning wood. Luce moved closer to me and I could feel the steel of her nipple piercing against my back. I turned over to face her and look in her eyes to see what was there. Was it the anger or the amusement? The look in her eye told me only that she wasn’t angry. She seemed like her normal self. “Hey” she said in a morning voice. I moved closer to her and put my head on the pillow ... Read More»

On the Prowl

So some good news and some bad. The bad, I'm taking a pause on 'My One True Love' for a little while. The good news, seeing as I finally got some response on it, I will continue the story, though it will probably be on a short leash and will most likely be on a chapter to chapter basis. I had this story in the works for a little while and feel that it is ready for viewing. It's shortish but I think it gets the job done. Hope you all enjoy! Mmmm, Friday nights. Love 'em! It's been a while since I've gotten any action and tonight was going to be a great night! I just knew it! I hadn't had a nice juicy pussy in a week and tonight, that was going to change! I got myself ready before going out tonight. It was just before 10 pm before I left for a night of ... Read More»

A New TS Slut is born

There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat? It had all started a few months ago. I was locked out of my house in the pouring rain, and I went over to our neighbor’s to see if I could hang out with him until my parents got home. He was a cool guy, single, mid 30’s, worked for a software company, and drove a nice car. Had bought me beer behind my parents back once or twice. He’d been over to our house for dinner a few times. My father kind of avoided him but my mother got along with him well. I ... Read More»

The Shemale Wife 1

I am a cross-dresser who has for years enjoyed looking and acting like a woman. Lulu, my wife, started to enjoy this side of me once she discovered how easily she could dominate me. She likes to expose my transvestism to unsuspecting souls. At first it was something simple like holding panties up to my waist while shopping for lingerie. But it has progressed to her telling me to buy specific items like a pink bra, a red garter belt or a black teddy. She also insists that I tell the sails clerk that the items are for me. I will be severely punished if I don’t comply, so when we go into the lingerie department and asked what we’re looking for, I will answer, “A pink bra. I wear a 36A.” It never fails to raise eyebrows. I love the embarrassment of it all. She ... Read More»

A Night on the Town: Part 3

I woke up like I do most mornings, naked, in Gina's arms, her breasts pressed into my back, her semi-erect cock pressed between my ass. I laid there, thinking about the night before, smiling. Soon, I needed to go to the restroom, and gently rose, making sure I didn't wake her. I wandered out of my room, on my way to the bathroom. "Dude, what the hell is all over your ass?" I heard a voice behind me say. I turned, facing my roommate Brian. "Umm, a bottle of lotion must have broken in my bed last night," I replied, a little embarrassed. "I heard Gina and you last night, didn't think you would need any lotion." "Gina puts it on before going to sl**p," I lied, trying to end the conversation. Brian just shrugged his shoulders, ... Read More»

Roadtrip - Part One

My vacations started in five minutes, and I couldn't wait to get out of the office. I had been counting the days impatiently for 2 weeks. Unfortunately, I had made no plans but that was ok, I was going to sl**p late for days! A last minute customer call and I was walking down the hall and out the door, oh boy, I was free! I felt a tinge of fatigue, as my heels clicked on the sidewalk and I felt a nice cool breeze run through my nyloned legs. It was springtime, and soon I would not need thigh- hi's to warm my legs, or boots for that matter. Karl, my co-worker and occasional lover, joined me for the walk to the bus station. He didn't live too far away from me and I felt safer walking from the bus stop through the dark, dangerous streets of our low-income ... Read More»

Larry's New Bitch

Sitting at my desk I was fighting the urge to visit FancySissies.com with every inch of my will. I had been caught last week and brushed it off as a typo misdirect from a news site. Caroline had been the one to catch me, she was an older frumpy woman and wasn't too quick when it came to computers. I figured I had gotten away with it but just the same I had decided to lay low for a while. And I was doing good. Today had just been boring was all, no matter what I tried to do to force myself to stay focused on work I just couldn't. I had typed the address into my internet browser a good dozen times. Each time closing it before the page could fully load. A few minutes before lunch my desk phone flutter with a single ring. I knew right away it was my boss, a single ... Read More»