Sort by
Relevancy

Free Stories

100%
THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
shemale lover 2012-01-28 3,997 licking sucking fucking Sex Toys
100%
Faux
"What is it?" The woman unfolded the clump of material to expose a black lace bra and said, "I found it in his car, stuffed in a pocket behind the passenger seat." A tear rolled down her cheek, leaving a shadowy trail of mascara. Handing a tissue across his cluttered desk t... Read full Story
shemale lover 2012-02-08 3,379 Fetish crossdressing bra
100%
Danielle Works a Saturday
It had been a few months since his wife left him. Well "ex-wife" as the divorce had been recently finalized. It was her choice; she walked out on *him*. She said she got tired of "Danielle", even though she was entirely responsible for Danielle's "birth" to begin with. ... Read full Story
shemale lover 2012-06-18 5,572 anal sex Creampie oral sex cum swallowing
100%
A Walk
I really was not doing much. Being unemployed I had way to much time on my hands. Sure, I used some of that time to get dressed up and walk around the area. But there was something missing. Looking in the mirror as I was putting on the finishing touches to tonight's outfit, I admired my long thin... Read full Story
shemale lover 2012-07-23 3,011 anal sex sucking cum black cock
100%
An Unexpected Surprise Part 1
Mark's search for 'local color' ended when he entered the neighborhood bar called simply Sam's. It was going on 7 pm as he sat at one of the small tables near the back of the establishment. He was hoping to see some women in pantyhose in a place like this. The hotel bar he had come from was filled w... Read full Story
shemale lover 2012-11-22 4,367 tranny Creampie oral sex
33%
Sleazy Walking
I was bored one night, and began to email wanted ads on craigslist to see who was hosting in my area. I lived in spokane, wa at the time in the east central area, sorta behind the fred meyer. This night was boring, my friends had left a while ago with their girl friends, jealousy began to set in. I ... Read full Story
Ville Lohner 2014-05-15 2,849 Stockings Crossdresser Amateur suck Lingerie
68%
Mary Ann and the Tim the Ranch Hand
A few months after my girlfriend moved away suddenly to her grandparents home across the country,( I learned a few years ago she got pregnant) I was riding around on my bike in the street when my neighbor Mary Ann called me over. She was 18, I was still 12 at the time and very horny since my girlfri... Read full Story
Julliana 2017-01-13 7,311 anal pussy Blowjob cum oral sex kiss sissy Love young faggot
100%
Liberty in Lisbon Part 2
So here I was walking down the Av da Liberdade feeling very pleased with myself. I had just thoroughly enjoyed an experience I thought would only ever be in my dreams and, the best part, there was more to come [cum]. In fact I found myself humming the 59th Street Bridge Song. Life I love you feeling... Read full Story
Rusty12 2019-07-31 4,861 Amateur Masturbation Bareback Creampie Shemale Fucks Guy cumming
36%
The Surprise Visit
I had been chatting for some time online with a guy who said he liked crossdressers and loved getting his cock sucked. we chatted numerous nights, roleplayed online. i guess, i don't remember, but i guess i gave him my address. but i worked long changing hours. one thursdau night about 2 am i was co... Read full Story
bigtranslover 2013-12-17 4,668 first time shemales hardcore
92%
A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
shemale lover 2014-05-21 18,479 shemale fingering cumming
93%
The Hot Girl at the Bar
My girlfriend and I broke up the week before, so I was pretty depressed. The guys at work decided to take me out to the bar after work to get wasted cause that’s what we do. So we all packed into the truck and headed to the bar. When we got there we were the first ones in that night so we sa... Read full Story
shemale lover 2015-10-01 10,293 anal suck Creampie
100%
Adventures of Shemale Sandra Part 1
His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He a... Read full Story
shemale lover 2011-09-02 3,701 anal sex asshole cum
100%
When She became He
A Good Friends Advice "You need a good massage" You know how it is, when everything is going so well, the only way to go................, is down. Let me explain. It started when I just knew I had to dump my boyfriend, even that was a loose term. The first part was true, in two w... Read full Story
shemale lover 2011-09-12 3,396 shemales sex humor Mature
100%
How I Became a Tranny Whore
When I was 30 with children at home I would get dressed in the bedroom. When it was time to leave the wife would take the children off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the children would be a sleep. The plan worked fo... Read full Story
shemale lover 2011-11-07 4,561 anal Cumshot cum swallowing
100%
Marilyn: Going Your Way
"Oh yes…eat me…ooh yeah…" Marilyn was laying on one side, watching her sister Sharilynn get gently eaten by Kat. Marilyn herself was bottomless, letting her limp dick hang down to recover from soreness. Yes, it was one of those weekend afternoons that stretched into... Read full Story
shemale lover 2011-11-08 3,445 sucking orgasm nipples
100%
Becoming Amy
I had been dressing up in women’s clothes since I was a kid. Started with my sister’s clothes, I loved her school uniform. I used to prance around in it when I was lucky enough to have the house to myself, which wasn’t often. I loved pretending I was a school girl, and a rather nau... Read full Story
shemale lover 2011-12-06 6,821 anal shemales bdsm
100%
Dirty TS Supprise
True Story I'd been out drinking with a few mates first the pub then we hit the clubs. It was late and I had work then next day so left my mates and went to get a taxi home. walking up the street for a taxi I noticed a woman standing on the corner. The girl was facing away from me but looked hot fro... Read full Story
shemale lover 2011-12-07 3,087 anal shemales hardcore
100%
Headmistress' Favorite Sport Part 6
At Mistress Rachel and Master Tony's house Denise was pushed into the role of maid along side her mother, Susanna. Susanna had been reshaped exactly as Mistress Rachel wanted it. She was now a devoted little nymphomaniac slave who loved her mistress and master and who would do anything for them. Lik... Read full Story
shemale lover 2011-12-13 4,571 torture toys bondage and discipline chastity belt
100%
The Greatest Lie Part 12
My Own Worst Enemy Let’s face facts. The so-called the "War On Drugs," "Just Say No," and all the other anti-drug campaigns are complete failures because they ignore reality: getting high is fun. College students drink and take drugs to break a boring routine; the poo... Read full Story
shemale lover 2012-01-20 4,231 hardcore crossdressing fantastic bondage and discipline
62%
Floor Crossdressing Whore
Hey i'm 6'0" 160 and it was my first year in college and I turned 19 over the summer.I am living in an all guy dorm, and I was very nervous to be in a new place, but i knew how i could relax. I set up my computer and went to my favorite website. The site had crossdressing men who got fucked by ... Read full Story
shemale lover 2012-04-08 2,896 Crossdresser Creampie blonde cum swallowing
100%
Late Night BJ
A few nights ago I was feeling horny and desperate for something to wrap my lips around. Flicking through the pages of various sex sites I found out there was a dogging spot close to where I lived, feeling a little nervous I decided to give it a go and see if my luck was in. I went to my 'slut' ward... Read full Story
shemale lover 2012-05-18 2,292 Cumshot oral sex tgirl
100%
Darla's Video Delight
The day had gone well so far with my girlfriend of the time having just left the night before, going out of state for two weeks visiting relatives. It was Saturday so I didn’t have to work, I had completed my chores... shopping, cleaning the apartment and doing laundry and had spent the aftern... Read full Story
shemale lover 2012-07-14 3,114 Fetish cum oral Latex
100%
Whoring night
Last Saturday night I was in a very risqué mood. I was feeling hot and slutty and just wanted to show it to others. So, I went through my wardrobe, looking for some clothing to show my mood. Some may even say "whorish" and I´d totally agree. Well, that was the idea - that&acut... Read full Story
shemale lover 2012-07-20 3,072 Cumshot facial oral sex deepthroating
100%
A Weekend Together Chapter 2
The next day we were awoken by the phone ringing, it was Ben asking us to meet him at a restaurant on the beach at 5. I told him we would be there and couldn't wait to see him again. We got up and stripped down to get in the shower, we took off my boobs and she unlocked my cage saying if I touched i... Read full Story
shemale lover 2012-07-24 2,009 sucking Fetish cum stroking crossdressing rimjob
0%
A Working Sissy Girl
I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon ... Read full Story
shemale lover 2012-07-29 3,701 Cumshot oral sex sissy
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,200 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Building Pandora
It was over that quickly. In the course of one woman's lifetime, she had destroyed the entire human race. It started in 2008. A researcher named Dr. Panela Dora discovered a symbiotic life form living in the bloodstream of almost every species of shark. It was discovered that this life form, dubb... Read full Story
shemale lover 2012-09-29 2,890 first time Cumshot fondling stroking
100%
Working for Halloween
I stepped off the bus and walked the short distance to the 'Costumes and More!' shop. I couldn't believe I had agreed to do this, but if I was ever going to buy a car, I needed to get the money. You've probably seen them, this particular costume shop always has someone in costume out in front holdin... Read full Story
shemale lover 2012-10-02 4,623 Cumshot oral sex cum swallowing cd
100%
First Time Out
I'm so excited and want to relate this 100% true story quickly while it's still fresh. Please forgive any typos. [My background: Age 48. Closet dressing in earnest for 15 years. Began with slips stockings and nighties but have collected extensive full wardrobe and accessories over time. Boobs, wi... Read full Story
shemale lover 2012-10-23 3,275 sucking cum Sex Toys
100%
Angel Chapter 1
On her eighteenth birthday, fresh from her shower, Angel Jones looked at her nude reflection in the full-length mirror in her bedroom, and was mostly pleased with what she saw. Her blonde hair, down past her shoulders and still growing, was soft and shiny, and all that she could have asked for. She ... Read full Story
shemale lover 2012-11-30 6,011 wanking feminization climax
94%
Daddy and his wicked ways
My name is Miss ________________ (You fill in the blanks). I am a TV/TS/CD who likes to be used in a sexual context by manly men. This tale is about me and my desire to be used over and over again. In a way I'm a little reluctant to share my fantasies with the great British public because they&... Read full Story
Daddy knows best ! 2015-11-24 6,344 suck submissive ts cd tv
100%
Liberty in Lisbon Part 3
After Olivia had so perfectly taken my anal virginity, we laid in bed cuddling, touching, kissing and her cum leaking from me. I had not been so lovingly caressed for such a long time. It was just perfect. She asked me how I was feeling. I think I said before that I don’t do deep and meaningful very... Read full Story
Rusty12 2020-09-16 3,281 Masturbation Shemale Fucks Guy Blowjob old-and-young 69 sucking
100%
TG girlfriend is my new neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-01-17 4,067 Big Tits Bareback Creampie Shemale Fucks Guy Big Cock Asian Guy Fucks Shemale
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,452 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
93%
Homework
Daniel was a 15 year old teenager, like any boy his age, he was full of hormones and sexual fantasies for every pretty girl that passed in front of him. In the last weeks of the school year, the history teacher had a child and was absent from school, being replaced by teacher Marlene, a trans woman.... Read full Story
haroldãosanguebom 2024-01-09 6,908 Shemale Fucks Guy Big Cock Mature
80%
Trance club
It was the worst day in my life. My girlfriend Ally and I had been quarreling and rowing for several weeks, we were on the verge of breaking up. I just wanted her to be happy. I lived my life for her. I guess I stood no chance to make her smile at me again. We broke up. Ally said everything was chan... Read full Story
shemale lover 2014-05-25 7,797 sucking shemale
100%
More TS sex
Some time passed since my first encounter with the lovely transvestite and I often remembered it in my lonely bed. But I couldn’t make the decision to seek her again. Maybe afraid from being seen, as she used to walk around near my office I started leaving office before dark. When I went ou... Read full Story
shemale lover 2014-08-19 5,470 shemales gay male oral sex
96%
Suck like no other
This is a guest post from our reader, Richard In Houston. He met a beautiful young lady, Terry, who taught him to "suck like no other". An awesome shemale story to read, if You ask me! I was separated from my first wife the first time it ever happened to me. We had only been separated f... Read full Story
shemale lover 2015-02-03 7,027 suck Blowjob shemale
50%
His sexy flies catches my eye
Another routine day was passing as I carried my shopping bags back home. Turning up a side street the late afternoon sun shining I suddenly encountered the most sexy guy I had ever seen. He was so cool that I hadn't even seen guys on TV as cool and good looking as that. He was an Asian guy in his... Read full Story
shemale lover 2011-09-16 2,892 anal shemales interracial sex
100%
My First Time Out Part 3
Angelo was still working on Shayna's blonde wig. He fussed with it, combed it, and teased it. Angelo knew a romantic style was very important to Sir Dominique. Shayna was escorted to a tremendous makeup table. Saki placed a headband on her that stretched her scalp and raised her non-existent eyeb... Read full Story
shemale lover 2011-10-18 4,212 blonde shemale massage
50%
Sealed With A Lick
The frail, skinny boy who sat sleepy-eyed on the bed before me gingerly pulled the hem of his bright orange top an inch or so lower to cover the lean, white meat of his belly. His long, shaven legs dangled in opposite directions off the foot of the bed. He wore striped knee socks, navy blue and red,... Read full Story
RazedGlory68 2012-02-24 2,925 Fetish crossdressing gay
100%
A Dare Gone Right
'Well, Paul, if you're not man enough, just say so!' 'Come on, that's not fair, Isabel. I've never dared you to do anything this risky,' I replied. 'Oh yeah? Walking around the mall in a pink latex micro-skirt and no panties wasn't risky? My balls were swinging around for all to see!' 'Yeah... Read full Story
shemale lover 2012-02-26 3,489 dildo Sex Toys
100%
Sissy Training
This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We&r... Read full Story
shemale lover 2012-03-12 8,073 Group Sex Fetish bdsm
83%
A Man's Place
I couldn’t believe my luck, a raise! Finally, after working three years in this stinking company as Marketing Manager, and I finally get a raise. Okay, granted, it took for the company to be bought out, have a number of people sacked, and to squirm like mad to do it, but I got there! 5000 quid... Read full Story
shemale lover 2012-03-18 3,318 Stockings Fetish cum oral feminization
100%
European Vacation
I was 18 when I first went to Europe. That month would change my life. My parents had died when I was five, and I was raised by family friends; they also controlled my trust fund. It's not a coincidence that I went to Europe just as I came into control of the money. I loved my foster-parents, but... Read full Story
shemale lover 2012-04-21 3,761 anal sex cum oral sex sissy
83%
Been Caught Cheating
My story begins about a year ago. I had just moved in with my girl friend and we were completely in love. I was 22 and she was 23. Her name is Angela. She is 5'7'', 120 pounds, hour glass figure, C size breast, ghetto booty, light skin, long dark hair and green eyes that pierce your soul. She is and... Read full Story
shemale lover 2012-04-22 5,183 oral sex Sex Toys cum swallowing crossdressing
90%
A Sissy (S)exercise Fantasy
I stopped going to the gym about six months ago, when money got tight and I had to find ways to reduce my expenses. I usually don't get to the gym much in the spring or summer months anyway, so it was an easy expense to cut. I hate going into the office all sweaty, so I avoid working out in the morn... Read full Story
shemale lover 2012-06-14 9,244 Cumshot Fetish domination oral sex sissy
100%
Demoted and...
1) Dinner at Riverside All the note said was "Dinner. 8:00. Riverside Grill." It was in my secretary's handwriting but I knew it must be a message from Carrie. Andrea, that's my secretary, always hated taking messages from Carrie and would only write down the most important parts. River... Read full Story
shemale lover 2012-08-17 3,459 Cumshot oral sex cum swallowing
50%
Polish Maid
'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, l... Read full Story
shemale lover 2012-09-01 4,719 Stockings Crossdresser Cumshot sucking heels
50%
Alex
Alex and I had been friends forever. We had been neighbour's on the same street, attended the same schools, hung out with the same friends, even dated a few of the same girls. Alex had blonde hair that was kept medium in length, brown eyes, was fairly short for our age, scrawny, and always wore a... Read full Story
shemale lover 2012-09-22 3,840 Cumshot oral deepthroating
80%
In Panties
From a very early age I have been wearing panties. I am not really interested in dressing further, at least not yet, but I love wearing silky feminine panties. The more feminine they are the more I like them. I love lace and flowers, and I love wearing them under my jeans when I go out. Whether it i... Read full Story
shemale lover 2012-10-15 4,960 anal sex sucking Big Cock cum
100%
An Unexpected Birthday Gift
It was my best friends birthday and I was taking him out for a night on the town. We have been best friends since we were kids and I was going to give him a special present. We started the night out with dinner at a nice sit down restaurant where we had a few beers and some really good steaks. This ... Read full Story
shemale lover 2012-11-17 3,366 Cumshot oral sex cum swallowing
100%
Dress Up
I don't know how to explain it. I am not gay although I may be passive bi. I have had sex with men, but not a lot and I have always been the one receiving, you know once a friend showed me a pack of pictures of his wife from fully dressed in conservative suit to complete nude with some action photos... Read full Story
shemale lover 2012-11-17 4,431 Fetish cum oral sex Sex Toys cum swallowing
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,498 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
91%
Hot Night on the Town
This is my first post, hope you enjoy. May continue the story if I get positive feedback. It was my 21st birthday, and my friends were taking me out for a night on the town. We had been going from bar to bar, getting d***k and trying to pick up women. Finding no luck with the woman at the bar we we... Read full Story
shemale lover 2013-04-19 5,377 Cumshot suck shemale facial oral sex
77%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 71,545 Teen (18+) Crossdresser transgender sissy slut.trinity