Sort by
Relevancy

Free Stories

100%
Modified Covers
As a hobby, some artists enjoy modifying vintage magazine covers so that their original topics are transformed into transgender themes and shemale models replace the female faces and figures that originally graced the periodicals' covers. In the process, the titles of the magazines are sometimes cha... Read full Story
shemale lover 2011-09-09 3,679 transsexual transvestite transwomen
100%
Joanna the Tranny Prostitute
Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stop... Read full Story
Joannacd1 2011-11-07 4,678 tranny Crossdresser Ebony
66%
Lana: Second Encounter
Well, you may remember the satisfaction I felt at the end of my first encounter with Lana. I had not really expected to find a CD with whom I felt so comfortable. Usually, I had left my experiences with some discomfort about the surroundings or the person I had been with. Not in this case, she was... Read full Story
shemale lover 2011-11-11 3,499 pantyhose tgirl anus
0%
Lady Denisa's Gang Banged
The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... Read full Story
shemale lover 2011-11-22 4,830 shemale oral orgasm
88%
I went back for a male massage...
After my last visit, as I said my head was spinning...I'm not gay, but I loved being used that day...have a cock in my mouth and in my ass??...but, I loved it...so here I was again...when I went in, I didn't see the same staff...it was asain women this time...???...ok, this can still be fun but...A ... Read full Story
shemale lover 2011-12-14 4,167 anal shemales gay male
50%
Dirty Tranny gang bang
Deep breath Charlotte, step into the night air and strut your stuff girl. This is what I was born to do; I snuggle into my short white fleecy coat as my 5” platform heels click on the pavement. Glancing down I can see my shapely stocking clad legs and, the all important, ankle bracelet glit... Read full Story
shemale lover 2011-12-27 5,071 anal shemales Group Sex
25%
How I Learned To Love Drag Part 1
"How about doing a sports interview?" I suggested. "We could have hockey's dirtiest player doing a tell-all about how to inflict pain without taking a penalty." "Yeah," agreed Ted. "The bad guy could demonstrate all his dirty moves on the interviewer. Like an el... Read full Story
shemale lover 2011-12-29 3,020 crossdressing erotic encounters fantastic
80%
Mandy Awakens Dave's Desires
We had been flirting across the bar for several weeks at this point. She was just so easy to talk to. Although she wasn't stunningly beautiful, she was quite attractive. Mandy is about 5'2" or so, 110 pounds. She has a light complexion to go with her strawberry blond hair, which she wear... Read full Story
shemale lover 2012-01-10 5,316 anal sex cum oral fingering
50%
The Greatest Lie Part 5
Most of my classmates celebrated the first Saturday after the beginning of classes in hedonistic leisure, nursing hangovers and playing Frisbee on the Quad. But I spent the morning plotting my escape from this dangerous, macho dormitory, studying want ads and making appointments to look at studios o... Read full Story
shemale lover 2012-01-19 4,210 hardcore erotic encounters fantastic
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 4,637 hardcore crossdressing fantastic bondage and discipline
0%
The Greatest Lie Part 16
As soon as we were safely back in our hooch, I retrieved the iBook from its hiding place under the floor and opened up Spartan's main Excel spreadsheet. I re-sorted the list against the data from the last three weeks of our frustrating field work, by district, language group, age, and every other ca... Read full Story
shemale lover 2012-01-20 5,391 first time femdom crossdressing
100%
Barbie Jo Adventures Part 6
Saturday When I woke up, I was alone in Harley's bed. I went to the bathroom for the usual thing when you first wake up in the morning. I looked at myself in the mirror and saw me, a guy. I felt embarrassed being in Harley's house with no makeup on. I had a quick shower, borrowed Harley's razor t... Read full Story
shemale lover 2012-02-18 4,696 cum oral face fucking
50%
A Married Marilyn
"Class is dismissed. Don't forget the project due…" "Huh, what?" Marilyn woke up disoriented from her nap. When she finally came to, she vaguely remembered some project for Intro to Computer Science, gathered her legs from the chairs in front of her, dusted off her b... Read full Story
shemale lover 2012-03-18 7,600 Group Sex Masturbation sucking Sex Toys
50%
A Murder Misstery Aloft
For those who came in late, Matt McCoy – now Madeline Moreau – is on the run for a crime he did not commit, and a murder which she did....after discovering a shocking secret about her past, Maddy spreads her wings, and more. The journey from St. Martin to Montreal, on a charter flight... Read full Story
shemale lover 2012-03-21 4,134 Fetish fingering
100%
A Natural Sissy Part 3
The Reward Once we were at home, I still couldn't keep Stacy quiet. "When do I get my reward, Mistress Gail?" repeated every other breath. Constantly. Finally, after I had changed into my bedtime attire (a pair of 4-inch heeled mules, and a see-through short nylon robe, in pink, like my... Read full Story
shemale lover 2012-03-24 4,045 foot fetish sissy whipping
100%
Buying Time
It’s a hundred dollars to use the sex machine in the public restroom. Insert a couple of fifty-dollar coins into the payment slot to remain anonymous, though of course it’s more convenient to just let the data terminal do a neural scan and auto-debit your account. A hundred bucks buys... Read full Story
shemale lover 2012-03-25 4,191 anal sex Cumshot shemale
100%
Neighborhood Restaurant Surprise - Kimi
I - The Meeting In the neighborhood restaurant I frequented weeknights after work, I had developed a friendly relationship with several of the college kids who worked as servers. Always having been attracted to the most feminine and petite of girls, dark, almond shaped eyes being a super plus, I ... Read full Story
shemale lover 2012-04-11 5,554 anal sex Cumshot fingering oral sex small breasts
100%
Planet Of Men
At 1600 Eastern Standard Time (EST) on September 27 in the year 2020 AD the UN announced that General Atomics Corporation (GAC) had saved the world. After years of panic in every country that the world was doomed due to the effects of global warming, GAC announced that, with funding provided by the ... Read full Story
shemale lover 2012-05-04 4,455 first time Stockings facial oral sex transvestite
100%
Threeway Heaven
Times were tough and I took a job as a bouncer in clubs on weekends. It was a pretty boring job most nights, and frustrating having to deal with drunks all the time, so my boss sent me out to a gay club for a change of pace. Also, I was one of his few workers who wasn't homophobic, and therefore les... Read full Story
shemale lover 2012-05-10 3,470 Group Sex Cumshot sucking fingering
85%
Transsexual Cheerleader
Transsexual Cheerleader Marcus, the football team quarterback, was well known at the university as the "most datable on campus", and he had had his share of women. From the nice virginly freshman, to the hottest senior whores. It was no wonder that he was so popular. 6'4, 240 pounds of pur... Read full Story
shemale lover 2012-05-13 4,099 anal sex Creampie Blowjob
100%
Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
shemale lover 2012-05-29 5,514 Cumshot orgasm condom sex
100%
Fender Bender
It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... Read full Story
shemale lover 2012-07-26 8,780 Teen (18+) Fetish crossdressing
100%
Fender Bender Chapter 9
My name is Robert, I have been cross dressing since I was 14. I turned 18 last summer and this story takes place during my senior year in High School. I am 5'9" 160 pounds, blonde hair and blue eyes. When I am dressed I call myself Vicki. __________ I had met Julie at a recent party. Well... Read full Story
shemale lover 2012-07-27 3,741 Group Sex Cumshot Sex Toys
100%
One Special Night
Marilyn called me at the office with just three words. "It's on tonight." After a few moments of listening to the silence on the other end of the disconnected call, I realized what she was referring to. Immediately my cock began to swell, sliding slowly inside my satin panties unti... Read full Story
shemale lover 2012-09-02 4,743 Stockings Cumshot Masturbation Fetish Blowjob
100%
Hidden Surprise
After staring at Angela's crotch for what seemed to be forever, the shocked young woman asked, "I-is that what I think it is???" "I guess it depends on what you think it is," Angela replied softly. "But how, why???" Midori asked. " I mean you have a cock for christ... Read full Story
shemale lover 2012-09-17 3,197 Cumshot oral sex
83%
With an 'E' Chapter 2
Waking the following morning, feeling somehow fulfilled. Then, as I came to, I remembered the night. With my frilly shortie nightie disgustingly clinging to my body, back and front, came the realization "I was no longer a virgin!" And -- it felt great. Sometime in the night, Bobbey had ... Read full Story
shemale lover 2012-10-10 2,802 sucking Creampie kissing
100%
Alleys
My mother told me never to take a girl into an alley at night. She went on about how dangerous they were, with strangers lurking in dark doorways waiting to do horrible things to the people who wander in alleys. Alleys can be dark, imposing and dirty especially in the city. I spent my youth avoiding... Read full Story
shemale lover 2012-10-14 4,723 anal fuck orgasm
85%
First Time for Everything
At the time I was living in Paris and on sheer whim, I decided to go to Amsterdam for the weekend. I thought to myself, "what better place to act out my fantasies than in Amsterdam?" I packed some of my slutty clothes. I decided on my slutty cowgirl outfit complete with flannel top, jean s... Read full Story
shemale lover 2012-10-14 4,615 anal sex orgy facial huge cock sucking off
100%
Double Wedding
I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years ... Read full Story
shemale lover 2012-11-08 7,659 Cumshot dildo Sex Toys
100%
What Life Throws at You
Kind of funny what life throws your way. Some times fate can be a fickle bitch. My name is Rick Tyler and I'm a cop. Well, detective actually. At least I was until 30 seconds ago. I dropped my badge and gun on the desk of the idiot that pretended to be my boss. Baker looked at me with distain. We ha... Read full Story
shemale lover 2012-12-15 4,625 oral erection kissing
100%
Annoying Roommate
My name is Mike I'm 24 years old right out of college entering the workforce as a entry level pharmacist. I'm about 6'2 about 180 but being so busy studying for the past few years my body is a bit soft. I always have been bad with women, I'm what you call the typical nerd/geek/loser. I live in a sma... Read full Story
shemale lover 2012-12-15 5,410 Cumshot oral
100%
The Meeting of Cortney and CiCi p1
Cortney could not keep herself from thinking about the upcoming date with CiCi as she sat in the luxuriant bath water and shaved her legs. She planned to fuck the glam slut whore long and hard. But first, the metamorphosis to turn her into the dome bitch - Cortney. She rose from the bath, patted... Read full Story
shemale lover 2013-04-15 3,900 suck shemale oral Lingerie make up
100%
Pounded to submission part2
Two days ago Joesph was checking out porn. A couple of BBW vids here some interracial there, the usual. Then he saw a just viewed picture with a Brazilian She-male and couldn't stop looking. With his curiosity getting the better of him he clicked on it. She was gorgeous! Her face appeared to be as f... Read full Story
shemale lover 2013-04-21 8,259 Cumshot suck shemale oral deep throat
100%
My second time
after failing to loose my virginity,i decided to try again. my man friend love to fish and would make his way to inch early every sat morn. being a creature of habit he always returned at the same time. one sat evening i accidently on purpose bumped into him on his way home. standing at the side of ... Read full Story
shemale lover 2014-07-21 4,466 anal Cumshot suck fingering swallowing
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 7,501 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
51%
Amara Vadillo ( Sylvia Boots )
Vadillo was born and raised in Cuba. After emigration to Los Angeles she became Amara. After injections of hormones and silicone, she was a 34 DDD. She found work acting in shemale videos and performing at the West Hollywood Club 7969 under the name of Sylvia Boots. She became known for her love of... Read full Story
✘Transensual✘ 2017-10-10 9,585 shemale Vintage boyfriend silicone hormones