Sort by
Relevancy

Free Stories

87%
Beaches
A couple of things you should know about me: I'm not gay; I've always had this thing for dark-skinned women. I graduated from the army at age 21 and headed home to the Bronx. Me and a buddy of mine started up a livery car service. We started with four cars. 15 years later, we had 100 cars and alm... Read full Story
shemale lover 2012-01-03 5,310 Fetish shemale Ebony
78%
My BBC Friend
I was back in Indianapolis this past week. I had not had a good fucking for some time and was hoping to hook up with my friend Terry.I had hooked up with Terry several times when I was in town. He has an amazing cock. he can fuck for hours and loves to make love to his sissy slut. I got to the hote... Read full Story
jinnirogers 2016-11-22 6,797 tranny suck interracial sex dildo cumming bbc
100%
Reaching Paradise on Game Night
Reaching Paradise on Game Night by Sabrina G. Langton * Author's note: Here is one of my most popular stories. I get so many messages and emails about it and it makes me thrilled. I am so glad it has taken on a life of it's own. 'A wife learns a little too much about her crossdressing hus... Read full Story
Brina Giselle 2024-08-08 3,210 anal Stockings Crossdresser Blowjob pantyhose transgender wife dress-up
66%
The Coma Girl Brain Transplant
[This frivolous story is something I put together as an entry for a comedy competition earlier this year, not to be taken at all seriously, a bit more sci-fi than erotica, more of a mind-fuck than anything else so it’s not jerk-off material but hopefully some of you might still enjoy it] Thankful... Read full Story
cara_elaine 2017-12-19 6,932 Crossdresser Uniform domination
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 12,103 Bareback cum ass fucking slave
100%
Flowers in the Heart Part 2
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 6,657 sucking oral sex facefucking
100%
White TV + Black Gangsta - 1st Date
I was having another somewhat boring evening alone. My name is Jill (when I put on women's clothes, that is) I was sitting at my computer, checking out the chat rooms on AOL. Just moments before, I had shed my male persona and taken a long hot bath, followed by a sensuous body shave that had left me... Read full Story
shemale lover 2012-11-19 3,703 anal sex cum oral sex kissing
94%
First CD experience
I was having difficulty hailing a cab after a night out when I saw her walking towards me. A slim blonde in big heels, black fishnets, a pale pink mini skirt and a snug fitting black playboy bunny top exposing her midriff. Anyone would have spotted her a mile off. At this point I was quite simply lo... Read full Story
bareambition 2013-06-28 5,946 suck fingering ass fucking facial 69 fishnet cd
100%
I Knew Her Secret
I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... Read full Story
shemale lover 2011-09-20 6,847 Cumshot asshole fingering
66%
The wonderful adventures of miss K: Down by the river...
Miss K and Tracy walked through the park by the Gateway Arch, content to spend a nice spring day enjoying the outdoors instead of another piece of flesh. Tracy had one a pair of short, tight daisy dukes with a light pink crop top that showed off her tight stomach and nice legs. Miss K herself... Read full Story
shemale lover 2011-12-01 4,561 shemale oral ass licking nipples
100%
I Knew Her Secret..
I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... Read full Story
shemale lover 2012-04-04 5,227 anal sex Cumshot fingering
100%
Bagging a Bitch with Balls
Watching porn has given me a lot of ideas concerning what to do in bed--and elsewhere. Some of the guys and sluts in X-rated videos do it outdoors--in the woods, a park, poolside, or in a parked car. Some chicks flash their dicks--yeah, I watch shemale movies sometimes, too--in public places, and so... Read full Story
shemale lover 2011-09-27 5,823 transsexual ass fucking tit fucking
71%
Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
shemale lover 2011-12-02 12,930 taboo Fetish crossdressing erotic encounters
85%
Hotel Surprise
Working in the big city has it's perks and drawbacks. The other night some of my coworkers and I went out for a small celebration at a local restaurant. Everyone ordered drinks and we enjoyed our latest professional success. Finally the crowd thinned out and I was leaving with some others. One of th... Read full Story
shemale lover 2012-06-16 3,760 anal Cumshot shemale oral missionary position
100%
Afternoon Delight Chapter 3
When we got to the cottage, the girls stripped me of my jewelry and took theirs off and poured me into the shower. They washed the cum off of me and got me hard again. Damn, Ally and Carmen were all over my cock, giving me a work out. Needless to say, I came a few more times, and we got into the hot... Read full Story
shemale lover 2012-08-27 2,822 Group Sex facial sucking off
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,882 first time ass Cumshot suck cd sissy make up
50%
Exotic Escapades Chapter 1
"You're an interestin' one," the guard said, leading Tammy down the corridors of the prison complex. "So what you mixed with?" "Blasian," Tammy replied, almost in a mumble. "Well I'll be," the guard smiled. "Niggasian?" He stopped Tammy and ... Read full Story
shemale lover 2012-05-05 2,957 anal sex Creampie oral sex
100%
Fender Bender Chapter 5
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. Mom and my Step Dad were away on vacation leaving me home alone. The past several days I had been very lazy and sleeping almost to noon. So it was no surprise ... Read full Story
shemale lover 2012-07-26 3,493 Crossdresser Cumshot Fetish oral sex cum swallowing
100%
Whatever Your Heart Desires Part 6
I was excited about going out with Lexi, more so than I had been about anything in the months since Danni left. The prospect of spending my birthday alone, without my sweetheart, was just too daunting. Being dragged out of my self-imposed exile for a night of drinking and dancing actually looked lik... Read full Story
shemale lover 2012-12-09 4,067 Stockings shemale transformation
100%
Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
shemale lover 2013-01-30 8,359 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
80%
Chapter 2 - Cuckold Cruise
If you read Chapter 1, you know how I’ve been a weak, submissive sissy my whole life. My tiny nub of a penis never fully developed has never been inside a woman. I was fortunate enough to find and marry a strong and beautiful woman who accepted my submissive nature but only learned the full scope ... Read full Story
Sissy Annabelle 2022-10-07 5,940 Interracial crossdressing sissy cuckold chastity
88%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 68,395 Fetish shemale oral feminization
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 8,503 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
100%
Caught by the Past
Your latest girlfriend, Karen is very kinky and she introduces you to all manner of strange people. You on the other hand are rather naive and innocent. You found one handsome guy, James strangely attractive. He has long muscular legs, a washboard stomach, dark skin, blond hair and an impeccable spe... Read full Story
shemale lover 2012-06-28 2,834 Stockings Fetish crossdressing
100%
Betrayed Chapter 7
Angie kept my arm locked in hers, preventing any attempt at escape. We caught a cab back to my place. She was even more appreciative of it than Dianna had been. "Girlfriend, you live like a queen!" she exuded. Realizing what she had just said, she giggled. "Oops! Well, you kn... Read full Story
shemale lover 2012-05-30 4,167 Fetish Lingerie crossdressing
80%
Daniel, Dani, Dana Part 2
Looking in the mirror as I drove the highway, the new me felt and I thought looked great. A new hair color with the old one the trim, my face looked smaller and even more feminine. I never had this freedom at home and hated the idea of going back there. Final exams were all that was left to shed the... Read full Story
shemale lover 2012-06-08 4,023 anal sex Cumshot Fetish crossdressing
80%
Chelsea cumdump series intro
Let me begin by telling you a little about myself. My name is Chelsea, I am a 24 y/o transexual, and I abso-fucking-lutely LOVE sex. Cock, cum, the works. The majority of this and the stories to cum are actual facts and events from my life. I have always had a feminine body, even before my transitio... Read full Story
ts_chelseacumdump 2011-11-19 4,242 Bareback shemale slave
33%
Superstar fun - an evening to remember!
Starting with a little history, let me say that I started getting into tranny fun back around 1990. I went on a visit to New York and had always been an avid reader of Screw magazine/ newspaper. Before the Internet was in full-bloom it was distributed nationally to all cities around the country and ... Read full Story
shemale lover 2012-04-03 3,363 anal sex cum ass licking oral sex 69 position
100%
Sex with strangers in public bathroom
I always had a sexual fantasy of dressing up as a chunky sexy slut tranny and visiting a known public mens bathroom close to my house and giving oral sex and what ever they wanted me to do for them sexually.Well I finally got up the courage to do it and before I go into my true first time experience... Read full Story
shemale lover 2012-10-01 5,312 anal hardcore Creampie Fetish oral fingering
100%
Tales of a cocksucking manwhore...
I'm sitting at the bar in a shemale hangout in a seedy part of town. I'm having a cocktail and talking to two shemale's, a tall black girl named Nessa and a redheaded white girl named Lucy, both very sexy and erotic. In the course of our conversation Nessa asks me what is the one sexual experience I... Read full Story
Johnson Long 2024-09-02 2,304 Blowjob gangbang cum in mouth
100%
TS Prostitute Urge
After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possibl... Read full Story
shemale lover 2012-01-27 3,919 Group Sex sucking cum
100%
Abducted and Turned Out Chapter 2
2: Fun time So, after I blew the guy downstairs and told him to come and knock on my door and pay me to blow him again anytime, I went up and took a long hot shower and put on a nighty and went to sleep. I slept surprisingly well considering I had just spent a long night out selling my ass. I tho... Read full Story
shemale lover 2012-08-10 4,900 Crossdresser anal sex sucking Creampie facefucking
100%
Whore into a Housewife
I put on my beautiful long red hair to finish my ensemble and transformation from man to woman. I had been talking to a guy for a while about role playing with him and we were finally going to do it. It was funny, I hadn't actually met him face to face, but I felt like I had a connection with him, a... Read full Story
shemale lover 2012-11-12 3,080 Cumshot Fetish oral sex crossdressing
93%
My First Night of Being a Sissy Cumdump
Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved... Read full Story
shemale lover 2013-12-08 21,874 Crossdresser suck Creampie Blowjob ass fucking cd
66%
a day in the life of Amber SissyZofen 264
And the days had passed one after the other and now it was the day of my date. He sent me a txt at 8.30 on Saturday morning to say he was coming And you remember he was leaving his phone at home in case his wife called You know I had sent him my address, parking advice and left the gate ajar. ... Read full Story
amberdoll 2020-09-15 3,078 Stockings Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie Homemade cum in mouth
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,678 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
50%
The Greatest Lie Part 6
In my rare moments of leisure in the weeks following my close encounter with death, I had had little opportunity to talk about it. Of course, the police had asked perfunctory questions, and I had testified at the coroner’s inquest, but until my next appointment with Dr. Erika Wright, I had not... Read full Story
shemale lover 2012-01-19 4,895 hardcore erotic encounters fantastic
80%
My Sex Change
It was the day I had been waiting for. My bags all packed, two years of saving and working hard and I could finally go on my round the world trip. I said goodbye to my friends and family and checked myself onto the plane. First stop; London. With my final waves and promises to return with present... Read full Story
shemale lover 2012-04-01 4,732 sex change jerking crossdressing
100%
A Slut is Born
There I was, one week before the end of high school. Going to college in the fall. Nice car, good family, 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 m... Read full Story
shemale lover 2012-06-26 6,773 anal sex Fetish oral facial feminization
96%
How I Really Got My BA In College
I was living in an off-campus apartment building two months into my first semester of a two year BA program. I lived on the 22nd floor and my three friends Ray,Jim and Dan lived together on the 13th. As it was Friday night I threw a couple loads of laundry into the wash and went downstairs to cadge ... Read full Story
shemale lover 2013-02-12 6,470 Cumshot sucking Blowjob ass fucking swallowing
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 8,213 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
93%
Sissy Maddie's New Apartment Gangbang
I’d just moved into the big city. Me on my own in a cheap apartment block. The flat was nothing special by any means, and the room next to mine seemed to be noisy with parties. But I was glad to be on my own. I had almost finished unpacking my belongings when I came across my stash of female clothi... Read full Story
sissymaddiex 2020-09-25 10,673 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
Becoming a Chrissy - Chapter 1
I always knew I was a little sissy slut. When I was ten, I took a pair of my mommy’s panties to try on. It was a hot pink G-string that my petite mother must have worn when she was ready to get fucked by my daddy. It was just the right size to cover my prepubescent clitty and also stretch through my... Read full Story
mindlessrobot45 2024-05-13 4,702 Crossdresser Blowjob blonde femboy cum in mouth
94%
What If My Mom
Country Boys with a Difference I loved my Brother's cock, don't get me wrong, it's just what happened and our Mother loves our cocks as well as she loves our breasts. Let me explain. It all happened when I was 13 and my brother was 11. Ours was a happy family living in the hill country of Kent... Read full Story
shemale lover 2012-06-14 16,975 shemales taboo Group Sex
50%
My First Time Out Part 4
It was Sunday morning at eight o’clock when the phone rang. Shayna’s eyes felt like they were glued shut but managed to answer the phone on the third ring. “Morning,” said Shayna as she was still half-asleep. “Good morning Shayna. This is the Bell Captain calling.... Read full Story
shemale lover 2011-10-18 4,870 cum oral facial deep throat fucking
100%
First Time Drag
My computer crashed.... again! This time it was worse though, I couldn't reboot, the damn thing wouldn't even restart. I occasionally work out of my home where a working computer is mandatory. I decided to cool off a bit and walked to the local convenience store where I bought two bottles of a dry c... Read full Story
shemale lover 2012-10-12 3,440 Cumshot sucking tit licking
88%
A Fantasy in Pantyhose
I always go out to the same bar on thursdays. The women are hot and long legged and they always wear pantyhose. Like usual, I dress in jeans, collared shirt and a jacket, deck shoes or dress shoes. Underneath, pantyhose. Always sheer to waist, no underwear and always nude. My jeans are long enough t... Read full Story
jonezn4ph 2012-11-24 6,687 anal pantyhose crossdressing gay
72%
Sissy's Cherry Got Popped!
S)heplacement- Definition- Any sissy male that is willing to take the place, or replace any woman who is not properly taking care of their man inside or outside the bedroom... These gu(y)rls will make sure their makeup and lipstick is just right, their lingerie is matching, and that they are always ... Read full Story
Kevyn-JeanneHarris 2015-12-20 9,955 anal sex submissive sissy cross dresser
70%
Play Day for Sara
It doesn’t happen often, but an opportunity opened up for me recently to take a day off to get a hotel room, get dressed, and entertain men. So I took it. When I discovered I would have this day to myself the previous week, I ran the following ad on craigslist: “Get ready boys – t4m super horny... Read full Story
saralovescd 2017-05-02 6,771 anal sex oral sex crossdressing Craigslist hotel room tag team
75%
My First Time Out Part 1
Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms w... Read full Story
shemale lover 2011-10-17 4,729 first time cum oral
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 4,721 blonde shemale massage
94%
The Babysitter's Secret
The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated... Read full Story
shemale lover 2011-10-24 21,636 Blowjob perky tits handjob titfuck
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 4,626 hardcore crossdressing fantastic bondage and discipline
25%
Adult Bookstore Dancer
Adult Bookstore Fun At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make abou... Read full Story
shemale lover 2012-02-26 4,476 sucking Fetish cross dressing
33%
Click, click, click....
Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will th... Read full Story
shemale lover 2012-06-09 5,822 anal Cumshot oral deepthroating
100%
Caught by the Past Chapter 3
After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your lap. Dressed like a sissy whore you relax as best as you can, your arse muscle stretched wide open by the butt plug. But you've become accustomed to all the strange feelings... Yo... Read full Story
shemale lover 2012-06-28 3,508 Fetish oral sex crossdressing