Sort by
Relevancy

Free Stories

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 7,843 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Clara Bow's Academy for Ladies
Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his an... Read full Story
shemale lover 2013-03-27 4,958 Teen (18+) Small Tits shemale public softcore
80%
JUERA MARICON
My name is Keven Jeanne and, Yes, I am a Sissy! When I was 13 I put on my mom's panties and some of her lipstick when she was at work. I had longish blonde hair and I ruffled it up - kind of teased it up - and when I looked in her dresser mirror, I almost ejaculated. Because what I saw looking ... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,240 blonde shemale submissive cocksucking
63%
A Slice of Life - Ch. 1
Written by Nobody Home. All comments and feedback welcome! 1. It is dark out, night descending upon a wintery, snowcapped city backdrop. Cold against the windowpane, I feel my head shoved into it and my hand makes a streak against the glass. My would-be attacker tears my panties off of my slen... Read full Story
Nobody Home 2016-12-20 5,103 ass fucking cumming Guy Fucks Shemale cd sissy
82%
First time with a trans escort
I've thought about seeing a t-girl escort many times and a few weeks ago I finally made a date with a local girl named Carol. She´s a lovely Colombian girl with long dark hair and a slim, sexy body. She welcomed me into her home wearing a sexy black dress and high heels and after pouring a d... Read full Story
Gracemel121 2017-03-28 19,291 anal Amateur Cumshot shemale escort top
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,503 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 8,979 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,570 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
100%
Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
✘Transensual✘ 2019-02-27 5,736 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
100%
Cheating Sissy Wife chapter2
My sweetheart Keith is back from his road trip and we were about to make up for lost time. He didn’t even want me to fix dinner. Instead he said that we would order pizza later. Meanwhile we started making out right there on the couch. We were both horny and anxious to get next to each other. I felt... Read full Story
Regina10 2020-10-26 4,696 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
My favorite fuck part 1
Your responses and views have been a desirable response and encouragement for future stories. I’m just a guy, who wishes to be a girl, wanting to be seen and accepted as a female. So Thank you. I’m hoping to make more stories, and more to those willing to see me, and accept me. Much love :) Y... Read full Story
Mistysis 2020-11-02 2,790 Stockings Small Tits Crossdresser Guy Fucks Shemale
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,519 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Ravaged by Daddy
For anyone who loves wearing high heels and dressing up to get ravaged by your hungry Daddy. I imagine you laying on your side as I run my strong hands up and down your smooth, soft legs and across your feet. I slowly slide them upwards until I'm caressing and squeezing your thighs. You watch me ... Read full Story
TheWinkster 2023-08-29 5,019 anal Cumshot Bareback Creampie Guy Fucks Shemale
66%
You Just Don't Care...
“Oh, naw! I’m straight,” the slim, sinewy-built man replied matter-of-factly to revelation. “What’s that got to do with anything,” cooed the milk-chocolate-complected vixen, playfully grazing the man’s hard chest. “Damn, why you ask it like that,” he scoffed. “Like what,” the sing-songy-voiced c... Read full Story
Faggyboi and Puzziboi 2023-10-19 5,733 anal Crossdresser Ebony Guy Fucks Shemale sissy femboy bbc faggot faggyboi puzziboi
100%
Nikki's Massive Strap-on
A quick recap in case you haven't read my previous stories. My name is Kacey. I'm 20 years old, white, 5'10" and 150 lbs. I have straight, shoulder length dark brown hair, light brown eyes and a thick, 6" cut cock. My girlfriend is Hannah, who also 20 years old and stands 5'10" weighing in at 140 lb... Read full Story
KaceyKlarissa 2024-02-23 4,598 anal Crossdresser Big Tits Cumshot Fetish Big Cock Lingerie Shemale and Girl domination big ass Futanari sissy cum in mouth
100%
Additional Thoughts on Sodomy
Although, in the world (or worlds?) of pornography and erotica, it is politically incorrect, perhaps, to suggest that the body, whether male or female, is not built for anal intercourse, the fact is that anyone who has participated in this act (especially on the receiving end) or who has enjoyed wat... Read full Story
shemale lover 2011-10-05 3,924 Creampie sperm anus
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,249 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
Buying Heels
I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer ... Read full Story
shemale lover 2012-09-30 4,639 Stockings Cumshot oral sex crossdressing
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 3,368 anal sex cum oral sex kissing
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,250 torture extreme fiction bondage and discipline
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,231 anal shemales Group Sex
100%
Francis Meets a Black Stud Part 2
The first story was easy and this one went by pretty well. If you have any thoughts or suggestions for where Francis should go in installment #3 email me. I will respond to your email and sometimes I will send out previews of what I am working on if you treat me right. Thanks. As I was walking to... Read full Story
shemale lover 2012-11-20 3,717 Stockings cum Ebony oral
83%
How Kevin Became Finesse
Monica went out with JJ! He was a black buff guy who taught karate where she took the kids. He drove a yellow corvette and liked to wear shirts with the sleeves cut off - to show off his big tattooed arms! All the young blonde girls were on his jock, but he had the eyes for Monica. She kept protesti... Read full Story
Kevyn-JeanneHarris 2015-12-20 4,413 sissy cross dresser cuckold
63%
My Mistress, My Slave
I first met Robert as I was moving into my new apartment building. He was just one of the several men who appeared out of the thin air and offered to carry my furniture and boxes up to my new second story apartment. Most of these manly he-men only appeared because they wanted to get to "know&qu... Read full Story
shemale lover 2012-01-18 7,767 suck crossdressing erotic encounters
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 30,746 strapon porn
73%
Black Girls Have Big Dicks
She was like no woman I had ever seen before. She walked into a room and everyone's eyes were on her. She just had that incredible presence that just lit up the room and everyone just wanted to be around her. I was working behind the bar of a trendy club when I first saw her saunter in on her long l... Read full Story
shemale lover 2012-06-27 21,210 anal sex oral sex black cock
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,188 Crossdresser sucking Big Cock ass licking big boobs
91%
Birth of a New Sissy Part 1 Encounter
I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent ... Read full Story
shemale lover 2011-11-17 5,254 cum Sex Toys crossdressing
57%
Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
shemale lover 2011-12-23 6,296 transgender toys bondage and discipline heavy
100%
Permanent Stay in Mastersville Part 2
I had some time to think about this as she dragged me out the front door and threw me into the backseat of her car, shut the door and left me there as she went back into the house. I sat there in the car thinking about what would happen to me, if Mistress had really meant what she had said about tur... Read full Story
shemale lover 2012-01-08 4,309 toys bondage and discipline heavy reluctant
66%
Cassandra Chapter 1
Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these ... Read full Story
shemale lover 2012-03-27 5,791 sucking fuck orgasm crossdressing
50%
The Making of A Sissy Part 10
Bella quickly gulped down her vodka and cherry, her bottom tingling with anticipation as her new mature friend gave her a commanding look; she had so enjoyed being submissive for her at the end of a leash, and now she knew she would be bound tightly on a soft inviting bed, and made completely helple... Read full Story
shemale lover 2012-05-29 4,427 dildo oral sex Sex Toys sissy
25%
A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
shemale lover 2012-07-05 6,804 Creampie Fetish crossdressing virginity
50%
Clinton
"How many inches?" she asked. "Twelve," he said. "Really?" "Really." "If you're lying, you're just wasting your time." And mine, she thought. "I'm not." "Okay, then. It's a date." Tiffany hoped the jerk was te... Read full Story
shemale lover 2011-09-19 10,575 Big Cock cunt anus
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 8,893 Stockings sucking domination
80%
Aunt Cindy's Bizarre World Part 2
Chapter 7 I am guessing it was just over an hour until I heard the door open. It was her again, Miss Sindy Satin my auntie. This time she was wearing just an under bust white satin corset, long boots in satin exactly like mine but in white and her long, white bridal satin gloves and a the ribbon ... Read full Story
shemale lover 2011-12-02 7,869 taboo Fetish crossdressing sentimental erotic
50%
I am Baaack! Part 1
PROLOGUE: Ross Thorn, aka Nick Mitchell, paced back and forth in his office high up in the Hancock Building. He glanced out the corner windows. North you could see out over Chicago's North Side to almost as far as Wilmette, and east out over the lake almost to Michigan. It was a perfect spring da... Read full Story
shemale lover 2011-12-15 5,267 crossdressing erotic encounters
100%
Debbie Part 8
Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... Read full Story
shemale lover 2011-12-23 7,233 transgender toys bondage and discipline heavy
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,057 sucking Fetish fucking sissy
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,084 sucking Fetish Uniform domination big boobs
50%
I am Baaack! Part 4
It was 2:00pm, exactly five weeks after The Meeting. Jessica stood fidgeting behind the Vaingirls cash register. Things had returned to seeming normalcy after The Meeting, but all the secondary participants in Rose's plan knew it was like the Phony War of 1939/40, and that things were being done beh... Read full Story
shemale lover 2011-12-15 2,503 crossdressing erotic encounters fantastic
71%
Glory Hole Girlfriend
My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... Read full Story
shemale lover 2011-12-18 7,253 Creampie ass fucking mouth fuck
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,143 Fetish transformation dildo
50%
DU VILAIN PETIT CANARD À LA PRINCESSE SISSY ⚧️ ⚧️
Être un mec très petit 1 mettre 60 avec une petite carrure a été un handicap majeur dans ma quête de compagnie féminine. Avoir un micro pénis était le clou de mon cercueil. Tout au long de ma jeunesse, j'ai été ignoré ou rejeté par les filles. J'ai eu ma première petite amie à l'unive... Read full Story
Femboy 2021 2023-03-23 796 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial cum in mouth shemale + shemale
50%
Trying It On For Size
I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of eve... Read full Story
shemale lover 2011-10-26 7,799 asshole licking sucking
42%
Chinese Extremes Part 3
It was time to leave Mistress Ming's house and Lien was dressed, or rather tied up, by the two little sissies. First a brutal corset was fitted around Lien's waist, followed by a broad, black leather collar. Lien's hands were then tied in an armbinder, a black leather sack that held Lien's arms behi... Read full Story
shemale lover 2012-01-17 8,502 torture extreme bondage and discipline
50%
The Sweetest Taboo
"Hey sis! Remember me?" Tisha Roberts stood at the door in complete shock looking at the person in front of her, the latest KaySlay CD whispering its aural presence in the background. She scanned the person in front of her, trying to figure out what was going on. The woman in front of h... Read full Story
shemale lover 2011-11-14 5,284 Cumshot cum swallowing handjob
31%
Headmistress' Favorite Sport
When Susanna lost her second job only two days after losing her first; she had no choice but to accept her sister's kind invitation. Susanna had been loath to do so because of two things. Firstly there was pride. Although she had accepted Rachel's offer of help with paying for the children's school,... Read full Story
shemale lover 2011-12-12 6,854 torture toys bondage and discipline
83%
Headmistress' Favorite Sport Part 5
A new part of the first year slaves training was introduced as part of the plan to make them hopelessly addicted to sex. Every evening when they finished class they would be escorted to a room covered in rubber on the inside. The sissies were ordered inside unbound and unescorted, dressed only in th... Read full Story
shemale lover 2011-12-12 6,170 torture toys bondage and discipline chastity belt
50%
Interview with a Fluffer
. "Clarissa", I want to thank you for agreeing to do this interview with me. I think a lot of my readers will be very curious to hear about your experiences in the industry. First of all, can you describe what is involved in your job for me? A. Hi Leah, first of all, no problem, I... Read full Story
shemale lover 2012-01-30 5,330 sucking cum fucking
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,414 Big Tits transsexual big ass
76%
How I became a gurl
So how did you become a gurl? That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock. I actually love the question, because it turns me on to answer it. When I was 15 or 16... Read full Story
shemale lover 2016-01-05 8,018 first time shemales lesbian sex
85%
Jenna & Stephen Part 1
Jenna and I have been friends for nearly 15 years. We dated ever so briefly about 12 years ago, but nothing more than kissing and heavy petting occurred before she decided it wasn't going to work out. At the time I was heart-broken, but looking back now, I realize she was correct that we weren't rig... Read full Story
shemale lover 2011-09-01 4,092 dildo orgasm
75%
Amy Finally Lives Out Her Fantasies Part 2
"Wow! What got into you?" "I don't know, I just decided to finally loosen up and go with my desires," she explained. "Did you enjoy it?" "Are you nuts? I LOVED every second of it!" I exclaimed. Figuring the alcohol played a very large role in her sudd... Read full Story
shemale lover 2011-09-15 3,608 Big Tits ass fucking fishnet
66%
Mistress Jasmine Made Me a Slave
Since long I haven't written a story so maybe I am a little rusty but I hope you enjoy it anyway. There are some autobiographic parts in it but most is fantasy, which part is real and which is fantasy I leave to you. Like any other author I do love comments too, whether they are good or bad. So plea... Read full Story
shemale lover 2011-09-23 9,223 asshole bdsm fingering dominant
100%
Dear Diary
It's now been one year since mother passed away. I still miss her terribly and think of her each day. I also feel ashamed at times when I just wish she were still here to protect me from father and to intervene. His hate for me seems to grow each day and he told me the day I turn eighteen I will be ... Read full Story
shemale lover 2011-11-09 5,112 taboo sentimental erotic