Sort by
Relevancy

Free Stories

100%
Karen, My School Teacher Part 5
The Bus Station By FoxyHosed I looked around, but no one was there. It was dark and pretty cold night outside. I felt the air blowing around and up my pantyhose encased legs and ass. Mmmm nice. I started walking to the bus stop a few blocks further down from the school. I felt very attractive g... Read full Story
FoxyHosed 2021-03-15 7,250 Crossdresser Cumshot Outdoor Masturbation Fetish Blowjob pantyhose legs pantyhose cd
50%
A Shock at the Adult Theatre
I am very often thursdays in the adult theatre, because stylde crossdresser have free entrance at this day. I used to go there by public transportations, because I have no car. In the rear area of the shop we are able to change our clothes and to style up and storing our bags in a locker. About a... Read full Story
SilkeTrav 2020-01-20 8,205 Crossdresser Amateur Outdoor Masturbation Lingerie Homemade
100%
What a sissy crossdresser really craves and fantasizes about
(This is non-fiction) Lots of attention. To be seen and watched. I want the neighbors to see me as I stroll in my yard wearing white vanity fair panties and bra, heels, with a lacy top and a cute bob wig. With my cock raging hard thru the pretty lacy panties, struggling to be free, bouncing around... Read full Story
kelliecdgirl 2024-05-21 3,557 Crossdresser Cumshot Outdoor Masturbation Lingerie sissy femboy
72%
Black Man's White Sissy
I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my ... Read full Story
shemale lover 2012-07-03 9,597 Cumshot oral sex sissy
80%
Owned sissy girl
I met the mature dominant couple that I now call Mummy & Daddy on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for... Read full Story
Andrellina 2015-09-23 29,300 anal ass rimming cd sissy
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 9,701 anal sex submissive sissy cross dresser
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 15,439 first time ass Cumshot suck cd sissy make up
95%
Am I now a genuine Sissy Slut?
I started Crossdressing when I was about 16 years old, the usual story , mother and sisters panties from out of their drawers when I was home alone. As I got older and married I stopped Crossdressing and consentrated on being the family man. As the years rolled by and the kids grew up and left hom... Read full Story
Sissy Kirsty 2023-10-27 13,751 anal sissy stranger
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 14,155 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
50%
LA CRÉATION DE MONICA ⚧️ ⚧️
Je savais. En regardant en arrière maintenant, je me rends compte que j'ai toujours su. Je n'ai jamais rien fait à ce sujet, jusqu'à ce que je sois prêt mentalement, émotionnellement et physiquement. Je suis né Matthew J. Smith au milieu des années 70 en Amérique centrale aux États-Unis. J'ai grandi... Read full Story
Femboy 2021 2023-03-30 1,070 Stockings anal sex Masturbation Fetish Blowjob Big Cock Lingerie Sex Toys feminization cum in mouth poule mouillé poule mouillée et fille poule mouillée poule mouillée
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 34,261 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,563 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
100%
A Shell of A Man
Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty w... Read full Story
shemale lover 2012-06-11 9,600 Cumshot Fetish sissy
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,749 Masturbation Blowjob blonde ass fucking big boobs
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,588 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,617 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
80%
I got humiliated in a catfight
Im a crossdresser and I am very feminine and extremly dainty. I was attracted to a man at a park I went to. He knew I was a crossdresser. I would always say hi when I saw him, but that was it. One day he asked me(on a rainy day as I was getting in my car), do I have a boyfriend am I bi, he wanted to... Read full Story
Kaylamoore994 2023-03-26 6,243 Crossdresser Outdoor Masturbation Fetish Ebony Ladyboy Lingerie humiliation fight sissy crossdresser catfight
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 8,741 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,727 Cumshot Masturbation oral sex
80%
The Grass Ain't Always Greener...
Lawn care takes an unexpected voyeurism and exhibitionism masturbation detour I cut grass, mow lawns, manicure shrubs, trim bushes, and plant trees. Right handed and always trimming from the right side, I've never been a switch hitter when using my hedge trimmer, if you know what I mean. Always ... Read full Story
shemale lover 2013-01-16 5,151 Masturbation Blowjob blonde jerking big boobs
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,615 Big Tits Cumshot Masturbation Uniform Frottage
100%
A Very Hard Working Girl
I jump around a lot when I tell my story. I don't always tell it in the order that it happened. But I do tell my story accurately. It's all me. I write from experience, love to share the dirty little kinky things I do. There is no moral to the story, no ending. I just like to write about the things ... Read full Story
shemale lover 2012-07-17 4,908 Fetish oral sex sissy
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,473 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
50%
Devastating and dominating
Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... Read full Story
shemale lover 2012-01-29 5,234 Masturbation sucking Creampie Latex fucking
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 8,070 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 7,938 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 14,017 Masturbation cum orgasm cumshots prostate
100%
A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
KaceyKlarissa 2024-02-24 5,736 anal Small Tits Crossdresser Group Sex Big Tits Outdoor Big Cock gangbang domination sissy femboy Ass to Mouth cum in mouth
76%
My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
shemale lover 2012-09-09 10,016 Crossdresser Cumshot Masturbation Lingerie heels
100%
How I Became Vanessa Chapter 1
PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husba... Read full Story
shemale lover 2012-10-31 3,938 anal Cumshot Masturbation Sex Toys
100%
Glory Hole Memories
The Glory Hole Fun Begins Locking the car I look towards the building. The entrance is open, but from my position it isn’t possible to see inside, the bright sunshine making the entrance look black. My heels click on the tarmac as I approach, my legs beginning to tremble with fear and excitement.... Read full Story
Sexy Michelle 2024-03-13 4,488 Stockings Crossdresser Outdoor Blowjob Big Cock Lingerie
100%
Boys to girls transformation with a surprise part I
Boys to Girls with surprise For the first time I scheduled an appointment at a studio that will transfer me into a sexy women. I packed my sexiest outfits and high heels and drove to the next city where the studio is. I told everybody I had to go to a business meeting over the weekend. I arrive... Read full Story
TRTRAIN 2024-09-01 1,210 anal Crossdresser Amateur Group Sex Sex Toys Mature Homemade sissy shemale fucks shemale
71%
Joanna 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
shemale lover 2014-06-19 7,165 shemales Masturbation voyeur
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 6,478 blonde shemale submissive cocksucking
80%
The Slippery Slope (Cont. from Beginnings)
As this is a continuation of the story from my last post, i will very quickly just mention the time and event that triggered this downward spiral into my sissyhood. It was in the middle of college, totally moved on from my previous escapades that i brushed off at the time as "experimentation&... Read full Story
DoraTV 2022-12-07 3,554 Stockings transvestite feminization sissy fishnet stockings story Introducing myself
100%
Changling
‘My goodness!’ she exclaimed, ‘It appears that you've had an accident, youngster. You'd better come home with me so that we can make you presentable. It's quite safe, 'cos I live in the big house in the woods on the other side of the hill behind the toilets. Come along, now,’... Read full Story
shemale lover 2012-02-02 8,857 shemales Masturbation Big Cock
80%
Dream Date
Who would have thought it; I was reduced to finding a partner on the Internet? I had read about these dating web sites and though dubious I found one, completed my details and waited. A few days went by and I heard nothing. I waited a few weeks and still I heard nothing. I turned to an old girlfrien... Read full Story
shemale lover 2012-11-14 4,991 Fetish heels
100%
Mike der Pfleger
Mike der Pfleger Vorwort: Es handelt sich hierbei um meine allererste 'Sexgeschichte' die ich schreibe. Meine Schreibkunst befindet sich gelinde gesagt auf Amateurniveau. Die Geschichte ist frei erfunden und entspringt rein aus meinem perversen Gedankengut. Ganz nach dem Motto: 'Geschmäcker si... Read full Story
baileyjay69 2024-08-26 301 anal Crossdresser Amateur Blowjob Big Cock Mature sissy femboy
100%
My Gloryhole Daddy
I had been working the gloryhole at the strip club for almost a month. Mostly it was jerking off pathetic dicks with a fleshlight while fake moaning and scrolling my phone. But every now and then I'd get a text from my favorite john saying he'd be stopping by. His cock was so beautiful! A solid 8 in... Read full Story
KaceyKlarissa 2024-09-11 933 anal Crossdresser Bareback Creampie Blowjob blonde Big Cock domination Guy Fucks Shemale sissy femboy Ass to Mouth
100%
Bike Shed Rendezvous
Chapter 1 A meeting you can't refuse The sun is shining brightly, but the ground is still damp from the morning's rain and the air is very cold. It's lunch time and you quickly walk across the College car park to the sports pavilion. Becky your sweet heart has told you to meet her and she's been ... Read full Story
shemale lover 2012-06-11 3,297 Fetish oral sex crossdressing sissy
100%
Caught by the Past Chapter 2
Previously - After a drink with a new friend he invites you back to his house. Strangely drawn to this handsome guy he persuades you to dress in girls clothes... Now You're wearing a sexy leather mini skirt, fishnets and high heels, your cocks like rock and you're just about to show yourself... A... Read full Story
shemale lover 2012-06-28 2,949 Fetish cum Lingerie oral sex crossdressing heels
72%
First Time Sissy Maid
I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... Read full Story
shemale lover 2012-10-27 17,119 first time Fetish Big Cock domination sissy
100%
Catching up with the biggest cock
I have recently written with an account from my diary about the biggest cock that I’ve ever seen and someone saw the experience and wanted to know more as I had said that I met him a few times. So, I can bring that right up to date now because I have recently been to see him again. But let me go bac... Read full Story
lkusex 2021-06-03 11,042 Masturbation Big Cock Ladyboy domination self sucking Ass to Mouth Vintage
100%
The Interview
The Interview By Sabrina G. Langton *** 'A crossdresser goes on an interview in lots of pink, of course she gets the job' 'Author's note, just a quick little story with some really graphic sex, and a little tiny moral. I hope YOU like it.' *** "Okay, sit, sit, let's get started. S... Read full Story
Brina Giselle 2023-12-04 6,797 anal Crossdresser Blowjob heels cum in mouth pink dress
100%
Sexual fantasies on tiptoes
Sexual Fantasy on tiptoes when I was a teenager, I began to like live female gymnastics and ballet, and I had a good feeling about the posture of women straightening their toes and leaning their heads back, my intuition tells me that this is what happens when a woman has an orgasm, and as an adult I... Read full Story
Oldslut Sissy 2024-04-03 5,165 Crossdresser solo Amateur Masturbation Asian small cock sissy self sucking
100%
Fender Bender Chapter 6
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 Curt had been home form their vacation for almost a week and I hated it. Sure I was glad to see my Mom but with them around I had to revert back to bei... Read full Story
shemale lover 2012-07-26 3,460 Cumshot oral sex cum swallowing sissy
80%
Spankys mother cloths torn off on stage reveal she has cockoc
Erotic website remake of the little Rascals short film remake of Beginners Luck. The audience is laughing hysterically at Spanky attempts to open his stuck helmet. Spankys mother, a blonde beauty peeks out at the audience from the stage wing, as the crowd’s loud laughter, nervously biting her finge... Read full Story
kucksissylicktoman 2020-06-16 5,340 Big Tits Cumshot Masturbation Fetish Blowjob blonde Big Cock gangbang Lingerie Guy Fucks Shemale cum in mouth shemale + shemale
66%
A Series of Perverse Dreams, Part 3
After my last couple dreams, I began to watch a ton of gangbang and bukkake porn. I had jerked to this kinda stuff before but now I was watching it constantly and this time around, it was to the thought of being the girl in the scene. Something about watching a beautiful woman taking numerous cocks ... Read full Story
KaceyKlarissa 2024-03-08 4,877 anal Big Tits Cumshot Creampie Blowjob blonde gangbang big ass sissy Ass to Mouth cum in mouth bimbo bimbofication
100%
A Natural Sissy Part 4
The Next Day I was up early, and called to set up a surgery for Stacy’s breast enhancement. The hormones were working but his tits seemed to have stopped growing at a B cup. I wanted him really top heavy. At least a D cup, maybe a DD. I let the exhausted sissy sleep. As I was finishing u... Read full Story
shemale lover 2012-03-24 4,020 Stockings Fetish cum oral sex sissy
100%
Sissygurl
Sissygurl development A true sissy always wants to always look as sexy and desirable as possible and with a body that looks fabulous in your sexy sissy outfits so you will be super motivated to stay sleek and slim. Now let’s talk make-up. Besides the essential stuff to have in your make-up kit... Read full Story
amberdoll 2020-07-22 2,863 Stockings Small Tits Crossdresser Amateur blonde Lingerie Homemade
80%
Devil with a blue dress
I had the whole day alone and so I decided to get dressed to the nines. After a fragrant bubble bath with body oils I began by painting my nails a pretty pinkish red and putting on my sexy little silver anket. Next my favorite black satin garter belt and a brand new pair of very sheer off-black stoc... Read full Story
shemale lover 2013-07-22 4,794 sex toy Stockings Crossdresser Masturbation cd
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 4,629 sissy cross dresser cuckold
82%
Halloween Double Cross
It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeou... Read full Story
ASSEaster5678 2018-10-29 11,449 Shemale Fucks Guy sissy Halloween
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,675 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
Mein erster Kunde
Mein erster Kunde (Kurzes Intro für die, die meine Sissy Geschichte nicht kennen) Es ist jetzt ca 3 Jahre her das ich meinen ersten Kunden (freier) hatte und es ist noch wie heute in meinem Kopf eingebrannt. Ich war zu diesem Zeitpunkt 21 Jahre jung und habe in meiner Single Wohnung gelebt u... Read full Story
SissyAngelina 2021-09-08 2,222 Crossdresser trans slut sissy femboy Deutsch german hure
100%
Meine ersten Kunden
Mein erster Kunde (Kurzes Intro für die, die meine Sissy Geschichte nicht kennen) Es ist jetzt ca 3 Jahre her das ich meinen ersten Kunden (freier) hatte und es ist noch wie heute in meinem Kopf eingebrannt. Ich war zu diesem Zeitpunkt 21 Jahre jung und habe in meiner Single Wohnung gelebt u... Read full Story
SissyAngelina 2021-09-10 2,281 Crossdresser sissy german