Sort by
Relevancy

Free Stories

100%
I met a guy in the nightclub and I didn't tell him I was Trans
I’d worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
Madison Heights 2023-03-25 6,604 Cumshot Outdoor Blowjob Big Cock cum in mouth club outfit Surprise Cock Partying surprised
100%
LES ÂMES PERDUES ⚧️ ⚧️
Le lycée est un endroit compliqué avec différents groupes de personnes qui luttent pour trouver leur chemin dans le monde. Qu'il s'agisse d'étudiants de première année qui viennent d'emménager dans un nouvel endroit inconnu et effrayant, ou de seniors qui sont maintenant de jeunes ad... Read full Story
Femboy 2021 2023-03-21 848 Fetish Blowjob Big Cock cum in mouth shemale + shemale emo
100%
CONTES DE FEMMES TRANS TOPS ⚧️ ⚧️
Être coincé au bureau tard un vendredi, c'est toujours nul. Alors que je remarquais que des subordonnés et des collègues quittaient le bâtiment alors que l'horloge sonnait cinq heures, certains d'entre eux s'arrêtant à la porte de mon bureau pour me souhaiter poliment un bon week-end... Read full Story
Femboy 2021 2023-03-19 851 Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth transexuelle
50%
MON NOUVEL ENTRAÎNEUR ⚧️ ⚧️
« Alors, tu as besoin d'une place ? elle a demandé. Des mèches de cheveux roux, qui étaient tombés de sa queue de cheval, encadraient son visage alors qu'elle me regardait. "Hummm bien sûr," mentis-je. L'équipement de la station de développé couché où je m'entraînais était conçu pour être utilisé... Read full Story
Femboy 2021 2023-02-21 728 Crossdresser Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth
50%
Comment sissy apprend à aimer le goût du sperme
La plupart des poules mouillées veulent entretenir une bite et apprendre à la prendre dans leur précieuse petite chatte de poule mouillée. Ils ont aussi besoin de goûter, voire de manger, le sperme. Bien sûr, comme toute autre chose dans la vie, cela nécessite une formation. Manger du sperme conc... Read full Story
Femboy 2021 2023-01-12 620 Crossdresser Amateur Cumshot Creampie Fetish Blowjob Big Cock cum in mouth
92%
Caught in the act...
One summer, my cousin Nancy came to stay with us for a while, as her parents had gone away on a cruise trip. At 18 years old, she was a couple of years older than me and in the full bloom of her young womanhood, so to speak. She knew it, too, and it was obvious that she had no problem at all in pull... Read full Story
caroletv31 2018-04-23 18,864 Stockings Fetish Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
50%
Larissa blond blown in Frankfurt
Very friendly already on the phone. She was very chatty. Asked when I wanted to come and I said at 12:00. I meant if she squirts and she answered yes, but costs 50 € extra. She then said that at 12:00 maybe her landlord will come, the bed would be broken. If he hadn't been there by then, we would ha... Read full Story
Bigpruegel69 2023-12-17 5,088 Cumshot Masturbation Creampie Blowjob 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 4,954 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
80%
Three In A Day
Clara felf especially slutty today. She briefly gazed at her long legs shimmered in the smooth, silky black stockings, and black patent leather pumps as she pressed the gas pedal of her car. Her olive skin and black wig were set off by the brightest shade of red lipstick she could find. Driving d... Read full Story
iluvgurls 2018-11-12 4,528 Small Tits Crossdresser Group Sex Cumshot Blowjob cum in mouth
100%
mushrooms in all shapes and forms
Mushroom season is open! Yummy! I love mushrooms, in all shapes and forms. We were about fifteen mushroom lovers who only get together to pick mushrooms, without any other friendly gatherings! For this last outing of the season, our splendid instructor was accompanied by her cousin, who was sup... Read full Story
hippocampus_171 2023-11-24 6,414 Small Tits Amateur Cumshot Mature small cock big ass bisexual cum in mouth bald men glabrous
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 4,981 anal sex sucking Big Cock cum
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 5,759 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
100%
UN RENDEZ-VOUS ROMANTIQUE ⚧️⚧️⚧️
Alex mordilla sa lèvre en fixant le test d'anatomie devant lui. Après une semaine épuisante de finales et de sessions d'étude nocturnes, c'était enfin son dernier test. La liberté était si proche qu'il pouvait presque y goûter. Sa jambe rebondit anxieusement alors qu'il remplissait une autre série d... Read full Story
Femboy 2021 2023-02-17 982 Big Tits Cumshot Fetish Blowjob Big Cock Guy Fucks Shemale Futanari cum in mouth
50%
DANS LES CHAÎNES ⚧️ ⚧️
Certains pensent qu'une lune rouge n'est que le reflet du soleil provoquant la teinte rouge rouille et étrange. Alors que d'autres croient en une signification plus spirituelle derrière la couleur de la roche lunaire éclairant notre ciel nocturne. Ce soir, s'il y avait un moment p... Read full Story
Femboy 2021 2023-03-18 682 Stockings Crossdresser Fetish domination Futanari cum in mouth
50%
MA MAÎTRESSE MIRACLE
Sam tapota nerveusement ses doigts contre le verre à moitié plein. En règle générale, vous êtes censé boire un coup avec une gorgée, mais sa tolérance à l'alcool n'était pas exactement la meilleure et le bourbon dans la tasse servait vraiment plus de courage liquide à ce stade. Cela faisait ... Read full Story
Femboy 2021 2023-02-05 1,083 Stockings domination Sex Toys Futanari Ass to Mouth cum in mouth shemale + shemale
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,208 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
100%
Chinese Apple Turnover
I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax f... Read full Story
ASSEaster5678 2019-01-09 6,507 anal sex Shemale Fucks Guy Asian Guy Fucks Shemale
50%
FAIRE GRAND ⚧️ ⚧️
Mon nom est Tim. Je suis un homme blanc de 23 ans. Il y a environ 6 mois, j'ai déménagé à Los Angeles pour essayer de devenir acteur, mais comme vous vous en doutez, je n'ai pas eu beaucoup de chance dans ce département. C'était début novembre, quand je suis allé dans le bureau de mon... Read full Story
Femboy 2021 2023-03-20 754 Stockings Crossdresser Fetish Lingerie Interracial cum in mouth
100%
The 10 in Bay 10
On the USS Corinth, there were 10 bays - the first bay was for the captains and their personnel, the second bay for first class, the third bay for business, and so on. The back bays were reserved for the ship’s workers. All the way back in bay 10 was the engineering bay. Those in bay 10 rarely inter... Read full Story
sevon 2022-10-03 4,698 Cumshot Bareback Big Cock Futanari shemale + shemale
100%
A Secret Fetish Chapter 1
When teaching a section of my favorite class, "Modern Erotic Literature", I noticed a guy in the back of the room acting strangely. He was in obvious discomfort, and I wondered why. It was during the lecture where I discuss fetish stories. Students find it a revelation. The first thi... Read full Story
shemale lover 2012-06-11 4,648 Crossdresser Fetish Blowjob
80%
In The Club Part 3
Continuing story from part 2 , i am on the bed in the motel bedroom looking over my shoulder with my tongue out watching deans 10 inch dick slowly disappearing up my bottom , after its half way up it meets resistance , i am wet but clamped up , as he pushes harder i relax and his gorgeous hard kno... Read full Story
sara gabo 2020-09-21 2,205 Bareback Fetish Big Cock sissy slut Club Girl
100%
Hose and Heels in the Bedroom
Liza giggled as she sat back down on the sofa, a mischeivous smile on her face. "Whats so funny I asked?" wondering what had tickled her fancy. After all the only thing that had happened was that she'd just been to the toilet to relieve the pressure that the 3 or 4 glasses of wine tha... Read full Story
shemale lover 2012-05-15 3,891 anal sex Cumshot Fetish fingering pantyhose heels
66%
An Evening's Pleasure in Plastic Panties
Dear RubberPanties I have enjoyed wearing plastic panties for many years now. Although I don't have any at all the moment, I'll be ordering three pairs next week as a little Christmas present to myself. After the ones I'd had for a several years began to fall apart, the replacements I bought were... Read full Story
shemale lover 2011-12-22 5,312 shemales Masturbation Fetish
85%
MISS LORI & MISS MICHELLE, SISSY SISTERS IN SIN
Super Queens Michelle & Lori MISS LORI & MISS MICHELLE, SISSY SISTERS IN SIN'; A TALE OF LESBIAN SISSY LUST AND LOVE "Let's go get some cock, Baby" said Michelle, all painted and dressed as an absolutely flaming drag queen; she flipped up her short miniskirt as she... Read full Story
MissDeeLiscios 2015-04-15 4,940 Big Cock ass fucking cock sucking cd jacking off sissy
100%
Big cock heaven.
I live in Vancouver and saw a beautiful trans escort online and couldn’t resist setting up a meeting. I met her at a hotel and she was just as beautiful in person as online. She was Asian and had the most wonderful big tits and ass. Her cock was a solid 8 inches, uncut with a big mushroom head, whic... Read full Story
Eyecandy64 2024-02-06 6,169 anal Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Asian
100%
Hose and Heels in School - I'm a bad girl
A knock on the door? Who could that be? After all it was mid-evening on a Friday night and I certainly wasn't expecting anyone. I was looking forward to a night of relaxing on the sofa and nothing more. I opened the door and there stood Liza, staring at me with a smile on her face. "U... Read full Story
shemale lover 2012-05-11 3,070 anal sex fingering spanking crossdressing
82%
MISS LORI & MISS MICHELLE, SISTERS IN SIN
MISS LORI & MISS MICHELLE, SISSY SISTERS IN SIN Super Queens Michelle & Lori MISS LORI & MISS MICHELLE, SISSY SISTERS IN SIN'; A TALE OF LESBIAN SISSY LUST AND LOVE "Let's go get some cock, Baby" said Michelle, all painted and dressed as an absolutely flaming d... Read full Story
MissDee 2015-12-15 4,643 big dick ass cum cock sucking sissy deep fucking
57%
How Nina's fuckhole was broken in.
I wrote this story a while ago and saved it. It isnt tranny related at all, it is just a short story about when i lost my anal virginity. If it isnt very relevant to this site, tell me, and ill remove it. It is entitled 'Giving my anal cherry away'. I am no stranger to gay sex. I have sucked a he... Read full Story
NinaSissyGurl 2016-08-29 4,583 Big Cock gay Used First anal
100%
Lady In The House Ch. 02
A story by Michele Nylons, Part II "She's all yours Eddie. She looks beautiful." I heard Carmel say as 'she' disappeared down the corridor, her high heels clicking on the tiled floor. Eddie appeared at the door to the cell, he stepped inside and closed the door behind him. "So what do yo... Read full Story
✘Transensual✘ 2019-01-11 4,729 Stockings Crossdresser Fetish Big Cock Uniform Lingerie domination PRISON PUNK prison sex Prisonboycum Prison Bitch
100%
My First and Last Girlfriend Part 3
I was lying completely naked on the bed, with my dick in a semi erect position, and she was next to me, playing with my hairless balls, and sliding from time to time her middle finger under them caressing all the way to my ass and then right back. I kept my eyes closed, and enjoyed every secon... Read full Story
shemale lover 2011-09-28 3,791 asshole Big Cock cum swallowing
100%
A Job in the Theatre Chapter 3
The following morning Paula woke early and picked out the clothes he would wear. Still influenced by the sexy baby doll that had kept him hard throughout the night, he decided on something sexy, at least underneath. He selected a cute see-through bra and panty set in black with red roses. He checked... Read full Story
shemale lover 2012-03-12 2,622 Fetish cum crossdressing
100%
Woman Cross Dresses for Power & Sex
Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, ev... Read full Story
shemale lover 2012-10-09 3,924 sucking Fetish fingering crossdressing
86%
Cindy and Juanita Kinky Shemales
Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones beca... Read full Story
darrell 2016-11-30 11,088 anal Big Cock deep throat swallowing foot fetish piercing
90%
Liberty in Lisbon Part 1
My wife and I started to plan early retirement. We planned to take trips and live in various parts of the world for a few months here and there. Of course enjoy the grand kids more. Then my world changed. All plans out the window. I was suddenly by myself. The thing I wanted to get away from most, m... Read full Story
Rusty12 2019-06-28 8,005 Amateur Big Tits Cumshot Masturbation Blowjob Big Cock Frottage
100%
A new start in life
“In life, finding a voice is speaking and living the truth. Each of you is an original. Each of you has a distinctive voice. When you find it, your story will be told. You will be heard.” John, living outside Boston, being your average accountant working with Gillette, had gone through a messy di... Read full Story
Jon Paul 2024-05-09 2,493 anal Amateur Shemale Fucks Guy Big Cock Guy Fucks Shemale small cock big ass
100%
Fetish party with a twist
The smell of rubber and latex and the combination of the strobe lighting was overpowering, the techno sound of the club just added to the already intoxicated atmosphere of the place. The club was a frenzy of half naked, latexed, rubberised bodies covered in sweat dancing to the frenzied sound of tec... Read full Story
shemale lover 2011-09-22 4,240 anal sex Group Sex cum Latex
100%
A Job in the Theatre Chapter 18
"You are not going to believe this," Andrew said. He managed one of Ted's businesses down by the beach. He was one of the few employees who were aware of Ted's special interests. "Believe what?" Ted asked taking the bait. "A new guy started working out over there about... Read full Story
shemale lover 2012-03-15 3,258 gay male huge cock stroking
80%
Fetish party with a twist
The smell of rubber and latex and the combination of the strobe lighting was overpowering, the techno sound of the club just added to the already intoxicated atmosphere of the place. The club was a frenzy of half naked, latexed, rubberised bodies covered in sweat dancing to the frenzied sound of tec... Read full Story
shemale lover 2012-04-22 2,361 anal sex oral sex handjob
100%
A Tale of Cum and Passion
It was an anonymous meeting, set up through a popular Internet site. The profile specified I was looking for a transsexual or a transgender woman with nice legs and feet. Basically I was looking for a chick with a cock to satisfy my fetishes for legs, stockings, feet, cock, and cum. Victoria walk... Read full Story
shemale lover 2012-07-06 4,045 anal sex Cumshot shemale oral sex
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 4,827 anal hardcore Creampie Fetish oral fingering
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,591 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,659 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
A Job in the Theatre Chapter 16
"Ted has invited me to his poker game" Paula let slip. "Oh really? Now that sounds interesting" Sarah said. "It will be if we come up with the right uniform. It's all boys so I am going to dress in some sort of domestic help type uniform. But of course it has to be the... Read full Story
shemale lover 2012-03-15 3,193 shemales anal sex Big Cock
64%
Caught in Panties & Dominated
I love to wear sissy clothes, and I fantasize about being controlled by a dominating mistress, who forces me to wear her clothes, to take her boyfriend's cock into my virgin mouth, make love to his big stiff cock, deep throating it until he comes into my mouth, filling up my mouth until his hot cum ... Read full Story
shemale lover 2012-10-15 6,277 Fetish oral domination Sex Toys sissy
100%
First fuck in public ;)
You’re only wearing a coat, I find a place where, I can kiss you then slide my hand between the flaps of your coat. I expose your breasts and slide my hand down across your tummy down to your pussy. My fingers start to explore your soft bush, working there way to your soft pink lips surrounding your... Read full Story
BalkanLoco91Ri 2019-08-26 3,779 Stockings Teen (18+) Amateur Big Tits Cumshot Outdoor Masturbation Bareback Creampie Blowjob Big Cock Uniform domination Homemade pov cum in mouth
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 9,935 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
67%
Librarian with a Cock
I would go to the library on Tuesday's mainly because I was attracted to the librarian. I never really slept with women but for some reason she really turned me on. I guess it was her age, but I love older men and women (sometimes.) A few weeks ago I struck up a conversation and found out her name w... Read full Story
shemale lover 2015-01-21 8,000 ass suck Big Cock
55%
Teach me to love cock
I woke up from my soft bed and started watching tv then the door bell rang and it was the mail women she was black and she had big lips big huge tits a big nice round ass and a thin body she want to welcome me to the naberhood she also had sexy long green and red hairshe gave me her number and said ... Read full Story
shemale lover 2011-12-28 3,969 anal shemales hardcore
100%
Becoming a Cock Worshipper
I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes. I especially enjoyed watching a girl choke and gag and... Read full Story
shemale lover 2012-02-29 3,787 Fetish crossdressing
50%
The Ultimate Cock Ball Torture
I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... Read full Story
shemale lover 2012-04-29 3,549 anal sex oral sex
100%
A Year in the Life of... Chapter 6
Mistress Danni led him down a short flight of steps into the cellar and he reflected on the day he had had as he followed her, his nerves jangling, apprehensive about what was to come. He had slept quite well last night though a couple of times he had rolled onto his back and had been woken suddenly... Read full Story
shemale lover 2012-08-01 2,850 Fetish domination oral sex
91%
My first big cock
So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective. I tried an online dating site ... Read full Story
Cbosh40s 2015-03-31 10,439 anal Crossdresser hardcore Mature sissy
93%
Nancy finds out...
Nancy’s stay with us that summer was going to prove even more eventful than ever I could have imagined. Even after having been caught wearing her things by the neighbour’s son, Lesley, which led to a whole new dimension in our friendship, as you’ll know if you’ve read “Caught in the Act…” Once ag... Read full Story
caroletv31 2018-04-23 8,564 Stockings Fetish Ladyboy Lingerie Shemale and Girl high heels cum in mouth
95%
My First Time
I used to be a normal straight guy, or at least, so I thought. That was until I began exploring trans porn, I was so turned on by it, but thought it was wrong, I tried to fight it, but soon enough trans porn became the only porn I could get off to. I didn't know what to do with this obsession, ... Read full Story
handsome man 2018-06-07 21,884 Crossdresser Amateur Shemale Fucks Guy Sex Toys Homemade cum in mouth
92%
My wife Gwen
My wife, what can I say she is tall and leggy with thick, natural wavy orange-red hair with beautiful porceline skin and just enough freckles to tell you she is a true ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen. From the time we... Read full Story
Zöe from Kingston 2019-01-08 7,579 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
84%
First Time: How I Love Cock
The first time I ever sucked a dick was when I was around 12 years old. I was at a sleep over with a friend. We were camped out in his backyard in a tent and he started things out tentatively by asking about my luck with the ladies, which was non-existent. Then he suggested that since neither of us ... Read full Story
wickeddogg 2019-12-11 33,664 Teen (18+) Cumshot Bareback Blowjob cum in mouth