Sort by
Relevancy

Free Stories

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 5,033 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,181 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
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 13,855 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,963 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
91%
Hot Slutty Sissy
Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... Read full Story
Regina10 2020-08-14 6,775 Crossdresser Cumshot Bareback Fetish Blowjob blonde Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Mongoose Hunting and the Dark Car
After my first sexual experience with a trans girl in school (Check out Biology of Music), it was a long time before anything else got me that horny again. Which is obviously understandable given how ridiculous that whole event was. This time instead of a trans girl cumming hot jizz into my mouth af... Read full Story
terrifictim 2023-03-30 5,552 Teen (18+) Cumshot Bareback Creampie Guy Fucks Shemale rimming rimjob Ass to Mouth cum in mouth Surprise secret bathroom sex Daddy daughter risky public
87%
THE ATTIC NOVEMBER 7
THE ATTIC NOVEMBER 7 – PART 1 THE JOURNEY AND GETTING READY. Susan had not had the opportunity to make the journey to the Attic dolled up to the nines so she made do with just wearing her black and pink lingerie under the hideous drab stuff (yuck). Having arrived early and parked up, she relaxed ... Read full Story
sexysusang 2018-03-09 5,922 Amateur Group Sex Bareback Blowjob Guy Fucks Shemale cum in mouth
50%
LE PROGRAMME D'ÉCHANGE SISSY ⚧️ ⚧️
Kristy a travaillé pour Le Matriarcat. Cela semblait plus officiel que ça ne l'était vraiment. Comme si c'était un "Nouvel Ordre Mondial". C'était en fait un club dirigé par des femmes spécialisées dans certains services que les hommes paient grassement. Cela pourrait être appelé prostitution selon ... Read full Story
Femboy 2021 2023-03-25 1,143 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 5,135 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
COMMENT NATHAN EST DEVENU NATALIE ⚧️ ⚧️
Je m'appelle Natalie mais ce n'est pas le nom avec lequel je suis née; c'est plutôt le nom que ma femme m'a donné quand elle a fait de moi sa "sœur" et sa poule mouillée cocu peu de temps après notre mariage. Mon vrai nom est Nathan mais c'est un nom que je préférerais ne plus jamais utiliser parce ... Read full Story
Femboy 2021 2023-04-23 1,600 Teen (18+) Blowjob Lingerie Sex Toys small cock sissy cum in mouth sissify poule mouillée et fille premiere foi
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,093 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
100%
DÉBUTS INNOCENTS
"Avez-vous pris votre vitamine, ma chère ?" Ellen a appelé de la salle de bain. Je me frottai le sommeil des yeux et ramassai le flacon de pilule, roulant un gros comprimé dans ma paume. "Ma pilule de cheval ? Je le fais maintenant." "Avez-vous déjà remarqué une différence ?" "Non. Les vitamines ... Read full Story
Femboy 2021 2023-01-26 1,086 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale
100%
Police House Call
My heart was beating a mile a minute when I heard the knock on my door. I was hoping that it might be Beau, or Larry, or if I’m lucky it would be Tom Cobb. He asked me to call him Tommy. I had been thinking about him recently. Bo and I had banged the night before, but I was as horny as ever. Larry w... Read full Story
Regina10 2024-04-19 3,503 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
100%
Natacha's dungeon,
Natacha's dungeon, For a long time, I have loved wearing lingerie because it always gives me so much excitement to contemplate myself as a woman in front of my mirror. I learned a long time ago to memorize feminine gestures and attitudes while perched on my pumps. I also know how to put on ma... Read full Story
sandratvtg 2024-06-24 1,148 anal Stockings Shemale Fucks Guy Fetish Lingerie domination Sex Toys femboy chastity cage plug urétral
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,598 Big Tits Big Cock shemale + shemale
100%
Reshooting the Scene, Chapter 1
I have been a porn aficionado since I was a teenager. My first dabblings were with Hustler magazine and a *very* hardcore mini-novel called “Her Busted Asshole,” which told the raunchy story of Ginny Cummings’ sexual coming of age. In addition to the very graphic story, it had full color glossy p... Read full Story
Lovelace 2021-06-07 4,518 Bareback threesome Blowjob blonde Big Cock Sex Toys Ass to Mouth
50%
A LA DÉCOUVERTE DE L'AMBRE ⚧️
J'ai toujours aimé la lingerie féminine. De regarder des catalogues à voir des copines le porter, j'ai adoré le look et la sensation de la lingerie sexy et soyeuse, mais pour moi, cela a toujours été plus profond. À 18 ans, j'ai essayé ma première paire de culottes, oh mon Dieu, c'était merveilleux ... Read full Story
Femboy 2021 2023-02-17 1,029 Stockings Crossdresser Cumshot Bareback Fetish Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
100%
Sweet Stephen Wears A Slip.
Stephen is a 'petite' boy, just a little smaller than his Aunt Melanie. Petite figures ran in the family in both the females and males. Stephen cut quite the girlish figure in his Aunt Melanie's pastel-pink full slip. 'Oh, my, don't you look just so simply darling, pretty missy!" Melanie cooed, ad... Read full Story
ALEXEAMES 2024-01-14 5,043 Stockings Crossdresser Amateur blonde Lingerie Shemale and Girl small cock sissy femboy teen (18+)
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 11,467 Bareback cum ass fucking slave
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,462 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
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 33,775 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,324 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
78%
Cara's First Time
Cara's First Time This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in... Read full Story
Emma W 2017-07-05 30,068 Crossdresser Amateur Bareback
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 9,888 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,862 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
88%
Who's She?
School had been a bore for Tony. He was a bright lad and didn't have to work too hard to get through classes unnoticed by the teachers and class mates. He had plenty of friends but no one close. He didn't excel in sports or academically. He had picked up a few good exam results but had decided that ... Read full Story
Vinny_A 2019-07-08 11,662 Teen (18+) Crossdresser Amateur Big Tits Bareback Blowjob Lingerie
100%
Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 4,040 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
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 7,602 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
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 3,606 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
My Noisy Upstairs Neighbors Part 3: Making Porn
In Part 2, I recounted how Paul, my commanding upstairs neighbor, coerced me into making porn with him and his younger roommate. Now, I'm excited to share the first video we created together. At 12:45 PM on Saturday, I nervously approached Paul's door. After knocking, Paul opened it with a smile ... Read full Story
Chrissy Tunnell 2024-07-16 673 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
100%
The game show,
One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... Read full Story
chris1989r 2022-01-24 4,692 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,078 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in mouth
87%
Southern Hospitality Ch. 03
XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... Read full Story
Gwapo67 2022-05-16 4,767 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,845 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
College project surprise
So this story happened while I was still in college and remains without doubt, the craziest, most exciting experience of my life. So I the story begins one day when I walking to class. I went to a big university so my walk was quite long, and the first 1/3 was just through off our campus housin... Read full Story
Jsmithsub 2020-09-16 21,007 Group Sex Bareback Shemale Fucks Guy Fetish threesome Big Cock Ebony domination Ass to Mouth cum in mouth
92%
Caught Before My Brother and Friends Could Use Me.
Caught Before My Brother and Friends Could Use Me. By TVTrinity As a boy, I was fascinated by the petite little girl I saw in the mirror when crossdressed. When I got caught dressing by my uncle. I experienced the effect it had on men firsthand. He looked at me the way a man looks at a girl. I... Read full Story
Tvtrinity 2021-04-07 5,750 Teen (18+) Crossdresser Amateur Bareback shemale Guy Fucks Shemale sissy forced young faggot Trinity uncle Richie Budd
50%
L'INVESTISSEMENT SISSY ⚧️ ⚧️
La fin d'une autre longue journée. Près de 19h00 et Colin Spencer travaillait toujours dans son box, presque terminé avec le dernier des papiers que l'un des associés principaux de la société d'investissement dans laquelle il avait effectué un stage depuis près d'un an maintenant l&#... Read full Story
Femboy 2021 2023-03-21 837 Stockings Lingerie domination Guy Fucks Shemale Interracial Sex Toys cum in mouth
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,453 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
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 31,335 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
96%
A Night of Lust
I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... Read full Story
JessicaEdwards 2018-08-07 18,235 Stockings Amateur Cumshot Masturbation Bareback Creampie Shemale Fucks Guy Blowjob blonde Big Cock Lingerie deepthroating Guy Fucks Shemale cum swallowing deep throat deep penetration cum swapping pov Ass to Mouth cum in mouth anal fuck sloppy virgin ass
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 3,963 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
100%
The Game 2
That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... Read full Story
chris1989r 2022-01-24 4,416 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
100%
Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
shemale lover 2012-05-29 5,062 Cumshot orgasm condom sex
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 30,934 strapon porn
66%
Would You
'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her sk... Read full Story
shemale lover 2012-09-23 6,555 sucking cum massage
100%
THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
shemale lover 2012-01-28 4,041 licking sucking fucking Sex Toys
50%
A Married Marilyn
"Class is dismissed. Don't forget the project due…" "Huh, what?" Marilyn woke up disoriented from her nap. When she finally came to, she vaguely remembered some project for Intro to Computer Science, gathered her legs from the chairs in front of her, dusted off her b... Read full Story
shemale lover 2012-03-18 7,163 Group Sex Masturbation sucking Sex Toys
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,496 Crossdresser hardcore ass fucking cd
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,000 big dick anal sex suck Blowjob cock sucking workplace
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,908 Stockings Big Tits fucking foot fetish