Sort by
Relevancy

Free Stories

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 3,617 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Shawshank affair
Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... Read full Story
Jon Paul 2018-08-20 6,604 Stockings Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
The reason why I became a crossdresser
At first, I was just a straight and ordinary boy who was into sexy lingerie, stockings and heels. But one day, I suddenly thought that I wanted to try on my mom's panties, stockings, and high heels. So I did it. It was so excited and I started to get addicted to cross-dressing. Before dres... Read full Story
cdmisato 2024-02-28 6,519 Crossdresser Asian Ladyboy sissy
50%
Being Shemale
Every night I wear make up and dress up in a sexy lingerie. I stand in my balcony late night trying to lure men and women driving on the road. Last night a truck driver stopped near my house to inspect his vehicle. During his inspection he suddenly saw a long legged booty women in the balcony inf... Read full Story
babydriver 2024-06-04 2,431 Stockings Crossdresser solo Outdoor Ebony Asian Ladyboy Lingerie big ass sissy femboy
100%
Part 2..My First time (Cont).
Part 2. I remember asking Andy if being made love to would hurt me, (note I said made love to and not being fucked) and he said it would hurt the first time but after that it should be ok so I asked him to make love to me. He asked me what position I would like and I replied I had no idea as this w... Read full Story
Nicole-Andrea 2022-10-05 4,308 Crossdresser Amateur Bareback Lingerie
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,535 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,082 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
Chrissy Tunnell 2022-12-01 3,644 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 1,043 Stockings Crossdresser Cumshot Bareback Fetish Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
50%
FONDANT À LA VANILLE ⚧️ ⚧️
Je vois ma cible assise au bar, en quelque sorte à la limite d'un des groupes de commerciaux. Il prend une bière mais il ne boit pas aussi vite que les autres et il regarde nerveusement autour de lui de temps en temps. J'ai une préférence pour l'homme plus légèrement construit. Il doit être plus ... Read full Story
Femboy 2021 2023-02-21 770 Stockings Crossdresser Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination 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 9,103 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
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 2024-07-16 852 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
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 31,364 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
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 6,784 Crossdresser Cumshot Bareback Fetish Blowjob blonde Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,042 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
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 5,058 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,640 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
60%
Shemale Chrissy Fucked by a Demon
I wanted to write this the night it happened, Halloween, but I was still so traumatized. I was at my fictional fantasy Sugar Daddy's house alone and already spooked out by the noises of this old hundred-year-old wooden house in this loud thunder storm on what some call "Devil's Night." I had to turn... Read full Story
Chrissy Tunnell 2022-12-01 4,092 Small Tits Crossdresser Amateur Bareback Fetish Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,606 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
89%
The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
Tvtrinity 2021-04-07 21,678 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,648 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
84%
Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
Zöe from Kingston 2018-08-09 9,201 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature 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 5,983 Crossdresser Outdoor Masturbation Fetish Ebony Ladyboy Lingerie humiliation fight sissy crossdresser catfight
50%
a diary piece - my next date
A diary piece - my next date I hadn't forgotten how to please a man and I had decided to be a little whore for him. Yes I enjoyed it very much and wanted to be fucked again the next day. When I start having sex I want it all the time. HiltonP had said he wanted a date again on 21st and 28th ... Read full Story
amberdoll 2020-09-16 2,657 Stockings Small Tits Crossdresser Amateur Bareback blonde Lingerie Homemade
69%
Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
Stud4Shemale 2017-05-22 7,442 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
100%
Lady In The House Ch. 03
A story by MicheleNylons ( Michele continues to be used by the inmates of a prison. Hot wet fluid suddenly soaked the tops of my thighs and the crotch of my panties. I felt stream after stream of his creamy seed shoot against my silken hosed thighs and being to slowly run down my legs. My crot... Read full Story
✘Transensual✘ 2019-01-11 6,373 Stockings Crossdresser Bareback Creampie Fetish Blowjob Big Cock Lingerie domination Guy Fucks Shemale PRISON PRISON PUNK prison sex Prison Bitch
100%
Highway in Heels
Highway in Heels By Sabrina G. Langton *Stories from the real world 1 This story is autobiographical. When I was 20 years old I used to drive a van for my parents from Brooklyn to Tarrytown New York once a week to drop off merchandise for retail shops in the area. I always had a full van on ... Read full Story
Brina Giselle 2023-08-28 4,685 Crossdresser blonde pantyhose kissing transgender
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,747 Crossdresser Cumshot Masturbation Lingerie heels
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 30,084 Crossdresser Amateur Bareback
100%
Towel Boi: Agreement Signed
Ralph moved the mouse to wake up the computer. He navigated to his legal docs account and downloaded a generic pre-existing relationship agreement. He asked for the spelling of the new hire’s first and last name. “First name K-A-S-E-Y. Last name S-T-E-V-E-N-S.” “Got it,” acknowledged the owner. ... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,899 Crossdresser Bareback Creampie Blowjob Guy Fucks Shemale Interracial small cock big ass sissy femboy
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 5,073 Stockings Crossdresser Amateur blonde Lingerie Shemale and Girl small cock sissy femboy teen (18+)
83%
Abducted and Turned Out Chapter 1
About four years ago, I decided to go out for the evening to a local club that tgurls hung out at. I was a regular there, and had been going there for some time with a regular circle of TG/CD girlfriends that I hang out with. I was already excited when I started to prepare myself in the late afte... Read full Story
shemale lover 2012-08-10 5,218 Crossdresser blonde oral sex cum swallowing
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,613 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,372 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
Kelly's first cock
I've been dressing on an off for as far as i can remember, starting when i was at school, coming home early and putting on my mum's lingerie and heels and wanking myself off looking at my reflection in the mirror. However, it wasn't until i went to uni that i started to get into tranny porn, where i... Read full Story
kelly louisa 2012-10-16 4,653 first time Crossdresser Blowjob slut sissy
93%
Me and Sabrina
This story is fictional. I was just another normal kid. I'm just small and effeminate. My name is Nick. Im 13 years old. I have always enjoyed dressing in woman's clothing. I have a friend her name is Sabrina. Shes a very hot girl. I thinks she 5'5,110 lbs and 36c. Compared to me I'm 5'4 and 10... Read full Story
shemale lover 2013-07-16 2,911 Crossdresser anal sex Cumshot Lingerie cd