Sort by
Relevancy

Free Stories

50%
Embarrassé par ma mère
Oh mon Dieu! Je ne peux pas croire ce qui vient de se passer. J'étais tout habillé avec mes sous-vêtements sexy, bas noirs, porte-jarretelles, string en dentelle et talons quand j'ai vu ma mère et mon père se garer dehors dans la voiture. J'ai paniqué et j'ai enlevé mes talons très rapidement et j'a... Read full Story
Femboy 2021 2023-01-27 948 Stockings Teen (18+) Crossdresser Fetish Lingerie Shemale and Girl domination
50%
Le trou de gloire Futanari
Alors que je pousse mon déjeuner scolaire avec une fourchette en plastique, je ne peux m'empêcher de laisser mon esprit vagabonder. J'ai envisagé de faire quelque chose... Quelque chose que je ne devrais probablement pas. Mes amis m'ont parlé de cet endroit, un dans un vieux bâtiment aba... Read full Story
Femboy 2021 2023-02-06 1,467 Teen (18+) Cumshot Shemale Fucks Guy domination Futanari cum in mouth
100%
EXPULSÉ ⚧️ ⚧️
Quand mon père est parti dans un accès de colère, ma mère s'en est pris à moi. Elle a ensuite rebondi d'une relation malheureuse à une relation plus malheureuse en me blâmant toujours pour son incapacité à garder un homme. La plupart des hommes étaient des creeps et même moi je savais qu'... Read full Story
Femboy 2021 2023-03-24 1,026 Teen (18+) domination Guy Fucks Shemale cum in mouth humiliations cage chastity feminisation forcé
50%
ADAM PERD UN PARI ⚧️ ⚧️
La dernière feuille d'automne est tombée au sol alors que j'emballais le dernier de mes livres dans une boîte en carton. Je n'en ai jamais lu aucun, mais ma mère était catégorique pour que je garde chacun d'eux. En raison de problèmes financiers, notre emballage et notre déménagement ont été retardé... Read full Story
Femboy 2021 2023-04-15 1,754 Teen (18+) Blowjob Lingerie Sex Toys humiliation sissy sissification feminisation forcé forcé anal
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 8,266 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
100%
My First Blowjob
Fuck! I'm so jealous! Back in my teens I could self suck! I'd lock myself in the bathroom, lay on my back and bring my legs over top. I was able to not only get the head of my.cock in my mouth, but half of my length as well. The first time I nutted in my own mouth, I wasn't prepared for the big lo... Read full Story
Hardrock51Fifty 2024-03-26 4,908 solo Cumshot Blowjob self sucking cum in mouth teen (18+)
100%
Sex With Not Just 1, But 3 Females
When I was 18 years old, I was still occasionally going to the Highbridge toilets in Lincoln on a Saturday and getting paid for having sex with guys be it sucking cocks or being sucked off, dirty chats, wanking them off or giving or taking anally. I never turned down any form of payment, money or... Read full Story
Linda Tiffany Vista 2024-05-07 2,685 Stockings Crossdresser Amateur Lingerie cum in mouth teen (18+)
50%
The first requirement of a deal with Dominatrix Persephone.e
There was a number of requirements before I even consider'd fucking that sissy ass, firstly, I expected dedication to be shown and to prove that the sissy could obey my orders, after a trial period, then I consider to force my big dick down the throat of the that sissy, and then fuck brutally and ex... Read full Story
Dominatrix Persephone 2024-06-21 3,353 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
100%
My first made me a femboy (2/3)
I'm sure it was something that was going to turn me on before it started but the first man I was ever with had his own desires for me. I had no idea all the places it would go but I loved all of it. My best friend moved into an apartment building in a quieter side of the city we grew up in. She h... Read full Story
boytoypdx16 2024-07-03 3,455 femboy teen (18+)
100%
My first made me a femboy (3/3)
I could tell he was turned on and after turning my attention back to myself I knew I liked how I felt too. I adjusted the panties around my hips and ass until they laid flat and smooth against my body, they fit me perfectly. I asked him if liked they way the looked, but I knew without him saying ... Read full Story
boytoypdx16 2024-07-08 3,256 femboy teen (18+)
86%
Miko and Mali; Thailand's finest teen sisters
Last August my friends and I went on a “lads holiday” to the beautiful country of Thailand. We had booked a fortnight, which was to consist of five nights in a city hotel in Bangkok, and the remainder in a stunning 5* resort in Phuket. It was my first time in the country, my friends hav... Read full Story
shemale lover 2014-06-25 8,552 shemales taboo lesbian sex
75%
The teenage slut
Hey folks Sandy here once again. I know every time you see me I go up one grade level but this is one tale I felt I should tell you. Let me start at the beginning after me and Bella fucked each other. Well were still together. Laughing, eating together, just having fun basically. We still fuck in th... Read full Story
shemale lover 2012-04-25 4,044 Teen (18+) Cumshot oral sex cum swallowing
100%
Fender Bender Chapter 2
The bright sun shining through the window woke me up, for a moment I was confused and disoriented. Then it all came back to me. I had sex with Mark and Susan James last night and I was still wearing a pink baby doll nighty and matching panties she had given me to put on before we went to bed. I w... Read full Story
shemale lover 2012-07-26 4,691 Teen (18+) Fetish crossdressing
100%
After Church
I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they were... Read full Story
shemale lover 2012-08-19 6,405 Teen (18+) Fetish oral sex crossdressing
90%
Brian Becomes Brittney Chapter 1
My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before colle... Read full Story
shemale lover 2012-12-21 5,586 Teen (18+) Crossdresser domination Sex Toys ts
100%
Pretty Woman
Tyler was as nervous as anyone could be. Hazel eyes darted for the door as silky black stockings slid up smooth white legs to meet garter straps attached near lacy white panties. Next came the bra, straps catching on skin slightly sticky with perspiration. Heart pounding as the black pencil skirt gl... Read full Story
shemale lover 2012-12-22 9,185 Stockings Teen (18+) Crossdresser sucking heels
100%
Tina and Dani
I had not cross dressed in months, but I was having an insatiable desire to suck some cock. I decided to go to a local Phoenix gay club in search of a fun sexy date. After a few "apple-tinis" I was approached by a cute guy, in his thirties, shorter than me and well built. He introduced him... Read full Story
shemale lover 2013-01-10 4,439 Teen (18+) Crossdresser sucking ass fucking cd
93%
New School, New Life
Part of my father's job is on-campus recruiting, so when it was time for him to spend a week at the university where I was enrolled for the following fall, we decided that I should go with him and familiarize myself with the campus. We left on a Friday morning to ensure I'd have a full week on ca... Read full Story
shemale lover 2013-02-06 9,146 Teen (18+) Crossdresser Cumshot sucking ass fucking
100%
Mommy Writes for Mandy
We work in a big corporate office. I am the owner of the advertisement company and you are my secretary. You are fully Mandy. You started taking hormones years ago to fully become a girl. Your hair is grown long and you have little a cup breasts and chose to always wear dresses, skirts, frilly blous... Read full Story
shemale lover 2013-03-12 4,949 Teen (18+) Crossdresser Cumshot Lingerie ass fingering
100%
After Gym Class Chapter 01
I was tired. It was the last period of the day, so at least the day would be over soon. I didn't sleep very well last night, still thinking about that jerk Josh and what he had said. "I really want someone who is more open to doing different things sexually," he had said. What the fuc... Read full Story
alwaysupforu2004 2014-09-17 7,112 Teen (18+) Cumshot suck shemale stroking
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 20,263 first time suck fingering Lingerie ass fucking cd
80%
First time
Ever since I was a teen I wanted to get fucked by a tranny. At 19 I finally got the opportunity when I moved to Leicester for university. I did a quick google search to find any in my local area. I stumbled across sexy TS from Colombia with 44DD and a 9 inch cock. My cock got extremely hard after se... Read full Story
tshirt1017 2015-10-08 8,748 first time tranny ass fucking mouth fuck anal virginity
96%
My First Time
Hello, I've read a few stories on here some good most bad. I figured I would throw my own experience into the mix and try to bring something fresh to the table. I feel like you can tell most of these are fake, so here is a TRUE story about my first time with a trans girl. Bac... Read full Story
CiCi Kewt 2015-11-25 10,414 first time tranny ass ass fucking teasing teen TS (18+)
92%
A Hidden Surprise
Winter term at uni means thicker clothes which enabled me to hide some surprises under my clothes. The thicker blouses and tights would conceal anything from a thin g-string or a heavy lace pair of panties. And, me being me, I took this change of wardrobe to my full advantage. I’d been Matt’s fuck b... Read full Story
ATC97 2016-12-20 14,386 anal Teen (18+) Crossdresser Big Cock doggy style
80%
Kylie and Chrissy
The following story is the first part of ‘Kylie and Chrissy’, a story documenting the blossoming sissy-hood of two teenage boys. It is partially autobiographical and partially fiction. PART 1 - THE INCIDENT ‘Stop… we really shouldn’t be doing this’ ‘It’s just a bit of fun. Now just hold sti... Read full Story
chasingrisque 2017-01-09 8,284 Teen (18+) Lingerie crossdressing sissy friends teenager (18+)
70%
My sissy experience
I guess you could call me a sissy, maybe even a whore but one things for sure... I love cock. So my story begins as a young teenage boy, curious like most. I would raid my sisters panty drawer for the excitement of trying on her sexy lingerie. It became an addiction, I couldn't help but want mo... Read full Story
Emilysweetxo 2017-06-26 10,295 Crossdresser solo cd sissy teen cd (18+)
71%
The story of how I became what I am now...
I was on a trip to Germany with some of my friends. I was 16 when this happened. We went to a club one night and I got really drunk. They challenged me to approach a cute girl and ask her for a drink with me. I was drunk so I didn't really care so I went there and bought her a drink. We talked and I... Read full Story
FeetQueen 2019-01-08 6,031 Stockings Teen (18+) Small Tits Amateur Shemale Fucks Guy Lingerie Homemade cum in mouth
54%
The day i bought my fleshlight and it was better then i expected
We have all been there, you want something bigger and better than just jerking off, not sex but something that you can enjoy solo. We have all seen that famous American Pie scene where Jim decides the apple pie will feel amazing to fuck and proceeds to shove his dick into it and if I really think ab... Read full Story
BalkanLoco91Ri 2019-08-07 5,025 Teen (18+) solo Amateur Cumshot Masturbation Creampie Big Cock Lingerie Sex Toys Homemade
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 4,603 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 6,172 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
80%
Physical exam that embarrassed the fuck out of me.
Hello and welcome. My names safebet1980 aka Dug if you want a easter name to remember lol.. Right about now some of you are saying to your selfs that name sounds familiar and it might. If your looking at porn I'm on a lot of sites both as a user and a uploader of Amateur videos I both shot and sta... Read full Story
safebet1980 2022-10-11 5,051 Amateur Homemade
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 1,707 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
50%
MON NEVEU GOUJON ⚧️ ⚧️
"Daadddd, est-ce qu'on doit vraiment faire ça ?" ma fille pleurnichait. "Je suis aussi mécontent que toi, Tracy, mais je ne pouvais pas dire non. Tu es stagiaire dans leur magazine l'été prochain, tu te souviens ? Un bon tour en mérite un autre." Elle m'a juste fait la moue. Tracy est une étud... Read full Story
Femboy 2021 2023-04-16 1,639 Teen (18+) Blowjob Big Cock domination sissy sissification cum in mouth sexe anal féminisation Sissy
83%
Did I Do Right By Taking Money For Sex?
I first properly dressed when 14. (I did do the knickers and stockings and pantyhose thing previously from when I was 11). I first had sexual contact with a friend when we were both 14, i.e. wanked each other then I sucked him off and drank all his cum. I then waited until I was 16 for sex with... Read full Story
Linda Tiffany Vista 2024-05-07 3,545 anal Blowjob blonde Lingerie shemale fucks shemale cum in mouth teen (18+)
100%
Becoming a Chrissy - Chapter 2
I had always felt like I had a hot body for a girl. I was naturally blonde and smooth; I guess I had been blessed by my parents’ Scandinavian genetics. My pubes were always just a small fuzz—easy to shave and keep a clean bikini line. Same thing with my armpit hair. And my ass? Completely smooth and... Read full Story
mindlessrobot45 2024-05-13 4,475 Crossdresser gangbang Shemale and Girl cum in mouth shemale fucks female teen (18+)
50%
Eromenon vs mature whore
An eromenon for a mature whore When I looked up to see whose mannequin hands was serving my, I was surprised to find a girly-boy: ‘Something else,’ (s)he smiled, dragging his/her long, colourless varnished fingers across the tablecloth. I couldn't hold myself: ‘You've got the most beautiful ... Read full Story
hippocampus_171 2024-11-09 778 anal Crossdresser Amateur Blowjob Sex Toys Mature small cock big ass sissy femboy Ass to Mouth cum in mouth teen (18+)
71%
My first Bareback
Ron and I had been talking online for a few weeks now. We wanted to be comfortable, and make our intentions clear with one another. He was going to give me my first bare back sex, so i wanted to make sure it would be okay. We finally decided to meet last weekend. Through the course of our conversati... Read full Story
shemale lover 2011-10-06 3,715 anal first time shemales
95%
Interesting Suprise
This all happened several years ago when I was in the Navy in San Diego. One payday weekend I was in a partying mood so I thought I would head down to Tijuana for some fun. Being I was about 20 at the time I headed for one of the clubs where a lot of the college kids hung out hoping that I might g... Read full Story
bjw_6 2011-10-23 8,150 suck Bareback Shemale Fucks Guy Guy Fucks Shemale 69
100%
My ideal first time
We talk online for long enough to build trust. He is aggressively letting me know how much he wants to fuck me. His size is bigger than 6. He is physically larger than me and slightly older. After cumming to and on my pics several times over the course of weeks or months, we finally decide to meet. ... Read full Story
sexysugar 2011-12-14 3,485 first time Crossdresser Bareback
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 22,312 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
84%
The One That Got Away
I was out on a Friday night seriously just looking for a couple beers and a burger. I had a lot of work to do around the yard and house on Saturday and was having some guests for brunch on Sunday. Full weekend, tired from the week. I went downtown to a new gastro pub I’d seen reviewed in the local p... Read full Story
Giantsquid 2017-05-15 5,999 Amateur Bareback Lingerie guy on shemale
70%
Anally destroyed by a Peruvian goddess
Browsing around the Transsexual escort ads here in town I found a new girl, something else than the typical manly faces with heavily photoshopped pictures. A Peruvian girl named Isabella had just arrived in town and was open for business. She has a few retouched pictures but also some natural selfie... Read full Story
Gracemel121 2017-08-07 14,212 Amateur Cumshot Bareback Shemale Fucks Guy Lingerie domination
100%
An Amazingly Intense Encounter
The front doorbell ringing woke me from a pleasant nap on my living room sofa. It was late in the evening, and I wasn't expecting anyone to drop by. When I opened the door, there you stood. From your long, pulled back hair, to the red leather bustier, ultra mini black leather skirt(so revealing... Read full Story
coldasicefire 2018-03-04 3,939 Bareback domination
90%
White dress!
It had been a long and hot day that sunday! Some friends opted the idea to go drinks and have a cookout, little did i know how the night would end. By the time it got to midnight we were all drunk and wanted more action so we decided to head to one of the local bars for more drinks and see if we fo... Read full Story
PeterPiper 2018-03-22 6,433 Masturbation Bareback Mature Ass to Mouth cum in mouth
63%
What are Friends For?
I was over at a friends house for guys weekend. I was up early Saturday and went downstairs to watch TV, so I wouldn't wake anyone up. Nothing was on cable, so I checked what else was on, Net Flix, etc.... There was Firestick, so I checked what movies were on there. I found one that was marked ... Read full Story
MARKUS6969 2018-04-09 8,140 Group Sex Masturbation Bareback gangbang sissy slut gay orgy
100%
Seattle Weekend Part 2
I awakened to the smell of coffee and this beautiful silhouette of a girl standing at the window watching sunrise. I could see through her lingerie the beautiful breast and nipples, and the silhouette of her TG butt which was so sexy looking I was getting hard. I joined Gwen at the window wrapping m... Read full Story
Jon Paul 2018-08-13 7,157 Big Tits Cumshot Bareback Ladyboy Guy Fucks Shemale cum in mouth
84%
When I Knew I Was A Crossdressing Sissy Slut
I remember the fun I had taking selfies with sexy little outfits and make up on. I loved the dirty,sexy feeling of taking pics of me exposing my asshole and sliding back onto a suction cup dildo stuck to the wall. Hearing from a guy just how much he wanted to eat my ass or fuck me always got me ting... Read full Story
pennypenny 2018-09-05 7,707 Crossdresser Cumshot Bareback Blowjob Guy Fucks Shemale Ass to Mouth cum in mouth
94%
My First Time Made Me A Slut
A true story of my first time. And why I so need a daddy now. The first time I went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to pull it down as cars were wizzing by. I walked or should I say wobbled the... Read full Story
Teddie 2018-09-12 13,136 first time Stockings Crossdresser Bareback Blowjob blonde Big Cock gangbang domination Guy Fucks Shemale slut cum in mouth
100%
All Woman and More
It was one of those soft southern nights you hear about in movies and old soft rock songs. I could smell the long leaf pines and the moon was nearly full. I had been on my own for so long that it rarely bothered me as it did in my youth. That lonely feeling that never quite goes away. Now it came on... Read full Story
Windmillchaser 2018-09-20 11,018 Bareback Shemale Fucks Guy Big Cock sensual romantic encounters Erotic Fiction
95%
Late night park visit
It was 11pm on a Friday night, I was driving my car back from a failed meetup with a guy I met online a couple of days prior. I thought it was going to be an amazing night, so I spent close to two hours getting my makeup and hair sorted to look pretty for him when we met. I was wearing a short black... Read full Story
Natalie Bishop 2018-10-08 7,613 Amateur Cumshot Bareback Creampie Big Cock Ladyboy domination Guy Fucks Shemale public Park
98%
When Fantasy Comes True 2
After my first threesome encounter with Jenni and her friend, getting a golden shower from three trans women was a bonus. Being drunk and now four of us snuggled in bed, i thought the night had ended but i did hope for more. I was not disappointed as Jenni's friend (Sasha) who had been sleeping d... Read full Story
Sara Banks 2018-10-22 12,267 Group Sex Cumshot Bareback Shemale Fucks Guy threesome Blowjob Big Cock gangbang domination Ass to Mouth cum in mouth golden showers golden shower
90%
My Recent Holiday Treat
I've come to accept that I am a bit of a dirty girl sometimes. Most of the time I think that I could easily fall into be labeled a nerdy, quiet goth girl, book worm and not at all up of current trends. A misfit as I was called in high school. But there's another side of me. A side that craves sexual... Read full Story
Gothtransgirl41 2018-12-04 7,011 Group Sex Bareback Big Cock Ass to Mouth cum in mouth shemale + shemale
100%
MY First Time with a non-binary/cross-dresser
After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... Read full Story
ghostpeople 2019-03-12 7,622 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
87%
Chance Encounter 4/7
With her feet still pointed she starts slowly spreading and rubbing her cream over her nipples while i’m thrusting my cock in and out of her sweet hole. Her hole felt so beautiful! In and out I thrusted until I pulled out. I grabbed her hands, lifted her a little and pulled her towards me as I stood... Read full Story
Katlick 2019-10-30 5,449 Bareback Creampie Big Cock cum in mouth
81%
the pool house
Hello there stranger, I am glad you have taken the time to read my story of the morning I first got my cherry busted open, it was a typical beautiful southern caalifornia morning, nothing out of the ordinary. I clean pools up in the palisades above the Santa Monica moutian range, high dollar propert... Read full Story
Cutmycakeplease 2019-11-04 10,427 anal Bareback Creampie Shemale Fucks Guy blonde Big Cock ts stranger virgin ass surpise
80%
Transsexual Savage
John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... Read full Story
Anal Orgasm 2020-07-10 6,714 Big Tits Outdoor Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Guy Fucks Shemale