Sort by
Relevancy

Free Stories

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 8,231 first time tranny ass fucking mouth fuck anal virginity
100%
First Time With a Shemale
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we... Read full Story
shemale lover 2012-02-12 6,039 first time Cumshot sucking
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 3,348 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
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 5,020 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
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 6,975 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
95%
How I became a cute femboy CD part 2
The game of husband and wife Kevin and I played went on for a little over 2 more weeks before we decided to go even further, I say we but it was Kevin who seduced me into it. We got together in our game as much as we could and it was a lot. I would always dress for him in various outfits and my ... Read full Story
Cute_Femboy 2016-04-05 12,146 first time oral sex nipples crossdressing cd sissy
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 6,851 anal Shemale Fucks Guy Big Cock Frottage
83%
First Time for Everything
At the time I was living in Paris and on sheer whim, I decided to go to Amsterdam for the weekend. I thought to myself, "what better place to act out my fantasies than in Amsterdam?" I packed some of my slutty clothes. I decided on my slutty cowgirl outfit complete with flannel top, jean s... Read full Story
shemale lover 2012-10-14 4,184 anal sex orgy facial huge cock sucking off
90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 12,346 first time cumming crossdressing cd sissy cumshot in mouth
91%
How I learned the pleasures of anal
This narrative is the journey that lead up to my first experience with anal sex. The details I have here are as accurate as I can recall and any dialog is essentially the best of what I can remember now. It of course gets more sexually explicit and graphic towards the end... I was born and grew u... Read full Story
Dressed2Thrill 2015-07-29 9,969 anal first time Amateur virgin cd
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 12,977 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
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 21,830 Crossdresser Amateur Shemale Fucks Guy Sex Toys Homemade cum in mouth
100%
My 1st Time was Not the Only Time.
One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... Read full Story
LesFuax 2019-02-16 9,024 first time Small Tits Amateur Latina Bareback Creampie threesome Blowjob Big Cock ass fucking barebacking barebackedshemales first time with a tranny raw anal raw dick raw fucking firsttime
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 3,929 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,840 first time sucking fuck domination
100%
Don't "DRAG" It Out Of Me...
I was a Service Brat; living near FT. Hood Tx. at the time, and had just turned 14. My friend Peter was a little more than a year older than I, and we had started getting each other off with hand jobs but nothing else during the previous summer. One day after we'd finished swimming, he asked if ... Read full Story
DJFreak201 2012-11-22 3,281 first time Frottage first tranny
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 14,004 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
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 2,634 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
33%
sex
Hello I am mahan Very handsome and curious. The date goes back to last year. With our sister, Sepehr, from childhood, we were on the floor of Khalmun Arshida's daughter. One day we went out with the scene, Arshida called me and his parents went to Istanbul and that lone. And asked us to go over the... Read full Story
sima2000 2019-04-18 3,586 Amateur Big Tits Creampie gangbang Shemale and Girl pov double anal
100%
My new Life with Pat. Part 2
While Jean was discussing with the lady from the next table i feel the didlo starting to vibrate and then something like a small ball move up and down into the didlo, it was a prostate massage. I saw Jean playing with a remote control, He increased and deacresed the frequency of vibration and the ... Read full Story
jperrot 2022-08-09 4,826 Amateur Bareback Shemale Fucks Guy threesome Shemale and Girl domination Guy Fucks Shemale slave Ass to Mouth double anal webcams punishment
88%
My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
Nicole_femboyCD 2014-12-03 20,927 anal Crossdresser Cumshot Blowjob rimming cd
100%
First Time S & M Whore
Suellen certainly looked the part of a cheap S & M whore: black seamed hose, shiny pink patent 5 inch heels, a black leather miniskirt, and a translucent white nylon blouse that clearly showed the black bra underneath. Her long blonde hair swayed seductively and naturally. Well the hair was natu... Read full Story
shemale lover 2012-10-24 5,083 Cumshot oral condom sex
92%
A Shemale and Her Unexpected Friend and Me
There I was on the boardwalk waiting for texts back from trannies from craigslist. As I sat staring at the ocean, I yearned for some sexy shemales to get back to me. I started walking around the boardwalk more, anxiously, desperately. All the sudden, a beautiful older woman was walking by with her d... Read full Story
tysonsbakery 2015-11-16 6,777 tranny ass shemale domination double anal
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 6,635 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
100%
Danielle's First Time
Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... Read full Story
shemale lover 2012-02-03 5,429 cum dildo fingering
60%
My Fantasy Came True
Hello all I'm a trap or a CD or a Sissy anything you can call me.I can be your trap or Sissy. Here is my first BBC Gangbang. When I got my fantasy fuck.I'm a Sissy Bitch of my friend.He make my fantasy came true.So here's the story. Last week I got my First BBC Gangbang.It's... Read full Story
TrapBomb 2016-09-26 8,915 Big Cock gangbang deep throat double anal trap c
82%
First time with a trans escort
I've thought about seeing a t-girl escort many times and a few weeks ago I finally made a date with a local girl named Carol. She´s a lovely Colombian girl with long dark hair and a slim, sexy body. She welcomed me into her home wearing a sexy black dress and high heels and after pouring a d... Read full Story
Gracemel121 2017-03-28 19,295 anal Amateur Cumshot shemale escort top
87%
Melissa
I'm a Japanese in my early forties living in Japan and I met Melissa online about a year and a half ago when looking for someone to chat. She is a black, 6 feet 2 inches tall, around 160 pounds and therefore a slim and beautiful transgender girl in her mid twenties. From Brazil, she is very friendl... Read full Story
cttyy 2020-02-24 15,361 Shemale Fucks Guy threesome Big Cock domination cum in mouth double anal
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 4,908 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 2,984 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
92%
Candy's Treats
"Hi, I'm Candy," the pretty blonde Latina said to me as I sat alone in the casino bar. She had a nice pretty face and a great body with a store bought pair of dd's. I knew the moment she sat down that she was a pro. Five straight years in Vegas at the show had taught me how to spot them in... Read full Story
shemale lover 2012-03-06 5,400 first time anal sex Latina sucking cum
100%
My first gay experience
Unlike most stories mine is from experience. There is no subtlety or seduction just an account of my first time. I had weekend fishing trips with a mate called Simon, we jointly owned a caravan which we used as out base. We were both in our forties. We are both married and our wives know each other... Read full Story
lkusex 2021-05-27 3,115 Amateur Blowjob Big Cock
0%
The Greatest Lie Part 16
As soon as we were safely back in our hooch, I retrieved the iBook from its hiding place under the floor and opened up Spartan's main Excel spreadsheet. I re-sorted the list against the data from the last three weeks of our frustrating field work, by district, language group, age, and every other ca... Read full Story
shemale lover 2012-01-20 4,946 first time femdom crossdressing
100%
A Mate's Trans Date
I had been seeing Nikki for about 6months and taking her out as you would any girlfriend, sharing our groups of friends socially of course. One evening we went to a friends place and when Nikki has snoozed off to sleep on the sofa me and my mate called Al got talking, we had been drinking most of th... Read full Story
shemale lover 2012-03-19 4,547 first time Stockings anal sex oral sex
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,159 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
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 6,547 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
First time.
Long did I contemplate ever meeting a trans gurl to fulfil my darkest desires. Sometimes I would convince myself that it's only a fantasy, other times consumed with the thought, even waking up in the middle of the night with a rock hard erection. My choice was clear. Try it. What do I have to lo... Read full Story
Danshorny 2023-05-11 5,610 anal Amateur
85%
The Gang
I had always thought of myself as female in spite of the fact that I was born with male genitlia. Even in my earliest memories where I had witness sex, I identified with the female in the relationship. As a small young child, I had always longed for womanhood each time I heard a woman sing or especi... Read full Story
Regina10 2020-06-29 8,765 Group Sex Cumshot Blowjob Big Cock Ebony gangbang double anal
0%
Giving my first blowjob
I was recalling the first time that I ever gave a blow job while I was jerking off last night. I thought I would tell you the story and share what my experience was like when I finally took the plunge and made my first attempts at having sex with a man. At the time, it was a little awkward, but the ... Read full Story
SissyAnalPrincess 2021-05-11 4,841 Amateur Blowjob Danni Cherie
100%
The Three of Us
Imagine you are a lonely person on the inside, and just wanting all your life to be loved for who you are. Holli Artigas, was just that person. Wondering whether her obsession with Jon Silva, a football star, was from a casual encounter, or was she truly fond of him? Growing up in the Sao Paulo, ... Read full Story
Jon Paul 2024-04-28 2,521 anal Creampie Shemale Fucks Guy threesome Shemale and Girl cum in mouth double anal shemale fucks female
90%
My first Theesome
I'd been flirting with Clare for a while in work. I always thought she would be one of the girls that would play around in work, but never actually go through with anything. It was a slow day in work and as usual the subject came round to sex. We were having a cheeky conversation about fetishes a... Read full Story
cdleesa 2020-06-01 14,298 anal threesome bisexual forced bi
85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 7,534 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
100%
Regina's Vagina dreams
I think I wanted to be a female from birth. I once looked through a girlie magazine out of curiosity. I had impossible dreams and I longed to trade genitalia with them. I have always fantasized about my Vagina when I was younger. It was during those times that I would drift into my own private world... Read full Story
Regina10 2024-03-01 5,072 anal Big Tits Bareback Creampie Blowjob Big Cock Ebony gangbang Guy Fucks Shemale big ass cum in mouth double anal
56%
First black T-girl
I've been wondering what to write about lately. I've received a request to write about me and my sister, but that is a road I might have trouble going down. Today I was thinking about my bi-sexual stripper girlfriend from the past, who loved bringing home other strippers (mostly lesbians) for some h... Read full Story
bigtranslover 2014-01-01 6,980 first time shemales interracial sex
50%
Eric...a
There was no doubt that this was going to be my last baseball game in organized ball. I knew that after high school I would not get a chance to play anywhere else, save for the drunken beer league down the line. I was an average player who played for a small school. I played second base. We were los... Read full Story
shemale lover 2012-04-18 5,699 first time anal sex jerking off crossdressing
100%
Fixing her computer
I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I s... Read full Story
shemale lover 2012-08-23 7,835 first time anal sex orgasm
100%
Surprise while exploring dressed
I had been dressing at home for a while, taking pictures and enjoying myself. Usually whenever I had any sexual encounters I was not dressed and had a mixture of experiences as top and bottom. This is the day it all changed though. For the first time I decided to get myself dressed and head out.... Read full Story
slvr2291 2023-06-21 6,892 anal Amateur Big Cock cd first time dressed
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,182 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
First intercourse with a man
If you read my previous story, “First time with a man”, I gave my first blowjob. What I didn’t mention at the time, was that I was on my way to work about 2pm in the afternoon, (I worked the swing shift). That afternoon meet up was just to see each other, talk and maybe meet again later. But my e... Read full Story
Mistysis 2020-10-23 7,104 Crossdresser Amateur Bareback
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 3,883 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%
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 3,504 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 4,901 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
I wanna fuck almost everyday
I can't stop thinking to be Double penetrated for two men at the same time.... It makes me feel I'm insatiable gurl... Two Big cocks mmmmmmm after been fucked for so long ... I will never go back... And certainly I will totally satisfied and addicted to it...... Read full Story
Bellasohot 2022-07-13 3,733 Crossdresser Amateur Latina Bareback threesome Big Cock Ladyboy Lingerie Guy Fucks Shemale Mature Ass to Mouth double anal
100%
Sultry Mistress,
Sultry Mistress, Natacha has now been living with me for over a year. It is a cerebral and perverse Domina who immediately wanted to submit me to her desires. She took power over me by making me discover my femininity during role-playing games. Like a spider, she imprisons me in her web a ... Read full Story
sandratvtg 2022-09-20 3,961 Stockings Amateur Lingerie domination Sex Toys
100%
HE DIDN'T KNOW 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
mika96 2023-05-11 6,512 anal Amateur Bareback Creampie Blowjob femboy Ass to Mouth
16%
Current Fantasy
I really wanna get fucked for the first time and my dream way of doing it, always wanted to do a porn. The dream is that I go there and get done up in such a way, I am unrecognizable, just looking the best. Have a tranny come in and do my make up, the way she likes it and gives me a preview of what ... Read full Story
martley 2023-06-30 5,121 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth