Sort by
Relevancy

Free Stories

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 10,866 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
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 4,919 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,892 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
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 7,167 anal Amateur Bareback Creampie Blowjob femboy Ass to Mouth
100%
My Favorite Trans Model Turned Me in to Her Slut
A couple months ago I was on a trip out in Las Vegas for work. We had some down time after dinner and I was pretty tired of socializing, so I went back to my hotel room to relax. I found myself pretty bored and horny, so I started watching porn and jerking off. I’m married to a beautiful woman, and ... Read full Story
strongjohn518 2024-12-02 1,947 anal Cumshot Bareback Blowjob facial domination virgin rimjob Ass to Mouth gape gaping Hookup topping
100%
First Encounter (Mexican Travesti)
I grew up near the U.S.-Mexico border and am ½ Mexican Hispanic and ½ Anglo (white). I visited Nogales Senora on the Mexican side on and off during my teen years. As a young adult, I was fearless and sometimes went across alone to visit the strip clubs, get a cheap lunch, or look for Mexican sweetie... Read full Story
AllenB 2022-09-07 7,378 anal sex Shemale Fucks Guy Blowjob mexicana cum in ass first time with a tranny
50%
trans=demic
Trans-demic Chinese Flu Sam Wong read the email from Josh Epstein, the partner in charge of the fiendishly complicated real estate deal that had consumed the last three months of their lives. “You’re going to have to close this deal without me. I’m sick as a dog, and my wife just called an ambu... Read full Story
the greatest liar 2024-09-09 1,693 anal Small Tits Bareback Creampie Asian Guy Fucks Shemale small cock Ass to Mouth 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 5,814 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
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 19,942 anal Amateur Cumshot shemale escort top
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 4,088 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
92%
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 10,557 anal first time Amateur virgin cd
100%
Regina's scary, and sexy Blind Date
I had just finished doing my makeup, finally deciding which blush to use, and I thought I had some time for my meditation. However, Mr. Cobb was early. The gold minidress I wore showed enough legs, ass and tits to make any man horny, and the strappy tanned five-inch sandals, made me feel majestic ... Read full Story
Regina10 2024-03-18 5,289 anal Crossdresser Bareback Creampie Fetish Blowjob Ebony Guy Fucks Shemale big ass sissy Ass to Mouth cum in mouth
100%
Late Night Snack (Touch me in the morning)
I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... Read full Story
Regina10 2024-03-28 4,426 anal Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ebony Ladyboy Lingerie
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 3,868 anal Amateur Shemale Fucks Guy Big Cock Guy Fucks Shemale small cock big ass
66%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 6,515 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 7,655 anal Shemale Fucks Guy Big Cock Frottage
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 6,967 anal Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Asian
100%
Taxed Pleasure
Taxed Pleasure In the dimly lit, seedy adult theater on the bad side of town, the air was thick with anticipation. Among the shadowy figures, a tiny, petite figure stood out. At 4'10" and 75 lbs, with a micro kini and super high heels accentuating her diminutive frame, she drew attention despite he... Read full Story
SlutTraci 2024-10-14 1,301 anal Big Cock Interracial sissy femboy
71%
Trans secretary
"Monica Barnes smoothed her skirt before entering the office of her boss, Cord Drake, the CEO of the company his father had founded thirty eight years ago! Like every other morning for the past two years, she brought along his coffee, her memo pad, and of course his copy of the morning paper! &... Read full Story
shemale lover 2012-04-30 4,569 anal sex Cumshot Big Cock oral sex
100%
Double Anal With a shemale
....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36... Read full Story
shemale lover 2015-04-29 5,786 tranny suck Big Cock ass fucking dp precum
100%
Oneness with the bodies
many years went into just fantasizing being with shemales. I was getting hornier day by day to try it out. But being in a relationship there was hardly any room or time for it. I once experienced it in bangkok and confirmed that I really can do it and actually love it. One day suddenly it was br... Read full Story
zyankhaan786 2023-05-30 6,893 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
100%
The Interview
The Interview By Sabrina G. Langton *** 'A crossdresser goes on an interview in lots of pink, of course she gets the job' 'Author's note, just a quick little story with some really graphic sex, and a little tiny moral. I hope YOU like it.' *** "Okay, sit, sit, let's get started. S... Read full Story
Brina Giselle 2023-12-04 7,168 anal Crossdresser Blowjob heels cum in mouth pink dress
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 3,793 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
33%
Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
the greatest liar 2023-07-19 4,498 anal Bareback Creampie Ebony Guy Fucks Shemale post-op celebrity post op sex
91%
My TS Journey
I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my a... Read full Story
iconicirish 2022-10-26 8,797 Amateur Shemale Fucks Guy Big Cock domination cum in mouth escort ts
100%
Straight Boy Cock
This is my fantasy. I want it to go like this. I meet a straight guy while I’m putting gas in my car. He offers to pump my gas for me because he’s a kind gentleman. So I let him. I can tell he wants to fuck me and I want to “repay him” so I take him home with me. He has no idea that i’m trans. I und... Read full Story
CocoBombPussy 2023-11-03 7,893 anal sex fantasy Love transwoman trans pussy Straight Boy Cock
92%
Lola - chapter one
This is a fantasy but with a lot of inspiration from real life experience. More chapters to follow. Chapter 1 So now I knew, without a shadow of a doubt, what it was that caused this familiar smell in my house - and where it came from. When I got back home my laptop was lying open on the kitc... Read full Story
BellaBeau 2023-10-05 6,819 anal Amateur Cumshot Masturbation Bareback Blowjob Guy Fucks Shemale Frottage Homemade
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 6,582 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
50%
DE BRO À SISSY ⚧️ ⚧️
Mon ami Magnus et moi nous sommes connus presque toute notre vie. Nous nous sommes rencontrés en pré-maternelle, quand nous vivions à un pâté de maisons et demi l'un de l'autre. Nos familles étaient proches et nous avons grandi côte à côte. Nous nous connaissions depuis si longtemps; nous nous appel... Read full Story
Femboy 2021 2023-03-26 1,465 Blowjob Big Cock domination Sex Toys feminisation bbc cum in mouth bdsm scene soumission cocu poule mouillé femme chaude
100%
I Believe
I Believe I had just started my senior year in college and was in my 3rd year of transitioning from a male to a female. I couldn’t start in high school so when I graduated and I started college I started as Nikki. The first three years working on my communications degree I used to see people goin... Read full Story
ShelleyParker 2024-07-08 3,512 Bareback Big Cock Guy Fucks Shemale Interracial Ass to Mouth 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 9,596 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
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 12,463 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%
The Feet I Love
There is something so beautiful and alluring about trans women and their feminine feet. The sight of their soft soles and their penises, whether soft and folded over their pretty sacks or standing erect and proud, completely excites me. I find myself gravitating towards photos that show a woma... Read full Story
Feet_love 2022-10-24 3,588 anal Blowjob trans feet tanned trans feet
100%
Lola Chapter 2
Lola Chapter 2: A couple? It wasn't as if we were together. We had jerked off together once, and of course we slept in separate rooms, but I slept restlessly that night. Dreamed something scary that I couldn't remember in the morning. I didn't have work scheduled that day so I took it easy. When ... Read full Story
BellaBeau 2023-10-05 5,886 anal Cumshot Creampie Guy Fucks Shemale Homemade latina Tgirl
100%
Best Ride Share of My Life
It was a random Friday night. I was feeling a little frisky but didn’t have anything specific in mindA friend of mine works at a gay bar not too far from my house. Knowing my friend worked there I figured I could head over around midnight and see if there was something worth getting up to and if not... Read full Story
baldbeardbottom 2024-01-16 6,795 anal Amateur Cumshot Bareback Lingerie Guy Fucks Shemale Homemade
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 3,965 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
Claudia Coming out adventure part 1
*Author's Note: This story starts off being told in First person and after awhile the story shifts to third person* Hello everyone, my name is Claudia I am a Cross dresser who one day hopes to be transgendered, although I do not want the surgery, I am looking to eventually live my life full... Read full Story
MissClaudia 2015-01-04 6,321 tranny Stockings suck Creampie ass fucking doggy style Latex
100%
Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
darrell 2022-01-03 5,541 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
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 4,976 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
91%
A New Year's Resolution
I'm not gay (laughing), with that said, I have seen some very good looking, uh, guys. Okay, go ahead and laugh. You see, toward the end of this past summer (August 2011), my wife and I visited an old friend of mine in Pattaya, Chon Buri, Thailand. He's a former Navy Seal. I'm a former Army Ranger as... Read full Story
shemale lover 2012-04-16 8,009 anal sex cum oral sex
40%
Little tranny for old pervert
It happened not later that there was 15 days. I do not hide I'm bisexual and love as the amorous jousts with men than women. I also like the transsexuals and trav .. There was a long time that I had not played with one of these wonderful creatures. And this weekend I was lucky. I always trolling ... Read full Story
shemale lover 2012-03-17 5,027 taboo anal sex sucking sperm rimjob
100%
How I have become a girl
I just want share my story of becoming a girl, which I really enjoy at the moment. I am now sitting in my heels, fishnet bodystocking and my alpha male just went home. Yes I was fucked hard and i now love men. My ass is burning, but that is what I wanted the whole of my life - wearing women's clothe... Read full Story
SlutMonica99 2019-06-11 5,810 Crossdresser Amateur Bareback Big Cock
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 9,616 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
67%
The New Boss
My name is Jacklyn. I am 27 years old and was just promoted to Vice President of BB last week. I'm not a stunner but I have an okay body with a nice shape to it. I begin working here when I turned 20 and found it to be relaxing. However what everyone called the "Upstairs Crew" were very qu... Read full Story
shemale lover 2014-03-19 7,586 anal threesome trans
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,682 anal hardcore erotic encounters fantastic
100%
A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
Gtaaddict3 2023-11-21 9,956 first time cock suck Blowjob shemale Big Cock trans oral fantasy virgin escort big first time
100%
Hits, Misses: G
Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibili... Read full Story
bybaking 2024-02-06 5,228 anal Amateur Cumshot Bareback Big Cock Ebony Guy Fucks Shemale Interracial black Tgirl
86%
Valerie Halls Car Trouble
I am a teenage trans working my way through college was on my way home from my night job at an adult store in my little SUV when the engine died so I pulled over to the side of the road and put my flashers on. I get my cell out called the roll back service that I knew and waited a short bit for Henr... Read full Story
CeeRVee 2017-05-02 6,471 fingering ass fucking hard dick stroking Ass to Mouth
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 5,887 anal Amateur
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,974 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
My first Escort girl
I was in my early thirties. I had just out of a relationship that ended very brutally. I was hurt for several years as I took it difficult. It was at this time, already having had my first sexual experience with a Crossdresser/Ts when drunk and still thinking of that experience that I decide... Read full Story
likesboth 2024-11-05 1,942 anal Cumshot Blowjob Big Cock Asian Frottage femboy
100%
A Reluctant Gang Bang
Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... Read full Story
shemale lover 2012-05-28 8,950 anal sex Creampie Fetish gangbang crossdressing
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 8,049 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
100%
Used in a hotel room
This is a recurring fantasy I have about being used in a hotel room. I’m working on making this a reality but for now this will have to do. I travel a lot for work and end up in many cities across the world. Usually I am out and exploring bars and restaurants. Always ends with me jerking off alo... Read full Story
slvr2291 2023-01-11 5,055 anal first time Big Cock fantasy Surprise
81%
My First Shemale
Let me tell you a little bit about myself I’m five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I’m an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the ... Read full Story
shemale lover 2018-02-10 18,460 anal cum oral
100%
My first time with a shemale
Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking l... Read full Story
shemale lover 2011-08-23 4,171 anal sex cum oral sex