Sort by
Relevancy

Free Stories

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 6,608 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
63%
My life as a tgirl teen slut. part 1
My name is sapphire. I'm 18 and an escort in the sex capital of the world, bangkok Thailand. I've been on hrt for 6 years and it shows: I have a banging tight body with 34C natural breasts, a small waist, cute tight jiggly ass, and a 8 inch cock that drives all the boys wild, they clamor f... Read full Story
Bbunny 2018-03-06 5,113 Teen (18+) escort part 1
71%
First time cumming while fucked
When I was young, my girlfriend's older black brother blackmailed me after he caught us having sex. I was made to suck his cock on a regular basis, sometimes while my girlfriend watched. One day he pushed me off his cock, made me turn over with my ass in the air. He poured canola oil on my ass ... Read full Story
Julliana 2016-11-22 10,873 first time Teen (18+) Blowjob cum ass fucking
92%
Crossdressers first time with a guy
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
shemale lover 2013-06-06 10,879 first time Teen (18+) hardcore anal sex fingering Interracial cd
40%
My 1st time with a CD
I was getting tutoring in HS and the tutor and I usually met at the library. This day he asked me to meet him at home because his wife was out of town and he had chores to do. No problem I thought. When I arrived I could tell he's been drinking. He offered me one which I took. He excused hi... Read full Story
BeachloverinNJ 2018-03-02 3,763 Teen (18+) Crossdresser Cumshot Bareback CD teacher gets me
100%
First Time Buying Lingerie
As a youngster, I couldn't help but notice the carousels of hosiery on display in various shops that my mother would visit. Displays of stockings and tights (pantyhose) for the discerning housewife. Brands like Pretty Polly, images of nylon clad legs on the glossy cardboard and a see through window... Read full Story
Daddybear71 2023-09-13 7,070 Stockings Crossdresser Amateur Masturbation Lingerie teen (18+)
66%
First Time With A Man
Just a true story, first of a few telling how I got where I am: First Time With A Man: Ok, pretty tame but here goes... One night when I was about 14 or so a strange thing happened. I ran out of smokes... that's not weird but if you're a smoker you know it sucks. So I walked up to... Read full Story
lilslutmouth 2017-07-07 13,907 Teen (18+) Amateur Masturbation Big Cock
50%
wearing women's clothes for the first time
So now I have not completely dressed as a woman, it was just a pair of panties. But that was the first time I asked to do it and I did it too. and it felt great. when i was 14 i visited relatives in brazil with my parents (i come from germany). it was a great vacation even if i couldn't tal... Read full Story
menina porco 2020-08-26 5,035 first time Teen (18+) Crossdresser solo Amateur Mother In Law
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
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
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+)
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
84%
First Time: How I Love Cock
The first time I ever sucked a dick was when I was around 12 years old. I was at a sleep over with a friend. We were camped out in his backyard in a tent and he started things out tentatively by asking about my luck with the ladies, which was non-existent. Then he suggested that since neither of us ... Read full Story
wickeddogg 2019-12-11 34,371 Teen (18+) Cumshot Bareback Blowjob cum in mouth
83%
My first time with a guy
MY FIRST TIME WITH A GUY Another true story it’s kind of long but I think you will enjoy it I lived west of Lake Worth Florida. At that time we were surrounded by 1500 Acres of woods. There were 10 of us and we all had dirt bikes and would go out riding all the time.. On Saturdays we had a game ... Read full Story
Stephanie101 2024-04-26 4,800 anal Crossdresser Outdoor Blowjob cum in mouth teen (18+)
50%
SOUS LE CONTRÔLE DE MAMAN ⚧️ ⚧️
Jaime se tournait et se retournait dans un sommeil agité, ses yeux fermés et son visage grimaçant alors qu'il luttait avec ses rêves. Normalement, il s'endormirait paisiblement au son d'un podcast bourdonnant, mais pas dernièrement. Bien qu'il ne le sache pas, chaque nuit, sa psyché ... Read full Story
Femboy 2021 2023-03-18 1,255 Stockings Teen (18+) Crossdresser Lingerie domination Sex Toys
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-06 1,761 Teen (18+) Crossdresser Amateur Fetish Lingerie
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,986 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
50%
SOUS LA DIRECTION DE MAMAN ⚧️ ⚧️
Jaime n'avait jamais eu beaucoup de chance avec les filles au lycée. C'était venu et reparti, et maintenant il profitait d'un dernier été avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un salaud ou un douchebag, c... Read full Story
Femboy 2021 2023-03-18 1,528 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
66%
Awesome day at class =)
Sooo i'm in college. and one of my professors is really hot. he's older but looks like he's in his 30's. anyway, every single day in class i would notice his huge bulge under his pants and just couldn't help but wonder =P so i figured, hey maybe i should start flirting with ... Read full Story
Amanda Lips 2018-03-02 4,115 Teen (18+) Mature Homemade pov Ass to Mouth cum in mouth webcams
54%
hi is me
im happy later of much time im a verified model , because other person have much videos of me and is not good look your videos in other page is not your .... thanks shemale for give me the chance to be verified love you... Read full Story
Kimberly Polizzi 2019-08-21 4,005 Amateur Latina Big Cock Shemale and Girl Compilation webcams
93%
The Babysitter Chapter Two
Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women ... Read full Story
shemale lover 2016-03-06 18,061 tranny Teen (18+) jerking off
100%
Not so much a story as cry for help
Here is a story that is not a story but a problem, looking for a solution and i can certainly use some help. So please read on, keep in mind, all that everything is the truth and it is all real. I have lived as a transgender person since i was very young, and truly feel i am a female in a male... Read full Story
Wendytg976 2019-05-27 4,655 webcams
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 7,352 Crossdresser Lingerie domination Sex Toys femboy forced webcams
100%
Emily's First Daddy
This is a story how a curious male can become a sissy slut seemingly overnight. So I was in an online adult chat just talking with random people and happened to mentioned where I live. Then all of sudden, I got a message from a man calling himself bear daddy. He introduced himself and said he was ... Read full Story
User Removed 2019-10-21 9,508 Crossdresser Amateur Creampie Homemade cum in mouth webcams
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 5,477 Amateur Bareback Shemale Fucks Guy threesome Shemale and Girl domination Guy Fucks Shemale slave Ass to Mouth double anal webcams punishment
100%
Camming down the rabbit hole Ch2
How had I ended up in this situation? Sure I was going to need to make ends meet, but I could find a normal job couldn’t I? was I this desperate? Perhaps desperate wasn’t the right word, just over a month ago I had started out camming as a bit of fun, to maybe make a few pounds while I masturbated, ... Read full Story
Dani_does_Dallas 2021-08-11 4,038 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
Camming down the rabbit hole Ch4
It was the morning after the night before, and as I stretched under the bedsheets, a smile spread across my face. Remembering last night’s events, I felt myself stir a little and pressure from the panties I had on adding to the arousal. It has been a while since I had morning wood after a big show, ... Read full Story
Dani_does_Dallas 2021-09-06 4,344 Crossdresser solo Amateur Cumshot Lingerie Sex Toys Homemade pov webcams
100%
Crossdressing in a Hotel
Jamie was feeling excited as he entered the hotel room. He had been looking forward to this for weeks, and now he was finally here. He had dressed himself up in sexy lingerie, and had brought his toys with him. He had a normal dildo, a big dildo, a normal plug and a very big plug, and plenty of lube... Read full Story
Fischermensfriend246 2023-01-11 5,333 Crossdresser Amateur Bareback Blowjob Big Cock dildo Lingerie Interracial Sex Toys Ass to Mouth webcam webcams
100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 5,517 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
74%
Becoming the girl i really am....
I guess I'll start from the beginning, I was in my early teens and my parents had friends in town who we did everything with, travelling, camping, holidays, the works. They had a daughter who was a couple years older, and a son who was my age who was pretty much my best friend. We started masturb... Read full Story
shemale lover 2014-05-27 8,659 first time shemales licking
62%
Naples
I had been at sea about a month when my ship pulled into Naples, Italy. The only action I had seen had been slipping away to my hiding place on the ship to jack my dick on a regular basis. I was ready to find some Italian pussy. I was slim about 6' with blonde hair and a fat 7" cock that ... Read full Story
shemale lover 2011-12-16 6,837 Teen (18+) shemale gay
76%
Tranny hooker
I was out late looking for a cheap hooker with £15 in my wallet I should at least get a blowjob. After 20 minutes of searching I see a young girl stood on the corner. I pull up along side her she tall long legs short skirt stockings m holdups long dark hair as she bends down I tell her how muc... Read full Story
shemale lover 2012-01-05 5,065 first time shemales Fetish
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 14,638 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Camming down the rabbit hole Ch1
Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... Read full Story
Dani_does_Dallas 2021-08-11 5,880 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 5,363 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 4,009 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,984 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,846 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
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 14,736 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
70%
Teen pussy rendevous!
Yes, she said she would meet me at the same bathroom stall and would not you know it, she did exactly that! I was already in the ladies room, wahing my hands, and in she walks, absolutely stunning, heels on , short summer dress, beautiful face and hair and what a body, my cock got so hard right then... Read full Story
shemale lover 2014-02-23 5,643 sucking
93%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 40,562 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 34,987 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 8,261 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
78%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 72,915 Teen (18+) Crossdresser transgender sissy slut.trinity
100%
Allison the pool slut part 1
Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to... Read full Story
shemale lover 2013-06-05 8,289 Teen (18+) Cumshot Big Cock ass fucking Interracial cd
66%
Becoming an identical twin part I
My name is Cody and I recently turned 19 years old along with my twin sister Cassidy. She is older by 4 minutes and is the apple of our parent's eyes. She is in almost every aspect a goddess. Her beauty, intelligence, humor, sex appeal, and just about any other trait you can think of she is flawless... Read full Story
Chloe6942 2018-08-23 8,001 Teen (18+) Amateur Fetish
94%
Becoming the girl i really am part 2!
I smiled up at my best friend, dressed up in sexy lingerie and smiled, "Can i dress up too?" i asked in a hopeful tone of voice. "Oh, wow, really? Yea sure!" brian answered with excitement in his voice. "Go into the guest room, my sister keeps all her clothes in the dresser ... Read full Story
shemale lover 2014-06-11 5,933 first time shemales cum
78%
The Hottest Of The Teen Transgender Stories
She was a cheerleader in college and I was…well. Me. I lived one of those transgender stories where I was still stuck in the middle of my transition and I wasn’t a girl anymore, but I wasn’t the guy she needed. She had every single guy in the campus she wanted and I had..well. ... Read full Story
shemale lover 2016-06-06 8,756 pussy fingering transgender
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
94%
James's Cum Slut Part 2
It had been a day or two since James had turned me and it had left me craving more! We whiled away the days larking around and being fools, then one morning after I’d had a shower, James had swapped my rooms, from the spare room to his sister’s. He said that most of her stuff would fit and winked, l... Read full Story
ATC97 2015-05-20 4,955 anal Teen (18+) Crossdresser Blowjob cd twink
94%
Jamess Cum Slut part 3
James decided it was time to take me into town for something special. He’d said he’d ordered a few things in and wanted to get me something really nice for a surprise this evening, seen as I’d been such a good girl. I dressed up pretty casually, leggings, a plain red pantie and bra set and and cute ... Read full Story
ATC97 2015-07-15 5,166 Teen (18+) Crossdresser threesome double penetration cd
95%
James's Cum Slut Part 4; Back to Boarding School
It was back to school time and I was back in the boarding house with James. We hadn’t seen each other all summer and were eager to relight the fire. But it was going to be hard. While we shared a dorm together, it would be hard maintaining the privacy. We had both packed items from my secondary ward... Read full Story
ATC97 2015-10-08 7,527 Crossdresser teen cd (18+) cum slut latex ts gangbang sex
95%
"University" Friend
University “Friend” Finally I had earned a little more freedom. I was off out of my sleepy village and at university. I had a small flat in an apartment block all to myself in a nice enough part of town. I unpacked my clothes and settled down for my first quiet night in, but as I put a few of my ... Read full Story
ATC97 2016-06-21 11,939 anal Teen (18+) Crossdresser Lingerie cd
61%
My first I got horny for a guy
This happened when i was 13 and just starting secondary school, our class went to play football in the school hall and after playing for a while we finished and went to the changing rooms. Everyone was getting undressed and putting on clothes and going out the door,some were talking and laughing. Th... Read full Story
Saoirse1973 2017-05-08 5,590 Teen (18+) blonde
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+)
65%
Sucking off a stranger
When I was about 18 I started checking out craigslist in the morning before school while watching porn to help me get off. I would fantasize about meeting the people who posted but I knew I couldn't as most of them wanted to meet while I was in school or lived to far away for someone with out a... Read full Story
I Swallow 2017-09-20 16,590 Teen (18+) cum swallow gay