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 10,620 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
88%
Who's She?
School had been a bore for Tony. He was a bright lad and didn't have to work too hard to get through classes unnoticed by the teachers and class mates. He had plenty of friends but no one close. He didn't excel in sports or academically. He had picked up a few good exam results but had decided that ... Read full Story
Vinny_A 2019-07-08 11,946 Teen (18+) Crossdresser Amateur Big Tits Bareback Blowjob Lingerie
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 7,153 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
80%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 5,127 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
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 14,483 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 12,255 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
100%
First fuck in public ;)
You’re only wearing a coat, I find a place where, I can kiss you then slide my hand between the flaps of your coat. I expose your breasts and slide my hand down across your tummy down to your pussy. My fingers start to explore your soft bush, working there way to your soft pink lips surrounding your... Read full Story
BalkanLoco91Ri 2019-08-26 4,120 Stockings Teen (18+) Amateur Big Tits Cumshot Outdoor Masturbation Bareback Creampie Blowjob Big Cock Uniform domination Homemade pov cum in mouth
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 10,205 Stockings Big Tits fucking foot fetish
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,729 Big Tits sucking ass licking fucking
100%
Shemale fantasy with female squirting
I just finished my mornig coffee at the breakfast bar in the kitchen when the door beel rung. My wife opened the doo and it was one of her hot friends. She invited her to sit at the bar beside me and serve her a coffee. Right before she gives her the coffe she slips something into the brew. Her ... Read full Story
TRTRAIN 2023-05-21 3,842 anal Stockings Amateur Big Tits Big Cock Lingerie Shemale and Girl pantyhose Mature Homemade Ass to Mouth cum in mouth shemale fucks female
66%
A different couple
I am Hans, as I already mentioned in my previous story, I am a mature guy (47 years old) who came to the Island of Tenerife more than two decades ago. I am a drinker, a womanizer and a gambler. In these more than 20 years I have seen them in all colors. I have made a lot of money and lost as much, I... Read full Story
lkusex 2021-03-08 5,926 Amateur Big Tits domination
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 6,398 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
50%
Feriengruss 18.07.24
Um ähnliches, wie im folgenden Bericht, mit mir zu erleben, ist es notwendig, dass man sich sehr gut kennt. Alle Handlungen sind miteinander abgesprochen und es ist beidseitig ein tiefes Vertrauen vorhanden. Nicht nur, dass mir nichts passiert, auch dass ich meine Grenzen während des Spiels klar kom... Read full Story
Cheryl_F 2024-09-03 267 anal Small Tits Amateur Cumshot Bareback Creampie Fetish blonde Big Cock Ladyboy Shemale and Girl Sex Toys small cock
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 5,637 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
50%
La bonne chair masculine…
La bonne chair masculine… La brise caressait mes mamelons gonflés me donnant des frissons agréables. Les deux verres de Riesling avaient également contribué à mon excitation. Mon entre-jambe brûlait comme si le soleil qui disparaissait avait soufflé toute son énergie thermique dans mon intérieur... Read full Story
hippocampus_171 2023-04-23 1,242 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminization cum in mouth gaycd virile
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 4,276 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%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 5,285 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 5,031 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
the orgiastic fever of a trans-milf
Simulating a woman, or the orgiastic fever of a trans-milf It's been two months since I moved to the megapolis, where I've discovered several places where the third gender goes. One of my first explorations was a huge lingerie shop in a MALL; I wanted to buy some sexy stuff without being noticed ... Read full Story
hippocampus_171 2024-09-04 2,287 anal Amateur Cumshot Creampie Shemale Fucks Guy Latex Sex Toys Mature small cock
83%
Las Vegas Swingers
It had been over 6 months since I seriously dated someone, and I was getting depressed and in a rut. I had directed my attention to my work and it kept me from feeling sad about my loss of someone I almost married. I had met a transsexual girl that absolutely adored, but she was tragically killed. (... Read full Story
Jon Paul 2018-06-11 10,493 Amateur Guy Fucks Shemale Mature Ass to Mouth cum in mouth double anal shemale + shemale
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,639 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
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 14,373 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
90%
A pervy uncle invited me to his house at 10 PM..!
It's been 8-10 years now, I had this amazing experience. I was standing at the bus stop in my area/street(my daily routine), one uncle was watching me but I ignored eye contact as I feel awkward the way he was looking at me because I act straight in public and I felt that he's seen my girly ... Read full Story
Cindy Sky 2021-07-20 7,527 Teen (18+) Small Tits Amateur Cumshot Outdoor Bareback Creampie Fetish Blowjob Asian Ladyboy Mature
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,703 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
91%
My Seductive Secret (True Story)
During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... Read full Story
LovelyLeo97 2019-06-18 14,425 Stockings Teen (18+) Small Tits Crossdresser Cumshot Outdoor Masturbation Bareback Fetish Blowjob Big Cock Lingerie domination Sex Toys Homemade cum in mouth
100%
Mein erster Blowjob
Nun hat es endlich mal geklappt. Ich schrieb längere Zeit mit einer anderen Sissy und lernten uns immer besser kennen. Nach mehreren vergeblichen Versuchen sich mal live zu treffen, hat es dann endlich geklappt. Wir trafen uns auf einem Parkplatz. Ich hatte bereits einen heißen String, Strapse und e... Read full Story
Maja 2023-07-04 1,799 Stockings Small Tits Crossdresser Amateur Outdoor Blowjob Big Cock Lingerie Homemade sissy
100%
Feriengruss 20.07.24
Erneut ging es Outdoor, dieses Mal aber an die Thur zum FKK Baden. Nicht am bekannten Platz in Bischofszell, sondern an meinen geheimen Platz, zwischen Kradolf und Bischofszell, unterhalb von Halden. Ich habe erneut mit 5 verschiedenen Herren abgemacht, die mir in gut geplantem, zeitlichem Abstand... Read full Story
Cheryl_F 2024-09-03 249 anal Small Tits Amateur Cumshot Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy pov Ass to Mouth
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 6,198 anal Cumshot Ladyboy oral
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,324 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
I Love To Love You
I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... Read full Story
Brina Giselle 2023-09-24 5,378 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,662 Teen (18+)
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 3,792 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Tasting the good FLESH
I am no longer Virgin, en bon et du forme Thing never dared since I taste the enjoyment by all the senses and in all its senses... I discovered her when she smiled at me as a thank-you for giving her the way to the small-town supermarket where I was on business. Sandals at her feet of Cinderell... Read full Story
hippocampus_171 2022-11-10 5,099 Amateur Creampie Shemale Fucks Guy Guy Fucks Shemale Mature Ass to Mouth cum in mouth
100%
Unexpected Twist
I'm a reporter for a regional newspaper in Germany, in my 30's and always in search of a good story. Last summer, while visiting a local pride festival for a short report, I got in contact with the regional queer community. A few months before, a new editor-in-chief took over in our office, a very c... Read full Story
webandy87 2023-11-22 7,333 Small Tits Amateur Masturbation sucking Blowjob blonde Homemade femboy young ts
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 13,506 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,509 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
100%
David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
shemale lover 2012-07-30 6,008 anal sex Cumshot oral sex rimjob
92%
A very special lady
I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and wil... Read full Story
shemale lover 2013-07-18 6,324 Stockings anal sex Shemale Fucks Guy ass licking ass fingering
66%
a day in the life of Amber SissyZofen 264
And the days had passed one after the other and now it was the day of my date. He sent me a txt at 8.30 on Saturday morning to say he was coming And you remember he was leaving his phone at home in case his wife called You know I had sent him my address, parking advice and left the gate ajar. ... Read full Story
amberdoll 2020-09-15 2,959 Stockings Small Tits Crossdresser Amateur Masturbation Bareback Creampie blonde Lingerie Homemade cum in mouth
50%
champignons sous toutes ses formes et façons
La saison des champignons est ouverte! Miam... J'adore les champignons, sous toutes ses formes et façons. Nous sommes une quinzaine d'amateurs qui se retrouvent uniquement à l'occasion des ceuillettes de champignons sans aucun autre rassemblement amical! Pour cette dernière sortie de la saison,... Read full Story
hippocampus_171 2023-11-24 816 anal Small Tits Amateur Masturbation Mature small cock big ass bisexual Homemade cum in mouth bald
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,865 Masturbation Blowjob blonde ass fucking big boobs
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 5,172 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
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 6,981 anal Crossdresser Blowjob heels cum in mouth pink dress
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 4,451 anal Crossdresser Outdoor Blowjob cum in mouth teen (18+)
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 9,215 Stockings sucking domination
73%
Vegas Baby: Swinging for the Fences
"Hello," Miss K said as she answered the phone. "Where are ya? You're gonna be here in 5? Alright. You got the address for IHOP, right? OK, See ya in a bit. Bye." "So is this girlfriend of yours on her way?" Jennifer chimed in. "I mean if she doesn't exist, this... Read full Story
shemale lover 2011-11-15 5,642 anal oral handjob
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,593 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 10,751 orgasm facial oral sex
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 14,243 first time sucking fuck domination
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,409 strapon porn
100%
The game show,
One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... Read full Story
chris1989r 2022-01-24 5,119 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
100%
The Bounty Hunter - Working With A Partner
My boss, Carl Bronson, was pleased with the results of my first case, and gave me more jobs over the next few months. In each, I learned from my mistakes and was able to apprehend my target. Even better, I was finally earning some good money and doing something that was worthwhile and, more importan... Read full Story
shemale lover 2012-01-29 4,635 sucking Creampie cum fucking