Sort by
Relevancy

Free Stories

92%
How it all started!
Hello to everyone who’s reading my story. Before I start I would like to introduce my self and tell you few things about me. My name is Ria Sweet I’m 31 years old and I’m from USA. I was adopted when I was only few months old and I never met my biological parents. The story I’m would like... Read full Story
Ria Sweet 2022-08-24 6,625 Teen (18+) Small Tits Crossdresser Amateur bikini skinny sundress
92%
A Sissys new start
I only ever told my father one lie. That was about the boots. I was about to turn 18, jobless, directionless and pretty screwed up to be honest. There had been rows, fights, shouting matches and long frustated silences about what i was doing with my life, but i had formulated a plan. Kind of. Tw... Read full Story
SissyDani31 2018-10-04 5,375 Teen (18+) Crossdresser Amateur
93%
Sissy Experience - Episode 1: The Beginning
Hello All, Hope you’re all doing well!! This story narrates the beginning of my crossdressing and sissy adventures. Before I begin I’ll tell you somethings about my family. We are a family of four consisting of me, mom, dad and an elder sister. I am currently 20 years old and in college. My da... Read full Story
brownsissyboi 2020-05-15 7,832 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
100%
Finally, a Vacation!!
My life has changed so much in the last 2 decades! When I discovered the existence of the trans gender, I was so excited that my life changed immeasurably for the better. I knew what I liked better than anything else. From not knowing trans folks existed, I went to running into them all the time. ... Read full Story
GirlyArms 2021-05-20 3,216 Blowjob trans skinny small dicks sexy arms
100%
My First Time Out: The Preparation
Shane, a 24 year old blue-eyed, blonde-haired salesman boarded the airplane enroute to beautiful downtown Salt Lake City, Utah. He had made the trip many times. He always conducted his business in a timely fashion so he could get back to his office making sure not to miss any other business opportun... Read full Story
shemale lover 2011-10-17 3,684 first time Lingerie skinny
100%
Smooth Sensation
God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street London on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipat... Read full Story
shemale lover 2012-04-08 3,103 anal Creampie oral transvestite skinny
90%
Shemale Charlotte caught wanking in the bath
Charlotte is a very small 18 year old, very skinny, only just 5 foot but has an amazing pair of breasts which stretching the skin makes them show veins all over. Her pale skin showing the veins even more. Charlotte is also a shemale, her small size and large breasts she also has a very large 8inch (... Read full Story
shemale lover 2013-06-18 6,803 Amateur Cumshot Masturbation jerking Shemale and Girl
33%
Sleazy Walking
I was bored one night, and began to email wanted ads on craigslist to see who was hosting in my area. I lived in spokane, wa at the time in the east central area, sorta behind the fred meyer. This night was boring, my friends had left a while ago with their girl friends, jealousy began to set in. I ... Read full Story
Ville Lohner 2014-05-15 2,699 Stockings Crossdresser Amateur suck Lingerie
78%
Cara's First Time
Cara's First Time This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in... Read full Story
Emma W 2017-07-05 29,800 Crossdresser Amateur Bareback
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 6,786 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
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 7,274 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
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 8,686 Crossdresser Amateur Creampie Homemade cum in mouth webcams
87%
A Virgin Crossdresser
I was newly turned 18 never even kissed a girl let alone had sex. I had been crossdressing for about a year and had stumbled upon a site called tvchix which where I spent my nights in chat looking and getting an insight into what this world could offer. Bit of background I had named my alter eg... Read full Story
Jessicaxx91 2020-02-06 11,649 Crossdresser Amateur Fetish Lingerie Guy Fucks Shemale cum in mouth
58%
A story :)
Skirts and bikinis feel so nice against my skin, especially my cock. It feels so nice to have a hard cock in tight clothes; it just feels natural to me. Anyway, there was this kid in my grade who I had always had a crush on. Timmy was his name. He was skinny and not very muscular, but was very at... Read full Story
AndreeaLuv 2020-03-31 4,139 Crossdresser Amateur
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 6,965 Crossdresser Amateur Bareback
71%
Shy Marcy
After becoming acclimated to my new friends and their life choices, My friend Sammi noticed a girl in "our" restaurant that always sat alone and made no eye contact. We all discussed her and everyone determined that someone should approach her and make her comfortable. One guess who was elected... ... Read full Story
GirlyArms 2021-02-22 2,405 Group Sex Fetish Blowjob transgender skinny shy big load muscles
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 3,471 Crossdresser solo Amateur Cumshot Lingerie Sex Toys Homemade pov webcams
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 2,543 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
Sissy Ava 2022-10-11 7,503 Stockings Crossdresser Amateur Bareback Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,341 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
50%
DEVENIR CASSIE
L'argent était difficile à trouver dans notre foyer. Être l'aînée de quatre enfants et ma mère étant une mère célibataire mettent nos ressources à rude épreuve. Nous avons rarement eu de l'argent supplémentaire dans notre famille à dépenser pour des choses comme manger au restaurant ou aller au ciné... Read full Story
Femboy 2021 2023-01-20 1,198 Stockings Crossdresser Amateur Cumshot Fetish Blowjob Big Cock Lingerie domination
50%
SISSY FOR MOMMY'S NIPPLE CREAM
Les chances de Jim de mener une vie normale ont été anéanties avant même sa naissance lorsque son père est décédé dans un accident de voiture. Sa mère, Julia, a fait de son mieux pour l'élever seule, mais elle savait qu'elle ne pourrait jamais être la mère et le père de son précieux Jimmy. Pourtant,... Read full Story
Femboy 2021 2023-01-20 963 Stockings Crossdresser Amateur Big Tits Fetish Blowjob Big Cock Lingerie domination
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 4,732 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
84%
Meeting and Eating Sammi
Meeting and eating Sammi I was the new guy in town. I frequented a local bar/restaurant and noticed a happy group of folks were there quite often. I guess I was noticed too when a VERY attractive young lady approached me and said "Hi. New in town?". We spoke for a while and I noticed that ... Read full Story
GirlyArms 2021-01-22 2,740 Fetish Blowjob handjob skinny surprise dick
60%
Winsome Morgan
I’m not generally one for parties, but my very good friend Josie invited me to her open house to celebrate her new home. It’s quite lovely, and has a nice veranda to a deck to an in ground swimming pool. From the living room there are sliding doors that take you out to the pool. To the right is th... Read full Story
lissomlover 2020-09-02 3,792 Small Tits lesbian skinny
87%
Amateur Shemale Videos Just Next Door
I rented out a place in this neighborhood not because of the fabulous location but because it was really cheap. It wasn’t what you call a family neighborhood, but nobody was picking on me, at least. My flat didn’t have much of a view. The living room window was facing the building nex... Read full Story
shemale lover 2016-04-12 7,772 Cumshot suck Creampie
0%
I live once
Hi there! -& Welcome to my profile, here are some funfacts4you I'm young, nice & willing..> Which means I'm looking for experiences + new things and this i want to share with you all of you'guys out there.. But i would; like/preferably be as an anonymous sexy superhero male for all those... Read full Story
Movie2do 2022-08-09 2,896 Teen (18+) Amateur me seeking exposure Application job in porn Seeking anyone corius
100%
Cross dressing Aunt
CD Aunt Well, my uncle was a crossdresser, but the group is Aunt CD, so it is all kind of confusing. Back in the mid 80's I was fresh out of high school and was offered to spend the Summer with my uncle in TX, he was only 10 years older than I and was offering to let me stay with him so I could work... Read full Story
PARUSHFAN 2023-06-14 6,254 anal Crossdresser Amateur Creampie Blowjob sissy cum in mouth
80%
Physical exam that embarrassed the fuck out of me.
Hello and welcome. My names safebet1980 aka Dug if you want a easter name to remember lol.. Right about now some of you are saying to your selfs that name sounds familiar and it might. If your looking at porn I'm on a lot of sites both as a user and a uploader of Amateur videos I both shot and sta... Read full Story
safebet1980 2022-10-11 4,423 Amateur Homemade
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 4,038 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Seducing the Delivery Man
Angela sat on her couch in her living room sipping on a glass of wine and tried not to cry. What a shitty birthday. Her best friend, Kathy, who happened to be a co-worker of her boyfriend John, sent her an interesting picture of him a couple of days ago. Apparently, their office had thrown a retirem... Read full Story
JohnSorenson 2024-01-12 6,100 anal Amateur Blowjob Guy Fucks Shemale cum in mouth
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 13,656 first time sucking fuck domination
75%
Experimenting with Cock
I was 22 and at the time did not have a girlfriend. I had a habit of jerking off at least once a day if not more. Starting masturbation at an early age made me bored by "normal" porn star videos. Leading me to amateur porn. Soon that became boring and I was experimenting with everything. O... Read full Story
shemale lover 2011-12-01 4,622 gay male oral
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 9,667 Stockings Big Tits fucking foot fetish
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,411 anal Cumshot shemale oral
75%
My First Time Out Part 1
Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms w... Read full Story
shemale lover 2011-10-17 4,173 first time cum oral
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 5,207 anal oral handjob
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,077 torture extreme fiction bondage and discipline
100%
A Special Girl
Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the sm... Read full Story
shemale lover 2012-06-30 5,228 Cumshot Blowjob oral sex
87%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 66,847 Fetish shemale oral feminization
100%
Fun Times at Halloween
It was almost Halloween and I was stumped for a costume. I was excited, tonight was the annual Delta Kappa Halloween Bash, the biggest fraternity party of the year. All the Greeks got dressed up for this party, even those not in DK. I headed down to my friend Kathy's room to see if she could help... Read full Story
shemale lover 2012-12-08 5,073 Fetish oral crossdressing
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,328 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
80%
JUERA MARICON
My name is Keven Jeanne and, Yes, I am a Sissy! When I was 13 I put on my mom's panties and some of her lipstick when she was at work. I had longish blonde hair and I ruffled it up - kind of teased it up - and when I looked in her dresser mirror, I almost ejaculated. Because what I saw looking ... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,097 blonde shemale submissive cocksucking
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,142 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
50%
SISSY AWAKENING
- Trou de gloire du sex-shop - "Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleu... Read full Story
Femboy 2021 2023-02-17 1,000 Stockings Crossdresser Outdoor Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
50%
SISSY AWAKENING ⚧️ ⚧️
"Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleure amie et une femme que je connai... Read full Story
Femboy 2021 2023-03-25 828 Stockings Blowjob Uniform Lingerie Sex Toys gloryhole cum in mouth cage chastity feminisation forcé maitresse épouse sexe anal
100%
COMMENT NATHAN EST DEVENU NATALIE ⚧️ ⚧️
Je m'appelle Natalie mais ce n'est pas le nom avec lequel je suis née; c'est plutôt le nom que ma femme m'a donné quand elle a fait de moi sa "sœur" et sa poule mouillée cocu peu de temps après notre mariage. Mon vrai nom est Nathan mais c'est un nom que je préférerais ne plus jamais utiliser parce ... Read full Story
Femboy 2021 2023-04-23 1,248 Teen (18+) Blowjob Lingerie Sex Toys small cock sissy cum in mouth sissify poule mouillée et fille premiere foi
80%
THE TRUTH ABOUT "DOES SIZE MATTER"
In the Black Community we all grew up overhearing women talk about dick size. You hear things like Short skinny men have the biggest dicks, or Tall skinny men have the longest dicks. You hear things like Big guys have the girthiest dicks, & Fat guys have the smallest dicks. Right now I have one o... Read full Story
WHORNYBUHNZ 2023-05-15 5,221 anal Big Cock Ebony
100%
The Only Difference is the 'S'
I agreed to do the late shift because it suited me. My wife had run off with a neighbour, leaving me with a pile of bills to pay, and as a result all I was doing in the evenings was mooching about watching the television and seeing off cans of lager. So the chance to start work at four and finish at... Read full Story
shemale lover 2011-11-14 5,643 sucking fingering climax
50%
The Greatest Lie Part 1
The greatest lie that they tell you is that what happens in high school doesn't really matter: that life begins in college. I pretended to agree, though I never believed it. For as you will see, I am the world's greatest liar. "Take Sadie Hawkins Day, for example," I said to my buddy Qu... Read full Story
shemale lover 2012-01-18 6,757 taboo hardcore crossdressing
0%
Mike and Chris Together
Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately. "I'm really sorry, Mike. I've had some great times with you, and I will alw... Read full Story
shemale lover 2012-02-07 4,955 anal sex Creampie Shemale Fucks Guy Guy Fucks Shemale
100%
After Church
I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they were... Read full Story
shemale lover 2012-08-19 5,851 Teen (18+) Fetish oral sex crossdressing
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 10,329 Masturbation Blowjob blonde ass fucking big boobs
100%
Proud To Be A Sissy Chapter 1
I had just turned eighteen and only had two months of high school left. My marks were good and already had a possible placement in a university where I hoped to get a new start. I was so looking forward to getting away from all the shit that life had forced on me in this little hick town. Usuall... Read full Story
shemale lover 2012-12-23 11,634 Stockings Crossdresser Big Cock ass fucking ass licking
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 16,968 Crossdresser sucking Big Cock ass licking big boobs
85%
Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
shemale lover 2014-09-17 60,528 suck Bareback Asian Ladyboy ass fucking