Sort by
Relevancy

Free Stories

87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 11,236 Stockings anal sex Fetish Interracial sissy
82%
Pandora's Box Chapter 1
I discovered transsexual women completely by accident when I was 18. I was watching one of those Real Sex shows on HBO, and without warning, two women who were showering together for a video shoot turned around and I was shocked when I saw cocks where I expected to see pussies. What probably shocked... Read full Story
shemale lover 2012-08-31 4,635 Cumshot Blowjob transsexual Lingerie condom sex
96%
How I began my crossdresser transformation
Here are the usual disclaimers this story is for adults only if you are viewing this and are not 18 years of age or older please close this page immediately. There is no crossdressing in the story but this is how I began my transformation from regular boy into cock sucking teenage crossdresser.... Read full Story
srlvictoria 2013-04-10 12,584 anal Crossdresser oral handjob sissy
96%
My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
sach 2016-02-16 14,038 first time tranny ass fucking guy on shemale mutual suck
100%
And I Love Cis Girls Too
This is a fantasy I wrote for a cis-gendered woman I met in a chatroom who simply asked me what kind of titties I like. My hope is that reading it might make someone as horny as it made me while writing it. Enjoy. I like your tits. I'll make this as clear as possible. Your breasts are ex... Read full Story
Hardrock51Fifty 2024-05-15 3,446 Amateur Big Tits Cumshot Masturbation Big Cock
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,761 Fetish transformation dildo
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 13,304 Group Sex Cumshot shemale oral
81%
At psychiatrist's office
New Story of my friend......... I nervously tap my foot on the floor as I sit in my psychiatrist's office. The judge ordered me to see a psych as punishment for participation in prostitution. While I feel frustrated at having to meet this person, its either this-or jail, so... Hi Doct... Read full Story
sach 2016-01-02 5,355 ass Big Cock ass fucking domination
85%
Gilding the Lilly
It was a dark and stormy night. Oh, wait, I was taught NEVER to begin a story like that. (Snoopy can get away with it, but he does all his writing with a typewriter balanced on his doghouse). OK, getting back to important things. It was actually early Autumn out in the Desert, cool weather was s... Read full Story
CharlotteSlut 2018-03-02 6,442 Group Sex Shemale Fucks Guy gangbang Shemale and Girl shemale + shemale
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 30,894 Teen (18+)
75%
My first time with a man
I have been dressing on and off for many years. But one time when I was feeling more like a woman I decided to join a site where I could meet men who liked girls like me. I met a wonderful man and we constantly kept in touch with each other since he lived in another state. Well he told me that he wa... Read full Story
AndreaPeters 2018-10-24 6,550 Crossdresser Amateur Blowjob Big Cock Interracial
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 5,672 shemale gangbang facial
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 18,513 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 4,207 anal sex cum oral sex
100%
My First Time Out Part 5
Preface: It is not imperative, but helpful that one reads Parts 1-4 in order to grasp the personalities of characters in this story. WARNING: The following story contains some explicit foul language and IS NOT for reading pleasure of anyone under the age of 18; nor is it permissible to read if yo... Read full Story
shemale lover 2011-10-18 4,956 fingering tgirl handjob
100%
Jamie is taken Part 1
Jamie loved his job. Not only did he enjoy the job itself, but it also provided him with outstanding opportunities when it came to getting laid. Jamie was 21 years old and had moved to the city eighteen months before. Not long after he had gotten the job, working as a sales clerk and tai... Read full Story
shemale lover 2011-11-30 5,540 Fetish bondage extreme exhibition
50%
Old Folks
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
shemale lover 2012-01-10 8,428 transsexuals romance crossdressers
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 5,077 taboo anal sex sucking sperm rimjob
100%
The Club
Pretty soon everyone was naked and in their places and ready to go. "Okay ladies, I'd like you to meet tonight's very special guest, may I present to you, Susi!!!" Missy swung open the door to the adjoining room, and much to the stunned delight of everyone there an incredibly beautiful Asi... Read full Story
shemale lover 2012-05-01 4,396 Group Sex shemale orgasm fingering Sex Toys
50%
The club
"Okay ladies," Missy said to her guests, "relax and get ready because I have a very special treat for today's meeting!" "What is it?" and excited Jayne asked while removing her sweat shirt and jeans. "Now you know better than to than that" Missy replied with a... Read full Story
shemale lover 2012-05-03 5,040 Group Sex Cumshot Ladyboy fingering Sex Toys
100%
Womanhood for Jenny
The muted alarm-clock brought jenny awake instantly. She reached over to shut it off. Being ever so careful not to disturb Master, she slipped out of bed and gazed lovingly at the sleeping man. From their earliest intimacy, He had accepted her completely as a woman, His woman, not a trans-gendered m... Read full Story
shemale lover 2012-10-07 6,320 hardcore Sex Toys tg
94%
Tortured by the T-Girl Tutor
Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... Read full Story
shemale lover 2012-12-18 34,606 Big Tits shemale Big Cock Lingerie domination
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 6,033 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
85%
Horny tranny
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 lo... Read full Story
shemale lover 2013-11-29 5,344 tranny Cumshot suck ass fucking domination deep throat
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 3,330 Stockings Crossdresser Amateur suck Lingerie
77%
Amber part 2
After the night with Hollywood the next day seemed to drag by. As soon as I got back to my room, I quickly stripped. Falling back onto my bed, I slowly masturbated, my mind still reeling from last night. I'd actually sucked cock, not only that, but I liked it, I liked it a lot, and wanted to do ... Read full Story
ambersissy 2021-04-23 3,948 Crossdresser Amateur Blowjob Big Cock Guy Fucks Shemale Interracial
100%
TV television
My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had everythi... Read full Story
shemale lover 2011-12-11 5,653 Fetish trans tv
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 31,724 strapon porn
50%
The Greatest Lie Part 6
In my rare moments of leisure in the weeks following my close encounter with death, I had had little opportunity to talk about it. Of course, the police had asked perfunctory questions, and I had testified at the coroner’s inquest, but until my next appointment with Dr. Erika Wright, I had not... Read full Story
shemale lover 2012-01-19 4,940 hardcore erotic encounters fantastic
66%
Bar Table Fun
Up to Miss Kate's door i walked, then knocked on the door happily. i hadn't been to Mistress's home for a couple weeks, and was thrilled to finally be back to see Her. She opened the door and smiled at me, i smiled back and lowered my eyes. "Come in sissy", She ordered. i quickly scampe... Read full Story
shemale lover 2012-02-11 3,018 Fetish oral sissy
76%
Porn Princess
They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... Read full Story
shemale lover 2012-09-02 24,562 Cumshot Blowjob fuck fingering big boobs
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,491 Fetish crossdressing feminization
89%
The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
Tvtrinity 2021-04-07 22,315 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
100%
My Afternoon With Venus - Part I
It was a stunningly bright and clear Saturday morning when I left my house to head out and run some errands. Nothing big, just little odds-and-ends that had been building up that I needed to deal with someday and it seemed like this was as good a day as any ... little did I know how good the day wou... Read full Story
funpics 2018-03-23 13,601 Amateur Shemale Fucks Guy Asian Guy Fucks Shemale Homemade
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 7,625 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
0%
Giving my first blowjob
I was recalling the first time that I ever gave a blow job while I was jerking off last night. I thought I would tell you the story and share what my experience was like when I finally took the plunge and made my first attempts at having sex with a man. At the time, it was a little awkward, but the ... Read full Story
SissyAnalPrincess 2021-05-11 5,313 Amateur Blowjob Danni Cherie
93%
Homework
Daniel was a 15 year old teenager, like any boy his age, he was full of hormones and sexual fantasies for every pretty girl that passed in front of him. In the last weeks of the school year, the history teacher had a child and was absent from school, being replaced by teacher Marlene, a trans woman.... Read full Story
haroldãosanguebom 2024-01-09 7,997 Shemale Fucks Guy Big Cock Mature
89%
Cast party
My name is Dan, and I have always considered myself an adventurous and open minded person, but my experience was taken to a whole new level in my junior year of college when I got involved in an amateur theatre group. We all got along astoundingly well and I found myself becoming friends with severa... Read full Story
shemale lover 2015-06-13 15,467 shemales gay male Group Sex
94%
Trans Bookstore Adventure
I was walking near the corner of Polk and Post Streets past an adult bookstore when I noticed an attractive transgender standing on the corner. I walked up and struck up a conversation. I told her she was attractive. She asked me if I wanted a date. I asked her if she was functional. Then I asked he... Read full Story
shemale lover 2011-08-11 4,802 asshole Blowjob dickgirl
100%
Shemale on wheels tour
Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of... Read full Story
shemale lover 2012-05-17 3,974 anal sex fingering domination oral sex facefucking
72%
First Time Sissy Maid
I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... Read full Story
shemale lover 2012-10-27 17,522 first time Fetish Big Cock domination sissy
89%
My first shemale experience
So before I was even into the porn I had my first experience. I was 25 years old and never thought about anything like this till it happened. I was out with my friends one night hitting the usual bars on the weekend when this hot young woman caught my eye. I was feeling pretty brave due to my "... Read full Story
Duke04 2017-03-28 54,038 first time Amateur Cumshot Shemale Fucks Guy hot shemale
87%
house party
t was another house party of Greg’s. There was about 15 to 20 people there. I though nobody knew about our gay relationship, did not think Greg wanted this to be public knowledge because of his standing around the community. The party was heterosexual couples, some making out, but mostly talking... Read full Story
cd4fun715 2019-01-08 3,511 Amateur
100%
My first time having sex with a Tranny
I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... Read full Story
Joe22lovests 2021-09-15 12,476 first time Shemale Fucks Guy Blowjob Big Cock
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 7,701 anal Shemale Fucks Guy Big Cock Frottage
75%
Encyclopedia Erotica By The Fan
It was a normal-looking enough place. A small town in California. Looking at it, no one would ever guess it sat on the hellmouth. The Mouth of Hell. A portal to a multitude of dimensions filled with horrors and wonders. Many things came to the Hellmouth, drawn by its power. Vampires. Demons. Mon... Read full Story
shemale lover 2011-10-19 4,863 asshole orgy Sex Toys
100%
The Greatest Lie Part 3
My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... Read full Story
shemale lover 2012-01-19 4,686 hardcore crossdressing erotic encounters
100%
The Greatest Lie Part 4
Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... Read full Story
shemale lover 2012-01-19 5,091 taboo femdom crossdressing
100%
The Greatest Lie Part 9
Two hours after saying goodbye to Rick and Randy, Tran and I left Minneapolis and boarded a plane to LA. I fell asleep at take off, and woke as the plane began its descent. Tran was staring out the window at the city’s lights spread in an endless shimmering galaxy below. "Wow, I love LA a... Read full Story
shemale lover 2012-01-19 4,226 hardcore erotic encounters fantastic
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 9,001 anal sex Creampie Fetish gangbang crossdressing
100%
The Football Jock and Chrissie
Back in college, sharing an apartment with my BFF/roommate Kelly, a lot of my dates and hook-ups were arranged by Kelly. For some reason she always seemed to know just who was into what when it came to sex. She learned a lot about other people’s likes and dislikes from hanging with her lesbian... Read full Story
shemale lover 2012-07-13 4,029 Cumshot transformation oral sex
100%
First Time S & M Whore
Suellen certainly looked the part of a cheap S & M whore: black seamed hose, shiny pink patent 5 inch heels, a black leather miniskirt, and a translucent white nylon blouse that clearly showed the black bra underneath. Her long blonde hair swayed seductively and naturally. Well the hair was natu... Read full Story
shemale lover 2012-10-24 5,570 Cumshot oral condom sex
95%
Hot for Teacher
Jack was enjoying his going away celebration, as he prepared to move from teaching high school to college. He had spoken with many of his former students, and found it endearing that so many of them cared enough to show up at the party. By the end of the evening, though, there was still one young wo... Read full Story
shemale lover 2013-01-05 17,034 sucking Blowjob Big Cock handjob
70%
I meet my new Mistress for the first time
I was feeling excited about and looking forward to Friday night. The reason for this was that I intended to dress up as my alter ego, Tania Harvey, and to go for a night out to a club nearby that is popular with TG’s, TV’s and other like minded people. I took a lot of care and attention over the way... Read full Story
Tania Harvey 2017-06-26 8,567 Amateur gangbang 3some shemale on shemale dominating
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 9,656 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
33%
Chance Encounter Part 3/7
We were passionatley kissing each other for a while and slowly but surely I could feel her wonderfull cock grow hard again………. I told her how good her cock felt and we continued kissing but now she was rhythmically sliding her cock over mine while we kissed. Her luscious balls felt rock hard as w... Read full Story
Katlick 2019-10-21 5,475 Small Tits Bareback Blowjob Big Cock