Sort by
Relevancy

Free Stories

87%
THE ATTIC NOVEMBER 7
THE ATTIC NOVEMBER 7 – PART 1 THE JOURNEY AND GETTING READY. Susan had not had the opportunity to make the journey to the Attic dolled up to the nines so she made do with just wearing her black and pink lingerie under the hideous drab stuff (yuck). Having arrived early and parked up, she relaxed ... Read full Story
sexysusang 2018-03-09 5,813 Amateur Group Sex Bareback Blowjob Guy Fucks Shemale cum in mouth
80%
A New Spin On Role Playing Games
A New Spin on Role Playing Games By: Shawna Summers shawnavinylltv@gmail.com I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to rol... Read full Story
shawnavinyltv 2018-06-14 10,614 Crossdresser anal sex Blowjob gangbang Lingerie bondage
100%
Lady In The House Ch. 04
A story by MicheleNylons ( Prisoner's transformation continues.) From Part III Steve's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Steve ... Read full Story
✘Transensual✘ 2019-02-25 3,845 Crossdresser prison sex Prison Bitch
100%
Lady In The House Ch. 07
A story by MicheleNylons (Carmel and Charlotte want theirs.) From Part VI "You look gorgeous Michele," Carmel whispers through the bars. I wondered if she had read my mind when I was standing in front of the mirror admiring myself. "Well, I have to say you girls are looking something spe... Read full Story
✘Transensual✘ 2019-02-25 3,274 Crossdresser domination prisoner shemale lesbians Prison Bitch
100%
Lady In The House Ch. 08
A story by MicheleNylons (Crossdresser must comply with jailhouse heavy.) "You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by... Read full Story
✘Transensual✘ 2019-02-25 5,640 Crossdresser domination PRISON PUNK prison sex Prison Bitch
100%
Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
✘Transensual✘ 2019-02-27 5,725 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
75%
Lady In The House Ch. 13
A story by MicheleNylons ( Transvestite prison prostitute gets a visit from the Warden. ) I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance bu... Read full Story
✘Transensual✘ 2019-02-27 5,300 Crossdresser domination PRISON FUCKBOY PRISON PUNK prisoner prison sex Prison Bitch
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 7,711 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,232 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
Caught Dressed
Caught Dressed by Jordan Skythe Chapter One He turned in fright as the bedroom door opened, and frantically pulled his comforter off the bed as Bradley entered. “That was locked!” Brad straightened and smiled. “Woah! Hi!” “What the hell!” Brad motioned to the door frame. “You do know there’s... Read full Story
AuthorJordanSkythe 2022-01-20 3,501 Stockings Crossdresser Bareback Blowjob Uniform Lingerie
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 8,698 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
100%
Chapter 1 - My Cuckold Life
I have a small penis. In fact, I have a very small penis. I’ve been in permanent chastity for over 7 years. My wife and her lovers call it my “caged clitty” and that’s about right as far as it being a useful penis. I suppose I should start at the beginning. I’ve never been much of a man. I’m ... Read full Story
Sissy Annabelle 2022-08-23 5,984 Crossdresser Interracial sissy chastity Cuckold Husband
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 3,920 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 4,716 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
85%
TV Times
One evening I was online when someone wanted to start a chat with me. It was a bi guy who enjoyed cross dressing and having viewed his online profile I said "Hi" and we got to talking. He was married guy named Mike and he had a very understanding wife who allowed him to meet men and a... Read full Story
bigtranslover 2013-12-09 6,070 anal first time shemales
91%
Gay Roommate crossdress
I have been cross-dressing since I was 7, always been a bit in the closet about my homosexuality and cross-dressing but I have always loved it and kept it close. I had one roommate when I was living in Boston his name was James. he was a pretty good looking guy who seemed to always be doing well ... Read full Story
bigtranslover 2013-12-15 9,642 shemales gay male
98%
Shemale Delight
I have always considered myself a, women only, kind of guy. After an experience I had 10 years ago, I have added shemales to my list. Anyway, I love to take road trips and visit different cities, usually out of state. I go on-line to do some research about different cities to see what kind of si... Read full Story
bigtranslover 2013-12-27 10,868 licking sucking pussy
85%
Would You Like To Be My Neighbor ?
I first met Robert when his wife and him bought the house across the street and moved their family in. A very nice and quiet couple that seemed to keep to themselves for the most part. One early spring day I was out in the garage working on a project while my wife and son were away visiting some ... Read full Story
bigtranslover 2014-01-03 10,782 shemales Fetish
33%
Don't mess with Mistress Toni.
Few months ago a guy contacted me online and asked if I did S&M. with a Tgirl. Have done it before (Well very little I haven't done) and said "sure" I asked if he had done this sort of thing before and he said "Yes and I want you to do it "full on" Kept chatting away... Read full Story
bigtranslover 2014-01-21 4,871 shemales Fetish bdsm
78%
First Time Having Sex With A Shemale
Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... Read full Story
bigtranslover 2011-05-21 14,874 first time shemales interracial sex
77%
Changes
A story about a mysterious change and how it changed the life of two people forever. The sunlight practically burned my eyes as I slowly woke up. I blinked several times and closed them again for a moment. I felt like crap, way worse than I should have. Last night the guys and I had gone to the bar... Read full Story
bigtranslover 2014-02-11 5,922 female transformation
52%
An Office Party I'll never forget
I've worked for a large insurance firm for twelve years.I`m their top salesman, every year -salesman of the year. Am I cocky... you bet.I`m the best salesman, and everyone in the office is lucky to have me there. Now the ladies there always look so fine, and I get my share of skirt with most of them... Read full Story
bigtranslover 2014-02-15 7,290 transsexual sex change
88%
Strip Gaming gets with Kelly
After taking an extremely boring Christian ethics class (required by my college, not by choice) on a late Friday afternoon, I checked my cell to see I had a few messages. It was Kelly and she was celebrating a well deserved A on an Calculus test. The first message read: "Got an A in Calc. Vo... Read full Story
shemale lover 2014-02-27 5,682 anal shemales hardcore
100%
Stacy
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2014-03-25 6,159 shemales taboo
80%
Growing up wrong
Hello my name is Krystal, but everyone calls me Krissy. I'm 25 & live in the Detroit area. I work at a local hospital as a Physicians assist & I love it! I'm pretty much a doctor but limited at meds I can proscribe & I don't have to have malpractice insurance. Last night was my third ... Read full Story
shemale lover 2014-03-31 8,129 shemales taboo gay male
94%
Shock and Awe
My name is Frank and I’m a decent looking Irishman in my mid 40’s. Every now and then my work takes me to London for a few days and I like to let my hair down if I can. I try and find a hotel in the Earls Court area so if the mood takes me I can visit one of the many hookers that has apa... Read full Story
shemale lover 2014-05-15 6,314 shemale caressing
94%
My first ass fuck! From Anita
Hi! My name is Anita, I live my life always wearing lace and satin. I have always loved the way those materials feel against my soft skin. I have long red hair and bright green eyes. My friends used to call me Charles but about 12 years ago I had this epiphany of feeling that being a woman was just ... Read full Story
shemale lover 2014-05-23 9,329 Blowjob shemale cumming
80%
Trance club
It was the worst day in my life. My girlfriend Ally and I had been quarreling and rowing for several weeks, we were on the verge of breaking up. I just wanted her to be happy. I lived my life for her. I guess I stood no chance to make her smile at me again. We broke up. Ally said everything was chan... Read full Story
shemale lover 2014-05-25 7,779 sucking shemale
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 5,463 first time shemales cum
92%
Shopping
As I walked through the shop my heart raced. I was here for one reason. To buy women’s lingerie. I had always chickened out at the last second and was determined to go through with it today. I slowly made my way into the small shop browsing over nothing in particular when a older good looking ... Read full Story
shemale lover 2014-06-13 5,321 shemales gay male sucking
86%
Two hot CD lesbian sluts share an intimate moment
Her name was Kelly, we had met online in one of the gay chat rooms I like to frequent and for the next couple of weeks we had developed a friendship, exchanged pics and fantasies and I was really, really into her. we had a lot in common, more than just the mere fact that we were both gay CD’s ... Read full Story
shemale lover 2014-06-21 4,509 shemale cum oral
86%
Bar Hopping with my sisters
My two older sisters asked me to go to the bar with them which is always cool considering i am Transexual and they are not, course i always felt the reason they always asked me to go with them is because i had a way of drawing men to our table like bears to honey ha ha ha.(not that i think i'm all t... Read full Story
shemale lover 2014-06-23 6,615 anal shemales voyeur
100%
Little cock convention
They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... Read full Story
shemale lover 2014-07-07 6,875 shemales hardcore sex humor
91%
First Meeting with Couple
Hi everyone, I actually went through with it and got together with the couple from the fetish party to experience my first sex and scene in real life. It didn't go as i had dreamed of; but, thinking that it would go like that was pretty naive on my part. To start with, i Must tell how cute I l... Read full Story
shemale lover 2014-08-13 5,188 first time shemales bdsm
95%
A Trip to the Beach
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2014-10-19 5,316 shemale oral
88%
Brief Encounter
On the way back from Sidcup one evening last Summer I was busting for a piss. Getting near Croydon, I was looking for either a toilet or a wooded area. They seem to be closing all the toilets down nowadays. Just as I was near the stage of wetting myself, I noticed a sort of drive-in between bushes s... Read full Story
shemale lover 2014-11-03 5,596 Cumshot sucking fingering
84%
Practically gang at a sex club!
About 6 months ago I went to my local sex club in Sydney. It was only about 8pm and not much usually is going on at that time. On the 2nd story there is called the "Orgy Room" a place where people go and sit on the bed with no locked door and it's just first cum first served. I stuc... Read full Story
shemale lover 2011-06-14 27,516 shemales gay male hardcore
85%
The invitation
The envelope was waiting on the mat when Jack and Sally got home from college to the small house they shared in North London. Sally scooped it and what was obviously yet another bill up from the floor and plonked them down on the table in the hall as she shrugged off her coat. The young pair were se... Read full Story
shemale lover 2014-12-15 6,694 shemales Fetish
91%
For a while I worked as a transsexual street prost
When I first moved to Sydney in my mid 20’s I had trouble meeting the bills. This was desperate times so after a lot of soul searching I decided that the only thing I could do was to become a prostitute. I knew Sydney that the transsexual prostitutes picked up clients on William Street near... Read full Story
shemale lover 2015-01-05 7,376 anal shemales hardcore
75%
Soo, my ladyboy friend in Bangkok
This shemale story is not your usual one as it's written by a lesbian girl Jamie and it involves a very sensual description of sex with an Asian ladyboy. Enjoy reading! Well as an openly gay Lesbian woman (submissive as I say) a long way indeed. My friend in Bangkok, Soo is a beautiful, articula... Read full Story
shemale lover 2015-02-01 8,543 Asian Ladyboy Shemale and Girl
63%
Thai ladyboy Jenifer
Another wonderful story posted by our reader Jason... I have experience with Thai ladyboys and Phillipino lady boys. The one Thai ladyboy that left the most impression on me is Jenifer. She is a bit big on size for a ladyboy, but her gentle demeanour sure make all for her size. The first time ... Read full Story
shemale lover 2015-04-09 5,863 anal tranny dick
86%
My First Ladyboy
I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers.. This particular Friday we were in the usual place chatting and having a nice relaxing time......when she walked in....t... Read full Story
shemale lover 2015-05-23 8,426 anal Blowjob Asian
94%
Deep Throating Shemale
Yvonne is one of my best friends and we do more than just hang out at the local nightclub. She has long wavy black hair and dark violet eyes. Like me, she is also a pre-op transsexual, which means she has breasts and a penis. In the few years that we have known each other, she has taught me a lot ab... Read full Story
shemale lover 2015-05-29 6,258 cock sucking shemale
69%
One of my real life stories with a post-op
This wonderful story was published at our forum, and, honestly, it was the first sex story involving post-op tgirls that I read, and I can't hide the fact that, although the girl had no hard one, it was still very exciting! Thanks for publishing it man! I was on vacation in Japan, and I went out ... Read full Story
shemale lover 2015-06-05 9,862 pussy Asian Ladyboy
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 14,912 shemales gay male Group Sex
90%
A TV in the Shoe Store
I work at a ladies shoe store at a large metropolitan mall. My name is Jillian, though my friends all call me Jilly. Those same friends also say that I am blessed with a beautiful face, and an athletic body! Pretty heady for a 30 year old woman whose ideas of athletics never got beyond sports i... Read full Story
shemale lover 2015-08-27 10,640 first time sucking shemale
82%
My shemale weekend
I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting... Read full Story
shemale lover 2015-09-05 9,374 shemales Group Sex interracial sex
78%
Hot Ladyboy
I had a phone number for a hot ladyboy that my friend insisted that I call for something different. I had always admired them but I had never been with one before. I finally decided to call the number a few nights ago and a soft feminine voice answered. The hot ladyboy was named Hollie and she to... Read full Story
shemale lover 2015-09-29 5,756 anal sucking nipples
81%
TV loving cock
Sorry I didn't keep you posted on Saturday night, but I was sorta busy being my usual slutty self. Story to follow: I talked to a guy on megaphone. He works as a night security guard at a big office building on the edge of town. He is there all by himself in this huge, mostly vacant building, in ... Read full Story
shemale lover 2015-11-17 5,650 Cumshot sucking Big Cock
97%
Willows transformation
Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, at best, 5 inches. My touch, or my tongue, on her clit seemed to... Read full Story
shemale lover 2016-02-04 11,904 shemales Fetish bdsm
97%
Sally Gets Caught
It is the fantasy of every cross dresser to pass as a girl but the only time it happened to me was when my partner caught me dressed in her best. For a minute or two she didn't recognise me but as the realisation of what she was witnessing dawned then things became very difficult. Understandably the... Read full Story
shemale lover 2016-03-02 7,841 shemale oral sex foot fetish
94%
Sex Ed Chapter One
My husband and I had quite an open marriage. We were both fairly sexually adventurous and this was reflected in how we both considered it to be ok for us to be going out and sleeping around, provided we were completely honest about it and came home and told the other one all about it. In fact, after... Read full Story
shemale lover 2016-03-08 6,495 pussy orgasm crossdressing
100%
Sex Ed Chapter Two
Over another drink, I learnt how David Lawrence had been dressing up as a girl since he was a teenager, always keeping it secret from his family and what few friends he'd had. He was shy around women and sex and had never had a girlfriend, instead he'd buried himself in his studies and dressing as a... Read full Story
shemale lover 2016-03-10 4,785 first time cum fingering
69%
The Training of Maria Louise
Chapter 1 I’ve decided, since you’ve told me you want to be a little dirty tart, that I should punish you by being a cuckold, someone who’s wife is unfaithful. We will begin by transforming you into Maria, we will apply your make up and dress you in white silk underwear, a nice ... Read full Story
shemale lover 2016-03-20 7,655 shemale Latex
83%
Revenge is a Dish Best Served Hot
Commissioned by: Hobgoblin Written by: christhestampede ~~~ Yuffie climbed off the Highwind's ladder and stormed across the field to a nearby clump of trees, fuming and kicking at the ground as she went. Before entering the grove she turned and shook her fist at the departing airship, cursi... Read full Story
BoyVixen 2016-03-30 6,091 cum lesbian dickgirl
84%
I posted a craigslist ad
8 years ago I began crossdressing again and playing with toys. After playing one day while watching videos online I decided I wanted to take the next step and be with a man again. My holes craved it but the butterflies in my stomach had stopped me before. Afraid they would do it again this time I go... Read full Story
shemale lover 2016-04-26 10,249 shemales gay male interracial sex