Sort by
Relevancy

Free Stories

100%
Angel Chapter 2
Angel Jones stepped off the train and hoped she was in the right place. It was noisy and confusing in the terminal, a far cry from the relatively quiet station in her home town where she had boarded the train that morning. One hand clutched a small suitcase that contained her makeup and clean linger... Read full Story
shemale lover 2012-11-30 4,080 oral sex tgirl feminization
100%
Angel Chapter 10
The sex on Friday night and Saturday with Bob Marley Cliff was the best Angel had experienced up until that date, but it was only one of many fabulous carnal adventures in her life. Because of her beauty, her sexual prowess and her reputation as a woman who was free and open with her charms, she had... Read full Story
shemale lover 2012-12-02 3,648 Cumshot sucking fingering handjob
100%
Duchess of Lamore
Rolls Royce London It was a typical day in London. It drizzled that morning clearing the air if only for a little while. Drake Hampstead appeared at the office directly before 9:00 AM. He was never late. He took his job at the Rolls Royce office very seriously. There was a definite pecking or... Read full Story
shemale lover 2012-12-02 3,657 sucking tit licking
100%
Fun With Friends Chapter 5
When I got home, I spent the rest of the evening thinking about how in a few hours I had gone from a closet cross dresser to a full on cock sucking, bend over and take it up the ass slut who was then shown to a group of strangers as a latex and high heel-wearing sissy. I'm not sure when I fell as... Read full Story
shemale lover 2012-12-12 3,070 Stockings sucking Sex Toys crossdressing heels
100%
G Is for Gemma
Stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It all really started on a Monday. One bright sunny Monday, early summer, an unusually warm day for June in England. And it really was stupid thing to do... Read full Story
shemale lover 2012-12-15 4,536 anal Cumshot cock sucking club
33%
Old Folks Chapter 1
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 2012-12-21 4,058 Stockings Crossdresser Lingerie Mature cd
94%
Pre-Op Roommate
I was a few months away from graduating college with my Theater Arts degree when Mark, my roommate, told me he was going in for the sex change operation. We popped a couple of beers and talked about this thing… he wasn’t sure whether he liked guys or not, he’d never done anyth... Read full Story
shemale lover 2012-12-22 6,431 Crossdresser sucking ass fucking handjob
85%
Joe Surrenders
My new partner is not really a girl's idea of a "ladies man." Nevertheless I have known Joe for a long time and when he asked me out I jumped at the chance. I had no illusions about Joe but one asset he does have is a decent bank account! His parents had died and left him with a nice house... Read full Story
shemale lover 2013-01-17 3,746 Cumshot Lingerie domination handjob cd
90%
Steve to Stephanie Chapter 1
Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve did not consider himself gay because he really wanted to be female. While having sex, Steve fantasized about being the woman. Since he normally bottomed it was fairly eas... Read full Story
shemale lover 2013-01-22 3,773 Crossdresser sucking Blowjob cd gloryhole
92%
A Surprise Relationship
This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony&quo... Read full Story
shemale lover 2013-01-29 5,118 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Steve to Stephanie Chapter 1
This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve... Read full Story
shemale lover 2013-01-29 3,672 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Love is Grand
PREFACE Retired and independently wealthy, 60 year old Stan Berman discovered he had only 12-18 months to live due to a rare neurological syndrome that would sap his strength and motor skills, but the symptoms would not onset for at least a year. The widower's only family was his devoted son Pat... Read full Story
shemale lover 2013-02-13 5,834 Teen (18+) Amateur shemale transformation
100%
Pygmalion
Some of the coed students in Professor Higgins' Sculpture 101 class regard him as a sexist or, as Amanda Blake describes him, as if she were living back in the sixties, "a male sexist pig." He does have an eye for the ladies, I'll grant you that (he's ogled me enough times!), but what man ... Read full Story
shemale lover 2013-02-22 4,930 hardcore Big Cock ass fucking Guy Fucks Shemale ass fuck
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,488 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
100%
The Meeting of Cortney and CiCi p1
Cortney could not keep herself from thinking about the upcoming date with CiCi as she sat in the luxuriant bath water and shaved her legs. She planned to fuck the glam slut whore long and hard. But first, the metamorphosis to turn her into the dome bitch - Cortney. She rose from the bath, patted... Read full Story
shemale lover 2013-04-15 3,453 suck shemale oral Lingerie make up
100%
Pounded to submission part2
Two days ago Joesph was checking out porn. A couple of BBW vids here some interracial there, the usual. Then he saw a just viewed picture with a Brazilian She-male and couldn't stop looking. With his curiosity getting the better of him he clicked on it. She was gorgeous! Her face appeared to be as f... Read full Story
shemale lover 2013-04-21 7,715 Cumshot suck shemale oral deep throat
100%
Fitting Room Fantasy
Being a 'girl of a certain kind', I always use the women's fitting rooms in stores when I am out trying and buying clothes. I tend to avoid the 'communal' type, where we are all stripping off together, as I'm quite shy and you also never know if someone may pick up on the fact that not everything ab... Read full Story
shemale lover 2013-06-04 6,201 ass Cumshot suck Lingerie facial nipples public cd
90%
Tranny Fuck
Its about midnight, and I'm horny a fuck. Couldn't find one of my late night freaks to come over and milk the cow, so i headed over to the east side to see what was going on at the strip club. As I get off on the exit, there's this long road that leads to the strip clubs. Its dark, on this side of t... Read full Story
shemale lover 2013-07-18 5,714 anal sex Blowjob ass licking 69 balls licking
95%
Dana becomes a woman
All her life, Dana had felt different. Born a boy, she always preferred dressing in girl clothes and playing girl games. She was mistaken for a girl from the time she was toddling - her feminine face and manner always convinced people. By the time she graduated high school, Dana discovered her ma... Read full Story
shemale lover 2013-07-20 4,473 Crossdresser Cumshot Masturbation oral sex ass fingering
95%
My first shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe t... Read full Story
shemale lover 2013-07-21 11,531 anal sex ass licking oral sex kissing transexual
88%
Never Wanted To Be Your Girlfriend Ch. 01
So here I sit, waiting to hear what will become of me, and I can't help wondering how the hell I got here. I know how it all got started. And it was all Michael's fault -- Michael and I met my first year of high school. We were both the smart nerdy types. And at around 5'6" and just over a 100 po... Read full Story
shemale lover 2014-07-19 6,860 Cumshot suck Blowjob Lingerie facial
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,541 Masturbation cum orgasm cumshots prostate
100%
Desire women
I met with men she had no men I had to go a long way to her ... As a child, a very strong impression on me has made, lesbian scene in a porno movie, (then I do not know why) Two luxurious woman in underwear sitting on a bed in a hotel room kissing, caressing each other .. the fact that a woma... Read full Story
Lola Spais 2016-10-28 4,926 Crossdresser shemale lesbian ladybou
55%
story of Jojo
Some find it confusing of who i am or what i am, including me. i found some kind of definition: femboy A young boy who presents extensive feminine mannerisms and actions often blurring the line between a boy and a girl. Can be confused with a cross dresser, but it usually refers to boys at v... Read full Story
jojo58654 2017-09-12 10,322 Amateur transvestite strapon cd femboy
66%
The Coma Girl Brain Transplant
[This frivolous story is something I put together as an entry for a comedy competition earlier this year, not to be taken at all seriously, a bit more sci-fi than erotica, more of a mind-fuck than anything else so it’s not jerk-off material but hopefully some of you might still enjoy it] Thankful... Read full Story
cara_elaine 2017-12-19 6,298 Crossdresser Uniform domination
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 17,819 Shemale Fucks Guy
92%
My Dream pt 3
Our first invitation arrived at the end of September. Sydney spotted it first and tossed it into the trash with out looking at it. She didn't tell me what it was and I didn't bother asking. The next invitation arrived two weeks later. This one Sydney opened and after reading it she passed ... Read full Story
Sydney Sun Min 2018-01-04 16,234 Group Sex Shemale Fucks Guy Shemale and Girl Sex Toys
78%
What Lies Beneath (Part 2)
A RENDEZVOUS WITH SUZY – What Lies Beneath (Part 2) We woke in the morning, showered and dressed before going down to make breakfast. Mia must have planned this all with the girls in advance because she had packed a small suitcase with some day clothes for us both. The sun was streaming throu... Read full Story
The Adventures of Mia & Seth 2020-08-18 7,475 Group Sex Shemale Fucks Guy Shemale and Girl Interracial Latex toys
81%
A Fantasy Fulfilled
I usually comb through the web for cool first experience stories involving men and CD gurls. I realized that I should also contribute my own, however. Mine occurred years ago when I I’d just broken up with a long time girlfriend that I’d been living with since my college days. I was in a financi... Read full Story
jaytop00 2018-04-03 13,986 Crossdresser Blowjob foot licking toe sucking foot-worship first time with a tranny
91%
Chicago TG Romance
Most transgendered girls I have met want to be treated and romanced just as a normal girl would. Only in the height of passion should your animal instincts take over. I was in a Las Vegas club earlier this year and had great conversation with some tranny women. I was instructed if I wanted to meet s... Read full Story
Jon Paul 2018-06-04 7,707 Cumshot Bareback Blowjob Asian Ladyboy
83%
Wife Left Me so I Could be a Girl
I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with... Read full Story
ASSEaster5678 2018-07-09 10,199 Shemale Fucks Guy Ladyboy Mature
100%
The picture.. (foot fetish)
So I've been into Erotic roleplaying for a while now, and recently about two months ago I had this really fun and kinky experience. A partner of mine which I usually roleplay with over a communication program were just talking about, and one thing lead to another and eventually we just started dirty... Read full Story
LouiseFEM 2018-09-05 3,120 Crossdresser foot fetish feet picture Roleplaying
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 32,211 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
87%
Dani & Paulie - 1
It was two years since Carl had taken me in the cellar of that bar. Paulie and I had moved to a large apartment courtesy of an unexpected inheritance from his father. I should really say "her" father, we had started using feminine pro-nouns for each other somewhere along the line, no one could reme... Read full Story
SissyDani31 2018-10-08 3,837 Crossdresser Amateur
82%
Halloween Double Cross
It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeou... Read full Story
ASSEaster5678 2018-10-29 11,061 Shemale Fucks Guy sissy Halloween
66%
The Audition
New York City wasn't a bad palce to be back then. I was a student working at an office job and doing what I enjoyed. That was being a musician. Lots of weekend and night gigs at cocktail parties, lounges and so on. There were a few pianists I worked for as standing time-keeper ( bass play... Read full Story
iluvgurls 2018-11-12 5,457 Stockings Cumshot Fetish Blowjob blonde Lingerie Guy Fucks Shemale cum in mouth
50%
Transgender Biology
I remember one of my girlfriends from highschool telling me about how myself and anyone else in school would not even believe it was HER if she showed up without make-up some day...I had said oh c'mon yer gorgeous...she laughed and said " Actually, I am not haha! But I know HOW I WANT to Express Mys... Read full Story
Katrina_Electrika 2018-11-20 2,298 Ladyboy
57%
Many People Still Don't GET IT about Transexual Ladyboy Types. .
The most common argument that Anti-Ladyboy people often say, (and they are usually from the Extreme Religious Right such as Orthodox Christianity, Roman Catholic, Islam . . . ) is that Ladyboys are ' trying to fool ' everyone that ' they are a woman ' . . . - Here is a FACT : Ladyboys I hav... Read full Story
Katrina_Electrika 2018-11-28 4,083 Ladyboy
66%
wishing
When I would get off the bus from after school activities, I would always walk through this truck stop on I-94 east of the Twin Cities. I would always look at the truckers parked for the night in the back. I always wondered what would happen if I brought my desires and fantasies to life for one of... Read full Story
cd4fun715 2019-01-08 2,682 Crossdresser Amateur
89%
The Truth about The Fate of Mariana Cordoba..still searching. .
Just yesterday, yet another strange FACT has emerged. And it is not the purported fact which is stated in this new purported information, but the FACT that it is the Same Person posting about Mariana and making the same claim that Mariana has passed away. . . . and THAT person making this statemen... Read full Story
Katrina_Electrika 2019-01-08 76,618 shemale + shemale
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 5,208 Crossdresser domination PRISON FUCKBOY PRISON PUNK prisoner prison sex Prison Bitch
87%
My first experience with cross dresser....
It was the beginning of the summer vacation.. we all guys headed for the beach to party and get wasted!! I had my friend Jimmy sharing the room with me. I knew him from school days so we used to get along very well. Until one night we were getting ready for a party I just saw a stockings and a fema... Read full Story
My rod 2019-03-18 6,568 Crossdresser
54%
My lifes story, which I want to share it with world!
Since my childhood very beginning every time when I see female to which I am attracted to, I imagine how I would go down on her, I just love to do enjoying it for hours. I am obsessed with cunnilingus and I do it with passion!... and then this happened... I'm still writing my full movie scene abo... Read full Story
Sanitaladyboy 2020-09-02 3,522 Stockings Crossdresser Amateur Group Sex Shemale Fucks Guy Fetish threesome Big Cock Ladyboy Lingerie domination Sex Toys
87%
My first bi encounter
As a young catholic boy I always prayed I would have a women’s body. I would wear my sister’s clothes and masturbate in my bedroom. I have been a closet cross-dresser for a long time. In my early twenties I rented my own apartment. I would buy from Fredericks of Hollywood catalogue for my outfits, ... Read full Story
Palba 2020-11-12 6,382 Amateur Bareback Creampie Ass to Mouth guy fucks shemales
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 11,059 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,354 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Father-in-law is my slave--001
Partly real partly fictional The sun shining down the room, I lazily opened the quilt, it has been cold for several days, I got up and looked at myself in the mirror, with a handsome face, but I was wearing a pink silk skirt pajamas and a pink silk low waist bag Pants, there are things in the pants... Read full Story
kelly2014 2021-03-30 4,834 Stockings Crossdresser Amateur Fetish Asian Lingerie domination Futanari shemale + shemale
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 8,075 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
Camming down the rabbit hole Ch1
Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... Read full Story
Dani_does_Dallas 2021-08-11 5,105 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
The Biology of Music - I fucked my trans substitute teacher
I was never strong in school. I wasn't very interested in what we were being taught, and the teachers liked me enough to not give me too hard a time about it. I attended an all boys school. It was actually quite a religious school which makes this story all the more surprising. I was in the middle c... Read full Story
terrifictim 2022-01-03 3,590 Creampie Guy Fucks Shemale feet licking first time with a tranny teacher student
100%
Junior's Department
Junior’s Department The long-haired young male browsing alone in the ladies’ junior’s department caught his eye and he stopped walking to the store exit. He stepped behind a display rack across the aisle, then watched him approach a mirror and scan the area before holding the skirt and blouse up ... Read full Story
AuthorJordanSkythe 2022-01-20 2,550 first time Stockings Crossdresser romance femboi
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 3,862 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
First Time Buying Lingerie
As a youngster, I couldn't help but notice the carousels of hosiery on display in various shops that my mother would visit. Displays of stockings and tights (pantyhose) for the discerning housewife. Brands like Pretty Polly, images of nylon clad legs on the glossy cardboard and a see through window... Read full Story
Daddybear71 2023-09-13 6,210 Stockings Crossdresser Amateur Masturbation Lingerie teen (18+)
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 3,915 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
57%
First time
Me 24 was outside having drinks with my uncle After a wedding in our hotel when I saw female figure pacing back and forth through the parking lot, we glanced at each each other more than once it was very mysterious. I then continued to finish my beer and head inside and say say goodnight to my uncle... Read full Story
Jackmn 2022-07-26 4,827 First time with a Shemale
100%
How I became addicted to my toys,
How I became addicted to my toys I tell in this story my experiences by showing how I developed my share of femininity and the toys that I use in bed to amplify my pleasures alone or as a couple. For several years now I have discreetly rented a second garage near my home to store my wigs, dres... Read full Story
sandratvtg 2022-09-20 4,537 Stockings solo Lingerie Sex Toys