Sort by
Relevancy

Free Stories

100%
Honeymoon Suite
Two days after having been gang banged into ecstasy, I got a call from Lucas, one of the gang bangers who had brought me so much joy two days before. I was elated, but I tried to be calm and not let him know how happy I was to hear from him. He wanted to get together, just the two of us, for a more ... Read full Story
Regina10 2020-07-10 4,858 Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale Ass to Mouth
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 4,997 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
In the shadows of the city park
It is gonna be just one of those nights again. A night where the depraved girl in me won't stay quiet, demanding control and attention. I could feel it during the day already and now that the sun is about to set and the streets are slowly but surely emptying as I find myself in my appartment getti... Read full Story
Anna_Lima 2024-01-13 4,085 crossdressing blowjobs
91%
Stepdaughters Pleasure Daddy
As I was showering, I was thinking about Anna coming. What would I say to her? How would I act? I felt very uncomfortable and I was getting extremely nervous. I finished washing, then shaved. As I was getting dressed, Dawn came in. "I know your hungry, Daddy, but let's go out for breakfast.&... Read full Story
shemale lover 2011-12-05 7,471 anal licking Creampie
100%
The Conference Part 2
I was in an excited mood all day after the previous evenings surprise and events, and was anticipating another evening of fun. At last the time to meet in the bar came and I arrived to find Cleo in there with girl. I went over and said "Hi" and sat down. She introduced me to her friend ... Read full Story
shemale lover 2011-12-24 3,693 Fetish crossdressing erotic encounters
100%
TS Prostitute Urge
After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possibl... Read full Story
shemale lover 2012-01-27 3,420 Group Sex sucking cum
50%
Devastating and dominating
Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... Read full Story
shemale lover 2012-01-29 4,871 Masturbation sucking Creampie Latex fucking
100%
A Butterfly Emerges
It wasn’t my fault that my parents were small people and passed their genes on to me. However, it was a curse that I was forced to live with during my formative years. Sports like basketball, football and baseball were out of the question and I felt alienated from other children my age. My ... Read full Story
shemale lover 2012-02-09 3,155 Stockings sucking cum facial
50%
Every guys dream
Ever since I was a little boy I've always loved wearing girl's clothes. I remember going through my mother's lingerie drawer and trying on her panties and bras. I loved the way the silky sheer material felt against my body. As I got older I had less opportunities to indulge in my fetish until I got ... Read full Story
shemale lover 2012-02-11 3,696 Fetish cum crossdressing bisexual
100%
Daddies New Girlfriend
Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... Read full Story
shemale lover 2012-03-09 11,970 sucking Fetish crossdressing
100%
A Natural Sissy Part 8
Just as Stacy came back upstairs and told me the recreation room was ready for his tattoo application, the doorbell rang. "That's fine, Stacy. And just in the nick of time. That must be Heather at the door. Go let her in, please." Stacy looked at me like he could stab me in the chest wi... Read full Story
shemale lover 2012-03-25 3,058 cum fingering sissy
66%
Carmen's Experience
I had crossdressed for as long as I could remember, but know one knew my secret. I was as careful as possible. I began buying female clothes for myself at local stores, mostly womens Lingerie that I could wear under my regular clothes. By the time I moved out of my parents house I began taking hormo... Read full Story
shemale lover 2012-04-24 3,058 anal sex threesome Blowjob cum swallowing
100%
Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
shemale lover 2012-05-21 7,175 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Head Cheerleader Mikki Part 3 Michael is Back
To understand this story you must read the previous chapters. It's Sunday morning and I'm just waking up. I'm in bed alone. As I get up I see myself in the mirror. Still dressed in powder blue lingerie and a blonde wig. I wonder where the girls are. I leave the guest room and go into mine. I stri... Read full Story
shemale lover 2012-06-14 2,587 anal sex Cumshot Fetish
100%
Caught by the Past Chapter 2
Previously - After a drink with a new friend he invites you back to his house. Strangely drawn to this handsome guy he persuades you to dress in girls clothes... Now You're wearing a sexy leather mini skirt, fishnets and high heels, your cocks like rock and you're just about to show yourself... A... Read full Story
shemale lover 2012-06-28 2,743 Fetish cum Lingerie oral sex crossdressing heels
100%
Blushing Bride Chapter 3
"Those pretty white panties are appropriate given that it's going to be your first time," David, my friend and former flatmate said, lifting up the white skirt of the wedding dress I was wearing and running his hand over the white lacy french knickers that I wore beneath, the feel of his h... Read full Story
shemale lover 2012-07-21 4,522 cum Lingerie oral sex crossdressing
100%
Finally A Real Man
After my divorce I found I had some time to indulge in my many fetishes and fantasies. Those being; cross-dressing, smoking 120s and man to man sex. None of these were a factor in my separation however. It wasn't long before I was on line ordering lingerie and shopping locally. This has been going o... Read full Story
shemale lover 2012-08-06 4,645 anal Crossdresser oral
100%
Demoted Chapter 1
Monday I had been working in this office for a couple years, I was a floor supervisor had my own office and a few people under me. It was very easy and never had any trouble at all. I am also a cross dresser and I didn't know it but my story starts with a page I had on the Internet. I checked my ... Read full Story
shemale lover 2012-08-13 5,314 Crossdresser Fetish Lingerie
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,537 Crossdresser Cumshot Masturbation Lingerie heels
77%
Anything to make a sale
“David, you are not the right sales person for this account. I know the CEO of Cybertix very well, he’s been a client of mine for years, and he won’t relate to you.” I was sitting in the office of Victoria, my boss. There was a big sale opportunity at Cybertix and I badly ... Read full Story
shemale lover 2012-09-17 4,643 first time Cumshot Lingerie domination oral sex cum eating
76%
Brotherly Love, Sisterly Love
RICHARD My brother and I were especially close, as twins often are. We shared everything, including all our thoughts, feelings, experiences and desires. Even though we were eighteen, we still shared a bedroom too. It wasn't like there were things that we kept private from each other, it was the t... Read full Story
shemale lover 2012-09-28 6,425 sucking cum swallowing crossdressing
100%
Wife Converts Husband Chapter 4
Seeing as how Shelley is the money maker in our household, it is my job to keep the house clean, so every morning I get up and make her breakfast while she gets ready for work and since my feminisation, my wife has made me dress up as a sexy French maid while I do the housework. Shelley bought me... Read full Story
shemale lover 2012-10-18 3,864 anal Cumshot oral
92%
First Times
A little background is in order. During my teen years, I became involved with a woman that helped me discover the pleasures of my female side. Sue helped me to dress and act in a very feminine manner. We were almost like sisters in the way we became so close. She would sometimes describe how good... Read full Story
shemale lover 2012-11-02 3,784 first time Cumshot sucking
75%
Dottie's Back Chapter 4
Waking up on the single bed in the spare room was not the best way I could imagine to begin a day. Dragging myself from underneath the covers, I made my way to the bathroom and stepped into the shower. The previous night's events were still fresh in mind: Stacy having slept with another man and then... Read full Story
shemale lover 2012-11-02 3,368 Cumshot dildo Sex Toys
100%
FMDM Inc - The Interview
I had just finished a therapy session and was glad to get back to my office and relax. I'd have to lay off the cinnamon stix in the morning, my bustier was tighter than usual. My mini-frig offered a variety of drinks and I grabbed the pitcher of iced tea and poured a glass. Settling into the rich... Read full Story
shemale lover 2012-11-14 3,183 Cumshot Fetish domination
66%
Anal Queen
Amanda fell to her knees in the darkened theater and slowly unzipped my pants. My cock throbbed. As she pulled down my underwear, I felt my manhood spring forth. Amanda took the whole sausage into her warm, soft mouth. I could barely see her face in the darkness, but I could feel her between my l... Read full Story
shemale lover 2012-11-24 5,985 tranny anal sex Cumshot cum swallowing
100%
Slut bi cross dresser
Party Surprise - First sex as a Crossdresser. This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed ... Read full Story
shemale lover 2012-11-24 4,460 anal first time cd
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 5,091 Fetish oral crossdressing
88%
Sucking My first cock
It all started earlier this week, I had begun to watch a lot of sissy hypnosis videos and training videos, mainly ones from Polish Mistress. Every time I watch these videos, I usually would just end up masturbating or going on Cam/Phone with someone. But, after watching a 35 minute faggot hypnosi... Read full Story
shemale lover 2012-12-17 16,281 first time cum oral swallowing
73%
Nightclub Cum Slut
After splitting with my first boyfriend I went through a period of time I call my slut phase. I explored my sexuality in a massive way and did as much cock ass and pussy as I could. I thought that after I had been in a few relationships that my slut phase was over. I still had the odd one night stan... Read full Story
shemale lover 2013-01-10 7,018 Cumshot sucking ass fucking Guy Fucks Shemale ass fingering
100%
Find That Guy: Porn TV's TG Gameshow Round 02
"Welcome back, ladies and gentlemen, for round 2 of FIND THAT GUY" said the host, giving the camera his cheesiest smile. "We left off with our couple Sue and Winnifred holding only 7 points, and one of their opponents, Vince, having been disqualified. Their remaining opponents are Ric... Read full Story
shemale lover 2013-03-04 3,368 hardcore Cumshot sucking Lingerie ass fucking
86%
Hotel Heaven or Nightmare
You've enjoyed a relaxing bubble bath, you're smooth skinned and perfumed. You dress with your new purchases, Gio seamed stockings, leather mini skirt and Carvela heels with sexy peep toes. You take time to apply your make up while you contemplate what the evening will hold for you. There's nothing ... Read full Story
shemale lover 2013-03-12 5,826 sex toy Crossdresser Cumshot Big Cock Lingerie
92%
First time being dressed as a woman
I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman. Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a... Read full Story
shemale lover 2013-04-15 6,826 Crossdresser suck facial ass licking cd
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 6,214 ass Cumshot suck Lingerie facial nipples public cd
84%
Shool teen crossdresser first time sex
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest f... Read full Story
shemale lover 2014-11-21 18,235 first time suck fingering Lingerie ass fucking cd
95%
"University" Friend
University “Friend” Finally I had earned a little more freedom. I was off out of my sleepy village and at university. I had a small flat in an apartment block all to myself in a nice enough part of town. I unpacked my clothes and settled down for my first quiet night in, but as I put a few of my ... Read full Story
ATC97 2016-06-21 11,482 anal Teen (18+) Crossdresser Lingerie cd
85%
Escapism
‘Fuck yes! Yes Daddy! Fuck me like a little bitch!’ I scream into the pillow. My arched back allowing my partner full access to my greedy asshole. He slams harder in response. One leg bent, pointing a pink glossy stiletto heel towards the ceiling, bouncing against my stocking clad legs. Straig... Read full Story
chasingrisque 2017-02-03 12,350 transformation transvestite crossdressing transgender sissy
90%
Sister fucks Cross-dresser brother
James pulled his cock out of my pussy and scooted across the bed to my face. He aimed his blowhole for my mouth. "Don't get any on the pillow," I said. He didn't seem to hear. James hunched over. His eyes narrowed. He stroked his Johnson. The jizz flew. I opened my mouth and closed my eyes.... Read full Story
ASSEaster5678 2018-09-14 10,247 Ladyboy Sister and Ts Brother
66%
Oh Samantha
Meeting Samantha for the very first time at the busy theatre restaurant was the best thing that could ever happen to me. She was performing with about 20 other ladies or sort of ladies, I found out later that they were hot shemales, transsexuals and even a few transvestites. Their performanc... Read full Story
iluvgurls 2018-11-12 4,331 Cumshot Shemale Fucks Guy Blowjob Lingerie
66%
TO BE OR NOT TO BE – PART 5
TO BE OR NOT TO BE – PART 5 by Spanky de Bautumn Part 4. Sunny made a life changing decision and in the process becomes better acquainted with Mark. On Monday, I met Mel and Shari at the theater at ten to run lines. I was confident that I knew my part for the first act. My concern was with m... Read full Story
SpankydeBautumn 2021-02-24 2,024 Crossdresser Cumshot Masturbation Blowjob Big Cock Lingerie Interracial
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 8,115 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
Regina and Tommy
I was getting fucked hard and aggressively by a certified bad boy named Tommy. I've never been the kind of girl who liked bad boys until I met Tommy. Tommy like doing all kinds of wild crazy things to me and I was under a spell and couldn’t object. Tommy was like the asspussy whisperer and he gave m... Read full Story
Regina10 2022-03-02 2,751 Stockings Big Tits Cumshot Bareback Creampie Fetish Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Best Ride Share of My Life
It was a random Friday night. I was feeling a little frisky but didn’t have anything specific in mindA friend of mine works at a gay bar not too far from my house. Knowing my friend worked there I figured I could head over around midnight and see if there was something worth getting up to and if not... Read full Story
baldbeardbottom 2024-01-16 5,770 anal Amateur Cumshot Bareback Lingerie Guy Fucks Shemale Homemade
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 9,577 shemales gay male
92%
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 main... Read full Story
shemale lover 2014-08-07 6,810 sucking shemale teasing
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,403 shemales Masturbation Fetish
50%
The Invitation Part 4
The light was gently filtering in through the curtains as Jack slowly drifted towards consciousness. For a moment or two of his half awake and half asleep state he was confused - something didn't quite feel right. He stirred in semi consciousness and his eyes shot open at the unfamiliar sensatio... Read full Story
shemale lover 2011-10-01 3,745 shemales Fetish orgasm
50%
The Invitation Part 5
This is the latest installment of a story about cross dressing and the changes in a relationship between a young man and woman at college. Bits are autobiographical, but not as much of it as I would like! If this is illegal where you live, don't read it. If this sort of thing offends you, don't ... Read full Story
shemale lover 2011-11-20 3,115 Fetish crossdressing feminisation
97%
Stepdaughter's Transexual Surprise
I've been through two marriages in the past. My first wife died at an early age of 29 from a massive heart attack and my second marriage was a nightmare from hell, that I'm now free of. When I met Jeanie, I knew I had to take it slow and easy. Jeanie was a very nice lady in her early 40's. I myse... Read full Story
shemale lover 2011-12-04 13,382 anal Fetish transexual
90%
The Conference
It had been a long day at the conference. During my evening meal in the hotel restaurant with some colleagues I noticed a stunning looking woman across the room. We met eyes on several occasions and acknowledged each other with a warm smile. She stood up to leave the restaurant and I was able ... Read full Story
shemale lover 2011-12-24 5,431 Fetish crossdressing erotic encounters
30%
CD Delight
The following is an account of a true encounter between consenting adults. The names and places have been altered to protect the individuals. Any resemblance to actual persons is purely coincidental. It is not intended for minors. If you are offended by sexually explicit material or have receive... Read full Story
shemale lover 2012-01-27 3,138 sucking cum Sex Toys cd
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 8,029 Fetish transformation dildo
36%
A First Time for Hannah
At age 24 and after years of dressing in private, I finally decided I needed to get out. I had been scouring online personals for some time but never got further than exchanging a few emails and trading pics. I had been in touch with other CDs from all over the country and had even considered travel... Read full Story
shemale lover 2012-03-01 2,687 first time Fetish crossdressing
100%
A Job in the Theatre Chapter 14
Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties. "Nice. But I really think these will be better" Sarah said holding up ... Read full Story
shemale lover 2012-03-14 2,484 sucking shemale kissing
100%
Becoming Marie Chapter 2
After my encounter with Kevin at his office I knew that I wanted more. I had my own place and had started to build up a nice collection of lingerie which I would often wear while wanking to my slowly built up collection of porn. This was before the age of internet so it was sometimes hard to get por... Read full Story
shemale lover 2012-03-22 3,062 anal sex Creampie cum oral Lingerie
83%
Becoming Marie Chapter 3
On one of my bike rides and visits to the Transporter Bridge cottage I met a guy who told me of a cruising spot not far from there. He told me the place was much safer than cottaging, gave me directions to it and said it was always busy. The following weekend I set off on my bike wearing a loose ... Read full Story
shemale lover 2012-03-22 3,784 Bareback sucking cum