Sort by
Relevancy

Free Stories

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 10,899 Fetish crossdressing feminization
66%
I love Shemales
Ever since I was 13 I have had a thing for shemales. I had always wanted yo experience sex with a shemale. So when I was 20 I decided to get on an escort site and find a sexy Tranny. I ran across the perfect one so I immediately booked a date with her. So the dreamday finally came and I was so excit... Read full Story
Weinerboy6969 2020-01-29 9,192 Creampie Shemale Fucks Guy cum in mouth
70%
Anally destroyed by a Peruvian goddess
Browsing around the Transsexual escort ads here in town I found a new girl, something else than the typical manly faces with heavily photoshopped pictures. A Peruvian girl named Isabella had just arrived in town and was open for business. She has a few retouched pictures but also some natural selfie... Read full Story
Gracemel121 2017-08-07 13,669 Amateur Cumshot Bareback Shemale Fucks Guy Lingerie domination
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,086 fuck oral
50%
Fantasy Oral Sex with TS Lisa Lawer
This is a pure work of fiction and has nothing truth in it. Only truth stated here is that I am very fond of shemales and addicted to Shemale photos and movies. One particular Shemale whom I love very much is Lisa Lawer, she is from Brazil. I have been a big collector of her photos and movies. I am ... Read full Story
shemale lover 2012-06-28 3,254 oral fingering doggy style cum swallowing pornstar rimjob
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 13,934 hardcore sucking ass fucking Guy Fucks Shemale
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,243 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,157 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
100%
Fake plastic bimbo barbie famally in public part 1
My name is lana foxx,i am a fake plastic bimbo barbie shemale whore. I grew up in a whore house with my stepfsister candy,because my mom was a whore then and here job was an escort whore. from a young age, me and candy were interested in naked men, women and sex!! We allways walked in the room wh... Read full Story
Duckfaceslut 2024-05-07 1,527 shemale whore slut Plastic lanafoxx
75%
My First Time Out Part 1
Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms w... Read full Story
shemale lover 2011-10-17 4,302 first time cum oral
100%
Bimbo Bombshell
Bimbo Bombshell - Chapter One: Singled Out! Even though it was Friday, the bar wasn't particularly crowded that night. I never knew what hit me. This Gorgeous Blonde bombshell, starts flirting with me right a my table. I found myself wondering why this glamorous beauty, had chosen me. I was... Read full Story
Hardrock51Fifty 2024-04-07 3,187 Stockings Big Tits Shemale Fucks Guy Fetish Blowjob blonde domination Guy Fucks Shemale blonde shemale PDA Public Displays of Affection
57%
Transsexual Actresses Part 1
The adult entertainment market includes thousands of videos and DVD's featuring transsexual actresses. Some of the more popular of these celebrities have their own web pages. Brief profiles of some of these actresses, including a list of their films, appears after the initial list. Adriana Ventur... Read full Story
shemale lover 2011-09-08 9,139 shemale transsexual porn star
90%
It been extremely too long
For me, the ultimate feeling of femininity happens when a man is inside me, and It had been far too long. Over the last few years, my wife had effectively shut down my indulgence in the hobby of crossdressing in public - mainly at bars frequented by the transgendered and their admirers. She only sus... Read full Story
ASSEaster5678 2019-01-09 5,261 Shemale Fucks Guy Guy Fucks Shemale
100%
A Shemale Vacation Part 2
We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... Read full Story
shemale lover 2011-09-05 7,026 anal cumming cum swallowing
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,241 torture extreme fiction bondage and discipline
100%
Betrayed Chapter 10
I would have loved to be waiting at the gate at O'Hare when Dianna de-planed from L.A. that Sunday night. I had to settle for the Baggage Claim Area. Those people working for the Transportation Security Administration have no sense of humor. I guess at eight dollars an hour, they can't afford one. T... Read full Story
shemale lover 2012-05-30 4,627 hardcore shemale fuck
100%
My First Ladyboy Adventure
I had been watching ts porn and thinking about visiting an escort for a while, when I found myself working in London and actually got the oportunity. I had been checking out the London Eros guide on the internet and had called several tgirls when I came across Seri Atika's profile. I called he... Read full Story
monkeyphoto 2014-10-07 10,672 hardcore Asian Ladyboy ass fucking Guy Fucks Shemale condom sex
100%
Jon Story
When I learned we would be in Rio for a few days, I was overjoyed. Rio de Janeiro would have just what I was looking for. While on leave in Australia, I had developed a yearning for special girls, and through careful research, Rio seemed to be someplace very special indeed. It first started... Read full Story
shemale lover 2012-01-26 4,862 Creampie tits fucking big
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 4,903 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 8,887 Stockings sucking domination
100%
Date With A Mistress Part 2
The week went rather slow for Patrick and he was anticipating Friday night. He didn’t know what would happen as he picked up the phone. He dialed the number with trembling hands. When the phone rang the person on the other end told him to call back in an hour as the Mistress wasn’t at ho... Read full Story
shemale lover 2011-11-04 5,064 hardcore licking erotic encounters
100%
Witch Chronicles
I have been asked to write down my perception of the events of the war. After what's just happened, I thought it best to wait and rest before writing things out, but the big wigs want me to get it all down while it's still fresh, so don't expect this to be an extremely military report. I... Read full Story
shemale lover 2012-01-01 5,753 Masturbation orgasm fantasy tg
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 30,733 strapon porn
72%
My First Shemale Sex
Another lovely short shemale story from our forum member, this time from a guy who calls himself "I Fucked A Shemale" I was at my best friends house a couple of years ago. I was maybe 18 i believe. His step mom was there. Well his new step mom that his dad just married like a few days b... Read full Story
shemale lover 2015-03-07 7,643 anal Blowjob cumshots
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 6,784 transsexuals erotica romance crossdressers
84%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 118,500 hardcore Cumshot sucking bdsm domination
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 17,894 big dick anal sex suck Blowjob cock sucking workplace
100%
Born to suck
I’m a straight guy who watches to much porn and when I hit my thirty’s regular porn was getting boring. while searching the web I stumbled across some tranny porn, now I always loved blowjob porn it was my favourite but now watching a big dicked tranny getting her cock sucked is my favourite and I ... Read full Story
Beesknees 2018-03-02 6,358 Blowjob blowing
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 2,528 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
90%
Night With Shana
This meeting took place in Los Angeles, CA. I’m sure many of you are into shemale porn movies and will know who Shana is. For those of you who don’t know her, she is a gorgeous white shemale with long brown/blondish hair, big tits ( think there is some silicone in there — but who... Read full Story
shemale lover 2018-01-14 11,096 tranny suck face fucking
88%
Me being a pet
As you all know i am a bitch of my mistress "sissychick". This incident happen recently during my training of being a little slut. So i was sitting right next to my mistress bed, like a loyal dog, still having anal plug inside my ass and my dog collar. It was the mark of me being my mistr... Read full Story
shemale lover 2013-05-07 4,967 sex toy anal sex Shemale Fucks Guy domination cum swallowing
97%
Lucy change part 1
This is a story I wrote a few years ago, and completely forgot about. I'm thinking of continuing it if it gets any reaction. I was a virgin before I met my girlfriend, mostly because of my crippling shyness. She is the reason I overcame both problems, and I have never loved anyone or anythin... Read full Story
Alex1090 2015-03-31 11,856 tranny suck Blowjob shemale ass fucking Guy Fucks Shemale
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 9,370 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
95%
The club
The smell of rubber and latex and the combination of the strobe lighting was overpowering, the techno sound of the club just added to the already intoxicated atmosphere of the place. The club was a frenzy of half naked, latexed, rubberised bodies covered in sweat dancing to the frenzied sound of tec... Read full Story
shemale lover 2014-10-15 6,156 sucking facial deep throat
81%
Husband and wife used by Mr. Big Black Cock
We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and befo... Read full Story
shemale lover 2011-12-18 7,869 shemales gay male interracial sex
94%
She was a he
I was recently divorced, 39 years of age and living in an apartment in Sydney's inner eastern suburbs not far from the famous red light district of Kings Cross. After two failed marriages, I was footloose and fiance free and as lusty as a rampant bull on speed. I chased after anything wearin... Read full Story
shemale lover 2012-01-24 6,831 Cumshot Guy Fucks Shemale Frottage
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,471 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 6,920 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,329 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
71%
Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
shemale lover 2011-12-02 12,369 taboo Fetish crossdressing erotic encounters
100%
A Black Tranny Fantasy
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sleeping with a black shemale was about to come true. She paused... Read full Story
shemale lover 2012-02-08 5,318 Masturbation oral black tranny
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 13,717 Masturbation cum orgasm cumshots prostate
100%
Black Dickgirl Fanstay
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sleeping with a black shemale was about to come true. She paused... Read full Story
ASSEaster5678 2018-09-14 6,431 Ebony Ladyboy dreamgirl
94%
My Romantic One Night Stand with a Beautiful T-girl.
My Romantic One Night Stand with a Beautiful T-girl. A friend of mine landed a gig DJing at the well known dance club in West Village of New York City. She invited me to check it out. Why not, I had no plans that weekend and she can put me on the VIP guest list. Which means I don’t have to wai... Read full Story
My Shemale Attraction 2019-06-11 7,607 Big Cock Guy Fucks Shemale cum swallowing Love blowjobs cum in mouth My Romantic One Night Stand with a Beautiful T-girl.
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,512 Big Tits Big Cock shemale + shemale
100%
MY FIRST TS EXPERIENCE
I was traveling for work across the country. It was a long day. I arrived at the hotel, checked in, went up to my room and took a shower. I was hungry so I went to the restaurant in the hotel and wound up at the bar where they served food. I was alone so I sat at the bar at the only available sea... Read full Story
nico19878 2021-10-01 6,100 Amateur Blowjob Guy Fucks Shemale
100%
TG girlfriend is my new neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-01-17 4,042 Big Tits Bareback Creampie Shemale Fucks Guy Big Cock Asian Guy Fucks Shemale
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,416 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
A Fantasy - Part 2
Paula begins to grown, ohhing and ahhing. I suck hard and swirl my tongue around on the head of her cock. Sharon has pushed her dildo all the way into my ass and begins to pump my ass with a slow, steady rhythm. Paula holds my head in place and begins to thrust her cock into my mouth harder. "I'm go... Read full Story
swollenrooster 2023-09-20 4,879 Group Sex Cumshot Shemale Fucks Guy Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
100%
Charisma & Tiffany Part 1
As a beautiful shemale, Tiffany De Vine had had a lot of superb lovers, both male and female, but she couldn't get Charisma off her mind. She'd met the sorceress when she'd bought one of the brassieres that Charisma had designed. Actually, as she found out later, it was the only brassiere that Chari... Read full Story
shemale lover 2011-09-01 3,110 pussy oral sex tgirl
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 3,770 Fetish crossdressing erotic encounters
100%
A Maid Family Part 2
Sitting up with a start I felt the cold wet cloth that someone had put onto my brow fall into my lap, and then shortly after that I felt it slide in between my crotch and then onto the seat of the leather sofa where as luck would have it the damn thing then wedged up against me, and after a few ... Read full Story
shemale lover 2012-01-02 3,628 shemale femdom tg
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 4,840 sucking fingering Guy Fucks Shemale
100%
Being a shemale's toy can be fun
Joliet called and asked if I would be interested in having some fun...I thought about the last time and how pissed off she got. I hesitated long enough for Joliet to whimper in the phone 'I promise to make up for my last theatrics, no bondage and I will reward you very handsomely if you attend to my... Read full Story
shemale lover 2012-02-10 3,802 anal sex Ladyboy facial
81%
Barooms & Motels
Frankie pulled into the first motel he found, it was late and he had been driving all day. After checking in, he went to the room and tossed his suitcase on the desk and flopped on the bed. Frankie was on the road for one reason, he just left his wife of eight years and his kids, a son and a daughte... Read full Story
shemale lover 2012-02-24 3,979 anal cum oral Guy Fucks Shemale
86%
Wife Catches Me With A She-Male
It all started out one day I was sitting around in my apartment watching adult porno on the VCR. My wife had just left for work. I was horny and my cock was hard so I started jacking off. I was lying on my back pumping my cock hard when I started to cum it had been a week or so since I had any pussy... Read full Story
shemale lover 2012-10-22 5,931 Cumshot Creampie shemale jerking