Sort by
Relevancy

Free Stories

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 15,198 first time shemales interracial sex
81%
First time in Bangkok
If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floo... Read full Story
shemale lover 2015-01-13 13,791 shemales hardcore Group Sex
93%
My First Time
This is my first ever story written about my first ever sexual encounter with a transgender woman. I really hope you enjoy and want to leave me some feedback… I have slept with many women in my life. I have been married, had more girlfriends than I can remember, several fuck buddies and far too m... Read full Story
⭐TransGurl⭐ 2016-06-21 23,400 first time tranny shemale tgirl ts experience
94%
My First Time Made Me A Slut
A true story of my first time. And why I so need a daddy now. The first time I went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to pull it down as cars were wizzing by. I walked or should I say wobbled the... Read full Story
Teddie 2018-09-12 12,713 first time Stockings Crossdresser Bareback Blowjob blonde Big Cock gangbang domination Guy Fucks Shemale slut cum in mouth
44%
First time with a shemale
I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time. I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth,... Read full Story
shemale lover 2012-02-14 7,305 first time Stockings Small Tits
93%
First time
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny... Read full Story
shemale lover 2013-07-20 5,103 first time Cumshot oral sex Guy Fucks Shemale kissing
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 4,505 first time cum oral
87%
Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
shemale lover 2011-08-24 9,399 first time asshole shemale
94%
CD and BBC Gangbang 1
My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, mid thrities, white, 5' 9' 165, reasonably handsome, both in and out of women's clothes. One of the ways I express my sexuality is to dress as a woman and get fucked by other men. Preferably in a humiliati... Read full Story
FionaFucked 2014-10-27 14,131 Group Sex gangbang Interracial cd sissy
88%
First Time Outdoor Festival Fantasy
Fantasy Setting: Summer time in the mountains of Colorado the perfect bluebird weekend we all dream of. The day before an underground rave in the mountains all my friends bail on the show and was now left with either not going or going solo. Well I deiced what the hell and I'll go solo an... Read full Story
xaviergc8 2016-10-26 9,732 anal first time shemale gangbang bondage outdoors fuck toy
100%
HELPLESS TO MY CRAVING FOR BLACK COCK
This is a totally true account of my addiction to meth and its hand in turning me into the he[pless sissy I've become to my weakness for BBC. My name as a regular male is Richie Budd. But by reading this you'll soon realize that nothing is normal. Not only was I Richard Budd. I spent an equal, if ... Read full Story
Tvtrinity 2021-04-07 10,190 Crossdresser Amateur Group Sex gangbang Interracial transgender sissy bbc Black Owned owned white boy pimped force feminised BNWO
100%
Vanessa and the workmen gangbang
The three workmen were slaving away in the back garden, in the hot sun. Vanessa watched them from the upstairs bedroom window, getting more excited by the second. Under her robe she was wearing a beautiful red basque with a red g-string, black stockings and five inch heels. This was topped off with ... Read full Story
Vanessa Luv 2020-05-12 5,755 Crossdresser Group Sex gangbang Lingerie cum in mouth double anal
93%
Sissy Maddie's New Apartment Gangbang
I’d just moved into the big city. Me on my own in a cheap apartment block. The flat was nothing special by any means, and the room next to mine seemed to be noisy with parties. But I was glad to be on my own. I had almost finished unpacking my belongings when I came across my stash of female clothi... Read full Story
sissymaddiex 2020-09-25 10,260 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 6,164 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
darrell 2022-01-03 5,007 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
100%
My First Visit to a CD Sex Club
Feb 16 Time off work booked, nice new wig, false nails & lashes, & a nice new sexy red bra & panties from Ann Summers & I'm all ready for a fab day at Happy Mondays @ lovejoys on the 22nd. I'm really looking forward to meeting SuzieStern & all the other girls. Its been way too long since I last m... Read full Story
Lacy-Rose 2024-09-02 1,224 Crossdresser Amateur Group Sex Cumshot Blowjob gangbang cum in mouth
68%
I meet my new Mistress for the first time
I was feeling excited about and looking forward to Friday night. The reason for this was that I intended to dress up as my alter ego, Tania Harvey, and to go for a night out to a club nearby that is popular with TG’s, TV’s and other like minded people. I took a lot of care and attention over the way... Read full Story
Tania Harvey 2017-06-26 8,281 Amateur gangbang 3some shemale on shemale dominating
50%
Angel The Shemale Vampire
Angel stood in the shadows watching hungrily as the group of laughing young college kids came toward her down the alley. The group was made up of four guys and a girl. The girl was hanging all over one of the guys and it screamed how badly she wanted to get in his pants. Angel's smile broadened with... Read full Story
ASSEaster5678 2018-10-29 7,556 Group Sex shemale vampire
80%
Group Sex
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-04-19 3,404 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale cum in mouth
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 10,758 Big Tits Big Cock shemale + shemale
71%
A Night of Makeup, Cock and Cum - froam Annamalice
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I... Read full Story
shemale lover 2011-11-21 5,276 shemales Group Sex Fetish
100%
The Triple X cocktail - Wife Shares Shemale With H
"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an ... Read full Story
shemale lover 2012-02-21 3,843 Group Sex Creampie face fucking tit licking
100%
First Time Sex With Tranny
Wow - if you have ever wondered what it would be like to be with a TS girl, this would be a great place to start. Just got this from a “friend” of mine who wanted to write about his first TSgirl experience. Can’t say for sure if it’s 100% true, but who cares? I do know that they were together so ... Read full Story
sach 2015-11-16 8,032 first time tranny suck stroking mutual sex
100%
Susan's First Time Part 3: Susan's First Party
The chauffer passed through a gate in the high brick fence just as the sun started to slide behind the distant snow capped mountains. The cobblestone driveway that wandered toward the main house must have been a mile or more long. Susan admired the immaculately landscaped grounds as they drove throu... Read full Story
shemale lover 2011-10-13 2,680 anal Group Sex Creampie oral
100%
Discovering Mistress Sarah's World Part 6
Chapter 15 Joe's first 'female' public appearance as Josie was approaching fast. He was nervous about it. Fortunately Mistress Sarah had kept him busy most of the day so his mind was distracted. Shortly after his mind blowing masturbation session with her in the morning, she left to run errands a... Read full Story
shemale lover 2012-10-03 4,327 first time domination Sex Toys
100%
Dottie's Back
Four weeks had passed since my first blowjob party. In that time, I had become obsessed with getting implants. The concept of being tit-fucked and wearing deep-cut tops without being concerned about the distinct line between my flesh and the fake boobs had become a constant fantasy of mine. After be... Read full Story
shemale lover 2012-11-02 3,995 Group Sex Cumshot facial oral sex
89%
A New York Adventure - My fantasy
It was my nephew Simon’s stag weekend in New York; I really didn’t want to be there but my sister insisted and my wife and daughters backed her up. My useless brother-in-law had deserted his family years before and I was expected to be a guiding influence; and so Simon, several of his friends and I ... Read full Story
Curious Daddy 2014-06-06 7,825 Group Sex Cumshot suck shemale Big Cock
100%
First Tranny Experience_Part 2
I had said good bye to her at her door and drove home. I got home at a decent hour and went to bed. The following day at soccer practice, I could only think about how wild a time we had together and began fantasizing about the whole affair when my cell phone went off. To my surprise, it was Kim s... Read full Story
Jon Paul 2018-08-06 4,933 Group Sex Bareback Creampie Blowjob Asian Ladyboy
100%
Club sex the 25yo
There’s a very special private club around, it’d meetings take place in a very secret place. It takes a lot to gain membership. You have to either have a lot of money AND a friend in the club OR you have to take part in the ceremonies for at least a year. Also you have to be willing to b... Read full Story
shemale lover 2011-12-10 5,146 anal Group Sex lesbian
100%
Big Surpise In Small Package
It was a Friday night and I was extremely horny and just my luck my girlfriend was out of town, but I wasn't horny for her I was craving cock. I knew I was bi for a long time and loved to have a nice hard cock to play with every once in awhile. So I decide to call my girlfriend to tell her I was goi... Read full Story
shemale lover 2012-06-11 4,417 anal Group Sex Cumshot Blowjob
100%
Fulfilling A Girl's Male Fantasy Part 2
Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a ... Read full Story
shemale lover 2012-04-04 4,511 Stockings anal sex Group Sex Blowjob
86%
My first time as a Femboy CD
My name is Nick aka. Nicole. I am a 20 year old gay femboy crossdresser and this is a little story of how I started dressing to become Nicole and my first sexual experience besides masturbation. I grew up living in an apartment complex with my mother and sister, who was 2 years older than me. M... Read full Story
Nicole_femboyCD 2014-12-03 191,487 first time Crossdresser suck Blowjob oral cd
100%
First Encounter (Mexican Travesti)
I grew up near the U.S.-Mexico border and am ½ Mexican Hispanic and ½ Anglo (white). I visited Nogales Senora on the Mexican side on and off during my teen years. As a young adult, I was fearless and sometimes went across alone to visit the strip clubs, get a cheap lunch, or look for Mexican sweetie... Read full Story
AllenB 2022-09-07 7,049 anal sex Shemale Fucks Guy Blowjob mexicana cum in ass first time with a tranny
40%
First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... Read full Story
shemale lover 2012-09-27 5,758 first time Fetish cum oral crossdressing nylon
95%
First time
Hi, my name is Sandra. In fact, I'm not exactly a girl, but a CD. Even as a child, I felt different and I used every opportunity when I was left alone in the apartment to dress up, to put on women's clothes, to put on make-up. In time, I started watching porn, as did all my friends. But, unlike them... Read full Story
cd Sandra 2021-10-13 5,858 Stockings Teen (18+) Small Tits Crossdresser blonde Guy Fucks Shemale
96%
My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
sach 2016-02-16 13,678 first time tranny ass fucking guy on shemale mutual suck
94%
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
qtball 2016-08-29 12,666 anal tranny Blowjob Big Cock bj asstomouth
84%
Fucked by a Shemale
My names - and I would like to tell you about a very sexual experience I had recently. First I would like to tell you I’m 30 years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bi... Read full Story
shemale lover 2011-08-18 169,850 first time shemale cum
100%
TG - shemale at the airport
Layovers are a pain at the best of times but the prospect of five hours at the airport was not a good one. My inbound flight had been delayed and I had missed my connection, so there was nothing for it but to wait out the afternoon and catch the next 'plane home to the wife and kids. The only ... Read full Story
shemale lover 2011-10-15 10,514 first time asshole oral deep throat fucking
100%
Jack & Jill - his first time with a transexual
Jack and Jill meet It was when I went to the patio to enjoy a cigar after dinner that we met. On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighte... Read full Story
shemale lover 2012-04-09 5,446 anal sex oral sex cum swallowing deep throating
100%
Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
Sissy Ava 2022-10-11 8,081 Stockings Crossdresser Amateur Bareback Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
100%
My Noisy Upstairs Neighbors Part 3: Making Porn
In Part 2, I recounted how Paul, my commanding upstairs neighbor, coerced me into making porn with him and his younger roommate. Now, I'm excited to share the first video we created together. At 12:45 PM on Saturday, I nervously approached Paul's door. After knocking, Paul opened it with a smile ... Read full Story
Chrissy Tunnell 2024-07-16 2,786 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
100%
Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
Regina10 2021-04-09 4,625 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,891 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
smtmsbrianne 2020-09-16 3,702 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Creampie Big Cock gangbang redhead Guy Fucks Shemale Ass to Mouth cum in mouth
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,462 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 7,838 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
0%
The Greatest Lie Part 16
As soon as we were safely back in our hooch, I retrieved the iBook from its hiding place under the floor and opened up Spartan's main Excel spreadsheet. I re-sorted the list against the data from the last three weeks of our frustrating field work, by district, language group, age, and every other ca... Read full Story
shemale lover 2012-01-20 5,129 first time femdom crossdressing
85%
Gilding the Lilly
It was a dark and stormy night. Oh, wait, I was taught NEVER to begin a story like that. (Snoopy can get away with it, but he does all his writing with a typewriter balanced on his doghouse). OK, getting back to important things. It was actually early Autumn out in the Desert, cool weather was s... Read full Story
CharlotteSlut 2018-03-02 6,168 Group Sex Shemale Fucks Guy gangbang Shemale and Girl shemale + shemale
85%
The Gang
I had always thought of myself as female in spite of the fact that I was born with male genitlia. Even in my earliest memories where I had witness sex, I identified with the female in the relationship. As a small young child, I had always longed for womanhood each time I heard a woman sing or especi... Read full Story
Regina10 2020-06-29 9,083 Group Sex Cumshot Blowjob Big Cock Ebony gangbang double anal
100%
Tranny Gang Bang
Gang Banged I stood there looking in the full length mirror very pleased with the image I saw. I was ready for the evening and the first time I would be with more than two men at once. Freddy, had talk me into doing him and two of his friends in a sleaze motel. Freddy had found me on my internet... Read full Story
shemale lover 2011-11-12 4,885 shemales Group Sex gangbang
86%
Alex’s Bottom Slut
So when I was younger, I worked at a pizza place as a delivery guy. It was a pretty boring job for the most part but that all changed one night. I got a delivery to just outside of our range but decided to take it anyways because we were slow. When I got there a very tall and muscular black woman in... Read full Story
Jsmithsub 2019-11-18 57,073 Group Sex Cumshot Shemale Fucks Guy Blowjob Big Cock Ebony gangbang domination Interracial Ass to Mouth cum in mouth
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,468 first time ass Cumshot suck cd sissy make up
98%
When Fantasy Comes True 2
After my first threesome encounter with Jenni and her friend, getting a golden shower from three trans women was a bonus. Being drunk and now four of us snuggled in bed, i thought the night had ended but i did hope for more. I was not disappointed as Jenni's friend (Sasha) who had been sleeping d... Read full Story
Sara Banks 2018-10-22 11,897 Group Sex Cumshot Bareback Shemale Fucks Guy threesome Blowjob Big Cock gangbang domination Ass to Mouth cum in mouth golden showers golden shower
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,946 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
92%
Showing my femininity
When I was still little guy, my stepfather always told me I wasn't a real boy, but I was his little girl. One day, he was drinking beer with his friends, so he grabbed me by the arm, pulled my shorts down and showed off my teeny cock to them. I remember that all of them laughed at me. They made fun ... Read full Story
Shemale Dill 2020-04-27 8,134 Crossdresser Amateur Group Sex Blowjob Big Cock gangbang Lingerie