Sort by
Relevancy

Free Stories

83%
The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
badbadboi667 2021-01-04 4,836 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Big Cock gangbang domination Homemade Ass to Mouth cum in mouth
100%
Sissy Training
This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We&r... Read full Story
shemale lover 2012-03-12 7,996 Group Sex Fetish bdsm
66%
Ladyboy dominatrix
If you read my other stories you know I'm intersexed and I was a ladyboy prostitute when I was um, very young. I don't condone such activities. They were sick perverts who used me. True I got a lot of money and expensive gifts but that doesn't make it right. They should all be castrated. Th... Read full Story
shemale lover 2012-10-15 9,707 Fetish Asian domination sissy rimjob
100%
Gangbanged at the beach
My BBC friend took me to the beach, where people make sex. We arrived in his van. I was in the back of the van, chained blind folded, with my mouth wide open and a huge horse dildo in my sissy pussy. Suddenly I hear the van door opening. I hear many voices of other men. My BBC friend was telling oth... Read full Story
brunasissyslavedolrj 2022-05-09 4,267 Crossdresser Group Sex Outdoor Fetish Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
75%
Singapore tranny sex
My ship was dry-docked in Singapore for 3 weeks, n i was lucky enough to meet a gr8 girl first nite ashore, Lin, half chinese/ half malay, n fucking sexy. I slept at her flat most nites and the sex was awsome. She shared with a girl called Meena, a hostess on Singapore Airlines, but until this speci... Read full Story
shemale lover 2011-11-20 4,321 shemales Group Sex interracial sex
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 8,652 Group Sex Cumshot Blowjob Big Cock Ebony gangbang 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 9,739 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
72%
Wie sich schlagartig mein Sex Leben änderte... Teil 1
ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... Read full Story
Holly Swallow 2019-03-20 7,563 Stockings Small Tits Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob blonde gangbang domination Interracial Sex Toys humiliation Homemade sissy girlfriend chastity cage Ass to Mouth cum in mouth chastity sissy amateur crossdresser fendom
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 4,797 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
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 4,989 shemales Group Sex Fetish
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 4,758 anal Group Sex lesbian
60%
A Sissy Boy is Made
By any measuring stick Greg Martin was a wimp, and a very submissive wimp at that. His wife of 14 years, Jaclyn, had discovered this even before the two of them were married. Actually, Jaclyn wouldn't have taken a second look at Greg, as most women didn't, had it not been for his submissive nature. ... Read full Story
shemale lover 2012-06-15 8,255 Cumshot oral sex sissy
100%
Becoming Sissy
I remember my first true and sober gay sexual encounter. The guy from the party that was my first BJ and first penetration was one of the closest friends of the group. He bought a house up north and 3 of the girls and me went to his house to help paint and work on some things. This was about a mo... Read full Story
xspeeny 2023-04-28 7,422 anal Amateur Bareback Blowjob Big Cock sissy cum in mouth
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,149 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 13,877 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
100%
Who's The Sissy Now?
Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going t... Read full Story
shemale lover 2012-11-14 6,829 shemale facial oral sex
100%
Afternoon Delight Chapter 3
When we got to the cottage, the girls stripped me of my jewelry and took theirs off and poured me into the shower. They washed the cum off of me and got me hard again. Damn, Ally and Carmen were all over my cock, giving me a work out. Needless to say, I came a few more times, and we got into the hot... Read full Story
shemale lover 2012-08-27 2,425 Group Sex facial sucking off
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 5,010 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
85%
A Sissy's New Daddy Chapter 2
I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece... Read full Story
shemale lover 2012-06-16 12,593 Creampie oral sissy
66%
A Sissy's Wish List
Boys, boys, boys. First off, let me tell you that I have a butt plug shoved so deep in my little tranny pussy right now. That might help to explain how depraved I might sound. I really need some cock in my ass right now! I am sitting here stroking my tiny little tranny clit right now thinking of how... Read full Story
shemale lover 2012-06-19 4,291 transformation submissive sissy
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 12,661 Group Sex Cumshot shemale oral
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 9,573 Crossdresser Amateur Group Sex gangbang Interracial transgender sissy bbc Black Owned owned white boy pimped force feminised BNWO
87%
Beginning of my Bi Life
Well It's all Started When I Was at 13 or may be 14 years old. I began to watch porn and reading porn comics and began to masturbate. I wasn't getting much privacy at my home so I was staying at my school even after my classes was over and when everyone was busy at after school Sport hours I masturb... Read full Story
Trapbomb1 2021-05-25 4,218 sucking Blowjob cum bisexual cd sissy femboy bi trap
100%
Oneness with the bodies
many years went into just fantasizing being with shemales. I was getting hornier day by day to try it out. But being in a relationship there was hardly any room or time for it. I once experienced it in bangkok and confirmed that I really can do it and actually love it. One day suddenly it was br... Read full Story
zyankhaan786 2023-05-30 6,217 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
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 7,775 Crossdresser Amateur Group Sex Blowjob Big Cock gangbang Lingerie
100%
The Invitation
"You see, we have to come up with something that would be so embarrassing for you that there is no way that you would ever show those pictures of me to anyone, regardless of how d***k you got, or how horny you got or how pissed off at me you were,” Sally went on. “Something that wou... Read full Story
shemale lover 2012-03-20 5,903 Group Sex crossdressing feminization
100%
A Natural Sissy Part 2
The Party Just before we reached the entrance, which was manned by a doorman, I said, "Now remember, Stacy, you just do what I tell you, and everything will be fine." "Ok... okay." His nervousness was showing, but that was to be expected. He had no idea what was going to me... Read full Story
shemale lover 2012-03-24 4,101 anal sex Creampie oral sex sissy
87%
The Intimate Dinner Party
Susan and I were filled with anticipation as we arrived at Victoria’s house. We had been invited to what the written invite referred to as a “Sexy and Intimate Dinner Party”. Victoria was renowned for her unusual, and always different, dinner and cocktail parties. She certainly ... Read full Story
shemale lover 2012-06-08 4,397 Group Sex Cumshot oral doggy style
88%
My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
Nicole_femboyCD 2014-12-03 20,806 anal Crossdresser Cumshot Blowjob rimming cd
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,469 Stockings anal sex Fetish Interracial sissy
50%
Downsizing Chapter 4
Dan and Stacy went to a couple of the “swinging” sessions in the weeks following the football game. They learned a lot about themselves and each other, but Dan still didn’t feel totally comfortable. He knew he was bisexual, because he enjoyed the men as much as the women, but somet... Read full Story
shemale lover 2012-11-10 2,739 Group Sex cum oral
77%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 71,374 Teen (18+) Crossdresser transgender sissy slut.trinity
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 16,290 Group Sex Shemale Fucks Guy Shemale and Girl Sex Toys
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,252 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
Sissy marathon session
I had a message come through on my Fabguys account from a Dom guy who was looking for a sissy Crossdresser to attend a private address for a group session he was trying to arrange. I eagerly responded and within a short period of time the date, time, and place was arranged. So last Friday the 25t... Read full Story
Sissy Kirsty 2023-08-30 5,170 sissy gangbang
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 4,231 Stockings anal sex Group Sex Blowjob
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 7,598 first time tranny suck stroking mutual sex
66%
Discovering Mistress Sarah's World Part 2
Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "ki... Read full Story
shemale lover 2012-10-03 5,473 cum domination Sex Toys sissy
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 13,571 Group Sex gangbang Interracial cd sissy
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 14,990 first time ass Cumshot suck cd sissy make up
63%
What are Friends For?
I was over at a friends house for guys weekend. I was up early Saturday and went downstairs to watch TV, so I wouldn't wake anyone up. Nothing was on cable, so I checked what else was on, Net Flix, etc.... There was Firestick, so I checked what movies were on there. I found one that was marked ... Read full Story
MARKUS6969 2018-04-09 7,588 Group Sex Masturbation Bareback gangbang sissy slut gay orgy
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 32,719 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,359 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
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 4,262 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,136 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,113 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
91%
Lake Surprise
After finals of my first year in college in a northern university, I was ready for some real relaxation back home in the warm south. During finals I had started thinking how nice it would be to borrow my brothers boat and hit the lake for a week. I talked my roommate into making the trip home ... Read full Story
shemale lover 2011-12-08 10,479 anal Group Sex Creampie
81%
Made me a slut
I spent my time online since I was 18 watching tranny porn and crossdresser porn I really enjoy a mix of both especially with a big black cock in between I found a movie with a ebony tranny with a big cock and a white sissy gurl with a nice sized cock also... They got dolled up together and all of a... Read full Story
shemale lover 2012-01-05 6,732 shemales Group Sex interracial sex
50%
A Married Marilyn
"Class is dismissed. Don't forget the project due…" "Huh, what?" Marilyn woke up disoriented from her nap. When she finally came to, she vaguely remembered some project for Intro to Computer Science, gathered her legs from the chairs in front of her, dusted off her b... Read full Story
shemale lover 2012-03-18 6,980 Group Sex Masturbation sucking Sex Toys
100%
A Sissy's New Daddy
Walking in the door the Friday after my eighteenth birthday, everything seemed great. My parents had gone out of town for the weekend and I was for the first time a truly free man. My older brother had decided not to come home for Labor Day holiday which I was kind of bummed about, we didn't get alo... Read full Story
shemale lover 2012-06-16 10,572 anal sex cum oral sex crossdressing
0%
Tara's Adventures
Part 1 I had met them on line. Marla 1st then her owner Mistress Olivia. We chatted for well over a year and had met for drinks. They knew of my submissive fem side and we had planned meetings on several occasions but things always developed that upset them. Then a period of time developed whe... Read full Story
shemale lover 2012-08-11 5,071 anal Group Sex oral domination sissy
95%
What Lies Beneath (Part 1)
A RENDEZVOUS WITH SUZY – What Lies Beneath (Part 1) It had been a busy last day of the week in the office and I had started something that needed a little more time to complete. The office was quiet with most people having already left. It was a great opportunity to finish with no interruptions or ... Read full Story
The Adventures of Mia & Seth 2020-11-03 14,712 Group Sex Shemale Fucks Guy bdsm Interracial Sex Toys foursome
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 11,520 Group Sex Cumshot Bareback Shemale Fucks Guy threesome Blowjob Big Cock gangbang domination Ass to Mouth cum in mouth golden showers golden shower
100%
Making my CD slut fantasies become real
Having an open mind and saying yes to a TS friends' idea has lead me to discover things I never even knew about myself. I’ve always been into kink, but my adventures as a CD have shown Me that I have filthy perverse cravings to satisfy with people I’ve yet to meet. I enjoy transsexual escorts and th... Read full Story
pinkybrown666 2021-05-20 5,179 Crossdresser Amateur Group Sex Creampie Fetish threesome gangbang Interracial cum in mouth blonde cd
57%
DADDY and SIR: my craving for older men....
"I would love to be fucked by an older man. my tight little ass needs a cock from an aggressive, top daddy. I love to dress sexy for my daddy and will do most anything to please. Just one condition: you have to cum on my face. I am a slim, 28 year old slut with a tight little ass and an addicti... Read full Story
shemale lover 2012-10-28 4,226 anal Group Sex Cumshot oral
92%
The Curse (Sissy Story) by sdvine
I wasn't really having a good time that night at the bar. Truth be told, I had been practically dragged out in the first place by my best friend Joe, who told me he was tired of me "sitting on (my) ass" every night "finding new ways to be boring." Quite frankly, if this is what qualified as being no... Read full Story
shemale lover 2015-02-27 6,760 ass Cumshot sucking cd sissy