Sort by
Relevancy

Free Stories

88%
Caught Crossdressing by a Real Man
This story is a continuation of night club cum slut. Ever since I first wore panties for a boyfriend, I had built up a collection of lingerie. I gradually worked up from panties to the most erotic lingerie I could find. My fascination with cross dressing went a little further with a new fetish f... Read full Story
shemale lover 2013-01-17 35,143 Crossdresser sucking Lingerie ass fucking ass fingering
88%
How I became a cute femboy CD part 3
about forty-five minutes after midnight and found two boys sitting on opposite sides of the couch playing a video game and teasing one another about how bad the other one sucks. My mom talked to us for a while and went to bed and by this time it was almost two am and we were tired so decided to go ... Read full Story
Cute_Femboy 2016-04-05 6,751 first time fingering crossdressing cd sissy
50%
Fluffy Takes a Walk
It neared dusk at ValueStar Motor Lodge which sat smack dab in the middle of the hood. Inside of Room Twelve, an average height, chubby, brown-skinned femboy repeated the douche. He let out the stream of lukewarm water and turned around to study the toilet as the hip hop music blared in the backgrou... Read full Story
Faggyboi and Puzziboi 2023-04-09 4,894 Crossdresser Big Tits Guy Fucks Shemale big ass sissy femboy BB fagg faggyboi puzziboi
16%
Current Fantasy
I really wanna get fucked for the first time and my dream way of doing it, always wanted to do a porn. The dream is that I go there and get done up in such a way, I am unrecognizable, just looking the best. Have a tranny come in and do my make up, the way she likes it and gives me a preview of what ... Read full Story
martley 2023-06-30 4,797 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,320 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
The Big Tiddy Goth Girl
Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... Read full Story
KaceyKlarissa 2024-02-23 3,138 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
100%
Towel Boi: Agreement Signed
Ralph moved the mouse to wake up the computer. He navigated to his legal docs account and downloaded a generic pre-existing relationship agreement. He asked for the spelling of the new hire’s first and last name. “First name K-A-S-E-Y. Last name S-T-E-V-E-N-S.” “Got it,” acknowledged the owner. ... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,485 Crossdresser Bareback Creampie Blowjob Guy Fucks Shemale Interracial small cock big ass sissy femboy
100%
Dressed for Suck-cess
I had met my new friend just before Christmas, and we had already played a couple of times before today. However, it kept getting hotter, and today it was just too hot not to write about it. If you've read any of my other stories, you'll know that I'm an older bi married white male living in wes... Read full Story
shemale lover 2013-01-22 3,948 Crossdresser sucking Blowjob ass fingering rimming
92%
My shemale girlfriend
I met Andrea out side a bar on the west end, she was outside smoking a cigarette, I started a coversation with something stupid like "you come here often?" she laughed and we started talking had a couple of drinks and exchanged numbers. Andrea is about 5"10", shoulder lenght dark... Read full Story
shemale lover 2013-04-26 8,556 Cumshot suck fingering cum swallowing stroking
88%
How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
shemale lover 2013-07-19 6,165 Cumshot Masturbation transsexual oral sex ass fingering
96%
The Magic of the Lamp
"Are you serious? I'll give you $20 bucks for that thing!" said Tommy. Tommy couldn't believe how lucky he had just gotten. Thrift shops were notorious here for ripping people off, but this store seemed to be giving him a pretty good deal! "Yessir. We have had that little lamp f... Read full Story
shemale lover 2013-03-05 8,369 sucking Blowjob domination big boobs ass fingering
100%
Hi, My Name Is Hollie Chapter 2
Hi, everybody! It's me again. Hollie. You remember, the 19-year-old herm-girl with a buxom older sister? It's been a while since I last wrote, but wow. Things are moving right along. And in some fun, unexpected directions! Emillie and I have been spending more quality time together, playing around a... Read full Story
shemale lover 2012-12-19 4,155 Cumshot Masturbation shemale and shemale jerking ass fingering
94%
Taken Chapter 1
Georgia pulled her Mercedes out of the gas station in Albuquerque back onto interstate 40 heading east. It was a long drive ahead to Chicago. She hated traveling alone, that was for sure, but the move to the office back east made it necessary. It was either drive there or sell her Mercedes and buy a... Read full Story
shemale lover 2013-01-18 7,032 Cumshot Big Cock ass licking big boobs ass fingering
95%
Dana becomes a woman
All her life, Dana had felt different. Born a boy, she always preferred dressing in girl clothes and playing girl games. She was mistaken for a girl from the time she was toddling - her feminine face and manner always convinced people. By the time she graduated high school, Dana discovered her ma... Read full Story
shemale lover 2013-07-20 4,432 Crossdresser Cumshot Masturbation oral sex ass fingering
90%
Collette's Property
I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade ... Read full Story
shemale lover 2012-12-19 7,703 anal Crossdresser Blowjob domination ass fingering
92%
Proud To Be A Sissy Chapter 6
It was still early and I wanted to enjoy the feeling of being dressed in my shear hose and garter belt, tiny g-string panties and matching bra and the form fitting shiny black mini dress that barely covered my stocking tops for as long as possible. So I spent some time doing some domestic chores and... Read full Story
shemale lover 2012-12-24 6,060 sucking domination ass fingering deep throat cd
100%
Mommy Writes for Mandy
We work in a big corporate office. I am the owner of the advertisement company and you are my secretary. You are fully Mandy. You started taking hormones years ago to fully become a girl. Your hair is grown long and you have little a cup breasts and chose to always wear dresses, skirts, frilly blous... Read full Story
shemale lover 2013-03-12 4,493 Teen (18+) Crossdresser Cumshot Lingerie ass fingering
100%
Dianne The Trans
It all started a few weeks ago, I watched as she layed on the beach tanning her sweet body. She looked so hot wearing that pink bikini. Damn i wish i knew her name, or where she lived, maybe shes here on vaction. I don't think i've seen her before, but she does look familiar. Finally getting the cou... Read full Story
shemale lover 2013-07-19 3,323 hardcore anal sex Cumshot oral sex ass fingering
50%
Quickie
So I arranged to meet someone online to come round. I was in fishnet stockings, heels, bra and panties. I was dildoing my ass to widen it whilst I waited. When he knocked on I let him in and showed him to the bedroom. Once in, I got on my knees and sucked his floppy cock until it was hard. Precum wa... Read full Story
mikey1993 2016-04-05 2,473 anal ass fingering doggy style crossdressing
100%
Fucking and Getting Ass Fucked
Playing with Lisa. I have been seeing Lisa for a few years. We have what I call a "Role Play" game that we both love to do when we meet. It almost always starts the same. But it does have a different ending most of the time. It was early March and the weather was cold. I was driving ... Read full Story
shemale lover 2012-12-04 4,453 tranny fingering oral sex
96%
New Horizons
Pete always was very open sexually speaking. "Don't knock it if you haven't tried it" was his watch-phrase when it came to sex. Being alone in a faraway land had just emboldened him a little more. Lately Pete had found himself fascinated by transsexuals whose pictures he'd seen on the ... Read full Story
shemale lover 2012-12-23 4,723 sucking dildo ass fucking ass fingering handjob
94%
Proud To Be A Sissy Chapter 2
As I reached down to retrieve my clothes that Mr. Clark had thrown at me there was a bright flash of light. Without thinking I turned my head towards him only to be blinded by another flash from his Polaroid camera. "What are you doing?" I asked. "Just wanted to capture the m... Read full Story
shemale lover 2012-12-23 7,671 Crossdresser sucking ass fucking domination ass fingering
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 6,950 Cumshot sucking ass fucking Guy Fucks Shemale ass fingering
100%
A Change with Sam
I met Sam three days before her birthday. At the time this information was nothing to me, and she was just a shadow within the day to day of my life. The school cafeteria was busy the day we met, though I cannot recall exactly why. Some sort of event, one of the many ways my school sought to break f... Read full Story
shemale lover 2013-02-22 7,021 Cumshot jerking ass fucking big boobs ass fingering
92%
A very special lady
I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and wil... Read full Story
shemale lover 2013-07-18 5,707 Stockings anal sex Shemale Fucks Guy ass licking ass fingering
97%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2013-07-22 10,159 transsexual oral sex ass fingering kissing
95%
How I became a cute femboy CD part 2
The game of husband and wife Kevin and I played went on for a little over 2 more weeks before we decided to go even further, I say we but it was Kevin who seduced me into it. We got together in our game as much as we could and it was a lot. I would always dress for him in various outfits and my ... Read full Story
Cute_Femboy 2016-04-05 11,829 first time oral sex nipples crossdressing cd sissy
75%
Memoranda From Mr. P
Mr. Reddie used to call me Petro, as a short familiar name; his sly friendly way of reminding the two of us of my thick lengthy cock. Mr. Reddie maintained, when it was hard and erect, my cock looked and felt as lovely as Italian marble, hence the contraction of the Italian for stone: Petro. Whi... Read full Story
ColonelSaint 2012-03-19 3,340 Group Sex cum oral femboy
100%
Alone at home
Living with my religious parents didn't provide many opportunities to spend time alone to enjoy myself. Only openings I found where, when showering, and occasionally when my parents travel, though that was not very often. I shared my room with my lil siblings, and since they were young and curious, ... Read full Story
Sara M. 2024-01-16 5,414 solo Lingerie small cock Homemade sissy femboy
72%
Brenda & Bry
I like to write stories that involve kids having sex. And one of my favorite subjects is kids having incestuous sex. One story, about a brother and sister, attracted the attention of a 15-year-old boy when I uploaded it to the adult BBS that I regularly called in Reston. It seems that one of the ... Read full Story
ColonelSaint 2012-03-19 7,810 femboy dildo fucking
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 4,137 sucking Blowjob cum bisexual cd sissy femboy bi trap
55%
story of Jojo
Some find it confusing of who i am or what i am, including me. i found some kind of definition: femboy A young boy who presents extensive feminine mannerisms and actions often blurring the line between a boy and a girl. Can be confused with a cross dresser, but it usually refers to boys at v... Read full Story
jojo58654 2017-09-12 10,259 Amateur transvestite strapon cd femboy
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,276 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
66%
You Just Don't Care...
“Oh, naw! I’m straight,” the slim, sinewy-built man replied matter-of-factly to revelation. “What’s that got to do with anything,” cooed the milk-chocolate-complected vixen, playfully grazing the man’s hard chest. “Damn, why you ask it like that,” he scoffed. “Like what,” the sing-songy-voiced c... Read full Story
Faggyboi and Puzziboi 2023-10-19 5,505 anal Crossdresser Ebony Guy Fucks Shemale sissy femboy bbc faggot faggyboi puzziboi
50%
Towel Boi: Heading to Work
“Goddamn, white boi! You got the best fuckin’ ass,” declared the father of two. His steel manly form perspired as he moved hard into the bottom. “Look at all that butt shake! Twerk it for me, baby boi!” “Yes, sir,” cooed Kasey, gyrating rhythmically. “Hell yeah! It’s like fucking two big ol’ ma... Read full Story
Faggyboi and Puzziboi 2023-11-17 5,580 anal Crossdresser Bareback Creampie Blowjob gangbang Lingerie Guy Fucks Shemale Interracial sissy femboy bbc
85%
Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
shemale lover 2014-09-17 60,435 suck Bareback Asian Ladyboy ass fucking
90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 12,138 first time cumming crossdressing cd sissy cumshot in mouth
0%
My first experience
Forget to share second part, thats why i posted again. I am a bisexual(passiv), i was born in muslim county and being bi is like crime. Thats why i never had any sex with a guy. I was just mastrubating and fingering my ass, sometimes was using cucumber . Finaly i had a opportunity to go Europe and... Read full Story
Private_love 2022-07-22 3,828 Crossdresser bisexual femboy bi
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 20,636 anal Crossdresser Cumshot Blowjob rimming cd
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,106 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
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 2014-12-03 189,463 first time Crossdresser suck Blowjob oral cd
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 4,608 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
77%
How I became a cute femboy CD
Chapter 1 Hello, my name is Natalie…well that’s what I named myself when I dress. Before I get started with my story about myself and when and why I started dressing and my first sexual encounters, I would like to give what I hope will be a brief rundown of myself. As I mentioned my name is Na... Read full Story
Cute_Femboy 2016-04-05 45,353 first time crossdressing cd sissy
100%
A real fuck doll !!
I'm just back from a double date with my ex and his friend and yes im still rolling on molly but I handled them both so good I'm sooo proud of myself! It was effortless really, my brain kinda switched off coz there was cock infront of my face always and one behind me and I realized my body was autom... Read full Story
MayaTsarina Bimbo 2023-08-15 4,266 big ass sissy femboy bimbofication
42%
First time with a Shemale
I have been curious about shemale's/tranny's for a while now. I finally met one in my small hometown I live in. She was ebony and had beautiful big fake breast and she was so Hot 🔥🔥🔥 and beautiful. We went to her place and she sucked my dick so fucking good and let me beat out her right ass twi... Read full Story
TrannyWarrior 2023-08-30 6,381 first time Fetish Ebony femboy ebony shemale Sexy black trannny
20%
Extend Sissy
Extend pls! https://sissy.fun/sissy-bimbo-whre-mayatsarina-chained-up-big-butt-tranny-wth-toy-in-asshole/ , https://xxxposed.fun/prostitute-fucktoy-slave-bimbo-mayatsarina-for-rent-cheap/ , and also this https://xxxposed.fun/dumb-bimbo-whore-may... Read full Story
MayaTsarina Bimbo 2024-03-14 6,441 big ass sissy femboy Exposed Sissy exposed
50%
sine qua non: anal/vaginal pleasure
One thing's for sure, my desire is to be fucked and to fuck... And it's in this order of things that I've been wanting to fulfil my fantasies for the last two years. I'm not too fussy about choosing my partners, but luck has always smiled on me when it comes to finding the right one. However, over t... Read full Story
hippocampus_171 2024-04-05 1,389 anal solo Amateur Mature big ass sissy femboy
50%
jouir anale/vaginale mon ‘sine quoi non’
Quelque chose est sûre, mon désir est d’être baisée et baiser… Et dans c’est dans cet ordre des choses que je veux réaliser mes fantasmes depuis deux ans. Bien que je ne sois pas trop pointilleux pour choisir mes partenaires, la chance m’a toujours souri pour trouver le bon. Toutefois depuis quelqu... Read full Story
hippocampus_171 2024-04-05 94 anal solo Amateur Mature small cock big ass sissy femboy Vintage
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 1,774 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
50%
Pa-mie sex-agénaire
Luxure frénétique d’une pa-mie sex-agénaire; entre rêve et réalité Je n’avais jamais fantasmé de mec viril, même après avoir offert ma virginité; mais à une fabuleuse sissy. Avant mon Ѐre, mes préférences de fantasmes étaient toujours avec des lui-femme glabres, idem concernant mes relations d’aprè... Read full Story
hippocampus_171 2023-07-09 585 anal Amateur Group Sex Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy Ass to Mouth
50%
House Guest
“Hello, baby,” the septuagenarian smiled. “Hi, Misses Pearson. I was just calling to say hi and tell you I got that job in Brennan!” “That’s wonderful,” she mused. “Bill!” “Huh,” the woman’s husband grunted. “Jenna got the job!” “That’s good,” he coughed and went back to watching his favorite t... Read full Story
Faggyboi and Puzziboi 2024-04-26 731 Crossdresser Blowjob Ebony Lingerie Guy Fucks Shemale sissy femboy
100%
"The Arrival" The silly little sluts first Freedom of touch
Based upon Khloe Kay, my imagining if I could be her. { Unedited} a habit to arouse my deepest desires. -Araina Sinclair, Sissy Slut to be. Hope you enjoy. He started to pound my ass, quicker and quicker. Deep long strokes. My boi pussy stretched he started to pull out and slap his head . In... Read full Story
Araina 2021-02-15 1,763 anal Cumshot Shemale Fucks Guy Fetish Blowjob cum Lingerie slut sissy femboy handsfree Khloe Kay
100%
IRL: Magic City Classic
I get many requests asking me to share more of my real life experiences. Several of my stories contain elements of things that actually happened to me. But, I’ve decided to put together a new e-Book of my personal sexcapades. So, in that vein, here’s the first installment of my ‘In Real Life’ (IRL) ... Read full Story
Faggyboi and Puzziboi 2023-07-14 4,240 anal Crossdresser Bareback Blowjob Guy Fucks Shemale femboy bbc faggot dl puzziboi faggy
100%
Assertive Wench
You Can Take It If You Try This past summer the deli and filling station a couple of blocks from my residence hired a new cashier. She is supposedly 23 but she looks like she belongs in somebody’s high school. She is a 90 pound cuties pie with long hair, an hour glass figure and those calves on ... Read full Story
DRILLMASTER 2023-10-26 4,535 femboy
50%
I kneel in front of Dominatrix Persephone
Fan Mail. I kneel in front of Persephone.. She looks amazing in Her latex catsuit, but there is something else eye catching. Chance, Persephone huge hó rse c... It looks intimidating in picture, but just think how it must look when it is right in front of your face!! Holding it in my sissy hands, i... Read full Story
Dominatrix Persephone 2024-05-01 411 anal Interracial Mature Homemade sissy femboy teen (18+)
100%
HE DIDN'T KNOW I WAS TRANS...
I'd worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
mika96 2023-05-11 6,273 anal Amateur Bareback Creampie Blowjob femboy Ass to Mouth