Sort by
Relevancy

Free Stories

100%
What if it is always your turn?
So I'm on AFF and get a ping from a guy whose been wanting to give me a blowjob and see where it goes from there kind of line. I respond back, sure, want to get a drink, I would love some Sake. We met down at the local sake shop, I am uncouth, I only like warm regular sake. I get a large to share an... Read full Story
smtmsbrianne2 2023-10-17 6,299 anal Cumshot Bareback cum in mouth
100%
Lola Chapter 5
Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... Read full Story
BellaBeau 2023-10-30 6,387 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
50%
Massage House Call
I answer your ad on doublelist for a massage. Although it mentioned a “happy ending” for me, I’m in a very submissive mood lately, so I’m thinking I’ll get a good massage and if he wants me to blow him, it’s a bonus. You walk in my condo, say hello and tell me to go to the bedroom, strip down, wr... Read full Story
cdtampa4u 2024-09-18 1,343 caught panty sissy condom to bareback
100%
Massage House Call
I answer your ad on doublelist for a massage. Although it mentioned a “happy ending” for me, I’m in a very submissive mood lately, so I’m thinking I’ll get a good massage and if he wants me to blow him, it’s a bonus. You walk in my condo, say hello and tell me to go to the bedroom, strip down, wr... Read full Story
cdtampa4u 2024-09-18 1,641 caught panty sissy condom to bareback
71%
My first Bareback
Ron and I had been talking online for a few weeks now. We wanted to be comfortable, and make our intentions clear with one another. He was going to give me my first bare back sex, so i wanted to make sure it would be okay. We finally decided to meet last weekend. Through the course of our conversati... Read full Story
shemale lover 2011-10-06 3,731 anal first time shemales
100%
Transsexual Heaven
I grew up in a small town, about an hour north of New York City. I had spent lots of time with Playboy and Penthouse magazine, but was not really active sexually through my teens or college years. I mean, I had steady girlfriends, and had sex, but I wasn't a Casanova type, chasing a different wo... Read full Story
shemale lover 2011-12-19 8,114 suck transsexual handjob
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,803 anal shemales Group Sex
100%
Fender Bender Chapter 7
The main Characters are as followed: My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I turned 18 a few months ago. Gary is almost 6', 185 pounds. He has short blonde hair and dark blue eyes. He has a nice tasty 7 1/2 inch cock... Read full Story
shemale lover 2012-07-27 3,519 Creampie ass fucking domination oral sex sissy
89%
The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
Tvtrinity 2021-04-07 22,322 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
81%
My 1st time with a man while dressed and 1st anal
My 1st time with a man while dressed and 1st anal The following story is true. I have been dressing in my wife's sexy clothes at home off and on for a while because I love the feel of hose and panties. My wife and I are swingers, actually we do mostly cuckold swinging but I am free to be with... Read full Story
gennipher 2017-04-11 18,777 first time interracial sex crossdressing black cock cd bbc
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 5,756 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
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 4,197 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
88%
Alex and Jon
Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... Read full Story
Jon Paul 2022-09-21 5,814 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 4,115 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Escorted
Hello! Would it be possible to have you send an escort over? A beautiful escort. Not a plain looking woman but someone special, ok? .... Ok, got it. Thanks. I opened my door to a very very sexy woman. Dressed in a tight short dress that hugged her hips and accented her nice size titties. A very bea... Read full Story
Curious_billy 2024-03-13 6,790 anal Amateur Bareback Creampie Shemale Fucks Guy Blowjob Homemade
100%
an old friend
I hadn't heard from one of my oldest friends Dave for many years, we used to play in a band together, hang out and occasionally watch porn together after a night out drinking, with Dave usually falling asleep with a lit cigarette in his mouth, he is about 5'7'' medium bordering on at... Read full Story
NWLexxxi 2024-12-26 1,427 anal Crossdresser Bareback threesome breeding mmf
92%
Finally, My First Tranny!!!
I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty horney since my doctor is a female and I had a complete physical so she and her nurse were in the room with me. I got to the train station to go back to Willow Grove and was standing on the platform when... Read full Story
shemale lover 2015-07-19 34,995 anal first time shemales
100%
A Day Driving in the Country
Day off, out for a drive. What a predicament, standing on the side of the road next to my open car door with my hands straight up in the air; looking down the barrel of a Highway Patrolman's handgun. I'm about to pee my pants, that is what little bit of pants I have on. The Highway Patrolman is d... Read full Story
shemale lover 2012-02-26 4,645 Fetish Blowjob crossdressing
100%
Neighborhood Restaurant Surprise - Kimi
I - The Meeting In the neighborhood restaurant I frequented weeknights after work, I had developed a friendly relationship with several of the college kids who worked as servers. Always having been attracted to the most feminine and petite of girls, dark, almond shaped eyes being a super plus, I ... Read full Story
shemale lover 2012-04-11 5,608 anal sex Cumshot fingering oral sex small breasts
50%
Alex One: House Sitting for a Friend
Sorry, this is a little rough. I've tried expanding the original version but ... i dunno. Anyways this should be a continuing series of some sort. Alex One: House Sitting for a Friend. By Alex Shouse. My friend Karen had worked her way through a somewhat bitter separati... Read full Story
AlexShouse 2012-07-12 4,252 dildo oral transvestite sissy
100%
A Weekend Together Chapter 1
My fiancée and I, decide one weekend to indulge in my fetish of cross-dressing. We rented a hotel room down town across the street from the local gay club for Friday and Saturday night. I checked in when I got off work Friday afternoon upon entering the room I stripped of my male clothes and ... Read full Story
shemale lover 2012-07-23 4,168 Fetish oral Sex Toys crossdressing
90%
In Hose and Heels for Daddy
It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and... Read full Story
shemale lover 2012-09-30 7,847 Fetish jerking crossdressing
100%
Thai Ladyboy goddes in Tokyo and a cheap love hotel
This is a real account of my meeting last week with a beautiful Thai ladyboy working at a flashy show at a night club in Tokyo. Written as a not to her. Hope you like it. You sexy ladyboy goddess, I must say you have the most beautiful body. When we first started drinking wine and talking ... Read full Story
lblover77 2012-10-09 10,348 anal Ladyboy oral
93%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 40,609 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
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 62,874 suck Bareback Asian Ladyboy ass fucking
83%
How Kevin Became Finesse
Monica went out with JJ! He was a black buff guy who taught karate where she took the kids. He drove a yellow corvette and liked to wear shirts with the sleeves cut off - to show off his big tattooed arms! All the young blonde girls were on his jock, but he had the eyes for Monica. She kept protesti... Read full Story
Kevyn-JeanneHarris 2015-12-20 4,942 sissy cross dresser cuckold
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 10,736 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
TG Girlfriend moves in
Monday morning 6:00 am and I am just awakening, and I realize a naked body beside me has her arm around me, we are both naked. My wife Lydia is out of town to a seminar, and this adorable brunette perky tits and lovely eyebrows, beautiful lips slightly pink, sleeping beside me. Joanne and I had spen... Read full Story
Jon Paul 2022-01-18 5,747 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
Blind Date
XtinaSmith2017 Anthony awoke to a piercing buzzing tune, a nice enough melody, but one he had come to despise shortly after he had made the mistake of making it his alarm. The culprit, his smart phone, was plugged in on the nightstand beside him and was in the process of making him gleefully aw... Read full Story
Gwapo67 2022-07-01 6,156 Bareback Creampie Shemale Fucks Guy Blowjob
100%
First Date With Daddy
My Dream Date. It hasn't happened yet, but a girl can hope, this story is very short story based on my fantasy's. It was Sunday night and I had my first date lined up with daddy. We hadn't met, but we had spoken online at depth and exchanged numbers. I had sent him a couple of pic... Read full Story
SEXYBADGIRL 2023-03-17 5,523 Crossdresser Bareback Creampie domination
100%
Ravaged by Daddy
For anyone who loves wearing high heels and dressing up to get ravaged by your hungry Daddy. I imagine you laying on your side as I run my strong hands up and down your smooth, soft legs and across your feet. I slowly slide them upwards until I'm caressing and squeezing your thighs. You watch me ... Read full Story
TheWinkster 2023-08-29 5,793 anal Cumshot Bareback Creampie Guy Fucks Shemale
100%
A Win-Win
A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... Read full Story
Brina Giselle 2024-03-31 4,858 anal Stockings Crossdresser Blowjob pantyhose kissing salon
33%
Click, click, click....
Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will th... Read full Story
shemale lover 2012-06-09 5,873 anal Cumshot oral deepthroating
88%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 68,584 Fetish shemale oral feminization
83%
Yes Sir
I've been meaning to write this story for some time. It could have easily happened had I taken the initiative but instead, I chickened out. It remains a favorite fantasy of 'what if' though. I hope you enjoy. Saturday evening and I'm sitting in the living room of my small mobile home. Nothing to ... Read full Story
shemale lover 2012-08-21 4,144 domination crossdressing
100%
Brazilian Discovery Chapter 2
Chapter 02: First days in Brazil The tub was so large that it could have been a small swimming pool. Joan plunged into the water and started to lick Barbara's pussy underwater. When he rubbed the tip of his nose against Barbara's clit, she mightily climaxed several times in a row! Sometimes, inst... Read full Story
shemale lover 2012-08-25 4,077 Group Sex Cumshot oral sex rimjob
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 6,093 first time Fetish cum oral crossdressing nylon
100%
Whitney's Way
My arms were stretched over my head as I finished hanging the last sheet of drywall. Another step closer to the end of the two year process of renovating our first house, it was hard to conceal my sense of pride at turning a worthless wreck into the nicest place on the block. But as soon as I heard ... Read full Story
shemale lover 2012-11-18 9,067 Cumshot oral sex kissing
100%
An unexpected kiss under the rain
Army Bear left that morning leaving me horny as hell. I couldn't go back to bed without playing with myself for a while. I opened my Pandora box and I took out my 9 inches, big dildo. I played with it for a few long minutes, burying it all deep in me thinking of him. Doing a few hits of poppers, I f... Read full Story
HotVersatileTs 2011-10-05 5,123 sucking domination foreplay cd
50%
Blue collar Master, white collar slave
I sit on the couch in my owner's house, dressed every bit the slave I am. My body from the tips of my toes to my eyelashes is completely and permanently hairless, smooth, soft and beautifully tanned. My upper body is clad in a thin, soft and pink rubber T-shirt and my ass is clad in a pa... Read full Story
shemale lover 2012-01-12 10,106 torture extreme fiction bondage and discipline
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,770 hardcore Cumshot bdsm oral sex
100%
But it's just two guys right?
CD's and TV's are not really chicks they are guys and they have guy sex drives! Unlike many online Cyber Queens as I call them. Years ago I did do some cross dressing. Unlike those AOL and Yahoo frauds I really did dress up and unlike them despite digital cameras being new things and ve... Read full Story
Jennifer4u727 2016-11-03 16,990 first time cd tv hotel Straight Guy
75%
Tales of Old China
This is a true story by the way. It doesn't matter too much, but I guess it's worth you knowing that. My name is….. Well my name isn't important. What's important is that I'm now in my late 20's, male, tall, fit, dark haired, blue eyed and have been told that I'm good looking. Got that in ... Read full Story
shemale lover 2011-09-30 3,994 anal sex asshole Creampie
100%
Screwed
Randi's excitement grew as she walked outside to her car. She'd been preparing for this all day and dreaming it up for weeks. She began the day by showering and shaving her legs, followed by putting on a nice red nail polish on her fingers and toes. She went to her dresser and picked out a black ... Read full Story
shemale lover 2012-09-24 3,516 Cumshot suck domination cum swallowing
37%
First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
shemale lover 2013-07-17 6,589 first time Crossdresser Fetish Mature bisexual
75%
A Futa Futcha
This story depicts a fetish know as Futanari Fuatnari: A type of Hentai, most often depicting hermaphrodites or females with male sex organs. Also known as Dickgirls. Transformation Futa is a long standing kink of mine, though it has been a while since I indulged. The major difference is that ... Read full Story
shemale lover 2011-10-29 9,209 Fetish Futanari dickgirl
83%
Abducted and Turned Out Chapter 1
About four years ago, I decided to go out for the evening to a local club that tgurls hung out at. I was a regular there, and had been going there for some time with a regular circle of TG/CD girlfriends that I hang out with. I was already excited when I started to prepare myself in the late afte... Read full Story
shemale lover 2012-08-10 5,574 Crossdresser blonde oral sex cum swallowing
63%
Julie's First CD Night on the Town
There was a parking lot that was out of the way where I changed into my set of girl clothes for my night of adventure. The nylon underwear was tight and sleek, I had a raging hard on as I drove into town. I had been planning this night out for quite a long time and was hoping to get my butt well ... Read full Story
shemale lover 2012-09-10 4,782 Crossdresser Cumshot condom sex heels
100%
Hose and Heels in School - I'm a bad girl
A knock on the door? Who could that be? After all it was mid-evening on a Friday night and I certainly wasn't expecting anyone. I was looking forward to a night of relaxing on the sofa and nothing more. I opened the door and there stood Liza, staring at me with a smile on her face. "U... Read full Story
shemale lover 2012-05-11 3,431 anal sex fingering spanking crossdressing
100%
Lady In The House Ch. 05
A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... Read full Story
✘Transensual✘ 2019-02-25 5,037 Crossdresser domination PRISON prison sex
50%
Caitlin and Mistress Vicky Chapter 3
I was sitting nervously in front of the mirror in the newly decorated guest room. Chad was set to arrive in half an hour. My wife was getting ready in what was for now our bedroom. She had told me to dress up for the occasion, though I was still to wear my maid's outfit. I opened my jewelry box and ... Read full Story
shemale lover 2012-03-01 3,746 suck Fetish fuck domination
87%
Seducing Daddy
I had started crossdressing when I was 5 years old when I went trick or treating as Princess Leia for Halloween. The first time I pulled on a pair of pantyhose, I was eight years old. I could not understand how a piece of clothing that I could crumple into the palm of my hand could cover my mother's... Read full Story
shemale lover 2012-08-01 7,618 Cumshot oral sex crossdressing
100%
Dracula's Bite
It is amazing the things a man will do to get laid. It was Halloween and I was being dragged to a costume party thrown by a few of my girlfriend, Caroline's friends. Although Caroline was a prim and proper insurance underwriter during the day she hung out with a rather arty crew of liberals. The... Read full Story
shemale lover 2012-11-11 5,302 cumming fucking kissing
50%
The Greatest Lie Part 11
"En Francais", they say "plus ca change, plus c'est la meme chose:" the more things change, the more they stay the same. When Tran and I got back to Minneapolis from our trip to Thailand for our sex change operations, it was every bit as dark, frigid and depressing as it had been... Read full Story
shemale lover 2012-01-20 5,582 cum transformation erotic encounters
100%
A Special Girl
Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the sm... Read full Story
shemale lover 2012-06-30 5,854 Cumshot Blowjob oral sex
100%
Double Take Chapter 3
Sandy and Ashley switched off the television and stared at one another in disbelief. Normally, they didn't stay up to watch the network telecast of Wet Girls, which came on at 10:00 on the west coast. After all, they had to get up at 5:00 the next morning. But they knew the entire country would be t... Read full Story
shemale lover 2012-11-03 3,422 Stockings Fetish feminization