Sort by
Relevancy

Free Stories

75%
All Night Forced Sex Part 2
When I woke up I was in a darkened room and a woman was standing in front of me she was the most stunningly beautiful woman I'd ever seen before in my life. She's statuesque, about 30ish, with long red hair almost down to her perfectly shaped ass. She's wearing all black - a vest that pushes her bea... Read full Story
shemale lover 2011-10-09 3,306 shemale domination spanking
80%
My 2nd tranny date
My second transexual Encounter was years later my First, I was sixteen At the time. And I was driving home from my girlfriends. I was living at my parents, my curfew was 2 am. That nite I had taken my moms fleetwood with me. I left her at her house and I had a hard on. On the way back I passed by 8s... Read full Story
shemale lover 2012-03-18 2,513 tranny cum condom sex
100%
Pleasure Zone =D
Frank stood in the middle of the room looking at all the women none of them really caught his. Eye until he looked at the lady sitting at the bar her smooth looking. Olive colored skin her twany hazel eyes the non reaviling powder blue teddi she had on. Really brought out her eyes. Her thin lips an... Read full Story
shemale lover 2012-04-09 1,783 shemales oral sex jacking off
100%
My first time wearing sexy lingerie Part 2
I could not wait to get home from school the next day after wearing my moms sexy panties the night before. No one was home so i could have fun. As soon as i got into my room i took off all my clothes and went into my moms bed room to see what I could put on. With my mom working at Macy's in... Read full Story
shemale lover 2012-09-15 5,276 first time Cumshot Lingerie jacking off
100%
Decisions, decisions.
So if you have read my stuff I’ve posted before I was with a tranny named Nicole for awhile but she left for work last year so after she left I actually started dating normal again went back to girls but never forgot her. I’ve hid the dildo and all my secrets from my current girlfriend for almost a ... Read full Story
Duke04 2019-07-25 7,587 Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth
80%
I got humiliated in a catfight
Im a crossdresser and I am very feminine and extremly dainty. I was attracted to a man at a park I went to. He knew I was a crossdresser. I would always say hi when I saw him, but that was it. One day he asked me(on a rainy day as I was getting in my car), do I have a boyfriend am I bi, he wanted to... Read full Story
Kaylamoore994 2023-03-26 5,479 Crossdresser Outdoor Masturbation Fetish Ebony Ladyboy Lingerie humiliation fight sissy crossdresser catfight
90%
Night With Shana
This meeting took place in Los Angeles, CA. I’m sure many of you are into shemale porn movies and will know who Shana is. For those of you who don’t know her, she is a gorgeous white shemale with long brown/blondish hair, big tits ( think there is some silicone in there — but who... Read full Story
shemale lover 2018-01-14 10,967 tranny suck face fucking
100%
A Lucky Meet
She was beautiful, I saw her across the street, a complete bomb shell and I knew that I had to talk to her. I approached her and she tells me 500$. I was shocked! I pulled out my wallet and paid her immediately, blonde blue eyes double D’s about 57 130 pounds what more could one ask for. We... Read full Story
shemale lover 2011-08-26 2,700 licking sucking shemale
94%
My Girlfriend's Cock
I have had many girlfriends over the years but the one I have now is very different. Her name is Kim and she has a cock that is as big around as a beer can and about 8 ½ inches long. Kim is a beautiful woman with a cock. When we first started dating I had know idea that Kim was packing a b... Read full Story
shemale lover 2011-09-08 6,504 asshole Creampie fingering
100%
My First and Last Girlfriend Part 2
I dressed up, filled with thoughts of guiltiness about what had just happened! I went to the bar and ordered for red rum, thinking of myself getting pumped up my ass from the girl I had made a woman! What a shame! She had just fucked me like a sissy and what was even worse was the fact that as I... Read full Story
shemale lover 2011-09-28 2,936 asshole pussy Sex Toys
50%
Something More To Her Part 2
As they entered carloses room, none of the 5, except carlos, of course, could believe how nice the room was next to the rest of the apartment. a queen sized bed with red lace blankets, a flat screen TV with at least 250 channels, hundred year old antiques, gold, and, the thing that stuck out the mos... Read full Story
shemale lover 2011-10-27 2,127 shemales Group Sex interracial sex
100%
Tgirl Fantasy Cum True
Before the gay man fantasies were the tranny ones. Looking back, I think I was drawn to them because they have the feminine bodies that I always loved mixed with cocks, the male body part that drove me crazy. 3 years ago I was jerking off to tranny porn online everyday. I loved the very hung t-girls... Read full Story
shemale lover 2011-12-07 3,640 first time shemales hardcore
100%
Date Sex!
I wake up, my head throbbing. "Ugh, what a nightmare." I think to myself as I try to shake the sleep and cobwebs from my mind. My head splitting with a headache, it starts to register that something doesn't feel right. "It was just a dream Mar..." I tell myself as I t... Read full Story
shemale lover 2012-07-24 4,277 shemale domination oral sex
100%
My Fantasy #1
I had been secretly cross dressing for years without anyone knowing about it. I got pretty good at hiding it even when I would wear a hot pair of panties under my clothing. I must have become too confident because one day it caught up to me. Terry was a guy I knew from work. We had known each other ... Read full Story
shemale lover 2012-09-14 2,076 Cumshot Blowjob jerking off crossdressing
100%
Such a whore
I finnaly made this happen a few days ago ! i have been crossdressing for as long as i can remember.I still remember when i snathed a pair of my cousins panties when i was young i dont know theres is just something about womens clothes that just intrigies me . Any way growing up i always masterbate... Read full Story
shemale lover 2013-05-31 5,264 Stockings hardcore Cumshot suck sucking jerking doggy style cd
100%
Dress like a bitch then fuck like one
Tyrone and Lamar were a couple guys I had met in a bar last weekend. Lamar called me and asked me if I would unlock a cell phone for him. I agreed and just as soon as my wife left I packed a small over night bag and drove to his house. Last night I spent the night with a couple friends. We drank... Read full Story
Rocky Wachenheim 2014-09-17 4,934 Crossdresser Cumshot suck Big Cock deep throat
66%
The Dark Backwards
Let me begin by saying that I am fascinated with shemales! I AM IN LOVE WITH SHEMALES! How did this love affair begin? For me it started back in 1984 when I saw a shemale magazine lying on my high school campus. Someone left it behind or it fell out of a bookbag. That image of a redheaded shemale le... Read full Story
Bryanferryfan 2015-11-16 3,384 orgasm sex transsexuals erotica
100%
THE DARK BACKWARDS
Let me begin by saying that I am fascinated with shemales! I AM IN LOVE WITH SHEMALES! How did this love affair begin? For me it started back in 1984 when I saw a shemale magazine lying on my high school campus. Someone left it behind or it fell out of a bookbag. That image of a redheaded shemale le... Read full Story
Bryanferryfan 2015-11-16 2,334 tranny orgasm hard dick transsexuals erotica
100%
Can't See The Forest For The Trees
Can’t See The Forest For The Trees Over time I have come to realize that women who are truly your good friend and have a healthy libido and are in an active intimate relationship can not sit still if you are celibate. This is a case in point. There were two extremely comely young ladies who we... Read full Story
DRILLMASTER 2023-10-28 5,105 sissy
94%
Miss Tiffany Fulfilling Her Dream
Finally, I had everything I needed to dress up for a little fantasy today. Ever since I was a little boy, I had always thought my neighbor Steven was extremely handsome and sexy. At 6 feet 3 inches, Steven is exactly what is described as tall, dark, hard tone and muscular. Tonight, I would finally h... Read full Story
shemale lover 2014-11-17 4,372 ass licking perky tits face fucking
50%
Me & Jo Shemale
Yesterday Jo Shemale and I went for on a pussy hunting fall walk. Well, I did, I'm pretty sure Jo Shemale wasn't hunting pussy. It was getting colder, so we had to put on our woolly panties and sweaters. Halfway down the block, we saw the Old Fuck's out in their yard. The Old Fuck's were raking b... Read full Story
shemale lover 2011-08-16 4,330 cock suck shemale
100%
Ashley Simone
Guys, I'm telling the truth here. This is just part of a story that I could tell regarding Ashley Simone. She is a transexual escort/pornostar that lives in Washington, DC. Her add is on the eros-dc.com site. Trust me if you like what I'm gonna relate, then you need to call her when you are ... Read full Story
shemale lover 2011-10-23 4,771 Big Tits transsexual
100%
A Very Pretty Boy
The warm buddle bath feels so good on my smooth skin. I love shaving my long slender legs in the tub. My feet are a strong point, many lovers have said so as they kiss and suck my painted toes. Actually, I would be a good looking very sexy woman if my 7″ cum filled cut cock didn’t detra... Read full Story
shemale lover 2011-11-10 4,085 sucking cum
100%
It Was So Exciting
It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or ... Read full Story
shemale lover 2012-01-21 2,650 anal sissyboy submissive
0%
Let's do it together
I sit here with my dick in hand! All three of my girl friends and my two boy friends are out of town attending to their WORK and leaving this important stuff to me. I shall carry on alone until they return. I am looking at some pictures of a group of people fucking another group of people. Some are... Read full Story
shemale lover 2012-01-24 3,385 Group Sex Outdoor dildo bondage
100%
My first anal
This was a couple years ago, but I still remember it very well. I was insanely horny one night so i signed up for a sex dating/chat site. I'm siting around, rejecting chat invites from guys, thinking I'd never want a cock. After a while, I decided to try chatting up a guy, see what kind of stuff ... Read full Story
shemale lover 2012-02-24 4,502 first time anal sex doggy style
100%
Alabama Nan: Behind A Closed Doors
"How's Chinese?" I asked Karen. "That's fine Nan. Is this a real fancy place or what?" responded Karen from the bathroom. "It's your regular Mom and Pop, type restaurant. I'm going to dress casual." "Sounds fine by me?" said Karen. My stomach growl... Read full Story
shemale lover 2012-04-27 2,082 transsexual orgasm oral sex
100%
Shemale Mistress
Tony turns 21 and decides to go party with his friends. Tony, with Bob and Chuck, (his college roommates) want to try out a bar on the other side of town - a new bar called "Desires" that they had heard a lot about, but never visited. The bar was known for wild and crazy parties. They also... Read full Story
shemale lover 2012-05-02 4,723 Cumshot domination cum swallowing facefucking huge dick
75%
On School Grounds
It’s amazing how good the cloth feels against your bare skin. I had never thought of myself as anything but a straight and regular Joe. I didn’t think that I’d get a stiffy wearing woman’s clothing like this. I looked at myself in the mirror, just to see if my padding was ... Read full Story
shemale lover 2012-09-05 2,374 Crossdresser Cumshot Masturbation
100%
Transsexual Mistress
I had heard some intersting comments about this S and M club and so I decided to go by and check it out. I walked in about 9pm and things were just starting to get warmed up. I sat down with a beer and looked up at the main stage where a gorgeous raven haired dominatrix with an enormous set of ti... Read full Story
shemale lover 2012-09-08 4,420 Cumshot Blowjob domination ass fuck
100%
Mistres
Tony turns 21 and decides to go party with his friends. Tony, with Bob and Chuck, (his college roommates) want to try out a bar on the other side of town - a new bar called "Desires" that they had heard a lot about, but never visited. The bar was known for wild and crazy parties. They also... Read full Story
shemale lover 2012-09-18 2,791 Cumshot sucking domination
100%
Friendly Neighborhood
"Oh my God Katie, your ass is so fucking hot" I hear as the cock slides in and out of me. "Yeah baby, suck my cock" comes from the guy standing in front of me with his dick in my mouth. I'm on my knees with a cock in my ass and one in my mouth. These cocks belong to my neig... Read full Story
shemale lover 2012-11-29 3,675 Crossdresser cum oral facial
83%
smoking
Greg decided to go straight. I had to find a new place to live. A nice man, Pete, who I knew from the YMCA, offered me a place in his basement. He was going to rent it out. It was nice, full kitchen, bedroom, laundry room, living room and another space for anything I would need. His rent was che... Read full Story
cd4fun715 2019-01-08 2,677 Amateur
85%
The Sex Club
When I got divorced back in 1987 I was a very horny man that had not had sex in many years. I had always liked to dress up in nylons etc and learned long ago that I was Bi and liked cocks and pussy. When I finally got my own place after the divorce I almost always would lay around the house dressed ... Read full Story
crossdresser55 2019-09-11 9,532 Stockings Crossdresser Lingerie Sex Toys
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,471 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
93%
MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
darrell 2023-08-13 5,836 anal Cumshot Shemale Fucks Guy Fetish blonde Big Cock domination Mature deep throat cum in mouth sandals
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 5,422 anal Cumshot Bareback cum in mouth
100%
Hits, Misses: G
Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibili... Read full Story
bybaking 2024-02-06 3,616 anal Amateur Cumshot Bareback Big Cock Ebony Guy Fucks Shemale Interracial black Tgirl
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 3,254 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
56%
First black T-girl
I've been wondering what to write about lately. I've received a request to write about me and my sister, but that is a road I might have trouble going down. Today I was thinking about my bi-sexual stripper girlfriend from the past, who loved bringing home other strippers (mostly lesbians) for some h... Read full Story
bigtranslover 2014-01-01 6,803 first time shemales interracial sex
92%
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 2014-03-29 18,501 anal first time shemales
90%
Italian hoe!
Verona is a nice city. Here, a motherland of Shakespeare’s “Romeo and Juliet”, there are lots of places of interest to see and enjoy. Verona has much more to offer. The city, also known as Urbs Nobilissima, is the second biggest city in Veneto (after Venice). It is one of the citie... Read full Story
shemale lover 2014-05-11 4,815 ass shemale boobs
100%
Jay in the Restroom
So I'm standing at the urinal doing my business when the first girl walks in. Now, just in case you're a girl and you don't know, men don't look around when someone else walks into the restroom. It's just a boy thing, we don't look at each other while we are urinating. It's like being in a elevator,... Read full Story
shemale lover 2011-08-09 4,972 Group Sex Masturbation threesome
100%
His Perfect Shemale Partner Part 1
I am in senior year of school and anyone who has been to school at 18 will know it is not a pleasant time to be working when your friends are all out drinking and enjoying themselves but I needed to go back to school to go the university I wanted to go to. I am a tall fairly muscular straight guy wh... Read full Story
shemale lover 2011-08-28 4,899 anal Cumshot sucking
50%
The Sexiest Shemales Part 1
When I wake up in the morning, I wake up next to the sexiest shemale in the world...right after me, of course. I woke up this morning next to Holly, my beautiful shemale girlfriend. She was still sleeping in our big bed. The sun was shining in on our bed with our white sheets and white comforter. ... Read full Story
shemale lover 2011-09-03 2,695 anal Cumshot sucking
100%
Connie at an Adult Bookstore
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by i... Read full Story
shemale lover 2011-09-30 4,049 Cumshot Blowjob crossdressing
100%
Goddess at the Bar
The beeping began, suddenly, and without remorse. Jan reached over, slapped the off button on her alarm, and lay for a moment debating the merits of rising out of bed. Deciding that waking up would be more productive, she slid out of bed, stood, and walked to the bathroom to take a leak. Emptied,... Read full Story
shemale lover 2011-10-14 4,611 Cumshot asshole dildo
100%
My First Time Out Part 6
Preface: It is not imperative, but helpful that you read Chapters 1-5 in order to grasp the personalities of characters in this story. WARNING: The following story contains some explicit foul language and IS NOT for reading pleasure for anyone under the age of 18; nor is it permissible to read if... Read full Story
shemale lover 2011-10-18 2,780 shemale dick skinny
50%
My Descent
This is the first time I've told my story publicly. I wrote this maybe 3 years ago, and have shared it with one person. I used to cross dress in my hotel room while away on business trips. I'm a fat bald 46 year-old who looks ridiculous dressed up in ladies underwear. When you're obsessed, tho... Read full Story
shemale lover 2011-11-05 3,026 anal first time cum oral
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 4,550 shemales Group Sex gangbang
100%
She's Not Hazel
My family had hired Maria awhile back a live-in housekeeper. She was from some small town in Brazil and was brought here through some charity from the church. She is only in her late 20's and is extremely attractive. she looks just like one of those girls you see party on E! Wild On, Her skin has a ... Read full Story
shemale lover 2011-11-29 3,155 oral cum swallowing
100%
First Time with a Male
It was Eight AM and Travis Gomez was getting things ready for a new client that was due anytime. Travis was cleaning the mirror behind one of the sinks when he turned and saw Mavis Nottinghill. "I know that your new client is due anytime but I was wondering if you could shave my pussy the wa... Read full Story
shemale lover 2011-12-01 2,140 pussy cum oral
33%
Growing up CD
Peter, Max and I played together like that for the rest of the weekend. We must have sucked each other's cocks at least 10 times over the three days. Peter and I were both physically drained. Max just seemed to be insatiable for our bodies. He didn't want us to go. He kept on saying how much he ... Read full Story
shemale lover 2011-12-04 4,012 sucking Fetish
62%
Naples
I had been at sea about a month when my ship pulled into Naples, Italy. The only action I had seen had been slipping away to my hiding place on the ship to jack my dick on a regular basis. I was ready to find some Italian pussy. I was slim about 6' with blonde hair and a fat 7" cock that ... Read full Story
shemale lover 2011-12-16 6,249 Teen (18+) shemale gay
50%
I am Baaack! Part 8
Robbie remained behind. She waited till the paper smoldered and then finally caught fire, then she went back into the den and put on her dress. She mussed her hair and smudged her makeup as if she had been sleeping. She looked back into the living room, and seeing that the fire was spreading from th... Read full Story
shemale lover 2011-12-16 1,998 crossdressing erotic encounters fantastic
50%
I am Baaack! Part 10
She turned back to Dainie, and spoke to her like a proud parent. "Dainie, honey, I am so proud of you! I'm so sorry I had to speak harshly to you earlier, but you do know that you deserved that, don't you?" Dainie nodded yes. "And don't you feel so much better, now?" Dainie shyly... Read full Story
shemale lover 2011-12-17 1,749 crossdressing erotic encounters fantastic