Sort by
Relevancy

Free Stories

100%
Late for Work
She was dressed only in her plain white cotton bra and a skirt when he called her for breakfast. She was frustrated she could not find her favorite blouse and rubbed at the dark circles under her eyes. Picking through the massive pile of clothing she found a gray tank top with a stain on one sid... Read full Story
shemale lover 2013-02-06 6,183 sucking jerking domination Guy Fucks Shemale big boobs
97%
How I Met Alyssa
I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up. I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year o... Read full Story
shemale lover 2013-02-12 14,450 hardcore sucking Big Cock ass fucking big boobs
93%
Surprise
Brad was at the park one Saturday afternoon playing softball with his buddies when he spotted Morgan, a gorgeous tall thin blonde sitting on a nearby bench. Brad accidentally lost the ball near where she was sitting and had to go get it. The softball game had wrapped up and everyone had packed up th... Read full Story
shemale lover 2013-03-05 17,144 hardcore sucking Shemale Fucks Guy Blowjob ass fucking
100%
CD And Trucker
At least four things went through my mind the moment I heard Hank ask me to go along with him. - One my wife was gone for at least 2 weeks so that was no problem. - Two, with wireless connection and my laptop I could take my job on the road. - Three, I had hardly any clothes in my bag that I was ... Read full Story
shemale lover 2013-04-30 9,930 Cumshot fingering domination spanking cd
94%
A NIGHT WITH A TRANSEXUAL
Since my passionate weekend with a shemale and just getting my ass fucked for three days almost by a beautiful black transexual with a 13" she meat,my fantasy for tranny cock was finally fulfilled,a couple of weeks after that weekend i went to a local gay bar called Crusing 7,it`s was sunday ni... Read full Story
shemale lover 2013-06-22 6,112 suck Creampie Shemale Fucks Guy ass fucking 69
100%
VICKI LARA RIVERA,MY SEXY TRANSVESTITE GF
I met Vicki at a hook up site,she had an ad that caught my attention it went something like this "hispanic transexual looking for a serious relationship with an honest man",i read her ad and liked the fact that she was looking for a relationship and not just a one night stand,I`m very much... Read full Story
shemale lover 2013-07-10 4,659 sucking Shemale Fucks Guy ass fucking Guy Fucks Shemale stroking
96%
A Trip to the Beach
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2013-07-21 10,697 hardcore Cumshot Shemale and Girl oral sex kissing
95%
My first shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe t... Read full Story
shemale lover 2013-07-21 12,032 anal sex ass licking oral sex kissing transexual
92%
The first sex! A dream for a little sissy slut!
We decided to meet at your place, I enter quickly and immediately go into the bathroom to get ready for our spicy evening. I'm already shaved and wearing stockings, leopard print panties matching bra. In the rush I'm doing makeup, I get dressed in little black dress, barely covering my bum! I put a ... Read full Story
shemale lover 2013-08-09 5,874 Stockings hardcore Cumshot Lingerie domination spanking
93%
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 2015-02-27 5,886 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale
85%
THE DARK BACKWARDS CONTINUES 2
I jerked off several times while watching the SULKA video. At this point I wanted more. I returned the videocassette to the video store and made my way towards the darkness that was the ADULT section. I opened the door and there were several people in the room. My excitement turned to fear. Fear of ... Read full Story
Bryanferryfan 2015-11-16 3,333 tranny shemale jerking hard dick transsexuals
80%
JUERA MARICON
My name is Keven Jeanne and, Yes, I am a Sissy! When I was 13 I put on my mom's panties and some of her lipstick when she was at work. I had longish blonde hair and I ruffled it up - kind of teased it up - and when I looked in her dresser mirror, I almost ejaculated. Because what I saw looking ... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,594 blonde shemale submissive cocksucking
90%
Lost Island
Bright light hit my eyes when I opened them after a long time. My mouth was full of sand, my toung dry and the taste of salt overwhelmed me. I was stranded. My boat sank in a terrible storm and my body was washed on this lonely beach of a tropical island. The sea was calm and there were almost no w... Read full Story
xgandalf 2016-05-04 6,581 sucking gangbang domination ass fuking Shemale on Guy
63%
A Slice of Life - Ch. 1
Written by Nobody Home. All comments and feedback welcome! 1. It is dark out, night descending upon a wintery, snowcapped city backdrop. Cold against the windowpane, I feel my head shoved into it and my hand makes a streak against the glass. My would-be attacker tears my panties off of my slen... Read full Story
Nobody Home 2016-12-20 5,443 ass fucking cumming Guy Fucks Shemale cd sissy
78%
My Futanari Dreamgirl
My Futanari Dreamgirl I opened the door and there it was, just swinging between her legs. Big and veiny with a bright pink head. My roommate Jesse didn't notice me walk into the bathroom. She had just stepped out of the shower and was toweling off her hair. Her eyes were covered by the towel... Read full Story
Jade Dixxon 2017-10-23 20,564 tranny Cumshot Blowjob Guy Fucks Shemale Futanari
100%
one of those stories i wish i was in.
Tim stepped into his new college dorm room and breathed in the possibilities. The sun illuminated the simple tile floor and the simple room furnishings. Freshly cleaned desks and wardrobes neatly lined the walls. The beds had thin blue mats and pencil graffiti etched into the legs. He noticed that t... Read full Story
TylerTheLovely 2018-03-02 6,673 Shemale Fucks Guy
100%
My Afternoon With Venus - Part II
My mind was still spinning from the out of this world cock sucking I'd just experienced at the expert lips of my exotic little doll as she led me by the hand into her bedroom. Her pink summer dress was draped down onto her waist so now it was only just covering her cute little derriere. As I wa... Read full Story
funpics 2018-03-23 13,802 Amateur Shemale Fucks Guy Asian Ladyboy Guy Fucks Shemale Homemade
90%
Long weekend at work
So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dar... Read full Story
Zöe from Kingston 2018-08-09 6,172 Cumshot Bareback Shemale Fucks Guy Blowjob cum in mouth
100%
A Big Celebration that goes sides for me
I'm reading my book when she enters. I hear a clatter of keys and I look up, to see framed in our little entry way the tall figure of my roommate. She's standing there as in triumph, legs planted apart, her face all smiles. I smile too. Geena never looks this happy, I've never seen this side of her.... Read full Story
ASSEaster5678 2018-09-14 3,912 Ladyboy party Surprise
95%
Halloween Night Again
Last October my girlfriend Kelly and I were drinking wine and playing cribbage on a cold, rainy night. After dating her for six months we usually stayed in on weekends. I consider myself very lucky to be dating her. She is an incredibly beautiful brunette and has a perfect 36C-24-26 figure on her 5'... Read full Story
ASSEaster5678 2018-10-29 13,396 Shemale Fucks Guy Guy Fucks Shemale Halloween
92%
My wife Gwen
My wife, what can I say she is tall and leggy with thick, natural wavy orange-red hair with beautiful porceline skin and just enough freckles to tell you she is a true ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen. From the time we... Read full Story
Zöe from Kingston 2019-01-08 7,947 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
91%
The New Housemate's Secret
https://chyoa.com/chapter/Introduction.150836 The New Housemate's Secret How will you discover the hot new tenant's secret? Chapter 1 by Bauer1 The doorbell rings, a soft knocking accompanies the bell to break the silence of the house. You look up from your laptop nestled snuggly in your la... Read full Story
Acche 2019-04-04 22,315 Big Tits Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock Guy Fucks Shemale handjob titfuck titjob cum in mouth
100%
Incubator
For lack of a better term, I will call him my Lover. I call him Grae, which sounds like "gray" if you are doing a rather poor impersonation of a Scotsman. Not that I have anything against the Scots; that's just as close as I have been able to come to pronouncing his real name. You would think that s... Read full Story
ASSEaster5678 2019-04-23 4,854 Big Tits Bareback Shemale Fucks Guy Big Cock Guy Fucks Shemale monster
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 9,146 Big Tits Cumshot Masturbation threesome Frottage
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,854 Big Tits Big Cock shemale + shemale
90%
Nicole
This story is about my first time with a transgender. I had no previous experience with a transgender until 35. This happened on a Saturday morning when I was walking in the streets of Tokyo and I saw this foreigner woman and she seemed to be lost. As an English speaker and not knowing that she was ... Read full Story
cttyy 2019-11-16 17,648 Shemale Fucks Guy Big Cock domination cum in mouth
90%
My Night with Luisa Tavares revisited
I've made some adjustments to this story and will be writing a sequel. Hotspur I flew to Goiânia just to be with Luisa Tavares. She greeted me at the door to her apartment in a bathrobe. She had just taken a shower and invited me to do the same. When I returned from the shower, I found her sitti... Read full Story
hotspur 2020-01-10 11,606 Shemale Fucks Guy Blowjob Big Cock domination Ass to Mouth
87%
Melissa
I'm a Japanese in my early forties living in Japan and I met Melissa online about a year and a half ago when looking for someone to chat. She is a black, 6 feet 2 inches tall, around 160 pounds and therefore a slim and beautiful transgender girl in her mid twenties. From Brazil, she is very friendl... Read full Story
cttyy 2020-02-24 15,759 Shemale Fucks Guy threesome Big Cock domination cum in mouth double anal
100%
My First Experience
Preface: A few years ago I was surfing craigslist (back when that WAS a thing) and found a couple looking for a man. I responded to that post and went back and forth until we set up a time to play. I arrived on the night and had a few drinks, We chatted and I noticed that the husband kept touchi... Read full Story
rileystar 2020-04-01 19,471 Crossdresser Amateur Group Sex threesome Lingerie domination
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 2,264 anal Cumshot Shemale Fucks Guy Fetish Blowjob cum Lingerie slut sissy femboy handsfree Khloe Kay
100%
The Day I Went SheCock Crazy
I summed up courage to meet up with my old shemale flame Fransicca (she is a Malaysian but living in indonesia) ... messaged her, she sounded excited and asked if i minded her friend joining us. 'Why not' i said. It was settled. we booked a villa for the next day. I checked in early. cleaned up ... Read full Story
Sara Banks 2021-04-26 6,923 Group Sex Cumshot Outdoor Bareback Shemale Fucks Guy Fetish Blowjob blonde Big Cock Asian Ladyboy gangbang
100%
Threesome goes clubbing
Ft. Lauderdale is probably the most LGBT friendly city on the east coast. So many nice restaurants and clubs that welcome all and have many LGBT employees as well. Lydia and I have been married several months, we had met Joanne an absolute amazing transgender girl during a weekend trip to the Baha... Read full Story
Jon Paul 2021-07-08 5,496 Big Tits Cumshot Bareback Creampie threesome Guy Fucks Shemale cum in mouth
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 5,499 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale 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 4,610 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
100%
Surprise Ending (The End)
Karla struggled a bit to get the huge, bulbous head of her cock inside of me. It was like my ass had licked a battery. A charge went through my body that while painful, was exhilarating and exciting. "Ahhh," from my lips was all the encouragement I could offer and Karla took it. She steadily push... Read full Story
Chantel13 2022-08-23 5,799 Amateur Outdoor Shemale Fucks Guy Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth
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 6,722 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
50%
My erotic dream
Over the past few years I have been thinking about one very important thing.To jerk off all the time and to think about beautiful, sexy trannies who want you to fuck them for the rest of your life. I give in to temptation and when I see cum on my face, that's when a strong orgasm calls to action. In... Read full Story
Kalio 2024-03-06 4,664 Cumshot Masturbation Shemale Fucks Guy Blowjob big ass Compilation
80%
Fucked by Priscilla Gaucha
This black woman always drove me crazy, I always liked her photos and videos on the internet. Unfortunately, when I had the courage to face it, she moved out of state and ended up being left in the lurch. However, one night driving by, I came across her. She was beautiful, strong thighs, well made-... Read full Story
mauricioportoalegre 2024-05-09 3,715 anal Amateur Shemale Fucks Guy Big Cock Ebony
50%
KING OF TRANNY CHASERS ENTRY 1
IT WAS AROUND 1AM AND MY GIRL FRIEND GINA AND I ARE GOING AT IT.HER NAKED BODY WAS HANGING OFF THE BED IN DOGGY.HER BIG CARAMEL ASS CHEEKS JIGGLED AS A POUNDED FROM BEHIND. SHE WAS SCREAMING "YES BABY" AND MOANING NON STOP..AS BEAUTIFUL AS SHE LOOKED AND HOW AMAZING HER BACK SHOTS WERE LOOKING..W... Read full Story
Ghostface drillah 2024-07-02 2,905 Amateur Big Tits Masturbation Big Cock Ebony Guy Fucks Shemale big ass Homemade Ass to Mouth cum in mouth
100%
She Lied ......... Part 2
Looking back on that dat & being honest wit myself, I probably made sure I didn't swallow every drop. I think I wanted to finally lose my virginity. I wanted to be the bitch. I wanted to feel like the woman. I wanted to REALLY feel her she-cock expand deep inside me and feel the warmth of her nectar... Read full Story
Curious_billy 2024-07-06 3,949 Amateur Bareback Creampie Shemale Fucks Guy Big Cock cum in mouth seduction Sweet talk Virgin asspussy
100%
I had park sex with three HUNG black guys after dark !
So last night, I had sex with three black guys at a park last night as of writing today. This happened at midnight. But, let’s reverse and start from the beginning…. I left my house because I was feeling a little frisky and if anyone knows what sniffles app is , if you know , ..you know! So a hot sp... Read full Story
Ezra_Kyle25 2024-08-18 3,054 anal Crossdresser Cumshot Bareback Blowjob Big Cock Ebony domination Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
98%
Shemale Delight
I have always considered myself a, women only, kind of guy. After an experience I had 10 years ago, I have added shemales to my list. Anyway, I love to take road trips and visit different cities, usually out of state. I go on-line to do some research about different cities to see what kind of si... Read full Story
bigtranslover 2013-12-27 11,261 licking sucking pussy
85%
Sex with shemale and a girl
As a female, I'd never considered having sex with a shemale in my life. I mean, why would I want to be with a chick with a dick when I could be with a guy? Then, on a trip to Brazil, everything changed. I was in a club with my friends when that night's entertainment took the stage. She was one of th... Read full Story
shemale lover 2014-04-11 6,204 pussy rubbing chick with dick
75%
Fun time with russian shemales in Moscow
The first day, I was with my Russian friend, who introduced to me the Russian shemale escort. Since I know he is a big fan of shemales, so I wasn't shy of asking him about shemale escorts in Russia. He called in a shemale escort for me rightaway. I was staying in a hotel in downtown Moscow. Since my... Read full Story
shemale lover 2015-03-09 15,299 Group Sex threesome shemale
80%
Car sex with a shemale at the local drive in
I know for sure many guys are fascinated about fucking a shemale in a car. Well, this is what the story is about. The guy rammed shemale ass at the drive in. Happy reading! I pulled in with my radio up and saw the most beautiful girl walking right in front of my car. Her legs were long and brown ... Read full Story
shemale lover 2015-08-01 9,100 cock shemale fucking
83%
Sandy Just Loves To Make Shemale Tube Movies!
Sandy Just Loves To Make Shemale Tube Movies! She was working as an actress. Well, at least that's what she had told me, and I couldn't even imagine she was making shemale tube movies . I had no reason to doubt her. She was a tall blonde with huge firm tits and the most tempting ass I have ever s... Read full Story
shemale lover 2015-12-07 4,791 suck asshole transsexual
73%
My Shemale Webcam Tubes Next Door Neighbor Rendezvous
Whenever I would feel down or lonely, I would go online, look for shemale webcam tubes and enjoy myself. I would always find someone interesting there that would satisfy my senses. That night something amazing happened. I came back home, all fired up, wanting to please myself, I went online and t... Read full Story
shemale lover 2015-12-27 4,705 asshole shemale tits
87%
Amateur Shemale Videos Just Next Door
I rented out a place in this neighborhood not because of the fabulous location but because it was really cheap. It wasn’t what you call a family neighborhood, but nobody was picking on me, at least. My flat didn’t have much of a view. The living room window was facing the building nex... Read full Story
shemale lover 2016-04-12 8,496 Cumshot suck Creampie
58%
Porno Mobile Shemale Video
I have been always turned on by shemales, but somehow I couldn't find any that would like to be with me. That's why I was always watching shemale movies and I even had several porno mobile shemale videos on my android. I was always fascinated by the fact that I could sleep with shemale and touch her... Read full Story
shemale lover 2016-04-28 11,382 asshole Big Cock oral sex
40%
See Me At Shemale Cam Tube
I was dressing when I heard a new e-mail arriving. "You're hot as hell on Shemale Cam Tube", he wrote, "Wanna meet me 4 lunch? Promise to be a gentleman!" It was cute, especially coming from such a skinny guy. I'm a big girl - over six feet, with strong legs and huge breasts whic... Read full Story
shemale lover 2011-08-09 6,720 asshole Blowjob shemale
100%
Buffy the Shemale Vampire Slayer Part 11
Darkness had fallen upon the demon world. In the intermittent flashes of lightning that resulted from Willow's weather spell, the landscape was illuminated, and the horrible phallus-plants were revealed, writhing and thrashing. The cock-stalks within Buffy's mouth, cunt, and ass, and the hollow tubu... Read full Story
shemale lover 2011-08-21 4,426 asshole shemale Big Cock
80%
Buffy the Shemale Vampire Slayer Part 14
"Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't-" "Th... Read full Story
shemale lover 2011-08-23 5,326 anal sex asshole Big Cock
85%
Father In Law Shemale Adventure
My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... Read full Story
shemale lover 2011-08-26 6,048 Cumshot asshole fingering
100%
His Perfect Shemale Partner Part 2
Quite a few things have changed since the last chapter. OK maybe not that many, I am still lusting after Sally's body needing to have my dick in her and feel her in me, but we are a lot closer now as we are living together. Sally has gone to her 1st choice University and I decided I would rather get... Read full Story
shemale lover 2011-08-28 5,081 Blowjob shemale cum
83%
Attitude Adjustment
Angel sat on a chair in a crowd of women. She had come to this club to take in a couple of shows and she was really enjoying this one! This show was a group of hot looking guys that stripped for a living, which is nothing unusual in Miami, but these guys showed the "Full Monty", or in othe... Read full Story
shemale lover 2011-10-24 5,907 asshole Creampie Big Cock
100%
Kayla and Tracy: The Layover
Kayla and Tracy strode across the marble-floored lobby, their heels clicking across, and suitcase wheels rolling across, in rhythm as they walked up to the desk. They seemed incredibly out of place in the relatively quiet hotel room. Kayla, of course, always stood out, especially when platform heels... Read full Story
shemale lover 2011-10-31 4,418 big dick tranny asshole