Sort by
Relevancy

Free Stories

56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 95,934 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
94%
Tortured by the T-Girl Tutor
Duncan didn't quite know how to handle it. He'd planned on a quiet Winter Break. Sleeping til noon, watching too much television and eating tons of junk food. That kind of stuff. He had a whole two weeks off from community college. At school, he was an outcast. They say life gets better after hi... Read full Story
shemale lover 2012-12-18 34,039 Big Tits shemale Big Cock Lingerie domination
72%
Daughter Finds Out Mum Is A Shemale
I had a free period at the end of my school day so I decided to come home a bit early. I got home and headed upstairs to my room when I heard a faint moaning coming from the study. I leant in towards the door and I couldn't hear anything. I opened the door to make sure nobody was in there and what I... Read full Story
shemale lover 2012-07-27 59,359 shemale oral sex self sucking
86%
The Girl Next Door Ch. 01 by derezzed ©
Michael was your average 21-year-old college student. He was on his way home from college for summer break after finishing his finals and looking forward to a few months of relaxation. Driving home Michael reflected on his past three years of college. It had been a great junior year. He met a lot of... Read full Story
StevelovesTgirls 2019-05-27 18,090 Amateur threesome Big Cock shemale + shemale
94%
The Girl Next Door Ch. 01
derezzed Michael was your average 21-year-old college student. He was on his way home from college for summer break after finishing his finals and looking forward to a few months of relaxation. Driving home Michael reflected on his past three years of college. It had been a great junior year. H... Read full Story
Gwapo67 2022-05-13 6,777 Bareback Creampie Big Cock shemale + shemale
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,215 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
How I sucked my first shemale cock
It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... Read full Story
cock&heels69 2023-05-25 8,721 Stockings cock Masturbation sucking Blowjob shemale orgasm oral sex porn high heels cum shot first experience
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,399 Big Tits sucking ass licking fucking
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,126 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,477 anal sex sucking shemale
90%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 13,359 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 5,083 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
80%
Beautiful ladyboy Natalie
Feasting comes after fasting. What's with you guys, it's been over a month that i haven't seen any new shemale stories from you, and now i'm getting them every day. Which is good of course. ;) Here's a shemale story from Tommy about his long-standing shemale fantasy finally fulfilled. I'd had she... Read full Story
shemale lover 2015-05-03 5,381 sucking shemale cum
78%
A Little Girl Forever
Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... Read full Story
Mabel Cecilia 2019-05-06 8,042 Small Tits Crossdresser Amateur Cumshot Latina Masturbation Creampie Blowjob blonde Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys Mature self sucking Solo Shemale cum in mouth double anal shemale + shemale
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,360 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,352 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 7,047 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
70%
Teen pussy rendevous!
Yes, she said she would meet me at the same bathroom stall and would not you know it, she did exactly that! I was already in the ladies room, wahing my hands, and in she walks, absolutely stunning, heels on , short summer dress, beautiful face and hair and what a body, my cock got so hard right then... Read full Story
shemale lover 2014-02-23 5,239 sucking
92%
A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
shemale lover 2014-05-21 18,568 shemale fingering cumming
81%
A LadyBoy For My Wife
I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... Read full Story
shemale lover 2012-06-23 10,845 Group Sex Masturbation shemale Ebony facial
100%
Cheating Sissy Wife chapter2
My sweetheart Keith is back from his road trip and we were about to make up for lost time. He didn’t even want me to fix dinner. Instead he said that we would order pizza later. Meanwhile we started making out right there on the couch. We were both horny and anxious to get next to each other. I felt... Read full Story
Regina10 2020-10-26 4,813 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
50%
Twisted
"Baby, are you sure this is the place?" Eve squealed a bit too loudly, her voice both high-pitched and thick from the third Cosmopolitan. "This looks so, I don't know; fancy-shmancy for a full on mix-it-up ladyboy bar. I know, I know, this is South Beach and everything here is la-de-d... Read full Story
shemale lover 2011-10-31 4,889 shemales Big Tits fingering oral sex
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,938 Stockings Big Tits fucking foot fetish
100%
Case of the Jealous Transsexual Chapter 2
Dee-Dee was becoming a little possessive after the 2 times that we had seen each other. She began calling me everyday, emailing me, wanting to know when will we see each other again and so on. To tell you the truth I had moved on. I had done everything with Dee-Dee that I felt could be done on a phy... Read full Story
shemale lover 2012-03-19 3,339 Group Sex Big Tits Cumshot
88%
Mom's girlfriend has a fat cock
When I was a teenager, my mother got remarried...to a woman. At first it was odd, because their roles in the relationship were so clear. My mother was the "bottom", and Jamie was the "top". They're great to each other, and I have grown to love Jamie unconditionally. I'm eigh... Read full Story
TripFontaine 2012-05-14 15,670 anal cock shemale cum tits lesbian
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 118,806 hardcore Cumshot sucking bdsm domination
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,819 Masturbation cum orgasm cumshots prostate
100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 7,963 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
75%
Amy Finally Lives Out Her Fantasies Part 2
"Wow! What got into you?" "I don't know, I just decided to finally loosen up and go with my desires," she explained. "Did you enjoy it?" "Are you nuts? I LOVED every second of it!" I exclaimed. Figuring the alcohol played a very large role in her sudd... Read full Story
shemale lover 2011-09-15 3,690 Big Tits ass fucking fishnet
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,185 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Buffy the Shemale Vampire Slayer Part 12
The demons found exits in the walls or floor, vanishing between chinks of stone or through hidden grates or into holes they'd dug for themselves over the long centuries of their residence-or imprisonment-in Baphomet's palace. Only one remained. "My former consort, Baubo," Baphomet intro... Read full Story
shemale lover 2011-08-21 4,563 hardcore asshole Big Cock
50%
Healthy Behavior
"Uhh…is Mr. Stanford around?" "One moment dear…ooh, damn heels. Makes it impossible to walk through doorways. Here I am ma'am. So, did the maid get you here alright? Hello? Earth to…" "I can't believe this…" "Oh, the heels? Yeah... Read full Story
shemale lover 2011-10-19 3,958 Big Tits transsexual oral
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 9,491 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,480 Big Tits Cumshot Masturbation Uniform Frottage
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 4,995 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
100%
TG Neighbor
With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... Read full Story
Jon Paul 2022-04-22 6,575 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
Jennifer
WhiskeyIsGood I woke with a start, startled by a loud banging sound from downstairs. The floor shook from the vibrations, causing me to sit upright in my bed and glance towards my bedroom door. What in the hell, was going on down there? My question was quickly answered, by another loud bang, foll... Read full Story
Gwapo67 2022-09-13 6,028 Big Tits Bareback Shemale Fucks Guy Blowjob blonde Big Cock
66%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 4,660 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
0%
The orgy with a shemale
I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name w... Read full Story
shemale lover 2011-08-29 5,182 Big Tits asshole Big Cock
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,941 first time sucking fuck domination
100%
Fender Bender
It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... Read full Story
shemale lover 2012-07-26 8,389 Teen (18+) Fetish crossdressing
92%
Lucy's Change chapter 2
Chapter 2 Sunday was even darker and rainier than Saturday. We woke up still holding each other from the night before. We were spooning. Lucy’s warmth felt so nice against my back. Her legs only reached halfway down my calves, and I could feel her rubbing my legs with her toes. I could tell that sh... Read full Story
Alex1090 2015-03-31 6,375 anal big dick tranny shemale ass fucking
87%
Why you should never cam
* Sorry for the poor writing but since it is the summer and I am taking sometime off to reflect before starting school next year I thought I would write up about what had happened to me the summer before. It is currently a work in progress and if spot any spelling mistakes or errors feel free to cor... Read full Story
jennychen 2014-09-02 5,235 cock shemale Big Cock Asian
92%
The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
StevelovesTgirls 2019-06-11 12,554 Amateur Big Tits Blowjob Big Cock Guy Fucks Shemale
88%
Who's She?
School had been a bore for Tony. He was a bright lad and didn't have to work too hard to get through classes unnoticed by the teachers and class mates. He had plenty of friends but no one close. He didn't excel in sports or academically. He had picked up a few good exam results but had decided that ... Read full Story
Vinny_A 2019-07-08 11,689 Teen (18+) Crossdresser Amateur Big Tits Bareback Blowjob Lingerie
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 10,614 Big Tits Big Cock shemale + shemale
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,218 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,306 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
A Shemale Vacation Part 2
We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... Read full Story
shemale lover 2011-09-05 7,125 anal cumming cum swallowing
100%
A Dickgirl Part 2
Ginny was mortified. For the first time in her life she hated her body. Why the fuck did she have so little self-control? Why couldn't she hold her body back? Why couldn't she be like normal girls? She cried all the way home, her tears drenching her shirt. She stopped by the time she got home, bu... Read full Story
shemale lover 2012-02-27 6,678 Cumshot sucking Big Cock Shemale and Girl
100%
Blossoming Shemale
My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to ... Read full Story
shemale lover 2012-08-01 5,019 Cumshot shemale Big Cock oral sex
94%
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 that started my intere... Read full Story
SachinJoy 2018-10-04 32,634 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
42%
sexy jane story
I love the idea being a crossdresser wearing women outfit bars in panties n sexy outfit not just for the sex I love sex being on my knees sucking cocks in getting fuck by a big cock see win I was very young I had sex with 3 guys one day they ask me will I suck there cocks in I sand yes we want insid... Read full Story
45sexyjane 2019-05-27 4,220 Small Tits Crossdresser Amateur Big Tits Masturbation Blowjob blonde Big Cock gangbang Lingerie Sex Toys shemale + shemale sexy crossdresser
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 5,176 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Late Night Snack (Touch me in the morning)
I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... Read full Story
Regina10 2024-03-28 3,952 anal Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ebony Ladyboy Lingerie
100%
Shemale On Webcam Made Me Cum
It wasn't enough for me - regular porn, regular girls... I felt like I was losing it, not having the only thing I really desired: a shemale. But I was new in that world, not knowing where to go, where to look, so I decided it was better to see shemale on webcam first. I searched the internet and ... Read full Story
shemale lover 2015-12-31 3,965 Big Tits Cumshot shemale