Sort by
Relevancy

Free Stories

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 13,336 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 5,065 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
96%
Ladyboy surprise in Bankgkok
A few years ago I went to Thailand for the first time, my first stop was the bustling city of Bangkok. I had heard stories about the nightlife, the girls and the tourists. The country had never appealed to me that much but through a twist of fate I ended up visiting the city of sin for a couple of d... Read full Story
Gracemel121 2021-03-25 11,850 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy cum in mouth
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-14 2,316 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
81%
First time with ladyboy / bottom
Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... Read full Story
FoxyLover'ts 2020-10-06 16,122 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,341 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 2,915 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
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 2012-12-21 118,743 hardcore Cumshot sucking bdsm domination
100%
Being Shemale Part II
After sometime the driver left. Night Two I was again ready by 10 Pm as usual wearing make up and sexy night outfit. My push up bra helped my breast look very attractive looked perfect with my slim body I was standing as usual in the balcony around 11 PM and the driver stopped by again.... Read full Story
babydriver 2024-06-04 2,327 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy Lingerie domination small cock big ass Frottage sissy femboy
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 4,166 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
80%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 6,036 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 4,756 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
66%
The House of Lesslie
I. The mansion hadn't changed, not all that much, from how I remembered it. If at all, it had aged gracefully, as only English mansions can ¬ a massive Edwardian building that had served Lords and Ladies, had housed masters and servants for centuries. Around it, at a respectful distance, w... Read full Story
shemale lover 2011-10-14 5,564 pissing domination Latex
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,342 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
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 9,802 anal Ladyboy oral
54%
Shemale transformed in to a living sex doll and kept captive
I had connected with Master X on a BDSM Fetish contact site. He was the owner of a fetish store and he said that he had been on the BDSM for several years. He had carefully studied my own profile and had seen that I had an immense interest in being used like a slut, being covered head to toe in ... Read full Story
__tiffanylondontv__ 2014-09-30 8,212 ass Fetish bdsm domination bondage
50%
I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
Oldslut Sissy 2024-04-15 8,944 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
100%
Bangkok Night with Thai Ladyboy Dancer
I was visiting Thailand back in the 90s and was blown away by the “Potpourri” of sites, sounds, and smells (not all of them good) of this city. Beautiful women were at every corner and very friendly to foreigners. I went out with a group of guys on the town after dark to check out the go-go bar scen... Read full Story
AllenB 2022-04-20 5,831 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
100%
Chinese Apple Turnover
I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax f... Read full Story
ASSEaster5678 2019-01-09 6,567 anal sex Shemale Fucks Guy Asian Guy Fucks Shemale
82%
My shemale weekend
I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting... Read full Story
shemale lover 2015-09-05 9,467 shemales Group Sex interracial sex
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 10,797 Group Sex Masturbation shemale Ebony facial
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,154 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
77%
My Dream Cums True
Me and my girlfriend would always talk for hours about our secrets and feelings and as the night would progress we would get into more sexual subjects but this night would change our lives forever..... ''so what's a sexy secret you have that no one else knows about?'' I asked my girlfriend. ''... Read full Story
Fistagon8 2012-03-28 6,878 first time shemale Latex pornstar
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,863 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
100%
Becoming Her Whore
"I know," my wife Casey said softly as her hands caressed my naked body beneath the covers of our king sized bed. "You know what?" I asked. I didn't know what game we were playing but I was ready to fuck. "I know what you look at on the computer and what you fantasize ... Read full Story
shemale lover 2011-10-23 7,669 suck shemale Latex strapon
80%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 11,468 Bareback cum ass fucking slave
94%
In Love with a Shemale
I was out one night in a busy club and I couldn't help to notice this one girl staring at me constantly. She was incredible wearing a tight little skirt showing off her long legs with an amazing smile and a very cute face. I planned my move and went to the bar when she did and she started talki... Read full Story
curiousshemalelover 2014-11-29 10,295 tranny suck Shemale Fucks Guy ass fucking domination oral sex
60%
Shemale Chrissy Fucked by a Demon
I wanted to write this the night it happened, Halloween, but I was still so traumatized. I was at my fictional fantasy Sugar Daddy's house alone and already spooked out by the noises of this old hundred-year-old wooden house in this loud thunder storm on what some call "Devil's Night." I had to turn... Read full Story
Chrissy Tunnell 2022-12-01 4,082 Small Tits Crossdresser Amateur Bareback Fetish Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
100%
My First Ladyboy Adventure
I had been watching ts porn and thinking about visiting an escort for a while, when I found myself working in London and actually got the oportunity. I had been checking out the London Eros guide on the internet and had called several tgirls when I came across Seri Atika's profile. I called he... Read full Story
monkeyphoto 2014-10-07 10,775 hardcore Asian Ladyboy ass fucking Guy Fucks Shemale condom sex
69%
Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
Stud4Shemale 2017-05-22 7,421 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
95%
Late night park visit
It was 11pm on a Friday night, I was driving my car back from a failed meetup with a guy I met online a couple of days prior. I thought it was going to be an amazing night, so I spent close to two hours getting my makeup and hair sorted to look pretty for him when we met. I was wearing a short black... Read full Story
Natalie Bishop 2018-10-08 7,179 Amateur Cumshot Bareback Creampie Big Cock Ladyboy domination Guy Fucks Shemale public Park
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,859 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 2,771 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
K*dnapped & R*ped
"You're nothing but a tease, a flirt, you just like to play around and lead guys on," someone messaged me on the swinger site I'm on called AdultFriendFinder. "No," I replied, "I have actually hooked up with guys I met here, I am just very busy." And that is the truth. I work a full-time job and ... Read full Story
Chrissy Tunnell 2022-02-02 3,491 Crossdresser Amateur Outdoor Bareback Fetish Ladyboy domination Guy Fucks Shemale Homemade
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,627 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
95%
My TS Journey
I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my a... Read full Story
iconicirish 2022-10-26 8,220 Amateur Shemale Fucks Guy Big Cock domination cum in mouth escort ts
80%
fuck by my best friend's family
= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... Read full Story
Onikky 2019-06-25 9,380 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
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 3,730 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
50%
The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
shemale lover 2011-10-18 4,653 Group Sex Masturbation shemale oral
90%
A Sissy (S)exercise Fantasy
I stopped going to the gym about six months ago, when money got tight and I had to find ways to reduce my expenses. I usually don't get to the gym much in the spring or summer months anyway, so it was an easy expense to cut. I hate going into the office all sweaty, so I avoid working out in the morn... Read full Story
shemale lover 2012-06-14 9,309 Cumshot Fetish domination oral sex sissy
100%
Cow Girl`s got something hard in her jeans
Last Friday night me and the guys from work stopped to have a couple of beers. which of course turned out to be a whole lot more. boy was i going to be in trouble when i got home. but when i got home it was all quite, too quite. then i saw the note. "You son of a bitch you knew we had that dinn... Read full Story
shemale lover 2012-07-21 3,601 shemale oral sex facefucking
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 5,590 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
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 13,442 Amateur Shemale Fucks Guy Asian Ladyboy Guy Fucks Shemale Homemade
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,089 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,335 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
50%
My first time as a female
I was playing with my tiny dick one morning. Thinking what it would be like to have a pussy and some tits. Wondering what dick would taste like. These thoughts made me feel horny. I got a boner. K sneaked into my parents bedroom. Looking for Mothers sexy underwater. I found her panties and bras. I a... Read full Story
2BWoman 2022-09-07 4,853 Crossdresser Big Cock Ladyboy domination
100%
Shemale Maid
Colleen rushed through the mansion's open gate and headed towards the main door. She opened her mini leather bag and searched frantically for her keys, although she knew she was hopelessly late. Was it her third or fourth unsuccessful attempt in a row to get there on time? Or had there been more? Oh... Read full Story
shemale lover 2011-09-13 5,135 licking sucking Big Cock swallowing
33%
My shemale GF Part 3
Christy and I are on the couch, we had just woke up, I have a butt plug in and slept with it in cause she was going to fuck me today. She has a Pink G-string on and a Pink bra with her G-string pushed to the side for her cock. Me I'm wearing Metal Mulisha boxers and a Tyler, the creator T-shirt on, ... Read full Story
shemale lover 2012-07-09 3,518 anal shemale cum jerking oral
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 7,032 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
50%
Devastating and dominating
Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... Read full Story
shemale lover 2012-01-29 5,105 Masturbation sucking Creampie Latex fucking
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 9,467 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
88%
Seattle Weekend
Saturday morning and such a beautiful day nice and cool morning I went for a run. I consider myself in fairly good shape for my age but I try and make it to the top of a hill in our neighborhood. I get winded fairly quickly. Coming down the hill I ran into a nice looking athletic girl, maybe 38 year... Read full Story
Jon Paul 2018-08-09 10,072 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
66%
Sex in the kitchen with my hubby's friend - a cop
Ever since my wedding last year, I enjoy a great time with my hubby who loves me so much and takes care of me so much. Since he is married and having another family, he doesn’t stay with me all the time, but comes and stays at least 2 or 3 days in a month and we literally celebrate those nights wit... Read full Story
Manusha Tranny 2021-10-14 5,223 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
92%
How do you do it?
this is just a quick little story. or really a question i could say. at first trannys were a complete joke for me. my friend tricked me into watching the porn cause the guy looked like a girl and bam when i saw the penis i turned the video off. I couldnt stop thinking about it to the point where ... Read full Story
coolguy456 2015-02-15 3,617 Teen (18+) Shemale Fucks Guy Ladyboy big ass
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 5,143 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
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 6,541 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale