Sort by
Relevancy

Free Stories

40%
Fantasy Came True
Almost a week ago I had the pleasure meeting almost local tgirl escort. This girl was perfect for my fantasy with shaved 5in. cock and she already had top off. After introduction was over, I sat on edge bed pulled my shorts off. Perky bcup Tits were at perfect height to suck one nipple while rubb... Read full Story
Jimishard 2018-05-25 4,072 tranny small cock fantasy
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 9,785 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
50%
The BIG COCK that I will eat.
ENGLISH: Hello friends. In the link below, you can see the tranny cock that will fuck me in the days to come. I saw her advertised on the internet, I picked up the phone and called, I will see her when her clinical tests are negative for sexually transmitted diseases, because I will surely swallow... Read full Story
cuchillo 2020-09-18 8,237 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Homemade cum in mouth brunette ts swallow cum
100%
Alone at home
Living with my religious parents didn't provide many opportunities to spend time alone to enjoy myself. Only openings I found where, when showering, and occasionally when my parents travel, though that was not very often. I shared my room with my lil siblings, and since they were young and curious, ... Read full Story
Sara M. 2024-01-16 7,035 solo Lingerie small cock Homemade sissy femboy
100%
It Started by Waxing and Ended Up Something Else
The Best sex I ever had? With a 29 year old female about 7 years ago, (2017) Her alleged name was Ashlee, How did I know her? For about 3 years I was paying for a total body etc. professional waxing, with Karen who had a business in Lincoln. People have not lived until they have gone through... Read full Story
Linda Tiffany Vista 2024-05-09 4,341 Crossdresser blonde Shemale and Girl domination Sex Toys small cock Homemade
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 7,545 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
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 97,144 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
81%
My first time getting a big cock in my ass
I got talking with a relatively local guy, much older than us, but had a thick 8.5" uncut cock, which was perfect for what I wanted to watch enter my Mrs. Our messages went something like this... Me "Did you want to meet up first?" Him "If you want" Me "We'll chat about a plan, then I'll... Read full Story
BalkanLoco91Ri 2019-08-26 8,146 Amateur Cumshot Bareback Creampie Blowjob Big Cock Homemade pov Ass to Mouth
83%
Tranny gang bang
It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place. What was I doing in here? In truth I did not know but I was 16, horny and wanted to ... Read full Story
shemale lover 2015-02-27 6,856 tranny Cumshot suck gangbang facial oral sex bukkake
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 6,076 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale
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 17,054 Cumshot Blowjob Big Cock domination Interracial Homemade cum in mouth ladyboy ts thailand ladyboy shemale fuck guys virgin ass bottom boy bottom virgin
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 3,091 Amateur Big Tits Masturbation Big Cock Ebony Guy Fucks Shemale big ass Homemade Ass to Mouth cum in mouth
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 4,952 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
KING OF TRANNY CHASERS ENTRY 2
LAST YEAR TO CELEBRATE MY BIRTHDAY I DECIDED TO FULFILL ONE OF MY SEXUAL FANTASITES. I HAD BEEN WITH 2 CIS WOMEN SEVERAL TIMES BUT NEVER HAD I BEEN WITH 2 TRANNIES. MY BIRTHDAY WAS ON A FRIDAY SO I SPENT THAT DAY AND THE NEXT CELEBRATING WITH MY FAMILY AND GINA..THAT SUNDAY I SET UP AND PLANNE... Read full Story
Ghostface drillah 2024-07-04 3,599 anal Amateur Group Sex Big Tits Cumshot Shemale Fucks Guy Fetish Big Cock Guy Fucks Shemale big ass Homemade Ass to Mouth shemale fucks shemale
62%
My ladyboy in a bar fantasy
Our reader, Mark, writes about his ultimate fantasy about meeting a ladyboy in a bar and petting her right there through her clothes. Things like that always arouse me, and what is more, Mark has a very remarkable and vivid writing style. Most erotic read! While I haven't experienced one to date,... Read full Story
shemale lover 2015-07-07 5,598 tranny Asian dick
71%
Thai Ladyboy Interview
An Afternoon With Some Thai Ladyboys I spent this afternoon with 6 Thai ladyboys. No, don't go thinking that I tried them out. I didn't. I spent a few hours chatting with them, finding about them, trying to understand what makes them tick and learning about their experiences and the guys who util... Read full Story
shemale lover 2012-08-11 13,079 Fetish Asian Ladyboy
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 8,266 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade 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 5,966 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
50%
Sex with security guard in the apartment..!
I always fantasize about exploring the unlimited possibilities of cross-dressing and exposing myself in public such as dressing up and clicking hot pics in public places, seducing men and get picked up from pubs, having sex in car and on the roadside, etc., and some of my fantasies have already come... Read full Story
Manusha Tranny 2021-10-18 9,018 Crossdresser Cumshot Outdoor Blowjob Big Cock Asian Ladyboy cum in mouth
45%
Threesome with random muslim men from Dubai -
As you all know, most of the meetings with my clients happen in good 3-star or 4-star hotels. Clients normally visit my hotel room and have fun. This exciting session happened during my stay in a 3-star hotel room in Bangalore on March 1st and 2nd. I had bookings for both the days and was prepare... Read full Story
Manusha Tranny 2021-10-14 9,447 Crossdresser Cumshot Outdoor threesome Blowjob Big Cock Asian Ladyboy gangbang domination Guy Fucks Shemale Ass to Mouth cum in mouth
79%
Fucked and sucked by a ladyboy
Our reader Maxie wants to share what it is like to be fucked up bottom by a ladyboy and getting a blowjob from her at the same time. Seems very exciting, what do you think? ;) On a recent visit to Thailand I went further than I ever thought I would. I picked up a "young lady" Bangkok wh... Read full Story
shemale lover 2015-02-09 10,563 suck Ladyboy fucking
80%
Ladyboy Loves Up The Midwest
When Jasmine, a Thai ladyboy, moved into a small town in Iowa the locals didn't know what had hit them. She was instantly the talk of the town; initially for being so different and exotic but once she opened her club her reputation spread right across the county and state line. It was only a real... Read full Story
shemale lover 2011-10-08 6,572 Blowjob Ladyboy massage
85%
Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
shemale lover 2014-09-17 62,808 suck Bareback Asian Ladyboy ass fucking
100%
Lady and the Cop continued
The next night Regina got a visit from. Larry the cop who openly declared war on shemales and trannies. He was working a homicide where a trannie friend had been killed in her apartment. Larry was a known shemale hater and he never failed to express his opinions. Tonight he was in her apartment to ... Read full Story
Regina10 2018-03-06 5,040 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
My wife turned me into her tranny
It all started after our marriage. We have been together for 12 months when she asked me if I would be willing to have her dress me up like a female as this was one of her fantasies. Little did I know where this would lead us to. She was very secretive about her job and I did not bother to ask, I fi... Read full Story
TRTRAIN 2024-01-15 9,727 Stockings Crossdresser Amateur Shemale and Girl domination pantyhose Homemade sissy shemale fucks female
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 5,483 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
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 5,736 sucking shemale cum
70%
First Tranny Experience_Part 1
I met a girl that was fantastic, maybe a body builder, but she was a smoker. We became just casual friends when someone told me she was a transgender. She moved we lost touch but that short friendship introduced me to the attraction to transgendered girls. I really wanted to get to get close to some... Read full Story
Jon Paul 2018-08-06 7,421 Group Sex Bareback Creampie Blowjob Asian Ladyboy cum in mouth
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 6,013 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
100%
Philippines vacation with a Dominant Big Cock Ladyboy (Part II)
Please read the initial story to get proper context. I spent a 9-day vacation in the Philippines with a sexy and super sweet 34-year old Filipina Ladyboy I met online and developed a relationship with before traveling to meet her. It was the first and only time to visit the Philippines. Less t... Read full Story
AllenB 2024-08-07 4,173 Amateur Asian Ladyboy
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,877 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
100%
First time with a cute ladyboy
It had been a long week at work. So I decided to go to the Sound Factory for a drink and maybe get lucky with the ladies. As soon as I got to the bar, I spotted a beautiful asian lady wearing leggings with pantyhose and a sexy little top. She offered to buy me a drink, who am I to refuse. So we had... Read full Story
shemale lover 2013-05-07 11,427 Cumshot suck Asian Ladyboy pantyhose
100%
First Tranny Experience_Part 2
I had said good bye to her at her door and drove home. I got home at a decent hour and went to bed. The following day at soccer practice, I could only think about how wild a time we had together and began fantasizing about the whole affair when my cell phone went off. To my surprise, it was Kim s... Read full Story
Jon Paul 2018-08-06 5,177 Group Sex Bareback Creampie Blowjob Asian Ladyboy
86%
Tranny Stories Made Me Do It
I’ve never had trouble finding a girlfriend. I’m a reasonably handsome guy and chicks love me. I’m into porn no more than any other guy, and I started reading tranny stories out of boredom. In time, my curiosity took over. I imagined that guys wanted to fuck shemales because tha... Read full Story
shemale lover 2016-02-14 6,677 tranny face fucking
33%
NERVOUS MEETING
On a cool fall evening I was walking about town when I came across a sign outside a coffee shop saying, "lonely? stop in for a cup and new friends". It was plain except for the light rainbow in the center of the sign. Being curious and also a bit lonely myself, I stepped inside. It was nothing m... Read full Story
77James 2022-01-03 2,540 Small Tits Homemade cum in mouth diaper
50%
Being Shemale
Every night I wear make up and dress up in a sexy lingerie. I stand in my balcony late night trying to lure men and women driving on the road. Last night a truck driver stopped near my house to inspect his vehicle. During his inspection he suddenly saw a long legged booty women in the balcony inf... Read full Story
babydriver 2024-06-04 4,251 Stockings Crossdresser solo Outdoor Ebony Asian Ladyboy Lingerie big ass sissy femboy
82%
Worry Free Shemales Dating Can happen To You Too
"There is no such a thing as an attractive tranny" was one of my lifetime mantras. Growing up in Bay Area, it was easy for me to spot and recognize all of those masculine bodies dressed in female clothes. Their huge feet in high heels looked as a combination form hell. Free shemales dating... Read full Story
shemale lover 2016-08-18 7,198 tranny Small Tits Creampie
100%
My favorite time with a man as a Tgirl
I was in the dance clubs with my friends and we were very sexy dressed in heels and low tops and I was in high heels and a mini dress that was flowers all around it. My ass looked so big and round in that dress. It was low on my big boobs and very tight so my boobs looked like they have coming out. ... Read full Story
shemale lover 2012-09-29 2,924 first time tranny anal sex Creampie
100%
The reason why I became a crossdresser
At first, I was just a straight and ordinary boy who was into sexy lingerie, stockings and heels. But one day, I suddenly thought that I wanted to try on my mom's panties, stockings, and high heels. So I did it. It was so excited and I started to get addicted to cross-dressing. Before dres... Read full Story
cdmisato 2024-02-28 7,351 Crossdresser Asian Ladyboy sissy
100%
Camming down the rabbit hole Ch4
It was the morning after the night before, and as I stretched under the bedsheets, a smile spread across my face. Remembering last night’s events, I felt myself stir a little and pressure from the panties I had on adding to the arousal. It has been a while since I had morning wood after a big show, ... Read full Story
Dani_does_Dallas 2021-09-06 4,343 Crossdresser solo Amateur Cumshot Lingerie Sex Toys Homemade pov webcams
100%
Amy The Tranny Part 1
I met Amy at an adult theatre in town. She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private booth and once inside, went over her price for some adult fun. She told me I couldn't fuck her as she was on her per... Read full Story
shemale lover 2011-12-14 5,173 shemales hardcore anal sex Big Cock
76%
Tranny hooker
I was out late looking for a cheap hooker with £15 in my wallet I should at least get a blowjob. After 20 minutes of searching I see a young girl stood on the corner. I pull up along side her she tall long legs short skirt stockings m holdups long dark hair as she bends down I tell her how muc... Read full Story
shemale lover 2012-01-05 5,065 first time shemales Fetish
94%
My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
Betty D 2021-01-18 9,126 first time Crossdresser Amateur Cumshot Fetish Blowjob Mature Homemade mini skirt small cocks black panties obese
100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 5,517 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
50%
La bonne chair masculine…
La bonne chair masculine… La brise caressait mes mamelons gonflés me donnant des frissons agréables. Les deux verres de Riesling avaient également contribué à mon excitation. Mon entre-jambe brûlait comme si le soleil qui disparaissait avait soufflé toute son énergie thermique dans mon intérieur... Read full Story
hippocampus_171 2023-04-23 1,395 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminization cum in mouth gaycd virile
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 4,214 sucking Fetish Ladyboy rimjob
70%
transexual watcher
so I was in the local sex store in the back they show videos . I was watching transexual babysitters 6 when I met her. She was blonde with pink highlights. She ask if I had ever fucked a tranny. Before I could answer she was completely engulging my pierced cock in her mouth. I was completely e... Read full Story
yodaslut 2015-01-03 3,794 first tranny
73%
My first experience with a tranny
ENGLISH: I want to tell you about my first sexual experience with a transsexual in 2018. I was a bit drunk and got horny, I searched the internet and found a brunette tranny with 7 inches of cock, wavy hair, young and attractive. She had an HIV negative health card. We went to the motel and I was... Read full Story
cuchillo 2020-08-28 7,864 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Lingerie cum in mouth brunette ts fingers cocksuck
100%
My first time having sex with a Tranny
I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... Read full Story
Joe22lovests 2021-09-15 12,469 first time Shemale Fucks Guy Blowjob Big Cock
100%
I was a Top before this experience
She was tall, 6 feet probably, a white colombian beauty, green eyes. Pretty gym body, strong but feminine, don't know how that works, but this was a work of art. Sweet but commanding voice, you know, similar to that voice that tells you that it's recalculating your GPS route or to turn left right no... Read full Story
Mizty 2022-11-03 7,047 Amateur Cumshot Shemale Fucks Guy Blowjob Big Cock Homemade
80%
What I like
I like cum from cocks, a copious creampie dripping from a pussy, or licked off a warm body. I'm an older guy but I'm still fit, active and horny all the time. I like to masturbate while looking at porn with a prostate stimulator up my ass, wearing nipple clamps and a cock ring after smoking some pot... Read full Story
SylvesterLeChat 2023-08-15 5,159 Masturbation Creampie Blowjob Big Cock Ladyboy Mature small cock sissy cum in mouth
75%
Tranny and Me Meet The Milf
This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the week... Read full Story
shemale lover 2011-08-08 3,618 shemales hardcore Group Sex
100%
A Black Tranny Fantasy
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sleeping with a black shemale was about to come true. She paused... Read full Story
shemale lover 2012-02-08 5,797 Masturbation oral black tranny
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
Lisawantsu7 2014-09-02 7,054 hardcore Creampie Big Cock ass fucking Shemale and Girl
95%
A Black Tranny Fantasy
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sl**ping with a black shemale was about to come true. She paused... Read full Story
shemale lover 2014-12-03 6,147 tranny Cumshot suck ass fucking Interracial
100%
First Time Sex With Tranny
Wow - if you have ever wondered what it would be like to be with a TS girl, this would be a great place to start. Just got this from a “friend” of mine who wanted to write about his first TSgirl experience. Can’t say for sure if it’s 100% true, but who cares? I do know that they were together so ... Read full Story
sach 2015-11-16 8,395 first time tranny suck stroking mutual sex