Sort by
Relevancy

Free Stories

89%
Lucy change chapter 3
It was late enough when we got out of the shower, almost 4pm. I dried myself quite quickly, as I always do, and lay out on the bed to ‘air out’. Lucy, having shorter hair, was quite quick drying as well, though she spent longer walking around the apartment looking for this or that. I was glad of the... Read full Story
Alex1090 2013-12-17 4,802 anal tranny Cumshot Shemale Fucks Guy Big Cock
64%
Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... Read full Story
sach 2015-11-16 7,435 Big Cock ass licking redhead rimming Shemale on Guy
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 96,129 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
83%
Wife Left Me so I Could be a Girl
I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with... Read full Story
ASSEaster5678 2018-07-09 10,548 Shemale Fucks Guy Ladyboy Mature
100%
All Woman and More
It was one of those soft southern nights you hear about in movies and old soft rock songs. I could smell the long leaf pines and the moon was nearly full. I had been on my own for so long that it rarely bothered me as it did in my youth. That lonely feeling that never quite goes away. Now it came on... Read full Story
Windmillchaser 2018-09-20 10,712 Bareback Shemale Fucks Guy Big Cock sensual romantic encounters Erotic Fiction
100%
Decisions, decisions.
So if you have read my stuff I’ve posted before I was with a tranny named Nicole for awhile but she left for work last year so after she left I actually started dating normal again went back to girls but never forgot her. I’ve hid the dildo and all my secrets from my current girlfriend for almost a ... Read full Story
Duke04 2019-07-25 7,940 Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth
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 7,537 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Lingerie cum in mouth brunette ts fingers cocksuck
100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 7,162 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,611 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,737 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial 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 12,044 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy cum in mouth
100%
Captain John’s Playmate
Alessia Travestita’s Adventures – Episode 1 – Captain John’s Playmate. It was forecast to be a gloriously warm and sunny day, clear blue skies with a gentle warm breeze from the South. So I decided to leave the town behind and head out into the countryside for the day, get some fresh air, toning ex... Read full Story
Alessia Travestita 2023-07-13 4,894 anal Crossdresser Bareback Blowjob blonde Big Cock Lingerie Guy Fucks Shemale Mature Ass to Mouth cum in mouth
93%
Homework
Daniel was a 15 year old teenager, like any boy his age, he was full of hormones and sexual fantasies for every pretty girl that passed in front of him. In the last weeks of the school year, the history teacher had a child and was absent from school, being replaced by teacher Marlene, a trans woman.... Read full Story
haroldãosanguebom 2024-01-09 7,294 Shemale Fucks Guy Big Cock Mature
100%
Hits, Misses: G
Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibili... Read full Story
bybaking 2024-02-06 4,919 anal Amateur Cumshot Bareback Big Cock Ebony Guy Fucks Shemale Interracial black Tgirl
100%
Police House Call
My heart was beating a mile a minute when I heard the knock on my door. I was hoping that it might be Beau, or Larry, or if I’m lucky it would be Tom Cobb. He asked me to call him Tommy. I had been thinking about him recently. Bo and I had banged the night before, but I was as horny as ever. Larry w... Read full Story
Regina10 2024-04-19 3,662 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
50%
Liberty meeting , Chapter2
When she strums again on her keyboard, I feel that it sinks imperceptibly but inexorably into me. - Relax my darling, Mirella told me, masturbating me with an expert hand. At the start, I have rather pleasant sensations. Being completely submissive to this machine without being able to stop... Read full Story
sandratvtg 2024-06-20 2,011 anal Stockings Shemale Fucks Guy Lingerie domination Sex Toys femboy
100%
The Story of Stephanie (Chapter 10)
A year had passed since my night with Alan. I'd taken a back seat from the dressing. Only now and again was I getting the urge. I was trying to live a normal, single mans life. Going out with friends, going on dates etc. I had one or two girlfriends in that time. One in particular, who I regretted n... Read full Story
Stephanie Wild 2024-07-14 1,753 anal Stockings Crossdresser Amateur Blowjob Big Cock Lingerie Guy Fucks Shemale
80%
She trained me
I was sent to Aunt Fergie when my parents were killed. She is about 5'7" and 200 lbs she was your stereotypical aunt with some fat and wide hips and big breast. She picked me up at the bus station in her car. She said," My household is different and special I have girls who you will ... Read full Story
shemale lover 2012-02-17 5,948 anal Big Tits Shemale Fucks Guy
100%
Jesse's Dream Job - The First Day
Jesse didn't want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had ne... Read full Story
shemale lover 2012-12-20 9,656 hardcore Cumshot Shemale Fucks Guy ass fucking handjob
100%
Caught and Punished
I had walked into the mall on a Friday afternoon with a group of my friends, Steve, Bill and Ryan. The plan was pretty' simple; Bill would stand guard while Steve, Ryan and me went into the jewelry store. Steve and Ryan would distract the clerk while I went around to one of the glass cases and picke... Read full Story
shemale lover 2013-01-29 9,471 anal sex Shemale Fucks Guy Blowjob gagging deeptroat
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 18,183 Shemale Fucks Guy
85%
My First Filling
It was my 18th birthday and my friends were getting on my back about still being a virgin. They’d pick on me about having not had sex with a gir yet, but they didn’t know that I fantasied about something other than a girl, I lusted and craved myself a trans partner. All the fun of a girl but with a ... Read full Story
JessicaEdwards 2018-05-04 21,504 Stockings blonde Big Cock Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
80%
Alex pt. 3
After that b****** in the bathroom, me and Alex hung out a couple times. we went to a bar, and I ordered a beer, Alex had vodka and cranberry. I didn't want to get too drunk, because whenever I do I can't seem to get hard. Of course, I knew all along that somehow that night I would finally... Read full Story
Mike212 2018-07-02 6,158 Teen (18+) Blowjob Big Cock Ladyboy Guy Fucks Shemale Frottage 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 9,209 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
94%
Flight cancelled
I was on my way back from a long business trip to Chattanooga, Tennessee and deciding to hit the airport bar during my layover. As I walked up to the bar I noticed there was only one seat open. I took it. I ordered my favorite drink, an old fashioned neat with makers mark. As I sat there waiting for... Read full Story
Jsmithsub 2019-10-31 24,486 big dick Group Sex Bareback Shemale Fucks Guy Fetish Blowjob Big Cock pissing Ebony domination cum in mouth monster cock gang bang
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 17,422 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 11,417 Shemale Fucks Guy Blowjob Big Cock domination Ass to Mouth
100%
Return to Luisa Tavares
Everyone at the office asked my why I was limping. I told them I had fallen playing tennis. The truth was, I had been mercilessly fucked by Luisa Tavares. Her huge cock had destroyed my asshole. Can you imagine someone thrusting a can of Coca Cola up your butt again and again with tremendous forc... Read full Story
hotspur 2020-04-14 15,763 Bareback Shemale Fucks Guy Blowjob Big Cock Shemale and Girl cum in mouth
91%
Hot Slutty Sissy
Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... Read full Story
Regina10 2020-08-14 6,898 Crossdresser Cumshot Bareback Fetish Blowjob blonde Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
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 7,820 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Homemade cum in mouth brunette ts swallow cum
100%
College project surprise
So this story happened while I was still in college and remains without doubt, the craziest, most exciting experience of my life. So I the story begins one day when I walking to class. I went to a big university so my walk was quite long, and the first 1/3 was just through off our campus housin... Read full Story
Jsmithsub 2020-09-16 21,239 Group Sex Bareback Shemale Fucks Guy Fetish threesome Big Cock Ebony domination Ass to Mouth cum in mouth
100%
The Tip for A Tip
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com Thank you. Now Enjoy! COVID had shook up my world pretty bad. Furloughed from my day job, I had to make ends meet. I started doing food delivery for the local ride share company... Read full Story
therefill05 2020-12-10 6,736 Cumshot Latina Bareback Shemale Fucks Guy Blowjob Big Cock domination cum in mouth
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,743 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 11,966 first time Shemale Fucks Guy Blowjob Big Cock
100%
Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
darrell 2024-02-02 5,605 Shemale Fucks Guy Blowjob blonde Big Cock Mature deepthroat cum in mouth toe sucking Fisting Anal
100%
My Favorite Top Tranny
Kevin:I know you're secret, you have a huge cock under your panties and like to a man that turns into your bitch boy when you fuck. guess what I love a tranny that wants to top. I'm proud so I don't have to keep it a secret. Rosie:*I blush deeply, my cheeks turning bright red, as I try to maintai... Read full Story
KevinRichardJudd 2024-06-27 2,593 Shemale Fucks Guy Big Cock