Sort by
Relevancy

Free Stories

100%
I wanna fuck almost everyday
I can't stop thinking to be Double penetrated for two men at the same time.... It makes me feel I'm insatiable gurl... Two Big cocks mmmmmmm after been fucked for so long ... I will never go back... And certainly I will totally satisfied and addicted to it...... Read full Story
Bellasohot 2022-07-13 3,804 Crossdresser Amateur Latina Bareback threesome Big Cock Ladyboy Lingerie Guy Fucks Shemale Mature Ass to Mouth double anal
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
Chrissy Tunnell 2022-12-01 3,623 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,597 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Got my ass pounded in Miami by a tranny escort
Got my ass pounded in Miami by a beautiful tranny escort with a 10 inch thick cock. Years ago I was in Miami for a business trip. Four days just me in my hotel room. I decided to treat myself to some of the X rated channels that my hotel provided. As usual I went straight to the tranny porn.... Read full Story
My Shemale Attraction 2023-01-03 6,742 Amateur Big Tits Masturbation Creampie Shemale Fucks Guy Blowjob
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,679 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
IRL: Magic City Classic
I get many requests asking me to share more of my real life experiences. Several of my stories contain elements of things that actually happened to me. But, I’ve decided to put together a new e-Book of my personal sexcapades. So, in that vein, here’s the first installment of my ‘In Real Life’ (IRL) ... Read full Story
Faggyboi and Puzziboi 2023-07-14 4,460 anal Crossdresser Bareback Blowjob Guy Fucks Shemale femboy bbc faggot dl puzziboi faggy
100%
A new start in life
“In life, finding a voice is speaking and living the truth. Each of you is an original. Each of you has a distinctive voice. When you find it, your story will be told. You will be heard.” John, living outside Boston, being your average accountant working with Gillette, had gone through a messy di... Read full Story
Jon Paul 2024-05-09 2,809 anal Amateur Shemale Fucks Guy Big Cock Guy Fucks Shemale small cock big ass
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 768 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
100%
My Noisy Upstairs Neighbors Part 2
In my previous post, "My Noisy Upstairs Neighbors," I shared the story of how I finally confronted my upstairs neighbors about the constant noise they were making. However, this encounter took a devastating turn, leading to a traumatic and deeply violating experience, when they raped me and filmed i... Read full Story
Chrissy Tunnell 2024-07-16 448 Crossdresser Cumshot Fetish domination Guy Fucks Shemale Mature Frottage sissy femboy
92%
Domination Fantasy
I wake out of a daze to feel water running down my body. I am somehow naked and i dont remember going into the locker room shower or taking my clothes off. The last thing I remember is meeting this beautiful girl named Crystal at the game and her getting my drink from the concession stand. "... Read full Story
KevinKraven 2012-09-13 7,847 Ebony domination
100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 5,100 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Pygmalion
Some of the coed students in Professor Higgins' Sculpture 101 class regard him as a sexist or, as Amanda Blake describes him, as if she were living back in the sixties, "a male sexist pig." He does have an eye for the ladies, I'll grant you that (he's ogled me enough times!), but what man ... Read full Story
shemale lover 2013-02-22 5,143 hardcore Big Cock ass fucking Guy Fucks Shemale ass fuck
86%
Shemale Sherri Arrested for Theft
Sherri had had a tough night. First she was involved a little confrontation with a skinny bitch who thought that just because she had a vagina made her hotter than Sherri (and no, it didn’t), and then Sherri borrowed a bottle of whiskey from some advertising executives who called the police on... Read full Story
shemale lover 2013-06-29 5,209 tranny ass Cumshot shemale fingering domination
100%
Traci the Maid
Traci had gotten a job as a maid in a rich man's house. She looked just like any blond 26-year old woman - long legs, slender waist and high size C breasts. She had a heart-shaped face and giggled at all the right times. Only Traci had a secret that nobody at her knew job knew about - she had a 6&qu... Read full Story
shemale lover 2013-07-19 5,343 Stockings Cumshot blonde Uniform Guy Fucks Shemale
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 9,440 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,604 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
44%
A Lover Wet Dream
I fantasized about my tranny girlfriend fucking me the other night. I dreamt that she told me to be wearing my blue teddy, earring I got me for for birthday, thigh-high white stockings, and black heels. I came home all sweaty and dirty from a long day’s work, and told her to get me a beer from t... Read full Story
ASSEaster5678 2018-05-02 3,096 Bareback Uniform Guy Fucks Shemale deep penetration dreaming
100%
The Game 2
That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... Read full Story
chris1989r 2022-01-24 4,410 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
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 2,763 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,584 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 5,814 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
100%
A Fantasy - Part 2
Paula begins to grown, ohhing and ahhing. I suck hard and swirl my tongue around on the head of her cock. Sharon has pushed her dildo all the way into my ass and begins to pump my ass with a slow, steady rhythm. Paula holds my head in place and begins to thrust her cock into my mouth harder. "I'm go... Read full Story
swollenrooster 2023-09-20 5,018 Group Sex Cumshot Shemale Fucks Guy Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
100%
She Loves Dirty Talk Too
Sexy TS Girl: Hiii! How are you? Thanks for being my new friend. I have so much love forssz you, my friend. Don't hesitate to like and comment one or two photos of me that you like. We can also chat... Love, love, love you, sexy man. HardRock: I really enjoyed looking at your galleries.... Read full Story
Hardrock51Fifty 2024-05-17 3,079 anal Amateur Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock domination Guy Fucks Shemale Ass to Mouth cum in mouth dirty talk
100%
My surprise Part 2
I managed to force myself free. I slammed my back against the cubicle door and I looked into her eyes. She was beautiful, amazing eyes, great face, nice pair of tits and a great body. She stood up, pulled her tights thong and skirt up and calmly walked by me touching my crotch and winking at the sam... Read full Story
shemale lover 2012-02-21 2,212 hardcore oral sex Guy Fucks Shemale
100%
Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
shemale lover 2013-01-30 7,907 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
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 5,986 sucking jerking domination Guy Fucks Shemale big boobs
95%
Mutual Fuck With Art Student
It was the beginning of the semester at the Art Institute and I was pretty excited about my new schedule. Professor Ludovian always brought interesting nude models to his classes, and his tips on how to draw the human body were most useful. I had learned a lot in the intermediate class but now in th... Read full Story
shemale lover 2013-04-27 7,889 first time sucking Shemale Fucks Guy fingering Guy Fucks Shemale
100%
My first and only
I contacted her on a chat line, we arranged to meet she was working as a nurse in london and was from the Philipines. I met her at her flat rang the bell she opened the door wearing a red dressing gown, I could see the cuves of her body and her beautiful cleavage was showing. She had long black hair... Read full Story
shemale lover 2013-05-07 5,481 Stockings sucking ass licking Guy Fucks Shemale 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 4,448 sucking Shemale Fucks Guy ass fucking Guy Fucks Shemale stroking
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 6,021 Teen (18+) Blowjob Big Cock Ladyboy Guy Fucks Shemale Frottage Homemade
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 9,880 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
80%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 5,970 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth cum in mouth
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 22,142 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
100%
Bimini (part2)
Emily was introduced to me by my friend Jan at a night club. ‘Em’ is a 19 y/o t-girl and absolutely adorable figure and very sexy legs. Well after leaving me at the club with Emily, I had invited her to fly to Bimini the next day for a long weekend . If you read part 1 you will know. Waking up... Read full Story
Jon Paul 2021-04-19 3,499 Bareback Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale 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 3,713 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature 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 6,517 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale