Sort by
Relevancy

Free Stories

95%
Halloween Night Again
Last October my girlfriend Kelly and I were drinking wine and playing cribbage on a cold, rainy night. After dating her for six months we usually stayed in on weekends. I consider myself very lucky to be dating her. She is an incredibly beautiful brunette and has a perfect 36C-24-26 figure on her 5'... Read full Story
ASSEaster5678 2018-10-29 13,388 Shemale Fucks Guy Guy Fucks Shemale Halloween
66%
The Audition
New York City wasn't a bad palce to be back then. I was a student working at an office job and doing what I enjoyed. That was being a musician. Lots of weekend and night gigs at cocktail parties, lounges and so on. There were a few pianists I worked for as standing time-keeper ( bass play... Read full Story
iluvgurls 2018-11-12 5,923 Stockings Cumshot Fetish Blowjob blonde Lingerie Guy Fucks Shemale cum in mouth
80%
Flying High
Flying High Janice loved working as an airline hostess. Traveling all around the world enabled her to meet many people which she enjoyed doing, however she always felt alone, until one day while they were flying at 30,000 feet the plane suddenly encountered a lot of turbulence which caugh... Read full Story
iluvgurls 2018-11-14 3,947 Cumshot Fetish Blowjob Lingerie Guy Fucks Shemale
88%
LONDON CINEMA LIAISON
When I lived in London back in the 80s and 90s, I would often sneak off to a porn cinema with stockings, suspenders and knickers under my suit. My wife didn’t much like sex, so this was a release for me to get away from home and have some sexy fun. Once I had found a suitable seat I would ease down ... Read full Story
GinaG 2018-12-14 7,375 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
80%
Wrong Vampire
I consider myself a fairly tolerant person. I judge each person on their merits, not their skin color, gender or even sexual orientation. I'm even in favor of the Vampire Rights Amendment, but I must admit, unlike other groups people discriminate against, they make me uneasy. They claim that all the... Read full Story
ASSEaster5678 2019-04-23 6,834 Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth vampire
50%
There is love, but war
All characters in this story are eighteen years of age or older.* *The following story is inspired by Miss Evie Hyde's "Slut-Box Challenge" story. The following is written with permission from her to use her premise with my own characters and situation* Billy checked his phone when he got th... Read full Story
ASSEaster5678 2019-07-04 3,709 Guy Fucks Shemale bullies
60%
The Greatest Liar, Date With The Devil
The Greatest Liar, Trans Erotica With A Purpose © Alexandra Rios 2019, all rights reserved Disclaimer This is a work of fiction. All characters (including the narrator), firms, business entities, organizations, teams, products, medical providers, medicines, governments, government officials, c... Read full Story
the greatest liar 2019-08-20 4,383 Big Tits Bareback Creampie Guy Fucks Shemale
100%
Sports Bar Pre-drink
Sitting on the chair leaning against the bar, Steven sat quietly sipping on his rum and coke. It was a fairly quiet night at the local sports bar he often ventured to after work to wind down from his work shift. Steven looked up at the door as a small group of women walked through laughing and ta... Read full Story
Master VeeJay 2019-09-27 9,680 Big Tits Blowjob Asian Guy Fucks Shemale
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,909 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
Seduced At The Gloryhole
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com Enjoy! Golden blonde hair that rested just past her shoulder, piercing blue eyes, full luscious red lips with colorful sleeves of tatoo’d arms. Wow, she was immaculate. She locked ey... Read full Story
therefill05 2020-12-10 9,733 Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale Interracial 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 2,958 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,847 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
80%
Amber
The summer after high school I moved into this cheap hotel downtown. I'd been working in the mailroom for a large company, and really needed to get my own place, but I didn't have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I ha... Read full Story
ambersissy 2021-04-23 5,673 Crossdresser Amateur Big Cock Guy Fucks Shemale Interracial cum in mouth
77%
Amber part 2
After the night with Hollywood the next day seemed to drag by. As soon as I got back to my room, I quickly stripped. Falling back onto my bed, I slowly masturbated, my mind still reeling from last night. I'd actually sucked cock, not only that, but I liked it, I liked it a lot, and wanted to do ... Read full Story
ambersissy 2021-04-23 3,773 Crossdresser Amateur Blowjob Big Cock Guy Fucks Shemale Interracial
100%
The four of us
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-08-02 4,489 Group Sex Big Tits Cumshot Bareback Creampie Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
91%
Aby my trans daughter
I am 50 and great shemale fan. I met Aby through PlanetRomio during covid lockdown. I was alone at home that time and i was searching for some good trans or shemale. So Aby so my profile and sent me message. I immediately replied. we exchanged our contacts and then shifted our chat to Whatsapp. ... Read full Story
Stud4Shemale 2022-01-03 4,663 Crossdresser Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock Asian Guy Fucks Shemale cum in mouth
100%
Pizza Delivery
She wraps her hands around the back of his head and shoves her cock harder and further into his throat. She can hear him gag and saliva burble in his throat. “FUCK I’ve needed this!” She says, pulling her cock out of his mouth and letting him take a deep gasping breath. “Holy fuck,” he says, cat... Read full Story
ghostpeople 2022-11-22 6,233 Bareback Shemale Fucks Guy Blowjob Big Cock Uniform Ass to Mouth cum in mouth
100%
First time with big surprise
My first story translated into English, I hope you like it. It was late at night, I had been drinking with friends and was on my way home. I am a man in his early 30s, smartly dressed and looking quite attractive. The night was beautiful, clear sky, warm and in the city were some people on the ... Read full Story
Marten1201 2023-01-06 7,098 Big Tits Bareback Creampie Shemale Fucks Guy blonde Big Cock
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 7,100 Crossdresser Lingerie domination Sex Toys femboy forced webcams
100%
Ravaged by Daddy
For anyone who loves wearing high heels and dressing up to get ravaged by your hungry Daddy. I imagine you laying on your side as I run my strong hands up and down your smooth, soft legs and across your feet. I slowly slide them upwards until I'm caressing and squeezing your thighs. You watch me ... Read full Story
TheWinkster 2023-08-29 5,488 anal Cumshot Bareback Creampie Guy Fucks Shemale
66%
You Just Don't Care...
“Oh, naw! I’m straight,” the slim, sinewy-built man replied matter-of-factly to revelation. “What’s that got to do with anything,” cooed the milk-chocolate-complected vixen, playfully grazing the man’s hard chest. “Damn, why you ask it like that,” he scoffed. “Like what,” the sing-songy-voiced c... Read full Story
Faggyboi and Puzziboi 2023-10-19 6,198 anal Crossdresser Ebony Guy Fucks Shemale sissy femboy bbc faggot faggyboi puzziboi
100%
Vegas Encounter- Part trois
This was to be Jack’s second night in Las Vegas, he had met his online pen pal Diane, and her roommate Holli, the previous day and the three hit it off with an evening of sex. Jack had spent the day getting to know Holli, and the day proved to be unbelievable. Holli and Jack took a drive into the mo... Read full Story
Jon Paul 2023-12-24 6,379 anal Cumshot Bareback Creampie Guy Fucks Shemale cum in mouth
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 3,928 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
83%
My first time with a guy
MY FIRST TIME WITH A GUY Another true story it’s kind of long but I think you will enjoy it I lived west of Lake Worth Florida. At that time we were surrounded by 1500 Acres of woods. There were 10 of us and we all had dirt bikes and would go out riding all the time.. On Saturdays we had a game ... Read full Story
Stephanie101 2024-04-26 4,448 anal Crossdresser Outdoor Blowjob cum in mouth teen (18+)
100%
Sweet Encore
I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... Read full Story
Regina10 2024-05-09 3,619 Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass Ass to Mouth
88%
Always Wanted A Shemale
I always wondered what it would be like to be with a girl with a dick. After spending years on the internet having internet sex, I finally found a black shemale. After hours of talking about how big her cock was and size double D tits, she finally agreed to meet with me for some fun. We met at th... Read full Story
shemale lover 2014-04-15 10,474 shemale black butt fucking
92%
All The Transexual Stories Came To Life
I’ve spent my adolescent years reading the transexual stories whenever I could. I had a long process of self analysis trying to figure out if I were gay or not, so I wanted to find a shemale who could be my first and see if I even like being fucked or sucking a dick. Thanks to the sex personal... Read full Story
shemale lover 2016-02-12 6,206 suck shemale ass licking
81%
Barooms & Motels
Frankie pulled into the first motel he found, it was late and he had been driving all day. After checking in, he went to the room and tossed his suitcase on the desk and flopped on the bed. Frankie was on the road for one reason, he just left his wife of eight years and his kids, a son and a daughte... Read full Story
shemale lover 2012-02-24 4,226 anal cum oral Guy Fucks Shemale
81%
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 7,121 first time shemale Latex pornstar
100%
I've always wanted to meet a gurl!
First of all I would like to apologize for my English. Hello there! I live in a small country's biggest city and here people are strange. If they are crossdressers, shemales, trannies, tgirls, gurls (actually we have only 2 words for a shemale, so I don't know which one is NOT offending please excu... Read full Story
shemale lover 2012-03-30 2,727 Small Tits anal sex oral sex cum swallowing
100%
A Night to Remember
I have always had a strong fetish for stockings, garters, sheer panties, heels and other sexy lingerie. I've always required my women to dress this way for me. Even when I walk through the lingerie section in a department store or Fredrick's and I can't help but want to look at the panties and stock... Read full Story
shemale lover 2012-04-26 4,347 anal Fetish oral fingering domination Sex Toys
100%
Quickie at the Mall Food Court
I was in the food court at the mall just a few blocks from my office. The mall wasn't doing very well since a new, bigger mall and a series of big box stores had been opened at the next exit, and half the stores were closed. The food court itself had lost two more restaurants, and there was a pretty... Read full Story
shemale lover 2012-09-04 4,590 Cumshot Masturbation Big Cock Guy Fucks Shemale condom sex
100%
Dimensional Portals Suck Ass
Marley was dead: to begin with. Hold it… no, no that’s not right. My mind is wandering. What was I gonna write about? MATT! Yeah, Matt was a bastard. And I mean it in the sense that he sucked monkey balls. That’s an expression I like, sucked monkey balls. Anybody ever played blows... Read full Story
shemale lover 2012-09-21 3,239 Creampie oral facial huge tits
100%
Bi male and anal sex
Thru out my adult sex life I have always enjoyed having my ass teased and played with. Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. Then one night things changed. After a hot night of wild sex,... Read full Story
shemale lover 2012-10-10 5,611 anal sex cum jerking fingering
91%
My first BBC fuck
I went clubbing last week with my girlfriends that I work with and they recommended a hip hop club in a seedy part of town. I was alittle scared but we went anyway and well, and we were really having some fun there!!! I decided to dress like a real lil slut this night, a black minidress, lacey thigh... Read full Story
shemale lover 2013-06-06 10,168 hardcore Creampie Big Cock Guy Fucks Shemale Interracial
93%
Loving TS Sex
living in a medium size city 30 years ago, it was necessary to stay into the closet. That way of live is really still the reason why I never outed myself, even after years living in different bigger cities and several countries. I had acquired a taste for transsexuals, considering them the best o... Read full Story
shemale lover 2013-12-08 5,062 tranny sucking Shemale Fucks Guy ass fucking condom sex