Sort by
Relevancy

Free Stories

100%
Crossdressing at CCBC in Palm Springs
I recently stayed at CCBC in Palm Springs. For those of you who are not aware of it, it is the largest gay resort in Palm Springs area. The resort has about 30 rooms, lockers, a pool, steam room and indoor and outdoor play areas all on a one acre outdoor enclave. I arrived there on a Tuesday and dre... Read full Story
Rocky8844 2024-05-27 2,874 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
100%
Bareback fuck by Lysa Shemale
Well I am devoted shemale lover and have met many shemales in my life. This incident is of probably December. I called my shemale escort Amy to meet and some how she was not picking call. Then around 4.30 pm she picked n told me that she is having hangover due to party so was sleeping, so I sh... Read full Story
Stud4Shemale 2021-02-20 7,207 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob cum in mouth barebackedshemales shemale fucks male cum in ass Indian Shemale Pune
86%
Alex’s Bottom Slut
So when I was younger, I worked at a pizza place as a delivery guy. It was a pretty boring job for the most part but that all changed one night. I got a delivery to just outside of our range but decided to take it anyways because we were slow. When I got there a very tall and muscular black woman in... Read full Story
Jsmithsub 2019-11-18 56,552 Group Sex Cumshot Shemale Fucks Guy Blowjob Big Cock Ebony gangbang domination Interracial Ass to Mouth cum in mouth
94%
My Shemale Fantasy
Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... Read full Story
Jakester 2013-04-10 31,674 first time Creampie Shemale Fucks Guy ass licking virgin
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 22,157 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
91%
MY FIRST TIME WITH A SHEMALE
I`ve always had this fantasy about being with a shemale,i guess something about a chick wit a dick and tits always turned me on,i`ve always been curious about wat it`s like to be fucked by one.Well last weekend was a weekend i`m gonna remember for the rest of my life bc that was the weekend i decide... Read full Story
shemale lover 2013-06-21 15,011 tranny Cumshot Shemale Fucks Guy Big Cock fingering swallowing
83%
My Start
In the beginning, when I was younger and trying out my sexuality and starting to understand what I wanted and liked and craved and needed, I played with boys and girls. But in short order, I decided I wanted something in between. Which is how I would find myself sneaking into clubs in Manhattan in t... Read full Story
Giantsquid 2019-01-14 9,014 Stockings Teen (18+) Small Tits Crossdresser Group Sex Bareback Blowjob Lingerie cum in mouth
100%
New Orleans TS dream come true..
In was on New Orleans running water for the victims of Katrina in 2005. I went down to Bourbon St several times an one night I walked into adult fetish store and as I was looking around there was what appeared to be a very beautiful black woman bending over with a very short skirt on. I was admirin... Read full Story
jim3801 2018-09-11 10,628 Group Sex Bareback Shemale Fucks Guy threesome Big Cock Ebony Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
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 9,453 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
89%
Fulfilling fantasies
What seems like a long time ago in my early teenage years, I found myself being somewhat addicted to watching porn. Every opportunity I got I was at the computer watching porn of all different flavours, and for a while I found myself really enjoying lesbian porn. So one day as I was watching a video... Read full Story
curiosity12 2015-06-30 7,339 anal first time tranny Cumshot Shemale Fucks Guy
100%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 6,083 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
92%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 8,734 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
50%
I kneel in front of Dominatrix Persephone
Fan Mail. I kneel in front of Persephone.. She looks amazing in Her latex catsuit, but there is something else eye catching. Chance, Persephone huge hó rse c... It looks intimidating in picture, but just think how it must look when it is right in front of your face!! Holding it in my sissy hands, i... Read full Story
Dominatrix Persephone 2024-06-18 2,799 anal Stockings Cumshot Shemale Fucks Guy Fetish Big Cock redhead domination Interracial Mature Homemade sissy femboy teen (18+)
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 4,312 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 95,872 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 10,445 Shemale Fucks Guy Ladyboy Mature
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,150 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
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 5,497 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
80%
Group Sex
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 2021-04-19 3,175 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale cum in mouth
75%
So good fuck with me and my klients.
Hello, I am Francesca, and I offer company to couples and women. A few days ago, a couple hired me for two hours.The woman was fucking me with her strapon while I was stroking the man's cock. She was pushing her hard cock deeper and inside me, I could feel my ass dissolving more and more. I turn my ... Read full Story
Francheskahotass 2021-08-11 3,331 Crossdresser Amateur Group Sex Cumshot Shemale Fucks Guy threesome Ladyboy Lingerie Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
100%
badbadboi's walk in the park
...My boi hole was freshly washed, shaved and lubed with a lovely hot shower, my wand is perfect for cleaning my pussy, flushing it clean very time, I luv to let the water spray my hole driving deep enough to tickle the bottom of my prostate. My cock cage locked in place, my white crotchless panties... Read full Story
badbadboi667 2021-04-06 3,638 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Interracial Homemade Ass to Mouth cum in mouth
100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 7,407 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
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 9,577 hardcore Cumshot Shemale Fucks Guy ass fucking handjob
87%
Encounter with a dominant shemale
One night I was feeling really horny. I just came back from the gym and I wanted to release and relax. I then began my search for some fun on the personal ads section. I have always been into shemales especially verse aggressive ones. I found this one particular post about Asian bottoms. I was c... Read full Story
SecretAznMan 2013-06-28 47,950 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
96%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-11-25 10,051 tranny suck Creampie Shemale Fucks Guy ass fucking 69
80%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2014-12-03 6,377 tranny suck Creampie Shemale Fucks Guy ass fucking 69
100%
"The Arrival" The silly little sluts first Freedom of touch
Based upon Khloe Kay, my imagining if I could be her. { Unedited} a habit to arouse my deepest desires. -Araina Sinclair, Sissy Slut to be. Hope you enjoy. He started to pound my ass, quicker and quicker. Deep long strokes. My boi pussy stretched he started to pull out and slap his head . In... Read full Story
Araina 2021-02-15 2,020 anal Cumshot Shemale Fucks Guy Fetish Blowjob cum Lingerie slut sissy femboy handsfree Khloe Kay
89%
My first shemale experience
So before I was even into the porn I had my first experience. I was 25 years old and never thought about anything like this till it happened. I was out with my friends one night hitting the usual bars on the weekend when this hot young woman caught my eye. I was feeling pretty brave due to my "... Read full Story
Duke04 2017-03-28 53,164 first time Amateur Cumshot Shemale Fucks Guy hot shemale
85%
Alternative Plans
Another Goth Trans Girl Confession I really enjoyed my first sexual experience. I had gone to the local adult entrainment store and purchased some toys; a butt plug, a 10inch purple dildo, some lube and condoms. I would occasionally play with my toys while watching some internet porn. I loved ro... Read full Story
Gothtransgirl41 2017-11-10 11,211 domination cum in mouth quickie
100%
Liberty in Lisbon Part 2
So here I was walking down the Av da Liberdade feeling very pleased with myself. I had just thoroughly enjoyed an experience I thought would only ever be in my dreams and, the best part, there was more to come [cum]. In fact I found myself humming the 59th Street Bridge Song. Life I love you feeling... Read full Story
Rusty12 2019-07-31 4,919 Amateur Masturbation Bareback Creampie Shemale Fucks Guy cumming
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 5,131 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
one of those stories i wish i was in.
Tim stepped into his new college dorm room and breathed in the possibilities. The sun illuminated the simple tile floor and the simple room furnishings. Freshly cleaned desks and wardrobes neatly lined the walls. The beds had thin blue mats and pencil graffiti etched into the legs. He noticed that t... Read full Story
TylerTheLovely 2018-03-02 6,434 Shemale Fucks Guy
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 32,597 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
81%
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 3,891 anal Crossdresser Outdoor Blowjob cum in mouth teen (18+)
100%
Ill take all the cum I can get
I'm so horny today. I need some dick bad. So I dress up, I put on a sexy push up bra, a slutty lace top, a naughty little g string, and lacy thigh highs with a garter belt. Before getting dressed I showered and gave myself an enema. After I showered, I used some fds so I smelled sooo good after ... Read full Story
spreadforalldik 2024-07-09 859 anal Crossdresser Group Sex Cumshot Creampie Blowjob ass fucking Ass to Mouth cum in mouth spitroast
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 5,640 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale