Sort by
Relevancy

Free Stories

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 33,062 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
100%
The Golf Bet
A couple of years ago I joined a new golf course, I wasn't the best golfer but very keen, I would be at the practice area almost everyday for at least an hour. Over this time I got to know a number of members and it was a good way of meeting people to play with. Over that year I met a number of new... Read full Story
chris1989r 2022-01-03 5,013 Amateur Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth
25%
Fantastic threesome w/ Miranda Pinocchio & Danielle Albuquerque
Today taken by the craving for something really big I call Miranda who answers me immediately and despite the language barriers and her way of speaking not always understandable we agree for 70 and a quiet thing. I sling in Naples, central area, the usual low in the alleys between via Marina and the... Read full Story
RonWisley 2020-05-04 4,933 Amateur Cumshot Shemale Fucks Guy threesome Blowjob Big Cock
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 5,485 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,379 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
91%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 13,752 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 5,425 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
2 Faker, Eierlose, Blockierlistenuser und ein paar richtig geile
Freitags sind Fimia und ich an die Bi-Night im CW Volketswil gefahren. Als wir eintrafen, waren schon viele Freund:innen auf der Terrasse anwesend. Wir fläzten uns zu ihnen auf die Liegen und schon bald wurden allerlei Zärtlichkeiten ausgetauscht. Da wurde gefummelt, hier wurde geblasen und sogar da... Read full Story
Cheryl_F 2024-09-02 268 anal Cumshot Outdoor Bareback Creampie Fetish Blowjob Big Cock Lingerie Shemale and Girl shemale fucks shemale cum in mouth shemale fucks female
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 14,371 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
ATTENTES SUBVERTIES ⚧️ ⚧️
Les choses allaient si bien.... Après un long et misérable quart de travail, Steven rentrait enfin chez lui. La plupart des gens détestent faire la navette, mais Steven trouve que la demi-heure de route est un moyen idéal pour se détendre avec un livre audio ou un podcast. Dernièrement, cette pet... Read full Story
Femboy 2021 2023-02-17 1,308 Cumshot Shemale Fucks Guy Fetish Blowjob Big Cock Futanari cum in mouth
60%
Shemale Chrissy Fucked by a Demon
I wanted to write this the night it happened, Halloween, but I was still so traumatized. I was at my fictional fantasy Sugar Daddy's house alone and already spooked out by the noises of this old hundred-year-old wooden house in this loud thunder storm on what some call "Devil's Night." I had to turn... Read full Story
Chrissy Tunnell 2022-12-01 4,390 Small Tits Crossdresser Amateur Bareback Fetish Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,461 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
Shemale fantasy with female squirting
I just finished my mornig coffee at the breakfast bar in the kitchen when the door beel rung. My wife opened the doo and it was one of her hot friends. She invited her to sit at the bar beside me and serve her a coffee. Right before she gives her the coffe she slips something into the brew. Her ... Read full Story
TRTRAIN 2023-05-21 3,840 anal Stockings Amateur Big Tits Big Cock Lingerie Shemale and Girl pantyhose Mature Homemade Ass to Mouth cum in mouth shemale fucks female
50%
Dame et jardinier
Piotr se tenait sur les escaliers de la villa de Klonowa Street, située dans le quartier à la mode et riche de sa ville. Il était environ midi par un chaud samedi de juin. C'était son dernier arrêt ce jour-là. Il avait déjà collecté l'argent des autres clients avec lesquels il traitait des jardins, ... Read full Story
Femboy 2021 2023-01-24 1,126 Stockings Crossdresser Cumshot Shemale Fucks Guy Fetish Blowjob Guy Fucks Shemale
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 9,443 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
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 4,704 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 3,899 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
87%
Chicago TG Romance (part 2)
As you must read part one of this story, one of the most interesting and attractive T-girls I have met is sleeping beside me in my motel room after a wonderful evening of being together. Beth awakened around 4am and got up to go to the bathroom. She was brushing her teeth and heard me stirring, I di... Read full Story
Jon Paul 2018-06-04 6,223 Amateur Shemale Fucks Guy Blowjob Asian Ladyboy Ass to Mouth cum in mouth
93%
First Time I tasted Tgirl Sperm
I met a Mexican Trans girl online from Hermosillo and we hit it off and corresponded for a a few months. The vibe was good and ended up deciding that I would help her pay the $140 bucks for her 6-month tourist visa to come up and visit..the process took forever but once she got it, I booked her a pl... Read full Story
AllenB 2022-08-09 9,236 Crossdresser Amateur Cumshot Latina Bareback Creampie Shemale Fucks Guy Fetish Blowjob Interracial Homemade cum in mouth
100%
Bi-Night 18.09.24
Wieder war die Bi-Night im Cruisingworld Volketswil angesagt. Da Fimia und Andrea in Mykonos im Urlaub sind, habe ich mich allein auf den Weg gemacht und bin so gegen 16 Uhr eingetroffen. Eine nette Begrüssung am Clubeingang und schon ging es in die Garderobe. In der Garderobe sprach mich auch glei... Read full Story
Cheryl_F 2024-09-02 312 anal Amateur Creampie Fetish Blowjob Ladyboy gangbang Shemale and Girl sissy pov shemale fucks shemale shemale + shemale shemale fucks female
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,682 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to 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 3,943 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 3,730 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 3,018 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,363 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,566 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
100%
My Sugar Daddy Spanked Me & My Girlfriend (I screwed up again)
In my last fantasy article I explained how my Sugar Daddy allows me to date girls since I am bisexual and attracted to them too, but they, and in fact anyone, are not allowed to touch me intimately without explicit permission from my Daddy. Anytime a girl wants to touch me: kiss, hold hands, put her... Read full Story
Chrissy Tunnell 2022-04-12 2,472 Crossdresser Amateur Big Tits Shemale Fucks Guy Fetish threesome Blowjob Big Cock Ladyboy Shemale and Girl Guy Fucks Shemale cum in mouth
100%
La Mujer Trans más feliz del mundo.
- Porfavor, no pares Gaby! - Le gritaba yo, completamente llena de placer, mientras a 4 patas aguantaba sus grandes embestidas, a la par que mis grandes tetas chocaban entre sí. - Ya casi me voy a venir Juanita! - Dijo ella, mientras trás de mi daba todo de si para hacerme sentir en el paraiso, s... Read full Story
DaphneYuki 2023-10-28 2,311 anal Amateur Big Tits Latina Bareback Creampie Blowjob Big Cock Interracial shemale fucks shemale doggystyle story line
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 2,757 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
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 4,813 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,787 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 34,576 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
88%
Alex and Jon
Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... Read full Story
Jon Paul 2022-09-21 5,615 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
100%
Dating my Sissy-sister (English)
You are wearing women's stockings and a thigh-high transparent top, the thin shoulder straps of which leave your arms and shoulders elegantly exposed! You're the real lil bunny to me in that girl outfit of yours... How about, should I teach the little one about the naughty girl? You're giggling a... Read full Story
LulaSissy 2024-09-24 2,924 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female fucking sissy
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 4,170 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 119,623 hardcore Cumshot sucking bdsm domination