Sort by
Relevancy

Free Stories

85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 12,303 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,789 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys 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 5,511 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
78%
Bikini contest
I was at this beach bar in Mt Pleasant SC. There was a bikini contest that day. As I attended, the contest started. I was 23yrs old and the thought never crossed my mind about a tranny. However this was supposed to be all girls. Nobody, including me suspected this girl that won the contest was a tr... Read full Story
jim3801 2017-08-09 19,479 Small Tits Ebony Lingerie Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
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 5,905 tranny Cumshot Shemale Fucks Guy ass fucking Guy Fucks Shemale
80%
Ann and I
Last night I had an awesome experience. I was down in Fort Worth to meet a tranny I had been talking to on squirt. I got off work early, took a shower and shaved my cock and balls and dressed in jeans and a t-shirt and headed down to Club Changes to meet her at four. The bar was pretty empty, Thu... Read full Story
Giantsquid 2017-10-13 14,222 Small Tits Amateur Bareback Guy Fucks Shemale Ass to Mouth cum in mouth
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 5,143 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
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 4,433 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 9,721 Big Tits Blowjob Asian Guy Fucks Shemale
50%
Towel Boi: Heading to Work
“Goddamn, white boi! You got the best fuckin’ ass,” declared the father of two. His steel manly form perspired as he moved hard into the bottom. “Look at all that butt shake! Twerk it for me, baby boi!” “Yes, sir,” cooed Kasey, gyrating rhythmically. “Hell yeah! It’s like fucking two big ol’ ma... Read full Story
Faggyboi and Puzziboi 2023-11-17 6,470 anal Crossdresser Bareback Creampie Blowjob gangbang Lingerie Guy Fucks Shemale Interracial sissy femboy bbc
100%
How A straight tatted white guy turned me out to a femboy
So I met this straight white guy on an app (wont say) hes tatted a bit thuggish and likes black femboys I noticed. At that time in my life I really didnt embrace being femme I was kinda in the middle doing the cute gay twink boy thing. He didnt mind me presenting male he did like black guys or femme... Read full Story
Ezra_Kyle25 2024-07-18 4,864 Crossdresser Amateur Ebony domination Guy Fucks Shemale Interracial big ass Homemade sissy femboy interracial fuck
0%
Brother of the Bride
“What in the ‘Get Out’ hell is going on here,” quizzed the warm, brownish-red woman with the Bantu knots as soon as they were safe inside the gold 1970 Deuce and a Quarter. “I don’t even know,” chuckled the driver as he jerked his head to get his short dreadlocks out of his line of sight. “Wel... Read full Story
Faggyboi and Puzziboi 2023-07-15 5,565 anal Crossdresser Guy Fucks Shemale Interracial sissy femboy faggot sissy crossdresser BB jack of spades bblbuttcd bbl
50%
Fluffy Takes a Walk
It neared dusk at ValueStar Motor Lodge which sat smack dab in the middle of the hood. Inside of Room Twelve, an average height, chubby, brown-skinned femboy repeated the douche. He let out the stream of lukewarm water and turned around to study the toilet as the hip hop music blared in the backgrou... Read full Story
Faggyboi and Puzziboi 2023-04-09 5,584 Crossdresser Big Tits Guy Fucks Shemale big ass sissy femboy BB fagg faggyboi puzziboi
100%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 6,466 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
100%
Towel Boi: Agreement Signed
Ralph moved the mouse to wake up the computer. He navigated to his legal docs account and downloaded a generic pre-existing relationship agreement. He asked for the spelling of the new hire’s first and last name. “First name K-A-S-E-Y. Last name S-T-E-V-E-N-S.” “Got it,” acknowledged the owner. ... Read full Story
Faggyboi and Puzziboi 2023-11-14 6,282 Crossdresser Bareback Creampie Blowjob Guy Fucks Shemale Interracial small cock big ass sissy femboy
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 6,252 anal Crossdresser Ebony Guy Fucks Shemale sissy femboy bbc faggot faggyboi puzziboi
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 3,114 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade 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 11,029 Group Sex Bareback Shemale Fucks Guy threesome Big Cock Ebony Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
100%
Being Shemale Part II
After sometime the driver left. Night Two I was again ready by 10 Pm as usual wearing make up and sexy night outfit. My push up bra helped my breast look very attractive looked perfect with my slim body I was standing as usual in the balcony around 11 PM and the driver stopped by again.... Read full Story
babydriver 2024-06-04 3,822 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy Lingerie domination small cock big ass Frottage sissy femboy
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 3,991 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 3,939 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
81%
Husband and wife used by Mr. Big Black Cock
We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and befo... Read full Story
shemale lover 2011-12-18 8,175 shemales gay male interracial sex
94%
Crossing lines
It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... Read full Story
Zöe from Kingston 2019-02-04 11,434 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,962 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
95%
An itch that finally got scratched
Hey all! New to the site, but have been a major fan of TS/CD etc since I was a teen. I remember always fantasizing about what it would be like if I was to ever get an opportunity to make the fantasy a reality. Well, I finally got that chance and took full advantage of the situation and I wanted ... Read full Story
sizeman 2013-04-10 8,435 Shemale Fucks Guy doggy style Guy Fucks Shemale cum swallowing riding cock
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 23,128 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 13,568 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
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 3,021 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 5,130 anal Amateur Cumshot Bareback Big Cock Ebony Guy Fucks Shemale Interracial black Tgirl
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 5,867 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
100%
Tasting the good FLESH
I am no longer Virgin, en bon et du forme Thing never dared since I taste the enjoyment by all the senses and in all its senses... I discovered her when she smiled at me as a thank-you for giving her the way to the small-town supermarket where I was on business. Sandals at her feet of Cinderell... Read full Story
hippocampus_171 2022-11-10 5,134 Amateur Creampie Shemale Fucks Guy Guy Fucks Shemale Mature Ass to Mouth cum in mouth
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 8,077 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,741 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
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 48,602 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
100%
Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
shemale lover 2012-12-20 9,675 Cumshot sucking blonde ass fucking Guy Fucks Shemale
92%
My wife Gwen
My wife, what can I say she is tall and leggy with thick, natural wavy orange-red hair with beautiful porceline skin and just enough freckles to tell you she is a true ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen. From the time we... Read full Story
Zöe from Kingston 2019-01-08 7,979 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth