Sort by
Relevancy

Free Stories

100%
Club sex the 25yo
There’s a very special private club around, it’d meetings take place in a very secret place. It takes a lot to gain membership. You have to either have a lot of money AND a friend in the club OR you have to take part in the ceremonies for at least a year. Also you have to be willing to b... Read full Story
shemale lover 2011-12-10 4,954 anal Group Sex lesbian
100%
The Triple X cocktail - Wife Shares Shemale With H
"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an ... Read full Story
shemale lover 2012-02-21 3,630 Group Sex Creampie face fucking tit licking
100%
1st time with Thai shemale
So after months of crosssdressing , camming and phone sex i finally decided to have a meet. I found a lovely Thai shemale on birchplace and went to see her in London. She was gorgeous and put me at ease straight away. After a few minutes of massage she started licking and sucking my nipples, then as... Read full Story
Nutcracker29 2013-04-09 9,251 first time suck Shemale Fucks Guy Asian 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 10,056 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 6,379 tranny suck Creampie Shemale Fucks Guy ass fucking 69
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
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,589 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,094 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
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 4,325 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 11,846 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
87%
Southern Hospitality Ch. 03
XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... Read full Story
Gwapo67 2022-05-16 4,768 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
92%
Southern Hospitality Ch. 04
XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... Read full Story
Gwapo67 2022-05-16 6,722 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature 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 4,333 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
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 2012-12-21 118,743 hardcore Cumshot sucking bdsm domination
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 5,135 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
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 5,829 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
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 12,166 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
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 5,290 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
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 3,191 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
0%
Lady Denisa's Gang Banged
The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... Read full Story
shemale lover 2011-11-22 4,439 shemale oral orgasm
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 5,752 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,253 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
50%
A Married Marilyn
"Class is dismissed. Don't forget the project due…" "Huh, what?" Marilyn woke up disoriented from her nap. When she finally came to, she vaguely remembered some project for Intro to Computer Science, gathered her legs from the chairs in front of her, dusted off her b... Read full Story
shemale lover 2012-03-18 7,165 Group Sex Masturbation sucking Sex Toys
100%
Chinese Apple Turnover
I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax f... Read full Story
ASSEaster5678 2019-01-09 6,567 anal sex Shemale Fucks Guy Asian Guy Fucks Shemale
94%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 7,085 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
100%
Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
Gwapo67 2022-07-22 5,845 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
The Day I Went SheCock Crazy
I summed up courage to meet up with my old shemale flame Fransicca (she is a Malaysian but living in indonesia) ... messaged her, she sounded excited and asked if i minded her friend joining us. 'Why not' i said. It was settled. we booked a villa for the next day. I checked in early. cleaned up ... Read full Story
Sara Banks 2021-04-26 6,568 Group Sex Cumshot Outdoor Bareback Shemale Fucks Guy Fetish Blowjob blonde Big Cock Asian Ladyboy gangbang
92%
My Dream pt 3
Our first invitation arrived at the end of September. Sydney spotted it first and tossed it into the trash with out looking at it. She didn't tell me what it was and I didn't bother asking. The next invitation arrived two weeks later. This one Sydney opened and after reading it she passed ... Read full Story
Sydney Sun Min 2018-01-04 16,510 Group Sex Shemale Fucks Guy Shemale and Girl Sex Toys
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 33,777 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
darrell 2022-01-03 4,626 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
100%
TG girlfriend is my new 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 2022-01-17 4,123 Big Tits Bareback Creampie Shemale Fucks Guy Big Cock Asian Guy Fucks Shemale
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 6,540 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
100%
My first TG lover
I first met Holli at the gymnasium of our apartment complex. Since it was around 6:00 am on a Sunday morning, I didn’t expect to see anyone that early. At first just like we all do, the customary good morning, small talk, and it usually stops there, but there was just something that drew my attentio... Read full Story
Jon Paul 2022-07-01 7,675 Amateur Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale
91%
Lake Surprise
After finals of my first year in college in a northern university, I was ready for some real relaxation back home in the warm south. During finals I had started thinking how nice it would be to borrow my brothers boat and hit the lake for a week. I talked my roommate into making the trip home ... Read full Story
shemale lover 2011-12-08 10,660 anal Group Sex Creampie
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,001 big dick anal sex suck Blowjob cock sucking workplace
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,457 Big Tits Cumshot Masturbation Uniform Frottage
80%
Transsexual Savage
John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... Read full Story
Anal Orgasm 2020-07-10 6,275 Big Tits Outdoor Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Guy Fucks Shemale
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 5,141 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,314 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,279 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
100%
The Three of Us
Imagine you are a lonely person on the inside, and just wanting all your life to be loved for who you are. Holli Artigas, was just that person. Wondering whether her obsession with Jon Silva, a football star, was from a casual encounter, or was she truly fond of him? Growing up in the Sao Paulo, ... Read full Story
Jon Paul 2024-04-28 3,177 anal Creampie Shemale Fucks Guy threesome Shemale and Girl cum in mouth double anal shemale fucks female
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,803 Masturbation cum orgasm cumshots prostate
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 4,929 sucking fingering Guy Fucks Shemale
66%
Would You
'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her sk... Read full Story
shemale lover 2012-09-23 6,557 sucking cum massage
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,292 Crossdresser sucking Big Cock ass licking big boobs
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 10,949 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
50%
The Visit
A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... Read full Story
shemale lover 2012-01-26 8,296 Group Sex licking sucking pissing fucking
100%
Additional Thoughts on Sodomy
Although, in the world (or worlds?) of pornography and erotica, it is politically incorrect, perhaps, to suggest that the body, whether male or female, is not built for anal intercourse, the fact is that anyone who has participated in this act (especially on the receiving end) or who has enjoyed wat... Read full Story
shemale lover 2011-10-05 3,988 Creampie sperm anus
100%
Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
shemale lover 2012-05-26 4,319 anal sex Creampie Blowjob crossdressing
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,882 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
57%
Transsexual Actresses Part 1
The adult entertainment market includes thousands of videos and DVD's featuring transsexual actresses. Some of the more popular of these celebrities have their own web pages. Brief profiles of some of these actresses, including a list of their films, appears after the initial list. Adriana Ventur... Read full Story
shemale lover 2011-09-08 9,243 shemale transsexual porn star
75%
Rebound
My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to... Read full Story
shemale lover 2011-11-25 6,218 anal Creampie oral
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,373 Big Tits sucking ass licking fucking
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 4,797 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
83%
Milking Time Jordan's Arrival
These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... Read full Story
gman57 2019-09-25 10,598 Big Tits Big Cock shemale + shemale
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,224 cum massage shemale sex