Sort by
Relevancy

Free Stories

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 13,017 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
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 11,793 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
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 14,041 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
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 5,068 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
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 7,551 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
94%
Flight cancelled
I was on my way back from a long business trip to Chattanooga, Tennessee and deciding to hit the airport bar during my layover. As I walked up to the bar I noticed there was only one seat open. I took it. I ordered my favorite drink, an old fashioned neat with makers mark. As I sat there waiting for... Read full Story
Jsmithsub 2019-10-31 24,288 big dick Group Sex Bareback Shemale Fucks Guy Fetish Blowjob Big Cock pissing Ebony domination cum in mouth monster cock gang bang
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 10,571 Group Sex Bareback Shemale Fucks Guy threesome Big Cock Ebony Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
80%
Boy Meets Girl
"What's her sister look like?" Dave Newell asked his brother. "You've seen Steph. They're sisters." Stephanie Johnson was a hottie, no doubt about that, Dave thought. Still, that didn't necessarily mean that her sister would be a looker. If Stephanie were from Venus, her si... Read full Story
shemale lover 2011-11-05 5,205 asshole oral sex tgirl
100%
Big Surpise In Small Package
It was a Friday night and I was extremely horny and just my luck my girlfriend was out of town, but I wasn't horny for her I was craving cock. I knew I was bi for a long time and loved to have a nice hard cock to play with every once in awhile. So I decide to call my girlfriend to tell her I was goi... Read full Story
shemale lover 2012-06-11 4,257 anal Group Sex Cumshot Blowjob
100%
College project surprise
So this story happened while I was still in college and remains without doubt, the craziest, most exciting experience of my life. So I the story begins one day when I walking to class. I went to a big university so my walk was quite long, and the first 1/3 was just through off our campus housin... Read full Story
Jsmithsub 2020-09-16 20,921 Group Sex Bareback Shemale Fucks Guy Fetish threesome Big Cock Ebony domination Ass to Mouth cum in mouth
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,635 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
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 56,451 Group Sex Cumshot Shemale Fucks Guy Blowjob Big Cock Ebony gangbang domination Interracial Ass to Mouth 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 4,285 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 6,677 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
100%
Random Thoughts on Tits
Tits. You have to love them! They bounce. They hang. They jiggle. They sway. They tremble. They wiggle. If you're a man (or a lesbian with a strap-on strapped on), you can even fuck them. They can be bound with cords so that, the blood flow to and from them restricted, they turn purple. Clothespins ... Read full Story
shemale lover 2011-11-17 2,647 shemales tits transsexuals
100%
Lady and the Cop continued
The next night Regina got a visit from. Larry the cop who openly declared war on shemales and trannies. He was working a homicide where a trannie friend had been killed in her apartment. Larry was a known shemale hater and he never failed to express his opinions. Tonight he was in her apartment to ... Read full Story
Regina10 2018-03-06 4,627 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Oneness with the bodies
many years went into just fantasizing being with shemales. I was getting hornier day by day to try it out. But being in a relationship there was hardly any room or time for it. I once experienced it in bangkok and confirmed that I really can do it and actually love it. One day suddenly it was br... Read full Story
zyankhaan786 2023-05-30 6,380 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
87%
First Time - Surprise Shemale
I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so ... Read full Story
shemale lover 2014-09-19 19,364 first time tranny Shemale Fucks Guy jerking wanking 69
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 9,997 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 6,331 tranny suck Creampie Shemale Fucks Guy ass fucking 69
38%
A date to the sex shop
So last night I decided to meet up with a young shemale in Portland, now this is my first time ever with a trans and I was so nervous and excited all at the same time my face kept doing this weird little twitch. So we hang out for a little before we decide to go to one of those classic dirty sex sho... Read full Story
Quin Sharp 2017-05-31 5,414 anal Teen (18+) Bareback Creampie Shemale Fucks Guy prostate orgasm
78%
A Little Girl Forever
Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... Read full Story
Mabel Cecilia 2019-05-06 7,968 Small Tits Crossdresser Amateur Cumshot Latina Masturbation Creampie Blowjob blonde Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys Mature self sucking Solo Shemale cum in mouth double anal shemale + shemale
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 3,011 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
50%
MON SECRET RÉVÉLÉ ⚧️ ⚧️
C'etait ma propre faute. Comment ai-je pu être si stupide ? Je m'appelle Karl. J'ai démarré une entreprise Internet il y a douze ans. J'avais travaillé comme représentant d'un fabricant pour une maison de courtage spécialisée dans les marchandises importées. Je pensais que mon entreprise ne faisa... Read full Story
Femboy 2021 2023-03-30 895 Group Sex Creampie Big Cock Lingerie Guy Fucks Shemale cum in mouth feminisation forcé cage de chateté domination fémi
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 5,213 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
92%
A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
shemale lover 2014-05-21 18,498 shemale fingering cumming
50%
The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
shemale lover 2011-10-18 4,619 Group Sex Masturbation shemale oral
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 4,904 anal Group Sex lesbian
92%
T-Girl Meets T-Girl
It was a silent car ride home. He looked at her, she looked out the window. She looked at him, his eyes were on the road. Neither of them broke the silence. It stayed that way until he parked in her mom's driveway. The soft-spoken young man told his girlfriend, "Goodnight Ashley. I'll call y... Read full Story
shemale lover 2012-08-29 6,123 anal sex Cumshot shemale and shemale domination blondie
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 12,790 Group Sex Cumshot shemale oral
82%
Halloween Double Cross
It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeou... Read full Story
ASSEaster5678 2018-10-29 11,237 Shemale Fucks Guy sissy Halloween
100%
The Girl Next Door Ch. 03 by derezzed ©
Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... Read full Story
StevelovesTgirls 2019-06-11 18,526 Amateur Shemale Fucks Guy Fetish threesome Blowjob domination Guy Fucks Shemale Ass to 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 3,134 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale cum in mouth
94%
My first shemale
This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when... Read full Story
shemale lover 2012-02-12 13,206 first time Creampie Shemale Fucks Guy
88%
MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
shemale lover 2013-12-01 39,940 first time anal sex suck Shemale Fucks Guy Guy Fucks Shemale
88%
Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
ASSEaster5678 2018-07-10 10,708 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
50%
Angel The Shemale Vampire
Angel stood in the shadows watching hungrily as the group of laughing young college kids came toward her down the alley. The group was made up of four guys and a girl. The girl was hanging all over one of the guys and it screamed how badly she wanted to get in his pants. Angel's smile broadened with... Read full Story
ASSEaster5678 2018-10-29 7,362 Group Sex shemale vampire
50%
Pa-mie sex-agénaire
Luxure frénétique d’une pa-mie sex-agénaire; entre rêve et réalité Je n’avais jamais fantasmé de mec viril, même après avoir offert ma virginité; mais à une fabuleuse sissy. Avant mon Ѐre, mes préférences de fantasmes étaient toujours avec des lui-femme glabres, idem concernant mes relations d’aprè... Read full Story
hippocampus_171 2023-07-09 807 anal Amateur Group Sex Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy Ass to Mouth
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 3,585 Group Sex Creampie face fucking tit licking
100%
Fulfilling A Girl's Male Fantasy Part 2
Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a ... Read full Story
shemale lover 2012-04-04 4,334 Stockings anal sex Group Sex Blowjob
90%
My first shemale sex
I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... Read full Story
shemale lover 2013-08-14 94,387 tranny sex toy anal sex suck Shemale Fucks Guy dildo
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 4,810 tranny sucking Shemale Fucks Guy ass fucking condom sex
100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 7,849 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
91%
The Girl Next Door Ch. 03
derezzed Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Ale... Read full Story
Gwapo67 2022-05-13 5,934 Bareback Creampie Shemale Fucks Guy threesome Blowjob cum in mouth
100%
by a Shemale Part 2
I was awaken early Monday morning when Felicia lightly kissed me on the cheeks and said it was time to start my hormone regimen. I looked at her and she had her left hand opened and she had a white pill and in her right hand a glass of water. I was no longer fighting or resisting especiall... Read full Story
shemale lover 2011-08-29 5,975 anal sex sucking shemale
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,406 anal sex sucking shemale
0%
Mike and Chris Together
Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately. "I'm really sorry, Mike. I've had some great times with you, and I will alw... Read full Story
shemale lover 2012-02-07 5,130 anal sex Creampie Shemale Fucks Guy Guy Fucks Shemale
100%
Shemale snapped
Camilla took a few steps out the door of her balcony to get a feel for the temperature. Thankfully it was cool out. It had been a hot day, which meant a cool night was welcomed. She closed the door and pulled out a pair of gold hoop earrings. She was suffering from a mild case of the jitters. The... Read full Story
shemale lover 2012-06-21 6,177 anal sex Creampie shemale Big Cock
78%
Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
Duke04 2017-04-01 10,368 anal sex Shemale Fucks Guy ass fucking Shemale on Guy
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 10,385 Shemale Fucks Guy Ladyboy Mature
100%
Fooled Into Love by a Beautiful Transexual
A fictional, steamy love story about a Man’s first experience with a Shemale... a real take charge kinda girl! Maria Lopez was an absolutely stunning 23 yr old Puerto Rican Goddess. I remember the first time I laid eyes on her, bent over inside her hatchback Toyota, pulling out a hanging fern pla... Read full Story
Oobatz 2018-07-24 12,579 Small Tits Amateur Cumshot Bareback Shemale Fucks Guy Big Cock domination cum in mouth
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 32,522 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
100%
My first time having sex with a Tranny
I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... Read full Story
Joe22lovests 2021-09-15 11,770 first time Shemale Fucks Guy Blowjob Big Cock
100%
Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
darrell 2024-02-02 5,363 Shemale Fucks Guy Blowjob blonde Big Cock Mature deepthroat cum in mouth toe sucking Fisting Anal
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 9,185 first time suck Shemale Fucks Guy Asian big boobs
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 2,456 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth