Sort by
Relevancy

Free Stories

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 14,674 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
80%
Buffy the Shemale Vampire Slayer Part 13
Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... Read full Story
shemale lover 2011-08-23 4,145 Masturbation pussy shemale
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 9,325 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
100%
Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
shemale lover 2012-02-06 5,696 sucking shemale massage
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 5,964 anal sex sucking shemale
100%
T-Girl Rodeo
Howdy folks, we would like to welcome y'all to the finals for the 10th Annual T-girl Rodeo! Now this here being the tenth anniversary and all we're gonna put on one hellva show for ya! Commentating up here in the announcers box with me is the first ever T-girl Grand Champion, Lorna "Tail Buster... Read full Story
shemale lover 2012-09-05 5,595 Masturbation shemale and shemale Big Cock condom sex ass fuck
88%
Oh My, You Have a Cock...
It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come t... Read full Story
shemale lover 2013-08-09 33,416 anal sex Cumshot Shemale Fucks Guy redhead
92%
A Shemale and Her Unexpected Friend and Me
There I was on the boardwalk waiting for texts back from trannies from craigslist. As I sat staring at the ocean, I yearned for some sexy shemales to get back to me. I started walking around the boardwalk more, anxiously, desperately. All the sudden, a beautiful older woman was walking by with her d... Read full Story
tysonsbakery 2015-11-16 7,257 tranny ass shemale domination double anal
78%
First Time Having Sex With A Shemale
Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... Read full Story
bigtranslover 2011-05-21 15,674 first time shemales interracial sex
82%
My shemale weekend
I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting... Read full Story
shemale lover 2015-09-05 9,942 shemales Group Sex interracial sex
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 8,955 Big Tits Cumshot Masturbation Uniform Frottage
100%
I was Teen Shemale for the US Army
Chapter 1 Reform School Romance! I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II. I mean I thought we got along pretty darn good, and its not like he had any money or anyth... Read full Story
shemale lover 2012-10-22 4,680 shemales gay male Interracial
77%
New Girl Chapter 2
Olivia's hands shook as she read the note, a look of stunned disbelief on her face. She had to hold on to the bar for fear of falling over. The note shook her to her core. 'Olivia, Tim agreed to leave with me. I am in the process of moving. Please come to my new address in two months time, at 7 ... Read full Story
shemale lover 2012-12-22 3,695 Crossdresser shemale cd heels
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 12,779 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
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 8,154 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 7,204 Creampie Big Cock ass fucking
100%
My Fantasy Story
My first time, Sissy Cuckold for BBC After ten years of marriage, my wife and I wanted more. First we went to some strip clubs together. One night one of the girls my wife liked told us about a swingers club. So we gave it a try. Best decision we'd ever made. We went, at first just wallflowers, ... Read full Story
Mikky666 2020-10-09 10,702 blonde Big Cock Interracial Ass to Mouth
80%
Chapter 2 - Cuckold Cruise
If you read Chapter 1, you know how I’ve been a weak, submissive sissy my whole life. My tiny nub of a penis never fully developed has never been inside a woman. I was fortunate enough to find and marry a strong and beautiful woman who accepted my submissive nature but only learned the full scope ... Read full Story
Sissy Annabelle 2022-10-07 6,030 Interracial crossdressing sissy cuckold chastity
100%
Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... Read full Story
shemale lover 2012-04-22 6,633 anal sex Creampie blonde shemale
94%
Penitentiary Pussy-Butt Boy
Hi: My name is Bobbie. Would you like me to tell you how I became a Penitentiary Pussy-Butt-Boy? Well, it all started with a robbery gone wrong. I wasn’t even in the bank when the guard got shot and I still got almost as much time as the others. So, not long after the trial I was sent to the sta... Read full Story
NaughtyBobbie 2014-04-11 15,599 hardcore suck Big Cock Interracial crossdressing
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 5,364 Crossdresser Amateur Ebony domination Guy Fucks Shemale Interracial big ass Homemade sissy femboy interracial fuck
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 35,075 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 32,105 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 6,205 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
50%
EROTIC FANTASY PART 1.
The Secret Manor of Lusting Intersexual Ts.Ladys as they enforce males into there training house all too become wimpering shemale sexslaves! I met a Lady once at Bar too which she was very sexy Lady as we had some fun now n then as too get too know each other I slowly tranformed myself into her E... Read full Story
Isabella Coupe 2024-09-25 1,951 Amateur Fetish Uniform domination
94%
Fem Firm: Character Intro
Coxson & Dicster is a law firm made up of nothing but she males They are: Debra Coxson- 37 Debra has been a lawyer for 12 years and started the firm with her college roommate Angela Dicster 5 years ago. She's a leggy ash blond with 38D tits a great ass and a 9 inch cock. She loves to ... Read full Story
bennyx709 2015-07-29 5,774 Cumshot suck shemale oral
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 12,533 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,534 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
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 4,906 shemale oral orgasm
91%
Banana Fetish
I was 27 and single and enjoying being free sort of the ‘sworn to fun loyal to non’ stage in young adulthood. I lived alone in a 1-bedroom apartment and loved working on my motorcycle which I kept in my living room. Most Friday nights for me were jamming out to music, enjoying a few beers and tinker... Read full Story
AllenB 2023-02-16 10,470 Latina Fetish Big Cock Guy Fucks Shemale Interracial rimming Homemade Ass to Mouth Banana ass eating
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 4,592 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
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 9,558 Crossdresser Amateur Cumshot Latina Bareback Creampie Shemale Fucks Guy Fetish Blowjob Interracial Homemade cum in mouth
100%
I Fooled Everyone But the Black Pimp Part 1
So I’m sitting at the pub drinking with the guys and talking sports and pussy. I’m wearing work boots, jeans and a white T shirt. I’m also wearing purple panties and a butt plug wishing I was getting spit roasted by big cocks. I'm very restless on my bar stool as I grind my hungry hole down ... Read full Story
cdtampa4u 2023-05-04 5,946 Crossdresser Interracial black cock sissy Pnp Closet Sissy
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 5,005 shemale cum ass fucking
90%
A Schoolgirl Fantasy
As I sat on the couch watching some boring show, I was thinking, "Being alone doesn't have good perks. Maybe if I wanted to dream something naughty, it might be cool." So, I closed my eyes, and I dreamed of a very naughty transexual schoolgirl who would do what I needed. All of a sudden, I heard a s... Read full Story
OldHungDude67 2019-03-04 5,997 Amateur Cumshot Blowjob Uniform Guy Fucks Shemale Homemade Ass to Mouth
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,737 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth