Sort by
Relevancy

Free Stories

88%
Making love on the beach
= First = My name is Lely Bella Calistia, I'm an Asian shemale, I'm 27 years old, and I now live on a very beautiful island in Southeast Asia, I have only been here for 2 years and have a nice new life. I have a friend when I was a child, and we are good friends until now, but unfortunately wh... Read full Story
Bella Calis 2018-10-22 6,169 Blowjob Asian gangbang Guy Fucks 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 3,181 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale cum in mouth
100%
The four of us
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 2021-08-02 4,195 Group Sex Big Tits Cumshot Bareback Creampie Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
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 4,124 Big Tits Bareback Creampie Shemale Fucks Guy Big Cock Asian Guy Fucks Shemale
100%
UN RENDEZ-VOUS ROMANTIQUE ⚧️⚧️⚧️
Alex mordilla sa lèvre en fixant le test d'anatomie devant lui. Après une semaine épuisante de finales et de sessions d'étude nocturnes, c'était enfin son dernier test. La liberté était si proche qu'il pouvait presque y goûter. Sa jambe rebondit anxieusement alors qu'il remplissait une autre série d... Read full Story
Femboy 2021 2023-02-17 1,033 Big Tits Cumshot Fetish Blowjob Big Cock Guy Fucks Shemale Futanari cum in mouth
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 20,079 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination 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 5,508 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
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 2,716 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,312 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
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 5,292 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
75%
A Big thank you to everyone and what's to come next year!
Hi everyone! This is something of a yearly wrap up that I wanted to write up. First I wanted to thank you all for following me this year ❤️ This was the first year that I decided to start taking this seriously and create content full time. I think I still have a ways to go to improve my content, but... Read full Story
Kate Quinn 2022-12-31 3,289 Amateur Big Tits Big Cock Shemale and Girl Guy Fucks Shemale
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 5,966 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
100%
Vegas Encounter- part Deux
Tuesday morning, it’s early and dark. Jack is in an Air BnB home in Summerlin, a suburb of Las Vegas. He met an online friend Diane and her friend/roommate last evening and we all slept in the King-size bed. I look around, Diane is sleeping curled in a ball on her side, but Holli is not here. M... Read full Story
Jon Paul 2023-12-22 5,460 anal Stockings Cumshot Bareback Asian Guy Fucks 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 5,174 anal sex Creampie Shemale Fucks Guy Guy Fucks Shemale
66%
Franks Friend
Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a ... Read full Story
shemale lover 2013-06-05 4,885 Cumshot suck threesome ass licking Guy Fucks Shemale fishnet
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 4,887 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
80%
Amber
The summer after high school I moved into this cheap hotel downtown. I'd been working in the mailroom for a large company, and really needed to get my own place, but I didn't have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I ha... Read full Story
ambersissy 2021-04-23 5,384 Crossdresser Amateur Big Cock Guy Fucks Shemale Interracial cum in mouth
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 5,143 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
Jennifer
WhiskeyIsGood I woke with a start, startled by a loud banging sound from downstairs. The floor shook from the vibrations, causing me to sit upright in my bed and glance towards my bedroom door. What in the hell, was going on down there? My question was quickly answered, by another loud bang, foll... Read full Story
Gwapo67 2022-09-13 5,997 Big Tits Bareback Shemale Fucks Guy Blowjob blonde Big Cock
33%
Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
the greatest liar 2023-07-19 4,104 anal Bareback Creampie Ebony Guy Fucks Shemale post-op celebrity post op sex
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 5,804 shemale Big Cock porn
100%
My First Ladyboy Adventure
I had been watching ts porn and thinking about visiting an escort for a while, when I found myself working in London and actually got the oportunity. I had been checking out the London Eros guide on the internet and had called several tgirls when I came across Seri Atika's profile. I called he... Read full Story
monkeyphoto 2014-10-07 10,776 hardcore Asian Ladyboy ass fucking Guy Fucks Shemale condom sex
73%
Tabitha at 19
Tabitha’s home from her freshman year of college. She’s gone off to California to a screamingly liberal school and I’m sure she’s been making new friends, learning new things, opening her horizons and fucking safely. After I popped her cherry and we had a very discreet summer of me teaching her a lo... Read full Story
Giantsquid 2017-05-16 6,659 Small Tits Amateur Cumshot Blowjob Guy Fucks Shemale cum in mouth
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 13,934 Small Tits Amateur Bareback Guy Fucks Shemale Ass to Mouth cum in mouth
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 12,641 Small Tits Amateur Cumshot Bareback Shemale Fucks Guy Big Cock domination cum in mouth
92%
The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
StevelovesTgirls 2019-06-11 12,534 Amateur Big Tits Blowjob Big Cock Guy Fucks Shemale
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 5,039 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade 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 4,318 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
Chrissy Tunnell 2022-12-01 3,633 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Lady and the Cop
A cab pulled up to the front door of the Orbit Lounge bar and three curvaceous figures, Regina, Alice and Rita stepped out, paid the cabbie, and moved gracefully towards the main entrance. They were all so jubilant and any observer would suspect correctly that they were already under the influence. ... Read full Story
Regina10 2018-03-02 2,806 Stockings Group Sex Big Tits Lingerie Guy Fucks Shemale Solo Shemale
87%
Melissa
I'm a Japanese in my early forties living in Japan and I met Melissa online about a year and a half ago when looking for someone to chat. She is a black, 6 feet 2 inches tall, around 160 pounds and therefore a slim and beautiful transgender girl in her mid twenties. From Brazil, she is very friendl... Read full Story
cttyy 2020-02-24 15,444 Shemale Fucks Guy threesome Big Cock domination cum in mouth double anal
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,730 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
100%
I was a Top before this experience
She was tall, 6 feet probably, a white colombian beauty, green eyes. Pretty gym body, strong but feminine, don't know how that works, but this was a work of art. Sweet but commanding voice, you know, similar to that voice that tells you that it's recalculating your GPS route or to turn left right no... Read full Story
Mizty 2022-11-03 6,521 Amateur Cumshot Shemale Fucks Guy Blowjob Big Cock Homemade
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 3,609 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
The Big Tiddy Goth Girl
Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... Read full Story
KaceyKlarissa 2024-02-23 4,822 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
100%
A new start in life
“In life, finding a voice is speaking and living the truth. Each of you is an original. Each of you has a distinctive voice. When you find it, your story will be told. You will be heard.” John, living outside Boston, being your average accountant working with Gillette, had gone through a messy di... Read full Story
Jon Paul 2024-05-09 2,915 anal Amateur Shemale Fucks Guy Big Cock Guy Fucks Shemale small cock big ass
62%
Man Is Humiliated By Escort
I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot... Read full Story
shemale lover 2011-09-30 7,124 sucking Big Cock cum domination
76%
Louise's Bedroom
The dark and humid night consumed the street surroundings, the rain pattered softly against the car window as Scott pulled outside Louise’s house. Louise had never agreed to let Scott visit before and he knew that this would be the only opportunity to make a good impression and be with her in the fu... Read full Story
Master VeeJay 2017-12-12 9,433 Amateur Bareback Creampie Blowjob Guy Fucks Shemale Mature
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 12,172 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
91%
The New Housemate's Secret
https://chyoa.com/chapter/Introduction.150836 The New Housemate's Secret How will you discover the hot new tenant's secret? Chapter 1 by Bauer1 The doorbell rings, a soft knocking accompanies the bell to break the silence of the house. You look up from your laptop nestled snuggly in your la... Read full Story
Acche 2019-04-04 21,978 Big Tits Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock Guy Fucks Shemale handjob titfuck titjob cum in mouth
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 5,433 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
100%
Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
Sissy Ava 2022-10-11 7,831 Stockings Crossdresser Amateur Bareback Big Cock Guy Fucks Shemale Ass to Mouth cum in mouth
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,076 hardcore sucking ass fucking Guy Fucks Shemale
100%
Leslie
Where do I start? How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I... Read full Story
Zöe from Kingston 2019-02-04 9,230 Cumshot Bareback Blowjob Guy Fucks Shemale Bra and Panties
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 4,631 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
100%
The game show,
One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... Read full Story
chris1989r 2022-01-24 4,696 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,183 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth 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 13,261 first time Creampie Shemale Fucks Guy
100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 5,111 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
93%
First time
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny... Read full Story
shemale lover 2013-07-20 4,963 first time Cumshot oral sex Guy Fucks Shemale kissing
100%
yes, Mother give it to me
"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office." Mona could feel every set of eyes on the floor anxiously awaiting the pi... Read full Story
ASSEaster5678 2018-11-28 12,758 Guy Fucks Shemale
92%
Lady In The House Chapter. 01
A story by MicheleNylons ( Man in jail is transformed to prison slut.) How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild... Read full Story
✘Transensual✘ 2019-01-11 9,431 Crossdresser Bareback Creampie Fetish blonde Big Cock Lingerie domination Guy Fucks Shemale transvestite slut PRISON FUCKBOY prison sex Prison Bitch
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%
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 7,928 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 7,779 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,342 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots