Sort by
Relevancy

Free Stories

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
50%
The BIG COCK that I will eat.
ENGLISH: Hello friends. In the link below, you can see the tranny cock that will fuck me in the days to come. I saw her advertised on the internet, I picked up the phone and called, I will see her when her clinical tests are negative for sexually transmitted diseases, because I will surely swallow... Read full Story
cuchillo 2020-09-18 7,693 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Homemade cum in mouth brunette ts swallow cum
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 4,632 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
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 32,604 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy 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 7,781 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
Being taught a lesson .......... I think!
How did I end up on my back in my own bed, legs straight up with my ankles over her shoulders, ready to have my ass fucked from a lost bet? A bet that Alma clearly cheated at as we discover. I was off to Thailand for a 16 week course in Thai massage at a school recommended highly by a friend I ha... Read full Story
Curious_billy 2023-11-12 8,208 anal Amateur Group Sex Bareback Creampie Shemale Fucks Guy threesome Big Cock domination Homemade Vintage cum in mouth
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-14 2,367 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
100%
The Tip for A Tip
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com Thank you. Now Enjoy! COVID had shook up my world pretty bad. Furloughed from my day job, I had to make ends meet. I started doing food delivery for the local ride share company... Read full Story
therefill05 2020-12-10 6,640 Cumshot Latina Bareback Shemale Fucks Guy Blowjob Big Cock domination cum in mouth
100%
Intense
Holding to my word, I didn't let the incident with Billy and his friends scare me away from Bailey; I kept seeing her, even after the beating I took. To be honest, I'm not sure if he was trying to lay low or what, but Billy seemed to keep his distance from me for a while...thankfully. Bailey and ... Read full Story
Verpa 2019-10-21 10,763 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock cum in mouth
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 56,573 Group Sex Cumshot Shemale Fucks Guy Blowjob Big Cock Ebony gangbang domination Interracial Ass to Mouth cum in mouth
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 22,180 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade 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 11,836 first time Shemale Fucks Guy Blowjob Big Cock
94%
Crossing lines
It had always been a fantasy of mine. I have very feminine features and long natural straight brown hair. Which recently I had shortened to chin length. I have been dressing in womens clothing now for many months and had decided that this was the night in which I get made up totally and head ou... Read full Story
Zöe from Kingston 2019-02-04 11,088 Stockings Crossdresser Cumshot Outdoor Bareback Shemale Fucks Guy Blowjob Big Cock Ebony Guy Fucks Shemale Interracial
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 15,446 Shemale Fucks Guy threesome Big Cock domination cum in mouth double anal
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 4,336 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + 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 7,092 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
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 5,757 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
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 4,771 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
KING OF TRANNY CHASERS ENTRY 2
LAST YEAR TO CELEBRATE MY BIRTHDAY I DECIDED TO FULFILL ONE OF MY SEXUAL FANTASITES. I HAD BEEN WITH 2 CIS WOMEN SEVERAL TIMES BUT NEVER HAD I BEEN WITH 2 TRANNIES. MY BIRTHDAY WAS ON A FRIDAY SO I SPENT THAT DAY AND THE NEXT CELEBRATING WITH MY FAMILY AND GINA..THAT SUNDAY I SET UP AND PLANNE... Read full Story
Ghostface drillah 2024-07-04 910 anal Amateur Group Sex Big Tits Cumshot Shemale Fucks Guy Fetish Big Cock Guy Fucks Shemale big ass Homemade Ass to Mouth shemale fucks shemale
100%
Surprise Ending (Part One)
My wife is the picture of professionalism from 8 to 5, but after hours she is a sexual dynamo who loves men and women. Throughout our relationship she has introduced several of her gal pals into our bedroom, hot tub, shower, etc...you get the idea. Anyway, two weeks ago she let me know that one o... Read full Story
Chantel13 2022-08-23 5,454 Crossdresser Amateur Group Sex Outdoor Bareback Shemale Fucks Guy threesome Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth 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 3,196 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
100%
I am seeking an open-minded trust worthy lifetime partner...
To all of you who are fakers, jerks, wankers, trolls and pretenders, please moveover cos im not interested in your lies and silly games. Life is too short to those who fool around or so, etc. etc... I am Top and dominant. seeking for my lifetime partner. I know im not perfectly beautiful, not a g... Read full Story
Vurikat 2022-03-29 2,764 Amateur Group Sex Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ladyboy gangbang domination
50%
I kneel in front of Dominatrix Persephone
Fan Mail. I kneel in front of Persephone.. She looks amazing in Her latex catsuit, but there is something else eye catching. Chance, Persephone huge hó rse c... It looks intimidating in picture, but just think how it must look when it is right in front of your face!! Holding it in my sissy hands, i... Read full Story
Dominatrix Persephone 2024-06-18 2,877 anal Stockings Cumshot Shemale Fucks Guy Fetish Big Cock redhead domination Interracial Mature Homemade sissy femboy teen (18+)
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 13,869 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
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 7,396 Group Sex shemale vampire
100%
My story
Please don't hurt me, I whimpered softly. Oh no my Lil slut, mommy has no intention of hurting you but making your fantasy become real, she said. But your thing, its kinda big. I'm a bit scared, I said. Mmmmmm, don't worry baby. Mommy wants this to be so good that you become my steady, she said... Read full Story
Curious_billy 2024-02-03 6,237 anal Amateur Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Mature Homemade cum in mouth
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2012-05-07 4,901 shemale Big Cock oral sex cum licking
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 33,782 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
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 4,697 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
How could I forget my first time .......
"Ok, ok, ok stop. No more. It hurts a bit" I said. "Just relax your ass baby. Push out like you have to go poo", my date said. How did I end up like this? A straight A college student, a devout Christian with a nice gf like me ends up in bed with this sexy woman ...... Ok wait, I thought she wa... Read full Story
Curious_billy 2023-10-29 8,767 anal Amateur Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Homemade cum in mouth teen (18+)
100%
She Loves Dirty Talk Too
Sexy TS Girl: Hiii! How are you? Thanks for being my new friend. I have so much love forssz you, my friend. Don't hesitate to like and comment one or two photos of me that you like. We can also chat... Love, love, love you, sexy man. HardRock: I really enjoyed looking at your galleries.... Read full Story
Hardrock51Fifty 2024-05-17 3,193 anal Amateur Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock domination Guy Fucks Shemale Ass to Mouth cum in mouth dirty talk
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 21,980 Big Tits Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock Guy Fucks Shemale handjob titfuck titjob cum in mouth
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%
My Love Letter To Joanna Jet
I await my goddess on my knees, my heart pounding in my chest as I hear the sound of your footsteps outside my door. You knock and I spring to my feet, opening the door. You enter, pushing me aside and closing the door behind you. You are radiant, tall and curvy, with long black hair, smooth cara... Read full Story
TgirlLover4Life18 2022-04-12 2,264 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy blonde Big Cock Lingerie Mature Ass to Mouth
85%
Francine Hung Shemale
This is the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in California and Mexico as ... Read full Story
darrell 2015-11-16 9,439 sucking Big Cock ass fucking deep throat butt plug
100%
Deflowering Latina Sissy Destiny
A real life story of my one and only time deflowering someone and being their first real encounter, I was 27 at the time and she was 21. I am absolutely convinced that Trans girls and CDs have a bit of a 6th sense when it comes to perceiving which guys are into them even in a public situation. I ... Read full Story
AllenB 2022-09-07 6,328 first time Big Cock Guy Fucks Shemale Homemade sissy travesti cum in mouth