Sort by
Relevancy

Free Stories

100%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 6,555 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
92%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 9,111 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
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 13,519 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
100%
Dating my Sissy-sister (English)
You are wearing women's stockings and a thigh-high transparent top, the thin shoulder straps of which leave your arms and shoulders elegantly exposed! You're the real lil bunny to me in that girl outfit of yours... How about, should I teach the little one about the naughty girl? You're giggling a... Read full Story
LulaSissy 2024-09-24 2,961 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female fucking sissy
100%
Alessia and the Twins
Alessia and the Twins When the politician David Smallwood awoke that morning his thoughts immediately turned to Alessia, and he started to daydream about her, as he was wont to do now. He had several meetings scheduled for that day, including a rally promoting restrictions on gay and trans-gender... Read full Story
Alessia Travestita 2023-07-21 5,658 Crossdresser Blowjob Big Cock Shemale and Girl shemale fucks female
100%
Shawshan part2
The summer weather has finally let up and cool evenings where you need a sweater are among my favorite times of the year. Charlene left now from prison and served her time for drug possession. We had become close friends as well as cellmates over the last few months. She no longer cuts her hair as ... Read full Story
Jon Paul 2021-05-20 3,529 Latina Masturbation Bareback Shemale Fucks Guy threesome Guy Fucks Shemale shemale + shemale
81%
First time shemale encounter
Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very ea... Read full Story
iloveshemales112 2011-12-17 9,833 Latina Bareback Shemale Fucks Guy Big Cock
100%
Surprise Ending (The End)
Karla struggled a bit to get the huge, bulbous head of her cock inside of me. It was like my ass had licked a battery. A charge went through my body that while painful, was exhilarating and exciting. "Ahhh," from my lips was all the encouragement I could offer and Karla took it. She steadily push... Read full Story
Chantel13 2022-08-23 5,795 Amateur Outdoor Shemale Fucks Guy Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth
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 6,958 Big Tits Cumshot Latina Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale
94%
My Shemale Fantasy
Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... Read full Story
Jakester 2013-04-10 32,249 first time Creampie Shemale Fucks Guy ass licking virgin
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 14,386 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
66%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 6,376 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Shemale fantasy with female squirting
I just finished my mornig coffee at the breakfast bar in the kitchen when the door beel rung. My wife opened the doo and it was one of her hot friends. She invited her to sit at the bar beside me and serve her a coffee. Right before she gives her the coffe she slips something into the brew. Her ... Read full Story
TRTRAIN 2023-05-21 3,851 anal Stockings Amateur Big Tits Big Cock Lingerie Shemale and Girl pantyhose Mature Homemade Ass to Mouth cum in mouth shemale fucks female
100%
Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
Regina10 2020-12-04 7,353 Stockings Crossdresser Big Tits Cumshot Bareback Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale pov Ass to 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 5,689 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
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 4,872 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to 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 6,791 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
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 33,074 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,538 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
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 40,720 first time anal sex suck Shemale Fucks Guy Guy Fucks Shemale
100%
Loosing my virginity to Shemale Preet
This story is of may be 2017. When a shemale escort took my virginity n fucked me. I am not new to shemales. I hv been attracted to shemales since 1999 when first time I got internet at home. Suddenly while browsing i saw shemale website n instantly i was hooked to it. Well how I met my first ... Read full Story
Stud4Shemale 2021-02-20 8,530 Bareback Shemale Fucks Guy shemale fucks male first time with a tranny Indian Shemale Pune Sucking Shemale Cock Loosing virginity to shemale
100%
Honeymoon Suite
Two days after having been gang banged into ecstasy, I got a call from Lucas, one of the gang bangers who had brought me so much joy two days before. I was elated, but I tried to be calm and not let him know how happy I was to hear from him. He wanted to get together, just the two of us, for a more ... Read full Story
Regina10 2020-07-10 5,275 Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale Ass to 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 23,110 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
100%
Bareback fuck by Lysa Shemale
Well I am devoted shemale lover and have met many shemales in my life. This incident is of probably December. I called my shemale escort Amy to meet and some how she was not picking call. Then around 4.30 pm she picked n told me that she is having hangover due to party so was sleeping, so I sh... Read full Story
Stud4Shemale 2021-02-20 7,652 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob cum in mouth barebackedshemales shemale fucks male cum in ass Indian Shemale Pune
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 4,718 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
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 95,090 tranny sex toy anal sex suck Shemale Fucks Guy dildo
50%
How Sia Shemale Pune fucked me ...
I met Sia through ts-dating . Called her n went to meet her. When I saw her I could not believe that she is shemale n has got cock between her legs. My god so beautiful feminine. Her implants are very sexy n make her more beautiful... Then I paid her n we went to comfortable small bedroom. I d... Read full Story
Stud4Shemale 2021-02-19 6,118 Shemale Fucks Guy Blowjob Big Cock Asian Ladyboy big boobs cum in mouth shemale fucks male Indian Shemale Pune
100%
2 Faker, Eierlose, Blockierlistenuser und ein paar richtig geile
Freitags sind Fimia und ich an die Bi-Night im CW Volketswil gefahren. Als wir eintrafen, waren schon viele Freund:innen auf der Terrasse anwesend. Wir fläzten uns zu ihnen auf die Liegen und schon bald wurden allerlei Zärtlichkeiten ausgetauscht. Da wurde gefummelt, hier wurde geblasen und sogar da... Read full Story
Cheryl_F 2024-09-02 277 anal Cumshot Outdoor Bareback Creampie Fetish Blowjob Big Cock Lingerie Shemale and Girl shemale fucks shemale cum in mouth shemale fucks female
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 8,027 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
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 5,125 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale 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 12,264 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
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 12,515 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
100%
Bi-Night 18.09.24
Wieder war die Bi-Night im Cruisingworld Volketswil angesagt. Da Fimia und Andrea in Mykonos im Urlaub sind, habe ich mich allein auf den Weg gemacht und bin so gegen 16 Uhr eingetroffen. Eine nette Begrüssung am Clubeingang und schon ging es in die Garderobe. In der Garderobe sprach mich auch glei... Read full Story
Cheryl_F 2024-09-02 320 anal Amateur Creampie Fetish Blowjob Ladyboy gangbang Shemale and Girl sissy pov shemale fucks shemale shemale + shemale shemale fucks female
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 11,610 Shemale Fucks Guy sissy Halloween
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 31,809 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
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 12,260 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