Sort by
Relevancy

Free Stories

80%
Beautiful ladyboy Natalie
Feasting comes after fasting. What's with you guys, it's been over a month that i haven't seen any new shemale stories from you, and now i'm getting them every day. Which is good of course. ;) Here's a shemale story from Tommy about his long-standing shemale fantasy finally fulfilled. I'd had she... Read full Story
shemale lover 2015-05-03 5,367 sucking shemale cum
50%
I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
Oldslut Sissy 2024-04-15 8,930 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
50%
Being Shemale
Every night I wear make up and dress up in a sexy lingerie. I stand in my balcony late night trying to lure men and women driving on the road. Last night a truck driver stopped near my house to inspect his vehicle. During his inspection he suddenly saw a long legged booty women in the balcony inf... Read full Story
babydriver 2024-06-04 2,280 Stockings Crossdresser solo Outdoor Ebony Asian Ladyboy Lingerie big ass sissy femboy
100%
Being Shemale Part II
After sometime the driver left. Night Two I was again ready by 10 Pm as usual wearing make up and sexy night outfit. My push up bra helped my breast look very attractive looked perfect with my slim body I was standing as usual in the balcony around 11 PM and the driver stopped by again.... Read full Story
babydriver 2024-06-04 2,287 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy Lingerie domination small cock big ass Frottage sissy femboy
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 7,024 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
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 5,449 anal sex sucking shemale
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,612 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
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 13,845 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 14
"Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't-" "Th... Read full Story
shemale lover 2011-08-23 5,058 anal sex asshole Big Cock
100%
Bangkok Night with Thai Ladyboy Dancer
I was visiting Thailand back in the 90s and was blown away by the “Potpourri” of sites, sounds, and smells (not all of them good) of this city. Beautiful women were at every corner and very friendly to foreigners. I went out with a group of guys on the town after dark to check out the go-go bar scen... Read full Story
AllenB 2022-04-20 5,825 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,319 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 3,748 Masturbation pussy shemale
70%
Shemale Gangbang
I am not your average female. But I guess I am not your average male either. You see, I am a tranny. I make a really hot woman. I am 5'10", am slim and have dark, wavy hair that comes down to tight between my shoulder blades. The only thing I was missing was beautiful tits. So I got those as we... Read full Story
shemale lover 2011-08-27 17,401 anal Blowjob cum swallowing
100%
Admitting My Secret Part 2
"Get on your fucking knees pig," the powerful Dom demanded. I was naked in Master Steven's basement dungeon. My wife Julie was fully dressed and sitting in a chair in the corner of the room watching me submit to a man. I was not gay, but I have always been very submissive and I had rece... Read full Story
shemale lover 2011-12-11 3,775 sucking shemale
100%
First time with a cute ladyboy
It had been a long week at work. So I decided to go to the Sound Factory for a drink and maybe get lucky with the ladies. As soon as I got to the bar, I spotted a beautiful asian lady wearing leggings with pantyhose and a sexy little top. She offered to buy me a drink, who am I to refuse. So we had... Read full Story
shemale lover 2013-05-07 10,975 Cumshot suck Asian Ladyboy pantyhose
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 95,877 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 5,120 shemale gangbang facial
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 6,098 anal sex Creampie blonde shemale
100%
A Not-So-Small Piece of Heaven
I'd never really been one for going out to bars to pick up women, but tonight was a bit different. It was my buddy's birthday, and he decided to invite me and a couple of other friends out to go bar hopping with him. Living in Miami, there was always something going on after the sun went down, so th... Read full Story
shemale lover 2012-04-28 3,826 Blowjob shemale handjob
64%
Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... Read full Story
sach 2015-11-16 7,324 Big Cock ass licking redhead rimming Shemale on Guy
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,673 Stockings shemale oral sex bisexual
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 9,457 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
60%
Shemale Chrissy Fucked by a Demon
I wanted to write this the night it happened, Halloween, but I was still so traumatized. I was at my fictional fantasy Sugar Daddy's house alone and already spooked out by the noises of this old hundred-year-old wooden house in this loud thunder storm on what some call "Devil's Night." I had to turn... Read full Story
Chrissy Tunnell 2022-12-01 4,082 Small Tits Crossdresser Amateur Bareback Fetish Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
75%
Shemale gang-bang
I have been surgically modified by my mistress I have a small 6 inch penis (functional) I have no body hair except for my ‘pussy’ My anus had been surgically loosened for better sexual performance (can now tightly accomodate penises 2.3 inch diameter and 9 inches long) I have large... Read full Story
shemale lover 2012-03-26 4,689 Creampie gangbang domination
88%
First Time Outdoor Festival Fantasy
Fantasy Setting: Summer time in the mountains of Colorado the perfect bluebird weekend we all dream of. The day before an underground rave in the mountains all my friends bail on the show and was now left with either not going or going solo. Well I deiced what the hell and I'll go solo an... Read full Story
xaviergc8 2016-10-26 9,571 anal first time shemale gangbang bondage outdoors fuck toy
100%
Shawshank affair
Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... Read full Story
Jon Paul 2018-08-20 6,591 Stockings Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale Ass to Mouth 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 32,598 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
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 5,670 Shemale Fucks Guy Blowjob Big Cock Asian Ladyboy big boobs cum in mouth shemale fucks male Indian Shemale Pune
77%
Chicago TG Romance (part 3)
It is Sunday morning, just barely dawn and I have just spent the weekend with the most amazing girl. You know when everything clicks and it seems that at first you have met the person you want to spend time with and share with. Beth was standing at the glass windows full length and the sun was just ... Read full Story
Jon Paul 2018-06-04 4,267 Cumshot Asian Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
66%
Ladyboy dominatrix
If you read my other stories you know I'm intersexed and I was a ladyboy prostitute when I was um, very young. I don't condone such activities. They were sick perverts who used me. True I got a lot of money and expensive gifts but that doesn't make it right. They should all be castrated. Th... Read full Story
shemale lover 2012-10-15 9,885 Fetish Asian domination sissy rimjob
50%
La pistola NEGRA del Tío, entre Las Bragas de Mi Tía LA PUTONA
Aaayyy.. Yo sabía que la Tía había sido Flor de PUTONA.. pero, jamás me imaginé que me iba a tocar a mí 'hacerme cargo de sus cosas'.. su 'herencia'.. la casa ya vieja, por reordenar destinar y.. LAS COSAS que una descubre ya con los años! Todo estaba igual, pero HORRIBLEMENTE ARRUINADO.. más, e... Read full Story
Ari Riè 2021-06-03 2,113 Teen (18+) Small Tits Crossdresser Latina Bareback Shemale Fucks Guy Fetish blonde Big Cock Uniform Lingerie domination Premium HD
80%
Brazilian Discovery Chapter 4
John, the husband of Susan (see Susan and John series) has travelled to Brazil for a one year training session. Mr Gupta has sent him as the pretty little Joan, in the hope he would lose any interest for Susan and leave him totally free to deal with his senior accountant! The corset maker had bee... Read full Story
shemale lover 2012-08-25 4,131 cum oral huge cock brazilian
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 5,166 Masturbation shemale and shemale Big Cock condom sex ass fuck
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 10,754 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
100%
Trans State Private School
Tommy heard a rumor that the Trans State cheer leading squad (even though it had the prettiest, sexiest girls in the state), all had cocks hidden in their cheerleader panties. His school was playing Trans State that day, and Tommy had to find out if it was true. The squad was on the fie... Read full Story
shemale lover 2012-01-04 5,338 shemales gangbang cheerleader
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,250 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,477 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
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 7,600 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
80%
fuck by my best friend's family
= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... Read full Story
Onikky 2019-06-25 9,370 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
88%
Purple Kiss, part 1
It happened during a week long trip for work. By the third night in a strange city I had grown tired of the hotel bar and broke away from my work colleagues for change of scenery. I told my coworkers that I was going to bed then quickly made my escape. The night was warm so I decided to take my o... Read full Story
Transadmirer 2016-01-02 10,077 Creampie Shemale Fucks Guy Fetish cum domination gangbang sex
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 4,577 shemale cum ass fucking
87%
Fem Firm 3: The Return Of Frankie
PART 1 THE VISITOR Over the next couple of months, it was pretty much business as usual at the Firm. You know, depositions, court filings, motions, hot sloppy blow jobs and ass destroying anal sex (Thanks Angela!).Not to mention Friday Fuckfests. But since I started working here everyone se... Read full Story
bennyx709 2016-11-14 12,283 anal sex ass fucking oral sex cock sucking thick cock
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 5,428 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
100%
Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
smtmsbrianne 2020-09-16 3,516 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Creampie Big Cock gangbang redhead Guy Fucks Shemale Ass to Mouth cum in mouth
100%
My Noisy Upstairs Neighbors Part 3: Making Porn
In Part 2, I recounted how Paul, my commanding upstairs neighbor, coerced me into making porn with him and his younger roommate. Now, I'm excited to share the first video we created together. At 12:45 PM on Saturday, I nervously approached Paul's door. After knocking, Paul opened it with a smile ... Read full Story
Chrissy Tunnell 2024-07-16 614 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
50%
Carol, The Saga Continues
It's very late Monday night as Carol returns from the date that J C had forced her to keep, she places her purse on the hall table, throws her jacket over a chair and walks toward her bedroom. She can't wait to shed this clothing that J C demanded she wear. As she walks, her feet, clad in the five i... Read full Story
shemale lover 2012-03-09 2,756 anal sex shemale deepthroating
100%
The Day I Went SheCock Crazy
I summed up courage to meet up with my old shemale flame Fransicca (she is a Malaysian but living in indonesia) ... messaged her, she sounded excited and asked if i minded her friend joining us. 'Why not' i said. It was settled. we booked a villa for the next day. I checked in early. cleaned up ... Read full Story
Sara Banks 2021-04-26 6,564 Group Sex Cumshot Outdoor Bareback Shemale Fucks Guy Fetish Blowjob blonde Big Cock Asian Ladyboy gangbang
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,019 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 944 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
66%
Charisma & Tiffany Part 4
While bathing her in the shower stall, before pissing on her and making her drink the warm, golden beverage she’d poured from her bladder, Charisma had planned to fuck Tiffany in the ass with the aluminum Little League baseball bat she’d brought into the shower stall with her for that ve... Read full Story
shemale lover 2011-09-02 3,124 shemale domination
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 4,971 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,319 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
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 6,728 Creampie Big Cock ass fucking
92%
Southern Hospitality Ch. 04
XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... Read full Story
Gwapo67 2022-05-16 6,718 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature cum in mouth
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 5,799 shemale Big Cock porn
100%
Office Casual
"Good morning Ms. Anderson," Karen said as her boss walked past her desk station and into her office. "Good morning Karen," Ms. Anderson said, not even stopping to make eye contact, "I'm going to be very busy today, so I'll need you to let me know if you get any mail fo... Read full Story
shemale lover 2012-08-30 3,844 brunette cock Masturbation Blowjob shemale big