Sort by
Relevancy

Free Stories

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 6,776 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
0%
Looking-Glass Ladyboy
I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding ... Read full Story
shemale lover 2011-10-29 7,406 asshole Fetish Ladyboy
85%
Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
shemale lover 2014-09-17 60,625 suck Bareback Asian Ladyboy ass fucking
90%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 13,046 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 4,825 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
71%
Thai Ladyboy Interview
An Afternoon With Some Thai Ladyboys I spent this afternoon with 6 Thai ladyboys. No, don't go thinking that I tried them out. I didn't. I spent a few hours chatting with them, finding about them, trying to understand what makes them tick and learning about their experiences and the guys who util... Read full Story
shemale lover 2012-08-11 12,174 Fetish Asian Ladyboy
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 10,545 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
79%
Fucked and sucked by a ladyboy
Our reader Maxie wants to share what it is like to be fucked up bottom by a ladyboy and getting a blowjob from her at the same time. Seems very exciting, what do you think? ;) On a recent visit to Thailand I went further than I ever thought I would. I picked up a "young lady" Bangkok wh... Read full Story
shemale lover 2015-02-09 9,907 suck Ladyboy fucking
80%
Ladyboy Loves Up The Midwest
When Jasmine, a Thai ladyboy, moved into a small town in Iowa the locals didn't know what had hit them. She was instantly the talk of the town; initially for being so different and exotic but once she opened her club her reputation spread right across the county and state line. It was only a real... Read full Story
shemale lover 2011-10-08 6,016 Blowjob Ladyboy massage
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 5,235 sucking shemale cum
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,306 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
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 10,777 Cumshot suck Asian Ladyboy pantyhose
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 7,466 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
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 95,410 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
The reason why I became a crossdresser
At first, I was just a straight and ordinary boy who was into sexy lingerie, stockings and heels. But one day, I suddenly thought that I wanted to try on my mom's panties, stockings, and high heels. So I did it. It was so excited and I started to get addicted to cross-dressing. Before dres... Read full Story
cdmisato 2024-02-28 5,336 Crossdresser Asian Ladyboy sissy
100%
Towel Boi: Agreement Signed
Ralph moved the mouse to wake up the computer. He navigated to his legal docs account and downloaded a generic pre-existing relationship agreement. He asked for the spelling of the new hire’s first and last name. “First name K-A-S-E-Y. Last name S-T-E-V-E-N-S.” “Got it,” acknowledged the owner. ... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,604 Crossdresser Bareback Creampie Blowjob Guy Fucks Shemale Interracial small cock big ass sissy femboy
100%
Transsexual Sisters Chapter 3
Part 3: Their First Men Dawn and Cassie searched for Michelle and Nicole. They did not appear to be anywhere in the club. Pixie saw them looking and told them: "Your ladies left a long time ago with their new friends Marty and Brandy." Pixie said. They left me a note for you. "H... Read full Story
shemale lover 2012-09-07 2,702 Blowjob Big Cock fuck oral sex tits licking
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 3,673 sucking Fetish Ladyboy rimjob
80%
What I like
I like cum from cocks, a copious creampie dripping from a pussy, or licked off a warm body. I'm an older guy but I'm still fit, active and horny all the time. I like to masturbate while looking at porn with a prostate stimulator up my ass, wearing nipple clamps and a cock ring after smoking some pot... Read full Story
SylvesterLeChat 2023-08-15 4,359 Masturbation Creampie Blowjob Big Cock Ladyboy Mature small cock sissy cum in mouth
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 6,392 Stockings Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,003 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
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 4,090 Cumshot Asian Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,001 Big Cock cumming sperm ebony 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 5,529 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
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 5,213 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
92%
Thank you for Paradise
This hot shemale story was sent to me by our forum member Leeya and i'm anxious to share it here with everybody. It's a classy story about a guy who went to an Asian country on a business trip and met a very beautiful womain in a very romantic atmosphere... Little did he know that this young voluptu... Read full Story
shemale lover 2015-03-13 6,240 anal Asian Ladyboy
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,375 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 3,808 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
100%
A SLUT is born...
I've always had this magnetic attraction to slender pointy hi-heel stilettos for as long as I can remember. Even when I was just a kid of around five years old, I used to get these strange feelings between my thighs every time I saw a young teenage girl strutting and teetering around on these f... Read full Story
caroletv31 2018-04-23 6,762 Stockings Amateur Masturbation Ladyboy Lingerie cum in mouth
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 4,763 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
50%
The club
"Okay ladies," Missy said to her guests, "relax and get ready because I have a very special treat for today's meeting!" "What is it?" and excited Jayne asked while removing her sweat shirt and jeans. "Now you know better than to than that" Missy replied with a... Read full Story
shemale lover 2012-05-03 4,355 Group Sex Cumshot Ladyboy fingering Sex Toys
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 5,723 anal Cumshot Ladyboy oral
100%
Joe gets to the bottom of things
She kept it tucked away, uncomfortable, squeezed between her legs held in place by the tight rubbery panties that really weren't her style, but they punctuated the "surprise". Joe was aroused by her femininity, as she slipped off the spaghetti straps of her little white dress revealing the... Read full Story
keeponst 2012-10-08 2,771 sucking Ladyboy virgin
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 3,986 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
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 7,226 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale 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 1,818 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
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 13,302 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 7,409 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
100%
Cheating Sissy Wife chapter2
My sweetheart Keith is back from his road trip and we were about to make up for lost time. He didn’t even want me to fix dinner. Instead he said that we would order pizza later. Meanwhile we started making out right there on the couch. We were both horny and anxious to get next to each other. I felt... Read full Story
Regina10 2020-10-26 4,544 Crossdresser Big Tits Cumshot Bareback Creampie Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth
100%
Late Night Snack (Touch me in the morning)
I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... Read full Story
Regina10 2024-03-28 2,706 anal Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ebony Ladyboy Lingerie
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 31,027 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
80%
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 5,767 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 4,081 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 3,379 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Charisma & Tiffany Part 1
As a beautiful shemale, Tiffany De Vine had had a lot of superb lovers, both male and female, but she couldn't get Charisma off her mind. She'd met the sorceress when she'd bought one of the brassieres that Charisma had designed. Actually, as she found out later, it was the only brassiere that Chari... Read full Story
shemale lover 2011-09-01 3,038 pussy oral sex tgirl
66%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 4,250 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
83%
More Than a Lady
Doctor Carter surveyed the gathering of ladies before him. Something wasn't quite right, but he just couldn't put his finger on what it was. He had been invited to speak on Female Reproductive Health but the women before him were neither the charity-driven older matrons nor eager young housewives th... Read full Story
shemale lover 2011-11-24 4,209 pissing Ladyboy Mature
42%
Becoming Alanna Part 1
My name is Alanna Monroe and i am currently a college bound 17 year old senior at St. Anne's school for girls in Middletown Conn. I was once Alex Monroe, but after one fateful day four years ago, I became Alanna. Being a proper “lady”, i have all of the assets of my classmates...well tha... Read full Story
shemale lover 2012-07-12 4,653 shemales Ladyboy
100%
Transsexual Sisters Chapter 2
MICHELLE AND NICOLE TRANNY SISTERS Part 2: Living with lesbians During freshen orientation the girls kindly declined approaches from many men and some women. They needed to find their bearings and were not ready to reveal any hidden secrets yet. They first needed a place to stay and searched t... Read full Story
shemale lover 2012-09-07 3,910 Cumshot Creampie Blowjob Big Cock tits licking
80%
Me and 2 black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... Read full Story
shemale lover 2013-06-22 5,388 Cumshot suck Ladyboy Guy Fucks Shemale Interracial swallowing
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 3,443 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
85%
An Unintentional Fisting
During the last weekend I ended up being busy, which I hadn't planned since that was suppose to be a weekend of anal bliss for me. I had finally ordered two new dildos and I was rearing to take them for a spin. Monday came and the day dragged on while all I could think about were the two black ... Read full Story
Purple Dagger 2018-03-02 6,701 Crossdresser Amateur Masturbation Ladyboy Sex Toys
42%
Run
I felt the cool night air hit my face as I barreled down the long sloped driveway. The rope around my ankles and knees had converted my movement to just a pathetic hop. Each hop I took caused my aching feet to hurt even more. Just my luck, I had been on my feet all day long and now the opportunity o... Read full Story
ASSEaster5678 2018-07-10 3,980 Big Cock Ladyboy escaping
100%
My story, more or less Pt.1
I always knew I was different. I enjoyed playing with dolls and being around girls, I felt safe and in my place. When I got my first smartphone I have discovered porn, and boy was it an adventure! I have watched every type you can think of, but eventually I settled on shemales, the perfect cross ... Read full Story
Thigh_High_Boi 2022-12-22 4,580 Stockings Cumshot Masturbation Ladyboy Lingerie Homemade pov
100%
Exotic Escapades Chapter 3
The smell of wood and coffee filled the quiet house as Tammy slowly picked herself up from a plush couch. Daggers of sunlight blinded her eyes as she eventually got on her two feet. Her body ached, and she noticed a small pink bandage on her left leg. The terror and pain of last night shook her as s... Read full Story
shemale lover 2012-05-05 2,849 tranny Creampie Big Cock Ladyboy fingering oral sex
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 7,336 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth