Sort by
Relevancy

Free Stories

100%
My First Gangbang
For as long as I can remember, I have always enjoyed wearing women's clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing wit... Read full Story
shemale lover 2012-07-18 10,962 first time gangbang crossdressing foot fetish
94%
My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
Betty D 2021-01-18 8,314 first time Crossdresser Amateur Cumshot Fetish Blowjob Mature Homemade mini skirt small cocks black panties obese
68%
I meet my new Mistress for the first time
I was feeling excited about and looking forward to Friday night. The reason for this was that I intended to dress up as my alter ego, Tania Harvey, and to go for a night out to a club nearby that is popular with TG’s, TV’s and other like minded people. I took a lot of care and attention over the way... Read full Story
Tania Harvey 2017-06-26 8,035 Amateur gangbang 3some shemale on shemale dominating
100%
First Time Buying Lingerie
As a youngster, I couldn't help but notice the carousels of hosiery on display in various shops that my mother would visit. Displays of stockings and tights (pantyhose) for the discerning housewife. Brands like Pretty Polly, images of nylon clad legs on the glossy cardboard and a see through window... Read full Story
Daddybear71 2023-09-13 6,347 Stockings Crossdresser Amateur Masturbation Lingerie teen (18+)
93%
First Time I tasted Tgirl Sperm
I met a Mexican Trans girl online from Hermosillo and we hit it off and corresponded for a a few months. The vibe was good and ended up deciding that I would help her pay the $140 bucks for her 6-month tourist visa to come up and visit..the process took forever but once she got it, I booked her a pl... Read full Story
AllenB 2022-08-09 8,598 Crossdresser Amateur Cumshot Latina Bareback Creampie Shemale Fucks Guy Fetish Blowjob Interracial Homemade cum in mouth
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,000 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,118 first time ass Cumshot suck cd sissy make up
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,842 first time sucking fuck domination
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,009 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
93%
Sissy Maddie's New Apartment Gangbang
I’d just moved into the big city. Me on my own in a cheap apartment block. The flat was nothing special by any means, and the room next to mine seemed to be noisy with parties. But I was glad to be on my own. I had almost finished unpacking my belongings when I came across my stash of female clothi... Read full Story
sissymaddiex 2020-09-25 9,861 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
HELPLESS TO MY CRAVING FOR BLACK COCK
This is a totally true account of my addiction to meth and its hand in turning me into the he[pless sissy I've become to my weakness for BBC. My name as a regular male is Richie Budd. But by reading this you'll soon realize that nothing is normal. Not only was I Richard Budd. I spent an equal, if ... Read full Story
Tvtrinity 2021-04-07 9,698 Crossdresser Amateur Group Sex gangbang Interracial transgender sissy bbc Black Owned owned white boy pimped force feminised BNWO
100%
A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
shemale lover 2012-03-05 14,093 Fetish bdsm crossdressing bisexual
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 3,441 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Creampie Big Cock gangbang redhead Guy Fucks Shemale Ass to Mouth cum in mouth
83%
Gangbang
I was just out to show off, and have a good time wearing a short skirt and high heels at the local TV club. Tonight, though, I went a little farther than usual. I had bought some new things, and I was dying to show them off. I wore my latex rubber corset: pitch black, very tight, and very heav... Read full Story
shemale lover 2012-12-15 5,837 Fetish gangbang crossdressing
100%
Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
Regina10 2021-04-09 4,372 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Barbie Jo Adventures Part 5
Friday Night I've gone all week as Joe; no one at work has said anything to me about Monday morning. So I assume I got away without being exposed as a cross dresser. I was working late all week and finally Friday is here. I am so horny and anxious to become Barbie Jo. Hopefully someone will call,... Read full Story
shemale lover 2012-02-18 4,257 sucking Fetish cum swallowing
100%
Carla goes out
As a cross dresser who loves to dress as a dirty slutty girl I was sat at home thinking about what it would feel like to go out dreesed in public. I had often thought about it but never had the courage to do so. I was so fucking horny and wished I had a reason to go out and do something rather than... Read full Story
Carla Kitten 2018-01-16 8,151 Crossdresser Amateur gangbang Homemade
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 7,185 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
33%
sex
Hello I am mahan Very handsome and curious. The date goes back to last year. With our sister, Sepehr, from childhood, we were on the floor of Khalmun Arshida's daughter. One day we went out with the scene, Arshida called me and his parents went to Istanbul and that lone. And asked us to go over the... Read full Story
sima2000 2019-04-18 3,586 Amateur Big Tits Creampie gangbang Shemale and Girl pov double anal
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 9,272 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
100%
Continua mi mundo Tv
Como les decía a mis 20 años ya era otro mundo, ya compraba mi propia ropa intima femenina mas que todo ropita muy chica, pues siempre he sido muy delgad@, a esta edad aun era virgen pero con hombres ya que aproximadamente a los 17 le robe un consolador a una tía, "les admito que ha sido uno de ... Read full Story
Carla Travesti 2018-12-10 2,549 Small Tits solo Amateur Latina Masturbation Fetish Ebony Sex Toys morena flaca venezolana deportista morbosa
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 7,489 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
92%
Showing my femininity
When I was still little guy, my stepfather always told me I wasn't a real boy, but I was his little girl. One day, he was drinking beer with his friends, so he grabbed me by the arm, pulled my shorts down and showed off my teeny cock to them. I remember that all of them laughed at me. They made fun ... Read full Story
Shemale Dill 2020-04-27 7,864 Crossdresser Amateur Group Sex Blowjob Big Cock gangbang Lingerie
50%
The Bottles
Fred shivered in the cold winter air. With his head down and feeling very self-conscious, he trotted out of Birmingham New-Street station in the strappy high-heels and headed down the road as he had been instructed. He couldn’t believe he was doing this. It wasn’t that it was the first t... Read full Story
shemale lover 2011-11-06 2,623 shemales Fetish bdsm
87%
Dani & Paulie - 1
It was two years since Carl had taken me in the cellar of that bar. Paulie and I had moved to a large apartment courtesy of an unexpected inheritance from his father. I should really say "her" father, we had started using feminine pro-nouns for each other somewhere along the line, no one could reme... Read full Story
SissyDani31 2018-10-08 3,939 Crossdresser Amateur
50%
Let me introduce myself
Hi everyone this is my first time cumming out to the public. I been cross dressing for about 20 years now. I’m 30 years old now. I started dressing up in my mother’s and older sisters clothes every chance I got. Both of them had swag so I dressed cute af lol. Now it’s my girlfriends clothes. I love ... Read full Story
Wet boy kitty 2021-02-01 1,769 Stockings Crossdresser Amateur Cumshot Creampie Fetish blonde Ladyboy Lingerie
100%
A Couple and Me
I have obsessions. I have compulsions. I suppose everyone has them but not many of us act on them. I do. Every chance I get. I obsess and compulse on being gang banged, or on anonymous sex or on sex with young guys (sometimes girls too). I get into bondage and being forced and sometimes on violent s... Read full Story
shemale lover 2012-02-25 3,288 Fetish threesome transvestite
100%
A Reluctant Gang Bang
Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... Read full Story
shemale lover 2012-05-28 8,453 anal sex Creampie Fetish gangbang crossdressing
100%
Blushing Bride Chapter 6
Chapter Six: Wedding Presents I was on an incredible high for a couple of days after my wedding. Like many bridegrooms on the day, I had felt very nervous, both about the day itself and the years of married life that stretched out before me. Only, I had a little more to be nervous about than many... Read full Story
shemale lover 2012-07-21 4,032 Cumshot Fetish oral sex
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 4,231 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
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 4,923 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
80%
Lingerie under clothes in public xx
My name is Rachel x I have been wearing the most amazing sexy lingerie for years, On my own and in the privacy of my own house. However, one day not long ago, but after many years of perfecting the art of being turned on so much by what i chose to wear, I decided to get completely naked, and start... Read full Story
X Cute Rachel X 2022-12-12 3,530 Stockings Crossdresser Amateur Masturbation Fetish Lingerie
100%
A Letter to my Master
A letter to my Master telling him how I felt after the other night Master is coming round tonight and I have the flat to myself. He wants me dressed and ready for him. Good! I am aching for his meaty manhood and looking forward to tasting his cum. He has given me instructions as to what I must... Read full Story
shemale lover 2012-03-16 3,841 Fetish orgasm fucking crossdressing
81%
A pervy uncle invited me to his house at 10 PM..!
It's been 8-10 years now, I had this amazing experience. I was standing at the bus stop in my area/street(my daily routine), one uncle was watching me but I ignored eye contact as I feel awkward the way he was looking at me because I act straight in public and I felt that he's seen my girly ... Read full Story
Cindy Sky 2021-07-20 7,080 Teen (18+) Small Tits Amateur Cumshot Outdoor Bareback Creampie Fetish Blowjob Asian Ladyboy 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 5,608 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 3,742 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl cum in mouth
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 9,884 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,828 Stockings Big Tits fucking foot fetish
100%
Becoming a Free Spirit
She lay dying in my arms. A brief smile came across her face. She croaked "honey remember that idol I told you about locked away in the safety deposit box?" "Yes dear but save your strength okay, I'm not concerned about some idol" "But I have to tell you about it. I... Read full Story
shemale lover 2012-03-02 2,921 sucking Fetish cum fucking Sex Toys fantasy
57%
Cumming and peeing in public while driving.
As I have previously posted, when I have my cock ring on a weird sensation exists, I feel like I need to pee more often than normal, but about 90% of the time I feel like I am going too cum. Weird one today, on way back from checkup at the doc, driving home, I started thinking about taking my coc... Read full Story
shaper2000 2019-08-05 2,913 solo Amateur Outdoor Masturbation Fetish
80%
One night Transtand ;)
One Night Transtand By BalkanMan990 Published on Lush Stories on 05 Oct 2019 I had no idea she was a trans.. I didn't stop kissing or fondling her when I found out. I went out for a drink at one of the many bars at Croatia,where my girlfriend Sabina and I were staying.Sabina and I had been drin... Read full Story
BalkanLoco91Ri 2019-10-24 8,835 Small Tits Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob blonde Lingerie Guy Fucks Shemale Homemade pov cum in mouth
100%
Father-in-law is my slave--001
Partly real partly fictional The sun shining down the room, I lazily opened the quilt, it has been cold for several days, I got up and looked at myself in the mirror, with a handsome face, but I was wearing a pink silk skirt pajamas and a pink silk low waist bag Pants, there are things in the pants... Read full Story
kelly2014 2021-03-30 4,975 Stockings Crossdresser Amateur Fetish Asian Lingerie domination Futanari shemale + shemale
16%
Current Fantasy
I really wanna get fucked for the first time and my dream way of doing it, always wanted to do a porn. The dream is that I go there and get done up in such a way, I am unrecognizable, just looking the best. Have a tranny come in and do my make up, the way she likes it and gives me a preview of what ... Read full Story
martley 2023-06-30 5,125 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,545 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 2,635 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
The Girl Next Door Ch. 03 by derezzed ©
Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... Read full Story
StevelovesTgirls 2019-06-11 18,482 Amateur Shemale Fucks Guy Fetish threesome Blowjob domination Guy Fucks Shemale Ass to Mouth shemale + shemale
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 3,804 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
66%
More from my closet....
......being single is so better to play my games, no wives to take up my day, no one to lie to anymore about where I went... I had a layover for 3days in Vancouver last fall, three days all to myself, with the aid of google maps I found the local steambath for men. Steamworks it was called, set... Read full Story
badbadboi667 2020-12-03 3,196 Amateur Group Sex Outdoor Bareback Fetish gangbang domination Ass to Mouth amature
100%
A busy Friday night
I had been looking forward to this weekend for a month. My wife was going to visit some friends in NYC, and I was staying home, by myself. Yup, just me and all of my favorite things, like stockings and panties, and sexy little outfits. The torture was finally over, and the Friday she was to leave, a... Read full Story
shemale lover 2012-02-28 3,784 anal gay male Fetish
76%
Porn Princess
They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... Read full Story
shemale lover 2012-09-02 23,873 Cumshot Blowjob fuck fingering big boobs
100%
Making my CD slut fantasies become real
Having an open mind and saying yes to a TS friends' idea has lead me to discover things I never even knew about myself. I’ve always been into kink, but my adventures as a CD have shown Me that I have filthy perverse cravings to satisfy with people I’ve yet to meet. I enjoy transsexual escorts and th... Read full Story
pinkybrown666 2021-05-20 5,277 Crossdresser Amateur Group Sex Creampie Fetish threesome gangbang Interracial cum in mouth blonde cd
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 3,887 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
50%
Sissies Training Part 2
I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by ... Read full Story
shemale lover 2011-09-17 6,480 shemales Fetish bdsm
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 6,625 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature cum in mouth
66%
Becoming an identical twin part I
My name is Cody and I recently turned 19 years old along with my twin sister Cassidy. She is older by 4 minutes and is the apple of our parent's eyes. She is in almost every aspect a goddess. Her beauty, intelligence, humor, sex appeal, and just about any other trait you can think of she is flawless... Read full Story
Chloe6942 2018-08-23 7,366 Teen (18+) Amateur Fetish
76%
My body became a gift for them
My name is Lely Bella Calistia, I am a shemale and I once had a boyfriend named Reza, she was handsome, muscular, sexy, and romantic, I was dating for a year. And a few years ago I broke up with him, because he made me a bet. At that time me and he planned a vacation to the villa where my boyfri... Read full Story
Bella Calis 2018-04-09 6,791 Amateur threesome Asian gangbang Guy Fucks Shemale