Sort by
Relevancy

Free Stories

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 10,033 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
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 11,851 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
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 7,263 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
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,021 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
72%
Wie sich schlagartig mein Sex Leben änderte... Teil 1
ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... Read full Story
Holly Swallow 2019-03-20 7,771 Stockings Small Tits Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob blonde gangbang domination Interracial Sex Toys humiliation Homemade sissy girlfriend chastity cage Ass to Mouth cum in mouth chastity sissy amateur crossdresser fendom
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,579 Masturbation Blowjob blonde ass fucking big boobs
100%
Bi Pantyhose Passion
I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dress... Read full Story
shemale lover 2012-06-04 4,125 first time Cumshot Masturbation Fetish Blowjob pantyhose
92%
MY TS FOXXY & VENUS LUX FANTASY
Alyssa Gomez and Venus Lux were visiting Newark, NJ and decided to have lunch in the restaurant that I work in. It was a rainy day. The seductive pair were returning back to their suite in the Courtyard Marriott, but not before grabbing a bite to eat. Alyssa and Venus sat the bar and ordered a coupl... Read full Story
I_GO_3WAYZ 2021-03-02 11,260 Latina Creampie Shemale Fucks Guy threesome Blowjob Ass to Mouth cum in mouth double anal
50%
Gangbang: Daddy's Girl
"Oh yeah...that's daddy's girl," my dad moaned as he massaged my enormous round sticky ass. I'm 18 and my sister was about 5 years older than me, so who knew how long this had been going on for, I thought to myself. At least I tried to think as I slowly closed my eyes and bit my bottom ... Read full Story
shemale lover 2012-12-16 9,359 sucking cum gangbang
88%
LONDON CINEMA LIAISON
When I lived in London back in the 80s and 90s, I would often sneak off to a porn cinema with stockings, suspenders and knickers under my suit. My wife didn’t much like sex, so this was a release for me to get away from home and have some sexy fun. Once I had found a suitable seat I would ease down ... Read full Story
GinaG 2018-12-14 7,092 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
100%
Sissy gets her Prezzie
Justina woke up on Monday morning and was already tired, she had been dogging till 3 and her little ass was a little bit sore. She made her way to the bathroom and had a pee, brushed her teeth then headed for the kitchen to make coffee. As she was walking her phone went off, she had a text from ... Read full Story
Samantha Jewels 2022-01-06 3,205 Stockings Crossdresser Cumshot Bareback Blowjob Big Cock gangbang domination Mature Homemade Ass to Mouth
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 11,162 first time gangbang crossdressing foot fetish
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 7,612 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 7,810 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
100%
Karen, My School Teacher Part 5
The Bus Station By FoxyHosed I looked around, but no one was there. It was dark and pretty cold night outside. I felt the air blowing around and up my pantyhose encased legs and ass. Mmmm nice. I started walking to the bus stop a few blocks further down from the school. I felt very attractive g... Read full Story
FoxyHosed 2021-03-15 7,066 Crossdresser Cumshot Outdoor Masturbation Fetish Blowjob pantyhose legs pantyhose cd
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 9,914 Stockings Big Tits fucking foot fetish
100%
Just Another Sunday Funday
So I just got back from one of my favorite days: Sunday. Most people hate it because it's the day people go to church. But that's exactly why I like it. You see, every Sunday, one of my oldest and dearest lovers invites me to his home while his wife is at church. He also invites several of his frien... Read full Story
shemale lover 2013-04-19 5,047 Stockings Cumshot gangbang cum swallowing rimming
100%
Lola Chapter 5
Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... Read full Story
BellaBeau 2023-10-30 5,736 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,438 Stockings Small Tits Crossdresser Cumshot Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,439 Crossdresser Cumshot Masturbation Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale 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 5,129 shemale gangbang facial
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,072 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
shemale lover 2012-07-30 5,768 anal sex Cumshot oral sex rimjob
100%
I Love To Love You
I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... Read full Story
Brina Giselle 2023-09-24 4,996 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 7,160 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
86%
Passionate Sex with a Beautiful Shemale
a man and his shemale lover get down to business Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sa... Read full Story
shemale lover 2014-03-23 6,617 anal Blowjob shemale orgasm fingering
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,501 Crossdresser hardcore ass fucking cd
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,004 big dick anal sex suck Blowjob cock sucking workplace
100%
A Natural Sissy Part 4
The Next Day I was up early, and called to set up a surgery for Stacy’s breast enhancement. The hormones were working but his tits seemed to have stopped growing at a B cup. I wanted him really top heavy. At least a D cup, maybe a DD. I let the exhausted sissy sleep. As I was finishing u... Read full Story
shemale lover 2012-03-24 3,902 Stockings Fetish cum oral sex sissy
61%
Car Broke Down
A Fantasy: Car Broke Down My car was running hot so I pulled into a driveway so that it would cool down. I got out and raised the hood and added some water. I then got back inside and smoked a cigarette and sipped on a beer that I had. I listened to the radio and glanced out the window and... Read full Story
iluvgurls 2018-11-14 7,331 Small Tits Creampie Blowjob Lingerie cum in mouth
100%
Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
darrell 2022-01-03 4,635 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,518 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
88%
Making love on the beach
= First = My name is Lely Bella Calistia, I'm an Asian shemale, I'm 27 years old, and I now live on a very beautiful island in Southeast Asia, I have only been here for 2 years and have a nice new life. I have a friend when I was a child, and we are good friends until now, but unfortunately wh... Read full Story
Bella Calis 2018-10-22 6,170 Blowjob Asian gangbang Guy Fucks Shemale
85%
The Gang
I had always thought of myself as female in spite of the fact that I was born with male genitlia. Even in my earliest memories where I had witness sex, I identified with the female in the relationship. As a small young child, I had always longed for womanhood each time I heard a woman sing or especi... Read full Story
Regina10 2020-06-29 8,892 Group Sex Cumshot Blowjob Big Cock Ebony gangbang double anal
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,639 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
50%
"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
Femboy 2021 2023-01-20 1,309 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
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 13,929 first time sucking fuck domination
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 4,698 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,361 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,461 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
50%
Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
shemale lover 2012-02-01 6,328 anal shemales Group Sex
37%
First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
shemale lover 2013-07-17 6,095 first time Crossdresser Fetish Mature bisexual
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,293 Crossdresser Cumshot Blowjob jerking pantyhose
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 7,485 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
50%
A Perfect Life
The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... Read full Story
shemale lover 2012-05-05 12,572 transgender
100%
Vegas Honeymoon to Remember
I had dated my wife (Carmen) for about 6 months before we decided to Marry. One evening we were soaking in the Jacuzzi together and drinking wine. She always wants to try different things, which makes our sex life wonderful. Carmen asked me if I ever had any fantasies. I said I guess like most me... Read full Story
Jon Paul 2018-05-30 20,408 Group Sex Cumshot Bareback threesome Ladyboy Shemale and Girl
75%
TV-TV
My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had eve... Read full Story
shemale lover 2011-12-16 6,688 Blowjob transformation tg
100%
Brazilian Discovery Chapter 3
Chapter 03: Partying in Copacabana On the Ipanema beach, Barbara and Joan were joined by Tereza and Consuela. The beach was less crowded than the Copacabana one. Tereza pulled down her shorts and her T-shirt to appear in a quite hot red bikini, an uplift bra that was supported only by a band arou... Read full Story
shemale lover 2012-08-25 3,605 Group Sex Cumshot oral sex Sex Toys
100%
Lustful Crossdresser by CDlishmis
As I think about the way I feel when I dress in women’s clothes. I become agitated with myself. I can’t stop. I couldn’t stop even if I wanted to, it is an addiction. The physi cal and mental transformation that I go through is ex... Read full Story
cdlishmis 2020-08-31 3,177 Crossdresser Blowjob gangbang Lingerie domination cum in mouth psychological
100%
First work day!
Having just graduated from college in Miami I took up fashion as a career! Impressed? In fact, I managed to land a job as a clerk in ready-made clothes shop. Sounds not as impressive as I’d like to have but that is just a beginning. You think there are no other interesting places in the whole ... Read full Story
shemale lover 2014-05-31 9,109 tranny asshole
100%
Whitney's Way
My arms were stretched over my head as I finished hanging the last sheet of drywall. Another step closer to the end of the two year process of renovating our first house, it was hard to conceal my sense of pride at turning a worthless wreck into the nicest place on the block. But as soon as I heard ... Read full Story
shemale lover 2012-11-18 8,579 Cumshot oral sex kissing
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 5,758 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
94%
Lady Blue
“Blue-eyed boys always get me in trouble,” she said in a sultry tone with an equally sultry smile. I smiled as I looked into those warm brown Latina eyes, so soft yet full of mischief. “I’ll be back in a sec guys,” said Tracy as she got up from the table and headed ... Read full Story
shemale lover 2014-11-13 4,469 cum oral massage
100%
Epiphany
My girlfriend Tonya was out of town for the weekend. She was meeting some college friends and going shopping and carousing in the city. A typical girls' weekend. I kissed her good bye at about 4:30 pm on Friday. We had become pretty close in the year that we had been dating. She was a cute blonde wi... Read full Story
shemale lover 2012-04-17 9,293 Stockings Cumshot oral sex crossdressing
90%
First Outdoor Fuck
Sat in my office with nothing to do was making me tired there was no customers to serve which was slowly driving me mad, what was worse was the hot weather outside which always makes me horny, knowing I had all my girly clothes in the boot of my car was making my cock twitch in my cheap nylon work t... Read full Story
shemale lover 2012-12-19 6,291 Crossdresser Outdoor ass fucking pantyhose heels
100%
TG Girlfriend moves in
Monday morning 6:00 am and I am just awakening, and I realize a naked body beside me has her arm around me, we are both naked. My wife Lydia is out of town to a seminar, and this adorable brunette perky tits and lovely eyebrows, beautiful lips slightly pink, sleeping beside me. Joanne and I had spen... Read full Story
Jon Paul 2022-01-18 5,145 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth