Sort by
Relevancy

Free Stories

73%
My night with my Black Master
I posted on this site i would like to be a blackmans sissy,i did get a response from a guy who said he was looking for a white sissy to use i told him i was 55 and never done this before but i would love to be his sissy for a night,we arranged to meet at a holiday inn on the M6, we meet in the bar h... Read full Story
bigtranslover 2013-12-29 7,798 first time shemales interracial sex
100%
A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
shemale lover 2012-06-05 8,738 Group Sex Cumshot oral sex assfucking
87%
Taste of My Girlfriend's Dildo
I can't think of anything I'd rather be doing than sneaking into my girlfriend's wardrobe while she's out and trying on her lingerie. The moment she leaves the house, I head for her garter belts, bras and knickers. I don't have anything to put into her 36C bra cups, and my cock barely fits her p... Read full Story
shemale lover 2012-09-01 4,191 Stockings Crossdresser Cumshot Blowjob Sex Toys
100%
Dress Up
I don't know how to explain it. I am not gay although I may be passive bi. I have had sex with men, but not a lot and I have always been the one receiving, you know once a friend showed me a pack of pictures of his wife from fully dressed in conservative suit to complete nude with some action photos... Read full Story
shemale lover 2012-11-17 4,724 Fetish cum oral sex Sex Toys cum swallowing
81%
Tranny G's all Tranny Gang Bang
Chris had finally returned after a year overseas. During his leave he flew out to Phoenix and we would spend a few days in Las Vegas. We drove four hours and checked into the hotel. A year apart and we ripped our clothes off and fucked hard. We took a short nap and went for an early dinner. I told C... Read full Story
shemale lover 2013-03-05 7,880 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
80%
When the Boss found out
Id been working in a new office job for a few months, keeping my secret life just that from the others who worked there. Before going out one night to a cd and gay bar in the city I was working late, knowing I wouldn't have the time to be back home, dressed and back into the city I decided... Read full Story
sissychloe 2016-08-29 3,775 Crossdresser suck Blowjob cum sissy
83%
Gloryhole
It wasnt long after arriving before a cock slide through the glory hole for me to suck on, and what a cock, big thick & so suckable. I didnt need asking and was soon parting my lips and taking as much as i could in my mouth. The moans from the next cubicle seemed to indicate that it was more t... Read full Story
sissychloe 2016-08-29 10,186 Crossdresser Blowjob cum sissy gloryhole toilets
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,549 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 9,785 transgender toys bondage and discipline heavy
25%
Adult Bookstore Dancer
Adult Bookstore Fun At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make abou... Read full Story
shemale lover 2012-02-26 4,337 sucking Fetish cross dressing
85%
Becoming My Roomate's Wife
Him becoming my master started a year ago when we moved in as roommates – we are both in our mid 20's and had relationships break up at the same time (we were sharing apartments with our girl friends at the time). We have known each other for more than a decade and have no secrets from each ot... Read full Story
shemale lover 2012-04-01 9,011 Crossdresser anal sex domination oral sex
0%
Tara's Adventures
Part 1 I had met them on line. Marla 1st then her owner Mistress Olivia. We chatted for well over a year and had met for drinks. They knew of my submissive fem side and we had planned meetings on several occasions but things always developed that upset them. Then a period of time developed whe... Read full Story
shemale lover 2012-08-11 5,430 anal Group Sex oral domination sissy
100%
Such a whore
I finnaly made this happen a few days ago ! i have been crossdressing for as long as i can remember.I still remember when i snathed a pair of my cousins panties when i was young i dont know theres is just something about womens clothes that just intrigies me . Any way growing up i always masterbate... Read full Story
shemale lover 2013-05-31 5,630 Stockings hardcore Cumshot suck sucking jerking doggy style cd
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 5,128 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
72%
She fucked me so hard...
I was 22 at the time and really horny! I hadn't cum for a whole week... and I was saving it for something special. I was desperate to meet with a Crossdresser, was watching porn videos of big cocks deepthroating and anal fucking, but my favourites were Big cock shemales. Nothing would turn me on mor... Read full Story
shemale lover 2011-10-16 7,863 first time cum oral sex
100%
Debbie Part 2
There were no clocks and no windows in the dungeon, so Debbie (as she thought of herself after a long night of pain, lust and confused thoughts) couldn't really tell that it was morning. But she assumed it was morning when Mistress came back. Debbie's walk was still perfect even after walking around... Read full Story
shemale lover 2011-12-22 5,420 transgender toys bondage and discipline heavy
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,331 strapon porn
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 4,016 anal gay male Fetish
100%
Darling Nikki Part 2
Chapter 1 - The Morning After The next day, Nick awoke thinking it was just a really messed up dream. When he got out of bed and found that Samantha had unlocked and removed the dress, panties and shoes, but everything else was still on, he was pulled right back to reality. He looked in the mirro... Read full Story
shemale lover 2012-07-15 4,589 Cumshot oral sex sissy
100%
Demoted Chapter 1
Monday I had been working in this office for a couple years, I was a floor supervisor had my own office and a few people under me. It was very easy and never had any trouble at all. I am also a cross dresser and I didn't know it but my story starts with a page I had on the Internet. I checked my ... Read full Story
shemale lover 2012-08-13 5,636 Crossdresser Fetish Lingerie
90%
What Just Happened? Chapter 4
Chapter 04 -- I am no longer in control I looked at Beth and so did the pizza guy. The delivery guy started a discussion by saying, I do not want to offend you girls, but you are both very attractive and I see one of you has panties on because I can see them. So the other panties on the floor mus... Read full Story
shemale lover 2012-12-16 3,843 Cumshot sucking Fetish deepthroating kissing cd
33%
Sleazy Walking
I was bored one night, and began to email wanted ads on craigslist to see who was hosting in my area. I lived in spokane, wa at the time in the east central area, sorta behind the fred meyer. This night was boring, my friends had left a while ago with their girl friends, jealousy began to set in. I ... Read full Story
Ville Lohner 2014-05-15 3,116 Stockings Crossdresser Amateur suck Lingerie
95%
How I became a cute femboy CD part 2
The game of husband and wife Kevin and I played went on for a little over 2 more weeks before we decided to go even further, I say we but it was Kevin who seduced me into it. We got together in our game as much as we could and it was a lot. I would always dress for him in various outfits and my ... Read full Story
Cute_Femboy 2016-04-05 12,604 first time oral sex nipples crossdressing cd sissy
90%
Fortunate accident part 4
I reëntered the room clad in a g-strip and bra; I wore eye make up and lipstick with a long blue wig that covered my left eye with one of the bangs. I popped my hip and tried to lean seductively on the doorway --something I, admittedly, had not had a whole lot f practice with. She looked out at me a... Read full Story
Jenna_NB 2016-04-28 3,576 Crossdresser facial cock sucking strap-on sissy
66%
wishing
When I would get off the bus from after school activities, I would always walk through this truck stop on I-94 east of the Twin Cities. I would always look at the truckers parked for the night in the back. I always wondered what would happen if I brought my desires and fantasies to life for one of... Read full Story
cd4fun715 2019-01-08 3,054 Crossdresser Amateur
100%
Wild after-hours for a working... effeminate crossdresser
Left work after-hours, cross-dressed underneath w light lingerie & lots of colored little tattoos I draw myself over my hairless body. After drinking lots of spirits on my way home, arrived at my neighborhood park late at night & felt like wishing to be ..... badly abused! I got rid of the... Read full Story
Alexia Pikara 2011-09-07 4,375 Outdoor Bareback double penetration
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 6,741 shemales Fetish bdsm
60%
Aunt Cindy's Bizarre World
My name was Jim Rogers Jr. at one time. I was born and raised in a small town in a rural county in Oklahoma. My father James had been the pastor of the local Pentecostal Assembly of Jesus. Dad was what was known an ultra conservative hell fire and brimstone preacher. My mother's name was Allison. Sh... Read full Story
shemale lover 2011-12-02 10,350 taboo Fetish crossdressing sentimental erotic
50%
Caitlin and Mistress Vicky Chapter 2
I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.) Tak... Read full Story
shemale lover 2012-03-01 3,618 Fetish fuck domination oral sex
100%
Danny bCUMS Danielle
Danny left Dr. Tina’s office as Danielle, dressed in a short summer skirt that showed off his smooth legs and small girlish breasts. Sara was very happy holding Danielle’s hand as they strolled to the car. Danielle went to the passenger side, something HE never did, and got in. Sara hopp... Read full Story
shemale lover 2012-06-20 4,060 Crossdresser Group Sex Cumshot jerking off facefucking
100%
A Slut is Born Chapter 2
The week went by slowly as I digested what Jim had done to me last Saturday. As I walked around school, I found myself looking at people differently, wondering if any of them had ever been treated the way I had. This would always bring the details of what Jim had done to my mind and my cock would im... Read full Story
shemale lover 2012-06-27 5,749 Group Sex Cumshot Blowjob
100%
Fantasy to Reality Chapter 2
I faded in and out of consciousness My mind was pulsating from the excitement of a glorious dream, it involved a sissy kneeling subservient at the feet of her master, a single drop of cum dripped from her bottom lip and landed in the small puddle on the floor. The sissy's eyes looked up at the re... Read full Story
shemale lover 2012-07-02 3,289 Cumshot oral sex crossdressing
90%
Young Crossdress, Meets His Daddy
Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very ... Read full Story
shemale lover 2012-08-17 4,695 anal Crossdresser Cumshot Fetish oral domination
100%
My Wonderful Secret Chapter 2
I felt like I was going to explode inside. Such was the anxiety, excitement, fear, horror, and arousal I was experiencing. I had no one to talk about it with. I had no one to tell that I had been caught dressed as a girl. I had no one to share the secret that Mark had taken me home and treated me li... Read full Story
shemale lover 2012-09-09 3,851 Stockings Crossdresser Cumshot Masturbation heels
100%
Discovering Mistress Sarah's World Part 7
Chapter 18 A Life Changing Decision Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom.... Read full Story
shemale lover 2012-10-03 5,577 cum domination oral sex feminization
100%
Property To Be Pimped
It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really d... Read full Story
shemale lover 2013-01-17 7,528 Stockings Crossdresser sucking dildo Interracial
96%
CD Jinn Caught
Lately I have been having great times with one of my roommates who found me out and found he really enjoyed being with me when I am dressed. However before any of this happened I had met a guy through a friend on the football team at my college and had a couple great times with him while I was dres... Read full Story
Jinn.V23 2014-05-07 5,695 sex toy Crossdresser Cumshot suck threesome
100%
MY First Time with a non-binary/cross-dresser
After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... Read full Story
ghostpeople 2019-03-12 7,361 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,837 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
75%
The journey down the Rabbit Hole...
Nearly 30 years, living a double life. Sneaking around on two Xwives, several girlfriends, all to play with men.Play,and play and play. Responding to personal adds in the paper at first, then I found the Bath House. Wow, to a closeted homophobic acting oilfield lifestyle kind of guy, who could hide ... Read full Story
badbadboi667 2020-11-24 3,466 Crossdresser Amateur Group Sex Cumshot Outdoor Bareback Blowjob Big Cock gangbang domination Homemade Ass to Mouth
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 5,123 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
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 5,297 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
100%
Marilyn: Going Your Way
"Oh yes…eat me…ooh yeah…" Marilyn was laying on one side, watching her sister Sharilynn get gently eaten by Kat. Marilyn herself was bottomless, letting her limp dick hang down to recover from soreness. Yes, it was one of those weekend afternoons that stretched into... Read full Story
shemale lover 2011-11-08 3,645 sucking orgasm nipples
71%
Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
shemale lover 2011-12-02 12,694 taboo Fetish crossdressing erotic encounters
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 6,937 Creampie Big Cock ass fucking
50%
Polish Maid
'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, l... Read full Story
shemale lover 2012-09-01 5,021 Stockings Crossdresser Cumshot sucking heels
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,948 Crossdresser Cumshot Masturbation Lingerie heels
71%
Birthday Present Part 1
Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all abo... Read full Story
shemale lover 2013-01-18 11,575 hardcore sucking Blowjob Lingerie ass fucking
86%
My first time as a Femboy CD
My name is Nick aka. Nicole. I am a 20 year old gay femboy crossdresser and this is a little story of how I started dressing to become Nicole and my first sexual experience besides masturbation. I grew up living in an apartment complex with my mother and sister, who was 2 years older than me. M... Read full Story
Nicole_femboyCD 2014-12-03 191,764 first time Crossdresser suck Blowjob oral cd
69%
Motel Blackout
I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people. After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my spe... Read full Story
browncherrygurl 2017-05-25 18,382 anal Crossdresser ass fucking sissy forced
78%
Cara's First Time
Cara's First Time This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in... Read full Story
Emma W 2017-07-05 30,394 Crossdresser Amateur Bareback
84%
Emily's welcome
Since embracing the feminine me I’ve been on a bit of a shopping spree, it’s tough to be a gurl who hasn’t had anything really nice to wear for so long. In particular I love to buy pretty panties which keep my clitty nicely in place, but also rub up against my pussy as I walk – with nobody any the ... Read full Story
EmilyTG 2019-07-04 5,893 Crossdresser Group Sex Cumshot threesome Blowjob
100%
My favorite fuck part 1
Your responses and views have been a desirable response and encouragement for future stories. I’m just a guy, who wishes to be a girl, wanting to be seen and accepted as a female. So Thank you. I’m hoping to make more stories, and more to those willing to see me, and accept me. Much love :) Y... Read full Story
Mistysis 2020-11-02 3,098 Stockings Small Tits Crossdresser Guy Fucks Shemale
100%
my journey down the rabbit hole
The bathhouse was busy tonite, there were at least 20 or more men there when I got in , I paid for my room and walked in past the heavy buzzer controlled black steel door, it slammed tight behind me. casting a cool draft of air that trailed down the small of my back and fluttered over my enama clean... Read full Story
badbadboi667 2020-12-23 6,188 Crossdresser Amateur Group Sex gangbang Interracial Ass to Mouth
100%
First Date With Daddy
My Dream Date. It hasn't happened yet, but a girl can hope, this story is very short story based on my fantasy's. It was Sunday night and I had my first date lined up with daddy. We hadn't met, but we had spoken online at depth and exchanged numbers. I had sent him a couple of pic... Read full Story
SEXYBADGIRL 2023-03-17 5,260 Crossdresser Bareback Creampie domination
57%
Nicks Shemale Experience
Nick had discovered he had a thing for shemales 4 months ago after stumbling across some pictures on the Internet of a really hot ladyboy from a porn link site. This sort of thing had never turned nick on before but looking at pictures of the small-breasted brunette really made his dick hard. It did... Read full Story
shemale lover 2011-08-22 4,040 anal Fetish oral