Sort by
Relevancy

Free Stories

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 6,214 Shemale Fucks Guy Asian Guy Fucks Shemale rimming bottom ladyboys cum in mouth top Versatile
83%
My day after forced feminization - fetish
My typical day starts with getting dressed in one of my favorite outfits. Short minidress, thigh highs, thongs, a corset and 6 inch Stilettos. I started wearing a corset to get my waist tighter and transition too the perfect hourglass figure. After Breakfast typically one of my wife's friends stop... Read full Story
TRTRAIN 2023-04-22 5,271 solo Amateur Masturbation Fetish Ladyboy Lingerie domination Sex Toys Homemade
100%
It Started by Waxing and Ended Up Something Else
The Best sex I ever had? With a 29 year old female about 7 years ago, (2017) Her alleged name was Ashlee, How did I know her? For about 3 years I was paying for a total body etc. professional waxing, with Karen who had a business in Lincoln. People have not lived until they have gone through... Read full Story
Linda Tiffany Vista 2024-05-09 4,016 Crossdresser blonde Shemale and Girl domination Sex Toys small cock Homemade
0%
The orgy with a shemale
I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name w... Read full Story
shemale lover 2011-08-29 5,455 Big Tits asshole Big Cock
66%
Adventures of Shemale Sandra Part 2
Sandra thought about Jeff all through the next day. He had been her first, and she could still recall their experience as if it had happened only moments ago. She could feel his rough hands on her tender flesh; his sweat falling in beady drops on her soft belly; his stiffled grunts echoing in her ea... Read full Story
shemale lover 2011-09-03 4,630 sucking shemale nipples
66%
Showing Off For My Wife's Pleasure
There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my f... Read full Story
shemale lover 2011-10-25 5,605 anal asshole shemale
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,464 toys bondage and discipline chastity belt
50%
The Visit
A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... Read full Story
shemale lover 2012-01-26 8,580 Group Sex licking sucking pissing fucking
100%
Blushing Bride Chapter 4
Chapter Four: The Hen Party I've already told you all about the night a couple of days before my wedding, the night of my stag party, the night where I got to live out all my fantasies and play the blushing bride, dressing in my soon to be wife Gina's gorgeous white wedding dress and lingerie and... Read full Story
shemale lover 2012-07-21 4,146 big dick shemale oral sex crossdressing
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 5,668 Crossdresser Fetish Lingerie
40%
Kitten: A Pantyboy StoryKitten: A Pantyboy Story
It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first ... Read full Story
shemale lover 2012-09-10 7,307 Crossdresser fingering Sex Toys handjob 69
100%
Caught
Hiya my name is Kara Harris, my parents were really expecting another girl and had put the name on the birth certificate before I was born; I'm nineteen years old and stand at 5 foot 5 inches tall. I have never really looked like a boy with my curly back-length brown hair and my large almond-shap... Read full Story
shemale lover 2012-10-05 4,892 Cumshot sucking Sex Toys
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,950 anal Cumshot shemale oral
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 4,751 Fetish cum oral sex Sex Toys cum swallowing
72%
From Tomboy To Boy
Mike Flannigan is a wealthy man who, at the age of forty, could certainly afford to retire from his law firm with a lot of money to spend. He had always been the most driven person in his family. He was born in 1951 in Dallas and lived there for most of his life. His parents were a working-class cou... Read full Story
shemale lover 2012-12-03 4,446 anal sex sucking Creampie
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,488 sucking Fetish Uniform domination big boobs
71%
Creating Alyson
"Is it an acid?" Diana answered hesitantly. My snigger from the back of the room told her it wasn't. I knew people thought me arrogant, and a know-it-all, but as usual I couldn't resist. All year during the chemistry classes for the science course she was following, Diana had strug... Read full Story
shemale lover 2013-01-11 5,368 Crossdresser hardcore sucking Blowjob oral sex
87%
Story of Heather Chapter 1
So I have been struggling with who I am ever since I could remember. I guess the main point I'm trying to make is I was born a boy, but have always had the urge to be a girl. For years I have battled this and the growing hunger of letting this inner woman come out. As I have progressed through the y... Read full Story
shemale lover 2013-01-17 3,761 Teen (18+) Crossdresser Cumshot sucking Interracial
100%
Good Friends are the Best
This story takes place after I had been crossdressing and watching shemale porn for years. It all started out with me trying to avoid seeing men's cocks while watching porn so I tried lesbian porn and then found shemale fucking girls porn to be crazy sexy. After watching a lot of shemales fuck... Read full Story
Jinn.V23 2014-01-20 6,291 ass Crossdresser Amateur fuck cd
87%
smoking
Greg decided to go straight. I had to find a new place to live. A nice man, Pete, who I knew from the YMCA, offered me a place in his basement. He was going to rent it out. It was nice, full kitchen, bedroom, laundry room, living room and another space for anything I would need. His rent was che... Read full Story
cd4fun715 2019-01-08 3,049 Amateur
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 8,015 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
100%
Camming down the rabbit hole Ch3
Slowly stirring from my sleep, I stretched under the covers and a pleasant sensation spread across my torso, remembering what I was wearing when I went to bed I smiled at the caress of the fabric on my skin. It was a strangely comforting feeling, the pressure from the bra, panties and nightie felt l... Read full Story
Dani_does_Dallas 2021-08-18 5,480 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
My first TG lover
I first met Holli at the gymnasium of our apartment complex. Since it was around 6:00 am on a Sunday morning, I didn’t expect to see anyone that early. At first just like we all do, the customary good morning, small talk, and it usually stops there, but there was just something that drew my attentio... Read full Story
Jon Paul 2022-07-01 8,054 Amateur Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale
100%
Daddys Little Slut
I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... Read full Story
aishacox 2023-01-31 5,703 Crossdresser Cumshot Fetish Blowjob Latex
80%
Vicky Part 1
"Dear Sir, We recognize you as a person of discerning taste. We would therefore would like to invite you to a display we believe you would find most enjoyable." What followed was an address and a date, one week away. My name and address were correct, but I didn't have a clue what they w... Read full Story
shemale lover 2011-11-14 4,973 sucking cum fingering
100%
The Naked Day Wedding
I'd looked forward to this day with a feeling of excitement and also a certain amount of trepidation. Now the moment had arrived and it was all happening. I looked at my gorgeous bride Tina as we signed the register of marriage in the towns' registry office. Outside, I could hear the bustling ... Read full Story
shemale lover 2011-11-24 3,263 anal shemale strapon
100%
Headmistress' Favorite Sport Part 4
Over the next weeks Denise and the others settled into the routine, accepting their new life. Cindy did, as Mistress Hoffmeyer had predicted, break very easily and now she had been remolded as the slave-sissy her master wanted her to be, docile and obedient. Others needed more effort and others less... Read full Story
shemale lover 2011-12-12 7,758 torture toys bondage and discipline chastity belt
100%
Permanent Stay in Mastersville Part 4
My training was now reaching full speed and I was handling the maid's duties in the house, while at the same time spending a lot of time with sex training. Diane, on the other hand, was clearly reaching the end of her stay with Mistress. It was quit clear that a buyer would soon be found for her and... Read full Story
shemale lover 2012-01-08 4,701 toys bondage and discipline heavy reluctant
100%
The Boutique
Sharon had been working in the little boutique, called The Fabric of Temptation (a name that Sharon secretly thought was just a little corny), for almost four weeks now. She'd applied for a number of jobs for the summer vacation, wanting to make some more money than the allowance her parents gave he... Read full Story
shemale lover 2012-05-13 6,156 sucking transsexual deepthroating
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 8,789 Group Sex Cumshot oral sex assfucking
100%
I am Hannah!
It was soon my eighteenth birthday. Hi, my name is Robin! I'm a lonely, chubby guy. Let me tell you my story. The years passed on by and me and Mary grew fond of each other. We went to different schools but kept seeing each other. But to her I was no longer Robin. In her mind I was Hannah and sin... Read full Story
Lildbehr 2012-07-12 3,445 oral sex crossdressing feminization
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,455 sucking Fetish fucking sissy
100%
Porshe's Escapade Chapter 3
Hi all it's Porsche finally back and able to tell you about another escapade. My male half has been so busy lately with work and vacation etc. that Porsche just hasn't had time to play. So for my first free day in a long time I decided to be Porsche all day long. I got out of bed and droppe... Read full Story
shemale lover 2012-09-05 3,302 Crossdresser Blowjob Sex Toys double penetration
50%
Wife Converts Husband Chapter 2
We end up going to a big lingerie shop and buy several pairs of g-strings, booty shorts, bra's, corsets, suspender belts and stockings of all colours and styles, which Shelley thought would best suit me and a pair of breast forms to give me real looking breasts. We then went to a shoe shop and bough... Read full Story
shemale lover 2012-10-18 4,055 cum fingering oral sex Sex Toys
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,918 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
88%
Ivana Pushing Sissy's Limits
"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of... Read full Story
shemale lover 2013-03-19 6,911 Crossdresser Cumshot sucking Creampie ass fucking