Sort by
Relevancy

Free Stories

100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,452 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
50%
Womanly experience 8 - forest punishment
So we were walking through the forest one day. My father was out fishing and looking for a good spot next to the river while I lingered behind him. That day I wore Dr. Marten's boots, black nylons, a black thong that was more like a string, a short black skirt, no bra (had smaller tits back then), a... Read full Story
shemale lover 2014-09-25 4,412 shemales Masturbation bdsm
100%
Eve Quest Part 2
Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed s... Read full Story
shemale lover 2012-04-21 4,544 bdsm domination transvestite
80%
Office Policy
“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... Read full Story
shemale lover 2012-08-30 8,889 anal ass sucking threesome tits fingering sex blondie
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 8,954 anal Cumshot shemale oral
75%
Kidnapped (Adult Fiction)
Kidnapped I remember being normal. I was a young man in my 20's living in my parent's house struggling to get by. I was online more than I probably should have, but it was an escape from the harsh reality of my life. I didn't feel fulfilled or like a success, I felt like a failure on many differe... Read full Story
Vennom 2019-06-17 25,103 Fetish transformation fiction pov mind control drug interaction mind mindfuck change
100%
Adventures of Shemale Sandra Part 1
His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He a... Read full Story
shemale lover 2011-09-02 3,945 anal sex asshole cum
75%
Encyclopedia Erotica By The Fan
It was a normal-looking enough place. A small town in California. Looking at it, no one would ever guess it sat on the hellmouth. The Mouth of Hell. A portal to a multitude of dimensions filled with horrors and wonders. Many things came to the Hellmouth, drawn by its power. Vampires. Demons. Mon... Read full Story
shemale lover 2011-10-19 4,665 asshole orgy Sex Toys
100%
Alexis Season Part 2
But it wasn't her dick that was bothering her, really; it was the loneliness. Alexis and John had been going out for two months now, but they'd only gotten to first base and lingered there. No matter how many time he told her that he didn't mind that she had a penis, he simply refused to go any furt... Read full Story
shemale lover 2011-11-27 3,237 Masturbation massage softcore
100%
Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... Read full Story
shemale lover 2012-04-22 6,380 anal sex Creampie blonde shemale
0%
P.A. for a Day
The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders. As he drove up to the garage he mused about t... Read full Story
shemale lover 2012-09-05 6,184 Crossdresser Masturbation Latex Sex Toys heels
100%
Doggy Style
"OK, which exit is it?" Trish was driving with Penelope in the passenger seat up front. Meredith sat in the back behind Trish's seat with Angela behind Penelope. The quarter were sisters in a sorority attending an annual Alpha Phi event together. Every year different chapters across Sou... Read full Story
shemale lover 2012-10-17 5,337 swallowing crossdressing sucking off
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 119,653 hardcore Cumshot sucking bdsm domination
66%
TO BE OR NOT TO BE – PART 5
TO BE OR NOT TO BE – PART 5 by Spanky de Bautumn Part 4. Sunny made a life changing decision and in the process becomes better acquainted with Mark. On Monday, I met Mel and Shari at the theater at ten to run lines. I was confident that I knew my part for the first act. My concern was with m... Read full Story
SpankydeBautumn 2021-02-24 2,442 Crossdresser Cumshot Masturbation Blowjob Big Cock Lingerie Interracial
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 5,488 Stockings Crossdresser solo Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade
100%
Little cock convention
They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... Read full Story
shemale lover 2014-07-07 7,325 shemales hardcore sex humor
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,965 Stockings shemale oral sex bisexual
50%
Old Folks
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
shemale lover 2012-01-10 8,254 transsexuals romance crossdressers
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 5,168 sucking fingering Guy Fucks Shemale
100%
Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
shemale lover 2012-11-26 7,483 Fetish cock sucking crossdressing
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 10,869 Masturbation Blowjob blonde ass fucking big boobs
64%
Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... Read full Story
sach 2015-11-16 7,638 Big Cock ass licking redhead rimming Shemale on Guy
50%
Twisted
"Baby, are you sure this is the place?" Eve squealed a bit too loudly, her voice both high-pitched and thick from the third Cosmopolitan. "This looks so, I don't know; fancy-shmancy for a full on mix-it-up ladyboy bar. I know, I know, this is South Beach and everything here is la-de-d... Read full Story
shemale lover 2011-10-31 5,122 shemales Big Tits fingering oral sex
100%
Alpha Gamma's Secret Part 2
-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. ... Read full Story
shemale lover 2011-11-02 3,619 anal sex Masturbation shemale
80%
Alpha Gamma's Secret Part 3
-7- "This has been an important and exciting year for our sorority," said Jessie, House President, to the assembled sisters of the Northeastern University chapter of Alpha Gamma Tran. Today was a very special day. It was the annual Commencement Ceremony which marked a successful en... Read full Story
shemale lover 2011-11-03 3,953 transsexual orgasm ass licking
0%
Lady Denisa's Gang Banged
The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... Read full Story
shemale lover 2011-11-22 4,674 shemale oral orgasm
66%
Candy Pink Part 2
Chapter 4 My parents had a letter shortly after from the headmaster Mr. James Allen. I was to head out to CA before the start of winter term to get settled into the dorms and go through orientation. The letter said I should be there no later than December 1st and that they would arrange for me to... Read full Story
shemale lover 2011-12-08 4,644 taboo Fetish crossdressing
100%
Being Twins
I knew something wasn't quite right but I couldn't be sure. My life for the past 10 years with my wife Jane was great. My name is Richard. Jane was 5'8", 120 pounds, lean trim body, 38D breasts, beautiful blonde hair and stunning features. I was 5'9", 148 pounds, and little chest or body h... Read full Story
shemale lover 2011-12-19 5,666 hardcore erotic encounters fantastic
100%
Eve Quest Part 4
Chapter 16 Monday morning I was told to wear my red panties, bra and ribbon; my white collar, bracelets and heels and a red sleeveless dress. Sheila and Jenny ate breakfast, got dressed and loaded me in the car. They dropped me off in front of the beauty parlor and Jenny said. "If Hilda f... Read full Story
shemale lover 2012-04-21 4,326 anal sex domination oral sex transvestite
60%
The Clinic
I got out of my cab and looked up at the Clinic. It was a small, nondescript hospital. I was still pretty nervous about this treatment since I wasn't even sure of the details. But it was either this or go under the knife. This problem had to be dealt with. I picked up my bag and went into the lobby.... Read full Story
shemale lover 2012-05-02 6,174 Cumshot Big Cock jerking off oral sex cum swallowing
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 4,156 big dick shemale oral sex crossdressing
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,258 Fetish crossdressing feminization
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 5,440 shemale gangbang facial
100%
The Tranny Shocker
Tammy, my step daughter and I had not seen each other for a while and she called me suggesting that we meet for a drink. Naturally, I agreed. She suggested a gay bar near her home and we agreed that 7pm would be good. Tammy is a lesbian who is in a relationship with a beautiful, tall, sexy blond ... Read full Story
shemale lover 2012-04-23 3,754 anal sex Cumshot oral sex cum swallowing
100%
Serving Waitress
This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side. The story begins….. My wife, Susan, ... Read full Story
shemale lover 2012-08-28 4,997 anal sex Cumshot Creampie oral sex
100%
R Is for Rita
After my debts began to mount, college fees and all that, one of my mates from Brum suggested I try to earn a little extra cash. I was surprised when he told me how. He said he'd done it and ended up with a couple of hundred extra most weeks, sometimes just for an evening's work. "It's easy,... Read full Story
shemale lover 2012-09-05 5,526 Stockings Big Tits Masturbation Big Cock Mature
33%
Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
the greatest liar 2023-07-19 4,358 anal Bareback Creampie Ebony Guy Fucks Shemale post-op celebrity post op sex
100%
Bimbo Bombshell - Chapters 1-2-3
Bimbo Bombshell - Chapter One: Singled Out! Even though it was Friday, the bar wasn't particularly crowded that night. I never knew what hit me. This Gorgeous Blonde bombshell, starts flirting with me right a my table. I found myself wondering why this glamorous beauty, had chosen me. I was... Read full Story
Hardrock51Fifty 2024-06-23 6,736 Stockings Big Tits Shemale Fucks Guy Fetish Blowjob blonde domination Guy Fucks Shemale blonde shemale PDA Public Displays of Affection
97%
Shemale Runner
This is based on a real life experience and is about consenting adults engaging in sexual activities, if you are offended by such themes as shemales then do not read on any further. I try to stay fit, I run every day after work for an hour. There is an old dirt track walking path that links fa... Read full Story
shemale lover 2011-09-11 9,539 anal facial oral sex
50%
Sex with Shonda
I'm a workaholic by nature. I love my job but that's not why I work so much. I work long hours simply because when I get home I don't quite have anything productive to do. I just sit down in front of the television or I chat over the internet. Life at home is dull so the best solution seems to be en... Read full Story
shemale lover 2011-09-18 4,235 Blowjob fingering handjob
94%
The Babysitter's Secret
The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated... Read full Story
shemale lover 2011-10-24 21,429 Blowjob perky tits handjob titfuck
100%
A Close Encounter of the...
Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a... Read full Story
shemale lover 2011-11-13 5,227 Cumshot Blowjob massage
83%
Tilted Kilt Chapter 4
Like most mornings after a late shift at the Tilted Kilt, I awake around 11 am and lay in bed as the day comes into focus. The sheets felt cool on my nude body and I realized my roommate, Shari, had left the air conditioner on before she left for work. It's Summer in San Diego and the days of late h... Read full Story
shemale lover 2012-01-25 3,803 Cumshot sucking transsexual fucking
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,986 Stockings anal sex Fetish Interracial sissy
60%
A Sissy Boy is Made
By any measuring stick Greg Martin was a wimp, and a very submissive wimp at that. His wife of 14 years, Jaclyn, had discovered this even before the two of them were married. Actually, Jaclyn wouldn't have taken a second look at Greg, as most women didn't, had it not been for his submissive nature. ... Read full Story
shemale lover 2012-06-15 8,708 Cumshot oral sex sissy
100%
Only Once
She looked as rich and a chocolate bar and I'm sure she came with nuts, by the looks of guy who seems to walk one step behind and just to side of traffic. We had exchanged pleasantries a few days ago at an art show of a friend of mine. There she was with a diamond the size of a dime and a neck lace ... Read full Story
shemale lover 2012-09-03 3,455 Cumshot Masturbation Blowjob Big Cock heels
100%
Amazon Archipelago
On the northern end of Stuart Island, in the far corner of the San Juan Islands in Washington State, an old lighthouse guards the broad, deep channel between the United States and Canada. No longer manned, the building and light tower stand empty now, replaced by a soulless but efficient solar-power... Read full Story
shemale lover 2012-10-24 5,614 cum ass licking oral sex
100%
Angel Chapter 2
Angel Jones stepped off the train and hoped she was in the right place. It was noisy and confusing in the terminal, a far cry from the relatively quiet station in her home town where she had boarded the train that morning. One hand clutched a small suitcase that contained her makeup and clean linger... Read full Story
shemale lover 2012-11-30 4,466 oral sex tgirl feminization
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,432 hardcore sucking ass fucking Guy Fucks Shemale
88%
Becoming Lisa
From when I was as young as 9, smooth and long blonde hair, I was always dressing in my older sister's panties and bra, panty hose. My breasts were kinda girlish and i had long nipples that would get hard when I played with them. I was older now, but still only had a small 4 inch cock when it was ha... Read full Story
shemale lover 2013-08-09 13,251 Crossdresser Masturbation Fetish Lingerie kissing
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 15,655 first time ass Cumshot suck cd sissy make up
50%
There is love, but war
All characters in this story are eighteen years of age or older.* *The following story is inspired by Miss Evie Hyde's "Slut-Box Challenge" story. The following is written with permission from her to use her premise with my own characters and situation* Billy checked his phone when he got th... Read full Story
ASSEaster5678 2019-07-04 3,722 Guy Fucks Shemale bullies
80%
Transsexual Savage
John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... Read full Story
Anal Orgasm 2020-07-10 6,528 Big Tits Outdoor Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Guy Fucks Shemale
66%
Cock Sucking Jail Whore
I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with... Read full Story
shemale lover 2011-09-17 4,659 Cumshot asshole oral sex
50%
My First Time Out Part 4
It was Sunday morning at eight o’clock when the phone rang. Shayna’s eyes felt like they were glued shut but managed to answer the phone on the third ring. “Morning,” said Shayna as she was still half-asleep. “Good morning Shayna. This is the Bell Captain calling.... Read full Story
shemale lover 2011-10-18 4,710 cum oral facial deep throat fucking
81%
Rebecca's Secret
-1- The hour was growing late as I looked around the cozy living room. Six of my friends were sitting in various places, in various positions, all watching some late night horror movie on the television. There was a feeling of general contentment. We had arrived at the house several hours earlier... Read full Story
shemale lover 2011-10-19 5,431 Cumshot shemale oral sex