Sort by
Relevancy

Free Stories

100%
Jenny, Melissa and Me
I’m watching you on the screen, Jenny, as you pull down your pretty nylon panties with the floral prints and spread your legs. Your brunette hair hangs down around your lovely eighteen year old face, smiling as your labia open wide and you begin to rub your clitoris, all the while smiling, and... Read full Story
shemale lover 2012-10-28 2,856 anal Group Sex Fetish oral
100%
Amy The Tranny Part 2
I couldn't stop checking Amy out all through dinner. She was dressed in a skin tight mini skirt, her perky little tits standing out from her tiny frame, and long hairless legs cast in nylon fishnet stockings, and 6" stilettoe heels. I wasn't the only one gawking at her! Every guy and even some ... Read full Story
shemale lover 2012-01-11 2,694 shemales Fetish ass licking
100%
A Holiday Job
'Bye!' Paul stirred briefly in bed as his twin, Anne, called out as she dashed from their holiday apartment. Paul glanced at his watch; it would be a rush but she should make it to the airport in time for her flight back to England. They had been on holiday at a popular Mediterranean resort fo... Read full Story
shemale lover 2012-03-09 4,341 Fetish transformation crossdressing make up
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 24,626 Cumshot Blowjob fuck fingering big boobs
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 13,225 Cumshot Masturbation oral sex
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,952 Teen (18+)
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,958 torture extreme fiction bondage and discipline
100%
The Invitation
"You see, we have to come up with something that would be so embarrassing for you that there is no way that you would ever show those pictures of me to anyone, regardless of how d***k you got, or how horny you got or how pissed off at me you were,” Sally went on. “Something that wou... Read full Story
shemale lover 2012-03-20 6,654 Group Sex crossdressing feminization
50%
Transvestite father异装癖的父亲和儿子被农民工虐待
'migrant worker S, good at foul language and humiliation, SP, heavy hands, is it acceptable?' On the SM dating software, a message popped up. Migrant worker S. What the hell? I casually click on his information, 39Get 186 and 76, dynamic is full of handsome muscles, muddy shoes, a glimpse of gar... Read full Story
Oldslut Sissy 2024-08-21 2,415 Amateur Big Cock Asian Sex Toys Mature sissy chinese
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 13,195 transgender
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 9,734 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Retail Therapy
It began, as many of these stories do, with a pair of panties. I love lingerie as much as the next girl, but never overly indulge, as money was a little tight. My new husband Alexander and I had finally settled into our post-college lives and were reasonably well off, but had a plan to pay off colle... Read full Story
shemale lover 2012-08-31 4,198 Crossdresser Cumshot Blowjob jerking Lingerie
90%
Collette's Property
I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade ... Read full Story
shemale lover 2012-12-19 8,475 anal Crossdresser Blowjob domination ass fingering
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 8,478 transsexuals romance crossdressers
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 7,213 Creampie Big Cock ass fucking
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 31,817 strapon porn
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 9,068 Group Sex Cumshot oral sex assfucking
75%
Rebound
My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to... Read full Story
shemale lover 2011-11-25 6,615 anal Creampie oral
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 10,090 transgender toys bondage and discipline heavy
100%
Eve Quest
Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,... Read full Story
shemale lover 2012-04-21 6,861 domination oral sex transvestite
100%
Rachel and Chris
Part 1 : Rachel and the Ring Yesterday was clear with a light but chilling winter wind present to remind all that the bit of warmth in the sun would only last a couple of hours at best. I struggled between sweating and freezing as I worked to remove the winter street grime from my roadster. Top ... Read full Story
shemale lover 2012-04-10 5,045 Cumshot oral sex Sex Toys
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 14,499 Masturbation cum orgasm cumshots prostate
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 8,186 Crossdresser hardcore ass fucking cd
100%
Debbie Part 5
Debbie didn't wake up until her gag was wrenched from her jaws. Her hood, collar and earplugs had already been removed. "Wake up, shit-head," Mistress spat and slapped her face hard. Debbie came awake and noticed that all the straps holing her to the couch had also been removed. She felt a... Read full Story
shemale lover 2011-12-22 5,888 transgender toys bondage and discipline heavy
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 7,337 transsexuals erotica romance crossdressers
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 6,833 anal shemales Group Sex
83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 14,745 anal Blowjob black fiction
50%
A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
shemale lover 2012-06-03 11,726 shemale oral sex Interracial
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 18,588 Shemale Fucks Guy
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 5,678 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
100%
Secrets
Jon had invited me to spend another weekend at his place with another of his friends. I always find his friends to be interesting so I accepted. Jon had given me a garage door opener and a key to his home after my first visit. He met me as I parked my car in the garage. He was wearing his usual skim... Read full Story
shemale lover 2011-11-01 6,661 anal Blowjob transvestite
50%
Debbie Part 6
Debbie was awakened by someone holding a hand over her nose and mouth, so that she couldn't breathe. She struggled, weakly tossing her head before opening her eyes. She looked straight into the eyes of Dr. Jacobsen, smiling evilly down at her. He continued to hold her head so that she couldn't breat... Read full Story
shemale lover 2011-12-23 4,799 transgender toys bondage and discipline heavy
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 9,403 cum oral domination
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 5,710 anal Group Sex oral domination sissy
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 11,131 Masturbation Blowjob blonde ass fucking big boobs
100%
Vengeance is sweet
What a warm day. Really hot, perhaps even the camels fainted in the zoo because of the heat. The thermometer reached 35°C that day. At these temperatures people usually aren’t up to do anything. So did I, because I sat together with Claude in his front yard. We were both sitting on our bea... Read full Story
shemale lover 2011-09-04 4,953 anal shemales lesbian sex
100%
Debbie Part 8
Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... Read full Story
shemale lover 2011-12-23 7,849 transgender toys bondage and discipline heavy
57%
Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
shemale lover 2011-12-23 6,839 transgender toys bondage and discipline heavy
91%
A New Year's Resolution
I'm not gay (laughing), with that said, I have seen some very good looking, uh, guys. Okay, go ahead and laugh. You see, toward the end of this past summer (August 2011), my wife and I visited an old friend of mine in Pattaya, Chon Buri, Thailand. He's a former Navy Seal. I'm a former Army Ranger as... Read full Story
shemale lover 2012-04-16 8,081 anal sex cum oral sex
50%
Eric...a
There was no doubt that this was going to be my last baseball game in organized ball. I knew that after high school I would not get a chance to play anywhere else, save for the drunken beer league down the line. I was an average player who played for a small school. I played second base. We were los... Read full Story
shemale lover 2012-04-18 6,341 first time anal sex jerking off crossdressing
100%
The Bitch Bites Back
Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley. Pamela was in her mid forties and fighting a losing battle against t... Read full Story
shemale lover 2012-05-12 8,006 anal sex Cumshot oral sex wanking cum swallowing
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 9,006 Cumshot oral sex sissy
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 4,464 big dick shemale oral sex crossdressing
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 5,819 cum domination oral sex feminization
100%
Alexis Chapter 4
Thursday rolls around, and Mr. Hughes tells me to stay after class. As usual, he walks into the supply closet when all of the students have left, and I diligently follow him. I suck his cock for a little bit, and then he says that he wants to fuck me. I nod my head and stand up, looking him in the e... Read full Story
shemale lover 2012-10-06 4,051 Creampie ass fucking oral sex
58%
My dream Pt 1
This is my first story..... I am myself as Sydney and this is written with what i hope the person who falls for me thinks of.... __________________________________________________________________________________________________ It wasn't my idea to move to Phoenix; well it really was my choic... Read full Story
Sydney Sun Min 2017-12-26 32,906 sex toy Cumshot suck dildo oral
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,790 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 9,894 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
91%
First Meeting with Couple
Hi everyone, I actually went through with it and got together with the couple from the fetish party to experience my first sex and scene in real life. It didn't go as i had dreamed of; but, thinking that it would go like that was pretty naive on my part. To start with, i Must tell how cute I l... Read full Story
shemale lover 2014-08-13 5,723 first time shemales bdsm
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,644 cum massage shemale sex
66%
A Night Out To Remember Part 2
Decisions... decisions... we all make decisions everyday and most of them are simple easy decisions. Some may take hours, some take seconds and some are made before we even know it. Some decisions carefully planned and some have planning at all. Some decisions are between several choices and some ar... Read full Story
shemale lover 2012-04-20 3,299 anal sex Cumshot Sex Toys
100%
Bookstore Bound
My Master, ever the gentleman, held the car door open for me. I smiled at him as I turned to get out of the car. I made sure to spread my legs in a very unladylike manner, giving him a good peek up my short dress. He simply shook his head and took my arm. We made our way over to the entrance to the ... Read full Story
shemale lover 2012-08-02 5,769 cum oral sex cum swallowing face fucking
75%
Flowers in the Heart
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 10,960 anal tranny Cumshot oral
100%
When Curiosity Fills
I sat in alone in my office at 11:00 p.m. on a Thursday night in April, preparing an important motion in a multi-million dollar malpractice suit. After editing the final draft I sat back and took a deep breath. I was exhausted, and, oddly enough, pretty horny. The wife was out of town and somehow I ... Read full Story
shemale lover 2012-12-08 9,084 anal shemales cum
95%
Proud To Be A Sissy Chapter 8
I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how m... Read full Story
shemale lover 2012-12-24 9,768 Teen (18+) Crossdresser Uniform Lingerie domination
83%
A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... Read full Story
shemale lover 2011-12-06 12,203 Bareback cum ass fucking slave