Sort by
Relevancy

Free Stories

85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 7,932 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
87%
The Hotel Part 1
I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days. Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, fucked fem, huge dildos, and giant buttplugs are just a few of my fetishe... Read full Story
shemale lover 2012-02-11 6,317 Fetish cum domination Sex Toys
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 7,863 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,664 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
72%
Becoming My Wife's Wife
"Baby, you know how much I love you. There's just something missing that I feel like I need in my sex life." My stomach turned as soon as I heard Sherry say those words. I remember it like it was five minutes ago. We had just finished having unbelievable sex and she was sitting naked on... Read full Story
shemale lover 2012-04-01 21,290 cum fuck Sex Toys
68%
How I became a sissy
So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write a... Read full Story
shemale lover 2012-07-30 7,413 Creampie oral domination Sex Toys
100%
Alexis Chapter 2
When I open the front door to my house, I'm already hard. I'm going to be home alone for an entire night, and I have a lot of things planned. I toss my backpack and jacket onto the couch, and by the time I reach my room I already have my shirt off. I let my pants drop to the floor and pull off th... Read full Story
shemale lover 2012-10-06 4,896 Creampie transformation dildo Sex Toys crossdressing
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 3,109 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
An Odd Encounter
I met her on one of those dating sites. Well, when I say dating site I mean one of the many that caters to people looking for random hookups. I don't know exactly what I was looking for at the time. I guess it was just that it had been a while and I was looking for some fun, but she was hot, so it d... Read full Story
shemale lover 2011-10-09 4,373 facial domination Sex Toys
100%
A Job in the Theatre Chapter 19
"Be a dear and get that bag from the car," Paula winked. "Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so obscene with ... Read full Story
shemale lover 2012-03-15 3,326 anal sex shemale stroking shaving
100%
Dress Up For The Girls Next Door
I’m just your ordinary guy, you know the type, women love me, I’m an electrician by trade and there isn’t a single or married woman out there who hasn’t asked me, “Can you really install my ceiling fan for me.” 6’, 200 lbs, brown hair, blue eyes, I keep acti... Read full Story
shemale lover 2012-11-18 4,060 Fetish jerking oral domination Sex Toys swallowing tit licking
60%
My Shemale Girlfriends My Mistresses
Sorry i haven't been writing stories, I've been a full time slave of multiple mistresses the past year. if you read any of my other stories, you'd know my beautiful girlfriend/mistress Christy, who is my main mistress, Brittany, her friend from Denmark, is my secondary mistress and has moved in with... Read full Story
shemale lover 2013-12-08 4,734 Cumshot bdsm gangbang domination Sex Toys
100%
Fulfilling A Girl's Male Fantasy
"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at ho... Read full Story
shemale lover 2012-04-04 3,936 orgasm fingering oral sex Sex Toys
100%
Head Cheerleader Mikki
At 18 i was your average kid in high school. Decent grades played sports. I was on the volleyball and swim teams. I was about 5'7" 145 lbs and in good shape. My girlfriend was 19 and used to be the head cheerleader at our school. She was gorgeous. Her names Donna and she was a freak when it ca... Read full Story
shemale lover 2012-06-08 3,749 Cumshot oral sex Sex Toys crossdressing
100%
Head cheerleader Mikki
At 16 i was your average kid in high school. Decent grades played sports. I was on the volleyball and swim teams. I was about 5'7" 130 lbs and in good shape. My girlfriend  was 19 and used to be the head cheerleader at our school. She was gorgeous. Her names Donna and she was a freak when ... Read full Story
Mikki A. 2012-06-18 4,371 anal Cumshot oral Sex Toys cd
100%
How I Became Vanessa Chapter 1
PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husba... Read full Story
shemale lover 2012-10-31 4,040 anal Cumshot Masturbation Sex Toys
50%
trans=demic
Trans-demic Chinese Flu Sam Wong read the email from Josh Epstein, the partner in charge of the fiendishly complicated real estate deal that had consumed the last three months of their lives. “You’re going to have to close this deal without me. I’m sick as a dog, and my wife just called an ambu... Read full Story
the greatest liar 2024-09-09 1,528 anal Small Tits Bareback Creampie Asian Guy Fucks Shemale small cock Ass to Mouth cum in mouth
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 4,359 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,521 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
Bangkok Bar Girl
I recently attended an international trade conference in Bangkok. The manager of our small office there, a big, ruddy-faced 50-something American called Mac, took me under his wing. (I'm 32 by the way, and married.) Before I left for the conference my colleagues in London wound me up mightily about ... Read full Story
shemale lover 2012-02-11 4,735 anal sex Ladyboy Sex Toys
81%
A LadyBoy For My Wife
I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... Read full Story
shemale lover 2012-06-23 11,568 Group Sex Masturbation shemale Ebony facial
78%
My Mom the Whore
Since junior high I love the way women clothes look and feel. Sometimes after school I would wear my mom panties and bras I didn't think nothing odd that all my mom underwear where a bit sexy and revealing, but I was a dumb kid who started his life in cross-dressing. Not into several years ... Read full Story
paulinacock 2019-07-17 10,952 Crossdresser Amateur Fetish transformation transsexual Ladyboy tgirl femdom crossdressing transgender feminization tg sexy Tranvestite girly MtF FEMINIZED transgirl sissified womanhood janegirl emasculation tgcaptions emasculate demasculinize
75%
Aunt trip
In 2013, after almost three years of service in Afghanistan, George Madsen, a gay Royal Navy communications petty officer, retired. His experience in the distant deserts had left an indelible mark, the memories of friends lost and challenges faced still burned vividly in his mind. Coming home was n... Read full Story
Rebba 2024-04-25 3,754 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,824 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
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 9,491 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
90%
Sister fucks Cross-dresser brother
James pulled his cock out of my pussy and scooted across the bed to my face. He aimed his blowhole for my mouth. "Don't get any on the pillow," I said. He didn't seem to hear. James hunched over. His eyes narrowed. He stroked his Johnson. The jizz flew. I opened my mouth and closed my eyes.... Read full Story
ASSEaster5678 2018-09-14 10,853 Ladyboy Sister and Ts Brother
100%
Danielle's First Time
Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... Read full Story
shemale lover 2012-02-03 5,797 cum dildo fingering
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 9,088 Crossdresser anal sex domination oral sex
100%
Discovering Mistress Sarah's World Part 6
Chapter 15 Joe's first 'female' public appearance as Josie was approaching fast. He was nervous about it. Fortunately Mistress Sarah had kept him busy most of the day so his mind was distracted. Shortly after his mind blowing masturbation session with her in the morning, she left to run errands a... Read full Story
shemale lover 2012-10-03 4,441 first time domination Sex Toys
100%
The Birthday Gift
I wasn't really looking forward to my 30th birthday. It's not that I was worried about getting old. Trust me, I'm not one of those guys who go looking for new gray hairs every week. Besides, I was plenty happy with my body at the time. I stood about 6' 2" and had a pretty muscular build. I wasn... Read full Story
beedoubleuthree 2011-10-21 7,074 anal threesome Blowjob cum strapon
100%
Unconditional Love Chapter 8
After a two' hour nap, Alison and I awoke and the first thing we did was make our way to the bathroom to freshen up. I started up the hot water and climbed into the shower and' once she finished relieving her bladder Allie climbed in with me under the hot water and we embraced each other. We kiss... Read full Story
shemale lover 2013-02-04 6,590 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Best of Both Worlds
Keith, 37, and Linda, 35, are very liberal people. Both enjoy sex although Keith had bi-sexual fantasies, he would never act on them, but also thought his wife was maybe a little shy and too submissive. Keith was a fairly attractive man, but his wife was still gorgeous at her age. With her long b... Read full Story
shemale lover 2012-05-09 4,249 anal sex threesome Blowjob Sex Toys
100%
Discovering Amber Chapter 3
There have been very few times in my life I have been terrified and today was definitely the tops on that list. Ms drove us to the mall and as I watched she walked around the front of the car and opened the door for me. I looked up to see her hand extended toward me. "Practice getting out li... Read full Story
shemale lover 2012-09-28 4,368 sucking Fetish domination Sex Toys
100%
Emergence of Josette
It was a few years ago when I admitted to my wife that I love dressing in women's clothing. It was after she found a stash of some of my panties. They weren't her size, so it was an immediate red flag for her. She didn't immediately believe me. So I gave her an impromptu fashion show. She seemed unc... Read full Story
shemale lover 2013-01-22 5,026 hardcore Cumshot threesome ass fucking Sex Toys
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 8,826 Group Sex Cumshot oral sex assfucking
87%
Threesome for Desi
After months of looking for someone to join us for a threesome, we finally found someone and he is coming over tonight. We are all going to meet at your place so I get over there right after work to get ready. We both take a shower and get dressed before he arrives. We sit on the couch together as w... Read full Story
b0099b 2016-04-27 5,273 anal threesome cd Desi
85%
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 5,349 solo Amateur Masturbation Fetish Ladyboy Lingerie domination Sex Toys Homemade
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 7,630 transgender toys bondage and discipline heavy
100%
The Birthday Gift
I wasn't really looking forward to my 25th birthday. It's not that I was worried about getting old. Trust me, I'm not one of those guys who go looking for new gray hairs every week. Besides, I was pretty damn happy with my body at the time. I stood about 6' 2" and had a pretty muscular build. I... Read full Story
shemale lover 2011-12-29 5,068 cum transgender bondage and discipline
100%
A Strange Affair
"I think you'd better come in," said the blonde-haired woman. She opened the door to the apartment fully, and stood aside as I walked through the door. She was attractive enough -- it was hard to see why her husband would want to cheat on her. She was very tall, and made taller by her b... Read full Story
shemale lover 2012-07-01 5,007 Cumshot Fetish Sex Toys crossdressing
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 12,948 Cumshot Masturbation oral sex
100%
Working with Trista Chapter 2
Day 3: That morning I was awakened as my phone rang; Trista was calling me telling me it was time to get up. She said that she would be over shortly. I hoped it was to let me out of the chastity device. That moment couldn't come soon enough, and neither could I! A few minutes later Trista knoc... Read full Story
shemale lover 2012-09-24 4,019 sucking cum Sex Toys
100%
Reshooting the Scene, Chapter 1
I have been a porn aficionado since I was a teenager. My first dabblings were with Hustler magazine and a *very* hardcore mini-novel called “Her Busted Asshole,” which told the raunchy story of Ginny Cummings’ sexual coming of age. In addition to the very graphic story, it had full color glossy p... Read full Story
Lovelace 2021-06-07 4,906 Bareback threesome Blowjob blonde Big Cock Sex Toys Ass to Mouth
75%
GRANNY TRANNY'S HOUSE of SIN
It all began after my husband died and I was living alone. I decided to adopt a family and corrupt their minds. You see, I'm an ex SHEMALE PORN STAR and I like to live a wild life and I figured after my husband died I should relive my wild life and be happy. I reached over for my GOLD METAL MESH CIG... Read full Story
BITCHGURLvr 2024-11-09 8,209 shemale cum sex Cigarettes
50%
The club
"Okay ladies," Missy said to her guests, "relax and get ready because I have a very special treat for today's meeting!" "What is it?" and excited Jayne asked while removing her sweat shirt and jeans. "Now you know better than to than that" Missy replied with a... Read full Story
shemale lover 2012-05-03 4,882 Group Sex Cumshot Ladyboy fingering Sex Toys
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 11,485 shemale oral sex Interracial
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 6,047 anal sex Cumshot oral sex rimjob
90%
In Hose and Heels for Daddy
It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and... Read full Story
shemale lover 2012-09-30 7,664 Fetish jerking crossdressing
100%
Womanhood for Jenny
The muted alarm-clock brought jenny awake instantly. She reached over to shut it off. Being ever so careful not to disturb Master, she slipped out of bed and gazed lovingly at the sleeping man. From their earliest intimacy, He had accepted her completely as a woman, His woman, not a trans-gendered m... Read full Story
shemale lover 2012-10-07 6,141 hardcore Sex Toys tg
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 4,073 cum fingering oral sex Sex Toys
100%
Amber Becomes a Reality
Over the years I had fantasized more and more about kinky sex. At first it was just a little kinky but after surfing the Internet I have wanted to try almost anything and everything. The problem was I had been dating Jen. She wonderful and beautiful but she was not kinky at all. I would have loved t... Read full Story
shemale lover 2012-10-25 4,594 sucking cum swallowing massage
70%
Play Day for Sara
It doesn’t happen often, but an opportunity opened up for me recently to take a day off to get a hotel room, get dressed, and entertain men. So I took it. When I discovered I would have this day to myself the previous week, I ran the following ad on craigslist: “Get ready boys – t4m super horny... Read full Story
saralovescd 2017-05-02 6,657 anal sex oral sex crossdressing Craigslist hotel room tag team
82%
My Sex Fantasy
I want to be raped. I need a forceful guy to fuck me when I’m completely unable to stop him. I’m a crossdresser who is an anal virgin, and for years I’ve wanted to lose it, but never had the courage. I’ve dressed and cammed and come so close to being fucked, but always wussed... Read full Story
shemale lover 2011-11-11 19,159 humiliation fantasies
75%
Erotic Cummings
For the last few years, my ex-wife and I have engaged in a torrid affair. You see I am a avid cross dresser, who enjoys playing the role of a uninhibited female sex slut, who shares herself with women. This game allows my ex (Amanda), to keep most of her marriage vows intact, while allowing her to e... Read full Story
shemale lover 2012-03-23 3,351 anal cum oral Sex Toys
100%
First Time Out
I'm so excited and want to relate this 100% true story quickly while it's still fresh. Please forgive any typos. [My background: Age 48. Closet dressing in earnest for 15 years. Began with slips stockings and nighties but have collected extensive full wardrobe and accessories over time. Boobs, wi... Read full Story
shemale lover 2012-10-23 3,593 sucking cum Sex Toys
100%
The New Nii
The bedroom door opened and the two lovers walked down the hall into the living room side by side. Deena was wearing her nightshirt that she wore a lot, and Jeffery was nude, and he picked up his clothes that I had put on the chair and began to get dressed. “Jeffery is going to go and get dinner an... Read full Story
Setinkhan 2021-05-28 5,938 Crossdresser Fetish threesome Big Cock Shemale and Girl domination Interracial Sex Toys