Sort by
Relevancy

Free Stories

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 4,446 cum oral facial deep throat fucking
100%
Jobe, Cross Dresser Extraordinaire
I used to be pretty bored. Not last week, or a mouth ago, but the last twenty five years. Life has just always seemed to be… dull. But lately, things have been looking up. I grew my hair out recently, I've got black hair, I'm tall and skinny, perfect body to pretend you're a girl in. I'm t... Read full Story
shemale lover 2011-11-16 2,854 sucking cum jerking off cross dressing
50%
Eden
"Hey Frank, where ya been? I need ta ask ya somethin' man." "I'm on vacation. Talk to Abbey. She's the boss until I get back. Ya better get used to it, because when I retire in a few months, she'll be taking over on a more permanent basis." "Retirement? You're only 29 years ... Read full Story
shemale lover 2011-11-25 3,631 cum oral cum swallowing
85%
Came to play
I spent my childhood at my grandmas house while I was growing up, there was several kids in the neighborhood... I basically grew up in the ghetto side of town. I knew more black people than white. I went to a school where there was always atleast a fight a day, so I kept to myself for the most part.... Read full Story
shemale lover 2011-11-29 3,177 first time shemales interracial sex
50%
My Fantasy with a CD
I'm lying on a king sized bed, only wearing jeans, I'm relaxing and then a sexy CD/Transexual/Shemale stands in the doorway, I look up noticing a sexy, CD who had a hourglass body, with nice big curvy legs and gorgeous ass! I noticed shes about 5ft 11, with long curly brunette hair..... sea blue ... Read full Story
shemale lover 2011-12-21 3,432 shemales Masturbation Fetish
90%
The Conference
It had been a long day at the conference. During my evening meal in the hotel restaurant with some colleagues I noticed a stunning looking woman across the room. We met eyes on several occasions and acknowledged each other with a warm smile. She stood up to leave the restaurant and I was able ... Read full Story
shemale lover 2011-12-24 5,584 Fetish crossdressing erotic encounters
87%
Beaches
A couple of things you should know about me: I'm not gay; I've always had this thing for dark-skinned women. I graduated from the army at age 21 and headed home to the Bronx. Me and a buddy of mine started up a livery car service. We started with four cars. 15 years later, we had 100 cars and alm... Read full Story
shemale lover 2012-01-03 4,972 Fetish shemale Ebony
100%
A New Me...
Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn't all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending. My sister and... Read full Story
shemale lover 2012-04-14 5,266 Masturbation Fetish crossdressing
100%
Humiliation
My ex-wife and I still get along okay for the most part. She was enthusiastic about feminizing me. Occasionally she would get enough of it and then just go overboard to shut me up for a while. One such incident stands out. After a particularly nasty week at work, I came home Friday evening lookin... Read full Story
shemale lover 2012-05-21 4,451 anal sex Cumshot Fetish domination oral sex feminization
100%
Caught by Dave!
Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed. No one I know even suspects that I'm a slut at heart or that I am the least bit bi. But more and more I keep fantasizing about one of my male friends. He's very good looking and keeps... Read full Story
shemale lover 2012-06-15 3,503 Crossdresser Cumshot Fetish Blowjob cum swallowing
100%
Bobbi from Tennessee
Six months ago ... "I'm leaving now, Bob," Sue called out as she left. "I'll be back in a couple hours." Bob waited until he heard the garage door close before going to their bedroom. He looked through Sue's underwear drawer before deciding on a sexy pair from Victoria Secr... Read full Story
shemale lover 2012-07-22 3,811 Cumshot Fetish oral sex
100%
Fender Bender Chapter 4
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. It was Tuesday evening and I had stayed home alone all day. I had a lot to think about. I was relaxing and listening to some music on the stereo. Mom had just ... Read full Story
shemale lover 2012-07-26 3,161 anal Creampie oral sissy
66%
Your Waitresses
You begin your evening by taking a long luxurious bubble bath followed by taking the time to apply your makeup at a beautiful white makeup table and mirror from the 1920's. You then slide a sheer pair of black stockings up each leg and attach them to your black and red lace garter belt. You then run... Read full Story
shemale lover 2012-08-10 3,717 Fetish cum crossdressing
100%
Caught Exploring
I open the hotel room door and look around the room. The front room has a couch and table and the back room has two beds. A window in the front room looks out on the walkway and then past to the open atrium. I close the door and walk to the bedroom with my bag. I think again about the chat from l... Read full Story
shemale lover 2012-10-11 3,706 Cumshot oral sex deepthroating cum swallowing crossdressing
100%
Flowers in the Heart Part 2
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 6,258 sucking oral sex facefucking
100%
Francis Meets a Black Stud Part 3
As I washed myself in the women's bathhouse, I began to regret everything I had done. I had already cum and the sexual intoxication seemed to be gone. I could not believe that I had willingly submitted to what I had allowed that black man had done to me. I began to be very disgusted with myself. Fur... Read full Story
shemale lover 2012-11-20 3,683 sucking handjob black cock
100%
Dressed for Sex
"Thanks Dana, I'm glad you could get here on such short notice." "No problem Angie, I'm glad I could help you out." "I'd have waited until Nick got home from his trip, but I really needed to get the laundry started and I haven't had water all weekend." "Wh... Read full Story
shemale lover 2012-11-22 3,693 Fetish oral sex feminization
100%
Fun Times at Halloween
It was almost Halloween and I was stumped for a costume. I was excited, tonight was the annual Delta Kappa Halloween Bash, the biggest fraternity party of the year. All the Greeks got dressed up for this party, even those not in DK. I headed down to my friend Kathy's room to see if she could help... Read full Story
shemale lover 2012-12-08 5,207 Fetish oral crossdressing
100%
Fun With Friends Chapter 2
After Becca said that, my eyes moved across to Greg's face, unsure of what to expect. I didn't know if he was going to be angry that his girlfriend had tricked him into thinking that it was her stripper friend Davina that had been giving him a lap dance and a blowjob before revealing at the last... Read full Story
shemale lover 2012-12-11 2,686 Fetish cum oral
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 14,053 hardcore sucking ass fucking Guy Fucks Shemale
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 12,236 first time oral sex nipples crossdressing cd sissy
90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 12,435 first time cumming crossdressing cd sissy cumshot in mouth
87%
My First Crossdresser
Only a few years back in my young 20's i discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls pictu... Read full Story
IrishJames 2016-09-09 10,776 first time ass Crossdresser cd sissy deepthroat
100%
Castro - shemale goddes
Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effec... Read full Story
Law12 2018-03-04 5,047 Masturbation Bareback Creampie Ass to Mouth cum in mouth Supernatural
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,343 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
Hooked On Shemale Cock
Nitromethane Well, that did it, I finally swallowed my first load of shemale cum, and I haven't been able to get it out of my mind since. It was three years or so that I'd been wanting to have a shemale cum in my mouth, and it was everything I'd dreamed and more, but now what? I'm at work think... Read full Story
Gwapo67 2022-02-01 3,247 cum in mouth
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,714 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
95%
My TS Journey
I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my a... Read full Story
iconicirish 2022-10-26 8,208 Amateur Shemale Fucks Guy Big Cock domination cum in mouth escort ts
100%
Shopping plus extras!!!
Hi, so as you can probably imagine I buy a lot of underwear and have a few favourite places to shop. My favourite by far is Ann Summers. The range is great and the staff are so helpful . Anyway back to the story. So I decided to go get some new underwear to see in the new year, I got myself up and d... Read full Story
Samantha Jewels 2023-01-06 4,322 Crossdresser Amateur Cumshot Fetish threesome Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Why I’m a Cock Whore!
Hello Love, The summer before my freshman year in high school. I found a VHS porno video right next to a dumpster behind our local video store. Brought it home. Couldn’t watch it until my family left to use the VHS player. It turned out to be a she male porno at first I felt weird but after watch... Read full Story
Samantha Cummins 2023-04-18 6,135 anal Stockings Cumshot Creampie Lingerie femboy Ass to Mouth cum in mouth
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 4,606 Stockings Big Tits Shemale Fucks Guy Fetish Blowjob blonde domination Guy Fucks Shemale blonde shemale PDA Public Displays of Affection
100%
The Three of Us
Imagine you are a lonely person on the inside, and just wanting all your life to be loved for who you are. Holli Artigas, was just that person. Wondering whether her obsession with Jon Silva, a football star, was from a casual encounter, or was she truly fond of him? Growing up in the Sao Paulo, ... Read full Story
Jon Paul 2024-04-28 3,147 anal Creampie Shemale Fucks Guy threesome Shemale and Girl cum in mouth double anal shemale fucks female
57%
Ambers torment
It seem to be the typical day for Amber as she entered the home of Master. The usual early wake up and long drive down to his house seemed nearly routine though, the last visit was a few months past and the girl was anxious for what was to come. Although, her expectations were not different from any... Read full Story
shemale lover 2014-04-19 7,259 shemales Fetish bdsm
84%
The Making of Erica - Sperm Loving Crossdresser
Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... Read full Story
shemale lover 2015-09-03 16,589 shemales Masturbation Fetish
75%
Bambii's New World
My mind was racing the whole time. I couldn't believe where I ended up. But the sensations were running through my body. A 9-inch cock was ramming my boy pussy as hard as it could. Another cock, at least 10 inches, was being forced down my throat as his hands wrapped around my head, forcing me to... Read full Story
shemale lover 2011-10-05 5,149 shemales Blowjob cum
100%
The House of Lesslie Part 2
I. I woke up. Even after having taken over the House of Lesslie weeks ago, each morning was still the same, and came with the same feeling of disorientation, in need of a few moments to adjust to the realities around me, as new as they were. The bedroom around me was still darkened by heavy... Read full Story
shemale lover 2011-10-14 4,638 Fetish domination nipples
84%
Page Sixty-Nine
When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make... Read full Story
shemale lover 2011-10-20 6,011 cum oral deep throat fucking
50%
Caught cross dressed Part 3
The next few days felt like a lifetime for me. I couldn't sleep at night - every time I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked me from both sides. Everything I ate and drank had a horrid aftertaste of that bas... Read full Story
shemale lover 2011-11-21 2,890 shemales Fetish bdsm
100%
Jamie is taken Part 1
Jamie loved his job. Not only did he enjoy the job itself, but it also provided him with outstanding opportunities when it came to getting laid. Jamie was 21 years old and had moved to the city eighteen months before. Not long after he had gotten the job, working as a sales clerk and tai... Read full Story
shemale lover 2011-11-30 5,126 Fetish bondage extreme exhibition
97%
Stepdaughter's Transexual Surprise
I've been through two marriages in the past. My first wife died at an early age of 29 from a massive heart attack and my second marriage was a nightmare from hell, that I'm now free of. When I met Jeanie, I knew I had to take it slow and easy. Jeanie was a very nice lady in her early 40's. I myse... Read full Story
shemale lover 2011-12-04 13,556 anal Fetish transexual
100%
And Life Goes On
I am sitting in the living room waiting for my date to show up. A date arranged by my wife Gwen. I am dressed in a slinky red dress, underneath my torso is encased in a white corset which reduces my waist to a mere 25 inches. On my legs are a pair of black nylons attached to the straps hanging down ... Read full Story
shemale lover 2012-01-10 5,664 sucking Fetish crossdressing
100%
1st Transsexual Affair
Paul's cock was hard as a rock and with a penchant for sleeping in the nude, its fat length pressed against luxurious satin sheets. The dream of searching for a urinal or bathroom now became reality. He stretched, groaned and yawned his way off the comfortable bed and padded across the room. The mar... Read full Story
shemale lover 2012-02-04 4,223 cum fuck oral
100%
Force Feminized up Asshole
"Yea I thought the singing was OK but I don't really go for that style too much" "And the girls?" Brian prompted me. "Oh come on Brian leave him alone we all know he's not really interested in girls." "Give him a chance, people can change! Perhaps Carl's d... Read full Story
shemale lover 2012-02-13 6,623 anal Group Sex Fetish cum feminisation
100%
Barbie Jo Adventures Part 1
Halloween night It was agreed by all three of us that we would dress up as women and Wanda as a guy. So when I arrived by taxi and went into the house I was wild that I was the only one dressed up. I stood there, my face as bright red as the lipstick I had on while Peter, John and Wanda whistled ... Read full Story
shemale lover 2012-02-17 4,477 Fetish cum swallowing stroking crossdressing
100%
Barbie Jo Adventures Part 5
Friday Night I've gone all week as Joe; no one at work has said anything to me about Monday morning. So I assume I got away without being exposed as a cross dresser. I was working late all week and finally Friday is here. I am so horny and anxious to become Barbie Jo. Hopefully someone will call,... Read full Story
shemale lover 2012-02-18 4,306 sucking Fetish cum swallowing
100%
A Cross Dressing Suck Off Fantasy...
Yes, this is a true story that really happened to me a while back. I went out of town a few weeks ago on business, and at the same time, I was hoping to hook up for some hot man sex. I went to the Male Hookup Forum page for the city I would be visiting and posted a message. The message read " W... Read full Story
shemale lover 2012-02-25 3,745 Fetish oral sex cross dressing
100%
Cab Driver
I already have a raging hard on, and it is only 9pm. I have my clothes for the evening laid out on the bed before me, and my cock, balls and ass are newly shaved. I have decided to wear all black tonight: black lacy panties, bra and suspender belt, sheer black stockings, and a tight black dress that... Read full Story
shemale lover 2012-03-01 4,712 Stockings Creampie Fetish oral sex heels
95%
A Helping Hand
It was late on a Friday night when I heard my parents arguing. It always happened whenever they were getting ready to throw a big party. My mother played the role of party planner and handled all of the details, but between caterers, musicians, and the other help something always went haywire. My fa... Read full Story
shemale lover 2012-03-09 14,870 Fetish bdsm transformation
100%
Been Caught Cheating Chapter 3
I awoke in pain. I had slept bound all night. And it also seemed that I had been hit with something to wake me up. Angela was standing over me with one hand on her hip and the other holding my bounds that I slept in. She was already dressed and ready to go. I looked around to make sure we were alone... Read full Story
shemale lover 2012-04-23 4,102 Fetish domination crossdressing
100%
Crossdressed and 2 salesmen come by
Imagine your expecting a salesman to drop by at noon to show you some samples of wallpaper-You start your shower at 8 AM-you finsh up by shaving your legs real smooth-you go and put on a pair of full cut thin strechy full cut skimp skamp white panties-next you pick out a lovely open girdle and pull ... Read full Story
shemale lover 2012-05-16 2,618 Fetish voyeur oral sex crossdressing
100%
A Reluctant Gang Bang
Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... Read full Story
shemale lover 2012-05-28 8,527 anal sex Creampie Fetish gangbang crossdressing
85%
Caught by Neighbour
- 1 - It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not... Read full Story
shemale lover 2012-06-20 4,688 Cumshot Fetish oral sex crossdressing
100%
A Slut is Born
There I was, one week before the end of high school. Going to college in the fall. Nice car, good family, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in m... Read full Story
shemale lover 2012-06-26 6,356 anal sex Fetish oral facial feminization
50%
A Trilogy of Trannie Tales
Terri and I had been having phone sex with each other on a telephone chat system for several days. We agreed to meet and go to my favorite park one day at around sundown, when most others would be leaving the park. Our intent was to flirt with and fondle each other around the other people, and then ... Read full Story
shemale lover 2012-07-11 3,537 Cumshot Fetish shemale oral sex
100%
Fender Bender
It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... Read full Story
shemale lover 2012-07-26 8,363 Teen (18+) Fetish crossdressing
100%
Fender Bender Chapter 2
The bright sun shining through the window woke me up, for a moment I was confused and disoriented. Then it all came back to me. I had sex with Mark and Susan James last night and I was still wearing a pink baby doll nighty and matching panties she had given me to put on before we went to bed. I w... Read full Story
shemale lover 2012-07-26 4,340 Teen (18+) Fetish crossdressing