Sort by
Relevancy

Free Stories

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 7,732 shemales Fetish bdsm
100%
Mommy Writes for Mandy
We work in a big corporate office. I am the owner of the advertisement company and you are my secretary. You are fully Mandy. You started taking hormones years ago to fully become a girl. Your hair is grown long and you have little a cup breasts and chose to always wear dresses, skirts, frilly blous... Read full Story
shemale lover 2013-03-12 4,925 Teen (18+) Crossdresser Cumshot Lingerie ass fingering
87%
smoking
Greg decided to go straight. I had to find a new place to live. A nice man, Pete, who I knew from the YMCA, offered me a place in his basement. He was going to rent it out. It was nice, full kitchen, bedroom, laundry room, living room and another space for anything I would need. His rent was che... Read full Story
cd4fun715 2019-01-08 3,180 Amateur
100%
Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
Gwapo67 2022-07-22 6,359 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
Mistress Faye and sissy selena
Mistress Faye, a towering figure in shimmering black PVC, her curves as sharp as the stiletto heels that clicked against the cold, hard floor, surveyed the room with a predatory gaze. Her submissive for the evening, who had lent off the stunning Mistress Debs, Selena, kneeled before her in a matchin... Read full Story
MasterofSissies1 2024-11-16 878 bdsm Shemale and Girl Latex bondage femdom sissy anal fucking chastity domme
85%
How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
shemale lover 2011-09-06 21,456 asshole Masturbation cum
80%
Adult Porn Shops
Around my senior year in high school I became more enamored with sex as all teenagers do. I loved lesbian sex and was addicted to shemale's as well. Nothing turned me on about gay sex. I was only curious about being with a shemale. So being underage the only porn you can get is via internet or throu... Read full Story
shemale lover 2011-10-09 5,371 domination gay porn booth
100%
How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
shemale lover 2012-04-15 3,622 anal transformation oral glory hole
85%
Alternative Plans
Another Goth Trans Girl Confession I really enjoyed my first sexual experience. I had gone to the local adult entrainment store and purchased some toys; a butt plug, a 10inch purple dildo, some lube and condoms. I would occasionally play with my toys while watching some internet porn. I loved ro... Read full Story
Gothtransgirl41 2017-11-10 11,658 domination cum in mouth quickie
100%
How it began (1/x)
About two years ago I was in a relationship with a woman that I'd always considered to be out of my league. She was a tall, tattooed lady with black hair, who used to wear incredibly saucy dresses, knee-length boots and flamboyant make-up. Me, on the other hand, I have always been a quite unrema... Read full Story
sissylennie 2022-09-07 4,548 Crossdresser threesome domination mistress Cuckolding Cuckold Sissy
100%
First Time with a Male Part 2
After her hair was rinsed, Travis squeezed the water from her hair. Then he wrapped a towel around her head and sat her back up. Before Travis unwrapped the towel from around her head, Mavis reached over and began to massage his crotch. "We have company, darling," Travis said, as Mavis ... Read full Story
shemale lover 2011-12-01 3,138 facial deepthroating cum swallowing
66%
She Called My Bluff!
Hi my name is Michael, this begins a story about a moment of weakness where I severely underestimated my wife's determination and resolve to hold me to a promise. My wife Carol and I had been married for about five years, she was a bit older than me in her mid thirties. With a bit of age she h... Read full Story
shemale lover 2011-11-16 6,491 suck shemale orgasm
100%
The Greatest Lie Part 4
Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... Read full Story
shemale lover 2012-01-19 5,056 taboo femdom crossdressing
60%
Quick Fix
My anticipation couldn't be expressed in words. It had been a while since I'd had a visitor to my apartment. The last experience had ended quite well, with the bed sheets being more than a little tussled up. I was preparing myself with an erotic movie. The sex scenes always turned me on, my fu... Read full Story
shemale lover 2011-08-31 2,698 asshole cum oral
100%
Connie at an Adult Bookstore Part 2
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * In the previous c... Read full Story
shemale lover 2011-09-30 8,922 Big Tits Blowjob deepthroating
100%
Toying fun
Wow, Its been almost a year since I last visited this site. Since then I have some stories to tell you all. About 7 months ago, I met a guy for some toy exchange sex. He wanted to try out a bunch of toys on me, the biggest he had was a BAM dildo, what a monster, it took ALOT of lube & patien... Read full Story
shemale lover 2011-10-11 2,689 anal asshole dildo fisting
50%
Healthy Behavior
"Uhh…is Mr. Stanford around?" "One moment dear…ooh, damn heels. Makes it impossible to walk through doorways. Here I am ma'am. So, did the maid get you here alright? Hello? Earth to…" "I can't believe this…" "Oh, the heels? Yeah... Read full Story
shemale lover 2011-10-19 4,297 Big Tits transsexual oral
100%
Trying It On For Size Part 2
I looked up and saw the low slung scrotum swaying above my eyes, the long, thick, curved shaft pointing upward just in front of it. I heard a quiet tearing sound,"schshhhtt," looked further up and saw Tanya opening another one of her black foil Magnum condom wrappers. She placed the large,... Read full Story
shemale lover 2011-10-26 6,123 domination bondage anus
100%
How I Became a Tranny Whore
When I was 30 with children at home I would get dressed in the bedroom. When it was time to leave the wife would take the children off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the children would be a sleep. The plan worked fo... Read full Story
shemale lover 2011-11-07 4,954 anal Cumshot cum swallowing
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 3,977 cum oral cum swallowing
100%
Rachel and Chris - followup for Crissy
“Crissy!” I shouted at you as you peered out of the closet door. “What in the hell are you doing spying on Rachel and me?” I asked. Before you could answer, you saw my hard cock pull out of your sister’s pussy, covered in shiny sweet juice. You knew you wanted it ... Read full Story
shemale lover 2012-04-10 2,814 Creampie cum swallowing crossdressing
80%
Hermaphrodite Blackmail
I remember it as though it were yesterday. 19 years old, jut dropped out of college over a sex scandal with my History professor. I managed to find a good job in a high end boutique because I was beautiful, sexy and could pass myself off as classy, even though I was a cheap whore. My boss was ... Read full Story
shemale lover 2012-06-02 4,471 cum fingering domination cum swallowing doggy position
100%
Damsel In Distress
1. The Request Duncan was fond of his older sister, Helen, but she pushed the boundaries of brotherly love to its limit when she asked him an unusual favour. 'Let me get this straight.' Duncan said, lounging on his bed whilst listening to the radio. 'You want me to escort you on a date with some ... Read full Story
shemale lover 2012-06-06 3,425 Fetish crossdressing high heels
86%
BoyTrainers, Inc.
Peter was taking a long time in the shower again that morning. His mother pressed her ear to the door, and detected soft moaning. Inside the shower, Peter stood, pumping his penis with his hand, eyes squeezed shut. He was a little underdeveloped for 18 – short for his age, and didn't seem t... Read full Story
shemale lover 2012-08-19 6,818 jerking sissy
100%
Dimensional Portals Suck Ass
Marley was dead: to begin with. Hold it… no, no that’s not right. My mind is wandering. What was I gonna write about? MATT! Yeah, Matt was a bastard. And I mean it in the sense that he sucked monkey balls. That’s an expression I like, sucked monkey balls. Anybody ever played blows... Read full Story
shemale lover 2012-09-21 3,402 Creampie oral facial huge tits
100%
With an 'E'
This story could come under a range of headings, Mature, Couplings, or Transgender. But, I guess, Transgender is best, as I have enjoyed the luxury of satin against my body for some time now. Having Lived alone for the last few years, soft, swirly clothing and satin panties keep me constantly ... Read full Story
shemale lover 2012-10-10 3,079 anal cum oral
100%
First Time Drag Chapter 2
We'd been together for almost one full year, maybe the happiest year of my life. Michael had expanded his feminine side, dressing up and wearing makeup more often than not. His hair had grown too, now almost at shoulder-length. Though twenty-one, he was still really just a boy, or maybe just a girl.... Read full Story
shemale lover 2012-10-12 2,321 Cumshot sucking stroking
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 17,100 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
87%
Story of Heather Chapter 1
So I have been struggling with who I am ever since I could remember. I guess the main point I'm trying to make is I was born a boy, but have always had the urge to be a girl. For years I have battled this and the growing hunger of letting this inner woman come out. As I have progressed through the y... Read full Story
shemale lover 2013-01-17 3,880 Teen (18+) Crossdresser Cumshot sucking Interracial
80%
Trained and Tailed
It started like any normal relationship. I had dated my owner for several weeks now. He was not my owner yet, at the time he was just my boy friend. He was older than me, I was only twenty four and he was in his forties. A bit older than I had ever dated before, but he seemed nice and I didn't have ... Read full Story
shemale lover 2013-02-12 5,838 Big Cock ass fucking domination cd humilation
85%
True story, TS 3-way
This is a true story. It was a typical night in Pattaya Thailand and I'm still recovering from the 25 hour flight from Tennessee to Bangkok that I flew just days before. After a few days in BKK, I arrange for a hotel car to me to Pattaya, a seedy explosion of lights, blaring music and drunken ... Read full Story
Thailover 2014-03-11 10,154 Cumshot threesome jerking ass fucking facial stroking
100%
My Life as a Shemale Part8
It was on my way home when I decided not to tell Tim about Sin. This was very private and it was already bad enough that I knew, also, I had no idea what Tim might say or do. I did want to stay friends with her, now more than ever. It was friday morning, the day after Sin was ****d and I was eager ... Read full Story
shemale lover 2015-02-27 4,197 tranny licking Big Cock Lingerie stroking
85%
Journeys of a girl finding herself... A wonderful date with my D
I nearly lost my virginity as a woman last night... I have been seeing a very sweet and sexy Domme for about a month now and she has been pushing me and making me see myself in new ways. I have talked about how when she started to introduce forced feminization upon me, she could tell it was not forc... Read full Story
Faye_Valentine 2016-01-18 3,664 suck Lingerie ass fucking dick strapon transgender
100%
Online Mistress Chapter 1
My name is Kayla Andrews, I’m a closet sissy gurl who loves the color pink and everything femme! Nobody knows about my little secret except for my private online world. Recently I put out a craigslist ad for an online mistress and I got a response from a beautiful blonde woman who was looking for a... Read full Story
CandyShopKayla 2016-02-16 5,824 bdsm cum trans sissy crosdressing
93%
My wonderful life with Pat
Hello, I am or better to say I was a straight guy before my life with Pat, let me tell my story with her. This new life started when I was 35, VP in an IT company and living in the south of France, close to Bordeaux. After my divorce, i used to go some bar after the business day. I felt alon... Read full Story
jperrot 2020-07-17 4,630 Amateur Big Cock cum domination slave Ass to Mouth france
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 8,053 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
100%
First intercourse with a man
If you read my previous story, “First time with a man”, I gave my first blowjob. What I didn’t mention at the time, was that I was on my way to work about 2pm in the afternoon, (I worked the swing shift). That afternoon meet up was just to see each other, talk and maybe meet again later. But my e... Read full Story
Mistysis 2020-10-23 7,564 Crossdresser Amateur Bareback
100%
My first gay experience
Unlike most stories mine is from experience. There is no subtlety or seduction just an account of my first time. I had weekend fishing trips with a mate called Simon, we jointly owned a caravan which we used as out base. We were both in our forties. We are both married and our wives know each other... Read full Story
lkusex 2021-05-27 3,495 Amateur Blowjob Big Cock
80%
Physical exam that embarrassed the fuck out of me.
Hello and welcome. My names safebet1980 aka Dug if you want a easter name to remember lol.. Right about now some of you are saying to your selfs that name sounds familiar and it might. If your looking at porn I'm on a lot of sites both as a user and a uploader of Amateur videos I both shot and sta... Read full Story
safebet1980 2022-10-11 5,028 Amateur Homemade
100%
Something new
So I’ve been dressing up for a long time, and I’ve been doing videos for a long time and absolutely love it (hope you do to). Well I needed something different to do so I decided to take up an invitation to join a group of gurls on a weekend in Amsterdam!! I have been to Amsterdam about 10 times ... Read full Story
Samantha Jewels 2022-12-14 4,117 Crossdresser Cumshot cum in mouth
80%
Chastity and its effects
I actually thought of writing this for some time now, this quasi-scientific testimonial and reflection about chastity. Now, I finally had some time to reflect, gather and compare info and experimentation from personal experience about the topic. More specifically, the effects it has on the mind and ... Read full Story
DoraTV 2023-02-09 6,781 Crossdresser anal play chastity sissygasm Sissyfication story chastity orgasm
100%
I Fooled Everyone But the Black Pimp Part 4
Fuck. I said I wasn’t going to do any drugs and I’m drinking this Gatorade that I know has something in it. Trish said it would help my nerves, and it has, I feel loose…and very horny. When I’m usually horny my cock is hard but right now, I’m putting lotion on my body and I’m going really slow over ... Read full Story
cdtampa4u 2023-05-17 5,410 Crossdresser Blowjob Interracial sissy bbc
100%
Ladies who Lunch - At the Gloryhole
Ladies who Lunch - At the Gloryhole By Sabrina G. Langton *** Author's Note: Hi, just a quick little story to make us all wet and squishy. Three mature crosssdressers have a little more excitement than they are used to after lunch. I hope YOU like it... *** The Boynton Tavern So w... Read full Story
Brina Giselle 2024-01-06 5,975 Crossdresser Blowjob transgender mature crossdresser gloryholes
100%
Alone at home
Living with my religious parents didn't provide many opportunities to spend time alone to enjoy myself. Only openings I found where, when showering, and occasionally when my parents travel, though that was not very often. I shared my room with my lil siblings, and since they were young and curious, ... Read full Story
Sara M. 2024-01-16 6,987 solo Lingerie small cock Homemade sissy femboy
100%
My first made me a femboy (3/3)
I could tell he was turned on and after turning my attention back to myself I knew I liked how I felt too. I adjusted the panties around my hips and ass until they laid flat and smooth against my body, they fit me perfectly. I asked him if liked they way the looked, but I knew without him saying ... Read full Story
boytoypdx16 2024-07-08 3,206 femboy teen (18+)
100%
The Story of Stephanie (Chapter 5)
After that trip to Kinky's Closet, things quietened down a bit for me. I wasn't really dressing as much and wasn't online as often. Then my life changed. I started a new relationship with a woman. Slowly but surely I felt myself falling for her. But she was very different from girls I'd been with pr... Read full Story
Stephanie Wild 2024-07-11 3,323 Crossdresser Amateur
100%
My first pre-op story
I started becoming interested in transsexuals a couple years ago, when I ran across some websites where I found some crossdressers attractive. I was 19 at the time. This led me to picking up Transformation magazine, a magazine more for the TG community, but they featured some really got centerfolds ... Read full Story
shemale lover 2015-06-03 11,187 anal Asian domination
85%
Jenna & Stephen Part 1
Jenna and I have been friends for nearly 15 years. We dated ever so briefly about 12 years ago, but nothing more than kissing and heavy petting occurred before she decided it wasn't going to work out. At the time I was heart-broken, but looking back now, I realize she was correct that we weren't rig... Read full Story
shemale lover 2011-09-01 4,480 dildo orgasm
50%
Puzzle
Women. There's no figuring them. They're a puzzle, one of life's mysteries, and that's a fact. Who knows what goes on in their brains, or whether they even have brains? I mean, what rational creature would get excited over Valentine's Day? Could any holiday be more obtuse? Like your bitch, mine's... Read full Story
shemale lover 2011-09-05 3,382 Big Tits asshole scrotum
0%
The Surprise Call
"Thanks for the wonder full time we had together last night Army Bear, it was awesome! I hope, we keep in touch as we both agreed," I sent my toy boy an email the day after our Valentines date. I was still thinking about of our hot night/morning together, I couldn't keep him out of my mind... Read full Story
HotVersatileTs 2011-10-04 4,539 sucking domination ts foreplay
100%
Becoming Amy
I had been dressing up in women’s clothes since I was a kid. Started with my sister’s clothes, I loved her school uniform. I used to prance around in it when I was lucky enough to have the house to myself, which wasn’t often. I loved pretending I was a school girl, and a rather nau... Read full Story
shemale lover 2011-12-06 7,338 anal shemales bdsm
100%
Tony to Tanya
My name is Tony and I'm an average 19 year old boy. I'm 5 foot 7 inches tall, have shoulder-length brown hair and blue eyes. I often get mistaken as a girl from behind because of the length of my hair and because I look after it really well. I've been told I'm as good-looking as most girls my age. M... Read full Story
shemale lover 2011-12-19 4,638 cum dildo ass fucking
100%
Tony to Tanya Part 3
Sarah finished applying make-up to Tony's face. It was mostly subtle, just enough to highlight his eyes and cheeks. The only part that wasn't so subtle was the lipstick; bright red. He was already dressed up in a beautiful black dress that left his back and shoulders exposed and only went down to... Read full Story
shemale lover 2011-12-19 4,915 anal cum oral
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 14,600 anal Blowjob black fiction
100%
A Single Night
"You know your a slut," she said, as she turned around walking away from me and began sashaying around the corner. She came back a few minutes later with her hair teased up and wearing a slinky, silky baby-doll. My eyes stayed locked on her as she approached me as a silken seductress. I... Read full Story
shemale lover 2012-06-14 2,850 Fetish climax sissy
25%
A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
shemale lover 2012-07-05 7,282 Creampie Fetish crossdressing virginity