Sort by
Relevancy

Free Stories

80%
Karen, My School Teacher Part 1
The Meet By FoxyHosed It all started when we got a new class teacher. Her name was Karen. She was a mature lady and had dark red hair to her shoulders. That first day she wore some short dark blue jeans and a brown blouse. My other classmates started whispering about her. “He-he! Have you seen t... Read full Story
FoxyHosed 2021-01-29 9,411 Crossdresser Fetish redhead pantyhose Mature pantyhose cd
100%
Karen, My School Teacher Part 2
Just Staying a bit By FoxyHosed “Don't mention it. Now let me start on the pasta with meatballs!” She stood up from her chair “And besides, it will be nice to have someone to eat with, for a change!” She went to the kitchen to start dinner. “Make yourself feel at home!” I watched some TV ... Read full Story
FoxyHosed 2021-02-01 11,649 Crossdresser Fetish pantyhose Mature pantyhose cd
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 4,794 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Olderman and mature crossdresser Part 1
It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a c... Read full Story
shemale lover 2012-05-26 4,770 gay male Mature cd
88%
A Fantasy in Pantyhose
I always go out to the same bar on thursdays. The women are hot and long legged and they always wear pantyhose. Like usual, I dress in jeans, collared shirt and a jacket, deck shoes or dress shoes. Underneath, pantyhose. Always sheer to waist, no underwear and always nude. My jeans are long enough t... Read full Story
jonezn4ph 2012-11-24 6,685 anal pantyhose crossdressing gay
100%
Bi Pantyhose Passion
I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dress... Read full Story
shemale lover 2012-06-04 4,543 first time Cumshot Masturbation Fetish Blowjob pantyhose
50%
Eromenon vs mature whore
An eromenon for a mature whore When I looked up to see whose mannequin hands was serving my, I was surprised to find a girly-boy: ‘Something else,’ (s)he smiled, dragging his/her long, colourless varnished fingers across the tablecloth. I couldn't hold myself: ‘You've got the most beautiful ... Read full Story
hippocampus_171 2024-11-09 682 anal Crossdresser Amateur Blowjob Sex Toys Mature small cock big ass sissy femboy Ass to Mouth cum in mouth teen (18+)
100%
Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
darrell 2022-01-03 5,537 Group Sex Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock gangbang domination Sex Toys Mature cum in mouth shemale + shemale
100%
The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
Gwapo67 2022-05-03 8,705 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
37%
First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
shemale lover 2013-07-17 6,516 first time Crossdresser Fetish Mature bisexual
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 5,277 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
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 5,961 Crossdresser Blowjob transgender mature crossdresser gloryholes
50%
A meeting in the dining room
I sat in a boring dining room and ate a mediocre lunch in an even more boring hotel. The only thing that brightened the boredom was when a woman, ripe as a noble wine, entered. The skirt that barely hid her shapely nylon legs was perhaps a bit short, but otherwise it was a lady standing in front of ... Read full Story
Dussinvara 2024-07-15 3,815 anal Crossdresser Guy Fucks Shemale pantyhose Mature
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 8,266 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
100%
Karen, My School Teacher Part 3
Regret... Hmm Maybe Not. By FoxyHosed My excuse for a cock got hard again. My horniness got the better off me. I went to lock the front door. I took my shoes, pants and sweater off. I stood in the hallway only in pantyhose and t-shirt. ‘Don't do this. Walk away from this now. But you go to boa... Read full Story
FoxyHosed 2021-02-05 9,162 Crossdresser Cumshot Fetish Blowjob pantyhose pantyhose anal crossdresser guy fucks crossdresser
100%
Karen, My School Teacher Part 5
The Bus Station By FoxyHosed I looked around, but no one was there. It was dark and pretty cold night outside. I felt the air blowing around and up my pantyhose encased legs and ass. Mmmm nice. I started walking to the bus stop a few blocks further down from the school. I felt very attractive g... Read full Story
FoxyHosed 2021-03-15 7,654 Crossdresser Cumshot Outdoor Masturbation Fetish Blowjob pantyhose legs pantyhose cd
100%
A Downtown Moment
I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the compa... Read full Story
shemale lover 2012-02-28 5,234 pantyhose mistress
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 8,502 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
75%
Becoming Carla's Girlfriend
Carla and I were watching Netflix at home just relaxing after a long day of work. I remember laying down next to her and looking at the pink toenail polish on her feet. I taunted her as said "I could do a much better job painting your toes than you could." Carla smirked and said, "It's much ha... Read full Story
lacemint 2023-08-19 7,413 Stockings Crossdresser Lingerie pantyhose fantasies crossdresser lingerie nylon stockings nylons crossdresser panties crossdresser
100%
Reaching Paradise on Game Night
Reaching Paradise on Game Night by Sabrina G. Langton * Author's note: Here is one of my most popular stories. I get so many messages and emails about it and it makes me thrilled. I am so glad it has taken on a life of it's own. 'A wife learns a little too much about her crossdressing hus... Read full Story
Brina Giselle 2024-08-08 3,209 anal Stockings Crossdresser Blowjob pantyhose transgender wife dress-up
100%
A Religious Experience
A Religious Experience by Sabrina G. Langton *Stories from the real world 2 This story is kinda autobiographical. I was twenty-two in 1987. You couldn't just order anything you wanted on the computer, with no social interaction, and get whatever you wanted. You had to go out in the real w... Read full Story
Brina Giselle 2023-09-13 5,506 Crossdresser pantyhose transgender bisexual footjob dress
50%
Fellatio in pantyhose fantasy fulfilled
As those of you who have read my stories know, I love pantyhose. I'm also quite heterosexual in that I'm extremely turned on by femininity; thus the pantyhose fetish. I have no desire to "be" a female as I love my big penis and I love the way it feels in pantyhose. I also love shooting spe... Read full Story
shemale lover 2012-01-23 5,124 shemales taboo Fetish
100%
A Crossdresser Gets Fitted
Not long ago I was out shopping and stopped at one of the clothing outlet stores that I frequent when looking for sexy clothes and shoes to wear when I go out clubbing or to wear in my adult videos. I was looking through the display rack of my favorite brand of pantyhose, trying to find the colors I... Read full Story
shemale lover 2012-02-25 5,402 Fetish threesome orgasm pantyhose crossdressing
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,748 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Hose and Heels in the Bedroom
Liza giggled as she sat back down on the sofa, a mischeivous smile on her face. "Whats so funny I asked?" wondering what had tickled her fancy. After all the only thing that had happened was that she'd just been to the toilet to relieve the pressure that the 3 or 4 glasses of wine tha... Read full Story
shemale lover 2012-05-15 4,439 anal sex Cumshot Fetish fingering pantyhose heels
50%
Tea-Girl's Repeat Performance
It was the last night before my girlfriend was due back from the Hen Night she was on, and I had already washed her clothes from my previous day's fun with the electricity meter reader, during which I made a mess of her satin thongs, pantyhose and white body-tight top. I wanted to relax, with a bott... Read full Story
shemale lover 2012-09-01 3,987 Cumshot Masturbation Blowjob fuck pantyhose
77%
Discovered
3:00pm... The workday was done. I'd been eagerly waiting for this time. On lunch I pulled our 'toy' chest (actually a footlocker) out of the closet for easy access that evening. Months before, I told my wife, Kaitlyn, that sometime she's going to come home and find Nicole bound to the bed just wa... Read full Story
shemale lover 2012-09-27 5,106 Fetish pantyhose crossdressing
50%
Taken and in Public Part 2
As I stood on the corner of the street I was woozy. The heat from the day and how I just got fucked in public was running thru my mind. I tried to walk home quickly; my ass was a bit sore but it was not hurting. I could feel something dripping down my leg. I told myself it was sweat but I knew i... Read full Story
shemale lover 2012-01-13 3,279 Fetish pantyhose crossdressing
80%
First time out Part 2
After having experienced being out in public dressed up for the first time it was obvious I would want more of it. After leaving the adult theater I decided to take it to the next level. I Stopped off at a local all night store and went in to make a purchase. I picked up the things that I needed and... Read full Story
shemale lover 2012-04-19 3,221 Creampie oral sex pantyhose crossdressing
100%
Adventures In Hose
I gently rolled the pantyhose on my legs, marveling at the exhilarating feeling that they gave me. My imagination soared as I contemplated the humiliation of being caught wearing them in public and I felt my cock begin to stir in its nylon prison. My face slowly flushing in absolute pleasure, nothin... Read full Story
shemale lover 2012-08-16 4,260 ass Cumshot pantyhose
100%
Michael's Prom Night
Kelly and I are home for a few days and were staying at Kellys' mom’s house as usual. All week long all her brother Michael can ramble on and on about is the senior prom coming up this Friday night. He and Two of his buddies decided to pool their money and talked Kelly into renting them a Ca... Read full Story
shemale lover 2012-08-24 5,163 oral sex pantyhose cum swallowing
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 8,359 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
shemale lover 2011-09-13 5,673 Cumshot jerking off pantyhose
87%
Surprise Ending
I am 38 years old, married (for 13 years), and my job in sales takes me on a monthly business trip to various cities in the eastern US. I can’t say I have never been tempted on these trips away, but until last month just some friendly flirting at a bar was probably my biggest offense. That ch... Read full Story
shemale lover 2012-03-26 3,564 sucking pantyhose
60%
Nylon and lace
Well, I know it will be difficult to take this story seriously or as true happenings, it will seem far fetched and made up. I know, I know. It is however the story of my sexual awakening. The story of how I grew up to be what I am. I do not pretend to find psychological explanations or even less bio... Read full Story
shemale lover 2012-05-12 3,243 Fetish pantyhose crossdressing
100%
Sally's First
My heart was racing a mile a minute as my hand reached for the door knob to open a whole new world to me. Although I had been dressing for about 15 years, at 23 I still hadn't been outside or let anyone in on my secret. The last 3 years had been hell for me as I had started to play with dildo's a... Read full Story
shemale lover 2012-08-29 5,041 big dick Cumshot pantyhose cock sucking