Sort by
Relevancy

Free Stories

0%
Crossdreaming Thoughts
Last week I crossdressed for a while. Wore tight dark green jeggings, and two different shirts. I was barely able to squeeze these huge fucking J cup tits into a basically skin tight size XS stretchy nylon beige tshirt, and the other was an olive green turtleneck of the same tight fit. Wore both ins... Read full Story
Maika Arreola 2018-03-02 4,404 Crossdresser Amateur Big Tits Big Cock Mature Homemade
83%
Wife Left Me so I Could be a Girl
I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with... Read full Story
ASSEaster5678 2018-07-09 10,501 Shemale Fucks Guy Ladyboy Mature
88%
Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
ASSEaster5678 2018-07-10 10,812 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
100%
Porn Cinemas and GinaG
I really like porn cinemas, there is a certain seediness and sleaziness about them that makes them alluring to me. My problem is that living as I do in the south of the UK, there are no porn cinemas anywhere near me. Fortunately, I travel in my job quite a bit and so can get to cinemas in Birmingham... Read full Story
GinaG 2019-01-08 3,448 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
100%
Lady In The House Ch. 06
A story by MicheleNylons (Michele continues to be used by prison inmates.) From Part V Harry leant over me and kissed me full on the lips. "That was worth every penny; you are one hot nurse," he laughed. Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silver... Read full Story
✘Transensual✘ 2019-02-25 3,788 Crossdresser domination prisoner prison sex Prison Bitch
100%
Ich und der Kommissar
Ich und der Kommissar, nach einer Vergewaltigung wollte ich mein Erlebnis einem Polizei Kommissar schildern. Wir saßen im Wohnzimmer auf meiner Couch, er sagte zu mir ich solle ihm meiner Erlebnis schildern, er merkte das ich etwas gehemmt und schüchtern war, er bot sich auch als Statist an, er sag... Read full Story
Jaque böses Mädchen 2020-08-13 2,702 Crossdresser Amateur Cumshot Bareback Creampie Fetish Blowjob Big Cock domination Guy Fucks Shemale Compilation Ass to Mouth cum in mouth
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,104 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
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 4,090 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
66%
My girlish desires
My girlish desires, I am happy to spend my weekend at home to live my life as a woman. I apply a depilatory cream to my body, which I leave to act for a few minutes before going in the shower. I take this opportunity to do an enema to avoid unpleasant surprises during my girl games. Then, using ... Read full Story
sandratvtg 2023-01-19 4,041 Stockings solo Cumshot Creampie Fetish Big Cock Lingerie Sex Toys
80%
What I like
I like cum from cocks, a copious creampie dripping from a pussy, or licked off a warm body. I'm an older guy but I'm still fit, active and horny all the time. I like to masturbate while looking at porn with a prostate stimulator up my ass, wearing nipple clamps and a cock ring after smoking some pot... Read full Story
SylvesterLeChat 2023-08-15 4,647 Masturbation Creampie Blowjob Big Cock Ladyboy Mature small cock sissy cum in mouth
81%
A fantasy of mine with a sexy cd or tranny
i wanna dress you up in a sexy blue fishnet shirt with a red lacy bra under, a short black miniskirt with a pair of red silk panties, some thigh highs and a pair of red high heels and take you out somewhere and fondle you a little here and there then go back to your place and take you to bedroom and... Read full Story
shemale lover 2014-02-21 3,369 anal shemales Fetish
100%
Barbara & Vikky Part 1
I'd known Barbara for some time now. She was a mutual friend of a friend, Trina, and we often bumped into each other in the street, or at the store. I liked her and appreciated her company and humour. She was 57, somewhat older than me, being in my mid-30's. We spent many evenings chatting and laugh... Read full Story
shemale lover 2011-10-22 4,165 anal shemales Mature
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 4,850 shemales taboo Fetish
100%
A Flash of Lace
The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... Read full Story
shemale lover 2012-03-03 6,191 Stockings Fetish dressing
100%
Best trip to the mountains
I was driving out to the hills for some solo camping. I was alone since all of my friends had quit on me at the last minute, but i figured i'd just enjoy nature while i had the chance. I was almost through with the four hour drive, and noticed fewer and fewer cars as i got closer to the site. Onc... Read full Story
shemale lover 2012-03-04 3,929 anal shemales Group Sex oral
83%
A Man's Place
I couldn’t believe my luck, a raise! Finally, after working three years in this stinking company as Marketing Manager, and I finally get a raise. Okay, granted, it took for the company to be bought out, have a number of people sacked, and to squirm like mad to do it, but I got there! 5000 quid... Read full Story
shemale lover 2012-03-18 3,425 Stockings Fetish cum oral feminization
33%
Freshy
It was to be my first day of highschool. I had spent a week out of town on the East coast and had already missed the first three days of school. I had my class list, books and the usual items and went to school. School was kind of a bore during the day. Finaly 8th. period came along. As I was aproac... Read full Story
shemale lover 2012-04-26 2,841 Fetish gangbang domination assfucking
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 8,044 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
50%
The First
When he finished with the make-up and donned the breast-length brunette wig with the bangs-- that was it. He felt the skirt against his cock and his lap. He liked the way his thighs looked with the eight inches of red and green plaid covering his "secret." He picked a tight black Slayer sh... Read full Story
shemale lover 2012-06-21 2,248 brunette Fetish wig
100%
Blame Abba
Transgender-themed stories which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** Part 1 - Well, I knew I was bound to be caught one day .... *** Thinking back - wow! So much, in such a short time, or at least it seems like that. Whe... Read full Story
shemale lover 2012-07-17 4,186 first time Stockings Fetish crossdressing
70%
A Sissies Humiliating Confession
This is a real life situation that happened this past weekend. I am sissy slave jennifer and i am owned by my beautiful Mistress Rita. Mistress Rita loves nothing more than putting this pathetic lil sissy through the most humiliating situations She can get away with. I once confessed to Mistress tha... Read full Story
shemale lover 2012-08-02 5,489 Fetish domination sissy
80%
Office Policy
“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... Read full Story
shemale lover 2012-08-30 8,531 anal ass sucking threesome tits fingering sex blondie
100%
Double Take Chapter 2
For those who missed Part I, the players are: Sandy Lane, pro surfer with an uncanny resemblance to... Ashley Vaughn, gorgeous Hollywood starlet in a TV series produced by... Darla Palmer, who convinces Sandy to bob his nose after he is punched out by rival surfer... Buster Cruz, whose m... Read full Story
shemale lover 2012-11-03 3,911 Fetish Lingerie Sex Toys
100%
What Price Desire
I stood in front of the imposing door, my hands visibly shaking, my mind running rampant, my thoughts a jumble as I opened it. The front of the building had only the number of the business adorning it, no letters, no writing, nothing to indicate what it was. Now that I think back on it, I can unders... Read full Story
shemale lover 2012-12-14 4,523 Fetish domination
52%
Sister seduces tranny brother for sissyfication
My big sister used to buy me fags if I massaged her feet & legs I loved it constant aching hard cock the whole. Time. Slowly moving up her nylon clad legs She. Stood all day at her work and it became a ritual I'd be oozing precum well B4 I caressed her kneeknee and my hand disapea... Read full Story
trannyintights 2014-05-15 9,081 Cumshot massage foot fetish footjob feet
88%
LONDON CINEMA LIAISON
When I lived in London back in the 80s and 90s, I would often sneak off to a porn cinema with stockings, suspenders and knickers under my suit. My wife didn’t much like sex, so this was a release for me to get away from home and have some sexy fun. Once I had found a suitable seat I would ease down ... Read full Story
GinaG 2018-12-14 7,137 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
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 11,248 Crossdresser Fetish pantyhose Mature pantyhose cd
100%
One night in the bathroom...
I had just recently moved into my own place and was getting warmed up to my palace.. I say palace because I never deserved such a beautiful posh lifestyle.. I'm so proud of my working skills, so I guess I deserved it.. I used my mouth you might say... I began my "job" when I first began fr... Read full Story
shemale lover 2011-11-29 2,579 Stockings sucking Fetish
50%
Sadopsychorama
He liked Clyrissa. She was a cock-hungry female if there ever was one. At 5'5", she had platinum blonde dyed hair, big tits, and a tight waist. She was a hot lay. But the best thing about her - the thing that stiffened his cock whenever he saw her was the fact that she was 53 years old. Somethi... Read full Story
shemale lover 2011-12-24 3,822 Fetish shemale anus
100%
The Neighbor
My awakening into the wonderful world of femininity came about so easily and yet so innocently. Who would have ever thought I would have been introduced to the complete feminization by someone as wonderful. I was so lucky to have found a neighbor like Melissa. As I gaze upon her as she silent... Read full Story
shemale lover 2012-01-14 4,838 Stockings Fetish feminization
100%
The Mole
Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practi... Read full Story
shemale lover 2012-01-26 6,590 brunette Crossdresser Fetish
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 7,532 anal sex Cumshot oral sex wanking cum swallowing
88%
Crossdressing with my moms friend
Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed. after 10 or so seconds she closed the door and walked away. i was mortified. i was kneeling on my bed, with her clothing catalogue open at the lingerie section laying on the bed before me, hard cock in h... Read full Story
shemale lover 2012-06-12 11,832 Stockings Fetish cum crossdressing
83%
Black Love: Transsexual Edition
My name is Steve Vincent. A big and tall young Black man living in the city of Brockton, Massachusetts. Currently, I'm a graduate student at the University of Massachusetts in downtown Boston. When I'm not in class, I work for the Department of Corrections. I'm openly bisexual, and love to have fun.... Read full Story
shemale lover 2012-06-27 4,099 anal sex Creampie Big Cock oral sex Interracial
50%
A Turkish Delight Part 4
The Vice Regal Ball was winding up as I made my way back to the main ballroom and to where Anwar stood smoking his cigar and looking to see where his new toy had disappeared too. As I approached him I knew that I was in trouble as he stood with a steel stare as I made my way to him. I hoped that he ... Read full Story
shemale lover 2012-07-16 2,224 Fetish domination oral sex
100%
Office Casual
"Good morning Ms. Anderson," Karen said as her boss walked past her desk station and into her office. "Good morning Karen," Ms. Anderson said, not even stopping to make eye contact, "I'm going to be very busy today, so I'll need you to let me know if you get any mail fo... Read full Story
shemale lover 2012-08-30 3,885 brunette cock Masturbation Blowjob shemale big
100%
R Is for Rita
After my debts began to mount, college fees and all that, one of my mates from Brum suggested I try to earn a little extra cash. I was surprised when he told me how. He said he'd done it and ended up with a couple of hundred extra most weeks, sometimes just for an evening's work. "It's easy,... Read full Story
shemale lover 2012-09-05 5,332 Stockings Big Tits Masturbation Big Cock Mature
100%
Becoming Aphrodite
My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettabl... Read full Story
shemale lover 2012-11-01 4,178 Group Sex cum oral sex cum swapping
100%
Double Take Chapter 3
Sandy and Ashley switched off the television and stared at one another in disbelief. Normally, they didn't stay up to watch the network telecast of Wet Girls, which came on at 10:00 on the west coast. After all, they had to get up at 5:00 the next morning. But they knew the entire country would be t... Read full Story
shemale lover 2012-11-03 3,137 Stockings Fetish feminization
100%
Fun With Kelly
As soon as they’d said “hi” to each other, he told Kelly that he had plans for her that day. He didn’t wait for her to say no, or say I’d rather do something else, or say anything at all, for that matter. He just told her he wanted to take her shopping, and she didn&rsq... Read full Story
shemale lover 2012-12-13 3,459 Fetish orgasm Lingerie
33%
Old Folks Chapter 1
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 2012-12-21 4,288 Stockings Crossdresser Lingerie Mature cd
81%
Cutting Ms Betty's Lawn
My mother had suggested I might consider cutting Ms Betty's lawn as none of the other boys in the neighborhood would. All the other mothers hated Ms Betty and wouldn't allow their sons to associate with her. She was one of my mom's friends and I thought nothing of it, so I agreed to d... Read full Story
buttguy 2018-01-16 27,186 Teen (18+) Blowjob transsexual Lingerie Mature
0%
girls need a daddy
Friday July 18 Hello daddy, I have arranged to meet a man next week and we are in 'phone contact. He is coming to visit me and I just need to tell him whether Wednesday or Thursday. I haven't done this yet as once done is done .... I know he wants to take photos of me but I don't know if ... Read full Story
amberdoll 2020-07-22 3,232 Stockings Small Tits Crossdresser Amateur blonde Lingerie Homemade
50%
SUBMISSA, ADESTRADA E BEM ALIMENTADA POR UM MACHO DOTADO parte 1
SUBMISSA, ADESTRADA E BEM ALIMENTADA POR UM MACHO DOTADO Ha alguns dias atras, quase antes de começar essa coisa toda do Coronavirus e do povo ficar isolado em casa, eu tava voltando pra casa, já umas 11 da noite. Meu onibus, o ultimo, ia demorar ainda pra passar, não tinha ninguem na rua, tudo f... Read full Story
Anymelzinhacd 2023-07-04 899 anal Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie domination sissy femboy Ass to Mouth cum in mouth
50%
The first requirement of a deal with Dominatrix Persephone.e
There was a number of requirements before I even consider'd fucking that sissy ass, firstly, I expected dedication to be shown and to prove that the sissy could obey my orders, after a trial period, then I consider to force my big dick down the throat of the that sissy, and then fuck brutally and ex... Read full Story
Dominatrix Persephone 2024-06-21 1,888 anal solo Cumshot Masturbation Shemale Fucks Guy Big Cock Shemale and Girl domination Mature sissy shemale fucks shemale teen (18+)
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 13,621 anal Fetish transexual
100%
A cum slut is born
There's little doubt about what turns me on most -- just check out my favorite videos and photos. Cum, Cum, and more cum. I'm a late bloomer as far as discovering my kinky side. After a long, dull marriage consisting of vanilla sex, I got divorced a few years back and decided to explore some fantasi... Read full Story
shemale lover 2012-03-16 3,637 licking Fetish stroking
100%
Bike Shed Rendezvous
Chapter 1 A meeting you can't refuse The sun is shining brightly, but the ground is still damp from the morning's rain and the air is very cold. It's lunch time and you quickly walk across the College car park to the sports pavilion. Becky your sweet heart has told you to meet her and she's been ... Read full Story
shemale lover 2012-06-11 3,233 Fetish oral sex crossdressing sissy
100%
Caught by the Past
Your latest girlfriend, Karen is very kinky and she introduces you to all manner of strange people. You on the other hand are rather naive and innocent. You found one handsome guy, James strangely attractive. He has long muscular legs, a washboard stomach, dark skin, blond hair and an impeccable spe... Read full Story
shemale lover 2012-06-28 2,569 Stockings Fetish crossdressing
100%
Fantasy Reversal Chapter 3
Gentle reminders of my first orgasm continued, until the shower water was no longer warm. It seemed like I had been there for an hour. As I looked down again, the female body I saw was not what I had hoped for. My cock was not there, I was in her body, the body of Katrina, my wife. What had she done... Read full Story
shemale lover 2012-06-29 2,602 first time Cumshot Fetish crossdressing heels
100%
Fantasy Reversal Chapter 7
As this was to be my final day and night as Katrina I awoke early. Sam was still in bed as I pulled my hair back into a pony tail and dressed in my running shorts and sports bra, I stopped a moment to admire how I looked. My hands roving my own girlish body, gently feeling my curves. Finding, to my ... Read full Story
shemale lover 2012-06-30 2,728 Fetish Blowjob oral sex crossdressing
100%
Sissy For My Flatmate Chapter 2
If you've only just tuned in, here's what's going on in my life. Until recently I was a closet crossdresser trying to keep my hobby from my flatmate. When he caught me in the act, I found out that not only had he known about me for a long time but it was a turn on for him. I agreed to become his sis... Read full Story
shemale lover 2012-08-12 3,764 oral sex cum swallowing sissy
95%
T-Girl University
Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for ... Read full Story
shemale lover 2012-09-05 14,864 Cumshot Masturbation Blowjob ass licking redhead
100%
My trip to Mistress Cindy’s House – Pa
Cindy and I had worked together for years. We had been peers for several years and became good friends, then I became Her manager. Our friendship continued but many coworkers were certain we were having an affair. We weren’t having an affair, but ate lunch together nearly every day and shared ... Read full Story
shemale lover 2012-09-12 6,451 Fetish domination sissy
100%
Panty Corset Pleasure
So ive caught you. I spun around and there was my wife. I was wearing black lace panties a Black Bra and a Red silk dress. I knew you was doing this, thats why my best knickers are getting stretched. Get changed and I will wait in the car for you. We went shopping and I tried to talk but was shushed... Read full Story
shemale lover 2012-10-26 2,889 first time shemales Fetish
100%
Working hard
My name is Micheal my birth. But I am known as Michelle As a child I had began cross dressing at around ten years age. I had actually been allowed to pick out and wear anything from my mother's closets and drawers. I was a very feminine boy and was often mistaken for being a little girl.My mother un... Read full Story
shemale lover 2012-11-06 3,097 Fetish crossdressing long cock