Sort by
Relevancy

Free Stories

100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 4,662 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
91%
Finding Mother
Nana moved in to the apartment next to me for about a year ago. She was stunning. Mature, tall and voluptuous with long red hair. Always in high heels and seemed nylons. Always with a little too much make up. And a lot of perfume. We didn't talk that much in the beginning. We would meet in the stair... Read full Story
shemale lover 2012-02-13 4,917 Mature nylons
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 26,904 Teen (18+) Blowjob transsexual Lingerie Mature
90%
White dress!
It had been a long and hot day that sunday! Some friends opted the idea to go drinks and have a cookout, little did i know how the night would end. By the time it got to midnight we were all drunk and wanted more action so we decided to head to one of the local bars for more drinks and see if we fo... Read full Story
PeterPiper 2018-03-22 5,900 Masturbation Bareback Mature Ass to Mouth cum in mouth
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 6,827 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
29%
Me
I cum here to lopk at all the beautiful shemales I can find. Damn, theres 1,000s I want to wank or enjoy to. Theres not just one kind I want to fondle and cuddle with. But too many to see all. How to choose? Gotta be a trans, transgender, ladyboy, shemale.... Have some tits baby. Large cock is al... Read full Story
Str8guy4u 2019-11-22 4,193 Big Tits Latina Shemale Fucks Guy Blowjob blonde Big Cock Ladyboy masturbating Mature Vintage shemale + shemale Date hot fun 1st timer
92%
Southern Hospitality Ch. 04
XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... Read full Story
Gwapo67 2022-05-16 6,430 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature cum in mouth
100%
CONTES DE FEMMES TRANS TOPS ⚧️ ⚧️
Être coincé au bureau tard un vendredi, c'est toujours nul. Alors que je remarquais que des subordonnés et des collègues quittaient le bâtiment alors que l'horloge sonnait cinq heures, certains d'entre eux s'arrêtant à la porte de mon bureau pour me souhaiter poliment un bon week-end... Read full Story
Femboy 2021 2023-03-19 706 Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth transexuelle
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 1,362 Shemale Fucks Guy Blowjob Big Cock Ladyboy Guy Fucks Shemale shemale fucks shemale Fantasy Tale
50%
My first threesome
My lover and I just finished sucking each off and were laying next to each just talking and he ask if I had any fantasy's and I said I like dressing in lingerie. He went to his closet and came out with a black bra and panty set along with a full black slip. He asked if I would put these on and I was... Read full Story
shemale lover 2011-08-22 2,296 shemales oral sex Mature
100%
The Ball Game
Dad and myself had not had any "Barb" time in quite awhile. We never played when mom was around and needed some time together. A "boys" trip to KC would be just what we needed! Soon as dad got home from work we headed for KC. He had put my stuff in the trunk and when got a way... Read full Story
shemale lover 2011-12-07 2,074 anal shemales Mature
50%
Mature crossdresser & 18 year old Part 2
After we sat on the couch a few minutes kissing he whispered in my ear he wanted try licking my boy pussy.I said yes an postion myself so he could, for a boy that never done anything sexual before he speard my cheecks and started to lick and kiss my hole.Then he buried his face and tongue deep in my... Read full Story
shemale lover 2012-04-12 2,455 Cumshot fingering rimjob
100%
Leila My Hermaphrodite Lover
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at a friend's house and after a ni... Read full Story
shemale lover 2012-12-17 3,953 taboo Cumshot shemale Mature
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,485 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
77%
im a cd slut
i started dressing about four years ago and i love it. it turns me on to see the guys watching me. to know that they are thinking about fucking me. i loved it. so i called a friend that i knew was gay and we couldnt wait to get together. it was on. i was invited to his house for drinks and a dip i... Read full Story
jenny green 2022-06-17 7,621 Crossdresser Bareback Lingerie Guy Fucks Shemale Mature
100%
Barbara & Vikky Part 2
One day, after ue were some months into our relationship I received a perturbing phonecall. It was Vikky in tears after one of her new guys had dumped her. I listened disinterestedly, just happy inside to consider which colour thong I should buy Barbara for an upcoming dressup session, and how she'd... Read full Story
shemale lover 2011-11-02 2,339 shemales Masturbation Mature
50%
My Fantasy
This dint really a sex story, more of a plan I would love to find someone willing to play with me. I would like to find a women who has a plumbing problem call me and ask me to come over and look at her problem, she would meet me at the door, wearing a robe tied at the waist, as she shakes my hand I... Read full Story
shemale lover 2012-01-03 2,114 first time shemales Mature
91%
Mature crossdresser & 18 year old
Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother he... Read full Story
shemale lover 2012-04-12 11,227 Crossdresser Cumshot oral sex
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 3,187 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
Chrissy Tunnell 2022-12-01 3,405 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Barbara and Vikky Part 3
In my mind's eye, the scene was as lurid and downright perverted as anything constructed by any artist or photographer: a confusion of golden curls, shoulders, thighs, tongues and pulsing cocks. The sound was a low, constant mesh of breathing and moaning, grunting and sighing: a languid, private mon... Read full Story
shemale lover 2011-11-08 1,637 shemales Masturbation Mature
100%
janine 2
After my epiphany, after my fainting, after my two near consecutive, mind melting orgasms, I was ready to meet the world with new resolve. No longer would I keep my true self under wrap. I was ready to become Janine, however I was going to have to be cautious, for the time being anyway. The first th... Read full Story
bunny cat 2019-02-08 3,423 solo Masturbation Sex Toys Mature
100%
Sissy gets her Prezzie
Justina woke up on Monday morning and was already tired, she had been dogging till 3 and her little ass was a little bit sore. She made her way to the bathroom and had a pee, brushed her teeth then headed for the kitchen to make coffee. As she was walking her phone went off, she had a text from ... Read full Story
Samantha Jewels 2022-01-06 2,946 Stockings Crossdresser Cumshot Bareback Blowjob Big Cock gangbang domination Mature Homemade Ass to Mouth
50%
Not your usual birthday present
So here we go again “Happy Birthday” to me, at 51 it’s not that great really it’s just a reminder your getting older!! Anyway here I am 51 having an absolute ball and fulfilling my wildest dreams, Justina likes being out of the closest and loooooves cock.. So for her birthday she hopes someone has ... Read full Story
Samantha Jewels 2022-01-12 2,593 Stockings Crossdresser Amateur Blowjob Big Cock gangbang Lingerie domination Sex Toys Mature 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 3,768 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,344 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Captain John’s Playmate
Alessia Travestita’s Adventures – Episode 1 – Captain John’s Playmate. It was forecast to be a gloriously warm and sunny day, clear blue skies with a gentle warm breeze from the South. So I decided to leave the town behind and head out into the countryside for the day, get some fresh air, toning ex... Read full Story
Alessia Travestita 2023-07-13 4,328 anal Crossdresser Bareback Blowjob blonde Big Cock Lingerie Guy Fucks Shemale Mature Ass to Mouth cum in mouth
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 4,323 Masturbation Creampie Blowjob Big Cock Ladyboy Mature small cock sissy cum in mouth
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 4,535 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
The Ball Game 2
I awoke the next morning to dad's cock fucking me from behind. He held me tight as he pumped my ass gently. He gave me a sweet kiss and said he needed to use the bathroom and I was to accompany him there. He told me to step into the shower and he followed. I braced my hands against the wall and he e... Read full Story
shemale lover 2012-01-31 2,064 anal shemales Mature
63%
They shaved me and put me in make up
Having crossdressed enjoying all the nice feelings of being a CD for many years.Katie is used by my longtime female partner as my name and she enjoyed me as a small cocked girlyboy as well as a now mature father ! It has now just happened somehow so quickly but in a blink of an eye it seemed to pu... Read full Story
katieboy52 2013-06-04 5,321 Crossdresser threesome domination small cock cd
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,189 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
94%
My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
Betty D 2021-01-18 8,131 first time Crossdresser Amateur Cumshot Fetish Blowjob Mature Homemade mini skirt small cocks black panties obese
100%
Quick trip to the park
Monday Morning again, I hate Mondays, why can’t the week start on Tuesday! Thought Justina ,while she stood semi naked in the kitchen drinking her coffee with a semi. I finished my coffee and made my way to my bedroom to get dressed. As I entered my bedroom i spotted my new dress i’d bought on S... Read full Story
Samantha Jewels 2022-01-12 2,117 Crossdresser Amateur Cumshot Outdoor Blowjob Mature crossdressing Ass to Mouth cum in mouth crossdresser amateur
50%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 3,498 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
85%
My Cock Dream
My name is Iris Cal. A few weeks ago, I had a dream. This is an account of that dream, with some holes and details filled in by my own fantasies. From what I remembered as I tried to write down as much of the dream as I could, I had woken up in the house in which I lived when I went to high schoo... Read full Story
shemale lover 2016-04-14 4,770 shemales Masturbation Fetish
69%
Shemale Video Galleries And A Cock To Bang
I arrived in Bangkok one early afternoon and I was ready to experience the thing the place was famous for. As soon as I checked in my hotel and got in my hotel room, I started searching for some hot encounter through shemale video galleries. They were all really pretty and promised a lot of fun. ... Read full Story
shemale lover 2016-04-20 4,070 first time Big Tits shemale
100%
When She became He
A Good Friends Advice "You need a good massage" You know how it is, when everything is going so well, the only way to go................, is down. Let me explain. It started when I just knew I had to dump my boyfriend, even that was a loose term. The first part was true, in two w... Read full Story
shemale lover 2011-09-12 3,300 shemales sex humor Mature
71%
Becomming a Sissy Slut
Sandy's Life My name is Sandy Johnson. I chose that name 35 years ago because I like Sandy and I knew a hot female with the last name Johnson. I first remember finding my mothers underclothes in the bathroom closet. We she and my Dad would go out I could go in the bathroom and put her slip on and f... Read full Story
shemale lover 2011-09-26 3,899 shemales Masturbation Fetish
66%
Daddy's little bitch
As a young boy growing up I always had a fetish for dressing up like a girl. When I was 20yo I had my first experience with an older man, Tony a man in his 70s. I met him through a phone chat line and we seemed to hit it off right away. He told me that he would buy me some clothes and lingerie to we... Read full Story
shemale lover 2011-10-25 4,934 shemales gay male sucking Mature
100%
Mel and me in rochester!
The musical orchestra Mel and i are in had a performance in Rochester ,New York and i needed someone to share a room with at hotel. Mel was the first person who came to mind,and since blowing him last time i thought i would ask him. Mel told me his wife wouldn"t be going and he would love to sh... Read full Story
shemale lover 2011-11-24 2,132 shemales Fetish Mature
66%
The Night With A Transgendered Angel
Her name was Steph. She stood about 6'5 in her heels. She was white very mature she was 50 years young. She wore a blond wig with seductive red well manicured nails. Gorgeous for her age,tall and slender with b cup natural breasts she developed from hormones. When I thought it couldn't get any bette... Read full Story
shemale lover 2012-09-21 2,613 anal oral domination black cock
100%
Double Wedding
I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years ... Read full Story
shemale lover 2012-11-08 7,006 Cumshot dildo Sex Toys
75%
Friends United
I'd been best friends with Brad since coming to the US from England as a child. We met at school and since those early years did everything together. He was very outgoing whereas I was passive. Now in our thirties we are still best of friends and even work in the same company. Brad loved motorcycles... Read full Story
shemale lover 2012-11-30 4,764 Fetish dildo Sex Toys crossdressing
96%
Caught
This is how I got caught masturbating and lost my virginity to my stepmom. I was still in High School but had just turned eighteen, and was still living with my dad and stepmom, Beverly. I was ashy kind in school and did not get many dates, this lead to lots of jacking off. I did not realize it at ... Read full Story
shemale lover 2012-12-17 10,617 anal taboo Masturbation oral Mature
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 4,051 Stockings Crossdresser Lingerie Mature cd
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 5,881 first time Crossdresser Fetish Mature bisexual
72%
Learning to appreciate the small things...
So...Here I am. 33, transgender, & living as a female for almost two years now. It's been a strange & crazy trip up until this point, but I learned countless valuable lessons through all of my mistakes. For instance, I learned that size truly doesn't matter in the end, because it i... Read full Story
Jewelina Fyer 2015-12-20 4,248 shemale small cock transgender ts
60%
The first day of a sissy bitch
She's preparing to become a sissy slut First long and extensive showering then a total shave and she started to turn into the femme of a sissy slut. Naked in front of the mirror, she applied the foundation and spread it evenly across all areas of her face and neck. Next she slipped into her b... Read full Story
sqimyetxräa52 2017-12-19 9,023 Crossdresser Amateur Blowjob Mature cum in mouth
66%
Awesome day at class =)
Sooo i'm in college. and one of my professors is really hot. he's older but looks like he's in his 30's. anyway, every single day in class i would notice his huge bulge under his pants and just couldn't help but wonder =P so i figured, hey maybe i should start flirting with ... Read full Story
Amanda Lips 2018-03-02 3,220 Teen (18+) Mature Homemade pov Ass to Mouth cum in mouth webcams
84%
Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
Zöe from Kingston 2018-08-09 8,951 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature cum in mouth
80%
Amber
The summer after high school I moved into this cheap hotel downtown. I'd been working in the mailroom for a large company, and really needed to get my own place, but I didn't have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I ha... Read full Story
ambersissy 2021-04-23 5,153 Crossdresser Amateur Big Cock Guy Fucks Shemale Interracial 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 3,848 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,322 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,385 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Mommy, can I be your fuck-toy?
I saw my step-mom taking a shower by accident or so I thought. It was not until I saw her pretty big she-cock jus hanging there between her sexy well defined legs. It was even hard & it was already as big as my cock when its hard. It looked so big that it was a bit scary yet some muscle in my anus s... Read full Story
Curious_billy 2022-11-22 6,862 Amateur Cumshot Masturbation Bareback Shemale Fucks Guy Blowjob Big Cock Lingerie Mature Homemade Ass to Mouth cum in mouth seduction
100%
Sweet Stephen Wears A Slip.
Stephen is a 'petite' boy, just a little smaller than his Aunt Melanie. Petite figures ran in the family in both the females and males. Stephen cut quite the girlish figure in his Aunt Melanie's pastel-pink full slip. 'Oh, my, don't you look just so simply darling, pretty missy!" Melanie cooed, ad... Read full Story
ALEXEAMES 2024-01-14 4,587 Stockings Crossdresser Amateur blonde Lingerie Shemale and Girl small cock sissy femboy teen (18+)
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 5,706 solo Lingerie small cock Homemade sissy femboy
100%
Dress-Up-Girly Time!
"Let's go, 'Little-Missy,' it's our 'dress-up-girly time.'" Sandy knew better than to argue. Besides he really didn't mind being dressed up as a girl. It was kind of weird at first, when he first started playing 'dress-up-girly time.' His mom had brought home several boxes of clothes that no lo... Read full Story
ALEXEAMES 2024-01-27 4,732 Crossdresser Amateur Lingerie small cock Homemade sissy femboy teen (18+)
100%
Amy The Tranny Part 1
I met Amy at an adult theatre in town. She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private booth and once inside, went over her price for some adult fun. She told me I couldn't fuck her as she was on her per... Read full Story
shemale lover 2011-12-14 4,630 shemales hardcore anal sex Big Cock
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,081 torture extreme fiction bondage and discipline
50%
The Greatest Lie Part 6
In my rare moments of leisure in the weeks following my close encounter with death, I had had little opportunity to talk about it. Of course, the police had asked perfunctory questions, and I had testified at the coroner’s inquest, but until my next appointment with Dr. Erika Wright, I had not... Read full Story
shemale lover 2012-01-19 4,351 hardcore erotic encounters fantastic
83%
The Making of A Sissy Part 12
Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... Read full Story
shemale lover 2012-05-31 4,159 anal Fetish little cock sissy
100%
Finishing School for Shemales Chapter 2
Davina hurried down the hallway, her books clasped in front of her heavy breasts to stop them jiggling as she ran. It had been almost two weeks since she had truly given herself to Mistress K in the beautiful, imposing headmistresses study, drinking the transgendered woman's seed from another T-g... Read full Story
shemale lover 2012-08-09 6,149 cum fingering little cock
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 6,259 Fetish domination sissy
70%
First Time Sissy Maid
I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... Read full Story
shemale lover 2012-10-27 16,599 first time Fetish Big Cock domination sissy
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,331 Masturbation Blowjob blonde ass fucking big boobs
76%
Louise's Bedroom
The dark and humid night consumed the street surroundings, the rain pattered softly against the car window as Scott pulled outside Louise’s house. Louise had never agreed to let Scott visit before and he knew that this would be the only opportunity to make a good impression and be with her in the fu... Read full Story
Master VeeJay 2017-12-12 9,265 Amateur Bareback Creampie Blowjob Guy Fucks Shemale Mature
72%
DENISE IN BLACK FF NYLONS AND HEELS
I have a passion for corsets and black fully fashioned seamed nylons, which I like to wear with tight revealing tops and miniskirts or very clingy dresses. I always wear multi strap 10 or 14 suspenders with a tight lacing corset that reduces my waist and gives a sexy outline to my shape. My favou... Read full Story
DENISEFFNYLONS 2018-04-03 7,871 Stockings Fetish threesome gangbang Lingerie Mature cum in mouth
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,635 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
100%
Taking Ricky's Cherry
My work has me traveling all over the US and if you have read any of my previous stuff then you might have figured out that I have a major cougar streak. I just love being the first T gurl to a sexually inexperienced young guy. I was bored and horny in the hotel room, so I logged into a gay dating s... Read full Story
pennypenny 2019-06-11 8,131 Stockings Teen (18+) Crossdresser Cumshot Bareback Creampie Fetish Blowjob redhead Guy Fucks Shemale Mature Ass to Mouth cum in 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 10,948 Crossdresser Fetish pantyhose Mature pantyhose cd
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 7,507 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
100%
A Boy and Laura
Jonas was in a hotel enjoying the last days of his vacation in Cabo Frio, Rio de Janeiro. Sitting at the bar drinking an orange juice and watching the landscape, he saw a woman approaching, wearing a purple bikini that made up her breasts well, but kept her waist covered by a flowered thong that als... Read full Story
haroldãosanguebom 2021-08-17 7,073 Shemale Fucks Guy Blowjob domination Mature
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 3,498 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,452 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
My Love Letter To Joanna Jet
I await my goddess on my knees, my heart pounding in my chest as I hear the sound of your footsteps outside my door. You knock and I spring to my feet, opening the door. You enter, pushing me aside and closing the door behind you. You are radiant, tall and curvy, with long black hair, smooth cara... Read full Story
TgirlLover4Life18 2022-04-12 2,040 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy blonde Big Cock Lingerie Mature Ass to Mouth
100%
Alessia and I shock our guest!
Alessia was sat on the couch and I was sitting on the soft fur rug between her legs. We were relaxing and recovering watching an old movie. My ass was still feeling hot and wet after Alessia had earlier fucked me hard and long and I had returned the favour to her. But that is another dream! So back... Read full Story
Alessia Travestita 2023-01-12 4,310 Crossdresser Blowjob blonde Big Cock Guy Fucks Shemale Mature cum in mouth
93%
MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
darrell 2023-08-13 5,860 anal Cumshot Shemale Fucks Guy Fetish blonde Big Cock domination Mature deep throat cum in mouth sandals
100%
MILF Alessia Travestita finds a bottom boy pt 2
Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... Read full Story
darrell 2023-08-13 5,702 anal Shemale Fucks Guy Fetish Blowjob blonde Big Cock domination Mature deep throat cum in mouth sandals toe sucking