Sort by
Relevancy

Free Stories

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 4,273 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 7,522 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
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 5,061 Stockings Big Tits Masturbation Big Cock Mature
71%
Trans secretary
"Monica Barnes smoothed her skirt before entering the office of her boss, Cord Drake, the CEO of the company his father had founded thirty eight years ago! Like every other morning for the past two years, she brought along his coffee, her memo pad, and of course his copy of the morning paper! &... Read full Story
shemale lover 2012-04-30 3,992 anal sex Cumshot Big Cock oral sex
100%
A secretary fantasy
I love the idea of boss / secretary fantasy, where i'm the secretary. It's one of the few places where I can dress in beautiful dresses, stockings/pantyhose, and heels. I envision a situation where the boss knows i'm a trans woman, and hires me because of it. 1 to help me out as i need a job,... Read full Story
Wendytg976 2019-05-14 4,432 cum in mouth
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 7,423 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
75%
Shemale secretary fucking
Ms Boss had said that I was to see her secretary concerning "letting of some steam". She and I had been at each others throats lately and Ms Boss didn´t like her two slaves to argue. So we were left alone in the break room after most people had gone home. And we were not to leave un... Read full Story
shemale lover 2012-03-28 3,690 anal sex Creampie deepthroating
40%
Becoming wife of competitor feminized by secretary
I am Siddharth Mittal, running my own Company with USD 100 Million of Business. Everything is going on well and I am excelling in my business. I have a secretary named Sonia. She is a smart and beautiful girl with 36-32-36 size. She knows how to get her work done. She wears simple clothes and is dec... Read full Story
shemale lover 2012-05-17 5,532 anal sex Cumshot Big Cock feminization
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,018 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 4,711 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
50%
La bonne chair masculine…
La bonne chair masculine… La brise caressait mes mamelons gonflés me donnant des frissons agréables. Les deux verres de Riesling avaient également contribué à mon excitation. Mon entre-jambe brûlait comme si le soleil qui disparaissait avait soufflé toute son énergie thermique dans mon intérieur... Read full Story
hippocampus_171 2023-04-23 701 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminization cum in mouth gaycd virile
100%
The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
darrell 2021-12-14 4,027 Crossdresser Blowjob blonde Big Cock domination Mature cum in mouth
93%
Southern Hospitality Ch. 01
XtinaSmith2017 Ash gawped at his mother, incredulous as to what she had just said. He understood the basic premise of what had happened, but the reasoning she must have had absolutely baffled him. "Why?! Why would you do that?!" He pleaded, voice light and desperate. She shrugged, looking acr... Read full Story
Gwapo67 2022-05-16 6,725 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature
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 3,916 anal shemales Mature
83%
More Than a Lady
Doctor Carter surveyed the gathering of ladies before him. Something wasn't quite right, but he just couldn't put his finger on what it was. He had been invited to speak on Female Reproductive Health but the women before him were neither the charity-driven older matrons nor eager young housewives th... Read full Story
shemale lover 2011-11-24 4,156 pissing Ladyboy Mature
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 4,908 Mature nylons
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 4,222 gay male Mature cd
100%
Olderman and mature crossdresser Part 2
We left the park and drove to his house which was very nice.I knew he was wealth when he picked up due to his car was new jag. He fixed me drink and we sat on his couch and kissed and made out an heavy petting.He kissed my neck driveing me nuts as he did I rubbed his cock thru his pants which was ha... Read full Story
shemale lover 2012-05-26 3,770 Crossdresser anal sex Cumshot oral sex Mature cum swallowing
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 26,891 Teen (18+) Blowjob transsexual Lingerie Mature
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 4,110 Crossdresser Amateur Big Tits Big Cock Mature Homemade
66%
Late bloomer and loving it
i am a mature t-gurl, 3 years on hormones, and loving the experience. i am proud to show myself to you wonderful kinky people out there, and hope to meet many. Becoming a sexy chick with a dick has been so much fun.... Read full Story
Melanie Rogers 2019-04-01 3,962 Crossdresser Amateur Ladyboy Lingerie Mature Ass to Mouth
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 8,535 Crossdresser Fetish redhead pantyhose Mature pantyhose cd
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 4,640 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
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 6,410 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature 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 4,698 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
50%
J'ai enfin goûté la bonne chère/chair
Dépucelée en bon et du forme... Chose jamais osée depuis que je goûte la jouissance par tous les sens et dans tous ses sens... Je la découvris quand elle m'a sourit en guise de remerciement pour lui avoir cédé le passage dans la superette du bled où j'étais pour affaires. Sandales à ses pieds d... Read full Story
hippocampus_171 2022-11-09 826 Small Tits Amateur Shemale Fucks Guy Guy Fucks Shemale Mature Homemade Ass to Mouth Vintage cum in mouth
100%
Tasting the good FLESH
I am no longer Virgin, en bon et du forme Thing never dared since I taste the enjoyment by all the senses and in all its senses... I discovered her when she smiled at me as a thank-you for giving her the way to the small-town supermarket where I was on business. Sandals at her feet of Cinderell... Read full Story
hippocampus_171 2022-11-10 4,565 Amateur Creampie Shemale Fucks Guy Guy Fucks Shemale Mature Ass to Mouth cum in mouth
50%
De la pucelle quinquagénaire à la mature disponible...
***Prologue - Confessions: Depuis que j’ai offert ma virginité, je me mets chaque jour un peu plus dans la peau d’une femme. Le petit bled où je vis m’interdit de m’exhiber socialement. Totefois je me suis faite une complice, mon épileuse qui me reçoit après la fermeture . Depuis mon nouveau début,... Read full Story
hippocampus_171 2023-01-11 682 Crossdresser Amateur Group Sex threesome Big Cock Mature Homemade cum in mouth shemale + shemale milfs Foursome Bi
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 4,029 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
mushrooms in all shapes and forms
Mushroom season is open! Yummy! I love mushrooms, in all shapes and forms. We were about fifteen mushroom lovers who only get together to pick mushrooms, without any other friendly gatherings! For this last outing of the season, our splendid instructor was accompanied by her cousin, who was sup... Read full Story
hippocampus_171 2023-11-24 6,025 Small Tits Amateur Cumshot Mature small cock big ass bisexual cum in mouth bald men glabrous
50%
champignons sous toutes ses formes et façons
La saison des champignons est ouverte! Miam... J'adore les champignons, sous toutes ses formes et façons. Nous sommes une quinzaine d'amateurs qui se retrouvent uniquement à l'occasion des ceuillettes de champignons sans aucun autre rassemblement amical! Pour cette dernière sortie de la saison,... Read full Story
hippocampus_171 2023-11-24 403 anal Small Tits Amateur Masturbation Mature small cock big ass bisexual Homemade cum in mouth bald
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 4,868 Crossdresser Blowjob transgender mature crossdresser gloryholes
100%
Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
darrell 2024-02-02 4,221 Shemale Fucks Guy Blowjob blonde Big Cock Mature deepthroat cum in mouth toe sucking Fisting Anal
100%
A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
shemale lover 2012-03-05 13,885 Fetish bdsm crossdressing bisexual
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,387 shemale cum ass fucking
50%
Shemale Art and Artists
Several erotic artists specialize in comic books, cartoons, or illustrations that feature buxom hermaphroditic, pre-operative transsexual (shemale), or t-girl characters. Such shemale art ranges in style from three-dimensional, computer-generated images and anime, hentai, or manga comic book-style s... Read full Story
shemale lover 2011-09-22 3,571 shemales essays romance
87%
Beginning of my Bi Life
Well It's all Started When I Was at 13 or may be 14 years old. I began to watch porn and reading porn comics and began to masturbate. I wasn't getting much privacy at my home so I was staying at my school even after my classes was over and when everyone was busy at after school Sport hours I masturb... Read full Story
Trapbomb1 2021-05-25 4,150 sucking Blowjob cum bisexual cd sissy femboy bi trap
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 6,942 fuck oral
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 3,544 Crossdresser domination prisoner prison sex Prison Bitch
83%
Elaine & Me
- Chapter One – Our First Meeting - I had two weeks to go before the final degree exams and I was working hard. Perhaps too hard, because I desperately needed a break from the hours and hours of revision. It felt like I just couldn't take in any more detail about Quantum Mechanics or Solid ... Read full Story
shemale lover 2012-03-31 11,138 sucking Fetish transsexual
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 3,644 brunette cock Masturbation Blowjob shemale big
100%
Bringing Daddy's Work Home
"Whew! I can't believe this shit." Marilyn Walker, recent high school graduate, stared into the reflection in the bathroom mirror and breathed deeply, thinking to herself about her latest situation. Here, she was standing in the bathroom of the office of some city bureaucrat whose name ... Read full Story
shemale lover 2012-09-25 6,734 Cumshot transsexual oral sex
100%
Demoted and...
1) Dinner at Riverside All the note said was "Dinner. 8:00. Riverside Grill." It was in my secretary's handwriting but I knew it must be a message from Carrie. Andrea, that's my secretary, always hated taking messages from Carrie and would only write down the most important parts. River... Read full Story
shemale lover 2012-08-17 3,352 Cumshot oral sex cum swallowing
66%
A Christmiss Story
The weekend! With my first week as a secretary finally at an end, I knew exactly how I was going to spend it: sleeping till noon, then watching football on TV while binging on bratwurst and beer. When I woke up on Saturday at half past noon, I lolled in bed for another hour before I dragged mysel... Read full Story
shemale lover 2012-02-23 4,176 transformation orgasm fingering
80%
F Is for Fiona
I drove into the store car park. Stopped in my usual place, the one which said 'MAN' in bold letters on the tarmac, short for manager of course. Just for a moment I shivered despite the warm spring weather, this was honestly the first time the incongruity of that label struck me. I pulled on the ... Read full Story
shemale lover 2012-05-07 3,845 tranny fuck heels
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,458 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
100%
Lady In The House Ch. 02
A story by Michele Nylons, Part II "She's all yours Eddie. She looks beautiful." I heard Carmel say as 'she' disappeared down the corridor, her high heels clicking on the tiled floor. Eddie appeared at the door to the cell, he stepped inside and closed the door behind him. "So what do yo... Read full Story
✘Transensual✘ 2019-01-11 4,582 Stockings Crossdresser Fetish Big Cock Uniform Lingerie domination PRISON PUNK prison sex Prisonboycum Prison Bitch
50%
Mutually Assured Attraction Part 1
Max's life sucks. His job is leading nowhere and women avoid him like the plague. On most weekends his free-time is spent drunk in bars, hitting on women that don't want his attention and ultimately passing out in some back-alley. To make matters worse, his hairline has all but receded off the back ... Read full Story
shemale lover 2011-09-15 2,838 ass nipples
75%
A Futa Futcha
This story depicts a fetish know as Futanari Fuatnari: A type of Hentai, most often depicting hermaphrodites or females with male sex organs. Also known as Dickgirls. Transformation Futa is a long standing kink of mine, though it has been a while since I indulged. The major difference is that ... Read full Story
shemale lover 2011-10-29 8,230 Fetish Futanari dickgirl
80%
Career Shift
Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one ... Read full Story
shemale lover 2012-03-06 5,521 Group Sex Blowjob fingering orgasms
100%
Lady in the House
How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended u... Read full Story
shemale lover 2012-05-12 3,789 Stockings Fetish crossdressing
100%
Birthday Present
Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrive... Read full Story
shemale lover 2012-06-16 13,887 Cumshot Fetish orgasm oral sex
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 10,728 Fetish crossdressing feminization
71%
Birthday Present Part 1
Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all abo... Read full Story
shemale lover 2013-01-18 11,060 hardcore sucking Blowjob Lingerie ass fucking
93%
The Tranny Trucker
A gust of freezing wind blasted across my face. I succumbed to worries of frostbite as I walked aimlessly along the side of the highway.\r\n\r\nThe wind of passing trucks nearly knocked me off my feet. This must have been dangerous. It\'s something I should have considered.\r\n\r\nMy parents separat... Read full Story
shemale lover 2013-07-19 6,759 Cumshot ass fucking ass licking oral sex kissing
92%
Lady In The House Chapter. 01
A story by MicheleNylons ( Man in jail is transformed to prison slut.) How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild... Read full Story
✘Transensual✘ 2019-01-11 9,204 Crossdresser Bareback Creampie Fetish blonde Big Cock Lingerie domination Guy Fucks Shemale transvestite slut PRISON FUCKBOY prison sex Prison Bitch