Sort by
Relevancy

Free Stories

69%
February 2nd
February 2nd. My first time being fucked in my ass. It was unbelievably satisfying but I want more. I was on a dating app for guys looking for guys. I was just curious never thought that I'll be longing for a dick in me. My first was so-so.. the 2nd time just a few hours after my first was fantasti... Read full Story
Princess Raven 2020-02-06 4,313 Crossdresser Amateur Blowjob Big Cock Asian domination Homemade
100%
My story; don’t know which one... English version (1)
I notice that the're not many french language readers so have I decided to publish an English version End of the 80s; a tough time for a young reporter travelling thousands of km's for a crumb of titbit. A new event and more pressure every day for me. Seeing me in this floundering state during a ... Read full Story
hippocampus_171 2022-07-21 3,447 Small Tits Crossdresser Amateur Bareback domination Sex Toys Mature Homemade
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 5,415 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
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 3,323 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
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 4,900 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
100%
The Married Man of Summer #1
The Married Man of Summer #1 By Sabrina G. Langton *** Something quick.. something from a nice quiet neighborhood, I hope YOU like it... *Stories from the real world This story is slightly, slightly, very slightly autobiographical. Ha... *** Between the beginning of summer 1987 and th... Read full Story
Brina Giselle 2024-02-03 5,111 Crossdresser transgender blowjobs dress
100%
MY First Time with a non-binary/cross-dresser
After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... Read full Story
ghostpeople 2019-03-12 6,945 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
100%
Emily's First Daddy
This is a story how a curious male can become a sissy slut seemingly overnight. So I was in an online adult chat just talking with random people and happened to mentioned where I live. Then all of sudden, I got a message from a man calling himself bear daddy. He introduced himself and said he was ... Read full Story
User Removed 2019-10-21 8,825 Crossdresser Amateur Creampie Homemade cum in mouth webcams
100%
Groped on the Bus
In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... Read full Story
Chrissy Tunnell 2023-03-17 4,927 Crossdresser Amateur Masturbation Ladyboy Guy Fucks Shemale Frottage
62%
My Brother and I.
HI, I am Farzana,(have set my name recently,before that my name was Raja). I am Bangladeshi. I have been leaving with my family.Now I live with my Dad only.Some times, He invite his friends also. I will tell You about this later. I am 27 years old.The story I am sharing with You is about ...14 year... Read full Story
Esrat 2019-11-26 9,456 Crossdresser Group Sex Cumshot Creampie Fetish Blowjob Big Cock Asian gangbang domination Homemade cum in mouth
73%
How I got started dressing
I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just u... Read full Story
bigtranslover 2014-02-09 7,476 first time shemales Masturbation
58%
Preggo Scat Sex
Sara was horny. For any type of sex. She was stuck on a bus heading to her school. After 14 years of wasting her time She discovered her own sexual abilities.She had her first practice by fucking her brother's friend. She didn't come to school to learn. She came to screw anyone in sight. She had ... Read full Story
shemale lover 2012-01-07 12,001 Masturbation lesbian peeing
92%
A Surprise Relationship
This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony&quo... Read full Story
shemale lover 2013-01-29 5,235 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 2,688 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
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 4,880 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,222 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
68%
Next time fucking her cross dressing husband and bred his wife
Wachenheim dressed up in a pretty skirt and loose blouse with his wife watching walked up to and knelt between my legs. He sucked my thick long black cock. His wife watched and masturbated as he worked my cock deep in his mouth. She knew as soon as I did him that she ws next. It was her wishes for t... Read full Story
Rocky Wachenheim 2014-09-23 4,389 Crossdresser suck Masturbation Big Cock cd
90%
Fortunate accident part 4
I reëntered the room clad in a g-strip and bra; I wore eye make up and lipstick with a long blue wig that covered my left eye with one of the bangs. I popped my hip and tried to lean seductively on the doorway --something I, admittedly, had not had a whole lot f practice with. She looked out at me a... Read full Story
Jenna_NB 2016-04-28 3,349 Crossdresser facial cock sucking strap-on sissy
95%
Jordan's First
My name is Jason, I am a 33 year old road worker. The pay is okay but I never had much more than what I needed to live comfortably. I was hoping to save up for a nice vacation and decided the best way to do that was to take on a roommate. I live in a decent sized two bedroom apartment and the seco... Read full Story
Hydra1979 2019-01-25 9,579 Stockings Crossdresser Masturbation Blowjob Lingerie
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 3,727 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
93%
Sissy Maddie's New Apartment Gangbang
I’d just moved into the big city. Me on my own in a cheap apartment block. The flat was nothing special by any means, and the room next to mine seemed to be noisy with parties. But I was glad to be on my own. I had almost finished unpacking my belongings when I came across my stash of female clothi... Read full Story
sissymaddiex 2020-09-25 9,841 Crossdresser Amateur Group Sex Cumshot Bareback Creampie Blowjob gangbang Lingerie Homemade sissy cum in mouth double anal
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 3,969 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
Becoming Kacey
I indulged my crossdressing opportunities as often as I could, but as time went on, the chances grew further and further apart. Although I couldn't play dress up in my alone time, the fantasies never seemed to cease. When I entered high school, I dated girls and enjoyed the young passions that teena... Read full Story
KaceyKlarissa 2024-01-16 3,915 first time Crossdresser Amateur Homemade sissy femboy shemale + shemale romantic teen (18+)
100%
Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
kelliecdgirl 2024-04-10 3,226 Stockings Crossdresser Cumshot Masturbation Fetish blonde Big Cock Lingerie pantyhose Frottage sissy femboy shemale + shemale
30%
CD Delight
The following is an account of a true encounter between consenting adults. The names and places have been altered to protect the individuals. Any resemblance to actual persons is purely coincidental. It is not intended for minors. If you are offended by sexually explicit material or have receive... Read full Story
shemale lover 2012-01-27 3,211 sucking cum Sex Toys cd
94%
The Accidental Sissy
My girlfriend and I live in an apartment in small town in Texas. She a good looking 31 year old babe with a great body and sex drive to match. My girlfriend, Suzy is full figured but not fat, just a big girl and I love every inch of her. Me, I'm 6', 185, starting to put on a little of that middl... Read full Story
shemale lover 2013-01-04 10,037 Crossdresser Cumshot Masturbation jerking Lingerie
95%
Dana becomes a woman
All her life, Dana had felt different. Born a boy, she always preferred dressing in girl clothes and playing girl games. She was mistaken for a girl from the time she was toddling - her feminine face and manner always convinced people. By the time she graduated high school, Dana discovered her ma... Read full Story
shemale lover 2013-07-20 4,577 Crossdresser Cumshot Masturbation oral sex ass fingering
100%
Maddie and the public bathroom antics
I had put on my lingerie and my dress underneath my manly clothes and was preparing myself to go to a public bathroom. The idea was to enter a cubicle, take off my boring man clothes and sit there looking like a sexy sissy where I could video myself on my smartphone. I needed some hot new pics, so I... Read full Story
sissymaddiex 2023-01-06 3,810 Crossdresser Amateur Cumshot Masturbation Bareback Blowjob Lingerie cum in mouth
100%
Working the Glory Hole
After so many nights of torrid fantasies plaguing my sleep, I took a long look at myself in the mirror. I had been slowly embracing my femininity over the past few months. My hair had grown past my shoulders, I was shaving my entire body on the regular, and I would wear panties under my guy clothes ... Read full Story
KaceyKlarissa 2024-04-15 3,814 Crossdresser Amateur Cumshot Masturbation Blowjob facial glory hole whore sissy cum in mouth sissy slut
76%
My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
shemale lover 2012-09-09 9,808 Crossdresser Cumshot Masturbation Lingerie heels
88%
Becoming Lisa
From when I was as young as 9, smooth and long blonde hair, I was always dressing in my older sister's panties and bra, panty hose. My breasts were kinda girlish and i had long nipples that would get hard when I played with them. I was older now, but still only had a small 4 inch cock when it was ha... Read full Story
shemale lover 2013-08-09 12,956 Crossdresser Masturbation Fetish Lingerie kissing
100%
The Big Tiddy Goth Girl
Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... Read full Story
KaceyKlarissa 2024-02-23 4,527 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
100%
Alex Two: The Next Time
Part Two of ??? (there is another series I'll start too, Hopefully its not too repetitive and my fetishes aren't showing too strongly. heh. That is sort of a prequel to this, I guess. I had forgotten about it till just now when I found it in a misnamed folder.) Alex Two: The Next Time.... Read full Story
AlexShouse 2012-07-12 3,146 tranny Crossdresser Masturbation
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,527 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
A New Me...
Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn't all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending. My sister and... Read full Story
shemale lover 2012-04-14 5,181 Masturbation Fetish crossdressing
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,779 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
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 6,948 Crossdresser Cumshot Outdoor Masturbation Fetish Blowjob pantyhose legs pantyhose cd
100%
Revenge is Sweet
Henry Stewart was thirty five years old, married to a very attractive woman who'd given him three kids, he owned and ran his own very successful computing company in San Diego, "Stewart Computing", meanwhile he owned a large house in the wealthy small town of River Falls. All in all, Henry... Read full Story
shemale lover 2012-09-01 7,638 Crossdresser Cumshot Masturbation Lingerie heels
83%
Discovering Amber
I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it has always gone deeper. At 18 I tried on my first set of panties, oh my God that was wonderful! It was all downhill from there. Event... Read full Story
shemale lover 2012-09-28 6,087 Cumshot Fetish Lingerie oral sex
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,163 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
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 10,897 Fetish crossdressing feminization
100%
The Bounty Hunter - Working With A Partner
My boss, Carl Bronson, was pleased with the results of my first case, and gave me more jobs over the next few months. In each, I learned from my mistakes and was able to apprehend my target. Even better, I was finally earning some good money and doing something that was worthwhile and, more importan... Read full Story
shemale lover 2012-01-29 4,367 sucking Creampie cum fucking
100%
His teacher, The transsexual
Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't a... Read full Story
shemale lover 2012-01-31 9,674 shemale Big Cock teacher
100%
Anastasia's Life
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, Barb... Read full Story
shemale lover 2012-11-26 7,099 Fetish cock sucking crossdressing
94%
The Transsexual Teacher
Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't a... Read full Story
ASSEaster5678 2019-03-18 33,849 Shemale Fucks Guy school teacher sex