Sort by
Relevancy

Free Stories

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 4,362 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
50%
Sissy Acceptance *
La primera vez que vi porno interracial algo recorrió mi interior de una manera que nunca antes había experimentado, era como un hormigueo que pasaba por todo mi cuerpo….. hasta llegar a mi ano. No sé que fue lo que me motivo más si la insaciable obsesión por probar una verga negra, ó el hecho de... Read full Story
Sissycrick 2023-05-04 1,189 anal Small Tits Crossdresser Amateur Latina Bareback Blowjob Big Cock Lingerie Interracial sissy femboy e
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,514 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
75%
A Tuesday To Remember
A Tuesday To Remember It was much like any Tuesday for the last year, except when I came in my wife, Deena met me at the door coming from the garage. She grabbed my arm and started leading me into the living room as she said, “You better say yes, yes to everything.” I had no idea what she was tal... Read full Story
Setinkhan 2021-04-15 6,042 Small Tits Crossdresser Interracial
50%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 5,789 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
42%
sexy jane story
I love the idea being a crossdresser wearing women outfit bars in panties n sexy outfit not just for the sex I love sex being on my knees sucking cocks in getting fuck by a big cock see win I was very young I had sex with 3 guys one day they ask me will I suck there cocks in I sand yes we want insid... Read full Story
45sexyjane 2019-05-27 4,091 Small Tits Crossdresser Amateur Big Tits Masturbation Blowjob blonde Big Cock gangbang Lingerie Sex Toys shemale + shemale sexy crossdresser
66%
Spring Morning
First morning of spring After the long winter it was just starting to get brighter and greener, white anemones were blooming and in a few weeks spring would be at it's most beautiful phase, but for now the gloom of night and mist was just retreating back to the sea and sun was rising giving me ... Read full Story
Femboy Emmi 2020-05-11 3,452 Small Tits Crossdresser solo Lingerie
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 12,931 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
50%
all girls want breasts
All girls want breasts - a lifestyle Sissygurl and her boobs. Let’s start with saying a Sissygurls tits are important to her. Whether you call them breasts or tits it is the same thing. For all women, her breasts are a very important and visible sign of her ‘womanhood’ and regarded as a key a... Read full Story
amberdoll 2020-09-14 2,502 Small Tits Crossdresser Amateur blonde Homemade
100%
A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
KaceyKlarissa 2024-02-24 4,907 anal Small Tits Crossdresser Group Sex Big Tits Outdoor Big Cock gangbang domination sissy femboy Ass to Mouth cum in mouth
80%
Three In A Day
Clara felf especially slutty today. She briefly gazed at her long legs shimmered in the smooth, silky black stockings, and black patent leather pumps as she pressed the gas pedal of her car. Her olive skin and black wig were set off by the brightest shade of red lipstick she could find. Driving d... Read full Story
iluvgurls 2018-11-12 4,486 Small Tits Crossdresser Group Sex Cumshot Blowjob cum in mouth
92%
My Neighbor
When I got divorced and was finally living alone I had many fun times getting fucked all I could by both men and women. I was always dressed when home and loved to stay that way all weekend long and would just put on some pants over my outfit to go shopping sometimes with a coat or shirt over my ope... Read full Story
crossdresser55 2019-10-29 16,386 Stockings Crossdresser
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 12,514 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
Out Shopping with Lisa
Ever since the day she caught me wanking, dressed in her bra and panties, my partner Lisa had made the rules that allowed me to wear female underwear - always when we go out together, sometimes when I go out on my own, and always when I go to the pub with my mates, (in case I fancy my chances with a... Read full Story
shemale lover 2012-08-31 2,932 Stockings Crossdresser Big Tits Big Cock fuck
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,059 first time ass Cumshot suck cd sissy make up
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 4,958 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Property To Be Pimped
It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really d... Read full Story
shemale lover 2013-01-17 7,089 Stockings Crossdresser sucking dildo Interracial
92%
Dani & Paulie - 2
Devon, it turned out, was a complete gentleman. The accent i couldn’t place was a hybred of south London in the UK and the Caribbean. He’d been in the states for a few years after being spotted as a student, modelling for some extra cash. He’d greeted me on the veranda like an old friend, a hug an... Read full Story
SissyDani31 2018-10-09 3,388 Crossdresser Big Cock Interracial
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 11,648 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
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2013-07-18 8,321 anal sex Ebony oral sex Interracial kissing
86%
La primera vez que me hicieron mujer
Desde mis mas lejanos recuerdos, siempre sentí la necesidad de lucir femenina...recuerdo que de niña me encerraba en el cuarto de mi mama y me probaba las medias panty y los tacones, sobre todo unas sandalias doradas que me encantaban...podía pasar horas en esa habitación imaginándome siendo toda un... Read full Story
maritza_tv 2023-04-28 10,319 anal Small Tits Crossdresser Amateur Bareback Creampie Big Cock Guy Fucks Shemale Interracial Mature cd sissy femboy
100%
Seduced At The Gloryhole
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com Enjoy! Golden blonde hair that rested just past her shoulder, piercing blue eyes, full luscious red lips with colorful sleeves of tatoo’d arms. Wow, she was immaculate. She locked ey... Read full Story
therefill05 2020-12-10 9,168 Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale Interracial cum in mouth
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 3,839 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
100%
My TV Sex Adventures Hot time in the Gurl&#
After sucking off the custodian of the offices next door I went back to the club. I was seriously disappointed. I loved how big and hard his dick was and I really wanted a serious cock like his to fuck. I got back into the club with only a knowing grin and a chuckle from the guy at the door. He was... Read full Story
shemale lover 2012-07-05 3,778 Group Sex Cumshot sucking Interracial
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,210 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,382 Big Tits transsexual big ass
66%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2011-11-14 6,650 Big Cock Ebony transsexual
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2012-05-07 4,796 shemale Big Cock oral sex cum licking
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,523 Stockings anal sex Fetish Interracial sissy
50%
A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
shemale lover 2012-06-03 11,027 shemale oral sex Interracial
95%
A Black Tranny Fantasy
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sl**ping with a black shemale was about to come true. She paused... Read full Story
shemale lover 2014-12-03 5,669 tranny Cumshot suck ass fucking Interracial
100%
New Orleans TS dream come true..
In was on New Orleans running water for the victims of Katrina in 2005. I went down to Bourbon St several times an one night I walked into adult fetish store and as I was looking around there was what appeared to be a very beautiful black woman bending over with a very short skirt on. I was admirin... Read full Story
jim3801 2018-09-11 10,509 Group Sex Bareback Shemale Fucks Guy threesome Big Cock Ebony Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
100%
Francis Meets a Black Stud Part 5
I finally came upon a plan that I thought would make everyone happy. I would keep on playing this game with my man. I figured that as long as I was dressed like a girl, it didn't matter who he showed those videos too. I mean no one would know it was me and after all, he would be finish his vacation ... Read full Story
shemale lover 2012-11-20 2,858 cum oral sex Interracial
75%
Amy Finally Lives Out Her Fantasies Part 2
"Wow! What got into you?" "I don't know, I just decided to finally loosen up and go with my desires," she explained. "Did you enjoy it?" "Are you nuts? I LOVED every second of it!" I exclaimed. Figuring the alcohol played a very large role in her sudd... Read full Story
shemale lover 2011-09-15 3,586 Big Tits ass fucking fishnet
66%
A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
shemale lover 2012-03-06 5,381 Crossdresser Shemale and Girl oral sex condom sex
56%
Blow Job
My e-mail is: My rusted, green Toyota Tercel pulls into the mall parking lot. I pick a spot at the back, beyond where even employees park. The next car is a blue pickup 20 spots away. No one parks here, except at Christmas. But I know that I'll soon need the privacy. I'm a freak, a cross-dresser... Read full Story
shemale lover 2013-08-09 6,822 Crossdresser Masturbation Lingerie stripping party
100%
Retail Therapy
It began, as many of these stories do, with a pair of panties. I love lingerie as much as the next girl, but never overly indulge, as money was a little tight. My new husband Alexander and I had finally settled into our post-college lives and were reasonably well off, but had a plan to pay off colle... Read full Story
shemale lover 2012-08-31 3,740 Crossdresser Cumshot Blowjob jerking Lingerie
88%
Who's She?
School had been a bore for Tony. He was a bright lad and didn't have to work too hard to get through classes unnoticed by the teachers and class mates. He had plenty of friends but no one close. He didn't excel in sports or academically. He had picked up a few good exam results but had decided that ... Read full Story
Vinny_A 2019-07-08 11,535 Teen (18+) Crossdresser Amateur Big Tits Bareback Blowjob Lingerie
83%
Dawn's Diary
My name is Donald. I am a single businessman in a small northern California town where I am well known. I am 30 years old and six feet tall. My hair is sandy blonde. I am fairly slight of build and thought of myself as the 90-pound weakling shown in bodybuilding ads when I was younger. However, I am... Read full Story
shemale lover 2012-07-30 3,425 Crossdresser Cumshot dildo orgasm facefucking
100%
Porshe's Escapade Chapter 4
I received an email from Lisa a few days later. She again told me how gorgeous I was and how hard she came when Christie and her fucked me. She then wrote that Christie would be over the following Friday at 5pm to get me ready and then take me to the hotel for the bachelor party. I rushed home fr... Read full Story
shemale lover 2012-09-06 2,791 Crossdresser Big Tits Blowjob
87%
The Neighbour
I made my way up the driveway, after having a few with the guys to end off the week. I was in no hurry to get home because I knew there wasn't anything going on tonight. The wife was out of town for the weekend and the other guys had stuff of their own going on. So I made my way up the rest of the d... Read full Story
shemale lover 2012-12-21 9,714 Teen (18+) Crossdresser sucking Sex Toys handjob
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,363 Crossdresser hardcore ass fucking cd
92%
The trip
I was at work and they decided that some of us had to go to Florida to work on some problems so I was picked. I went home and packed and made sure to pack some of my sissy outfits also because I would be in a hotel for 7 days and have the room to myself it was perfect. The next morning me and the ot... Read full Story
crossdresser55 2019-09-18 12,119 Stockings Crossdresser Shemale Fucks Guy Fetish Sex Toys
50%
Turned into A Feminized Slut by FeminizedBBCslut
Bound and Turned into Feminized Slut by FeminizedBBCslut Chapter 1 - How I ended up meeting John I am an asian TV on hormones for 3 years and as a result have developed a pair of budding breasts that fill out my A cup bra. I have always been fantasizing about being turned from a shy conservative asi... Read full Story
8thick_ 2022-01-03 3,650 Crossdresser
66%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 4,418 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
100%
tiffanylondontv becomes a captive slave prisoner and whored out
I had connected with Master X on a BDSM Fetish contact site. He was the owner of a fetish store and he said that he had been on the BDSM for several years. He had carefully studied my own profile and had seen that I had an immense interest in being used like a slut, being covered head to toe in... Read full Story
__tiffanylondontv__ 2022-09-20 4,311 Crossdresser Amateur Group Sex Fetish Latex Mature
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 4,188 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
100%
I Love To Love You
I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... Read full Story
Brina Giselle 2023-09-24 4,880 anal Crossdresser Blowjob kissing transgender virgin romantic earrings
55%
Dawn's Diary Chapter 3
Back at home it took nearly a week before I was able to sit comfortably after my encounter with Sam and her huge dildo. My thoughts constantly drifted back to her. I continued to keep my body cleanly shaven and regularly wore the outfit that I had worn that evening with Sam around the house. I bough... Read full Story
shemale lover 2012-07-31 2,914 Crossdresser Cumshot oral sex
100%
Porshe's Escapade Chapter 1
Hi, it's Porsche back again and rather disappointed. I thought I would get a much better response to my first story "Interactive Crossdresser...Dare Me" but i didn't. I was kind of reluctant to put myself out there since i have never dressed in public or in front of anyone else but my Aust... Read full Story
shemale lover 2012-09-03 1,946 Cumshot Blowjob Big Cock cum swallowing
100%
My Wonderful Secret Chapter 1
I had just turned 18 and my life was hell. Throughout High School I had been bullied and humiliated. When I got to University, the best years of your life some say, I thought things might improve, but they didn't. What was my problem I here you ask? Well, in a nutshell, I was socially and physically... Read full Story
shemale lover 2012-09-09 4,449 Stockings Crossdresser heels
90%
Brian Becomes Brittney Chapter 1
My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before colle... Read full Story
shemale lover 2012-12-21 5,159 Teen (18+) Crossdresser domination Sex Toys ts
95%
Proud To Be A Sissy Chapter 8
I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how m... Read full Story
shemale lover 2012-12-24 9,137 Teen (18+) Crossdresser Uniform Lingerie domination
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,310 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
87%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 4,882 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
Demoted Chapter 1
Monday I had been working in this office for a couple years, I was a floor supervisor had my own office and a few people under me. It was very easy and never had any trouble at all. I am also a cross dresser and I didn't know it but my story starts with a page I had on the Internet. I checked my ... Read full Story
shemale lover 2012-08-13 5,383 Crossdresser Fetish Lingerie