Sort by
Relevancy

Free Stories

100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 4,963 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
100%
Highway in Heels
Highway in Heels By Sabrina G. Langton *Stories from the real world 1 This story is autobiographical. When I was 20 years old I used to drive a van for my parents from Brooklyn to Tarrytown New York once a week to drop off merchandise for retail shops in the area. I always had a full van on ... Read full Story
Brina Giselle 2023-08-28 4,621 Crossdresser blonde pantyhose kissing transgender
100%
Police House Call
My heart was beating a mile a minute when I heard the knock on my door. I was hoping that it might be Beau, or Larry, or if I’m lucky it would be Tom Cobb. He asked me to call him Tommy. I had been thinking about him recently. Bo and I had banged the night before, but I was as horny as ever. Larry w... Read full Story
Regina10 2024-04-19 3,436 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
92%
MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... Read full Story
pennypenny 2019-01-08 7,216 Stockings Crossdresser Group Sex Cumshot Masturbation Bareback Creampie Fetish threesome Blowjob Big Cock gangbang Lingerie redhead domination Guy Fucks Shemale Sex Toys Ass to Mouth cum in mouth double anal
100%
Business trip
Craig and I were salesmen for the same company and on a trip together to woo new clients. The last thing I expected was that we would woo each other. It had been a long day and we went to our rooms to relax and unwind. After I had my room service and wanted to go over the proposals I realized Crai... Read full Story
Zöe from Kingston 2019-10-07 7,223 Crossdresser anal sex Cumshot Blowjob Lingerie cum in mouth
85%
How Ginger was born
So, how did I get into all this stuff in the first place? I had been into crossdressing from an early age and realised I was attracted to other boys from when I first went to an all boys school. I didn't have my first experience while crossdressed until later in my teens. It was certainly un... Read full Story
Ginger__57 2018-03-26 6,226 Stockings Crossdresser cum in mouth
100%
Fooled Into Love by a Beautiful Transexual
A fictional, steamy love story about a Man’s first experience with a Shemale... a real take charge kinda girl! Maria Lopez was an absolutely stunning 23 yr old Puerto Rican Goddess. I remember the first time I laid eyes on her, bent over inside her hatchback Toyota, pulling out a hanging fern pla... Read full Story
Oobatz 2018-07-24 12,580 Small Tits Amateur Cumshot Bareback Shemale Fucks Guy Big Cock domination cum in mouth
91%
My Seductive Secret (True Story)
During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... Read full Story
Chickzdigmeyup 2019-06-18 13,981 Stockings Teen (18+) Small Tits Crossdresser Cumshot Outdoor Masturbation Bareback Fetish Blowjob Big Cock Lingerie domination Sex Toys Homemade cum in mouth
86%
Alex’s Bottom Slut
So when I was younger, I worked at a pizza place as a delivery guy. It was a pretty boring job for the most part but that all changed one night. I got a delivery to just outside of our range but decided to take it anyways because we were slow. When I got there a very tall and muscular black woman in... Read full Story
Jsmithsub 2019-11-18 56,453 Group Sex Cumshot Shemale Fucks Guy Blowjob Big Cock Ebony gangbang domination Interracial Ass to Mouth cum in mouth
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 9,945 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
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 4,294 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-01 1,032 Crossdresser Cumshot Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 7,576 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
80%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 5,984 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 4,634 anal Crossdresser Bareback Blowjob blonde Big Cock Lingerie Guy Fucks Shemale Mature Ass to Mouth cum in mouth
100%
Regina's scary, and sexy Blind Date
I had just finished doing my makeup, finally deciding which blush to use, and I thought I had some time for my meditation. However, Mr. Cobb was early. The gold minidress I wore showed enough legs, ass and tits to make any man horny, and the strappy tanned five-inch sandals, made me feel majestic ... Read full Story
Regina10 2024-03-18 4,504 anal Crossdresser Bareback Creampie Fetish Blowjob Ebony Guy Fucks Shemale big ass sissy Ass to Mouth cum in mouth
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,799 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 3,769 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl 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 7,722 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
Late Night Snack (Touch me in the morning)
I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... Read full Story
Regina10 2024-03-28 3,866 anal Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ebony Ladyboy Lingerie
100%
A girl like no other,
A girl like no other, It is with a certain excitement that I choose from my wardrobe the underwear that I will wear to welcome you. I'm falling for my vintage lingerie from the 50s: These very feminine sheaths, slit at the crotch to better accommodate your desires. These corsets and bustiers... Read full Story
sandratvtg 2024-07-04 478 anal Stockings Lingerie Sex Toys travesti Vintage
91%
From gamer to b*tch
Chapter 1 So me and my buddy have been gamer friends since high school. When we graduated we started going to different schools and working so we didn't have time to game like we used to, but we made time to get together have some drinks and game once or twice a week. When we we would game we wou... Read full Story
Mightyb1g 2020-02-21 15,992 Crossdresser Amateur Blowjob cum in mouth
100%
Wife got suspicious...
Wife got suspicious... I ended up having a relationship with a married man I'll call Tom. I didn't know he was married until he told me we had to stop kind of like dating because his wife was getting suspicious. We met online, he was a guy who liked crossdressers like me. He was pretty cute... Read full Story
Kellygirl81 2024-06-18 1,062 Stockings Crossdresser Cumshot Lingerie Frottage cum in mounth
81%
That night....
I was extremely nervous when I pulled out my phone and dialed the number. Never before, in my wildest dreams, had I thought I would act on one of my strongest fantasies. I knew I would be nervous when I first met her, but after exchanging pictures and seeing that big, fat cock of hers, I knew I ha... Read full Story
bigTHICKY 2017-05-08 9,244 Big Tits Cumshot Latina Big Cock Ladyboy cum in mouth
80%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 5,927 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth cum in mouth
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,686 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
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 3,875 Crossdresser Amateur Cumshot Masturbation Bareback Blowjob Lingerie cum in mouth
93%
Nancy finds out...
Nancy’s stay with us that summer was going to prove even more eventful than ever I could have imagined. Even after having been caught wearing her things by the neighbour’s son, Lesley, which led to a whole new dimension in our friendship, as you’ll know if you’ve read “Caught in the Act…” Once ag... Read full Story
caroletv31 2018-04-23 8,564 Stockings Fetish Ladyboy Lingerie Shemale and Girl high heels cum in mouth
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,554 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 3,548 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
The Twink and the Bear
He stood there, slowly rubbing his hardened cock in the confines of the public toilet cubicle, trousers around his ankles, his legs adorned in black nylon stockings, held in place by the straps of his delicately laced suspender belt. It was so naughty to be playing with himself in a public place, wi... Read full Story
Daddybear71 2023-03-28 4,418 Crossdresser Blowjob Big Cock Mature cum in mouth
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 3,832 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
95%
My best friend turned trans.....so I fucked him - Part 1
Theres a bit of history to this one so strap in! I started hanging out with this group of kids in my area when I was 12 years old, we did all the typical stuff you can imagine young kids getting up to (played football, chased girls etc...) over the years I became really good friends with one of the ... Read full Story
iconicirish 2023-05-11 8,789 Stockings Amateur cock Masturbation sucking Blowjob Big Cock Lingerie Latex transgender sissy
66%
A Ski Bunny is Born
AQToday I am a fully-fledged she-male, living with my girl friend Kim, who, to me, is the most beautiful girl in the world. We live as sisters to the outside world, but we are in fact passionate lovers. This whole true story started some 5 years ago, let us tell it to you. At that time I was a si... Read full Story
shemale lover 2012-06-21 11,344 anal sex Cumshot Lingerie oral sex Sex Toys
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 4,285 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
The Biology of Music - I fucked my trans substitute teacher
I was never strong in school. I wasn't very interested in what we were being taught, and the teachers liked me enough to not give me too hard a time about it. I attended an all boys school. It was actually quite a religious school which makes this story all the more surprising. I was in the middle c... Read full Story
terrifictim 2022-01-03 3,808 Creampie Guy Fucks Shemale feet licking first time with a tranny teacher student
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 4,768 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
Single sissy in 2024
I’m married, but in law only. Wife and I never fuck; she is a massive prude (naturally only since the ring went on haha). So I dream. Dream about if i lived alone in this day and age. Having fuck machines/massive H cup roanyers/alllll the sexy lingerie delivered directly to my door! I’d... Read full Story
howdyhiddy 2024-06-07 2,155 Crossdresser Lingerie sissy sissy slut fuck machine prostate cum breastplate roanyer
100%
I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
shemale lover 2013-03-20 7,967 Crossdresser Lingerie pantyhose cd softcore
96%
How I began my crossdresser transformation
Here are the usual disclaimers this story is for adults only if you are viewing this and are not 18 years of age or older please close this page immediately. There is no crossdressing in the story but this is how I began my transformation from regular boy into cock sucking teenage crossdresser.... Read full Story
srlvictoria 2013-04-10 11,963 anal Crossdresser oral handjob sissy
100%
Lady In The House Ch. 05
A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... Read full Story
✘Transensual✘ 2019-02-25 4,462 Crossdresser domination PRISON prison sex
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,794 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
Emily and Steve Part 2
I was sitting at my desk with my office phone pressed against my ear, supporting myself with my left hand and trying not to fall asleep. On the other end, someone from Gooseman Paper Products droned on about terms of payment and invoice formats. It was a typical Thursday afternoon. Just then, an ... Read full Story
shemale lover 2012-04-06 2,966 Crossdresser anal sex Cumshot blonde rimjob
92%
My Brother's Panties
My brother and I are twins, fraternal not identical. Throughout our lives, no one ever confused us, and furthermore, no one ever thought we were siblings. Growing up I would often get the question, "Kevin, why do you hang out with Jamie so much?" People were always surprised when they lear... Read full Story
shemale lover 2013-01-12 13,683 solo sucking jerking Sex Toys swallowing
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,406 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,185 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
Eve Quest Part 3
Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I'm reasonably sure I was given the Toilet command and I hope I did a good job. In any event, I was still on the bathroom floor when I heard my mistresses ... Read full Story
shemale lover 2012-04-21 4,366 transformation oral sex cum swallowing
100%
Sabbatical or Continuous Gang Bang?
My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My... Read full Story
shemale lover 2012-08-28 5,513 Crossdresser Cumshot Fetish Blowjob gangbang
82%
Pandora's Box Chapter 1
I discovered transsexual women completely by accident when I was 18. I was watching one of those Real Sex shows on HBO, and without warning, two women who were showering together for a video shoot turned around and I was shocked when I saw cocks where I expected to see pussies. What probably shocked... Read full Story
shemale lover 2012-08-31 4,176 Cumshot Blowjob transsexual Lingerie condom sex
100%
Proud To Be A Sissy Chapter 1
I had just turned eighteen and only had two months of high school left. My marks were good and already had a possible placement in a university where I hoped to get a new start. I was so looking forward to getting away from all the shit that life had forced on me in this little hick town. Usuall... Read full Story
shemale lover 2012-12-23 11,851 Stockings Crossdresser Big Cock ass fucking ass licking
92%
First time being dressed as a woman
I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman. Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a... Read full Story
shemale lover 2013-04-15 6,910 Crossdresser suck facial ass licking cd
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 4,840 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
What The Wife Doesn't Know...
After 5 years of marriage I was getting bored. Don't get me wrong, my wife was great in the sack, always ready to go, and keen to experiment, but I needed something she couldn't give me: cock. After thinking about it long and hard (no pun intended), I decided that not just any cock would do. I d... Read full Story
shemale lover 2011-12-25 11,422 cum ass fucking
66%
Finding A New Purpose Chapter 5
I woke up in my own bed, rubbing the sleep out of my eyes before making my way to my bathroom to get ready for the day like I normally did. Quick shower, shave my legs and face, brush my teeth, get dressed (if you could call it that), and started walking down the hall towards the master bedroom, yaw... Read full Story
shemale lover 2012-08-07 3,431 sucking cum swallowing public
100%
Tranny Night Out
Tranny Night Out and One Kinky Session Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends. I knew something was wrong but neve... Read full Story
shemale lover 2013-05-01 7,701 Stockings suck Lingerie ass fucking stroking
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 8,809 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!