Sort by
Relevancy

Free Stories

96%
My first BBC experience
I stand 5 foot 8 and weigh 138 lbs. With a perky butt, long natural eye lashes, and clear smooth white skin I would always receive comments from women how jealous they were of my features but never did they want to pursue an intimate relationship with me. But I also didnt have much interest in them ... Read full Story
Jenny Hurle 2020-04-29 14,815 Crossdresser Amateur Bareback Creampie Big Cock Ebony self sucking
100%
First time
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tran... Read full Story
shemale lover 2011-08-14 12,934 first time Creampie ass fucking
100%
My first Escort girl
I was in my early thirties. I had just out of a relationship that ended very brutally. I was hurt for several years as I took it difficult. It was at this time, already having had my first sexual experience with a Crossdresser/Ts when drunk and still thinking of that experience that I decide... Read full Story
likesboth 2024-11-05 2,361 anal Cumshot Blowjob Big Cock Asian Frottage femboy
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 4,237 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 5,799 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 7,762 anal Shemale Fucks Guy Big Cock Frottage
95%
How I became a cute femboy CD part 2
The game of husband and wife Kevin and I played went on for a little over 2 more weeks before we decided to go even further, I say we but it was Kevin who seduced me into it. We got together in our game as much as we could and it was a lot. I would always dress for him in various outfits and my ... Read full Story
Cute_Femboy 2016-04-05 13,084 first time oral sex nipples crossdressing cd sissy
90%
How I became a cute femboy CD part 4
My legs finally started to work again and I turned and was about to walk to my bedroom when Kevin’s voice stopped me. “Come on, Natalie, you know you want to. You have been crushing on David ever since he moved here.” “You’re an asshole, Kevin. You know that. You are a total asshole! I tho... Read full Story
Cute_Femboy 2016-04-05 13,093 first time cumming crossdressing cd sissy cumshot in mouth
100%
Devastating and dominating
Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... Read full Story
shemale lover 2012-01-29 5,601 Masturbation sucking Creampie Latex fucking
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 7,828 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
72%
My First Shemale Sex
Another lovely short shemale story from our forum member, this time from a guy who calls himself "I Fucked A Shemale" I was at my best friends house a couple of years ago. I was maybe 18 i believe. His step mom was there. Well his new step mom that his dad just married like a few days b... Read full Story
shemale lover 2015-03-07 8,240 anal Blowjob cumshots
100%
Abducted and Turned Out Chapter 2
2: Fun time So, after I blew the guy downstairs and told him to come and knock on my door and pay me to blow him again anytime, I went up and took a long hot shower and put on a nighty and went to sleep. I slept surprisingly well considering I had just spent a long night out selling my ass. I tho... Read full Story
shemale lover 2012-08-10 4,968 Crossdresser anal sex sucking Creampie facefucking
72%
From Tomboy To Boy
Mike Flannigan is a wealthy man who, at the age of forty, could certainly afford to retire from his law firm with a lot of money to spend. He had always been the most driven person in his family. He was born in 1951 in Dallas and lived there for most of his life. His parents were a working-class cou... Read full Story
shemale lover 2012-12-03 4,707 anal sex sucking Creampie
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 17,180 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
88%
My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
Nicole_femboyCD 2014-12-03 21,825 anal Crossdresser Cumshot Blowjob rimming cd
100%
The best blowjob I ever gave
Back in 2010 or so I was living in the south(USA). I was a frequenter of Craigslist and other sites to hook up with prostitutes, shemale, Ts, and men. I was doing errands on the weekend and was checking on my phone for craigslist ad's and found one that was a little different. This woman had not pu... Read full Story
likesboth 2024-11-29 1,413 Amateur Cumshot Big Cock Ebony femboy cum in mouth
100%
Westward bound cum slut Chapter 2
Again I'm on the big bird headed out west for another fling. This time is going to be way different though, the players have increased, not to mention both sexes. The tale unwinds in the same fashion as the last trip out this way, the plane flight was long and boring, and being very nervous didn'... Read full Story
shemale lover 2012-12-16 3,993 anal Group Sex sucking Creampie cum domination
96%
My First Time as a Girl
I was hoping to hook up with a straight guy. I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a b... Read full Story
shemale lover 2013-12-07 7,062 tranny Crossdresser Creampie ass fucking cd
37%
First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
shemale lover 2013-07-17 6,628 first time Crossdresser Fetish Mature bisexual
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
Lisawantsu7 2014-09-02 7,112 hardcore Creampie Big Cock ass fucking Shemale and Girl
80%
Bitch Maker Chapter 2
I woke up feeling pretty good. A new place and an unexpected blowjob had fallen into my lap last night. As such I regarded the maid outfit laid out on my dresser in good humor. Sam was a very silly woman after all. Yawning and stretching I stepped into the hall, hearing movement in the kitchen. I... Read full Story
shemale lover 2012-06-24 5,015 hardcore anal sex Cumshot sucking Creampie
100%
The First Cock I Ever Sucked...
...was my own. I was in my late teens and still trying to figure out my own sexuality. I loved women. Their soft curves, their smell. But I also felt a lacking; something was missing. I was alone in my room one day, listening to music and fantasizing about sex. My dick grew hard as I imagined ... Read full Story
Stark Naked 2022-04-20 6,603 Blowjob Big Cock self sucking cum in mouth
100%
First Time With Shemale
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
shemale lover 2011-08-26 4,335 anal Creampie shemale
94%
My Shemale Fantasy
Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... Read full Story
Jakester 2013-04-10 32,675 first time Creampie Shemale Fucks Guy ass licking virgin
100%
First Tranny Experience_Part 2
I had said good bye to her at her door and drove home. I got home at a decent hour and went to bed. The following day at soccer practice, I could only think about how wild a time we had together and began fantasizing about the whole affair when my cell phone went off. To my surprise, it was Kim s... Read full Story
Jon Paul 2018-08-06 5,220 Group Sex Bareback Creampie Blowjob Asian Ladyboy
93%
First Time I tasted Tgirl Sperm
I met a Mexican Trans girl online from Hermosillo and we hit it off and corresponded for a a few months. The vibe was good and ended up deciding that I would help her pay the $140 bucks for her 6-month tourist visa to come up and visit..the process took forever but once she got it, I booked her a pl... Read full Story
AllenB 2022-08-09 9,571 Crossdresser Amateur Cumshot Latina Bareback Creampie Shemale Fucks Guy Fetish Blowjob Interracial Homemade cum in mouth
91%
First Meeting with Couple
Hi everyone, I actually went through with it and got together with the couple from the fetish party to experience my first sex and scene in real life. It didn't go as i had dreamed of; but, thinking that it would go like that was pretty naive on my part. To start with, i Must tell how cute I l... Read full Story
shemale lover 2014-08-13 5,721 first time shemales bdsm
75%
Stoping by the Adult Video Store.
Has anyone been ever stopped at an adult video store. That a rhetorical question, I know the answer. The first time I visited an adult video store, I was in for the shock of me life. Just like any inquisitive twenty yr old, I thought the establishment sold adults videos. It never dawned on my about ... Read full Story
lkusex 2021-05-28 5,346 Blowjob self sucking Ass to Mouth
100%
My first TG lover
I first met Holli at the gymnasium of our apartment complex. Since it was around 6:00 am on a Sunday morning, I didn’t expect to see anyone that early. At first just like we all do, the customary good morning, small talk, and it usually stops there, but there was just something that drew my attentio... Read full Story
Jon Paul 2022-07-01 8,375 Amateur Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,714 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
82%
Nobody Forgets Their First Time With Shemale
Her name was Veronica. She was about 6" tall and her heels were so high it made me dizzy. Actually, together with the fishnet stockings she was wearing, it made me dizzy and horny. It was my first time with she-male and my first time with that kind of service. Veronica knew that was my first... Read full Story
shemale lover 2016-06-02 9,926 first time shemale jerking off
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,963 Big Tits Cumshot Masturbation Uniform Frottage
100%
HE DIDN'T KNOW I WAS TRANS...
I'd worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
mika96 2023-05-11 7,273 anal Amateur Bareback Creampie Blowjob femboy Ass to Mouth
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 11,129 Masturbation Blowjob blonde ass fucking big boobs
100%
Lola Chapter 4
We sat at the table. I had made the effort to cook a small three-course French-inspired dinner. I was in love, but Lola’s mind seemed elsewhere. - How nice… She was chewing absent-mindedly. - I have to ask you something. - Shoot baby. Ask away! Lola looked deep into my eyes: - Could you ima... Read full Story
BellaBeau 2023-10-30 6,198 anal Cumshot Latina Bareback Creampie Shemale Fucks Guy Frottage Homemade Lola
100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 5,556 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
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 4,936 sucking Blowjob cum bisexual cd sissy femboy bi trap
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 6,217 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
100%
Becoming a Chrissy - Chapter 1
I always knew I was a little sissy slut. When I was ten, I took a pair of my mommy’s panties to try on. It was a hot pink G-string that my petite mother must have worn when she was ready to get fucked by my daddy. It was just the right size to cover my prepubescent clitty and also stretch through my... Read full Story
mindlessrobot45 2024-05-13 4,870 Crossdresser Blowjob blonde femboy cum in mouth
100%
My story, more or less pt.2
So there I was, a boy with a desire. (Refer to pt.1 for context) A few months went by from the "initiation" and I've progressed quite a bit I have switched from shemale porn to femboy porn, to relate to the main characters more. I have also scoured every closet in desperate search f... Read full Story
Thigh_High_Boi 2022-12-23 5,772 Stockings Blowjob Ladyboy Lingerie Homemade self sucking cum in mouth
100%
How a Transexual escort showed me how to bottom!!
I was now in my early 40's. I have had many experiences thus far with women, men, transexuals, and crossdressers. The majority of these encounters that involved cocks were mostly oral. I did however have a few experiences being topped. The first was unbearable yet I could not withstand the pain(... Read full Story
likesboth 2024-12-24 2,585 Amateur Cumshot Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ebony Sex Toys femboy
100%
Black Transsexual Power Games
I give dick and my Black male bitches have to take it. No such thing as trying. You either take my dick up your ass or you don't. I smiled to myself as I thrust my ten inches of hard Black dick into the tight asshole of Richard Lucien. The big and tall young Haitian groaned as I fucked him. Well, th... Read full Story
shemale lover 2012-07-10 3,584 anal tranny Creampie Ebony oral
87%
Southern Hospitality Ch. 03
XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... Read full Story
Gwapo67 2022-05-16 5,289 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
The Terrace View Apartments Part 7
My new life had settled into a wonderful routine. I would wake very early in the morning, usually still wrapped securely in Mistress Kendra’s arms. I would spend an hour or so working on my figure maintenance exercises, enjoy a cleansing enema, a refreshing bath and body shave, then I would la... Read full Story
shemale lover 2011-11-19 4,384 Creampie Blowjob domination
96%
Making A Man Out Of Tommy
I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... Read full Story
pennypenny 2018-08-31 10,394 Teen (18+) Crossdresser Amateur Masturbation Bareback Creampie Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
91%
Lake Surprise
After finals of my first year in college in a northern university, I was ready for some real relaxation back home in the warm south. During finals I had started thinking how nice it would be to borrow my brothers boat and hit the lake for a week. I talked my roommate into making the trip home ... Read full Story
shemale lover 2011-12-08 11,145 anal Group Sex Creampie
100%
Downsizing Chapter 3
Work was going quite well. The company started to grow again, and some new personnel had been hired. Even unknown to me, there had been a couple of males hired in the last few months. Ms. Stanton had informed them when she got to the dress code that the makeup was a requirement, and that the one mal... Read full Story
shemale lover 2012-11-10 3,421 anal sex Cumshot Creampie oral 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 12,586 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%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 7,174 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 8,850 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
The Girl Next Door Ch. 02
derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... Read full Story
Gwapo67 2022-05-13 5,790 Bareback Creampie Guy Fucks Shemale cum in mouth
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 5,557 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 7,212 Creampie Big Cock ass fucking
100%
Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
shemale lover 2012-05-26 4,835 anal sex Creampie Blowjob crossdressing
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 11,783 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
91%
The Girl Next Door Ch. 03
derezzed Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Ale... Read full Story
Gwapo67 2022-05-13 6,598 Bareback Creampie Shemale Fucks Guy threesome Blowjob cum in mouth