Sort by
Relevancy

Free Stories

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 3,388 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 4,735 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
Lettera a Cristina (bocca di rosa)
Beh, e' bene che tu lo sappia. Ero io quel 40enne che hai incontrato in metro'. Avevo, per la precisione, 39 anni e 10 mesi. E, ti sbagli, non stavo scrivendo proprio a nessuno, cercavo solo l'applicazione della telecamera per riprenderti con un filmino o scattarti delle foto per averti anche dopo... Read full Story
Sexbit 2023-08-22 572 tranny Cumshot Outdoor Blowjob Ladyboy femboy Vintage cum in mouth teen (18+)
55%
story of Jojo
Some find it confusing of who i am or what i am, including me. i found some kind of definition: femboy A young boy who presents extensive feminine mannerisms and actions often blurring the line between a boy and a girl. Can be confused with a cross dresser, but it usually refers to boys at v... Read full Story
jojo58654 2017-09-12 10,382 Amateur transvestite strapon cd femboy
57%
MY CONFESSION
MY CONFESSION Story of Emilio Anaya, lover of girls with penis. I have that to do a confession. I hope you keep the secret, please be my confessional today. I love T-Girls, Shemales, Tranny, Ladyboy, Femboy, Transvestite, Transsexual, girls with penis. Just by saying it, I have taken a weight ... Read full Story
emilio1213 2020-05-11 3,096 Amateur Masturbation Solo Shemale
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 3,899 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
50%
Need A New Keyholder/Daddy
I get an erotic thrill off of the thought of another man "owning" my body and having control over my sexual pleasure. I enjoy having my boyclitty, my cock, locked up in a chastity cage; it represses my erections, hides my cock so I rarely see it, and denies me any of that little sexual pleasure of t... Read full Story
Chrissy Tunnell 2022-02-14 2,092 Crossdresser solo Amateur Fetish Ladyboy Lingerie domination Guy Fucks Shemale Frottage
85%
Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
shemale lover 2014-09-17 60,665 suck Bareback Asian Ladyboy ass fucking
100%
la storia di Sara
Erano alcune settimane che ciattavo con Sara, una trans bolognese conosciuta per caso in internet. Di Sara ho visto solo il bel viso molto femminile con lunghi capelli biondi ed il suo meraviglioso seno. Una sera stavamo parlando e lei mi disse " alcuni mesi fa mi sono rifatta il seno, ho conosciut... Read full Story
Sissy Mari 2022-03-22 2,163 Crossdresser Amateur Cumshot cum Ladyboy Lingerie Sex Toys Homemade shemale + shemale sissy crossdresser siisy slut
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,386 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
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 2,582 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
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 10,220 anal Small Tits Crossdresser Amateur Bareback Creampie Big Cock Guy Fucks Shemale Interracial Mature cd sissy femboy
50%
Regrets. . . - by Katrina Electrika
When Mariana Cordoba was in her full blossom of being known in The Entertainment Industry, I was in China and Thailand having Lotus Mooncakes on Chinese and Thai New Years. . . The Orient is my Home now in life and I will be going back there very soon. . . but I have to say this, even ask Myself ... Read full Story
Katrina_Electrika 2018-11-20 2,469 Ladyboy transexual transexuals
100%
CONOCIENDO A ENRIQUE EL FOTÓGRAFO CHILENO (parte 1)
Era verano, y acababa de terminar el colegio y salí a dar una vuelta por la plaza, era una mañana calurosa, me senté bajo la campiña un buen tiempo haciendo hora, y entonces oigo una voz poco común que se dirige hacia mí, era un caballero de nacionalidad chilena, lo note por la voz, de 30 años aprox... Read full Story
katiMelendez 2020-12-14 1,837 Teen (18+) Amateur Latina Bareback Fetish Ladyboy domination Homemade
67%
Asian Crossdresser - How My Crossdressing Journey Began
My name is Patrick (Pat) Young and I was in Hong Kong. It all started when I was 5 years old. I was an innocent and naive boy, who had no idea the difference between boys and girls. I thought the differences were that girls had long hair and they wore skirts. When girls grew up, women were sh... Read full Story
pat1young 2015-12-08 11,714 solo masturbating crossdressing high heels Asian TS
100%
Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
Jon Paul 2022-01-03 2,707 Stockings Cumshot Bareback Blowjob Asian Ladyboy Guy Fucks Shemale
50%
Pa-mie sex-agénaire
Luxure frénétique d’une pa-mie sex-agénaire; entre rêve et réalité Je n’avais jamais fantasmé de mec viril, même après avoir offert ma virginité; mais à une fabuleuse sissy. Avant mon Ѐre, mes préférences de fantasmes étaient toujours avec des lui-femme glabres, idem concernant mes relations d’aprè... Read full Story
hippocampus_171 2023-07-09 654 anal Amateur Group Sex Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy Ass to Mouth
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,406 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
K*dnapped & R*ped
"You're nothing but a tease, a flirt, you just like to play around and lead guys on," someone messaged me on the swinger site I'm on called AdultFriendFinder. "No," I replied, "I have actually hooked up with guys I met here, I am just very busy." And that is the truth. I work a full-time job and ... Read full Story
Chrissy Tunnell 2022-02-02 3,294 Crossdresser Amateur Outdoor Bareback Fetish Ladyboy domination Guy Fucks Shemale Homemade
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,529 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,420 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 5,056 Stockings Blowjob Ladyboy Lingerie Homemade self sucking cum in mouth
100%
My story, more or less pt.3
Earlier on, when I was scouring through various drawers and closets for feminine clothes in my home I have stumbled upon two old skipping ropes. "A fun time" I thought to myself, not giving them another look and continuing with my search. Little did I know they would become the backbone of my "sessi... Read full Story
Thigh_High_Boi 2023-01-06 3,436 Stockings Masturbation Fetish Ladyboy Lingerie Homemade pov
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 8,835 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
62%
MY EXPERIENCE WITH SHEMALES (A my eleven years)
MY EXPERIENCE WITH SHEMALES A my eleven years There was a fair in my town. There were many funs to play. I was dazzled, because my mother left me to explore only that magical place and I found magic in it. I approached a table where there was a set of cards. The rule of the game was to bet mo... Read full Story
emilio1213 2020-05-11 3,836 Amateur Big Tits Ladyboy Solo Shemale
80%
My First time squirting
I have, for many years now, been fascinated with the beauty of Ladyboys, TG, TS, TV's especially Asian girls (but do love to watch a lots of non Asian girls too) and have watched lots of porn (and still do to this day) about these beautiful girls and seeing them make themselves cum is such a turn on... Read full Story
Robmb6996 2023-07-26 6,369 Crossdresser solo Sex Toys
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-06 1,120 Teen (18+) Crossdresser Amateur Fetish Lingerie
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,250 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
50%
SOUS LA DIRECTION DE MAMAN ⚧️ ⚧️
Jaime n'avait jamais eu beaucoup de chance avec les filles au lycée. C'était venu et reparti, et maintenant il profitait d'un dernier été avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un salaud ou un douchebag, c... Read full Story
Femboy 2021 2023-03-18 894 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
50%
LE PROGRAMME D'ÉCHANGE SISSY ⚧️ ⚧️
Kristy a travaillé pour Le Matriarcat. Cela semblait plus officiel que ça ne l'était vraiment. Comme si c'était un "Nouvel Ordre Mondial". C'était en fait un club dirigé par des femmes spécialisées dans certains services que les hommes paient grassement. Cela pourrait être appelé prostitution selon ... Read full Story
Femboy 2021 2023-03-25 977 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,018 anal hardcore erotic encounters fantastic
50%
The Greatest Lie Part 17
They say that life is about making choices. But we humans don't get to choose the two most important factors in our lives. We don't get to choose our genes, so I got stuck with XY chromosomes. And we don't get to choose our natal families, so I got stuck with my mother and father. My father, Edua... Read full Story
shemale lover 2012-01-20 4,361 erotic encounters fantastic consensual
87%
Why you should never cam
* Sorry for the poor writing but since it is the summer and I am taking sometime off to reflect before starting school next year I thought I would write up about what had happened to me the summer before. It is currently a work in progress and if spot any spelling mistakes or errors feel free to cor... Read full Story
jennychen 2014-09-02 5,029 cock shemale Big Cock Asian
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 4,814 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
50%
Lust and Love with Leona
This is a work of fiction. * The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn't pull in a bar. But I found that I could not s... Read full Story
shemale lover 2011-10-07 4,373 hardcore celebrities oral extreme
0%
The Greatest Lie Part 13
Does Life Imitate Art? I love technology, in spite of the stereotype about girls. Although I was a guy, at least outwardly, until a year ago, I think I was always inwardly a girl. According to the stereotype, we girls are supposed to be indifferent to anything more technical than the designer cov... Read full Story
shemale lover 2012-01-20 4,618 femdom erotic encounters consensual
100%
A Flash of Lace
The insistent ringing of the phone broke my concentration and with great annoyance, I climbed off the bed and picked up the receiver. "Hey little brother!" My sister's sparkling voice filled my ear. "Di, Is that you?" I exclaimed happily "Got any more sisters I don'... Read full Story
shemale lover 2012-03-03 5,936 Stockings Fetish dressing
85%
True story, TS 3-way
This is a true story. It was a typical night in Pattaya Thailand and I'm still recovering from the 25 hour flight from Tennessee to Bangkok that I flew just days before. After a few days in BKK, I arrange for a hotel car to me to Pattaya, a seedy explosion of lights, blaring music and drunken ... Read full Story
Thailover 2014-03-11 9,544 Cumshot threesome jerking ass fucking facial stroking
50%
I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
Oldslut Sissy 2024-04-15 7,576 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
50%
LE GRAND PASSE-TEMPS DE MAMAN ⚧️ ⚧️
Je me souviens d'une époque plus simple, avant d'être ce que je suis maintenant. Malheureusement, je ne saurai jamais ce qui aurait pu être. Je ne pourrai jamais revenir en arrière. Je ne pourrai jamais revenir à ce qui était autrefois. C'était il y a seulement 2 ans. Je suis Harvey. J'étais à l'... Read full Story
Femboy 2021 2023-04-10 800 Big Cock gangbang Interracial Sex Toys sissy sissification forcé anal mére mere et fils
100%
Alone at home
Living with my religious parents didn't provide many opportunities to spend time alone to enjoy myself. Only openings I found where, when showering, and occasionally when my parents travel, though that was not very often. I shared my room with my lil siblings, and since they were young and curious, ... Read full Story
Sara M. 2024-01-16 5,934 solo Lingerie small cock Homemade sissy femboy
100%
Andy In Pantyhose
He had the house to himself for a few hours. Andy slid his older sister Kelly's taupe nylon pantyhose slowly up his nice, smooth legs, wriggled them up around his narrow boyish waist the band snapping in place. His penis was so stiff against the wispy fabric! He sighed happily. Sitting down on ... Read full Story
ALEXEAMES 2024-01-18 4,943 Stockings Crossdresser solo Amateur Masturbation Fetish Lingerie pantyhose Homemade sissy femboy teen (18+)
100%
My cross dressing journey
I am a man who likes to cross dress, currently single and living alone in Beijing. I like to dress up as a woman and go out, passing through every street, entering nearby shopping malls and supermarkets, as well as the women's restroom inside, and live streaming on a live streaming platform. I also ... Read full Story
boysgirls 2024-02-15 4,213 Stockings solo Amateur Masturbation Asian Lingerie pantyhose Homemade chinese
50%
sine qua non: anal/vaginal pleasure
One thing's for sure, my desire is to be fucked and to fuck... And it's in this order of things that I've been wanting to fulfil my fantasies for the last two years. I'm not too fussy about choosing my partners, but luck has always smiled on me when it comes to finding the right one. However, over t... Read full Story
hippocampus_171 2024-04-05 2,233 anal solo Amateur Mature big ass sissy femboy
50%
jouir anale/vaginale mon ‘sine quoi non’
Quelque chose est sûre, mon désir est d’être baisée et baiser… Et dans c’est dans cet ordre des choses que je veux réaliser mes fantasmes depuis deux ans. Bien que je ne sois pas trop pointilleux pour choisir mes partenaires, la chance m’a toujours souri pour trouver le bon. Toutefois depuis quelqu... Read full Story
hippocampus_171 2024-04-05 161 anal solo Amateur Mature small cock big ass sissy femboy Vintage
100%
Inmediatamente despues
Luego de que el termino en mi nalga, todavía con la sensación de placer que teníamos los dos, me beso tiernamente y me pregunto donde quedaba el baño. Yo todavía de rodillas en el sofá, pase mi mano izquierda sobre mi nalga y sentí el semen que mi macho había depositado sobre mi y lo trate de recoge... Read full Story
maritza_tv 2023-04-28 1,128 anal Crossdresser Amateur Creampie Big Cock Ladyboy Lingerie Guy Fucks Shemale Interracial Mature Homemade sissy femboy
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 3,919 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
44%
Gargantua
Women do not have penises or testicles. These sex organs are specific to men. As the boy in Kindergarten Cop demonstrates, even young children are aware of this most fundamental fact of life. However, in the genre of erotic fantasy art known as futanari, hermaphroditic "dickgirls" defy nat... Read full Story
shemale lover 2011-09-12 7,468 Futanari dickgirl big cocks
38%
Am I gay?
Please help me. I'm confused and unsure if I am gay. I feel so ashamed of myself. I don't want to be gay but I was molested by my neighbors at 6 years old and from then on I would wear my mom's panties or sniff my sisters while masturbating. Cumming would always make me feel guilty for what I have d... Read full Story
Chinaysissyslut 2020-02-24 6,010 Stockings Teen (18+) Small Tits Crossdresser solo Amateur Masturbation Asian Ladyboy Lingerie Homemade webcams
88%
A hole new world unfolding before my eyes.
When i was still a little boy, i was always surrounded by women, i was raised mostly by them, so i always was in touch with that feminine side of mine. In addition my sexual desires and cravings developed actually kinda fast. I remember loving the feeling of watching my mom's wardrobe specially her ... Read full Story
stranger696 2020-11-06 4,132 Crossdresser solo Cumshot Fetish Ladyboy Lingerie Frist time Closeted
50%
Why Do Guys do this?
Why do guys on the porn, dating sites and social media sites I'm on want to chat live on video all the time? And if I don't agree they unfriend and even block me. Why? Aren't my videos and pixies good enough? They are of me...they ae real, and not photoshopped (except for sharpness and clarity.) I h... Read full Story
Chrissy Tunnell 2022-03-14 2,447 Crossdresser solo Amateur Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Frottage Homemade pov Compilation
100%
My Fantasie: I am a sissy slutty stripper
My favorite fantasie: I am myself but with a feminine body, but with my cock and with real breasts and a pussie, dressed in heels with lacy anklets, white hose and garter belt, white high-cut lacy panties, white lacy bra with nipples exposed, pageboy short blonde haircut, rhinestone necklace/br... Read full Story
kelliecdgirl 2024-05-22 655 Stockings Crossdresser solo Cumshot Ladyboy Lingerie sissy