Sort by
Relevancy

Free Stories

85%
Busted
The guy turned back and walked up behind me and whispered, "I like your panties." I was so busted. I turned to him and said, "Excuse me?" "It looks like those panties you're wearing are pretty sexy. Maybe you'd like to show me them." My face burned with embarra... Read full Story
shemale lover 2012-10-12 2,951 Cumshot jerking cum swallowing
100%
My first time
My mother always said she wanted a daughter….my guy name was Adrian, so you could see where she was going with that. I was also a real sissy as a kid, terrible at sports, threw like a girl, did very few real boy things. My best friend and I discovered porn and masturbation together. My mom... Read full Story
shemale lover 2012-10-22 6,684 first time cum oral sex cum swallowing feminization
100%
American Futa
For those who don't know what a futa is, it is usually depicted as a hermaphrodite but for the sake of this story it'll simply be transsexual. The other distinguishing factor is futa's are usually nothing more than mindless sex toys to their masters. Some would say its a step down from being a slave... Read full Story
shemale lover 2012-10-26 7,074 tranny Cumshot oral
100%
An Invitation
"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of ... Read full Story
shemale lover 2012-11-16 4,994 Fetish oral sissy
96%
Shelley's Not a She
Her name was Shelley, she was a waitress at the local steakhouse Buck's, and she was the reason that Matt came back to the place every Friday night for dinner. Sure, the sirloin was pretty good and the chef made it a point to offer some interesting sides, but it was watching the swish of Shelley's s... Read full Story
shemale lover 2013-01-16 10,128 Cumshot sucking jerking big boobs swallowing
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 6,565 first time Crossdresser Fetish Mature bisexual
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 8,105 Crossdresser hardcore ass fucking cd
85%
Francine Hung Shemale
This is the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in California and Mexico as ... Read full Story
darrell 2015-11-16 10,041 sucking Big Cock ass fucking deep throat butt plug
89%
Fem Firm 2 -The Weathergirl
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 2016-11-14 18,537 big dick anal sex suck Blowjob cock sucking workplace
90%
Francine Hung Red Head Part 2
This is the second part of the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in Cali... Read full Story
darrell 2016-11-28 7,076 anal Big Cock deep throat Swallowing Cum
81%
My sisters Tgurl friend
My sister has a friend who is a Tgurl. I didn't know it. I thought she was just a slightly taller hot chick. I'll call her Christy. Well one day I was at my sisters apartment just hanging out when Christy came over. We were watching TV for a while when My sis said she wanted to go over to ... Read full Story
Brett1 2017-06-26 15,172 tranny Shemale Fucks Guy ass fucking cumming jizz
80%
My sisters Tgurl friend Part Deux
Next day, after my incredible sex encounter with Christy , my sister let me know that her friend was a Tgurl. I acted like I was shocked. She told me that Christy was a friend from college and had breast implants and took some hormones to be more feminine, but she still had a dick. My sis told me th... Read full Story
Brett1 2017-06-27 10,665 tranny Shemale Fucks Guy blonde ass fucking deep throat
85%
Gilding the Lilly
It was a dark and stormy night. Oh, wait, I was taught NEVER to begin a story like that. (Snoopy can get away with it, but he does all his writing with a typewriter balanced on his doghouse). OK, getting back to important things. It was actually early Autumn out in the Desert, cool weather was s... Read full Story
CharlotteSlut 2018-03-02 6,439 Group Sex Shemale Fucks Guy gangbang Shemale and Girl shemale + shemale
88%
Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
ASSEaster5678 2018-07-10 11,267 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
69%
Catching Up with A Former T-Gurlfriend
I was jogging one Saturday morning at well known West L A park. I was jogging kind of fast almost sprinting when I came up on woman jogging slower than me. I almost ran into her as I was running. She moved out of my way I slowed down and apologized for being rude. That's when I realized she was a fo... Read full Story
Brett1 2018-08-06 4,786 Latina Shemale Fucks Guy Blowjob cum in mouth
100%
The game show,
One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... Read full Story
chris1989r 2022-01-24 5,391 Bareback Shemale Fucks Guy Ebony gangbang Guy Fucks Shemale shemale + shemale
91%
Banana Fetish
I was 27 and single and enjoying being free sort of the ‘sworn to fun loyal to non’ stage in young adulthood. I lived alone in a 1-bedroom apartment and loved working on my motorcycle which I kept in my living room. Most Friday nights for me were jamming out to music, enjoying a few beers and tinker... Read full Story
AllenB 2023-02-16 10,419 Latina Fetish Big Cock Guy Fucks Shemale Interracial rimming Homemade Ass to Mouth Banana ass eating
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 9,468 Crossdresser Amateur Cumshot Latina Bareback Creampie Shemale Fucks Guy Fetish Blowjob Interracial Homemade cum in mouth
66%
CD Sister play I
I posted an ad in my favorite hookup list seeking a sister CD to come and play with me. None of the dozens of ads I had placed before had received a single response so I expected none this time. I began to assume that CDs tend to regard each other as competition rather than sisters. My ad, includ... Read full Story
PetiteSlutKimberley 2023-04-07 5,525 trap bareback anal sex cd fucks Lesbian Crossdresser
100%
Philippines vacation with a Dominant Big Cock Ladyboy (Part II)
Please read the initial story to get proper context. I spent a 9-day vacation in the Philippines with a sexy and super sweet 34-year old Filipina Ladyboy I met online and developed a relationship with before traveling to meet her. It was the first and only time to visit the Philippines. Less t... Read full Story
AllenB 2024-08-07 4,173 Amateur Asian Ladyboy
100%
My Favorite Trans Model Turned Me in to Her Slut
A couple months ago I was on a trip out in Las Vegas for work. We had some down time after dinner and I was pretty tired of socializing, so I went back to my hotel room to relax. I found myself pretty bored and horny, so I started watching porn and jerking off. I’m married to a beautiful woman, and ... Read full Story
strongjohn518 2024-12-02 2,509 anal Cumshot Bareback Blowjob facial domination virgin rimjob Ass to Mouth gape gaping Hookup topping
66%
Unexpected Festival
Era una noche tranquila y muy agradable con mis amigas. Cena, peli y unas copas rapiditas, nada loco ni fuera de lo normal. Sentadas alrededor de una mesa alta en nuestros taburetes, nos reímos y lo pasamos bien. Era inevitable el echar un vistazo a los que nos rodeaba, había un ambiente wapo y l... Read full Story
IdoiaBoom 2016-01-25 5,142 tranny shemale tgirl sexy ts
25%
Amo la Humillación de Ser Marica
AMO LA HUMILLACIÓN DE SER MARICA  SOY MARICA. Porque ser marica me permite tener el mayor efecto positivo sobre mí y todos los que me rodean.  SOY MARICA. Cada día que vivo como mariquita, confirmo mi humildad a través de la humillación.  SOY MARICA. La humillación no es algo anormal para lo... Read full Story
Marinatvfem 2017-10-16 4,065 Fetish Lingerie Frottage
100%
Mi primo y yo (2da parte (historia con mi vecino))
Bueno ahora toca el turno a la historia que les prometí con mi vecino. Recuerdo bien que todo comenzo un dia que mi primo y yo estábamos solos en mi casa como de costumbre por uno de los tantos viajes de mi familia, ese día me arregle super linda para mi hombre pues había comprado un conjunto de ... Read full Story
Janin 2019-12-27 3,696 Amateur Fetish Blowjob Lingerie Sex Toys Ass to Mouth
100%
Trasformazione: Diventare Una Cagna
Come mi sono trasformato o meglio, come mi hanno trasformato in una femminuccia succhiacazzi, beh, è una storia complicata. Già da ragazzo, appena superata la pubertà, sentivo dentro di me il desiderio di strofinarmi contro il cazzo duro di qualcuno, di baciare con la lingua qualche mio professore d... Read full Story
sami novelli 2021-04-30 1,920 Amateur
100%
Cogiendo con travesti
Hola, soy de Colombia. Siempre he sentido pasión y deseos por las travestis y me encanta su sensualidad y lo femenina que se ven.. Siempre soñaba con estar con una bella travesti hasta que se me dio la oportunidad. Conducía mi moto una noche y de repente en la calle, en un anden, vi a una voluptu... Read full Story
manndick00 2021-06-14 3,143 Amateur Big Tits Outdoor Creampie Fetish Lingerie cum in mouth
100%
Ho incontrato una Dea
Era una tiepida sera di primavera, erano da poco passate le 8 di sera ed io avevo già cenato, era tutto il giorno che mi sentivo eccitata e la voglia aumentava dentro di me, volevo divertirmi un po' con i miei giocattoli anali, però era troppo presto, la serata era troppo bella ed invitante per rima... Read full Story
Sissy Mari 2022-03-17 2,824 tranny Stockings Crossdresser Amateur Cumshot Creampie blonde Lingerie Homemade shemale + shemale sexy shemale sexy tranny
100%
NO TODO ES COLOR DE ROSA EN EL JARDÍN DE NIKITA
Mi nombre es Nikita y soy una chica traviesa,… ¿o debería decir creo que soy una chica traviesa? El hecho es que soy un bonito chico de 23 años. Sé que debería haber sido una chica y seguro que mi cuerpo y mi rostro son muy afeminados. Por lo tanto, no es una gran sorpresa enterarse de que me encant... Read full Story
Panty Kat 2021-07-21 2,124 lenceria sissy panties Panty Fetish calzones Bragas fetiche de calzones
100%
Le due socie
Sono stato invitato da un mio fornitore alla presentazione di un nuovo prodotto, l'incontro mi terrà impegnato solamente il sabato pomeriggio e la domenica mattina e si svolgerà in una località non molto lontana da dove abito, decido di andare. L'hotel è una antica villa in mezzo alle montagne, un... Read full Story
Sissy Mari 2021-08-26 1,589
100%
Paola, una nuova amica
Ho conosciuto Paola sulla chat di questo sito, dopo alcune sere passate a chattare assieme ci siamo accorte che abitavamo nella stessa città. Decidiamo di incontrarci, Paola mi aspetta a casa sua. La sera dopo mi reco da lei, mi aspetta, profumatissima, indossa una lunga vestaglia bianca, i lunghi ... Read full Story
Sissy Mari 2022-03-14 2,198 Crossdresser Amateur Big Tits Cumshot Lingerie shemale + shemale sissy slut sissy crossdresser sissy amateur crossdresser
100%
EL MARIDO DE MI AMIGA 2
Mi amiga no se imagina lo que su marido y yo hacemos. Ella y yo seguimos siendo amigas, pero compartimos el mismo hombre y ella no lo sabe. Yo soy la que le apaga el fuego a su hombre; a ella no le gusta que la penetre por atras, mientras que a mi me encanta sentirla toda. En la cama somos do... Read full Story
IVANNKANAL 2021-12-08 3,116 Amateur Bareback Creampie Fetish Big Cock Homemade
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 1,761 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 1,986 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 1,528 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
50%
IL MIO PRIMO BOCCHINO
IL MIO PRIMO BOCCHINO Domenica scorsa, approfittando di quel poco di libertà che ci rimane, sono andato a trovare una zia e mio cugino un po' più grande di me con gli anni. Sono stato invitato a rimanere a pranzo da loro, dato che abito da solo ho accettato. Finito il pranzo, mia zia e mio cugino... Read full Story
Hermann2 2023-04-18 1,300 Cumshot Blowjob cum in mouth
100%
Lucia_001
Cuando descubrí que me encantaba vestirme de mujer, la verdad no supe que hacer, no solo era una fantasía, era lo que quería desde muy dentro de mí, fue un shock muy grande, del porque siendo hombre me encantaba vestirme de mujer..comprendí que no era normal al promedio de los hombres, porque siendo... Read full Story
Lucía Vanesa 2023-10-27 2,044 Small Tits Amateur Latina small cock sissy travesti crossdresser lucía vanesa Lucia Vanesa Lucy Travesti
94%
Ann
Ann was the woman who gave away free samples in the supermarket where I was manager, and as often as we could, the employees could find us sitting in my office, smoking, laughing and talking. Ann had a way of smoking a cigarette that drove me insane with sexual desire. Inhaling, her lips were pucker... Read full Story
shemale lover 2014-10-27 6,912 shemale fondling
100%
Service Station
I had pulled off the M6 for a much-needed brew and a pit-stop. It was just gone 3am and I was on my way home to Preston from a meeting in London. I slid into a parking space, grabbed my overnight bag, and went into the Travelodge, booked in for one night, got a key, and went up to my room. I d... Read full Story
shemale lover 2011-08-25 2,845 suck shemale stroking
100%
Hawaiian Morning TG Shemale
My clock radio said it was 6:35 in the morning. That means that my annoying alarm would start going off in fifteen minutes or so. But I didn't need an alarm clock to tell me about how my morning was going to be; I felt the playful movements of my beautiful Hawaiian lover behind me. She is a pet... Read full Story
shemale lover 2011-08-27 3,546 asshole Masturbation cum
100%
Shemale Maid
Colleen rushed through the mansion's open gate and headed towards the main door. She opened her mini leather bag and searched frantically for her keys, although she knew she was hopelessly late. Was it her third or fourth unsuccessful attempt in a row to get there on time? Or had there been more? Oh... Read full Story
shemale lover 2011-09-13 5,562 licking sucking Big Cock swallowing
50%
Transgender Art
Artists whose work includes transgender, transvestite, or transsexual themes are rare. In other articles, discuss the work of Christopher Leach ("Christopher Leach") and Kimberly Wilder ("Kimberly Wilder: An Assessment"), whose respective styles, if not subject matter, are vastly... Read full Story
shemale lover 2011-09-17 4,860 transsexual transvestite transgender
66%
The House of Lesslie
I. The mansion hadn't changed, not all that much, from how I remembered it. If at all, it had aged gracefully, as only English mansions can ¬ a massive Edwardian building that had served Lords and Ladies, had housed masters and servants for centuries. Around it, at a respectful distance, w... Read full Story
shemale lover 2011-10-14 6,035 pissing domination Latex
50%
The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
shemale lover 2011-10-18 5,050 Group Sex Masturbation shemale oral
66%
Lana: Second Encounter
Well, you may remember the satisfaction I felt at the end of my first encounter with Lana. I had not really expected to find a CD with whom I felt so comfortable. Usually, I had left my experiences with some discomfort about the surroundings or the person I had been with. Not in this case, she was... Read full Story
shemale lover 2011-11-11 3,539 pantyhose tgirl anus
57%
He thought I didn't know
But although he was careful I found him out. There were the giveaway signs - a lack of interest in sex with me, hidden spunky hankies, that kind of thing. So I checked his internet use and found he'd been surfing shemale sites, pictures, stories and some nasty videos. He seemed to be fascinated ... Read full Story
shemale lover 2011-11-16 3,291 orgasm domination handjob
75%
Singapore tranny sex
My ship was dry-docked in Singapore for 3 weeks, n i was lucky enough to meet a gr8 girl first nite ashore, Lin, half chinese/ half malay, n fucking sexy. I slept at her flat most nites and the sex was awsome. She shared with a girl called Meena, a hostess on Singapore Airlines, but until this speci... Read full Story
shemale lover 2011-11-20 4,851 shemales Group Sex interracial sex
100%
Dressed in holiday style Part 2
I was up by 1 p.m., showered, changed into some fresh panties and donned some hated boy clothes to hit the streets. I stopped by a local coffee shop (not the national chain-brand type) and over a mocha latte the barrista was kind enough to give me a few pointers about where she thought the best holi... Read full Story
shemale lover 2011-11-20 2,328 anal Stockings cum
66%
Tgirl
The year is 2044. My name is Robert. I am 26. Light brown hair. Dark brown eyes. 5' 9", 122 pounds. I work for a supercomputer research and development firm. Like many young men at the leading edge of technology, I am transgendered. My counselor is Dr. Elizabeth Paris. Under her con... Read full Story
shemale lover 2011-11-26 7,711 shemale transformation domination
100%
Becoming Amy
I had been dressing up in women’s clothes since I was a kid. Started with my sister’s clothes, I loved her school uniform. I used to prance around in it when I was lucky enough to have the house to myself, which wasn’t often. I loved pretending I was a school girl, and a rather nau... Read full Story
shemale lover 2011-12-06 7,377 anal shemales bdsm
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,657 toys bondage and discipline chastity belt
80%
Debbie Part 7
As Debbie was led into Dr. Jacobsen's office, she saw that Mistress was already there waiting for her. "Your property Miss Chamberlain", the doctor proclaimed, indicating Debbie. Debbie's heart began to flutter with love and submissive fantasies as she saw Mistress. Mistress was dressed in... Read full Story
shemale lover 2011-12-23 10,032 transgender toys bondage and discipline heavy
100%
Witch Chronicles
I have been asked to write down my perception of the events of the war. After what's just happened, I thought it best to wait and rest before writing things out, but the big wigs want me to get it all down while it's still fresh, so don't expect this to be an extremely military report. I... Read full Story
shemale lover 2012-01-01 6,235 Masturbation orgasm fantasy tg
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 7,279 transsexuals erotica romance crossdressers
80%
Mandy Awakens Dave's Desires
We had been flirting across the bar for several weeks at this point. She was just so easy to talk to. Although she wasn't stunningly beautiful, she was quite attractive. Mandy is about 5'2" or so, 110 pounds. She has a light complexion to go with her strawberry blond hair, which she wear... Read full Story
shemale lover 2012-01-10 5,338 anal sex cum oral fingering
75%
Blue collar Master, white collar slave Part 2
About an hour later I was once again naked except for my chastity pouch and my stilettos and once again I was screaming and crying, my body covered with angry red welts from Master Darren's whip. On my knees crying and begging I held his cock in my hands, trying to give the best handjob ... Read full Story
shemale lover 2012-01-13 11,899 torture extreme fiction bondage and discipline
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 4,867 erotic encounters fantastic consensual