Sort by
Relevancy

Free Stories

100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 7,119 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
0%
Looking-Glass Ladyboy
I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding ... Read full Story
shemale lover 2011-10-29 7,881 asshole Fetish Ladyboy
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 3,286 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 5,231 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,521 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,773 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
66%
Sissy and Horses
The scariest and best day in my sissy life, was when I was put in a box, tied up, an anal plug in my mouth and a huge bbc dildo in my ass. I was put in the box by my BBC master, who promised me a day of surprises.... I stayed in the box for some hours, my ass hurts of the giant bbc dildo, my mouth ... Read full Story
brunasissyslavedolrj 2024-09-06 2,372 anal Crossdresser Amateur Cumshot Latina Fetish Ladyboy gangbang domination Interracial femboy Ass to Mouth double anal
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 6,347 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
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 14,305 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 34,492 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
66%
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 6,332 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 7,540 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
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 1,414 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
83%
The Making of A Sissy Part 12
Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... Read full Story
shemale lover 2012-05-31 4,556 anal Fetish little cock sissy
100%
The Making of A Sissy Part 11
Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bella’s phone, Ellen tapped in the number to her own phone, and also took down someone else’s number. Ellen smiled wickedly. “I have a very sweet idea, but ... Read full Story
shemale lover 2012-05-31 2,960 anal Masturbation Fetish
100%
Dating my Sissy-sister (English)
You are wearing women's stockings and a thigh-high transparent top, the thin shoulder straps of which leave your arms and shoulders elegantly exposed! You're the real lil bunny to me in that girl outfit of yours... How about, should I teach the little one about the naughty girl? You're giggling a... Read full Story
LulaSissy 2024-09-24 2,761 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female fucking sissy
78%
How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
Tvtrinity 2016-08-29 72,367 Teen (18+) Crossdresser transgender sissy slut.trinity
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 4,064 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
100%
SOUMISSION BBC DE SISSY
« Tyler ! Arrêtez-vous – vous regardez à nouveau, et il l'a remarqué ! » La voix de Jack chuchota d'une voix rauque à l'oreille de Tyler alors que l'eau chaude de la douche tambourinait dans son dos. Il ne restait plus que les trois sous la douche maintenant. L'entraînement de basket-ball était t... Read full Story
Femboy 2021 2023-01-24 1,714 Stockings Teen (18+) Crossdresser Fetish Blowjob Big Cock Lingerie domination Guy Fucks Shemale Interracial cum in mouth
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 4,049 sucking Fetish Ladyboy rimjob
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 2,157 Teen (18+) Amateur Latina Bareback Fetish Ladyboy domination Homemade
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,422 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
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 7,868 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
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 3,885 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
50%
LE NOUVEAU SISSY CLUB ⚧️ ⚧️
Il y a de nombreuses années, lorsque Craigslist était populaire pour les rencontres et les rencontres sexuelles, j'aimais lire les publicités. Je suis tombé sur une annonce dans la rubrique "Hommes à la recherche d'hommes". Il s'intitulait "Sissy Club Forming". Le titre m'a intrigué et quand j'ai cl... Read full Story
Femboy 2021 2023-04-13 1,183 Stockings Fetish Lingerie homosexual sissy
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 1,502 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 1,722 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 1,273 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,617 Teen (18+)
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 14,415 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
50%
PREMIÈRE ÉTAPE FÉMINISANTE
Aujourd'hui, ma mère et moi sommes allés acheter des maillots de bain dans un grand magasin local. C'était en début d'après-midi et nous avions pratiquement l'endroit pour nous tous seuls. En entrant dans le magasin, nous sommes passés devant une grande colonne couverte de miroirs, et je me suis ... Read full Story
Femboy 2021 2023-01-27 1,090 Stockings Teen (18+) Small Tits Crossdresser Fetish Lingerie domination Sex Toys
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 6,501 Stockings Teen (18+) Small Tits Crossdresser solo Amateur Masturbation Asian Ladyboy Lingerie Homemade webcams
100%
COMMENT NATHAN EST DEVENU NATALIE ⚧️ ⚧️
Je m'appelle Natalie mais ce n'est pas le nom avec lequel je suis née; c'est plutôt le nom que ma femme m'a donné quand elle a fait de moi sa "sœur" et sa poule mouillée cocu peu de temps après notre mariage. Mon vrai nom est Nathan mais c'est un nom que je préférerais ne plus jamais utiliser parce ... Read full Story
Femboy 2021 2023-04-23 1,962 Teen (18+) Blowjob Lingerie Sex Toys small cock sissy cum in mouth sissify poule mouillée et fille premiere foi
100%
LE CONTRAT DE MARGOT
Madame Margot Elizabeth Stott était l'objet de mes désirs, des désirs très secrets ; désire que je n'aie jamais eu l'intention de la laisser - ou qui que ce soit d'autre - le découvrir. Mme Margot Elizabeth Stott avait, au moment où je l'ai connue pour la première fois, environ 45 ans, peut-être ... Read full Story
Femboy 2021 2023-02-16 1,366 Stockings Crossdresser Cumshot Fetish Lingerie domination Sex Toys cum in mouth
100%
Edging lessons for Hannah
Hannah and I began spending our weekends together. She didn't have a job and I was always free those days so every Friday or Saturday night became sleep over night where we could be two 18 year old sissies, doing each others makeup, playing dress up and sharing our deepest desires. Now that our rela... Read full Story
KaceyKlarissa 2024-01-25 3,993 Crossdresser Amateur Cumshot Masturbation Fetish Big Cock kissing Homemade sissy romantic cum swap edging teen (18+)
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,310 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov