Sort by
Relevancy

Free Stories

100%
Diary of a Sissy
Dear Diary, This time I fucked it up for good... I am completely lost in the viscous cycle of sissy hypnosis. My beta girl nature was starving to be controlled by superior men. The desire to be owned was so intense that made me do something I have never done before in my whole life.. this time I ... Read full Story
KittyHot 2023-12-21 7,244 Amateur Cumshot Fetish domination climax sissy chastity cage sissification master daddy teen (18+) mental domination
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 9,903 Latina Fetish Big Cock Guy Fucks Shemale Interracial rimming Homemade Ass to Mouth Banana ass eating
94%
SISSY RULES!!!
There are a few things a sissy must understand in order to attract, and then keep, her man. Let’s look at them, these Sissy Rules. (✿◠‿◠) 1. Men are superior to you. This is rule number one for good reason: it is a simple statement of fact. It is so important that many questions that a potent... Read full Story
KittyHot 2021-06-18 8,224 Crossdresser Amateur Fetish submissive feminization sissy submission femboy hypno beta obedient
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 4,150 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
My 1st Time was Not the Only Time.
One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... Read full Story
LesFuax 2019-02-16 9,110 first time Small Tits Amateur Latina Bareback Creampie threesome Blowjob Big Cock ass fucking barebacking barebackedshemales first time with a tranny raw anal raw dick raw fucking firsttime
100%
Dos amigas trans
Hola!!! Soy Karina, tengo 21 años; soy una chica transexual; mido 1,75 m; peso 62 kg; soy morocha, pelo largo lacio negro; ojos marrones; buen cuerpo, tetas medianas y pene pequeño. Mi cola es atractiva y me gusta mucho vestirme con ropa ajustada. Soy muy femenina en mis posturas y gestos. La histo... Read full Story
roberto4771 2019-03-07 3,418 Teen (18+) Amateur Creampie Blowjob Frottage cum in mouth shemale + shemale
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,065 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
MY First Time with a non-binary/cross-dresser
After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... Read full Story
ghostpeople 2019-03-12 7,082 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,316 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
57%
Oh Astrid!
Like most here I have watched a lot of porn over the years, AST being my favourite site and having enjoyed a lot of she ick beauty of all types, ages and descriptions it became my custom to sample, in real life what pleasures the cock of a beautiful tranny may provide. Most of the escorts visited... Read full Story
Kinky Dee 2017-11-09 6,086 tranny Latina Fetish Blowjob Big Cock
100%
Entrevistando a la hermosa Vanessa Guzman
Hola Vanessa, gracias por tu tiempo para esta entrevista, comenzamos. ¿Por qué escogiste llamarte Vanessa? Escogí ese nombre porque en uno de mis viajes a Guadalajara, conocí a una chica trans que se hizo mi amiga y fue ella quien me bautizo con ese nombre y desde ahí decidí llamarme Vanessa.... Read full Story
Vanessa Guzman 2020-01-06 2,617 Teen (18+) Crossdresser solo Amateur Latina
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 1,142 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
100%
La Mujer Trans más feliz del mundo.
- Porfavor, no pares Gaby! - Le gritaba yo, completamente llena de placer, mientras a 4 patas aguantaba sus grandes embestidas, a la par que mis grandes tetas chocaban entre sí. - Ya casi me voy a venir Juanita! - Dijo ella, mientras trás de mi daba todo de si para hacerme sentir en el paraiso, s... Read full Story
DaphneYuki 2023-10-28 1,862 anal Amateur Big Tits Latina Bareback Creampie Blowjob Big Cock Interracial shemale fucks shemale doggystyle story line
50%
Minha primeira experiencia CD REAL [PORTUGUESE]
Não é uma ficção, essa é a minha história de verdade. Primeiramente, como toda história desse tipo, vou me descrever. Sou branquinha, 1,73 de altura, 60kg, magrelinha, meu corpo e rosto são um pouco femininos mas não tenho atitudes afeminadas, sou mais andrógeno do que femboy, olhos e cabelos casta... Read full Story
Nyxie 2020-05-04 1,842 Crossdresser Amateur Latina Masturbation Bareback Blowjob Lingerie
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 10,020 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
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 8,874 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
100%
CONTES DE FEMMES TRANS TOPS ⚧️ ⚧️
Être coincé au bureau tard un vendredi, c'est toujours nul. Alors que je remarquais que des subordonnés et des collègues quittaient le bâtiment alors que l'horloge sonnait cinq heures, certains d'entre eux s'arrêtant à la porte de mon bureau pour me souhaiter poliment un bon week-end... Read full Story
Femboy 2021 2023-03-19 891 Shemale Fucks Guy Fetish Blowjob Big Cock cum in mouth transexuelle
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,642 Stockings anal sex Fetish Interracial sissy
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 13,844 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
71%
CÓMO SER UNA BUENA SISSY MARICA
CÓMO SER UNA BUENA SISSY  VARIOS COMPORTAMIENTOS: Pasiva, sumisa, perezosa, dominada, obediente, frágil, vulnerable, indefensa, mansa, cariñosa, dulce, encantadora, cálida, blanda, bella, sexy, afeminada, suave, amable, dócil, respetuosa, delicada, débil.  EROTISMO CON LA LENCERÍA: Después cogí... Read full Story
Marinatvfem 2017-10-16 25,887 Crossdresser Amateur Lingerie Frottage
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 33,771 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
Mi primera vez con una trans.
La semana pasada estaba viendo porno como siempre lo hago, siempre mezclo entre el porno tradicional y el porno de aShemale. ya que bajo cierto punto de vista, me consideraba bisexual y ver a las traviesas me volvía loco, siempre deseaba penetrar esas colas mientras las bolas le colgaban. Eventua... Read full Story
ceresitanueva 2019-08-06 5,165 Teen (18+) Bareback Shemale Fucks Guy Fetish redhead domination Ass to Mouth
50%
Unexpected Threesome Experience
Last weekend I hook up with a British man. He was 40s year old and we were supposed to meet at a hotel. When I arrived at the hotel, he was there, we talked briefly, and then we started having sex. He suggested I wear a blindfold and I accepted because I enjoy doing it. While I was blind... Read full Story
cdmisato 2024-07-16 688 Crossdresser Amateur Group Sex Asian sissy
85%
My shopping trip to San fransico with nucle jim pa
That night at dinner uncle Jim told my mom that he had to go to the city to pick up some film and things for his dark room. He ask if I could go along with him. My mom said yes that I could go. We would be leaving around 8 and that was fine with her. She did not go to work till 12 because she worked... Read full Story
shemale lover 2012-09-13 3,655 Fetish Lingerie facial sissy
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,166 sucking Fetish Uniform domination big boobs
77%
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 71,734 Teen (18+) Crossdresser transgender sissy slut.trinity
93%
Sissy Experience - Episode 1: The Beginning
Hello All, Hope you’re all doing well!! This story narrates the beginning of my crossdressing and sissy adventures. Before I begin I’ll tell you somethings about my family. We are a family of four consisting of me, mom, dad and an elder sister. I am currently 20 years old and in college. My da... Read full Story
brownsissyboi 2020-05-15 8,103 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
100%
Deflowering Latina Sissy Destiny
A real life story of my one and only time deflowering someone and being their first real encounter, I was 27 at the time and she was 21. I am absolutely convinced that Trans girls and CDs have a bit of a 6th sense when it comes to perceiving which guys are into them even in a public situation. I ... Read full Story
AllenB 2022-09-07 6,324 first time Big Cock Guy Fucks Shemale Homemade sissy travesti cum in mouth
50%
DEVENIR CASSIE
L'argent était difficile à trouver dans notre foyer. Être l'aînée de quatre enfants et ma mère étant une mère célibataire mettent nos ressources à rude épreuve. Nous avons rarement eu de l'argent supplémentaire dans notre famille à dépenser pour des choses comme manger au restaurant ou aller au ciné... Read full Story
Femboy 2021 2023-01-20 1,491 Stockings Crossdresser Amateur Cumshot Fetish Blowjob Big Cock Lingerie domination
50%
Sissy Acceptance *
La primera vez que vi porno interracial algo recorrió mi interior de una manera que nunca antes había experimentado, era como un hormigueo que pasaba por todo mi cuerpo….. hasta llegar a mi ano. No sé que fue lo que me motivo más si la insaciable obsesión por probar una verga negra, ó el hecho de... Read full Story
Sissycrick 2023-05-04 1,294 anal Small Tits Crossdresser Amateur Latina Bareback Blowjob Big Cock Lingerie Interracial sissy femboy e
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 8,877 Stockings Amateur cock Masturbation sucking Blowjob Big Cock Lingerie Latex transgender sissy
100%
Dancing at a trans club by chance
I'm working part-time at a trans club these days, but I'm still only working on serving. But by chance, the boss suggested that I try dancing on the pole dance stage in the center of the club. I was embarrassed because I was not good at dancing, but people around me suggested me to dance once,... Read full Story
cdmisato 2024-03-30 3,889 Crossdresser Amateur Asian Ladyboy sissy
85%
Black Master, white sissy Part 2
I was a romantic despite the cynicism I projected in my job. This tough black skinhead yob had abused me - he had shaved me, humiliated me and yet for the next week what I remembered most was the kiss. Sure, the abuse had touched something in me but until I had met him it was unacknowledged - someth... Read full Story
shemale lover 2011-11-23 10,414 shemales Fetish bdsm
72%
First Time Sissy Maid
I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... Read full Story
shemale lover 2012-10-27 16,896 first time Fetish Big Cock domination sissy
88%
Mi primera vez de travesti con mi novia
¡Hola a tod@s! ¡De nuevo estoy aquí contándoles una nueva aventura con mi novia y como cada vez me vuelvo mas nena! Bueno, les voy a contar la primera vez que me vestí con ella y tuvimos sexo como niñas.... mmmmm.... ¡delicioso! Después de enseñarle mis fotos mas lindas, vestida de nena lin... Read full Story
Sofia Luna 2019-09-19 4,543 Crossdresser Amateur Latina Fetish Blowjob Lingerie Shemale and Girl Homemade
50%
Sissy pour un jour
Certains appelleraient cela une crise de la quarantaine ... même si je n'ai que trente-cinq ans et j'espère que je n'ai pas encore atteint le milieu de ma vie. Certains me traiteraient de pédé ... même si j'adore manger la chatte et baiser ma femme. Certains appelleraient cela ... Read full Story
Femboy 2021 2022-12-08 1,218 Crossdresser Fetish Sex Toys