Sort by
Relevancy

Free Stories

80%
Karen, My School Teacher Part 1
The Meet By FoxyHosed It all started when we got a new class teacher. Her name was Karen. She was a mature lady and had dark red hair to her shoulders. That first day she wore some short dark blue jeans and a brown blouse. My other classmates started whispering about her. “He-he! Have you seen t... Read full Story
FoxyHosed 2021-01-29 9,106 Crossdresser Fetish redhead pantyhose Mature pantyhose cd
50%
The Making of A Sissy Part 10
Bella quickly gulped down her vodka and cherry, her bottom tingling with anticipation as her new mature friend gave her a commanding look; she had so enjoyed being submissive for her at the end of a leash, and now she knew she would be bound tightly on a soft inviting bed, and made completely helple... Read full Story
shemale lover 2012-05-29 4,683 dildo oral sex Sex Toys sissy
100%
The Making of A Sissy Part 9
As they sat sipping drinks and discussing what shots would be done indoors or out; Bella’s little cock bulged in her sari as the mature redhead licked her lips as she discussed the ways in which Bella should be trussed, collared and leashed, amongst other things. Sandy stood up suddenly and ra... Read full Story
shemale lover 2012-05-28 3,446 shemales Fetish bdsm 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 2,919 anal Masturbation Fetish
50%
Sissy Amante de la Lencería
HOMBRE AMANTE DE LA LENCERÍA marinatvfem@yahoo.es Tengo 60 años y estoy casado. Llevo muchos años usando ropa interior femenina. Me encanta la sensación del nylon sedoso en mi cuerpo. También duermo con un largo camisón de satén todas las noches. Me siento muy cómodo llevando mi lencería femenin... Read full Story
Marinatvfem 2019-04-01 3,603 Crossdresser Lingerie Frottage
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 4,378 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
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 4,517 anal Fetish little cock sissy
87%
The Making of A Sissy Part 8
The girls sat cross legged sipping orange juice as the day warmed up around them. Roberts’ house had extensive lush lawns beyond the pool which shimmered in the hot sun; the pool looked very inviting to Bella and Roberts looked at the pretty sissy, his mouth watering as his cock pulsed. &ld... Read full Story
shemale lover 2012-05-28 4,444 Fetish sissy
50%
De la pucelle quinquagénaire à la mature disponible...
***Prologue - Confessions: Depuis que j’ai offert ma virginité, je me mets chaque jour un peu plus dans la peau d’une femme. Le petit bled où je vis m’interdit de m’exhiber socialement. Totefois je me suis faite une complice, mon épileuse qui me reçoit après la fermeture . Depuis mon nouveau début,... Read full Story
hippocampus_171 2023-01-11 1,996 Crossdresser Amateur Group Sex threesome Big Cock Mature Homemade cum in mouth shemale + shemale milfs Foursome Bi
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 4,905 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
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 14,223 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
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 1,940 Crossdresser Amateur Big Tits Cumshot Lingerie shemale + shemale sissy slut sissy crossdresser sissy amateur crossdresser
100%
Luna parte 1 “Como me convertí en travesti”
Las aventuras de Luna. Parte 1 “Como me convertí en travesti” ¡Hola a todos! Soy Luna, una travesti de closet. Me encantan leer relatos eróticos de transexuales, mis favoritos son las transformaciones por parte de una novia/amiga/esposa, y pues como he leído tantos relatos y actualmen... Read full Story
Sofia Luna 2021-09-06 2,580 Crossdresser sissy crossdresser
80%
Una giornata in piscina con Paola e Lilly
E' domenica mattina, mi sveglio, sono nel grande letto di Paola, guardo l'orologio sul muro di fronte al letto, sono da poco passate le 11,30. Alla mia sinistra Lilly, alla mia destra Paola, completamente nuda. Anch'io e Lilly siamo praticamente nude, solo calze e reggicalze, ci siamo addormentate... Read full Story
Sissy Mari 2023-05-02 4,256 anal Crossdresser Amateur sissy shemale fucks shemale sissy slut sissygasm sissy crossdresser sissy solo
100%
De drogas, sexo y otros placeres (Primera parte)
-Tienes 30 minutos para ponerte coqueta y bonita. Te espero en el cuarto, así que no te tardes mucho preciosa porque tú y yo la vamos a pasar sabroso ¿Oíste? Tras decir esto Felipe cerró la puerta en mis narices dejándome a solas en la oscuridad de su baño. De inmediato eche seguro a la perilla en... Read full Story
johan3092 2021-07-08 2,582 Crossdresser sissy putita nena convertido
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,476 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
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 8,293 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,544 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
50%
La trasformazione di una sissy parte 1
Ricordo ancora come se fosse oggi la prima volta che conobbi Franco, non so nemmeno io come ma quella sera in cui mia moglie si trovava di turno notturno mi sentivo particolarmente eccitato. La lettura di un libro particolarmente coinvolgente si era impossessata di me. Molte volte mi chiesi se davve... Read full Story
pinkslip 2022-01-06 1,630 Crossdresser Amateur Blowjob Lingerie domination Sex Toys humiliation sissystart
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 26,116 Crossdresser Amateur Lingerie Frottage
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 7,299 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
60%
Fat Indian Crossdresser Slut Gangbang
I am your typical sissy bottom guy who loves mature men. My proportions being large, club me into the BBW category so only the daring types can enslave me. Mature men in the age group 35-60 attract me. Only young guys with very huge dicks are an exception. This is about a naughty adventure of min... Read full Story
shemale lover 2013-03-19 6,355 Crossdresser sucking gangbang ass fucking
71%
Wie ich zur Sissy Schlampe wurde - (1) Prolog
Schon in meiner jüngsten Kindheit trug ich die Schuhe meiner Mutter, rannte lachend in Kleidern umher und stahl Strumpfhosen aus dem Kleiderschrank. Solche Sachen machen die meisten jungen Burschen, denn sowas ist auch nur eine experimentelle Phase und niemand denkt sich was dabei. Wie auch bei mir ... Read full Story
Michelle.W 2018-03-19 60,188 Stockings Crossdresser Amateur Lingerie Sex Toys Solo Shemale
100%
Single sissy in 2024
I’m married, but in law only. Wife and I never fuck; she is a massive prude (naturally only since the ring went on haha). So I dream. Dream about if i lived alone in this day and age. Having fuck machines/massive H cup roanyers/alllll the sexy lingerie delivered directly to my door! I’d... Read full Story
howdyhiddy 2024-06-07 3,859 Crossdresser Lingerie sissy sissy slut fuck machine prostate cum breastplate roanyer
100%
Sissy For My Flatmate Chapter 2
If you've only just tuned in, here's what's going on in my life. Until recently I was a closet crossdresser trying to keep my hobby from my flatmate. When he caught me in the act, I found out that not only had he known about me for a long time but it was a turn on for him. I agreed to become his sis... Read full Story
shemale lover 2012-08-12 3,849 oral sex cum swallowing sissy
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 5,337 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
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 3,823 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
50%
SISSY JESS, COCU PAR MAMAN ⚧️ ⚧️
"Jess, Jess, j'ai besoin que tu m'aides à porter les courses." Jess gémit et, coupable, il souhaita que sa mère demande à quelqu'un d'autre de l'aider. Il voulait juste regarder toutes les autres filles sissy sur Twitter et obtenir son petit « excitation » dur. Il desc... Read full Story
Femboy 2021 2023-03-21 1,143 Stockings Crossdresser Fetish Shemale and Girl Guy Fucks Shemale cum in mouth
60%
The first day of a sissy bitch
She's preparing to become a sissy slut First long and extensive showering then a total shave and she started to turn into the femme of a sissy slut. Naked in front of the mirror, she applied the foundation and spread it evenly across all areas of her face and neck. Next she slipped into her b... Read full Story
sqimyetxräa52 2017-12-19 9,470 Crossdresser Amateur Blowjob Mature cum in mouth
100%
SISSY MARI DE MAÎTRESSE
Morgan Ashley était une très jolie dame, pas une star de cinéma glamour, mais bien plus jolie que tout ce que son mari mauviette Robin attirerait normalement. À peine sortie de la douche, elle portait un peignoir en velours côtelé rouge et ses longs cheveux roux étaient enveloppés dans une serviette... Read full Story
Femboy 2021 2023-01-20 1,237 Stockings Crossdresser Fetish Blowjob Big Cock Lingerie domination Sex Toys
100%
The Twink and the Bear
He stood there, slowly rubbing his hardened cock in the confines of the public toilet cubicle, trousers around his ankles, his legs adorned in black nylon stockings, held in place by the straps of his delicately laced suspender belt. It was so naughty to be playing with himself in a public place, wi... Read full Story
Daddybear71 2023-03-28 4,622 Crossdresser Blowjob Big Cock Mature cum in mouth
70%
My sissy experience
I guess you could call me a sissy, maybe even a whore but one things for sure... I love cock. So my story begins as a young teenage boy, curious like most. I would raid my sisters panty drawer for the excitement of trying on her sexy lingerie. It became an addiction, I couldn't help but want mo... Read full Story
Emilysweetxo 2017-06-26 10,003 Crossdresser solo cd sissy teen cd (18+)
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 34,360 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
100%
Dominated sissy goodgurl34
Mmmm ty Sir Deitrich --I'm standing in your open doorway wearing black latex stockings and garter and some hott red lace panties over top -I have a black corset on and a very sheer dress on ,wig and gurl mask ---my wrists are cuffed to a circle hook one on each side of the doorway door jam about 6... Read full Story
goodgurl34 2022-03-15 2,522 Crossdresser threesome redhead domination Guy Fucks Shemale Sex Toys Homemade shemale + shemale
50%
SISSY, HYPNOTISÉ
Il avait fallu six mois pour en arriver là. En sortant de la salle de bain, je me vis dans le miroir en pied et frissonnai. J'étais rasé sous les sourcils, sans poils et lisse, à l'exception d'une jolie piste d'atterrissage au-dessus de ma cage de chasteté verrouillée. À part la cage... Read full Story
Femboy 2021 2023-02-04 959 Stockings Crossdresser Fetish Big Cock Lingerie Guy Fucks Shemale
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 4,372 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth