Sort by
Relevancy

Free Stories

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 14,246 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
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 4,522 anal Fetish little cock sissy
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 2,008 Crossdresser Amateur Latina Masturbation Bareback Blowjob Lingerie
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 8,303 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
100%
Porn Cinemas and GinaG
I really like porn cinemas, there is a certain seediness and sleaziness about them that makes them alluring to me. My problem is that living as I do in the south of the UK, there are no porn cinemas anywhere near me. Fortunately, I travel in my job quite a bit and so can get to cinemas in Birmingham... Read full Story
GinaG 2019-01-08 3,591 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
85%
Damssel with car distress
I wore sexy stockings and braces, and I put on a short pencil skirt and above the knee before I took the 1979 Saab 99 GL for a ride. That day my old Saab was in real pain and I had to work the shock. When I finally got to drive my old saab, it still sounded a bit sick. It chuggs and squirts a lot an... Read full Story
Jostein 2021-06-08 3,606 Stockings Crossdresser Amateur Outdoor Masturbation car cranking fetish peda pumping
50%
Sissy Boy Chuck devient juste Sissy
Il y a longtemps, j'ai réalisé que j'avais un faible pour les vêtements pour femmes. J'avais l'habitude de me faufiler dans la chambre de ma sœur, la chambre de Jessica et de m'habiller dans ses vêtements. Elle avait un an de plus que moi, mais nous avions pratiquement la même taille. J'ai eu une in... Read full Story
Femboy 2021 2023-01-11 765 Stockings Crossdresser Amateur Fetish Lingerie domination
50%
"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
Femboy 2021 2023-01-20 1,503 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
100%
Sissy Boy’s Secret Desire || Part 6
The room was heavy with the scent of sweat and submission, his body still trembling in the aftermath of what felt like total surrender. She lay beside him now, her presence looming, both comforting and intimidating. He had given her everything—his control, his dignity—and yet, there was an odd sense... Read full Story
shemale_club 2024-10-04 513 Stockings Small Tits Crossdresser Masturbation Fetish domination Sex Toys small cock sissy femboy hentai teen (18+)
50%
SISSY FOR MOMMY'S NIPPLE CREAM
Les chances de Jim de mener une vie normale ont été anéanties avant même sa naissance lorsque son père est décédé dans un accident de voiture. Sa mère, Julia, a fait de son mieux pour l'élever seule, mais elle savait qu'elle ne pourrait jamais être la mère et le père de son précieux Jimmy. Pourtant,... Read full Story
Femboy 2021 2023-01-20 1,355 Stockings Crossdresser Amateur Big Tits Fetish Blowjob Big Cock Lingerie domination
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 60,208 Stockings Crossdresser Amateur Lingerie Sex Toys Solo Shemale
100%
My Sissy, his first time
My fella has always been happy to dress and be a slut for me, suck my dick and take a small dildo in his pussy. Until now I hadn't fucked him properly as he was to nervous. Recently we had been following the exploits of a CD friend through his blog and I knew they really excited my husband. When the... Read full Story
Aplane1 2021-11-01 3,698 Stockings Crossdresser Amateur Cumshot Lingerie Sex Toys
50%
PLACARD SISSY FILS FAIT EN FILLE
Pourquoi étais-je à quatre pattes avec la bite de mon père dans mon cul et la chatte de ma sœur dans mon visage ? Eh bien, je ne savais pas que ma mère connaissait mon secret. Elle savait que j'avais porté la lingerie d'elle et de ma sœur. Tout a commencé quand un jour j'étais seul à la maison et... Read full Story
Femboy 2021 2023-01-20 725 Stockings Crossdresser Amateur Fetish Lingerie domination
50%
PRIS DANS UNE NOUVELLE VIE
C'était mardi soir, ce qui signifiait que Lena se préparait pour son cours d'aérobic. Bien qu'elle ne travaillait pas, elle était certainement occupée à construire et à maintenir une vie sociale et à faire en général les choses qu'elle voulait. Il n'y avait pas un jour où Lena n'avait pas fait qu... Read full Story
Femboy 2021 2023-01-19 1,487 Stockings Crossdresser Amateur Fetish Big Cock Lingerie
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 1,249 Stockings Crossdresser Fetish Blowjob Big Cock Lingerie domination Sex Toys
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 34,405 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 12,139 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
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 2,922 anal Masturbation Fetish
50%
SISSY MARI CHANTAGE ⚧️ ⚧️
La journée a commencé comme n'importe quel autre jour. Vikki se lève à l'aube, prend sa douche le matin et se sèche les cheveux. Ses longs cheveux ondulés brun foncé Lucius tombant en place aussi élégamment, magnifiquement et naturellement que jamais. Avoir l'air époustouflant était une demande si f... Read full Story
Femboy 2021 2023-03-25 1,080 Stockings Big Cock Lingerie Sex Toys cum in mouth maitresse épouse femme dominante force poule mouillé
50%
She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... Read full Story
hippocampus_171 2022-11-22 4,244 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
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 4,307 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
Zoe procures a sissy..Chapter 1.
Zoe Viper sat back on her sofa extremely pleased with how her Friday night was shaping up. Wearing lace top stockings,a tight,black,latex miniskirt with a red satin corset and elbow length,black latex gloves,she took a drag on her blunt. Blowing out the smoke through perfectly painted red lips,she... Read full Story
Jasonlovesatin 2024-06-28 3,061 Lingerie domination sissy
90%
Ginger loses her virginity
My friend's father, Mr Webster, had turned out to be anything but the pillar of the community he pretended to be. Despite his regular Sunday church attendance with Mrs Webster, it transpired he also enjoyed the company of other men. He was certainly enjoying me, and within a few weeks I had fal... Read full Story
Ginger__57 2018-03-26 7,033 Stockings Crossdresser Amateur Bareback redhead
50%
DÉLICE DES VOISINS ⚧️ ⚧️
C'était vendredi, le réveil a sonné ; ma femme a tendu la main et l'a éteint en se levant pour se préparer au travail. J'étais infirmier et j'avais un week-end de trois jours comme d'habitude ; et comme d'habitude, je me suis levé et j'ai préparé le petit déjeuner qui consistait à griller les bag... Read full Story
Femboy 2021 2023-04-02 806 Stockings Blowjob Big Cock Lingerie sissy cum in mouth surprised sexe anal travestisem
100%
Continua mi mundo Tv
Como les decía a mis 20 años ya era otro mundo, ya compraba mi propia ropa intima femenina mas que todo ropita muy chica, pues siempre he sido muy delgad@, a esta edad aun era virgen pero con hombres ya que aproximadamente a los 17 le robe un consolador a una tía, "les admito que ha sido uno de ... Read full Story
Carla Travesti 2018-12-10 2,832 Small Tits solo Amateur Latina Masturbation Fetish Ebony Sex Toys morena flaca venezolana deportista morbosa
69%
How i started feeling like a girl
It was early in my puberty, I was the youngest in my group of friends and many of my them were already dating and having sex with the neighborhood girls. By this time I was beginning to learn more about my body and I noticed more about girls, especially my neighbor's girlfriend, I'll call her Camila... Read full Story
Leah Peaches 2020-01-06 7,667 Teen (18+) Crossdresser solo Amateur Latina
50%
L'INVESTISSEMENT SISSY ⚧️ ⚧️
La fin d'une autre longue journée. Près de 19h00 et Colin Spencer travaillait toujours dans son box, presque terminé avec le dernier des papiers que l'un des associés principaux de la société d'investissement dans laquelle il avait effectué un stage depuis près d'un an maintenant l&#... Read full Story
Femboy 2021 2023-03-21 1,040 Stockings Lingerie domination Guy Fucks Shemale Interracial Sex Toys cum in mouth
100%
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 1,980 anal Crossdresser Amateur Cumshot Latina Fetish Ladyboy gangbang domination Interracial femboy Ass to Mouth double anal
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 1,507 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 9,350 Stockings Amateur cock Masturbation sucking Blowjob Big Cock Lingerie Latex transgender sissy
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 4,390 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
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 3,854 oral sex cum swallowing sissy
100%
Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
shemale lover 2013-01-30 8,108 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
50%
A Shock at the Adult Theatre
I am very often thursdays in the adult theatre, because stylde crossdresser have free entrance at this day. I used to go there by public transportations, because I have no car. In the rear area of the shop we are able to change our clothes and to style up and storing our bags in a locker. About a... Read full Story
SilkeTrav 2020-01-20 8,293 Crossdresser Amateur Outdoor Masturbation Lingerie Homemade
100%
La Entrevista (trabajo de mesera)
LA ENTREVISTA (Trabajo de Mesera) Esta historia es una gran fantasía que tuve por años, pero que ahora aunque a medias es una realidad. Krystal, una de las chicas que me ayuda con el maquillaje, varias veces me había hecho el comentario de que en el bar donde ella actuaba, necesitaban a una chi... Read full Story
Salma TV Pasiva 2023-01-19 1,623 Stockings Crossdresser Amateur Latina Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial
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 3,963 Crossdresser Amateur Cumshot Masturbation Fetish Big Cock kissing Homemade sissy romantic cum swap edging teen (18+)