Sort by
Relevancy

Free Stories

90%
First Outdoor Fuck
Sat in my office with nothing to do was making me tired there was no customers to serve which was slowly driving me mad, what was worse was the hot weather outside which always makes me horny, knowing I had all my girly clothes in the boot of my car was making my cock twitch in my cheap nylon work t... Read full Story
shemale lover 2012-12-19 6,492 Crossdresser Outdoor ass fucking pantyhose heels
100%
First time with a cute ladyboy
It had been a long week at work. So I decided to go to the Sound Factory for a drink and maybe get lucky with the ladies. As soon as I got to the bar, I spotted a beautiful asian lady wearing leggings with pantyhose and a sexy little top. She offered to buy me a drink, who am I to refuse. So we had... Read full Story
shemale lover 2013-05-07 11,197 Cumshot suck Asian Ladyboy pantyhose
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 5,780 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
100%
CLUB FUTANARI
Lisa Une fille timide de 20 ans avec de longs cheveux, de beaux seins, une chatte humide et un gros secret sous la forme d'une bite géante. Elle a vécu une vie protégée mais est bientôt en route vers un nouveau monde de sexe lesbien. Marie Médecin de plus de 40 ans spécialisée dans les ... Read full Story
Femboy 2021 2023-02-13 1,533 Crossdresser Cumshot Fetish Shemale and Girl domination Futanari
50%
AGENCE D'ÉLEVAGE FUTANARI partie 2
« Suspendu ? Comment ça, je suis suspendu ? » dit Alina. "Je n'ai pas vraiment le choix. Zut, je pense que je suis gentil de ne pas vous dénoncer à la police. Vous l'avez mise enceinte pour l'amour de Dieu", a déclaré le principal Pulcher. "Mais je n'ai jamais été s... Read full Story
Femboy 2021 2023-02-13 1,109 Crossdresser Fetish Blowjob Shemale and Girl domination Futanari
50%
AGENCE D'ÉLEVAGE FUTANARI
Cela ressemblait un peu à de la prostitution, mais elle était convaincue que c'était le seul moyen pour elle de payer ses études. Elle était assise dans un bureau chic, à côté d'une femme professionnelle bien habillée. Sa famille n'était pas aisée et la seule option pour payer ses étu... Read full Story
Femboy 2021 2023-02-12 1,240 Crossdresser Cumshot Fetish Shemale and Girl Futanari cum in mouth
100%
ladyboy Yaqi
After graduating, she began to wear women's clothing to work all day for a month. After Yaqi went to work in this company, she had to wear tight dresses and stockings and high heels every day. After a long time, she also got used to the close-fitting feeling of wearing pantyhose. More importantl... Read full Story
Victor Chen 2023-03-23 5,301 Asian Ladyboy
91%
My First Ladyboy
I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers. This particular Friday we were in the usual place chatting and having a nice relaxing time. When she walked in. Taller t... Read full Story
shemale lover 2013-08-09 13,217 Cumshot Asian Ladyboy big boobs
80%
I got humiliated in a catfight
Im a crossdresser and I am very feminine and extremly dainty. I was attracted to a man at a park I went to. He knew I was a crossdresser. I would always say hi when I saw him, but that was it. One day he asked me(on a rainy day as I was getting in my car), do I have a boyfriend am I bi, he wanted to... Read full Story
Kaylamoore994 2023-03-26 6,381 Crossdresser Outdoor Masturbation Fetish Ebony Ladyboy Lingerie humiliation fight sissy crossdresser catfight
75%
Becoming Carla's Girlfriend
Carla and I were watching Netflix at home just relaxing after a long day of work. I remember laying down next to her and looking at the pink toenail polish on her feet. I taunted her as said "I could do a much better job painting your toes than you could." Carla smirked and said, "It's much ha... Read full Story
lacemint 2023-08-19 7,084 Stockings Crossdresser Lingerie pantyhose fantasies crossdresser lingerie nylon stockings nylons crossdresser panties crossdresser
100%
Karen, My School Teacher Part 3
Regret... Hmm Maybe Not. By FoxyHosed My excuse for a cock got hard again. My horniness got the better off me. I went to lock the front door. I took my shoes, pants and sweater off. I stood in the hallway only in pantyhose and t-shirt. ‘Don't do this. Walk away from this now. But you go to boa... Read full Story
FoxyHosed 2021-02-05 8,866 Crossdresser Cumshot Fetish Blowjob pantyhose pantyhose anal crossdresser guy fucks crossdresser
100%
Dogging in the Park
The last two nights have been great fun in our local park. There is a parking lot where guys gather after dark and I was one of them. Both nights I was dressed up as a slutty CD with a black bra, fake silicone tits, black pantyhose and a short miniskirt. First Night: After waiting about an hour a... Read full Story
Rocky8844 2024-04-02 4,404 Crossdresser Outdoor Blowjob
100%
A Crossdresser Gets Fitted
Not long ago I was out shopping and stopped at one of the clothing outlet stores that I frequent when looking for sexy clothes and shoes to wear when I go out clubbing or to wear in my adult videos. I was looking through the display rack of my favorite brand of pantyhose, trying to find the colors I... Read full Story
shemale lover 2012-02-25 5,229 Fetish threesome orgasm pantyhose crossdressing
100%
Crossdresser 1st time!
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
shemale lover 2013-05-30 8,119 Outdoor Big Cock fingering ass licking virgin public cd piss
69%
Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
Stud4Shemale 2017-05-22 7,711 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
100%
Lustful Crossdresser by CDlishmis
As I think about the way I feel when I dress in women’s clothes. I become agitated with myself. I can’t stop. I couldn’t stop even if I wanted to, it is an addiction. The physi cal and mental transformation that I go through is ex... Read full Story
cdlishmis 2020-08-31 3,367 Crossdresser Blowjob gangbang Lingerie domination cum in mouth psychological
100%
The reason why I became a crossdresser
At first, I was just a straight and ordinary boy who was into sexy lingerie, stockings and heels. But one day, I suddenly thought that I wanted to try on my mom's panties, stockings, and high heels. So I did it. It was so excited and I started to get addicted to cross-dressing. Before dres... Read full Story
cdmisato 2024-02-28 6,949 Crossdresser Asian Ladyboy sissy
100%
From boy to crossdresser episode 3
My days and nights were spent with porn and sexy stories and masturbation. I used to cum every day for some reason. First, when I got older, I felt that my breasts were bigger than usual, I thought to myself that maybe I am a girl. I used to sneak out and take a bra from my mother's clothes and p... Read full Story
Nickinickharddick13 2024-09-02 1,704 Crossdresser Amateur masturbate
100%
Lope
Je suis une salope C’est un des fantasmes récurrents de la majorité des hommes qui aiment se travestir. Et j’avoue que l’idée m’a souvent excitée. Alors que j’étais avec ma femme dans une boutique de lingerie à Pigalle , des dessous très sexy entre les mains, un homme d'un certain âge a surpri... Read full Story
osvp75 2021-11-12 1,576 Stockings Crossdresser Cumshot Outdoor Masturbation Fetish Ladyboy Lingerie domination Premium HD
50%
La pistola NEGRA del Tío, entre Las Bragas de Mi Tía LA PUTONA
Aaayyy.. Yo sabía que la Tía había sido Flor de PUTONA.. pero, jamás me imaginé que me iba a tocar a mí 'hacerme cargo de sus cosas'.. su 'herencia'.. la casa ya vieja, por reordenar destinar y.. LAS COSAS que una descubre ya con los años! Todo estaba igual, pero HORRIBLEMENTE ARRUINADO.. más, e... Read full Story
Ari Riè 2021-06-03 2,331 Teen (18+) Small Tits Crossdresser Latina Bareback Shemale Fucks Guy Fetish blonde Big Cock Uniform Lingerie domination Premium HD
75%
A Futa Futcha
This story depicts a fetish know as Futanari Fuatnari: A type of Hentai, most often depicting hermaphrodites or females with male sex organs. Also known as Dickgirls. Transformation Futa is a long standing kink of mine, though it has been a while since I indulged. The major difference is that ... Read full Story
shemale lover 2011-10-29 8,883 Fetish Futanari dickgirl
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 6,157 anal Cumshot Ladyboy oral
100%
FOUTAREICH
Le Parti de l'apothéose féminine, ou FAP, a reconnu les différences physiques entre les hommes et les femmes. Cependant, la FAP a affirmé que même si les femmes pouvaient être physiquement inférieures aux hommes, elles étaient moralement supérieures. Tant que les hommes seraient plus forts que l... Read full Story
Femboy 2021 2023-02-11 1,347 Crossdresser Cumshot Shemale Fucks Guy Shemale and Girl Futanari cum in mouth
44%
Gargantua
Women do not have penises or testicles. These sex organs are specific to men. As the boy in Kindergarten Cop demonstrates, even young children are aware of this most fundamental fact of life. However, in the genre of erotic fantasy art known as futanari, hermaphroditic "dickgirls" defy nat... Read full Story
shemale lover 2011-09-12 7,867 Futanari dickgirl big cocks
100%
Karen, My School Teacher Part 5
The Bus Station By FoxyHosed I looked around, but no one was there. It was dark and pretty cold night outside. I felt the air blowing around and up my pantyhose encased legs and ass. Mmmm nice. I started walking to the bus stop a few blocks further down from the school. I felt very attractive g... Read full Story
FoxyHosed 2021-03-15 7,384 Crossdresser Cumshot Outdoor Masturbation Fetish Blowjob pantyhose legs pantyhose cd
50%
FORMATION D'AMOUR
Kyla essuya la sueur de ses yeux, puis essuya le liquide de sa main, tout en s'appuyant sur son balai. Ce putain de jour était trop chaud, bien trop chaud. Elle regarda autour d'elle : le vestiaire vide était complètement immobile, attendant patiemment d'être nettoyé, son air saturé d... Read full Story
Femboy 2021 2023-02-10 1,032 Crossdresser Shemale Fucks Guy Fetish domination Futanari cum in mouth
50%
RANCUNE MATERNELLE ⚧️ ⚧️
"... Dois-je être ici?" Cole a demandé anxieusement. Sa mère s'était détournée de lui, occupée à sortir plusieurs plateaux de lasagnes du four. "Je peux rester chez un ami ou quelque chose comme ça..." Christina, comme sa mère s'appelait, soupira profondément. "C'e... Read full Story
Femboy 2021 2023-03-19 1,126 Teen (18+) Blowjob Big Cock Futanari cum in mouth Mère Futa et Fils inceste
100%
Crossdressing at CCBC in Palm Springs
I recently stayed at CCBC in Palm Springs. For those of you who are not aware of it, it is the largest gay resort in Palm Springs area. The resort has about 30 rooms, lockers, a pool, steam room and indoor and outdoor play areas all on a one acre outdoor enclave. I arrived there on a Tuesday and dre... Read full Story
Rocky8844 2024-05-27 4,169 Crossdresser Group Sex Blowjob Lingerie pantyhose cum in mouth
66%
Ladyboy dominatrix
If you read my other stories you know I'm intersexed and I was a ladyboy prostitute when I was um, very young. I don't condone such activities. They were sick perverts who used me. True I got a lot of money and expensive gifts but that doesn't make it right. They should all be castrated. Th... Read full Story
shemale lover 2012-10-15 10,199 Fetish Asian domination sissy rimjob
100%
I Missed Myself
As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... Read full Story
shemale lover 2013-03-20 8,230 Crossdresser Lingerie pantyhose cd softcore
62%
Crossdressed Lana - Hannover, Germany
Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... Read full Story
Crossdressed Lana 2020-02-06 4,522 Stockings Crossdresser Group Sex Outdoor Bareback Fetish Blowjob gangbang Lingerie domination Latex Sex Toys double anal
90%
Oh What A Night
Oh What A Night! As the old 4 Season's song stated, oh what a night. Having been a crossdresser on and off my entire life, I have done the old collect and purge routine too many times. After putting Jennifer away several years and relationships ago, the old urges returned recently. Having lost ... Read full Story
JenniferJones 2019-01-21 4,924 Crossdresser Amateur Outdoor cum in mouth
86%
My First Ladyboy
I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers.. This particular Friday we were in the usual place chatting and having a nice relaxing time......when she walked in....t... Read full Story
shemale lover 2015-05-23 8,746 anal Blowjob Asian
91%
Verbotene Einfahrt in den Wald
Ich hatte mich entschlossen bei den letzten schönen Tagen des Sommers in den Wald zu fahren um dort ein Shooting mit meinen neuen Strumpfhosen zu machen. Guter Dinge fuhr ich zu einer mir bekannten Stelle in unserem schönen bayrischen Wald. Ich fuhr einen kleinen – offensichtlich ungenutzten – Waldw... Read full Story
Nylon_Lottchen 2020-02-13 4,847 Crossdresser Amateur pantyhose nylon outdoor sex kerl fickt trans
100%
My story, more or less pt.3
Earlier on, when I was scouring through various drawers and closets for feminine clothes in my home I have stumbled upon two old skipping ropes. "A fun time" I thought to myself, not giving them another look and continuing with my search. Little did I know they would become the backbone of my "sessi... Read full Story
Thigh_High_Boi 2023-01-06 3,848 Stockings Masturbation Fetish Ladyboy Lingerie Homemade pov
50%
IODE VIOLET ⚧️
Meranda avait fait partie du projet militaire d'Athéna. Elle était, très grande pour une femme, environ six trois. Elle se réveillait toujours à six heures sans problème. Ensuite, elle faisait ses cent pompes. Malgré son conditionnement, elle avait toujours une taille de poitrine substantielle q... Read full Story
Femboy 2021 2023-02-11 1,174 Teen (18+) Crossdresser Fetish Futanari cum in mouth shemale + shemale
50%
PLAIRE À LA FUTA
Linda s'est arrêtée à la maison de banlieue. Elle a dû se garer dans la rue car elle était déjà pleine de voitures. Elle le savait déjà, puisqu'elle était en retard, et qu'elle allait rencontrer cinq autres ménagères. Ils avaient tous des filles du même âge que sa fille, et maintenant qu... Read full Story
Femboy 2021 2023-02-12 1,059 Teen (18+) Crossdresser Cumshot Big Cock Shemale and Girl Futanari
100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,386 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,579 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
100%
Feriengruss 20.07.24
Erneut ging es Outdoor, dieses Mal aber an die Thur zum FKK Baden. Nicht am bekannten Platz in Bischofszell, sondern an meinen geheimen Platz, zwischen Kradolf und Bischofszell, unterhalb von Halden. Ich habe erneut mit 5 verschiedenen Herren abgemacht, die mir in gut geplantem, zeitlichem Abstand... Read full Story
Cheryl_F 2024-09-03 200 anal Small Tits Amateur Cumshot Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy pov Ass to Mouth
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 8,249 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
100%
My story, more or less Pt.1
I always knew I was different. I enjoyed playing with dolls and being around girls, I felt safe and in my place. When I got my first smartphone I have discovered porn, and boy was it an adventure! I have watched every type you can think of, but eventually I settled on shemales, the perfect cross ... Read full Story
Thigh_High_Boi 2022-12-22 4,957 Stockings Cumshot Masturbation Ladyboy Lingerie Homemade pov
100%
A Religious Experience
A Religious Experience by Sabrina G. Langton *Stories from the real world 2 This story is kinda autobiographical. I was twenty-two in 1987. You couldn't just order anything you wanted on the computer, with no social interaction, and get whatever you wanted. You had to go out in the real w... Read full Story
Brina Giselle 2023-09-13 5,215 Crossdresser pantyhose transgender bisexual footjob dress
100%
Reaching Paradise on Game Night
Reaching Paradise on Game Night by Sabrina G. Langton * Author's note: Here is one of my most popular stories. I get so many messages and emails about it and it makes me thrilled. I am so glad it has taken on a life of it's own. 'A wife learns a little too much about her crossdressing hus... Read full Story
Brina Giselle 2024-08-08 2,918 anal Stockings Crossdresser Blowjob pantyhose transgender wife dress-up
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,534 Crossdresser Cumshot Blowjob jerking pantyhose
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,729 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
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 14,288 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Lady In The House Ch. 08
A story by MicheleNylons (Crossdresser must comply with jailhouse heavy.) "You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by... Read full Story
✘Transensual✘ 2019-02-25 5,948 Crossdresser domination PRISON PUNK prison sex Prison Bitch
100%
Karen, My School Teacher Part 2
Just Staying a bit By FoxyHosed “Don't mention it. Now let me start on the pasta with meatballs!” She stood up from her chair “And besides, it will be nice to have someone to eat with, for a change!” She went to the kitchen to start dinner. “Make yourself feel at home!” I watched some TV ... Read full Story
FoxyHosed 2021-02-01 11,428 Crossdresser Fetish pantyhose Mature pantyhose cd
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 8,042 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
80%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 5,040 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,647 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
50%
EXPLORER LA JUNGLE FUTA
Alors que Mandy se déplaçait dans la jungle, elle réalisa qu'elle était désespérément perdue. Repoussant les branches et les feuilles, elle poussa un soupir d'agacement face à la même clairière qu'elle avait rencontrée auparavant. "Bon sang." Étirant ses bras et écartant ses c... Read full Story
Femboy 2021 2023-02-10 1,265 Crossdresser Cumshot Shemale Fucks Guy Big Cock Futanari cum in mouth
50%
Feriengruss 16.07.24
Heute habe ich endlich jemanden gefunden, der mir einen langersehnten Wunsch erfüllen wollte. Ich wollte, nackig unter dem Mantel und nur bekleidet mit eingeschnürten Titten, durch die Stadt geführt werden, während ich gefilmt wurde. Wir machten ab, als es in Weinfelden gerade einzudunkeln begann. B... Read full Story
Cheryl_F 2024-09-03 308 anal Amateur Cumshot Outdoor Bareback Fetish blonde Big Cock Ladyboy domination Guy Fucks Shemale Homemade pov
45%
Becoming Alanna Part 1
My name is Alanna Monroe and i am currently a college bound 17 year old senior at St. Anne's school for girls in Middletown Conn. I was once Alex Monroe, but after one fateful day four years ago, I became Alanna. Being a proper “lady”, i have all of the assets of my classmates...well tha... Read full Story
shemale lover 2012-07-12 5,132 shemales Ladyboy
40%
Kitten: A Pantyboy StoryKitten: A Pantyboy Story
It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first ... Read full Story
shemale lover 2012-09-10 7,256 Crossdresser fingering Sex Toys handjob 69