Sort by
Relevancy

Free Stories

100%
Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
✘Transensual✘ 2019-02-27 5,930 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 7,060 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
91%
The Beginning Of Penny
This story is about how I became Penny, the cock loving, tranny. I remember being a kid and jerking off to dirty mags we stole from my friend’s dad. The pics that always made me hottest were the ones in the ads in the back few pages for phone sex with trannies. Looking at those hot and perfect women... Read full Story
pennypenny 2017-05-29 10,683 Crossdresser Blowjob Guy Fucks Shemale 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 14,116 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
50%
ÉTÉ ⚧️ ⚧️
Je ne me souviens pas exactement où ma fascination pour les choses féminines a commencé. Mon premier souvenir remonte à l'âge de six ans environ, lorsque je portais une des robes de ma sœur. Mes parents - qui étaient tous deux des conservateurs de la vieille école et des chrétiens - m'ont at... Read full Story
Femboy 2021 2023-03-23 398 Teen (18+) Crossdresser Fetish Guy Fucks Shemale cum in mouth chantage
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 7,588 Crossdresser Asian Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
50%
SISSY AWAKENING
- Trou de gloire du sex-shop - "Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleu... Read full Story
Femboy 2021 2023-02-17 1,406 Stockings Crossdresser Outdoor Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
50%
💞 VIERGE ⚧️ ⚧️
Avoir vingt et un ans la semaine prochaine et toujours vierge, est-ce vraiment si triste ? Pas une vierge sans baiser au moins, mais je ne sais pas si un baiser ivre avec une fille au hasard il y a quelques années lors d'une fête au hasard provoquée par la foule compte. Presque tout le monde a e... Read full Story
Femboy 2021 2023-03-23 744 Stockings Crossdresser Fetish Guy Fucks Shemale cum in mouth feminisation forcé
66%
Sex in the kitchen with my hubby's friend - a cop
Ever since my wedding last year, I enjoy a great time with my hubby who loves me so much and takes care of me so much. Since he is married and having another family, he doesn’t stay with me all the time, but comes and stays at least 2 or 3 days in a month and we literally celebrate those nights wit... Read full Story
Manusha Tranny 2021-10-14 5,429 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
83%
Did I Do Right By Taking Money For Sex?
I first properly dressed when 14. (I did do the knickers and stockings and pantyhose thing previously from when I was 11). I first had sexual contact with a friend when we were both 14, i.e. wanked each other then I sucked him off and drank all his cum. I then waited until I was 16 for sex with... Read full Story
Linda Tiffany Vista 2024-05-07 3,083 anal Blowjob blonde Lingerie shemale fucks shemale cum in mouth teen (18+)
100%
Becoming a Chrissy - Chapter 2
I had always felt like I had a hot body for a girl. I was naturally blonde and smooth; I guess I had been blessed by my parents’ Scandinavian genetics. My pubes were always just a small fuzz—easy to shave and keep a clean bikini line. Same thing with my armpit hair. And my ass? Completely smooth and... Read full Story
mindlessrobot45 2024-05-13 3,935 Crossdresser gangbang Shemale and Girl cum in mouth shemale fucks female teen (18+)
100%
PRIS AVEC DES CONSÉQUENCES ⚧️ ⚧️
Je m'appelle Stephen et je suis étudiant diplômé à l'école de commerce locale. Je suis à mon travail depuis moins d'un an et, en tant que nouveau venu au bureau, je pensais que faire des heures supplémentaires ferait bonne impression sur mon patron. Eh bien, j'ai certainement fait une impression, ma... Read full Story
Femboy 2021 2023-03-24 971 Stockings anal sex Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth feminisation forcé attrapé
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? I throw you squir... Read full Story
LulaSissy 2024-07-10 851 anal Stockings Crossdresser Cumshot Bareback Fetish Big Cock Ladyboy Lingerie femboy shemale fucks shemale cum in mouth shemale fucks female
100%
Shemale fantasy with female squirting
I just finished my mornig coffee at the breakfast bar in the kitchen when the door beel rung. My wife opened the doo and it was one of her hot friends. She invited her to sit at the bar beside me and serve her a coffee. Right before she gives her the coffe she slips something into the brew. Her ... Read full Story
TRTRAIN 2023-05-21 3,665 anal Stockings Amateur Big Tits Big Cock Lingerie Shemale and Girl pantyhose Mature Homemade Ass to Mouth cum in mouth shemale fucks female
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,850 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
60%
Shemale Chrissy Fucked by a Demon
I wanted to write this the night it happened, Halloween, but I was still so traumatized. I was at my fictional fantasy Sugar Daddy's house alone and already spooked out by the noises of this old hundred-year-old wooden house in this loud thunder storm on what some call "Devil's Night." I had to turn... Read full Story
Chrissy Tunnell 2022-12-01 4,232 Small Tits Crossdresser Amateur Bareback Fetish Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale cum in mouth
22%
Just me...
When I first started to get high, I was such a good freak. I started taking pictures of myself in panties and lingerie, taking pictures of my dick and showing the world, showing off my tight little asshole, just trying to become a porn star. I still want to be a porn star because I know that I would... Read full Story
AllOfMe 2018-06-01 3,954 Teen (18+) Ladyboy redhead Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
80%
Getting Fucked by Sasquatch
Bill was about to show up, I had known him from a chat room for years now. I was in his town for work and we had set up this date so we could finally meet each other. I heard a hard knock at the door and when I swung it open, I just stood there in awe. It wasn’t the big beard or really long hair tha... Read full Story
pennypenny 2020-08-21 6,090 Crossdresser Bareback Creampie Fetish Blowjob Big Cock redhead domination Guy Fucks Shemale pov Ass to Mouth cum in mouth
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 1,936 Crossdresser Amateur Group Sex threesome Big Cock Mature Homemade cum in mouth shemale + shemale milfs Foursome Bi
50%
Ado est forcé à poule mouillée
Ma première fois avec un autre homme était quand j'avais 18 ans à la fin des années 80. Ma copine était vierge et le plus loin nous sommes allés baiser et frotter avec nos vêtements. J'emmènerais mes magazines sales là où nous habitions dans les bois et enlèverais tous mes vêtements et me mastur... Read full Story
Femboy 2021 2023-01-27 778 Stockings Teen (18+) Crossdresser Fetish Blowjob Lingerie Shemale and Girl domination Sex Toys cum in mouth
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 1,082 Teen (18+) Crossdresser Fetish Futanari cum in mouth shemale + shemale
50%
DU VILAIN PETIT CANARD À LA PRINCESSE SISSY ⚧️ ⚧️
Être un mec très petit 1 mettre 60 avec une petite carrure a été un handicap majeur dans ma quête de compagnie féminine. Avoir un micro pénis était le clou de mon cercueil. Tout au long de ma jeunesse, j'ai été ignoré ou rejeté par les filles. J'ai eu ma première petite amie à l'unive... Read full Story
Femboy 2021 2023-03-23 955 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial cum in mouth shemale + shemale
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 4,151 Crossdresser Amateur Cumshot Masturbation Creampie Blowjob redhead domination Sex Toys Mature Homemade Ass to Mouth cum in mouth
50%
RÉVEIL SEXUEL SISSY ⚧️ ⚧️
Si ses histoires étaient vraies, non seulement beaucoup d'hommes ont eu des réveils sexuels entre la fin de la trentaine et le début de la cinquantaine, mais beaucoup d'hommes de mon âge étaient curieux de se féminiser, de sucer des bites et peut-être même d'avoir des fesses. Mais je ne peux pas ... Read full Story
Femboy 2021 2023-02-17 1,285 Stockings Crossdresser Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial Sex Toys cum in mouth
50%
UNE RELATION À DISTANCE ⚧️ ⚧️
Les relations à distance sont difficiles, surtout dans ces premiers mois très importants où vous passez chaque instant à parler, toucher, embrasser et baiser. Lorsqu'il s'agit d'une longue distance, 20 heures sur 24 sont généralement passées ensemble nus et au lit; le seul moment où les vêtements so... Read full Story
Femboy 2021 2023-02-21 746 Stockings Crossdresser Group Sex Fetish Blowjob Big Cock gangbang Lingerie domination Guy Fucks Shemale cum in mouth
50%
UN JEU DE HORSE ⚧️ ⚧️
Peter et moi étions amis depuis que nous jouions au basket ensemble au collège. J'étais le meneur nerveux et il a pris les rebonds. Aucun de nous ne pouvait tirer, mais nous pensions que nous étions Kyrie Irving et LeBron James et avions prévu de mener l'université au championnat d'État ... Read full Story
Femboy 2021 2023-03-21 969 Stockings Crossdresser Fetish Lingerie Guy Fucks Shemale cum in mouth
50%
Liberty meeting, chapter1
On a beautiful summer day, my phone rings. It's Steve, the boss of a transvestite company who calls me. - Hello Sandra, I have four new friends waiting for you at the club. - Thanks for thinking of me, I'll be right there, I said, hanging up. I am happy with his call because I always meet ... Read full Story
sandratvtg 2024-06-20 2,466 Stockings Shemale Fucks Guy Fetish Lingerie shemale + shemale
100%
Tom Didn't Get A Choice
Tom Didn’t Get A Choice This was Tom and I’s first date. We had met online, so he already knew that I was a very femme sissy crossdresser. Tom eventually asked me on a date. I happily said yes, knowing that I turned him on a great deal. On the evening of our date I wore a black dress that wa... Read full Story
pennypenny 2019-02-18 6,327 Crossdresser Cumshot Bareback Creampie Blowjob redhead Guy Fucks Shemale cum in mouth
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,312 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 7,411 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 12,309 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots
100%
Getting Fucked By Jeff
Getting Fucked By Jeff I was sitting at the bar one night having a drink and wanting some dick when a man sat next to me and said “Hi, I am Jeff.” Smiling at him, I said” Hi, I am Penny.” Jeff and I chatted and he bought me another drink. After a while, Jeff said” In all honesty, I only boug... Read full Story
pennypenny 2019-02-25 6,478 Crossdresser Amateur Cumshot Bareback Creampie Fetish Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth cum in mouth
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 4,109 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
45%
Threesome with random muslim men from Dubai -
As you all know, most of the meetings with my clients happen in good 3-star or 4-star hotels. Clients normally visit my hotel room and have fun. This exciting session happened during my stay in a 3-star hotel room in Bangalore on March 1st and 2nd. I had bookings for both the days and was prepare... Read full Story
Manusha Tranny 2021-10-14 9,128 Crossdresser Cumshot Outdoor threesome Blowjob Big Cock Asian Ladyboy gangbang domination Guy Fucks Shemale Ass to Mouth cum in mouth
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 1,237 Crossdresser Cumshot Shemale Fucks Guy Shemale and Girl Futanari cum in mouth
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... bien que j'adore bouffer la chatte et baiser ma femme. Certains appelleraient cela de la curiosité.... Read full Story
Femboy 2021 2023-02-21 1,150 Stockings Crossdresser Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial Sex Toys cum in mouth