Free Shemale Stories

MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... read more

shemale lover December 1, 2013 88%

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 more

Stud4Shemale February 20, 2021 33%

Making Love Vs. Fucking

We all know the difference between making love and fucking, but for those that may not here is my take on the subject. When my partner makes love to me it is slow, gentle, sensual....he does it not only to make himself feel good, but to satisfy me as well. Making love is selfless and sacrificia... read more

Chrissy Tunnell January 28, 2022 100%

Shemale sex on a beach

Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... read more

xanykeyx May 7, 2020 100%

Shemale sex on a beach

Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... read more

xanykeyx May 7, 2020 92%

Male or Shemale, Still a Slut

Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... read more

shemale lover December 20, 2012 100%

My first date with a "shemale"

I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... read more

bmogotti March 9, 2020 41%

Experience with Shemale Kadambari in Pune

PS: this is a genuine experience. Hey, I am back with another story. Let me introduce myself. I am ordinary guy who like to score shemale from Pune. I have already posted one experience with arzoo. So yes let's start, I had a normal chat with Kadambari on what's app discussing the rates. So she a... read more

spidymoto March 24, 2020 54%

Big cock shemale from Pune, India

I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... read more

Stud4Shemale May 22, 2017 56%

The Guy At The Pool

The Guy At The Pool Stepping out of my hotel room for a smoke I saw two young guys at the swimming pool which my room overlooked. One of them was standing outside the pool speaking to the other guy who was in the pool. The guy beside the pool immediately caught my attention, his shirtless bo... read more

pennypenny October 21, 2019 76%

CD/TS Shemale Chrissy Fucked On the Ranch

I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... read more

Chrissy Tunnell March 4, 2022 100%

The New Housemate's Secret

https://chyoa.com/chapter/Introduction.150836 The New Housemate's Secret How will you discover the hot new tenant's secret? Chapter 1 by Bauer1 The doorbell rings, a soft knocking accompanies the bell to break the silence of the house. You look up from your laptop nestled snuggly in your la... read more

Acche April 4, 2019 91%

Dame et jardinier

Piotr se tenait sur les escaliers de la villa de Klonowa Street, située dans le quartier à la mode et riche de sa ville. Il était environ midi par un chaud samedi de juin. C'était son dernier arrêt ce jour-là. Il avait déjà collecté l'argent des autres clients avec lesquels il traitait des jardins, ... read more

Femboy 2021 January 24, 2023 50%

My first night was making love to a man

First .... My name is Lely Bella Calistia, of course it's the name when I decided to become Shemale. My age is now 28th, I became a shemale when I was 24th, when I first chose to be a shemale because I was obsessed with my ex girlfriend, after parting ,, .. maybe because I really miss her an... read more

Bella Calis March 13, 2018 75%

Florida TG Experience

I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... read more

Jon Paul August 13, 2018 100%

He Could Have R*ped Me!

This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... read more

Chrissy Tunnell February 2, 2022 100%

SOUS LA DIRECTION DE MAMAN

Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... read more

Femboy 2021 January 26, 2023 50%

A LA DÉCOUVERTE DE L'AMBRE ⚧️

J'ai toujours aimé la lingerie féminine. De regarder des catalogues à voir des copines le porter, j'ai adoré le look et la sensation de la lingerie sexy et soyeuse, mais pour moi, cela a toujours été plus profond. À 18 ans, j'ai essayé ma première paire de culottes, oh mon Dieu, c'était merveilleux ... read more

Femboy 2021 February 17, 2023 50%

Hard Decisions by Elaine © 2020

Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... read more

Elainetguk September 6, 2023 50%

I’m not Proud to say it, but I fuced “Mac” in the Ass!

Yes, I Fucked Mack in the Ass and I’m not proud of telling this story. Even to this day I regret fucking him, but it felt so dammed good. My relationship with Mack started out with a blowjob, this homosexual motherfucker was good at what he did. I’m innocent, I’m green, not knowing that getting my d... read more

lkusex May 28, 2021 100%