Free Shemale Stories

Halloween Double Cross

It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeou... read more

ASSEaster5678 October 29, 2018 82%

Masturbation fantasies: Amanda, queen of the peep show

A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... read more

ThatEroticWriter July 24, 2019 91%

Masturbation Quiz

Basics: Are you male or female? male Age? 35 At what age did you start masturbating? I think around 11 years old How many times a week do you masturbate? nearly every day How many times do you orgasm each time you play with yourself? one Where do you masturbate: In bed? rarely In the showe... read more

Betas84 January 27, 2020 100%

Masturbation fantasies 2: Looking for Amanda

Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... read more

ThatEroticWriter July 24, 2019 100%

Unconditional Love Chapter 8

After a two' hour nap, Alison and I awoke and the first thing we did was make our way to the bathroom to freshen up. I started up the hot water and climbed into the shower and' once she finished relieving her bladder Allie climbed in with me under the hot water and we embraced each other. We kiss... read more

shemale lover February 4, 2013 100%

Halloween Disguise

an original story by me. its not true more of a fantasy... this story starts october 14th. first of all i am a 23 year old boy, i just moved to a different state to go to college, i dont have many friends and have only been her a couple of months. today was like any other day, had to wake up e... read more

shemale lover August 7, 2011 44%

Lady Regina

I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... read more

Regina10 July 1, 2022 50%

LA CRÉATION DE MONICA ⚧️ ⚧️

Je savais. En regardant en arrière maintenant, je me rends compte que j'ai toujours su. Je n'ai jamais rien fait à ce sujet, jusqu'à ce que je sois prêt mentalement, émotionnellement et physiquement. Je suis né Matthew J. Smith au milieu des années 70 en Amérique centrale aux États-Unis. J'ai grandi... read more

Femboy 2021 March 30, 2023 50%

Wild halloween night

First sorry everyone it’s been a several month since I been here was busy with my life. Anyway Halloween comes once a year and we all wear custom and I know personally lots of guys like to wear female custom. I am cross-dress and love Halloween, this Halloween was wild first ever wild Hallow... read more

shemale lover September 21, 2014 78%

Billy Is Billie on Halloween

It was October 30th when I first found out who I really was, a cock sucking cum drinking whore that needed to be fucked. For so long I have dreamed of women without having any luck actually being with them. With my very feminine figure and shoulder length hair I was always pushed aside for the bigge... read more

shemale lover June 13, 2012 100%

Fun Times at Halloween

It was almost Halloween and I was stumped for a costume. I was excited, tonight was the annual Delta Kappa Halloween Bash, the biggest fraternity party of the year. All the Greeks got dressed up for this party, even those not in DK. I headed down to my friend Kathy's room to see if she could help... read more

shemale lover December 8, 2012 100%

Happy Halloween

Hello my name is Mike! Let me tell you a little about myself for the story. I'm about 5 foot 5 and thin, about 135bls. I am half white and half hispanic, so i have a nice light brown complextion. I don't have much body hair and am very GAY! I have always know that I was gay, there was never... read more

shemale lover January 11, 2012 71%

One Great Halloween

I was 18 and I was alone at home for the last week of October and the first week of November. I had dressed up in women's clothes before, just sitting around the house with nothing else to do. So when my friend George called me Halloween day to invite me to a Halloween party, I said id go with him s... read more

shemale lover September 2, 2012 71%

Fun Times at Halloween Part 2

It was the following Monday and I got a call from Kathy to come over to her room. After class, I headed over there and she let me know that she ran into Red. He said he had a great time at the party and wanted to take me out sometime. I was both excited and very nervous because even though I had suc... read more

shemale lover December 8, 2012 100%

Halloween with Movie Stars Chapter 4

Pete and Tim...first time without the girls There was a knock on the door. Pete knew it was Tim. They saw each other earlier at class and decided to get together after school. "Hey Suck Buddy," he said with a crooked grin. "Come on in." Tim returned the smile as he walked ... read more

shemale lover January 29, 2013 100%

Halloween Surprise, Pt 1

It’s been a while since this happened but I remember it like it was yesterday. I had just turned 17a few days before my favorite holiday. I’m a good looking guy, 5’6” maybe 140 lbs. Not the biggest guy in HS but not the smallest either. I have what I call camouflage colored eyes. Sometimes thei... read more

spencer_320 December 8, 2013 93%

A Halloween Hoodie story

This is the story of my first time going out dressed; it was halloween last year (2009). I figured i'd have less to worry about walking around dressed in a gothic tartan corset, spider-web mini-skirt, fencenet tights and about 10 armbands and bangles. It wasn't exactly brilliant but it was the excit... read more

shemale lover September 29, 2014 90%

A Halloween to Remember

Saturday morning I woke up feeling strangely euphoric. I remember thinking about it for a moment, and then realizing: it was Halloween. Cheryl and I had been invited to a party! The next morning (and for many, many mornings thereafter), I would remember that Saturday as one of the epic erotic encoun... read more

shemale lover March 8, 2012 100%

Working for Halloween

I stepped off the bus and walked the short distance to the 'Costumes and More!' shop. I couldn't believe I had agreed to do this, but if I was ever going to buy a car, I needed to get the money. You've probably seen them, this particular costume shop always has someone in costume out in front holdin... read more

shemale lover October 2, 2012 100%

Halloween with Movie Stars Chapter 1

It was Halloween weekend, which is absolutely the best weekend on campus. All the fraternity and sorority houses throw big parties. And since they are within a block of each other, you could go to one party after another. My costume was the classic white suit John Travolta wore in Saturday Nigh... read more

shemale lover January 4, 2013 100%