Free Shemale Stories

Dressing Up For My Wife

My wife and I had a bet on the football game that pitted our two rival teams against each other. It was a horrendous day for my team and hers slaughtered mine 31-0. It was the same bet we always have with each other. It is a bet where no one really loses because it ends up with us having wild kinky ... read more

shemale lover November 29, 2012 100%

Friendly Neighborhood

"Oh my God Katie, your ass is so fucking hot" I hear as the cock slides in and out of me. "Yeah baby, suck my cock" comes from the guy standing in front of me with his dick in my mouth. I'm on my knees with a cock in my ass and one in my mouth. These cocks belong to my neig... read more

shemale lover November 29, 2012 100%

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%

Fun With Friends Chapter 6

The following week flew by and I visited Becca and Greg's twice, each time presenting myself at their door in sky high heels and a slutty outfit. Each time having let the two of them use my body as a fuck toy for mine and their pleasure. I knew that I wasn't gay as when I saw men I didn't wonder ... read more

shemale lover December 12, 2012 100%

Fun With Friends Chapter 7

After filling Kyle's mouth with cum his humiliation continued that night with the girls picking out a sexy little outfit for him to wear before Hannah & Steph took it in turns to fuck him with a huge rubber cock as we all watched on. At first he was a little unsure trying to walk in the 5" ... read more

shemale lover December 12, 2012 100%

Anna's Panties

I am a 32 year old guy living in the UK and married to Anna (25) for two years. I have never had sex with another guy but recently I have been thinking about it more and more and the thought is really driving me wild. My recent experiences have taught me that I am definitely ready to explore my bise... read more

shemale lover December 12, 2012 100%

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%

The Meeting

He could not believe that he was finally going to see her after all these years. Since his divorce, she had been all he could think of. He fantasized every day how it would be to see her again, make love to her again, and now the day had finally arrived. He could barely sit still. He had decided... read more

shemale lover December 21, 2012 100%

Cheri's Ordeal

Cheri knew that she had made an error in not following Ken's instructions. She felt that she would be able to do as she pleased while at home alone. That, of course, included the right to masturbate at any time. After all, she had been beating off several times a day since her early teens. To be ord... read more

shemale lover January 11, 2013 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%

Boi Toy

They met me off the train late in the afternoon. Their welcome was warm and friendly. I was exhausted from travelling and spent the evening in wonder as we first had drinks with friends of theirs at one home then all went out to eat at a restaurant, then back to another friends home for more drinks.... read more

shemale lover January 29, 2013 100%

Steve to Stephanie Chapter 1

This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve... read more

shemale lover January 29, 2013 100%

Dottie's Back Chapter 2

After tossing my purse onto the kitchen counter, I nearly ran across the backyard toward Kim's house. Stopping a few feet short of the fence, I kicked my heels over it, pausing to be sure they landed in Kim's yard. On a previous occasion, one of my heels flew into the yard next to Kim's. This forced... read more

shemale lover January 29, 2013 100%

CD And Trucker

At least four things went through my mind the moment I heard Hank ask me to go along with him. - One my wife was gone for at least 2 weeks so that was no problem. - Two, with wireless connection and my laptop I could take my job on the road. - Three, I had hardly any clothes in my bag that I was ... read more

shemale lover April 30, 2013 100%

A Job In The Theatre

Chapter 20 -- Gary becomes Gayla "Be a dear and get that bag from the car," Paula winked. "Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of ... read more

shemale lover April 30, 2013 100%

Fitting Room Fantasy

Being a 'girl of a certain kind', I always use the women's fitting rooms in stores when I am out trying and buying clothes. I tend to avoid the 'communal' type, where we are all stripping off together, as I'm quite shy and you also never know if someone may pick up on the fact that not everything ab... read more

shemale lover June 4, 2013 100%

Allison the pool slut part 1

Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to... read more

shemale lover June 5, 2013 100%

Finding master

It had been my dream all along to be someone’s sissy slave. To be able to please them time and time again. I met my master in a gay club that had cross dressing night. I was of course dressed in a dress with stocking and stilettos. Master was in leather pants and a tight tee shirt with his mus... read more

shemale lover July 16, 2013 100%

Good Friends are the Best

This story takes place after I had been crossdressing and watching shemale porn for years. It all started out with me trying to avoid seeing men's cocks while watching porn so I tried lesbian porn and then found shemale fucking girls porn to be crazy sexy. After watching a lot of shemales fuck... read more

Jinn.V23 January 20, 2014 100%

Slutty Sissy's Naughty Weekend Part 1

I'm bi and it started when I was about 15, just wearing my GFs knickers, thongs and bras. The excitement of it, the feeling of the flimsy material barely covering me. I kept this up for 3 years until recently id been talking to a guy online who called himself seb, a guy who described himself as 'Tal... read more

shemale lover September 15, 2014 100%