Free Shemale Stories

Working the Glory Hole

After so many nights of torrid fantasies plaguing my sleep, I took a long look at myself in the mirror. I had been slowly embracing my femininity over the past few months. My hair had grown past my shoulders, I was shaving my entire body on the regular, and I would wear panties under my guy clothes ... read more

KaceyKlarissa April 15, 2024 100%

Glory Hole Orgy

Driving down the street I spied my destination. A big yellow building with “Adult XXX” written on the marquee in front was on my right. I turn into the parking lot and drove to the back behind the building and park in the darkest spot I could find. Another crossdresser had told me that t... read more

shemale lover November 20, 2011 88%

Growing up CD Part 2

After we left Max, Peter and I fought over who would get to take the magazine home. We decided to tear out some pages so we could have some each. We agreed to catch up the next day and go to his house as his parent were going away for the week. That night after dinner I told mum (dad had left ... read more

shemale lover December 10, 2011 50%

Dance Bar Bathroom Slut

Dressed in extremely short cut off blue jeans shorts that showed my ass cheeks, 4-inch red heels, a red tank top, a sports bra, way too much make up and a blonde wig, I set off for Atlanta. "Black guys love trashy blondes don't they?" I thought to myself. I checked into an Atlanta hotel... read more

shemale lover June 6, 2012 66%

A Glory Hole for Tranny G

I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each ... read more

shemale lover March 7, 2012 85%

Glory Hole Whore

I’m a Glory Hole Whore. It started with a trip to a nature reserve, just north of town. I stopped at a large public campsite, to use the bathroom. It was between seasons and I was surprised how large the building was. It had four toilet stalls, two urinals and two sinks, on one side and two shower ... read more

Topazsteve February 11, 2020 77%

How I became a Transexual

I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... read more

shemale lover April 15, 2012 100%

Glory Hole Girlfriend

My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... read more

shemale lover December 18, 2011 71%

The glory hole of shemales

I walked in to a adult book store where I was heading for the glory hole in the back I have been there be for and know its safe.. I walked to the tooth I normally take and found it locked and some one was in there. So I walked to the one that had the x on the door wonder why did not hit me yet. I cl... read more

shemale lover April 15, 2012 80%

Glory Hole Memories

The Glory Hole Fun Begins Locking the car I look towards the building. The entrance is open, but from my position it isn’t possible to see inside, the bright sunshine making the entrance look black. My heels click on the tarmac as I approach, my legs beginning to tremble with fear and excitement.... read more

Sexy Michelle March 13, 2024 100%

First time out of the closet

I had always been more than a little interested in the world of cross dresser and she males. Since I was a teenager I had experimented with cross dressing. Usually just small stuff. As the years progressed whenever I was out of town on a business trip I would sometimes dress up in my hotel room. I a... read more

shemale lover April 19, 2012 100%

Trans Bookstore Adventure

I was walking near the corner of Polk and Post Streets past an adult bookstore when I noticed an attractive transgender standing on the corner. I walked up and struck up a conversation. I told her she was attractive. She asked me if I wanted a date. I asked her if she was functional. Then I asked he... read more

shemale lover August 11, 2011 94%

Glory hole surprise

I walked into the bookstore paid my way and went into the peeps; I usually avoid the theatres since there is not any privacy for playing. I guided my way in the dark letting my eyes adjust in the dark. I walked to the back where the stalls with the gloryholes are and found an open booth. I sa... read more

Quib January 23, 2017 76%

Trans Daughter F*cks Daddy

This is true story. I am 50 age n avid shemale , Transgender, ladyboy lover. Two years back i was member of LGBTQIA community in Pune where i met this ladyboy trans girl . We spoke, chat sone time and immediately clicked. She said she lost her father and wanna me to be her daddy. I agreed and i ac... read more

Stud4Shemale September 28, 2023 83%

My wife made me a bi-sexual

One night me and the wife were out drinking at a lounge on Maine Street it was getting late so we headed back to the car. As we were walking down the street, we walked by this adult bookstore called A-1 Adult Books joking around I said we should go in and look around (They had sex toys, books, and m... read more

JamieLeeCD April 27, 2016 82%

Sweet Encore

I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... read more

Regina10 May 9, 2024 100%

Camming down the rabbit hole Ch1

Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... read more

Dani_does_Dallas August 11, 2021 100%

Camming Down the Rabbit Hole Ch. 12

We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... read more

Dani_does_Dallas May 9, 2022 100%

Anastasia's Life So Far

Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... read more

shemale lover November 27, 2012 100%

Camming Down the Rabbit Hole Ch. 10

As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... read more

Dani_does_Dallas April 12, 2022 100%