Free Shemale Stories

Danielle's First Time

Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... read more

shemale lover February 3, 2012 100%

Shemale Seduction - The Surrender

I cannot remember what drove me to it. Cruising bars for sex had become a habit. Success can do that to you, but even steady success make you yearn for something different. I looked at her from across the bar and acknowledged her stare. She definitely looked hot and hungry, with eyes that seemed to ... read more

shemale lover February 3, 2012 100%

My first anal

This was a couple years ago, but I still remember it very well. I was insanely horny one night so i signed up for a sex dating/chat site. I'm siting around, rejecting chat invites from guys, thinking I'd never want a cock. After a while, I decided to try chatting up a guy, see what kind of stuff ... read more

shemale lover February 24, 2012 100%

Hose and Heels in School - I'm a bad girl

A knock on the door? Who could that be? After all it was mid-evening on a Friday night and I certainly wasn't expecting anyone. I was looking forward to a night of relaxing on the sofa and nothing more. I opened the door and there stood Liza, staring at me with a smile on her face. "U... read more

shemale lover May 11, 2012 100%

Olderman and mature crossdresser Part 2

We left the park and drove to his house which was very nice.I knew he was wealth when he picked up due to his car was new jag. He fixed me drink and we sat on his couch and kissed and made out an heavy petting.He kissed my neck driveing me nuts as he did I rubbed his cock thru his pants which was ha... read more

shemale lover May 26, 2012 100%

My first time with three shemales

This is a true story it happened to me back in 1988 when i was still bi i was in a local gay bar it was shemale night close to midnight when i saw this very tall gurl walk in with some friends she was hot about 6' 2" tall with 6" heels" all legs and ass she was blond and so senual wit... read more

shemale lover September 20, 2012 90%

When the Balls Drop; A New Years Tale Chapter 12

Chapter Twelve: The Show... "Mmm...God that was hot." Mason said. "I think someone needs to clean Candie up...it's your turn Mason..." Veronica instructed. Mason guided the dancer over to the bench and laid her down on in lengthwise. He rubbed his hands up the dancer's s... read more

shemale lover December 6, 2012 100%

Fun With Friends Chapter 4

As I stepped into the shower the warm water hit my body and felt great. I relaxed my ass and let Greg's cum stream down my leg. I could not believe that in the last couple of hours I had been shown to one of my best friends as a cross-dressing slut and had now taken his cum in both my ass and mo... read more

shemale lover December 12, 2012 100%

Liberty in Lisbon Part 3

After Olivia had so perfectly taken my anal virginity, we laid in bed cuddling, touching, kissing and her cum leaking from me. I had not been so lovingly caressed for such a long time. It was just perfect. She asked me how I was feeling. I think I said before that I don’t do deep and meaningful very... read more

Rusty12 September 16, 2020 100%

Passion in the Rough

Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... read more

Regina10 April 27, 2024 75%

It's a cold, windy, and snowy evening

Another work of art of a shemale lover. Props for this wonderful romantic story go to our forum member Ila. It's a cold, windy, and snowy evening. My lady and I are in the bathtub together. The water is still very warm and the scent of bubble bath still lingers in the air. I have just bathed her ... read more

shemale lover April 21, 2015 50%

Shemale Autofellatio Adventure

Hi, my name is Jessica. I'm a 19 year old Caucasian girl with a 6" surprise between my legs. Most of my friends don't know about me but I've got a few who do and one likes to fuck just as much as I do. I was bored one day browsing porn on my computer when I came across a video of a guy sucki... read more

shemale lover September 18, 2011 91%

Helping a Friend Part 2

I had seen Anna at work for the past two weeks…not a word of what happened at her house, when I fixed her sink. What a great night that was……………the night I found out she was a shemale! I fantasized about Anna all the time, yet nothing from her. It was our s... read more

shemale lover October 2, 2011 100%

My first time with a shemale

My girlfriend had been out of town for a couple of weeks and i was so horny and wanted to get upto something kinky. I called a shemale site from la costa del sol called taiakshemales and arrange to meet one of the beauties. I was very nervous as i drove to her house as i never touched a dick befor... read more

shemale lover November 7, 2011 87%

The Walking Dead

My name is Ivy. That's not my real name, but that's another story. I'm 20 years old and this is my journal. There was an apocalypse and most of the civilization fell victim to this terrible disease. I was one of those who were punished by surviving. For a long time I though I'm the only survivor... ... read more

shemale lover November 21, 2011 75%

Superstar fun - an evening to remember!

Starting with a little history, let me say that I started getting into tranny fun back around 1990. I went on a visit to New York and had always been an avid reader of Screw magazine/ newspaper. Before the Internet was in full-bloom it was distributed nationally to all cities around the country and ... read more

shemale lover April 3, 2012 33%

Be Careful in the Park

One was jet black; he looked the oldest, wearing white rugby style shorts and a black T. The youngest looking was also coloured, more a coffee colour, in his case wearing denim shorts and a polo shirt. The others were white but standing more in the shadow so I couldn't make them out so clearly at th... read more

shemale lover May 3, 2012 60%

The Boy is A Girl Now

When I turned 16, I decided to go to a gay bar to see what the deal was. I had not been with anyone ever but I was curious and very much feminine. I stole my older brothers ID and caught the Bus to go to the Ballgame, so I told my mom. Then I wound up at the gay bar just as they opened that night at... read more

shemale lover May 9, 2012 100%

Double penetration in Vegas

On a trip to Los Vegas for my Birthday we had a great time. Same old shit, we won and lost, saw all the sites and a few shows. The last night we were there however we were BORED…. That being said and knowing US, We took a stroll around the hotel. Maxx was checking out all the hot women in the... read more

shemale lover May 31, 2012 100%

A Sticky Situation

My boyfriend, Scott, has gotten himself into quite a predicament, and I don't know whether he even knows yet, but he will before too long. He's been throwing up for weeks now and seems to be able to eat only white bread, which he normally hates, and potatoes. He's also tired most of the time and has... read more

shemale lover June 30, 2012 100%