Free Shemale Stories

Ladyboy Switch Story

I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... read more

shemale lover February 27, 2015 81%

My First Ladyboy

I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers. This particular Friday we were in the usual place chatting and having a nice relaxing time. When she walked in. Taller t... read more

shemale lover August 9, 2013 91%

My Futanari Dreamgirl

My Futanari Dreamgirl I opened the door and there it was, just swinging between her legs. Big and veiny with a bright pink head. My roommate Jesse didn't notice me walk into the bathroom. She had just stepped out of the shower and was toweling off her hair. Her eyes were covered by the towel... read more

Jade Dixxon October 23, 2017 78%

Beautiful ladyboy Natalie

Feasting comes after fasting. What's with you guys, it's been over a month that i haven't seen any new shemale stories from you, and now i'm getting them every day. Which is good of course. ;) Here's a shemale story from Tommy about his long-standing shemale fantasy finally fulfilled. I'd had she... read more

shemale lover May 3, 2015 80%

Ladyboy Loves Up The Midwest

When Jasmine, a Thai ladyboy, moved into a small town in Iowa the locals didn't know what had hit them. She was instantly the talk of the town; initially for being so different and exotic but once she opened her club her reputation spread right across the county and state line. It was only a real... read more

shemale lover October 8, 2011 80%

Fucked and sucked by a ladyboy

Our reader Maxie wants to share what it is like to be fucked up bottom by a ladyboy and getting a blowjob from her at the same time. Seems very exciting, what do you think? ;) On a recent visit to Thailand I went further than I ever thought I would. I picked up a "young lady" Bangkok wh... read more

shemale lover February 9, 2015 79%

Fucked by indonesian ladyboys

this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... read more

shemale lover September 17, 2014 85%

Bangkok Bar Girl

I recently attended an international trade conference in Bangkok. The manager of our small office there, a big, ruddy-faced 50-something American called Mac, took me under his wing. (I'm 32 by the way, and married.) Before I left for the conference my colleagues in London wound me up mightily about ... read more

shemale lover February 11, 2012 100%

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%

Becoming Alanna Part 2

Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... read more

shemale lover July 12, 2012 80%

First time with a cute ladyboy

It had been a long week at work. So I decided to go to the Sound Factory for a drink and maybe get lucky with the ladies. As soon as I got to the bar, I spotted a beautiful asian lady wearing leggings with pantyhose and a sexy little top. She offered to buy me a drink, who am I to refuse. So we had... read more

shemale lover May 7, 2013 100%

I and the old man's story 后面中文

I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... read more

Oldslut Sissy April 15, 2024 50%

Becoming addicted to her she-cock

"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... read more

Curious_billy May 7, 2023 100%

The reason why I became a crossdresser

At first, I was just a straight and ordinary boy who was into sexy lingerie, stockings and heels. But one day, I suddenly thought that I wanted to try on my mom's panties, stockings, and high heels. So I did it. It was so excited and I started to get addicted to cross-dressing. Before dres... read more

cdmisato February 28, 2024 100%

Chicago TG Romance (part 3)

It is Sunday morning, just barely dawn and I have just spent the weekend with the most amazing girl. You know when everything clicks and it seems that at first you have met the person you want to spend time with and share with. Beth was standing at the glass windows full length and the sun was just ... read more

Jon Paul June 4, 2018 77%

Shawshank affair

Courtrooms can be a scary place. They smell like older leather, the wood paneling has been polished with oil and each sound penetrates your body like a loud smack from a cap pistol, which echoes in the forest, especially the gavel smacking on a block from the Judge. I felt strongly that I would be f... read more

Jon Paul August 20, 2018 100%

Car Broke Down

A Fantasy: Car Broke Down My car was running hot so I pulled into a driveway so that it would cool down. I got out and raised the hood and added some water. I then got back inside and smoked a cigarette and sipped on a beer that I had. I listened to the radio and glanced out the window and... read more

iluvgurls November 14, 2018 61%

delicious virile male flesh

Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... read more

hippocampus_171 April 23, 2023 100%

mushrooms in all shapes and forms

Mushroom season is open! Yummy! I love mushrooms, in all shapes and forms. We were about fifteen mushroom lovers who only get together to pick mushrooms, without any other friendly gatherings! For this last outing of the season, our splendid instructor was accompanied by her cousin, who was sup... read more

hippocampus_171 November 24, 2023 100%

First Time With A Dominant

I had long been interested in BDSM, specifically female domination. After downloading a shemale dominatrix video by mistake, I became interested in a dominant shemale. I consulted the internet looking for something, and when my wife was away for the week for business, I finally decided to go ahead a... read more

shemale lover September 23, 2011 85%