Free Shemale Stories

Gay Cumslut

I was busy at work and Robert a guy I work with needed a little help. I told him to come into the lab and I locked the door behind us as I wanted to get some work done undisturbed and then go home. I leaned over one of the computers that I had been working on most of the day. And after a couple of m... read more

MARKUS6969 April 23, 2018 85%

Gay Roommate crossdress

I have been cross-dressing since I was 7, always been a bit in the closet about my homosexuality and cross-dressing but I have always loved it and kept it close. I had one roommate when I was living in Boston his name was James. he was a pretty good looking guy who seemed to always be doing well ... read more

bigtranslover December 15, 2013 91%

Lara 3 : πούστεψα!!

Lara 3 από κωλογαμιάς γίνομαι πούστης!!! 2 Αυγούστου 1991, 4.30μμ στον Αρίωνα: Παρτούζα με τέσσερεις πούστηδες Είχα διόμιση μήνες να πάω σε τσοντάδικο... κι η μέρα ξεκίνησε με τέτοιον τρόπο που μ’ ενεργοποίησε... Ήταν η τελευταία μέρα δουλειάς[1]... Όλη τη μέρα είχα στο μυαλό μου να πάω να γλε... read more

hotmatureLara October 19, 2021 50%

Gay chat

About 4 or 5 years ago I was a member in a free gay chatroom. I would go in every three or more nights (sometimes more) when my wife was at work. I loved to help guys get off while showing my hard cock for them. I would do all kinds of things, like telling them how I would suck their cock or lick a... read more

shemale lover August 15, 2011 100%

The Fuck that would never end

This is a short story k? I went to Italy to visit my cousin Lance and he showed me around and some of the guys hit on me but when the day was over i layed on the couch and fell asleep... about 3 hours later... I woke up on a stool tied up and saw my cousin nude infront of me with a HUGE COCK! and... read more

shemale lover September 12, 2011 100%

My first gay fuck

I've always crossdressed, from when I was 12 years old. I started by wearing my Mum's knickers and bra, tights, knee high boots and a dress or skirt and top. it felt fantastic wlaking around on high heels, in the back garden, knowing that all the neighbours had to do was look over the fence and see ... read more

shemale lover July 22, 2012 78%

Crossdress fuck

One day while at university I went to the toilet. There was some one in the next cubicle. I could see a shadow under the partition. It was moving back and fort very fast. Was he wanking? I started to feel horny thinking about it. As a cross-dresser i was wearing a satin night-dress under my clothes.... read more

shemale lover April 21, 2014 90%

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%

Don't "DRAG" It Out Of Me...

I was a Service Brat; living near FT. Hood Tx. at the time, and had just turned 14. My friend Peter was a little more than a year older than I, and we had started getting each other off with hand jobs but nothing else during the previous summer. One day after we'd finished swimming, he asked if ... read more

DJFreak201 November 22, 2012 100%

Sissy Amante de la Lencería

HOMBRE AMANTE DE LA LENCERÍA marinatvfem@yahoo.es Tengo 60 años y estoy casado. Llevo muchos años usando ropa interior femenina. Me encanta la sensación del nylon sedoso en mi cuerpo. También duermo con un largo camisón de satén todas las noches. Me siento muy cómodo llevando mi lencería femenin... read more

Marinatvfem April 1, 2019 50%

She was a he

I was recently divorced, 39 years of age and living in an apartment in Sydney's inner eastern suburbs not far from the famous red light district of Kings Cross. After two failed marriages, I was footloose and fiance free and as lusty as a rampant bull on speed. I chased after anything wearin... read more

shemale lover January 24, 2012 94%

MY First Time with a non-binary/cross-dresser

After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... read more

ghostpeople March 12, 2019 100%

Horny Writing A Strange Habit

I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... read more

Araina March 8, 2021 100%

Groped on the Bus

In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... read more

Chrissy Tunnell March 17, 2023 100%

Groped on the Bus!

In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... read more

Chrissy Tunnell March 22, 2023 100%

Lola - chapter one

This is a fantasy but with a lot of inspiration from real life experience. More chapters to follow. Chapter 1 So now I knew, without a shadow of a doubt, what it was that caused this familiar smell in my house - and where it came from. When I got back home my laptop was lying open on the kitc... read more

BellaBeau October 5, 2023 92%

I fucked my personal trainers ass for the first time

I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... read more

Madison Heights May 18, 2023 100%

A man & Two Hung Shemales meet in Art Gallery o

I spent a week of absolute extreme erotic ecstasy with Stan. I used his throat and ass multiple times a day. He also fucked and fisted my ass as well. It is a week of total decadence debauchery and depravity. In the late afternoon, Stan and I decide to visit a local art exhibit so we can get out ... read more

darrell February 2, 2024 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%

A Perfect Life

The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... read more

shemale lover May 5, 2012 50%