Tranny/Shemale

57 Free Gay Erotic Stories in Tranny/Shemale

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Die etwas andere Geschäftsreise

by sweetStudent86

diese Story ist natürlich reine Fantasie. Ich hoffe trotzdem, dass sie euch gefällt. Falls ja kommen natürlich Fortsetzungen :) Ach ja und für die, die die Kategorien nicht lesen, das ist eine Story mit und über einen jungen Crossdresser und einem älteren Mann :)----------------------------------------------------------------------------------------------------Da stand ich nun vorm...

Gay Erotic Story

My Fantasy

by nudedon66

I just started college at age 19. One Friday night I stayed over my grandpa’s house and he told me that a man is coming over tonight to offer me a chance to become a shemale. He said he will come at midnight in the bedroom. Well I fell asleep as I slept on the couch in the living room where it was cool that summer night. He woke me up and said the man is here waiting for me. So I got out of bed...

Gay Erotic Story

A More Than Pleasant Surprise

by eroticbi

A true story by Johnny Fox email: foxybiguy4u@hotmail.comA MORE THAN A PLEASANT SURPRISEA true storyI 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 fiancé free and as lusty as a rampant bull on speed. I chased...

Gay Erotic Story

Mama puts me out; Chapter 1

by thongcladtommi

I had just turned 18 and graduated high school. My Mama and I lived alone, on the wrong side of town. She told me it was time to earn my keep; and she'd found a job for me. Good pay; easy hours; and time to go to Community College.Sounds good to me Mama. When do I start?You have an interview in 2 hours so take a shower while I lay out your clothes.I did as instructed; and went...

Gay Erotic Story

Saturday afternoon at the mall

by nounour

I am drinking a coffee at the local mall when my eyes spy her walking by. Simple skirt cut just above the knees, black stockings, 3/4 length coat hiding everything else...but for her darker hair and the fact that her walk is stiff...like her shoes are too small. Something always get my radar going when I see a transvestite. The coffee is what I need...but my focus is drifting to the...

Gay Erotic Story

Aus Tobi wird Mia (1)

by sweetStudent86

Da stand ich nun vor seinem Haus und merkte wie ich vor Aufregung etwas zitterte. Die ganze Fahrt über wechselten sich Vorfreude und Unsicherheit ab, schließlich kannte ich den Mann gar nicht, bei dem ich nun eine Woche bleiben wollte und endlich meine Vorlieben und Fantasien ausleben wollte.Einige Wochen war es nun her, dass ich Klaus im Internet kennengelernt hatte und schnell hatte...

Gay Erotic Story

A sexy gurl down the hall

by nounour

Note: Early Sunday morning...not much to do, lets write a story.Enjoy.Must have been two weekends ago that I first noticed her. Got home very late that night and found her waiting for the elevator. Did not check her out too much but did notice that her miniskirt let lots of legs showing. The door opened and we both got in. She pressed my floor and this got me looking at her a little...

Gay Erotic Story

Pimped Out, Part 3

by thongcladtommi

It had been 6 months since I entered my Master's stable. In that time, my hair had grown into a full shag and been styled. My body hair was non-existent with the exception of a small bush which was trimmed. Mama Jean had taught me to apply make up; and she administered my weekly hormone shots.The shots were intended to increase my breast size while reducing my body hair growth and...

Gay Erotic Story

You meet interesting people in a porn theater

by cleanshaven

I spend a lot of time in adult theaters and I’m always amazed at the quirky, unusual people I see there. At first, everyone seems pretty average, but as the dynamics of the situation evolve, you find that people have extraordinary tendencies.Take for instance the friendly coed and her studly boyfriend:This guy came in the theater with his pretty girlfriend. They looked just like a young...

Gay Erotic Story

Welcome to the Circle

by cleanshaven

I have masturbated since I was ten years old, but I‘ve always had to do it in secret because I was taught that it was a shameful act. It was first referred to in the Bible (Genesis 38:9) where it was called “Onanism” and it was considered a sin in those days because the act wasted semen instead of using it for reproduction. Well at the age of ten, I didn’t even know who Onan was or why he was put...

Gay Erotic Story

X wife catches me

by xzibit

my x wife and daughter were kicked out of their house and needed a place to stay....

Gay Erotic Story

2nd night with robert

by xzibit

I had the craziest night my first night as a girl robert was so cool he woke me in the morning eat my pussy.he was cleaning me real well.He was naked and had a nice body for his age.His cock was so hard a solid fat 10 inches.I started making alot of noise and he was driving me crazy .He would fuck me then he would eat me then fuck me some more.He was so fucking hard in my ass. we got lost fucking...

Gay Erotic Story

Fantasy come true

by xzibit

I had met a man on a gay chat line one night,his name was robert.He was a professional man that lived in hollywood.I was a closet transvestite and he liked that .He liked a strong man in nasty sexy lingerie and he loved nasty high heels.The first night on the phone he really made me feel like the girl i had always wanted to be. He was funny and we both loved nasty sex talk.I started calling him...

Gay Erotic Story

Beach party

by flyingfox121

Three years ago on a family holiday to Malaysia, a country we had visited before, we were staying in a beautiful resort on the island of Penang. well one particularily hot night I found myself unable to sleep, everyone else was well away, and after 2 hours tossing and turning, i decided to go for a walk, and some air. I quietly dressed in just shorts, and a teeshirt, and let myself out. I...

Gay Erotic Story

The Coming Out Party

by MissingHector

20 years had passed since my last sexual experience with a man. I have always been fascinated with transgenderism ever since I was a child. Over the years, I have always looked forward to the weekends when my wife goes to her mother's for some girl time. Typically, I will get all dressed up in a black lace teddy, stockings, and high heels with my brunette wig. I then will lay the entire bathroom...

Gay Erotic Story

Sissy Gets A Black Master

by celliophonic

Sissy Gets A Black Master By D.O.celliophonic@yahoo.comhttp://groups.yahoo.com/group/bestbbcstories/ I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the...

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But we're just guys, right?

by Jag2u612

CD's and TV's are not really chicks they are guys and they have guy sex drives! Unlike many online Cyber Queens as I call them. Years ago I did do some cross dressing. Unlike those AOL and Yahoo frauds I really did dress up and unlike them despite digital cameras being new things and very expensive I did get some shots of me dolled up. I found lots of gay guys wanted to suck dick and be...

Gay Erotic Story

My First Night Out With Jan and Rita

by William Penn

After a wonderful experience with Jan at his cigar shop in the late afternoon, William would find a new life had opened up to him. With Jan’s direction, William’s life would change for the better....

Gay Erotic Story

Interesting Suprise

by bjw

This all happened several years ago when I was in the Navy in San Diego. One payday weekend I was in a partying mood so I thought I would head down to Tijuana for some fun. Being I was about 20 at the time I headed for one of the clubs where a lot of the college kids hung out hoping that I might get lucky with some hot honey.After arriving at the club I found a seat in a booth and ordered...

Gay Erotic Story

Summer Job

by Christianlepseud

When I was in my twenties I was a student and needed to earn money for support. One summer I replied to an ad in which a student was wanted to help clear an attic of junk - seemed a good deal at the promised $4 an hour (was a while ago!) so I phoned and talked to he man who placed the ad and arranged to go around to be interviewed that same afternoon. The house was set in a big old tangled...

Gay Erotic Story

Sissy Bottom Boy

by mista_romantic

I would like to take the time to tell you about an experience I had a few years back. I was 18 years old living at home still in school and quiet innocent, I had not so much as even kissed a girl. Our house had two detached rumpus rooms, I lived in one and my parents had a lodger living in the other. The lodger’s name was Darren; he was 28 years old, red hair, and had a large muscular build....

Gay Erotic Story

A Bra and Panties?

by manix

It had been a long day, my friends and I had been on long ride in our local forestry area. We always parked our cars away from the usual cyclist parking areas so it was pretty well deserted. As we approached where we had parked we saw what looked like a lady by a tree in her undies. As we got closer we could see it was a guy in women’s underwear, stockings, suspenders, bra and silk panties. We...

Gay Erotic Story

Satisfied Client

by Shemale

This story was first published at blog I still remember my first time with a shemale. It was a tall thin blonde that came into the office of our law company one day. I knew she was an attorney of one of our clients and I thought her boss, and my friend, sent her to express gratitude for the very good deal we helped him to close. As I stood up from...

Gay Erotic Story

Ladyboy Switch

by newwriter

If you’ve read my previous posts you will be aware that I love cocks – sucking them and having them up my arse. I have been straight for most of my adult life but the last 18 months I have been on a huge cock binge. 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...

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