Gay Sissy Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressed and made into girls and sissification.

Neighborhood faggot boy

By Alleykat 24 Dec 2021

My address was on the bathroom stall.. Cocksucking cumloving pretty boy cruise by after 9pm weekends

9.0 (82) 19583 7 Min Comments

Cross dresser.. Twink.. Tranny?

By djfmonkey 22 Dec 2021

My straight buddy and I visit a gay bar, where we discover our own inner selves, and the truth about each other

9.3 (166) 8230 8 Min Comments

Chis(topher) & Chris(tina) (ch. 3)

By djfmonkey 12 Dec 2021

Chris and I finally visit my parents for the holidays in my overly homophobic upstate New York Hometown

9.6 (119) 2301 11 Min Comments

Secret Sissy

By BillyBoy 10 Dec 2021

I've been in the closet all my life. Finally, I have a chance to try out being a sissy girl for a real man

7.2 (11) 4702 5 Min Comments

Dreams and Frustration

By BillyBoy 9 Dec 2021

Every day I awake from a dream of being used as a girl whore. I can't stop it. I'm in trouble!

7.9 (12) 2681 5 Min Comments

Still cruising at the mall

By Alleykat 8 Dec 2021

After sucking older guys in the restroom at the mall. I let this other guy pick me up and take me to his van.

8.8 (24) 5336 5 Min Comments

Halloween party

By BillyBoy 2 Dec 2021

I finally let him seduce me. I agree to meet him. He has been flirting and making promises. Then at the last minute, he tells me I'm going to dress like a woman tonight.

8.0 (17) 4385 3 Min Comments

Park Slut (ch. 3)

By Alleykat 30 Nov 2021

Turned into the park cocksucker by a fat old man

8.9 (28) 4113 7 Min Comments

Chis(topher) & Chris(tina) (ch. 2)

By djfmonkey 23 Nov 2021

Chapter 2. - Chris and I meet the grandparents

9.7 (116) 2042 5 Min Comments

Chis(topher) & Chris(tina)

By djfmonkey 22 Nov 2021

I met and fell for a crossdresser, explore chapter 1 introducing us, and future chapters meeting family and friends

9.3 (127) 4355 9 Min Comments

How this straight guy became a sissy bottom

By Somewhat Straight 17 Nov 2021

It took while, but my transformation is complete

8.4 (352) 75934 9 Min Comments

In a short span I became a sissy boy trap (ch. 2)

By Desertbiguy 10 Nov 2021

I had spent all of my time getting indoctrinated in gay sex by Tom G. I forgot about my first man to pop my anal cherry Mark.

8.1 (22) 2945 3 Min Comments

In a short span I became a sissy boy trap

By Desertbiguy 8 Nov 2021

Halloween changed my life to being a sissy boy trap. I dressed up to be a girl at a big jr high party. After that I was addicted to cock. Discovered craigslist. Put and ad as a sissy boy dressed up as a girl. Met Tom G older guy. Both times I was fucked doggy style. Introduced me to gay sex. My butt is a true boi pussy.

8.7 (35) 11252 10 Min Comments

Crossdressing

By BillyBoy 2 Nov 2021

Envious of the girls always getting to wear those cute little bras and panties.

8.5 (19) 4654 10 Min Comments

Halloween is a great time to express sexual feelings

By Desertbiguy 2 Nov 2021

I decided to dress up as a girl for halloween. There was a big party going on for us jr high kids. And looked good. Maybe to good. Mark was a good looking guy. Something happened at party. He became attracted to me.

9.0 (60) 4174 4 Min Comments

Becoming the Fishing Camp Princess

By Dickguy4U2 31 Oct 2021

While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way

8.8 (54) 6865 24 Min Comments

Bunny and Daddy (ch. 3)

By satyrDaddy 22 Oct 2021

Bunny webcams with Daddy...and more

8.2 (7) 1389 4 Min Comments

Prom night for a sissy crossdresser

By BillyBoy 19 Oct 2021

I meet a cute sissy out for prom night. But he needs a date.

8.1 (27) 3255 4 Min Comments

Bunny and Daddy

By satyrDaddy 17 Oct 2021

Bunny can't wait to cam with Daddy

8.6 (7) 3207 4 Min Comments

My boss brings me into his kinky BDSM world

By BillyBoy 17 Oct 2021

The title says it all

9.1 (33) 7371 9 Min Comments

Being Ricky's girl for the night

By kewlie 9 Oct 2021

Being used like a queer is a turn on, but being treated like a girl is too!

9.1 (50) 7074 11 Min Comments

Sex at a funeral home

By Alleykat 9 Oct 2021

Seduced at a funeral home by older strangers

8.9 (60) 5469 8 Min Comments

first time caught in hers

By BillyBoy 6 Oct 2021

Wife catches me the first time. Very embarassing. But not at all as bad as when she turns me over to the kinky gay guy she works with.

8.7 (29) 5211 10 Min Comments

Blackmailed

By Alleykat 24 Sep 2021

I was blackmailed to be a sissy faggot for old men

8.5 (56) 16412 4 Min Comments

Bathhouse Frenzy

By popperboi 16 Sep 2021

My first visit to a bathhouse, where I learn about poppers and BBC

8.7 (85) 14966 4 Min Comments

A Sissy Boys Hard lesson

By Badman 15 Sep 2021

Interracial story. A sissy boy meets a cruel mature black man and dresses as a pigtailed girl for him. The cruel man treats the little sissy rough, tearing off his clothes and ripping apart his favourite little white cotton school panties before spanking and raping him. The theme and story line runs parallel to "Sissy Boy Loses Panties To Perverts"

9.0 (245) 64704 18 Min Comments

fantasy about being found out and moved up one more step

By BillyBoy 7 Sep 2021

discovered by my boss and then he makes me his sissy bitch

9.1 (33) 5059 9 Min Comments

Straight to a sissy (ch. 3)

By Alleykat 7 Sep 2021

Young pretty sexy hot n horny love public sex

9.0 (34) 6199 4 Min Comments

I suppose this is how it all started for me

By BillyBoy 6 Sep 2021

I remember like it was yesterday. Girls' underwear, being tied up, helpless. I guess I loved it

8.2 (12) 3789 6 Min Comments

My brother's friend is a sissy fag

By BillyBoy 4 Sep 2021

Well, I fianlly had enough and gave it to him. The little sissy fag

8.8 (33) 8482 7 Min Comments

I guess I was asking for it

By BillyBoy 2 Sep 2021

I posted some pics of me in my sister's panties and bra. I guess I should have expected to be used like a girl slut

8.1 (15) 3825 5 Min Comments

Tricked into being his

By BillyBoy 1 Sep 2021

She got me hot, he took over from there

8.5 (36) 5544 4 Min Comments

My college days and my secret gay life (ch. 3)

By Desertbiguy 23 Aug 2021

I just had my second gay sex encounter. I had sex in a bar parking lot. And met a guy at a fraternity. I was always fascinated with gay street walkers. Getting paid to have sex with gay or straight men. I found a such a street in my college town. I wanted to check it out if i could do it.

8.7 (48) 2941 4 Min Comments

Pinked

By satyrDaddy 20 Aug 2021

Brad becomes Pink and finds his Daddy

7.6 (4) 1897 20 Min Comments

My college days and my secret gay life

By Desertbiguy 18 Aug 2021

I finished up high school. I was accepted into CSU. I had used the bus and dressed up as a sissy to be fucked by men. I got my drivers license. And I was on my way to college. I did not expect to see any dick in my ass during this period of my life.

8.2 (77) 5234 5 Min Comments