Gay Crossdresser Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers.

The Family Affair

By Phaggotry 13 Mar 2023

An unusual tale of a sissy named Samee impregnated by her late stepbrother, only for her stepfather to be fingered as the baby's father. To get "her" out of her stepfather's grubby grips, she is sent to live with her estranged father and his new girlfriend before being passed off to her paternal grandfather and uncle in the classic cliche of "out of the frying pan, into the fire."

9.2 (20) 7287 51 Min Comments

Ron & Hema first encounter

By Hema CD 9 Mar 2023

Read how ron and hema had their first encounter. second part coming soon

6.7 (6) 666 9 Min Comments

A unexpected good time (ch. 2)

By Famsammie 5 Mar 2023

Waking up next to chelsea after a night with her brother mark and friend Lamar

9.2 (13) 2860 6 Min Comments

My Father Loves My Trans Ass

By Phaggotry 3 Mar 2023

Arin knew his father never liked him. His other sons were men and Arin felt more like a girl and dressed accordingly. Her world starts to unravel when things goes bust with her boyfriend and her father decides to violently pluck her cherry.

8.2 (47) 20142 12 Min Comments

Russian Roommate (ch. 2)

By TyPeirson 2 Mar 2023

James, otherwise known as Jess, moves into campus and finally gets to meet Danyl. Over the course of one day, does their secret already get out?

9.4 (71) 12781 16 Min Comments

The bully (ch. 3)

By Darksicko 1 Mar 2023

I pressed my lips like a kiss on his asshole and pressed my tongue in. His tight hole pushed it out right away and a hand grabbed my neck. I kept at it and after ten presses his but started letting me in.

8.2 (23) 6470 6 Min Comments

It all started with an innocent blowjob (ch. 2)

By Viki 28 Feb 2023

It is a story of a young gay man discovering his needs and desires. Experimentation and first encounters, experiences, and something more.

8.9 (21) 3123 37 Min Comments

Swingers trick me into being their bitch

By BillyBoy 28 Feb 2023

Bob and Lacey invite me over to join their swingers' group. But I'm alone with them.

7.3 (26) 5920 3 Min Comments

The bully (ch. 2)

By Darksicko 28 Feb 2023

I lay in the backseat for a few hours before i hear the car being opened. Hands grab me but something seems off. They throw me face down and i hear the unmistakable sound of a knife switching open. I feel them start to saw away at the tape and before long i am free.

7.6 (22) 6299 5 Min Comments

my sissy encounter turns into a bondage fuck-fest

By BillyBoy 27 Feb 2023

Greg searches for submissive sissy type guys on the dating sites. He messages me, seduces me, dresses me in silk and lace, and begins playing in some light bondage. Then he introduces me to his Dom daddy, Bob

8.8 (31) 7940 5 Min Comments

The bully

By Darksicko 27 Feb 2023

Extreme fetish. The bullying gets out of hand.

7.8 (33) 10946 4 Min Comments

Slam 'n' Scram (ch. 2)

By Phaggotry 21 Feb 2023

Kingsfordland, Tennessee, 1937 — Lollo Aurelie is a city slicker mobster running from trouble up north when he stumbles upon a mountain hick town ripe for a takeover. When moonshiners revolt to his dastardly deeds, they dress him “purdy” in drag and each of his captors have their way with him on a platform deep in the backwoods. They affectionately call him Priscilla Pumpernickel, a late whore who died drowning on a load.

8.4 (14) 2503 20 Min Comments

The Sissy Transformation of Christian

By TheNaughtySlut 18 Feb 2023

Christian has turned 18 Years Old, and his friend's sister is interested in him. What happens next nobody could anticipate, Christian becomes a sissy cock-loving cumslut. But how does this happen? Find out by reading The Sissy Transformation of Christian.

9.1 (54) 10638 13 Min Comments

It all started with an innocent blowjob

By Viki 8 Feb 2023

It is a story of a young gay man discovering his needs and desires. Experimentation and first encounters, experiences, and something more.

9.3 (40) 4661 36 Min Comments

Sexy CD's first gay encounter (ch. 2)

By fanny 6 Feb 2023

After our first encounter, he was getting hungry again for some of my ass. After a month, I saw some new packages was sent to me. As I opened them, noticed there are some new sexy lingeries and dresses with panties.

7.9 (15) 1961 2 Min Comments

Cabot's Adventures

By satyrDaddy 29 Jan 2023

An elder gentleman finds new lust

7.7 (12) 2202 6 Min Comments

Princess and King Show Off

By BeefyFem 27 Jan 2023

Every household needs both roles determined. I’m the husband, you’re the wife. You’re my Princess, I’m your King. This is the dynamic King and Princess decide to show off to the world.

8.6 (17) 3365 6 Min Comments

Hendry

By satyrDaddy 18 Jan 2023

Hendry is an ambitious femboy

7.5 (12) 2716 2 Min Comments

A unexpected good time

By Famsammie 15 Jan 2023

When my drag queen friend falls a sleep early and I'm left with her brother and best friend.

8.5 (37) 4541 5 Min Comments

He Wanted Sex In Lingerie

By Jjj1975x 5 Jan 2023

I am a married man who met a guy at a party. The guy wanted to have sex with me in lingerie. That is, he wanted me to wear lingerie. I didn’t think I would like it. But it was amazing.

8.9 (38) 7617 15 Min Comments

Cd curious of what a homeless man is packing

By Famsammie 19 Dec 2022

Everyday to work I would see the same homeless pitching quite the tent in the morning from sweat pants

9.0 (62) 9621 7 Min Comments

You're Kind of a Shitty Person (ch. 3)

By James 15 Dec 2022

Five minutes into his new job and Daniel already has an attitude. Ralph warns him against being disobedient during his job orientation, but perhaps his warning was too harsh. He didn't mean to upset his new employee, but he did find Daniel's crying face kinda cute.

8.8 (10) 3632 6 Min Comments

CD meets BBC first time

By Famsammie 12 Dec 2022

When he said I don't know I think 6 inches when I asked how big, I should of known that was a lie

8.6 (60) 11838 6 Min Comments

Walking the dog leads to more (ch. 2)

By Frankfurt Chronicler 12 Dec 2022

We almost get away with it, but Lars' friends find us and want a piece of the action. This is another long read, but with a ton of sex.

9.3 (21) 2977 22 Min Comments

Walking the dog leads to more

By Frankfurt Chronicler 10 Dec 2022

A mature sissy encounters a young top and his friends in the woods while walking the dog. This is a longer read and my first story, so I'm grateful for any feedback.

9.2 (35) 3791 18 Min Comments

Instructor Mike's Academy

By qtaimee 9 Dec 2022

A sheltered an innocent south asian teen with a mostly absent finder finds his Superior White Daddy on the fledgling internet in the early 90s. Can Instructor Mike mold the little peepee girl into his perfect sissy to service his Tremendous White Cock? Class is in session for little aimee. (Parts 1-6)

8.8 (15) 7407 140 Min Comments

Heather (ch. 6)

By Heather_xd 7 Dec 2022

Been a delay but here is the continuation of the whore Heather

4.0 (5) 695 1 Min Comments

Bodybuilder's Bitch

By Victor 26 Nov 2022

College athlete wears lingerie for two bodybuilders from his gym.

9.3 (120) 16405 10 Min Comments

You're Kind of a Shitty Person (ch. 2)

By James 22 Nov 2022

Brad takes Daniel to the gym to start his new job. Daniel is reluctant to work for sweaty gym bros, but needs the money. Unfortunately, the only gym clothes that fit Daniel are Brad’s Ex’s pink halter top and Juicy track shorts. Daniel is not pleased…

8.4 (11) 3792 6 Min Comments

A man see me in panties became an obsession (ch. 3)

By rivi 17 Nov 2022

Meeting strangers for sex is a world in itself . Most men attending outdoor cruising areas are not crossdressers but have a range of sex desires which have to be approached appropriately

8.0 (9) 4461 4 Min Comments

A man see me in panties became an obsession (ch. 2)

By rivi 15 Nov 2022

I cruise for the first time and learn what that involves .

7.4 (12) 4301 10 Min Comments

A man see me in panties became an obsession

By rivi 13 Nov 2022

A custodian at high school who had made a pass at me was remembered as being the only person I was sure was homosexual and as my crossdressing urges grew stronger he became the focus of a plan to act them out . What follows is true .

7.0 (11) 5029 7 Min Comments

Twenty one years of of bisexual exploration (ch. 4)

By Married secret bi 2 Nov 2022

A bad encounter leads to another break and a lot more cross dressing exploration

7.2 (10) 1572 4 Min Comments

Sexy CD's first gay encounter

By fanny 31 Oct 2022

I’ve never thought about of gay sex in my life so far. But one night it changed. As usual boring weekend, I was scrolling through some porn and all of a sudden, some hypno sissy gay porn videos kinda got my attention.

8.7 (16) 3470 3 Min Comments

The Bet (ch. 11)

By Bastian Ward 25 Oct 2022

Nick thinks he has to be the most unlucky person in the whole world, not only has he traded three masters for one, the one seems to be more sadistic than the three combined. To add insult to injury, Oliver's friend is now living in Nick's house, with seemingly no way out for Nick.

7.9 (12) 4981 36 Min Comments