Page 8, Gay Crossdresser Stories

Sissy's Bizarre Adventure: A captivating tale of submission, desires, and sexual liberation as Dray embraces his inner sissy and dives into the world of BDSM, exploring the boundaries of pleasure, pain, and domination.

8.6 (21) 4414 3 Min Comments

The Governor's New Intern

By NakedBiGuy 11 Jun 2023

Tyler is saved from prison by a Homophobic Governor, but has to serve as his intern for a year

8.3 (40) 3938 7 Min Comments

Secret Kisses (ch. 2)

By luvaslip 7 Jun 2023

Contuing story of young and old beginners as they grow in their relationship. Joni wants all the cock she can give as Kyle tries to make her happy

8.6 (14) 1522 4 Min Comments

Caught by Aunt's Boyfriend

By Katie Femboy 5 Jun 2023

Stayed at my Aunts house most weekends, thought the house was empty and got caught in her lingerie by her boyfriend. He ran out quite fast but ended up sending me a drunken text message

8.5 (62) 10976 3 Min Comments

Edge Running

By Habu 30 May 2023

Profile of a CIA Candy Store Ops recruit: Chicago

9.8 (23) 2661 21 Min Comments

House help is my Master now (ch. 3)

By Slutty Whore 16 May 2023

Slave meets Master's friends.

8.8 (18) 3962 7 Min Comments

Family fun and games

By BillyBoy 15 May 2023

my uncle and aunt invite me to meet them and stay over for the weekend. they are naughty, nasty people, and i loved it!

8.4 (42) 5625 6 Min Comments

Bar Bathroom fuck

By Viki 14 May 2023

A story of how I finally got to courage to dress up and search for a cock to fill me up.

8.7 (52) 7479 8 Min Comments

Wife discovers husbands sissy secret

By SecretsissyJ 10 May 2023

Wife forces husband to embrace his sissy side after she discovered his secret stash

8.7 (104) 19981 6 Min Comments

House help is my Master now (ch. 2)

By Slutty Whore 9 May 2023

The door opens and a dark, hunky, broad guy enters. I am happy that it is not someone I know. Well, he is a tattoo artist and a friend of Master.

8.3 (24) 4418 4 Min Comments

Child hood bestfriend helping me open my eyes

By Famsammie 8 May 2023

When I first got started in general with crossdressing my childhood bestfriend help my development all the way around

8.8 (31) 6530 6 Min Comments

Grinder my way

By Fun bottom 8 May 2023

Please please please give me your thoughts I am trying to get back into the gay scene after a 13 year absence

3.8 (17) 2070 1 Min Comments

House help is my Master now

By Slutty Whore 7 May 2023

A hot hunk house help becomes the master to a newbie in a city . See how it happens!!

7.5 (38) 7454 5 Min Comments

Seduced and on my knees

By BillyBoy 5 May 2023

Visiting a hotel bar during a gay drag queen weekend, I become involved with some dominant crossdressing ladies

8.4 (18) 3065 3 Min Comments

My Vegas trip

By Jester4fun 24 Apr 2023

My real Vegas trip:)

9.3 (207) 4585 10 Min Comments

He showed me I have a girl inside (ch. 8)

By Jerryisjulie 24 Apr 2023

Daddy’s hold on me gets stronger - my lessons continue

9.3 (45) 6155 4 Min Comments

Prom Dress Contest for The Boys

By BillyBoy 22 Apr 2023

Having all the sissy's in town show up wasn't as hard as I thought

5.8 (10) 2892 8 Min Comments

Bras, Bros and Blowjobs

By BillyBoy 21 Apr 2023

my study buddy caught me playing in my sisters underwear

7.5 (25) 7752 5 Min Comments

First time sex as a CD

By Jester4fun 21 Apr 2023

My dream come true

9.2 (204) 8697 5 Min Comments

He showed me I have a girl inside (ch. 2)

By Jerryisjulie 15 Apr 2023

Overwhelmed from the last encounter, sissy Julie returns to the woods

9.0 (33) 7882 6 Min Comments

When I was first getting started

By Famsammie 14 Apr 2023

Living at home with my parents still my eager 19 yr old was begging for some type of action late at night

7.7 (16) 4671 4 Min Comments

Married to the Game

By Phaggotry 13 Apr 2023

A closeted ex-con biker queer marries a heterosexual woman to the lustful amusement of the colorful cocks they have in common.

8.9 (21) 2903 11 Min Comments

Loads and Tow

By Phaggotry 12 Apr 2023

An ex-con turned repo man gets entangled with his older bosses and his housemates.

9.6 (10) 4623 99 Min Comments

Being Used By Dad

By Phaggotry 10 Apr 2023

A crossdressing queer becomes a cum dump for his dominant father.

8.6 (66) 28226 13 Min Comments

I am the pervy Uncle

By BillyBoy 6 Apr 2023

Everyone has a pervy uncle, but it turns out, I am the pervy uncle

8.5 (37) 8266 17 Min Comments

A Star is Fucked

By Holden 29 Mar 2023

He bent over the bed, he lifted his red skirt, there were his pink panties with a slit for easy accesses to his ass hole. I smeared my cock with Vaseline and then rammed it in the panty slit into his ass. His slutty chute parted smoothly to accommodate my hard thick eight inches. He had blossomed as a girl.

8.8 (51) 9376 20 Min Comments

Russian Roommate (ch. 3)

By TyPeirson 27 Mar 2023

After finally taking Danyl's cock, "Jess" is ready to submit totally. After a trip to the gym, things don't end up going according to plan, and Jess's level of submission to the life of being a sissy is tested.

9.4 (69) 11325 13 Min Comments

Sissy panty boy can't find a dom to fuck him

By BillyBoy 22 Mar 2023

Been looking. I guess guys aret really into a panyboy unless they are young and pretty. I'm not either of those. But I'm willing, obediant and fun!

8.2 (16) 3019 5 Min Comments

A simple mistake

By BillyBoy 20 Mar 2023

My wife catches me in her underwear. She tells her friends. One of her friends husband call me. Then it begins.

6.7 (51) 8842 2 Min Comments

Kept Men

By Habu 13 Mar 2023

Young Lawyer gives special service in building of Biltmore Estate

8.8 (29) 2115 33 Min Comments