Page 5, Gay Crossdresser Stories

Jocks and Panties

By Victor 17 Jul 2024

Branson is a big, muscular, athletic jock who can't understand his need to be treated like an another man's bitch.

9.6 (84) 7944 19 Min Comments

Can I go back to my favourite club?

By Frankfurt Chronicler 16 Jul 2024

Our narrator has an unexpected sexual encounter with two men at the club while the band plays, losing his cherry and his pants in the same evening.

8.9 (24) 3072 11 Min Comments

Making the fantasy become reality (ch. 2)

By Try To Be Quiet 16 Jul 2024

Daddy had something planned for me this time, I wondered the whole week waht would happen during our next encounter

8.4 (12) 2438 8 Min Comments

Learning to be gay

By BillyBoy 3 Jul 2024

From playing in panties and shoving a dildo up my ass, I finally found a gay guy to fulfill my desires, fantasies and fetish needs.

8.0 (10) 3445 7 Min Comments

Loving my high heels (ch. 3)

By Prettyboy 27 Jun 2024

Jackie loves wearing high heels. He just received a pair of high black Chucks with 3" white heels. He meets Tom who is turned on by these Chucks and tops Jackie.

9.6 (8) 993 4 Min Comments

Straight guy turned gay (ch. 6)

By Jaden 27 Jun 2024

A new experience - It was Monday morning, I woke up and found myself alone in bed. I found the sexy french maid outfit on bed. I wore it and headed to the kitchen. My master was having breakfast by himself.

9.5 (27) 7680 9 Min Comments

Bent Over

By RedJulian 25 Jun 2024

A cross-dressing bodybuilder slut awaits our narrator at the door.

8.5 (23) 3122 3 Min Comments

Swapping Spit

By luvaslip 23 Jun 2024

Joni joined the Marines and rented an apartment in Carlsbad. She takes a fifteen day leave and meets a neighbor who helps her.

8.5 (13) 1156 7 Min Comments

Straight guy turned gay (ch. 3)

By Jaden 22 Jun 2024

Turned into a sex slave.

9.2 (56) 11947 6 Min Comments

Twins bothers have lot more in common

By Xoxo 22 Jun 2024

Harry finds his brother suck neighbour BBC without sharing with him

9.4 (16) 4829 19 Min Comments

My first gay kiss

By KellyGirl2010 18 Jun 2024

My first hook up with a guy I met online!!

8.3 (17) 3005 2 Min Comments

Keds Bitch (ch. 5)

By Prettyboy 16 Jun 2024

Tom likes to top pretty femboys. He meets Jackie who just bought a pair of red Keds. Tom goes to Jackie's shoe store and buys a new pair of purple cowboy boots. Tom wears his new boots as fucks Jackie in his red Keds

8.3 (8) 607 4 Min Comments

Becoming Joni Kayse

By luvaslip 13 Jun 2024

Joni and her Uncle are on their way to colorado, on a graduation trip., there is some naughtiness on the way.

8.6 (32) 3773 5 Min Comments

Crossdressing Boot Bitch

By Prettyboy 13 Jun 2024

Jackie is a crossdresser and has new pair of women's knee high white patent leather laced boots and is looking for a top. Jackie hooks up with a leather boy, Jeff.

7.9 (16) 1207 3 Min Comments

Big black ass fucked (ch. 2)

By Dondee 11 Jun 2024

I was born with a big ass .I got fucked many tim

8.2 (2) 4050 8 Min Comments

Uncle's Magic Hands

By luvaslip 11 Jun 2024

Uncle Owen has future plans for his pretty nephew. But patience is the big key.

9.0 (24) 5707 7 Min Comments

Dave

By LostSoul 31 May 2024

An amazing holiday hookup.

7.8 (16) 3053 7 Min Comments

First time at a gloryhole

By Jester4fun 26 May 2024

True story of my first time visiting a gloryhole

9.3 (143) 10396 6 Min Comments

My wishing star (ch. 6)

By Kaysa 24 May 2024

Kevin and Clark get to work. It's not easy for Kev with all his body changes, but it becomes harder when he forgets something very important...

8.9 (14) 1966 10 Min Comments

Only One Draw (ch. 8)

By Habu 14 May 2024

Missed Chances

9.3 (9) 613 20 Min Comments

Only One Draw (ch. 7)

By Habu 12 May 2024

Case Solved?

9.6 (6) 373 16 Min Comments

Only One Draw (ch. 6)

By Habu 10 May 2024

The Pitches

9.7 (7) 773 20 Min Comments

Only One Draw (ch. 5)

By Habu 7 May 2024

Layla’s Move

9.7 (7) 435 23 Min Comments

Only One Draw (ch. 4)

By Habu 5 May 2024

Ravished

9.8 (7) 633 32 Min Comments

Walking in the Mall

By luvaslip 5 May 2024

Jerry meets a charming new friend while out for an early walk in the local Mall.

8.3 (9) 3104 6 Min Comments

Chrisy - The Sissy Slave

By Slutty Whore 4 May 2024

See how two horny ass adults convert a straight boy into a submissive sissy slave that becomes a horniest slut

8.3 (63) 12496 6 Min Comments

Only One Draw (ch. 3)

By Habu 3 May 2024

Grisly Finds

9.7 (8) 429 29 Min Comments

Married Man love being a woman

By Joey 2 May 2024

Married Man prefers to be a woman

8.5 (29) 4980 2 Min Comments

Only One Draw (ch. 2)

By Habu 1 May 2024

Covered in the Night

9.6 (6) 600 30 Min Comments

Only One Draw

By Habu 29 Apr 2024

The Exhibition

8.9 (11) 2451 26 Min Comments

Stacey's First Love (ch. 2)

By luvaslip 15 Apr 2024

Stacey goes into the Army where he meets Dexter and they have a love filled weekend.

9.7 (11) 1000 4 Min Comments

Wearing my wife's thongs

By Viki 15 Apr 2024

Just a short story - I sent him pictures of me in my wife's thong. He liked them, especially how my ass looked in them.

8.0 (10) 3811 4 Min Comments

Planet of the Dominated Mind

By E. Roan 14 Apr 2024

Captain Lukas is close to retirement, but he thinks he has one more mission in him. He leads two rookies on a galactic chase for a petty drug dealer, only to find something far more dangerous on the uninhabited mining planet ER-14...

9.3 (21) 3780 72 Min Comments

Stacey's First Love

By luvaslip 14 Apr 2024

Stacey remembers her first love and more

9.5 (11) 1696 17 Min Comments

The pond

By luvaslip 8 Apr 2024

Stacey is at her friend and lover's funeral as she reflects on the past.

9.1 (4) 568 23 Min Comments