Gay Crossdressing Stories, Page 4

Prison Substitute

By Con Twink 21 Aug 2024

A fresh juvenile comes into contact with hardened criminals, and one in particular has a profound influence on him…

6.4 (46) 13649 2 Min Comments

Cruising the Highway

By deansaz 2 Aug 2024

Just on a short drive down the highway when a couple girls began flirting with me from another car on the highway.....

8.3 (26) 2716 3 Min Comments

College and finding the real me

By KellyGirl2010 29 Jul 2024

After graduating high school, I try to figure out who I am and I find that in the arms of another man. Parts of this story are true like my first time panty shopping, going to the adult bookstore, my brother knowing about me wearing panties and the college LGBT Center.

9.1 (30) 3808 23 Min Comments

Call Me a Fuckin Fruit

By Prettyboy 28 Jul 2024

Jackie is wearing a new pair of pink leather shorts with the hopes of attracting a horny top. Jim is a turned on by Jackie's shorts and enjoys her ass both in the gorgeous pink leather and also in the flesh.

8.1 (11) 1226 5 Min Comments

Finally giving in

By ClosetCd 28 Jul 2024

A married husband finally giving in to his desires

9.1 (82) 6615 6 Min Comments

I Love Fucking Femboys

By Prettyboy 26 Jul 2024

Jerry is bisexual but in the end he prefers a femboy's pussy. He meets Tommy who looks so cute in his white leather shorts and Nike Cortez and they hook up for some hot sex.

7.5 (20) 5001 4 Min Comments

Wearing panties

By KellyGirl2010 25 Jul 2024

Sucking my first cock

8.1 (20) 7285 7 Min Comments

BDSM lovers

By BillyBoy 24 Jul 2024

I wander into a sex shop for gay BDSM lovers. I'm in the wrong place!

8.9 (44) 3502 6 Min Comments

Just to Dream a Dream

By luvaslip 20 Jul 2024

Terry arrives at her uncle's house early and lays down for a nap. She dreams a dream that becomes real and gets a lot of loving.

8.9 (12) 1301 2 Min Comments

Twins bothers have lot more in common (ch. 3)

By Xoxo 19 Jul 2024

Harry gave his BBC friends a little show

8.8 (9) 2444 7 Min Comments

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 (81) 7247 19 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) 2338 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) 3206 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) 958 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 (25) 7157 9 Min Comments

Bent Over

By RedJulian 25 Jun 2024

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

8.4 (21) 2952 3 Min Comments

All Fun and Games (ch. 2)

By Sam Lil 23 Jun 2024

While the others try to find a way to escape, it becomes clear that the only way for them to leave is to fulfill their task. Michael and Damien seem to be up first.

9.4 (32) 4043 13 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.

8.4 (12) 1075 7 Min Comments

My first gay kiss

By KellyGirl2010 18 Jun 2024

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

8.3 (17) 2791 2 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.

8.5 (31) 3529 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.

8.3 (15) 1100 3 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.

8.9 (22) 5324 7 Min Comments

Dave

By LostSoul 31 May 2024

An amazing holiday hookup.

7.8 (16) 2956 7 Min Comments

First time at a gloryhole

By Jester4fun 26 May 2024

True story of my first time visiting a gloryhole

9.3 (137) 9524 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) 1852 10 Min Comments

Only One Draw (ch. 6)

By Habu 10 May 2024

The Pitches

9.7 (7) 725 20 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.

8.1 (8) 2917 6 Min Comments

Auntie and Uncle

By David Tossell 4 May 2024

A boy living with Aunt and Uncle for a holiday

6.6 (33) 5873 3 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

8.4 (59) 10806 6 Min Comments

Married Man love being a woman

By Joey 2 May 2024

Married Man prefers to be a woman

8.4 (26) 4670 2 Min Comments