Gay Crossdressing Stories, Page 5

Tie me up and fuck me like that

By BillyBoy 11 Aug 2023

The first time with a dom alpha guy and I ask to be tied up. But why?

8.9 (29) 6022 8 Min Comments

Frat Initiation

By Victor 2 Aug 2023

The president of the frat is slowly manipulating his freshman pledge, a masculine, cocky, gorgeous muscleboy to his will during hell week when all the pledges have to dress up like French maids and serve their future frat brothers at a party. The new pledge realizes he liked it a little too much.

9.3 (162) 16889 28 Min Comments

First or was panties

By Alleykat 24 Jul 2023

I kept staring at those sexy panties in the adult bookstore

9.4 (83) 8942 5 Min Comments

Mentor

By BillyBoy 14 Jul 2023

I'm not a young buck anymore, but another old man showed this dog some new tricks.

6.7 (16) 2413 3 Min Comments

Bobby's Pink Panties

By luvaslip 6 Jul 2023

Bobby has been hiding a big secret and he meets a stranger who helps him fulfill that secret and more.

8.8 (69) 6934 5 Min Comments

Playdate with Daddy

By BillyBoy 26 Jun 2023

call me daddy. yes Sir. oh, sorry, yes daddy

8.6 (28) 7102 8 Min Comments

A visit to Canada changes my life

By Maikol 11 Jun 2023

I was cleaned up inside and out. He liked that my body was hairless and commented about not having to shave. Dressing me up in stockings, garter belt, panties, bra and a very girly dress all in pink we went to the living room where he sat on one end of the couch and I kneeled in the middle being instructed on how to suck cock.

8.5 (42) 4725 4 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

8.7 (13) 1407 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 (58) 10168 3 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.

8.8 (49) 6988 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

8.8 (74) 14263 6 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

8.9 (29) 6172 6 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

8.3 (16) 2664 3 Min Comments

My Vegas trip

By Jester4fun 24 Apr 2023

My real Vegas trip:)

9.3 (202) 4258 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

9.2 (38) 5369 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) 2588 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) 6907 5 Min Comments

First time sex as a CD

By Jester4fun 21 Apr 2023

My dream come true

9.3 (195) 7551 5 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

7.2 (13) 4244 4 Min Comments

Being Used By Dad

By Phaggotry 10 Apr 2023

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

8.7 (60) 23084 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

8.4 (34) 7237 17 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 (63) 9971 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!

8.1 (15) 2504 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.

6.6 (48) 8185 2 Min Comments

Kept Men

By Habu 13 Mar 2023

Young Lawyer gives special service in building of Biltmore Estate

8.8 (29) 1977 33 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

6.1 (5) 606 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

9.1 (12) 2770 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.

8.1 (44) 15103 12 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) 5624 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 (20) 2851 37 Min Comments