Gay Crossdressing Stories, Page 9

Some anonymous man recognized me from my posts on this website. He orders me to meet him at a hotel but I can't see who he is. Now everyone I know is a suspect. It's really weird and scary in a kinky sort of way.

8.7 (30) 8366 3 Min Comments

A Sissy Boys Hard lesson

By Badman 15 Sep 2021

Interracial story. A sissy boy meets a cruel mature black man and dresses as a pigtailed girl for him. The cruel man treats the little sissy rough, tearing off his clothes and ripping apart his favourite little white cotton school panties before spanking and raping him. The theme and story line runs parallel to "Sissy Boy Loses Panties To Perverts"

9.0 (236) 61804 18 Min Comments

he is a bad man

By BillyBoy 12 Sep 2021

He orders me to dress in her underwear. Put on some tight restraints. I have to drive for an hour to his home. Then he treats me like his own sex toy, sex slave, and spank bitch. But I keek coming back. He is a bad man.

8.5 (17) 2234 3 Min Comments

Caught and compromised

By BillyBoy 11 Sep 2021

The guy next door was watching me dressing in my moms and x wife's old underwear for a while. He watched me playing with some self bondage for a while, too. So, this day, he bursts in and grabs me, just as I'm cumming all over. Now I'm at his mercy.

8.9 (27) 6601 11 Min Comments

fantasy about being found out and moved up one more step

By BillyBoy 7 Sep 2021

discovered by my boss and then he makes me his sissy bitch

9.1 (32) 4729 9 Min Comments

Straight to a sissy (ch. 3)

By Alleykat 7 Sep 2021

Young pretty sexy hot n horny love public sex

8.8 (29) 5310 4 Min Comments

I suppose this is how it all started for me

By BillyBoy 6 Sep 2021

I remember like it was yesterday. Girls' underwear, being tied up, helpless. I guess I loved it

8.2 (12) 3002 6 Min Comments

he noticed my panties under my jeans

By BillyBoy 5 Sep 2021

caught in panties by a stranger who wanted me for sex and more sex

8.7 (30) 5107 5 Min Comments

My brother's friend is a sissy fag

By BillyBoy 4 Sep 2021

Well, I fianlly had enough and gave it to him. The little sissy fag

8.8 (30) 7180 7 Min Comments

My Fetish for sexy crossdressers

By Daves 4 Sep 2021

Prefer top or versatile crossdressers like smooth. I enjoy getting buttfucked. Love sucking dick. Prefer smooth, not hairy. Mutual sucking. Like taking turns fucking each other. Was always attracted to fem boys just turned me on.

6.8 (6) 970 5 Min Comments

Tricked and treat for Halloween

By BillyBoy 3 Sep 2021

Tricked into crossdressing for Halloween

8.6 (28) 5797 3 Min Comments

I guess I was asking for it

By BillyBoy 2 Sep 2021

I posted some pics of me in my sister's panties and bra. I guess I should have expected to be used like a girl slut

8.0 (14) 3487 5 Min Comments

Tricked into being his

By BillyBoy 1 Sep 2021

She got me hot, he took over from there

8.3 (33) 4747 4 Min Comments

Crossdressing twink gest fucked in an adult store

By gaystories 22 Aug 2021

Crossdressing twink gest fucked in an adult store with victoria's secret

5.8 (28) 4601 2 Min Comments

Pinked

By satyrDaddy 20 Aug 2021

Brad becomes Pink and finds his Daddy

7.6 (4) 1641 20 Min Comments

Pinked

By satyrDaddy 19 Aug 2021

Brad becomes Pink and finds his Daddy

8.2 (13) 1336 6 Min Comments

Bus trip to other city leads to my first time with a man (ch. 8)

By Desertbiguy 17 Aug 2021

I started off as a young teen being introduced to gay sex. I had a sexual impulse to act out on them. Having sex in public bathrooms full filed my desire to be an anal slut to men. Then I was curious in becoming a dressed up sissy. And found it more exciting to tease men. My next encounter was with 2 black guys. Enjoy!!

8.6 (21) 4425 4 Min Comments

Taking it a little to far

By LovebeingJoanne 14 Aug 2021

I love dressing as a girl, I just can't help myself, every time I would dress up, I would go a little further with my appearance, until the day I realized that I had taken it a little too far.

8.5 (24) 2759 5 Min Comments

From Bad Boy To Good Girl

By Ms. Dee Praved 13 Aug 2021

This is a fantasy I have about being feminized and made into a slave by sadistic prison guards. I write as nineteen year old Chris, who was sent to serve a ten year sentence.

8.6 (68) 10352 5 Min Comments

Little Orphan (D)Annie

By bootlicker 9 Aug 2021

An eighteen year old is sold into slavery by his foster father and trained as a sissy-slut for an older married couple

8.1 (34) 4974 31 Min Comments

Friday Night at the Neighbors

By satyrDaddy 5 Aug 2021

Kenny gets outed and used by neighbor couple

8.2 (26) 4166 7 Min Comments

Made Over

By Victor 27 Jul 2021

College football star meets a man who shows him he can be a stud with a feminine side.

9.3 (147) 14590 55 Min Comments

Jizelle

By satyrDaddy 23 Jul 2021

Jizelle becomes obsessed with Daddy watching her cum for him

8.3 (7) 1341 1 Min Comments

From student to sissywhore (ch. 4)

By bootlicker 5 Jul 2021

The final chapter...Philippa is used, trained, stretched and abused for the pleasure of her two older, sadistic Masters.

9.2 (28) 11664 18 Min Comments

The first time i got caught crossdressing

By A Anal Addicted Slut 3 Jul 2021

Caught crossdressing & what i had to do to have my secret kept.

8.6 (105) 38201 11 Min Comments

I love My Dirty Daddy (ch. 5)

By Mikal 16 Jun 2021

So I have been a bit busy with work lately but I still wanted to add to the I Love my Dirty Daddy stories but how I mean it would get boring if every story is about Daddy handing Lola over. So I thought perhaps a prequel on how they actually got together in the first place.

8.6 (6) 2041 5 Min Comments

Sissy Boy Loses Panties To Perverts

By Badman 1 Jun 2021

A teenage boy dresses as a cute pigtailed schoolgirl for an old pervert who invites groups of mature masked black men to use him for rough spanking games and rape play. The cruel men enjoy spanking him, ripping apart his little white schoolgirl panties and abusing him. Thick black cocks fill him as the men use him for their pleasure.

9.2 (206) 24760 108 Min Comments