Gay Crossdressing Stories, Page 10

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

8.7 (31) 7578 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) 1004 5 Min Comments

Tricked and treat for Halloween

By BillyBoy 3 Sep 2021

Tricked into crossdressing for Halloween

8.6 (28) 6047 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) 3593 5 Min Comments

Tricked into being his

By BillyBoy 1 Sep 2021

She got me hot, he took over from there

8.3 (33) 4956 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

6.0 (29) 4647 2 Min Comments

Pinked

By satyrDaddy 20 Aug 2021

Brad becomes Pink and finds his Daddy

7.6 (4) 1702 20 Min Comments

Pinked

By satyrDaddy 19 Aug 2021

Brad becomes Pink and finds his Daddy

8.2 (13) 1359 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) 4489 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) 2823 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 (69) 10856 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) 5317 31 Min Comments

Friday Night at the Neighbors

By satyrDaddy 5 Aug 2021

Kenny gets outed and used by neighbor couple

8.2 (26) 4218 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 (156) 15038 55 Min Comments

Jizelle

By satyrDaddy 23 Jul 2021

Jizelle becomes obsessed with Daddy watching her cum for him

8.3 (7) 1364 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.

9.1 (29) 12409 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 (110) 40767 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) 2101 5 Min Comments

Lingerie Disaster

By Frank Chainges 31 May 2021

I have always a little lingerie under my suits for work, has my luck finally run out???

8.0 (17) 3397 4 Min Comments

Mail Order Slut (ch. 3)

By bootlicker 25 May 2021

The captive sissy is prepared and opened for her owner, and taken repeatedly in a night filled with oral and anal fucking by the African Chief.

8.5 (52) 6463 14 Min Comments

Turned into a sissy

By Alleykat 16 May 2021

Forced by a stranger photographed blackmailed used by strangers at the park dressed like a little girl. This is the 3rd part of my adventure into becoming the sissy boy/girl I want to be.

8.9 (51) 12980 3 Min Comments

Sissy's Need Dick

By Mikal 9 May 2021

A lonely Crossdressing Femboi Isolated by the Covid restriction takes charge and gets the dick she so desperately needs

8.5 (28) 4494 8 Min Comments

Cherry (ch. 2)

By Cirkle7 2 May 2021

Meating Samantha

By JoeSoapNamibia 28 Apr 2021

My one and only meeting with a very hot cd

8.1 (10) 1223 10 Min Comments

Taken

By Alleykat 26 Apr 2021

Six years ago I was just a innocent boy, I took a shortcut home at the park late at night.

9.1 (72) 7100 5 Min Comments

Becoming a sissy wife (ch. 2)

By Punkboi18 3 Apr 2021

After I moved in with Rick I quickly became his submissive slave. I learned I loved my daily punishment and enjoyed the pleasure that comes with pain.

8.7 (61) 10777 3 Min Comments

Femboi Freddie at the Truck Stop

By Nathan James 27 Mar 2021

Freddie was a very femanine gay boy who them big old burly truckers loved.

6.4 (39) 10442 2 Min Comments

The cruising park

By Punkboi18 19 Mar 2021

My first night in my towns notorious cruising spot and my first time having anonymous sex with strange men.

9.0 (49) 5407 5 Min Comments

Girl friend sets me up to get turned into a sissy

By Wannabesissy 11 Mar 2021

So I'm 35 masculine male with beard and tattoos, I also have a girl friend. But I have a secret, when u get high on crystal all I can think about is big hard cock. So much so that I just run off on my gf and get caught.

7.8 (38) 10271 5 Min Comments

Just another night whoring

By desire_e4bbc 3 Mar 2021

Another beautiful night fulfilling my desires

8.6 (18) 3353 3 Min Comments