Sissy Fag Stories

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The 70's Weren't All Care Free

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

It was the 70's. Young, carefree, long-haired hippie, away from home, traveling around the country - having a ball. A couple guys I met and I decided to go for some beers. The local Y was in a sleazy part of town. So we ended up a pretty seedy bar which was hosting a rather bizarre strip show. At another table was an older guy that had been at the Y that aft...

My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

Mistress Kate Pt. 01

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

L. Jordan Bains wasn't sure of what to expect when he stepped into the large wood paneled office, but he knew whatever it was it wouldn't be good. He was in a lot of trouble, the Leprechaun wasn't known for having a forgiving nature. Jordan had never seen him, he only knew him by reputation, when you hung around the poker tables of Waller City you heard all...

Mistress Sylvia Pt. 01

by corduroysissy on Dec 18, 2018
Transgender & Crossdressers

Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergen...

Casey's Submissive Journey Pt. 01

by corduroysissy on Dec 14, 2017
BDSM

Karen walked into the bedroom and Casey thought he would have a heart attack. He was reading a book in the corner chair and looked up at his lovely wife. She was wearing a pair of dark red, mid-wale corduroy jeans. Casey had a corduroy fetish, corduroy turned him on a lot. He'd purchased many pairs of corduroys for her over the years and she knew the red o...