Sissy Glory Hole Stories

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Infinite Scroll

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

Away with the Lads

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You're invited to Dublin, Ireland with 10 other lads from your village. It's planned as a weekend of copious quantities of drink (Guinness), fast food (beef burgers and chips) and cultural interest (Girls). You fly from Southampton and costs are kept to a minimum. Aiden, The only Irish born lad in the group fails to show – selfishly this is good news, as unl...

Tammy's Panties

by pantyperv on Sep 25, 2017
Fetish

I developed my panty fetish early in life when I discovered my sister's lingerie drawer. Like most young males, I began to discover masturbation around puberty. Discovering my sister's panty drawer added a whole new dimension to my methods of masturbation. The feel of satin drove my dick wild. I would either wrap her panties around my dick or jack off, or I...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Mistress Red Fox Becoming a Devotee Pt. 03

by His_fag_wife on Nov 18, 2019
Transgender & Crossdressers

Miss Red was busy moving around the room. I wasn't sure what she was doing, but could hear her moving various bits of equipment. Then she moved the bed away from the wall. I realised that it must be on wheels. As she continued to work in the room, my mind drifted to what she'd just said. Fuck she said she understood subs, so she must be into this whole sce...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Bird of Prey Ch. 13

by Sputnik57 on Sep 14, 2017
BDSM

Clyde made sure he recorded everything as Fox-Janner greeted the soft blonde, not with a kiss, but a harsh slap about the face; he then virtually dragged the distressed nymph up the stairs, his cock poking up and lifting the black silk. In the bedroom he ordered her to strip, and with just her panties on, he pulled her down on to her knees by her long blonde...

What If You are the Whirlwind? Ch. 02

by Sublissimal on Jan 23, 2019
Non-Erotic

"Imagine for a moment, if you would A life that's not defined in bad and good But chained instead with shameful aching need To eat the fruit and try to hide the seed." ___ Rayna ___ Rayna's bare feet pound the hard-packed dirt as she runs for the hidden safety of the trees. At least the shoes are in hand. She had to take them off when she started running...

The Proof is in The Pudding

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

When my girlfriend of two years mentioned she liked to watch female impersonators perform, I seized the opportunity to confess my lifelong addiction to cross-dressing. The expected reaction of disbelief was no surprise but her reply of, "Well, let me see you dressed," was although welcomed, a bit of a setback. I'd not planned the truth to be revealed at suc...

Yesterday Afternoon

by allourdesires on Jun 10, 2019
Transgender & Crossdressers

A lunchtime call; I was to leave work immediately. Once home I would find everything laid out on the bed: nightie, bralette, cotton panties, hold-ups, lipstick, silver choker and...a blindfold? When I was ready I rang her as ordered, covered my eyes and began to toy with my nipples in anticipation of what was to come. My little clitty jumped inside my panti...