Sissy Nails Stories

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Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...

Casey's Submissive Journey Pt. 09

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

A day With Dorothy -- Part One - The Players Casey -- Submissive closet sissyfag with a corduroy fetish, owned by Karen. Karen -- Wife/Mistress to Casey and member of the Lady's Club. Julian - Submissive closet sissyfag owned by Dorothy (Dottie) Dottie -- Wife/Mistress to Julian and member of the Lady's Club. Maxie -- President and founder of the Lady...

Caught Red Handed

by desireethtttv on Sep 15, 2017
Transsexuals & Crossdressers

With Halloween falling on a Monday, my wife Suzie was busy the weekend before trying to find her costume to wear to work. As a dutiful sissy husband that loves shopping as much as any woman, I tagged along, although our choice of stores to peruse is completely opposite. Suzie is a Goodwill addict, with anything at a bargain giving her much pleasure. Me, I'd...

Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...

The Slave and the Sissy Ch. 01

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

I was more frustrated than ever now; Ella laughed wickedly as I was led away on my leash, my cock pulsing and dribbling like mad in its cage, was there no end to this torture? We turned a corner and we were approached by a smiling harem girl who, giggling passed a sack to mistress. We stood by a door to another room. Mistress tickled my balls before handing...

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

The Office Ch. 04

by EasilyConfused on Jan 23, 2018
Transsexuals & Crossdressers

There were six screens in total, one for each of those being monitored. Their heart rate, blood pressure and neural receptors all key indicators. The technician made gentle adjustments to the controls in response to certain measurements that she noticed on each of the screens before her. Behind her a woman in a business suit watched on. Paula Hamilton was sk...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

Becoming a Sissy Maid & Slut Vol. 02

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Four: My Arrival and a New Start to Full Time Sissy Life. I awake about 7:30am, groggy as I only had a floor to sleep on with a thin blanket, I rub my morning eyes as I sit up and see the black, satin, maids dress on a hanger, as if it was calling me to put it on. I soon realize my new predicament and smile. I had to take off the pair of pantyhose,...