Sissy Permanent Collar Nun Stories

56,025 results
Orientation
Length
Source
Infinite Scroll

Healslut Adventures

by agenteightysix on Jun 22, 2020
Fantasy

"And don't come back!" That's the last you hear before you're kicked out into the street and a door is slammed behind you. This isn't the first time you've been kicked out of an inn, but it is the first time you have been thrown out into the street in the middle of the day stark naked, your belongings kept by the proprietor to pay your debt. You bl...

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Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

Gym Submission Ch. 04

by AltErik on Sep 16, 2017
Transsexuals & Crossdressers

************ Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains Male/Male sex, Male/Female sex and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. I hope you enjoy it and fee...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...

Kinky Dentist Sian And Sissy Rachel Ch. 02

by Sissy Adele Howells on Dec 12, 2018
Fetish

I awoke at 5am on a cold, Saturday morning. Dreaming of my sexy dentist all night made me feel so kinky. The thought of shagging Sian Harris made my cock have a permanent erection. I was surprised to hear the bell on my front door so early. I decided to open the door wearing my pretty, pink dressing gown. It was my cousin Susan Beynon aged 37. Her flaming, r...

FFQ Caption Collection

by ffq on Sep 15, 2020
Miscellaneous

I have written a variety of captions and posted them to BDSMLR over the past year. Recently, I decided that I would try sharing some of the captions here on CHYOA for people to write continuations or alternate branches if the captions catch their interest. These captions involve celebrities, historical figures, and original characters. The content most often...

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A Weekend Away Ch. 02

by SluttyChrissy on Sep 14, 2020
Transgender & Crossdressers

Author's Note: Thanks for all the kind feedback & comments on chapter 01. This chapter does a lot to set up the rest of the story, so there isn't a ton of sex. Please hang in there with me and there will be much more sex in the chapters 3-?? I hope this one is sexy enough to keep you interested! ---------------------------------------- I'm not sure how lon...

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...

Nun Pussy Ch. 05

by 80niner on Sep 26, 2017
Novels and Novellas

Even the next day, Rachael could not get over the fact that she had been strapped and strapped, most vigorousy on her tender, bare buns. More surprising, she found she enjoyed the naughty experience both in the weilding and the receiving of that narrow, leather strap. She had never known such excitement and exuded so much moisture in her loins as when The Go...

Trapped and Trained Ch. 02

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stocki...