Butt Plug Punishment Stories

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Webslut Madison Ch. 04

by Rockwellray0 on Sep 26, 2017
Exhibitionist & Voyeur

Madison went to bed satisfied after her escapade at the mall. She was still aroused when she got home, and she masturbated to another orgasm before bed, thinking about the activities of the day. It wasn't Madison's first time with a girl. She had experimented, and she had hooked up a couple of times and even considered dating another girl earlier in college...

An Office Memo Ch. 02

by saraceleste on Sep 11, 2017
BDSM

***This should stand alone on its own, but if you want to read more background, check out the first memo "An Office Memo" *** ***** MEMORANDUM To: Frank McCaffrey From: James Fields Re: Office Appraisals During Your Absence Frank, Here's hoping your trip went well and that you enjoyed the conference. I know how much of a pain it is to travel when...

First Submission Ch. 02

by Domfetish on Sep 17, 2017
BDSM

It has been five years since I penned part one of Submissive Awakenings, and posted it on various story sites. It has appeared here a couple of times as my account has changed, and the name of the subject was altered. Part One was not written as a story, but was an e-mail I sent to someone whilst they were at work. As she and I went our separate ways I have...

Baby Sister Ch. 12: HAPPY TrAILS

by SZENSEI on Sep 14, 2020
Exhibitionist & Voyeur

"Why has Aunt Harriet not come back to haunt me?" After a few days to process being fucked for the very first time Maria Blanco felt really alone. Even stepping back into her own bedroom for the first time in three days she found the courage to overcome her fear of the multitude of sexually active ghosts, having met quite a few the other night. Not real gho...

My First Anal Lesson

by Ginger_Sparkle on Jun 5, 2019
Anal

You demand I take my clothes off. You kiss me as you pull my shirt over my head. You lead me over to a chair & have me kneel down on it backwards. You secure my wrists to the back of the chair. You take the lube & drizzle a thin stream down the crack of my ass. With a sharp crack you smack one of my ass cheeks. I moan as you rub the red mark your hand left....

Life After Last Night

by JJ Neal on Sep 16, 2017
Transsexuals & Crossdressers

Giddy and gay I'm on my way to Jenny's house. My wife, Sheila, is out of town on one of her bi-monthly business conferences and for me that means a Saturday night date. My friend Jenny has a salon in her home and for a guy like me that is ideal. It's 9:00AM and I've been up and busy for three hours. I started a liquid diet Wednesday when I confirmed the da...

The Deal

by WJKennaugh on Sep 17, 2017
BDSM

The porn channel plays on the flat screen TV in your hotel suite, as you prepare to relax after successfully signing your company's biggest ever sale contract. Your head is warm and muzzy from a combination of 20 hours' continuous negotiations, and the glass or two of Pol Roger Cuvée Sir Winston Churchill (1996, in fact) you and your colleagues downed to cel...

Her Secret's Out Ch. 05

by LucyCanyon on Sep 12, 2017
BDSM

Dan and Tracey were, for the moment, sated. He had spanked her ass and fucked her whilst she was blindfolded, a plug filling her ass and her cheeks tortured and red, burning with the heat generated from his blows. The relationship had been agreed, after Dan had walked out leaving Tracey to fume and consider whether or not she wanted to submit to him regardle...

Friendly Favours Ch. 02

by Goey on Sep 25, 2017
Fetish

It had been a few weeks since my boyfriend, Tom, had become the "bull" for Jess and Steve's cuckold relationship. I had enjoyed watching him fuck her finding it more fun than I ever thought I would. I've known Jess for years, but the recent change of our relationship couldn't be more surprising. Yes, she was an open person, but I had always been reserved aro...

For Love Ch. 11

by Wonderlusting on Sep 15, 2017
Transsexuals & Crossdressers

Renee and I awoke in a couple of hours. True to her word, Ms. Ward had not bothered us. "Let's go take a look at your soon to be apartment." Renee seemed more excited then I was about starting to work at the condo. I pulled on my shorts, with Renee giving me a look that told me I would be commando, and the shirt I had worn here Friday. Renee put on a sma...