Fisting Punishment Stories

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Infinite Scroll

Sarah's Second Encounter

by Player One on Sep 15, 2017
BDSM

It was a beautiful day out with sunny blue skies and little wispy clouds here and there. The temperature was in the upper 70's as we drove down a long straight road lined with trees, which caused a strobe light affect as the sunlight came through each space between each tree. The trip to my apartment was about 12 miles and most of the roads we would be takin...

CD Asst. Secy. Ch. 06.2: New Piercing

by cdtycoon on Oct 6, 2020
Transgender & Crossdressers

First of all, all the characters in this story are above 18. Also, it is the second part of my last story in this series. So, enjoy and keep reading. MADE TO SUBMIT Full submission as I was made to submit; ah.. almost; let's say about 90% from the next morning. You want to know why, well... The next day, 10th January 2021, I woke at my daily time of 5 a...

World of Possibilities

by stretchingfiction on Mar 1, 2021
Fantasy

So my story begins when I was exploring an old antique shop on the west coast. It was one of those disorganized and dirty older shops. With the dust thick in places and cobwebs clinging to everything out of reach. Had mostly seen the usual junk when an old trunk caught my eye. After haggling with the old shop owner I was able to get him down to 50 and he jus...

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Webcam Mistakes

by chrissycockslut on Apr 3, 2019
Transgender & Crossdressers

I guess I should've been more careful. But what can I say? I was a young man and I was stupid. I had just passed my 18th birthday a month earlier and I had treated myself to my very first, brand new dildo. Nothing crazy, only 5 or 6 inches long and just 1.5 inches girth with a suction cup base, but it was perfect for a beginner. Luckily, I had plenty of ti...

The Dinner Party: Party Favors

by ohophelia on Oct 15, 2017
BDSM

The masked partygoers were once again becoming restless. Andrea, the red-headed slave that had provided two hours worth of entertainment in her punishment, had long since been unbound from the table and whisked away to be cleaned and cared for. Without entertainment to distract them, and having already eaten their fill of the decadent treats carried on sil...

Fisting Cheryl

by Ravisher71 on Sep 26, 2017
BDSM

First impressions whether they be online or in person are not always accurate. I had posted online a thoroughly debauched tale of fisting and stretching – one of many. It is always good to get feedback and I often get asked if the stories are real or 100% fiction. The answer is a mix of the two. One of the stories elicited a response along those lines from a...

Weekend with Elaine Ch. 06

by clarepanties on Sep 26, 2017
Transsexuals & Crossdressers

I was left, naked, there for some ten minutes or so. And then the door opened. I was amazed by what (who?) entered the room. There were two women completely encased in baby pink latex with vertical white piping on the seams, complete to the point their heads were even covered. Now, I have worn latex before (at my ex's want), but this was something new. The...

Teaching the Teacher

by MaddieJCarter on Sep 18, 2017
Group Sex

Christian sat in the back of the class, his eyes glued to the back of his teacher's skirt. She wasn't really his teacher, just a substitute. Every once in a while one of his normal teachers would be out sick, or take a personal day, and nine times out of ten he'd walk into the classroom and there would be Miss Anderson. Sometimes one of his buddies would hav...

Sex at School? Naturally...

by MrsJ on Jan 13, 2018
First Time

Hello, I'm delighted you're interested to learn about my high school days, which have just finished – my recollections of a young girl learning the real meaning of 'life,' discovering those innocent teenage joys of sexual pleasure, losing my virginity, and leaving school very 'sexually active.' The school I attended is a private school, hours and hours awa...

Slut's Weekend

by MasterGirth on Sep 17, 2017
BDSM

Waiting at the booth in the back of the restaurant, Snowdrop checked her watch. It wasn't that Master Girth was late, rather that Snowdrop was dying to see him. They had both been so busy lately, so much had been going on in their lives, and they just hadn't been able to get together. Snowdrop took a sip of her Tia Maria and Coke. The waitress appeared, "Can...