Sissy First Time Anal Stories

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A Little Twist Over the Road

by mdw_dark_angel on Sep 17, 2017
BDSM

Master is an OTR driver for a national corporation. That could make things very difficult for O/our relationship as W/we would not be able to see Him very often, for very long at a time, except that - sissy, affectionately known as pet, and angel, referring to this girl - are His relief drivers. W/we travel with Him everywhere so it makes life a bit more exc...

Trophy Husband

by Alluring_Crimson_Shifter on Sep 28, 2020
Exhibitionist & Voyeur

Cherry kissed and gave Jeffrey a hug, "Let me know how your fitting goes with the tailor today. He has some lovely ideas for you." She gave a pat to his firm bottom and watched it as he turned and walked to the door. Cherry insisted her husband get fitted for a new wardrobe. They were newlyweds and absurdly in love. Cherry is a business woman and dresses at...

For Two Dollars More Confession

by Alluring_Crimson_Shifter on Jan 16, 2019
Anal

Ricky looked at his Sarah's panty clad tight ass as she rolled over on her stomach and cocked a knee up in her sleep. Her panties just form fitted her ass crack. Her gorgeous crotch was in perfect form and a few wisps of pubic hair tufted from the edges of her panty bands as a tempting advertisement. There was just a little crease where her pussy crack was a...

Exotic Pussy Cum Extortion

by Alluring_Crimson_Shifter on Sep 14, 2017
Anal

Leon struggled in his science class and was almost giving up at the idea of graduating from high school. As an 18 year old he did not see good prospects as an adult. His teacher coached him and encouraged him. She was his science teacher and sometimes spent time after class helping him with his studies. He admired her intelligence and her looks, and grew fon...

Entangled

by Todd172 on Aug 27, 2018
Loving Wives

Okay. Every so often I have to do something different. This one is pretty twisted. It is not part of any of my series, it is completely stand alone. Unlike most of my stories, it has some very graphic, very warped, freaky, fetish-y sex. Not necessarily in a good way. I apologize in advance for the Teddy Bear. Really. Thanks to blackrandi and sbrooks103X for...

Dual Use Building Retail Strip

by Alluring_Crimson_Shifter on Dec 24, 2019
Anal

Nancy was recently separated. She had to start a new life and was busy getting an affordable place to stay, and a new job. She stood in front of the mirror getting ready for work. She was a hair stylist, and she loved her silky brunette hair. She looked at the frontal view of her panties and loved how good her pussy looked. "Hello good looking," she said to...

A Gift in Disguise Ch. 09

by Talespin on Sep 14, 2017
Novels and Novellas

Who in his right mind calls me on the phone at 7 a.m. on Sunday unless it's an emergency? "Hello." My greeting to whomever was calling was not exactly warm and fuzzy, but neither was it in-your-face hostile. After all, it could have been my mother. "Tom, hi. It's Kim. I'm at the airport. Did I wake you up?" I wanted to sound more civilized. Really, I did,...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

First Contact: Into the Arena

by ShelbyDawn57 on Oct 19, 2020
Sci-Fi & Fantasy

Chapter 2, Rider, and the crew of the Phoenix begin their journey to Trellis, finding the warrior society of Diraki in their way. Unintentionally offending a local chieftain, Rider fights for her crew. Not as much sex as the first installment, but I think you'll like what is here. A few good fights, too. As always, please let me know what you think, your co...

The Sexy Cuckold Couple Pt. 14

by cuckcpl4play on Sep 26, 2017
Fetish

Part 14 Pool I As we departed the room, I was utterly shocked that Master was in fact going to make us walk through the hotel as we were. He walked with his slut in front and I brought up the rear, but following closely in tow. I kept my head down but could feel the stares and after walking by a large group I heard the individuals bellowing at our predicame...