Sissy Butt Plug Stories

100,438 results
Orientation
Length
Source
Infinite Scroll

A Slave's Tale Ch. 03

by Steveweis2001 on May 13, 2020
BDSM

My first session with SIR had gone by so fast. I could hardly believe how quickly two hours could pass. I had trouble concentrating on the drive home. My mind was reeling! I felt so good and so different. The cock ring around my cock and balls was pulling slightly and I could feel the weight of it. My mind kept wandering back to when SIR put it on me. The...

Rekindling Old Passions Pt. 08

by SandyWhitlock on Oct 12, 2020
Loving Wives

GETTING READY Clara was nervous and excited for their dinner with Trent. She had that butterflies in the stomach feeling. She knew she would take Matt's lead no questions asked. Part of her earning Matt's trust back was agreeing to submit to every perverse request he made. Clara can't say she minded this arrangement. It made her wet to think about how she...

Gumdrop Ch. 09

by bushyTrail on Jun 25, 2019
Fetish

Author's note: As absurd as the concept of a hucow is, I tried to take it quite seriously, to delve in the psychology of a hucow and her owner, in search of what this admittedly strange fetish means, at least to me. Therefore, beside the tropes of the genre (kinky sex, humiliation and de-humanization), you will find the musings of a young girl who chooses t...

Good Morning India Ch. 04

by dan57 on Sep 14, 2017
Loving Wives

Fourth volume of Kira s adventures Kira is a mature but still very pretty French woman who had always been fascinated by India. At last, she had the opportunity to visit the country with her husband Dan. They were invited to an Indian wedding in a wealthy and influent family. They met there the Prince Kyrhan who decided to show Kira all the aspects of the l...

Stable Boy Ch. 08

by MissLisaJones on Sep 17, 2017
BDSM

And then, on Monday, it rained. It would seem that the weather was trying to make up for the previous spell of sunshine and, with the wind blowing briskly from the South-west, great banks of black clouds scudded overhead, each one bringing with it it's own downpour. Jim threw on a coat before setting off but, even so, he was drenched by the time he got to Ne...

An Unlikely Reunion 25 Years Later

by walterio on Sep 16, 2017
Mature

A CHANCE MEETING What were the chances that I would run into a woman that I had not seen for 25 years? This was just not any former acquaintance but a former Administrative Assistant with whom I had a five year affair. I was now 74 years old and I knew she was 62. Cathleen looked fantastic a she still had a firm body, great legs and a killer ass and I was p...

Ghost in the Machine Ch. 01

by Blind_Justice on Sep 12, 2017
Sci-Fi & Fantasy

Author's note: A huge "Thank You" to bikoukumori, for a fantastic editing job. Also, thanks to fellow author redskyes, for encouraging me to publish this. There are only adults in this story and no artificial intelligences have benn harmed in its making. #1: Cat killed Curiosity Rain. Nothing but rain for the last few weeks. Never before have I seen s...

The MILF Next Door Ch. 08

by Argonaut_1975 on Sep 24, 2019
Mature

Esther groaned as she pushed her body to the limit, muscles straining, rising and falling again and again. Exhausted from her exertions she nonetheless kept repeating her efforts until finally she could take no more. As her strength failed she was grateful that Stephen was there to catch her, the weight of the bar taken easily by his hands. The raven haire...

Movie Star Gone Astray Pt. 04

by TSNatasha on Apr 17, 2019
Transgender & Crossdressers

As I clocked out for the day, I practically ran to my car. Not only was I ready to get out of this dirty kitchen, I was running to see him. It had been two weeks since Dustin and I began our relationship by fucking on his living room couch, and I was in heaven. Every minute that I wasn't at work or doing something at home for my parents was spent looking as...

Making New Friends

by Biguy5774 on Apr 13, 2020
Group Sex

It was in the elevator that Jess really started to feel anxious. She took a deep breath as she started fidgeting with buttons on her mauve blouse and the hem of her tight black miniskirt. James noticed it right away. He looked down at her and gave her a warm, sympathetic smile. "Nervous, babe?" Jess awkwardly returned his smile. "Yeah, just a little maybe."...