Sissy Butt Plug Stories

100,438 results
Orientation
Length
Source
Infinite Scroll

My First Threesome Ch. 02

by cdleesa on Sep 19, 2017
Group Sex

Rob took the ball gag and said, "If you enjoyed that, wait for the kinky stuff to begin..." I must have looked a cross between confused and despairing as Clare made a face you make to a puppy that's heard the door bell for the first time. "Awww, look at his face. He hasn't got a clue what's going on." She spoke to me in a cutey-pie voice, "There, there li...

Lost Phone Ch. 04

by flictus on Mar 12, 2019
Transgender & Crossdressers

As we sped out of my driveway with really only my passport and borrowed clothes my sense of adventure had peaked. I was about to embark on a life changing journey. One that even my wife seemed to approve of. One that would have me sporting breast implants to fill a roll as a pharmaceuticals sales rep. Once were out of the driveway Steve turned on the radio,...

To Love and Be Loved Ch. 01

by NerdySex on Sep 19, 2017
Novels and Novellas

This is a short novel in five chapters. It is a romantic novel but don't worry, plenty of sex. It should be read in sequence. I hope you find it interesting and worthy of your time. * The spread in People magazine was nice to see. Good for business. But I'm ahead of myself. Way ahead. Let me go back a dozen years. If you had seen me in high school you woul...

A Weekend Together Ch. 02

by maidashley70 on Sep 14, 2017
Transsexuals & Crossdressers

The next day we were awoken by the phone ringing, it was Ben asking us to meet him at a restaurant on the beach at 5. I told him we would be there and couldn't wait to see him again. We got up and stripped down to get in the shower, we took off my boobs and she unlocked my cage saying if I touched it a single time she would put the cage back on and It wouldn...

Going to the Bar

by fnchristie81 on Aug 7, 2018
Loving Wives

I was enjoying a lazy day at home when my husband called me up. He asked if I was up to going out to the bar that night, and maybe spending the night. Since both of us had been working an insane amount for the last year almost, I jumped at the chance. Late in the afternoon, I started driving towards the town we were going to spend the night in. I was dress...

The Weekend Ch. 02

by andymckink on Sep 19, 2017
BDSM

He stood in front of her, a strange look on his face. She tried to fathom it: certainly there was sadness there, concern, but also eagerness... looking down, she knew also that he was deeply excited by the prospect. "I am not sure about this darling," he said, seriously. "I had intended punishing you a little, and teaching you many things, but I know that y...

Master Ron & slave kim Ch. 02

by DMaster_14 on Sep 11, 2017
BDSM

Kim awoke the next morning to find herself still in Ron's arms. Smiling at the memories of the previous night Kim slid quietly out of bed and headed for the bathroom. The large en-suite was magnificent, the shower would hold five people easily and the Jacuzzi tub was big enough for four. The dual sinks were mounted in a granite counter and the rest of the ba...

Derek's First Encounter Ch. 02

by Miss-J on Sep 15, 2017
BDSM

This is a continuation of "Derek’s First Encounter" If you have not read the first story I recommend doing so before reading this chapter... Thank you to my readers, and I hope you enjoy this one, as much as the last. * * * * * As Derek packs, he thinks about the conversation he had with Miss J. He wonders to himself, will she make him stay naked all the...

The First Assignment

by _lisa_ on Sep 13, 2017
BDSM

I have been asked, no, told, to write a story for the man I wish to have take me as a lover. I cannot, and will not, disappoint him, and myself. I will do what he (in truth) asks of me, and feel honored as I serve him. He flatters me by requiring that I cast the two of us into the fantasies. I feel that it will be an act of intimacy and devotion on my part...

Her Visit

by diamondsubdarling on Sep 17, 2017
BDSM

She had been planning this trip for a long time, with much anticipation. The day has finally arrived and she excitedly boarded the plane to go for her visit, to see her lover. To her surprise I don't go to pick her up; you go instead. You ask her, "Are you ready for this weekend?" She is intrigued and curious, "what do you mean?" With a smirk you repl...