Sissy Plug Stories

24,564 results
Orientation
Length
Source
Infinite Scroll

Mowing the Lawn

by ultramannc on Mar 23, 2020
Loving Wives

July in the south is HOT, HUMID and NASTY! Yes July is all of these things and with the right wind you can increase your torment 30 fold. Mowing the lawn was not something I ever wished to do. My husband used to take this task on so I would not have to burden myself. Since his death these tasks fell to me. Up to this point, most of the tasks have been rela...

The Osaka Riders of Glorious Youth Pt. 01

by Vincent21 on Apr 15, 2020
Group Sex

Every spring I take the ferry from Osaka to Tokushima to let loose my Ducati Hyperstrada on the winding mountain roads of Shikoku. I look forward to this trip all year. It's pure me time. The roads of Shikoku are kept in excellent condition as a way to support rural communities, even though very few cars use them. The scenery they travel through is stunningl...

Afro Stress Relief Ch. 01

by llts1970 on Apr 10, 2018
Transsexuals & Crossdressers

My first initiation into the liberal culture of improving the Afro-american male integration into society through stress relief programmes such as AMIRAP and the strident feminist-driven attitudes of advancing minorities within society at the expense of the mainstream culture was in early 2000s. I was in my early-20s living in Oklahoma City, let's just say...

Mistress Marisa's Estate Pt. 31

by keptsissy on Sep 15, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** She starts to walk passed me but stops. I curtsy as she enters your home. She suddenly turns to me, the front door still o...

Sandra and Stevie Ch. 47

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-seventh installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-six episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I str...

Our Steven, Our Stephanie Ch. 01

by Johnboy9 on Sep 13, 2017
Transsexuals & Crossdressers

This is the start of my second submission here on Literotica, or anywhere else, for that matter. I am pleased with the positive response I received for the first story, and I only hope you all enjoy this story as much. * Steven had just gotten home from school, hanging his coat up on the coat rack when his Mother had turned into the hallway coming up from...

Owned by my Mother-in-Law Ch. 09

by Sputnik57 on Sep 13, 2017
BDSM

Next Morning the ladies were delighted when the doorbell rang as the sissy and I were tidying up the breakfast things. Miranda was supervising my filling of the dishwasher as Blanche came through in her dressing gown with several 'next day delivery' parcels which had arrived. I was taken into the lounge and made to try on my new clothes. Every item was a bla...

Grammar

by Nils Huim on Apr 11, 2018
BDSM

I sat at the foot of the bed, about four feet south of the wetspot. I had not made the wetspot, our new Dom had. He'd promised my wife Joy ("the Joy of Sex," as he laughingly called her) a big load and he hadn't lied. In grey shape it reminded me a little of the state of South Carolina. Joy had wiped her vagina afterwards and then tossed the tissues on the b...

Sissy's Sexy Strut

by nancyvasquez on Aug 28, 2018
Transsexuals & Crossdressers

Last night kicked off the Labor Day Weekend, so I decided to do something daring -AND, very sexy, too! I was looking at myself in the mirror yesterday afternoon & checking out the effects of the beating I got from Mike the other night. My eye is still pretty much closed, and now it's all purpled. My upper lip is still puffed out too, but I think it looks dam...

Anonymous

by KingBandor on Sep 11, 2018
Loving Wives

George stared at the glowing computer screen from the depths of his dimly-lit "man cave", as he called it. In reality, it was the basement of his mother's house, where he spent most of his spare time. It was very cave-like, being dark, damp and smelling of moldy things growing. There was little that would be considered manly about it. It had a furnace in on...