Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

Mistress Sylvia Pt. 01

by corduroysissy on Dec 18, 2018
Transgender & Crossdressers

Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergen...

Mistress Kate Pt. 03

by corduroysissy on Mar 14, 2018
Transsexuals & Crossdressers

Jordan was in a daze. He was dressed in full drag with his face made up pretty and the feeling of sissy submission was wonderful, he hadn't felt it in a long time. Everything he'd experienced since ringing Kate's doorbell excited him tremendously, and even though her demand that he be a cock whore for all her slaves was disconcerting, he felt thrilled to be...

Robin and Jimmy Olsen - Sissies Ch. 02

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Chapter 2 Robin prepares, Alfred beware! The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled...

Louis Makes a Decision Ch. 05

by Goodhusband on Sep 19, 2017
BDSM

Note: This story is the fifth episode in a short series entitled "Louis Makes a Decision". If you have not read the previous four 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 strongly...

Casey's Submissive Journey Pt. 01

by corduroysissy on Dec 14, 2017
BDSM

Karen walked into the bedroom and Casey thought he would have a heart attack. He was reading a book in the corner chair and looked up at his lovely wife. She was wearing a pair of dark red, mid-wale corduroy jeans. Casey had a corduroy fetish, corduroy turned him on a lot. He'd purchased many pairs of corduroys for her over the years and she knew the red o...

Down The Path Ch. 03

by gbr2004 on Sep 14, 2017
Fetish

This story involves gay sex and forced fem, not your thing, move to another story. * I haven't been able to concentrate all day, didn't get anything done. All I can think about is having to go back to the bookstore tonight. I don't know if I can do it but if I don't I'm not sure what he might do. Maybe he just won't contact me anymore and I really don't w...

Sandra and Stevie Ch. 60

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the sixtieth installment in a series entitled "Sandra and Stevie". If you have not read the previous fifty-nine 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 strongl...

Sandra and Stevie Ch. 46

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-sixth installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-five 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 stro...

Sandra and Stevie Ch. 72

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the seventy-second episode in a series entitled "Sandra and Stevie". If you have not read the previous seventy-one 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 stro...

Laboratory Fun

by Hypnoticus on Sep 26, 2017
Science Fiction

You stand on a street-corner in your home town. The sky is overcast and there's a rumble of thunder in the distance that reverberates off the buildings. You reach in your pocket and pull out enough cash to cover the cost of lunch, shove it into the hands of the street vendor, and begin to make your way back to the office. You would hate to be caught in yet a...

Open in Reader