Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

Mistress Morgan's Sissy Husband

by corduroysissy on Dec 10, 2017
Transsexuals & Crossdressers

Morgan Ashley was a very pretty lady, not movie star glamorous mind you, but far prettier than anything her wimpy husband Robin would normally attract. Having just stepped out of the shower she was wearing a red mid-wale corduroy bathrobe and her long red hair was wrapped in a towel. She was seated in the living room armchair with a cigarette perched between...

A Mistress to Obey Ch. 02

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm and gay play. Not your thing, move on. * I can't stop thinking about what happened last Saturday. It was so much more than I expected, and frankly, I did things I never thought I would do. I had fantasized about forced fem but still was surprised how different I felt when in panties. It's just hard to feel very masculine when in a...

Sandra and Stevie Ch. 58

by Goodhusband on Sep 19, 2017
Loving Wives

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

Madam Molly Pt. 02

by corduroysissy on Feb 11, 2019
Transgender & Crossdressers

Molly & Jessie's conversation lasted about twenty minutes, and by the time it was over she'd made it quite clear that when it came to obedience her expectation were very high. She then informed him he was going to be her little slave-boy and amuse her for a while. When she was ready to get laid she'd summon her cuck Tracy back and Jesse would resume his boyf...

Casey's Submissive Journey Pt. 10

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

Mistress Dorothy was rubbing her husband's bulge affectionately. "Julian honey, Casey was sniffing your pissy pants while you were doing your chores, and quite frankly hubby, I think he liked it. Maybe in the future I'll borrow him from his wife and make him be your bathroom bitch, would you like that dear?" "Yes Mistress very much. Can I be the boss of hi...

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...

Mistress Morgan's Sissy Husband Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Robin arrived home from work about 5:30 on Thursday, he still felt a little apprehensive about what happened Tuesday night with his sissy friend Patty, and he hoped he might get to talk about it with his wife Morgan. He really enjoyed wearing the corduroy skirt outfit she bought for him, and he loved being a sissy whore for his wife and Patrick, her "boyfrie...

Casey's Submissive Journey Pt. 15

by corduroysissy on Aug 28, 2018
Transsexuals & Crossdressers

When he walked into the playroom he saw Robin sitting in one of the chairs drinking a beer. Sonya turned around and pointed to the other chair. "Sit puto." Debbie did as told and his boner made a very obvious tent out of his skirt, it didn't bother him though because it matched Robin's pants. Sonya left without a word and Debbie picked up the drink on the...

Sandra and Stevie Ch. 59

by Goodhusband on Sep 19, 2017
Loving Wives

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

Sandra and Stevie Ch. 64

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the sixty-fourth installment in a series entitled "Sandra and Stevie". If you have not read the previous sixty-three 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 st...