Sissy Maid Husband Stories

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Bootlicker

by GoddessVictoria on Sep 25, 2017
BDSM

BE CAREFUL WHAT YOU WISH FOR. He remembered that later, much later but by then it was too late. By then every semblance of masculinity had been totally stripped away from him. He was no longer master in his own home. How could he have been so foolish? Had there been a part of him that hoped she would find out? He had been so careful, smug even. Why shouldn...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

Appointment by Card Only Ch. 06

by Sputnik57 on Sep 17, 2017
BDSM

His landlord was not best pleased when Bruce announced his immediate departure, but was happy to hand him a bill requesting three months rent in lieu of his vacation without notice. He packed his laptop and the few items of decent clothing and sparse possessions into a sports bag and slung it into his car, then drove back to the house, his mind racing; he co...

From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...

Owned by my Mother-in-Law Ch. 04

by Sputnik57 on Sep 13, 2017
BDSM

The area by the window had a padded surface; no doubt Blanche's departed husband and many other enslaved men had been made to kneel for hours at this window, whilst they contemplated their fate on just such an evening as this. The padding would not be for their comfort, it would be there to ensure that their knees functioned when the time came to entertain....

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

Sissy Life Pt. 04

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I stood to attention on my 'sissy spot', the small 'x' drawn on the floor of my Mistress' study. My spot faces the desk behind which is a large leather chair. It is here that I was told I would be placed in chastity. It was here on my spot that events unfolded leading me to serve my Mistress' lover Tony. I was understandably nervous about being stood here ag...

Becoming a Sissy Maid & Slut Vol. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eighteen: Some New Friends for Chantel. A blissful night's sleep has led me to a wonderful Sunday day off. Master has told me I must accept that special Sunday plans are on the go after 3:00pm but today, this morning awaking at 9:00am I run my routine, enema, shower, put on fragrant body lotion. I then begin a day of dressing just for myself, but al...

Creating Ginger Ch. 09

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~ To say ginger was in hell would be an understatement, although it would be more accur...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...