Sissy Maid Stories

19,946 results
Orientation
Length
Source
Infinite Scroll

Maid for Cum

by slcmalemaid on Aug 18, 2017
Fetish

The first thing one notices is the spent condom. This would normally be a very odd thing on a kitchen counter. However, I am not only not surprised, but I expect it. Next to the condom is a list of cleaning chores. And there I am, alone in a slutty french maids uniform getting ready to clean the house. How did this turn of events happen? Well, one night, a...

Intervention

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

My fiancée's girlfriends were becoming a little apprehensive about the changes Angel was exhibiting since we had started dating. They had noticed her attire had become much more suggestive, and her make up more severe. There were other changes too. She was now sporting a tattoo on her right shoulder, an angel/mermaid holding a heart with my name on it. Sh...

Eating Cum for Her

by DarlenesToy on Sep 17, 2018
Loving Wives

My wife/Mistress directs me to write these stories for her and then we do them in reality. She always takes parts of my story but changes the reality to suit her needs. This was a story about eating another man's cum. It started innocently enough. You were allowing me to jerk off and lick my precum off your nipples like normal. Then you began whispering as...

The Writer's Secret Ch. 09-10

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 9: Laura's Mall Odyssey Loren was sweating bullets by the time Stephanie finally parked the car. He expected they would go home. They hadn't. Instead, they were parked outside Raycine's, a department store at one end of the Valleyview Mall. The mall was only five miles from their house and they shopped here occasionally. "I can't go in there." "Yo...

Sissy Awakening Ch. 03

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- Sissy Meets Sarah's Bull - Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these! She said to wash inside and out, and not to miss a spot. That meant...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Devoted Cuck Ch. 02

by cuckyfucky on Dec 18, 2018
Fetish

This is Chapter 2 of my ongoing series. Chapter 1 can be found in my profile. ***** I was cleaning the kitchen in my sissy maid outfit when the phone rang. Seeing it was Lina, my wife, I immediately picked it up. "Hi cucky, are you finished with your chores?" she asked. I could hear music in the background and so I knew she was still at the club. "Yes L...

The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

Sarah Shows Off Her New Panties

by SarahCD on Dec 12, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. *** I was posting a picture of me wearing black ruffled panties on a "Men in Panties" website when I remembered something naughty th...

Goddess Monica's Beta Bitches h. 01

by DonGarciaWallaceIII on Sep 12, 2017
BDSM

Meeting Gustavo Monica Garza's austere, coprolite-like walls, covered with aquarelles of men in tutus and women's swimwear, are sound-proof, and Gustavo must intuit or presume this since, once inside, his voice climbs in pitch in a way it wouldn't in any other of her condo's rooms. In the little kitchen, for instance, he nearly whispered. The tutu- and wome...