Crossdressing Maid Stories

15,364 results
Orientation
Length
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Infinite Scroll

Losing It All

by hambo on Sep 6, 2018
Fantasy

A series of smutty fantasy stories involving important and powerful people who end up in strange, embarrassing (and hopefully sexy) situations that often leave them naked and humiliated. Read about haughty knights who get taken down a few pegs when their quests don't go as planned, merchants who make bad business decisions, and wizards who don't quite manage...

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My Roommate, Brian

by OptimusCrime on Sep 26, 2017
Transsexuals & Crossdressers

I stood in the middle of my room, frozen in shock and total disarray. On the other side of the doorway stood my roommate Brian, staring at me in disbelief. It wasn't a very confusing situation, and not many excuses I could come up with. I had my boxers around my ankles, and my lotion covered hand wrapped around my dick. Well, not much of my dick was showing....

Mistress Chantel, Tranny Dominatrix Ch. 03

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three: My Saturday Meeting with Kerri. Well another busy but fun week for myself as Mistress Chantel begins to wrap up. It's a bright, sunny Saturday morning about 7:30am. My typical femme routine is to shower, dry off, moisturize with fragrant, moisturizing cream then to shave my face. Luckily for me in recent months I have begun to use a beard ret...

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Pearl Ch. 02

by allourdesires on Oct 22, 2019
Transgender & Crossdressers

The fact that Her boyfriend would be coming over to my flat, on the evening of my birthday, to bring Lori out was enough, of itself, to overshadow my whole week but, add in the fact that she had told him all about my crossdressing and our relationship and I would have spent the entire week cowering in my room! I think Lori realised that her actions had inst...

NaNoWriMo 2020: Chyoa Edition

by grimbous on Oct 31, 2020
Miscellaneous

November is fast approaching which means NaNoWriMo season will soon be upon us. For those that don't know about it NaNoWriMo (National Novel Writing Month) is a creative writing challenge whereby a writer tries to write a 50,000+ word novel in the month of November. Our challenge here will be a different one but in the same spirit of encouraging writing and...

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Obey Thy Neighbor Ch. 02

by jealouscuck on Sep 25, 2018
Transsexuals & Crossdressers

In the first few weeks after Li had discovered my crossdressing fetish, I worried constantly about her changing her mind and telling my wife about my activities. However, the more time I spent with her, the more confident I became that she was genuine. Since Li's husband, Ronald, was hardly ever around we were in very little danger. Even if my wife, Chelsea,...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

Becoming a Sissy Maid & Slut Vol. 04

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Preview: Here is another chapter of my multi-part "Becoming a Sissy Maid & Slut Story." I so hope you all are enjoying this story. I'm no professional writer so excuse me for any writing errors. But I have a flood of sissy maid, slut, crossdressing ideas, thoughts and fantasies to share. I will add more chapters to this unfolding multi-part story now ONE cha...