Cuckold Sissy Maid Stories

25,992 results
Orientation
Length
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Infinite Scroll

Being a Sissy for Viv Ch. 06

by Caron on Oct 31, 2017
Transsexuals & Crossdressers

Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

The Party

by Quietoldie on Jan 22, 2019
Fetish

Don't read this story if you don't like scenes in which men are forced and degraded without their permission by dominant women. ***** "Mike, there's a party Saturday night and this time you're coming with me." "It's not one of your office parties is it Gwen?" "No, it's round at my friend Christine's house. There'll be one or two surprises but you never k...

First Time Cuckold Ch. 03

by Angelscuck on Sep 14, 2017
BDSM

Maybe it was because I was fucking Jordi in my husband and my marital bed. Maybe it was because Oscar was in the guest room next to us and could hear every sound we made. Or just maybe it was because I was falling deeper and deeper under Jordi's spell. I'm not sure but our fucking tonight was even better than the first time. I lost track of how many times...

No Choice

by AZgirlMichelle on Sep 16, 2017
Transsexuals & Crossdressers

You act as if this is news to you. I'm surprised that you would even question the fact. This isn't a bedroom game. It never was. I have a plan and you WILL follow it. Choice? What choice? Whatever gave you the idea you had a choice? I told you that things would change if you wanted to live with me. I told you it was my way or the highway. And what did you s...

Sissy Chantel, New Reality Ch. 10

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten: My First Saturday and Sunday as They are Special Days For Us. "Wake up girls." as sissy Traci calls out to us. We all rise from our sleep and another day in our sissy maids, sissy sluts lives begins. Just like in the previous days starts we spend our time with a morning enema, shower, shave and makeup. We get dressed but not in any maids out...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

Discussion with a Wife of a Cuck Ch. 04

by wantyou on Sep 16, 2017
Loving Wives

1/26 E-mails This chapter starts out with me answering Alice's question. I wrote: First my answers to your questions! Alice wrote: The story is fine, but you have not included anything about what I have told you so far. I will as the story moves move and more into your meeting and the sex and then afterwards when you start to see Tyrome. I answered: I...