Literotica Giving Maid An Enema Stories

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Melissa Learns to Dress Properly

by stacey_lynne on Aug 18, 2017
Fetish

All Melissa knew was that she had been rented for the weekend. She arrived not knowing what to expect, much less what was expected of her. All she had been told was that she had commanded a generous fee and that she should behave accordingly. Her entire body had quivered all week in anxious apprehension of what was in store for her. When the day arrived and...

Sissy Chantel, New Reality Ch. 02

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Two: If One was Fun, Two will be Better. Late night I get a call and I look to see that it is my new Master. I answer, "Hello Master Camron, how may I help you?" "Bitch ass sissy, I am gonna need you here tomorrow morning, by 10:00am." he excitedly replies. I reply, "Oh, ok I guess I can make it to your home tomorrow morning Master." "You God Dam...

Two Days with Ulrike

by boyish_and_obedient on Sep 25, 2017
BDSM

When I was in high school there was a girl in my graduating class that I had such a huge crush on. Her name was Ulrike Lagerström. She had a body like a runway model and her long, blonde hair framed her innocent looking face in an artistic way that haunted my dreams. She had long sexy legs and a firm, tiny ass that looked great in her tight jeans. Her waist...

Jenny's Total Service

by slutty_jannelle on Sep 15, 2017
Transsexuals & Crossdressers

The cheap hotel carpeting prickled her legs through the sheer black nylons as jenny knelt by the door. Although she and Master Robert had met like this before, she always felt a twinge of apprehension while she waited for Him to arrive. Would He show up? Would she be abandoned? Would she ever see Him again? The questions swirled in her blonde head, conjuring...

Simon's Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Simon’s Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Of Lords and Ladies Ch. 07

by peachesmelba on Sep 18, 2017
BDSM

As Ronald inspected the equipment Mansfield was displaying for him he was surprised to feel Allyson quivering atop him. Thinking perhaps that she was cold he instructed Molly to stir up the fire and add some wood but Allys forestalled him by reaching out to delicately stroke one of the shiny ebony dilators. "These are pretty my Lo...Ronald," she corrected...

Sex School of Slaves for Girls Ch. 01

by schoolofsex on Sep 12, 2017
BDSM

The new slaves were lined up in the gym for an assembly. There were about 50 of slaves, 25 which was categorized as whores (women who enjoy sex or the idea of it) and 25 were soon-to-be whores (women who doesn't enjoy sex or the idea of it, they are here to be trained to become whores and slaves). The whores were in blue collar, while the others were in red....

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...