Sissy Babysitter Stories

9,467 results
Orientation
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Infinite Scroll

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...

The Ethical Slutmaker Ch. 10

by KrisCherita on Sep 14, 2017
Anal

Chapter 10 A Perfect Bottom Dan read through the email a second time, glad that he had a private office and could hide the tent in his pants under his desk, and wishing Andrea had tagged the text NSFW. "Dear Tammi and Dan "Robyn enjoyed babysitting for you last week, and hopes you enjoyed your evening out. She's now decided that she likes and trusts you...

Babysitter horror

by Jeriah on Nov 21, 2009
Fantasy

You climb off the bus after about forty minutes from leaving your hometown, the driver ensuring you that this is the adress you wanted to go to. Finding yourself in the middle of nowhere, surrounded on all sides by the deep forest, you watch with sinking heart as the bus speed off into the distance. As you look up and down the lowly trafficed old road (if us...

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Living in Paradise: A Choose Your Own Tale

by fethishboy on Jan 17, 2007
Fetish

You turned legal not too long ago and are surrounded by hot MILFs and Cougars of many variaties. You're still a virgin and It's time to change it. There are women of different ages and creed. This is because not a lot of men surprisinglt live in this town and something about the water here breeds many well-endowed women. Most of which, older than you. It's u...

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Sue Storm's Cliche Life

by extreme1000 on Jul 13, 2020
Fan Fiction

Sue Storm was annoyed. Reed was, as usual, so busy with this science stuff that he barely knew she was there. Ben and Johnny were, she was pretty sure, turning into Itchy and Scratchy. So she was stuck taking care of her kids and waiting for the next villain to attack. She had to blow off some steam and quick. Luckily for her, she new the exact person to get...

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The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

Sara the Bad Babysitter

by rutger5 on Sep 12, 2017
Group Sex

Story contains coercion and reluctance. ***** Mr. and Mrs. Crudele were going to have a much needed night out. Since the arrival of their little bundle of joy four months earlier they hadn't had a night out together. In fact they rarely had a few consecutive hours sleep in a row. But that night they had plans for a quick supper followed by an evening at th...

A Visit By Renee, At The Local Bar

by stoneypoint on Sep 14, 2017
Romance

Renee's husband stopped over Saturday afternoon to invite me for a drink at Jets Bar and Grill. My first thought was to decline his offer, but I have already done that three times to him, so I accepted. I kept thinking about that one day Renee stopped over and we cuddled on my bed after she read two stories I had written about her and I. All I could think...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...