MediumSissy Dating. It takes a lot more time, to get ready… | by Sloop John B | Medium
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Sloop John B

Sloop John B

Loving and Caring human being accepts all as they see themselves. Love writing, short quick stories of things I might have done and of people I have known.

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Sissy Dating

3 min readApr 21, 2026

It takes a lot more time, to get ready for a date as a girl, than it does for the boy. Throw on some jeans and a shirt or a T and voila with a swipe of deodorant and a splash of after shave, you are READY!

As the girl, so many things need to be considered when meeting with men for a date.

  1. What clothes do I wear for him based on where we are going, and what clothes will he want to take off?

Casual or dressy, does it provide that accessibility?

2. What lipstick do I want to wear with that outfit, and will it look good on his cock?My lips plump, but should I be subtle and a soft pink, promises perhaps or should I go deep red, stating I suck cock and willsuck yours, if I choose.

3. Fishnets or sheer stockings, how silky as he spreads my legs and explore up my thighs?

3B. Which heels do I want to wrap around his torso or put over his shoulders as he penetrates me and pumps me full of his cum?

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Sloop John B
Sloop John B

Written by Sloop John B

Loving and Caring human being accepts all as they see themselves. Love writing, short quick stories of things I might have done and of people I have known.