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DO YOU WANT TO GO ON ANOTHER DATE?this story is part of the FanClub (fm:seduction, 7865 words)

Author: Caress
Added: Mar 07 2018Views / Reads: 1696 / 1301 [77%]Story vote: 9.63 (30 votes)
I was graduating high school and never dated. An older girl took pity on me and offered to show me a few things, but only if she was in charge.
 


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DO YOU WANT TO GO ON ANOTHER DATE?

I had just transferred into this large high school as a senior in the mid 1950s. I used to take lunch breaks in the stairwell where in the hall monitor sat. The school would hire graduates to be hall monitors. Rita was very attractive, but not very refined. Single mom in poor section of town...pretty, earthy and knowledgeable in the 'ways of the world'.

She was very petite, but carried herself more as a Tomboy. But she had to abide the dress code, so looked every way the 'lady'. Dress had to touch the floor when kneeling. She was way out of my league. I would definitely be too 'square' for her. But we became friendly after several months of sharing lunches together.

I had seen her outside of school a couple times and she dressed like a Tomboy. I had seen her in jeans that really accented her cute little boy butt. Her cheeks were really high and apart. You could see her firm little cheeks flex when she walked.

Every now and then I could see those sweet cheeks flex under some dress she'd be wearing to school. Her manners weren't very lady like, so other I could catch a glimpse up her dresses. For a teenage boy, that was pretty exciting.

...

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