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DO YOU WANT TO GO ON ANOTHER DATE? (fm:seduction, 7865 words)

Author: Caress
Added: Mar 07 2018Views / Reads: 1413 / 1095 [77%]Story vote: 9.62 (29 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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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.

But the best was whenever I'd be behind her talking, I could sometimes see down the front of her blouse. She was pretty small breasted, so often the bra was stiff enough to be open on the top. Once I had seen her entire little tittie sticking out firmly from her chest with the bra doing absolutely nothing. She didn't need it.

She was very much in charge in relationships and seemed intrigued by my totally different approach to life. It didn't take long before conversations turn to relationships. It was obvious she had a lot of boyfriends and was very experienced. And it soon became obvious that I had no experience whatsoever and was very awkward when it came to girls. I told her that the most I've never done just put my arm around the girl and that was pretty adventurous for me.

She was always trying to encourage me to ask out girls that I was attracted to. But I told her that since the kids in this school had been dating for four years already I just didn't know where to begin. She understood that it would be very difficult to be very confident when I didn't know what to do or how to initiate it. I didn't even know how to kiss.

I had seen some of the 'rougher' senior guys trying to come on to her and she knew how to handle herself. I think she appreciated that I didn't connect with her on some crude level like most of the guys in her life did.

I was tall and pretty good looking, and she said I shouldn't be depriving the girls. She said she knew lots of girls that would love to get a hold of me. I think that maybe got her thinking. She said she enjoyed a good time as much of the next gal, it could be fun to show a novice the ropes. She would love to be totally in charge for a change.

Probably more out of frustration than anything she said if I came over some afternoon after school she would show me some of the basics. But only if I only took directions from her and didn't do anything that she didn't tell me to do. She didn't need another guy in her life to fight off.

At age 18 it seemed like I was always one glance or one thought from having an erection. The direction of this conversation certainly had this undesired affect. I tried the best I could to hide the obvious but since shirts had to be tucked in there wasn't much I could do.

I told her it would be great if she could show me things. She said that she could see that it looked like I would be interested. Obviously that embarrassed me and I blushed. She said that she would show me what she enjoyed doing on a date and that she wasn't just a tease.

Of course that only made things worse and now I had a wet spot on the

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