
09-17-2013, 04:51 AM
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Junior Member
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Join Date: Sep 2013
Posts: 2
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Am I? You decide.
How I Experienced My first Orgasm at the Hand of our 16 yo Babysitter
The summer I was 11 years old, my parents went away on a trip together for a week, leaving my siblings and me in the care of a 16 yo live-in babysitter for the week (she was the daughter of an old acquaintance from about 40 miles away from our small home town). The first night she was there I peeked in the East window of my parent's bedroom, beside my parent's bed, and watched her undress to bra and panties and climb into bed. The next day I hid under my parent's bed while the baby sitter was taking a shower. She got called to the phone and came to answer it wrapped in a towel (the bedroom phone was just over my head, on top of the shelf in the headboard). I cautiously peeked out from under the bed and looked up inside the towel and discovered for my first time that women had pubic hair (in my very limited experience, the only other example I had to compare to, was my 9 yo sister with whom I had been playing doctor - lol). The baby sitter went back to finish her shower I and got away quickly (my original plan, or lack thereof, had not included an exit strategy - lol).
That evening I seduced the baby sitter into agreeing to let me join her in my parent's bed, half an hour after my siblings had gone to sleep, so I could see her bare breasts ( she had agreed to do this after I told her I had already seen her lower half - lol). After my younger sibs were asleep, I quietly went upstairs and climbed into the bed beside the baby sitter. who was in the middle of the bed with my 9 yo sister sleeping on the other side. Under the covers, the baby sitter was dressed only in bra and panties, like the previous evening. She rolled away from me presenting her back to me so I fumbled with the clasp on her bra, and finally got it undone. She rolled back and took off her bra and stowed it in the shelf in the headboard, but she would not let me turn on the reading lamp to see her bare breasts, because the teenage boys next door were playing basket ball on their driveway right outside the master bedroom window (where I had been peeping the night before).
She made me wait to turn on the light until the neighbors quit playing and went inside. While waiting I was fondling her bare breasts under the covers. Finally I got to fold down the covers and turn on the reading lamp on the headboard, and gaze at her full, round, bare breasts, areolas, and nipples for a minute or two (she was a bit chubby so her 16 yo breasts were nice and full).
After a couple minutes the light was turned off and the covers went back over her breasts, but I was there under the covers too, playing with her bare breasts for an hour or so before I went to bed and she put her bra back on.
The next day I tried to get her to let me see the full frontal package while she was wearing just her bathrobe prior to her daily shower. She would not let me open the robe, but I did get to reach inside it and fondle each breast, one after the other.
That night I again crawled into the bed beside her after everyone else was asleep and resumed fondling her breasts. I asked if I could suck her nipples and was granted permission. I had been bottle fed along with all my younger sibs, so this was the first time I had a woman's nipple in my mouth.
My hands ventured out over new territory, down her stomach and down below her waist to her panties where at first I felt the springy triangular mat of curly dark hair through the thin cotton fabric, and then my fingers were probing through the springy mat directly, inside her panties. I probed as far as I could reach and asked if it was too ticklish for her and she said it wasn't. She did not open up her legs so I was stopped short of reaching the opening down there.
We had discussed previously the extent of her experience with her teenage boyfriend back home (which was only some petting). I asked if she had ever touched a "grown" penis (not a baby's like when changing his diaper - mine was hardly thicker than a fat kindergarten pencil - lol). She answered that she had not, and I invited her to do so to mine, and she agreed. I lifted the stretchy waist-bands of my pj bottoms and white briefs (the full extent of my clothing) and she inserted her hand and wrapped her fingers around my turgid little shaft standing there at attention. It felt wonderful! She squeezed a little as she continued to hold my little dick, until I suggested she reach lower. I had intended for her to cup my balls and scrotum, but instead she just moved her hand to the base of my shaft, and then something unknown and amazing happened! She had only moved her hand down a little and squeezed the shaft a bit, but the sensations that exploded inside my penis and my head were surprising, amazing, wonderful, and a little frightening, No fluids came out that first time - not until about 6 months later when I learned about masturbation did I finally understand what those amazing sensations were that first time - at the hands of our 16 yo baby-sitter).
Epilog: Years later I somehow had occasion to relate this experience to my sister who had been right there but asleep throughout the whole experience, and asked her what she would have done, had she awakened and found her oldest brother fondling the baby sitter's bare breasts and probing around inside her panties, and my sister said she would probably have joined right in and we could have had an advanced class in comparative anatomy. lol
That was how I experienced my first orgasm at the hands of our 16 yo Babysitter.
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