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The Babysitter

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The Babysitter
My "thing" is the first touch of a new partner on my cock, and the first thrust into her mouth and pussy. Each new partner is a joy to experience, and that first, highly anticipated and desired contact never fails to bring a thrill.
This goes back to childhood: my first remembered sexual contact with another person was when I was about 6 or 7 years old. My family was visiting some friends at a cabin in the woods with a couple of other families. There were 5 or 6 kids, and we were chased outside to play as the cabin was small. We found a great spot near a small creek where there was a natural sandbar. The oldest kid, a girl about 10 years old, suggested we take off our clothes to go swimming. The water was very cold, and she never really had any intention of swimming - she just wanted us to get naked. There were 3 girls, but I was fascinated with the oldest one. She was very outgoing sexually, examining each of us closely and stroking herself. She handled the other boy (we were both hard), bringing moans from him as she felt his cock from one end to the other. She took his hand and put it on her pussy, grunting with pleasure as she used him to stroke herself. I was beside myself wanting her to do that to me. The other girls were just standing there naked, watching them just like I was, but it never occurred to me to ask one of them to touch me. Unfortunately, our parents caught us before she got to me, and I remember being upset not at getting caught (and punished), but at not having had the chance to feel her touch me.
Over the next couple of years I learned to masturbate and practiced it frequently, often using that incident as a masturbation fantasy. I managed to talk the girl across the street into taking off her pants for me one day, and we gradually escalated to completely undressing in the woods behind my house. We masturbated in front of each other each time, but I never could get her to agree to touch me or let me touch her. There was one other incident where a classmate (girl) asked me to come over to her house after school, and in her garage that day she pulled down her pants and asked me to do the same. Of course I immediately obliged, springing into erection almost immediately. We stood there looking at each other's genitals, with me stroking myself in ecstasy. She asked me if that felt good, and I said, "Yes, it's wonderful, don't you do it?" She said she did sometimes, and asked if I wanted her to do it to me. I practically jumped at the chance, and as she was reaching for my straining cock, her dad drove in the driveway. She quickly pulled up her pants and ran into the house, telling me to go home so we wouldn't get caught. Another missed opportunity and another masturbation fantasy.
Finally, when I was about 11, my parents left me and my siblings with a babysitter one night, and it happened to be the girl who had started the whole thing at the cabin in the woods. She was now about 14, and the most gorgeous female I could ever imagine seeing. She put my brother and sister to bed early and sat down to watch TV in the family room. I was in my room in pajamas (tops and bottoms), and nursing a raging hardon, remembering the cabin incident. I summoned up the courage to walk into the family room with my cock obviously tenting my pajama bottoms. She saw that right away and stared at my crotch as I walked up to her. I asked her if she remembered that day at the cabin, and at first she claimed to not know what I was talking about. But, she didn't take her eyes off my tent. She could clearly see it jump as it throbbed with my heartbeat. She finally 'remembered' the day, and smiled in spite of herself. I then asked her if she wanted to do it again, and she acted shocked, vehemently saying, "NO!" I was nearly devastated, as I was sure she wanted to do it as much as I did. But, my cock saved the day as it slipped out of my pajama fly at that point, springing into full view. I instinctively began to stroke it, and delayed putting it back because it felt so good. She stared at it for a few seconds and then said, "Well, OK, but don't tell anybody."
We went to my bedroom, where I quickly stripped off my pajamas and stood in front of her naked. I asked her if she was going to take off her clothes, and she responded by pulling her t-shirt over her head, revealing a white cotton bra that completely covered her small mounds. She reached behind and unsnapped the bra, letting it fall off her shoulders and tits, showing two small mounds with little, hard nipples. I was in heaven, my cock throbbing violently. I deliberately withheld stroking it as I knew I would not last, and I wanted this to go on forever. At that point in my masturbation evolution I was releasing my hold on my cock when my orgasm started, allowing it to complete without touching myself. I expected my cock to explode without ever being touched as I looked at her. She unzipped her jeans and, hooking her thumbs in the waistband, slid them down her long legs. She was wearing white cotton panties that went down with her jeans, and I saw a real, fur-covered pussy for the first time. Her pubic hair was light brown, sparse and looked to be soft down. It covered a triangle above her cleft, which was slightly open, showing just a peek at inner lips and some glistening moisture. What all that meant was lost on me, but I was just fascinated. I leaned forward and became aware for the first time in my life of the smell of an aroused woman (something I had experienced in my parents bedroom without knowing what it was).
She stepped out of her jeans and panties and started to stroke herself, like she had been doing back at the cabin years before. She asked me if I wanted to feel her, and I gushed out, "Yes!" She then asked if she could feel me, and I again said, "Yes!" She laid down on my bed on her back and guided my hand to her pussy, where I felt the wet heat for the first time. She moaned and closed her eyes as she guided my fingers back and forth just inside her pussy lips, getting them soaked with her juices. She guided them up to the top of her slit and whispered, "There. Right there. That's it. OH, OH, OH that feels so good!" In the mean time my cock was hammering to be stroked, obviously throbbing up and down. She opened her eyes and looked at it, still stroking herself with my fingers. She took her other hand and reached over to take my cock in her fingers, and my life changed forever. The shock as her hand closed around me was electric, the feeling indescribable. I have no idea how I managed to keep from coming immediately. She slowly started stroking it, and all I could think about was the incredible pleasure coming from my cock. I could feel the orgasm building slowly, and I knew it was going to be the best thing I'd ever felt. She asked me how it was, and I managed to stammer out, "Wonderful. I can't believe how good that feels!" She smiled and said it felt good to her too, and I realized that she was still stroking herself with my fingers. I started to become more aggressive with my hand in her pussy, and she took her hand away from mine, letting me stroke her. My own orgasm was now eminent, and I started to whimper. She asked me if I was OK and all I could do was nod my head as I gasped for breath. That set her off too, and she threw her head back and began to moan. I came first, great throbbing bursts of pleasure as she stroked my cock. I gasped, "OH" with each one, staring at her pussy with my hand in the middle stroking furiously, trying to bring her with me. She went rigid and starting gasping and mewing as her orgasm ripped through her. I finished first also, and panted as she finished hers, her hand still wrapped around my cock and my fingers in her drenched pussy lips.
I slowly stood up and gently continued stroking her pussy. She lay quiet for several seconds, her hand gently resting on my cock, which had not gone down. Suddenly she pulled her hand away and brushed my hand from her crotch, saying, "That was great, but we shouldn't have done it. Don't you dare ever tell anyone." She got up and quickly dressed facing away from me and left the room, glancing back at my nudity and slowly deflating cock as she closed the door.
That was the last time I was alone with her; she never worked as my babysitter again, and even though we saw each other occasionally, she never mentioned the incident again. It became my best masturbation fantasy, of course, and I soon began stroking throughout the orgasm, as she had.



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