1. Remebring my first Babysitter


    Date: 12/22/2014, Categories: First Time, Masturbation, Taboo, Author: brianbigdogsmith, Rating: 100, Source: xHamster

    member. I basked in the warmth of my first cum (dry cum, actually; I didn't ejaculate until I was a freshman in high school) with her arm around me, softly holding my limp little dick. Much to my amazement, about 15 minutes later, I could feel myself starting to grow hard again. She must have felt it too as she began to rub me again, slowly, almost tentatively at first, then as I began to hump her hand, faster. I left my hand on top of hers this time and it was very erotic to occasionally feel myself between her fingers as we stroked. Her hand behind me began to move again and before I knew it we had repeated the experience, this time I was very aware of my dick jumping in her hand as I came, practice pumping, I guess. She must have felt it too, because she stopped immediately and just held her hand still, pressing my dick back against my groin. We repeated the experience three times total that night (not a record, one evening we started early and I came five times. She actually rubbed me raw, but that's a story for another time). After that first time, Bonnie became an expert at keeping me hard, teasing me to the edge, then moving her hand onto my chest or stomach to prolong the experience while I cooled off, finally stroking me to an orgasm before sending me to bed. I'm not sure why, but it never occurred to either of us to use any kind of lubricant. I guess I was too young to know about such things and she was too inexperienced. She still rarely said anything while she ...
    was fondling me only occasionally asking if it felt good or telling me I did good when I came particularly hard. Once she whispered as I was humping into her hand, "Can you come for me?" Those words had an almost immediate effect and I did come for her. I'm not sure why she didn't do it again. The fondling just became our routine. We never talked about it before I came down from my bath to watch TV. So when she came over, each evening started like a normal babysitting assignment, sometimes we played board games, sometimes I had homework to do and she would help me. I guess we both just assumed that it would happen after my bath. Strangely, she never offered to bathe me, either. Things changed again a few months later. One evening shortly after my folks left there was a knock at the door. When I opened the door this dark haired, tan skinned teenager breezed past me and asked where Bonnie was. I closed the door and lead her to the living room where Bonnie was sitting doing her homework. It turns out that Tricia was Bonnie's best friend. Bonnie and Tricia told me they needed to work on homework together and swore me to secrecy as I knew my folks had a hard and fast rule that Bonnie was not to have friends over while she was babysitting. Who was I to argue? While I hadn't originally noticed if Bonnie had breasts (actually she did, small "perky" ones) I immediately noticed Tricia's. She had what I would guess were large B or small C cup, pear shaped above a flat stomach that lead to ...
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