Though technically not my first time, this was definitely the first meaningful sexual encounter I had. I had been dating this girl for a few weeks. We both wanted to do it; she made it clear that after I met her parents she would “let me inside.” She was a virgin, so she was really looking forward to having sex, as was I. A few days after I went to her house to eat dinner, we found ourselves in my living room at 10 o’clock with my parents already in bed and sister distracted with other things. We had talked about doing it, and both expressed that we wanted to do it soon, but we hadn’t come up with any time or finalized anything. However, the time seemed right, so we snuck outside to my garage where there lay a mattress on the second floor. We made out for a bit, before she took off her clothes and I took off mine. It was time to begin.
I took my dick and slowly began to put it in her vagina. I was watching her face, looking at her expression, trying to make her as comfortable as possible. She opened her mouth, and said “ooh,” implying that it hurt. I took my fingers, first one, then two, then three, and began to open her up a bit enough so I could get it in without hurting her. Eventually, we got going. At one point, she asked me “How far in are you?” to which I replied, “About halfway…you?” Immediately realizing my unintentional idiocy, I laughed with her as she told me she was going to quote me on that. This didn’t interrupt the flow, however, as we kept going seamlessly.
However, we heard the door open downstairs. We both freaked out, scrambling to find our clothes, putting them on in a rush. I crept down the stairs to see what was going on. My dog was at the bottom of the stairs; apparently he had been too loud on the back porch, prompting my sister to put him out there. “Whew,” I said, locking the door (something I had forgotten to do, yet told her that I had.) “That was close.”
We undressed again, this time being careful to put our clothes together, and got going a second time. This time, she had no trouble with me slipping right in. Her boobs weren’t that big, but I could still feel them as I railed against her in missionary. She started pulling me against her as I kept going. I grabbed her ass, prompting her to grab mine. We fucked for a while, before I came in her, vocally expressing my climax. I asked her, “Could you tell (that I came)?” to which she replied laughing, “Well, it wasn’t like you were subtle.” We both laughed about it as we walked out of the garage, our mission having been completed.
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