My Favourite Life

August 23, 2006

My First Time

Filed under: breasts,Fellatio,Pussy,Sex — myfavouritelife @ 10:35 pm

I grew up in Boston, but we had a boat we kept in Rhode Island. During the summer between 9th and 10th grade, I met a girl, Donna. Donna was a Canuck living in Rhode Island, and her family stored their boat at the same marina as we did. We spent most of the summer together. She had a female friend that was often with her. At the end of the summer, I had my first sexual experience.

Her friend was not with her on that day. Let me provide some backstory. Donna had just graduated from high school, and she wasn’t planning to go to college. She wasn’t very ambitious—at least academically. During the summer we used to walk hand in hand, arm in arm, and caress each other Platonically. I remember many days sitting together and talking for hours in an old dry-docked boat. I would put my arm over her shoulder, and she would do the same. I remember being quite nervous, and I would play with the buttons within reach on her blouse. Occasionally, a button would come undone, and she would just rebutton it—until this time.

This time, she asked, “why are you always playing with my buttons?” Being even more nervous, I didn’t know who to answer. So—like out of Penthouse Letters or some such—, she positioned herself so as to guide her breast into my hand and wait for my reaction. Admittedly, I was in shock, so I froze like a deer in the headlights. She wasn’t put off, and she asked if I had ever been with a girl before. I answered no. To tell the truth, I hadn’t even thought about it much. Sexually precocious, I was not.

She asked me if I liked what I felt, so I told her I did. It was all very awkward. When I wasn’t making any real progress toward what I can only imagine was her goal, she asked if I wanted to see them. Even I said yes to that. She removed her bra. Wow! They were small—probably A or a small B cup from what I later learnt—, but I didn’t know any better and didn’t care anyway. I have never been a breast guy. Then she let me feel them. Nice!

She started feeling my chest and then pulled me to her and hugged and kissed me. I hadn’t even kissed her to this point. It was never my goal. I just went with the flow in a Zen sort of way.

It was autumn, so she had started with a blouse and jeans. I had on jeans and a t-shirt. Her top was off, and she unbuttoned her pants suggestively. It was really a whirlwind blur from that point on—and not that it hadn’t been before that point. I guess you had to have been there. As she was unbuttoning her jeans, she asked me to do the same. I was clueless, but I went along. Soon we were both in our underwear.

She asked me to take of her panties, so I did. I have never seen a pussy before, not even in magazines by that time, I don’t think. She rubbed pussy with a full bush and asked me to feel for myself. She must have been wet, but I don’t actually remember, but I do remember sliding my finger into her after a few moments, and she reached down my pants and felt my cock, which was not very impressive, I have to admit. Like I said, I was in shock.

She removed my underwear, and there we were—both naked. While she might have had some experience—I never did find out, though she was no virgin—, it was not obvious. She fondled me to an erection with her hand as she lay down on the couch spreading her legs for me and guiding my cock into her pussy. It must have felt good. Why wouldn’t it? But I don’t really remember. I remember her guiding my hips until I came.

That was it. After I came, she asked how it felt, and I told her it was nice. I didn’t know that she was supposed to have an orgasm, too. Who knew? She never asked. I didn’t know any better. Later in life, I would learn to eat pussy to please a woman. I do love to eat pussy, just not then. Later in life, I would learn about blowjobs and anal sex, but not then. I had no idea. I had been innocent. But I hadn’t lost my innocence. It was not until a few years later until I would have sex again. And I never saw her again.

I was so innocent, that I didn’t even know how to masturbate.We learnt about it in school, and people talked about it. I even had a friend call me a liar when I denied the act. I was still innocent. I had had sex, and I had even had some wet dreams, but I didn’t masturbate until Yuka did it for me when I was 18 (more on her later).

So this was my otherwise uneventful first time. Would I change anything? Probably not, but it would have helped, I think, if I had had more information going into it.

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