Boo was a young and very curious girl when we first met.
Like many of my adventures, this one takes place a few years ago. Boo was a neighborhood kid, 13 when we first met. She was pretty, very pretty. Her family was, in my opinion, pretty screwed up. They were into some weird fundamentalist religion, were extremely strict with her, taught her from an early age that sex was dirty. It got worse as she got older.
They put her in a really strict fundamentalist religious school that, among other things, believed that sex ed was the work of the devil. Her parents felt the same way and, as I was to learn, Boo was given absolutely NO sex ed at all, not even the basics of where babies come from. Needless to say, when she got older, she was absolutely not allowed to date or even go to the malls or movies with her friends. About the only thing she was allowed to do away from home, besides go to school and to church several times a week, was to visit with the family who lived right next door to me and, for some reason, her parents didn't seem to object to her coming over to talk with me every once in awhile when I was out on the deck.
(I was single at the time, lived alone and not involved in a relationship, although I did have a couple of "friends with benefits").
Now I wasn't about to get involved with Boo or her family in any way. First, at least at the beginning, she was definitely underage (the age of consent was 16), and I certainly wasn't going to take advantage of her, nor did I have any desire to put myself in legal jeopardy. We did become friends, though, and over the years she would confide in me. As hard as her parents tried to isolate her from the real world, she still managed to have some girlfriends who knew more than she did about the realities of life. However, most of them didn't know all that much and some of the things they thought they knew were just plain wrong (for example, they thought that there was no way a girl could get pregnant the first time she had sex, a girl could get pregnant by letting a guy "shoot his seed" into her mouth and swallowing it and many other similarly erroneous things).
Like any girl, Boo was curious about sex and, as she and I talked, she became more and more open about asking me about guys, dating, pregnancy, STDs and similar subjects. I always told her the truth and felt that somebody had to keep this kid from getting herself totally fucked up, not to mention let her know that sex was healthy, normal and pleasurable. Our conversations, while candid, were at first essentially "clinical," limited to what I'll term "sexual mechanics."
One afternoon it started to rain when we were sitting on the deck and we went into the house and were sitting in the living room talking and the subject turned to sex. Boo was much more talkative than she had been before and was asking me a lot of questions. We discussed everything from orgasms to oral sex and she seemed to be quite fascinated. She had heard about these things, of course, from her friends and was asking more for confirmation than anything else. This conversation was to be the first of many and we became what you might call "co-conspirators" in her sexual education.
This entire situation or relationship evolved over a period of about 3 or more years...I'm compressing the time and events to the most "interesting" of our visits and sex talks.
Over time, our conversations became more candid. One afternoon that I remember, we talked about masturbation and she told me a few days later that she had "tried it and it was really awesome." I felt as if I had been responsible, in some small way, for her first orgasm. She became increasingly curious about my sex life and I answered her questions candidly, although I was careful not to reveal the identity of my girlfriends. She was also very curious about masturbation, wanting to know how often I did it, was it normal to "do it every night and sometimes more than that?" She wanted to know how often I did it, if I ever let a girl watch me, did my "seed" come out - essentially, every detail.
Several weeks after her first masturbatory orgasm we were having another of our "sex talks," as we had come to call them, and she asked me if it was really true that a guy's dick was so big when it got hard that it really, really hurt when a girl had sex the first time. I assured her that this was not necessarily true, that guys were of different sizes, as were girls, and that it all depended on how big the guy really was, how tight the girl was, if the guy knew what he was doing, how lubricated the girl was, etc. Boo then asked me, almost out of the blue, "How big is yours?" I hesitated for a moment, knowing that we were close to some imaginary boundary. But I knew that if I avoided the question, it wouldn't be consistent with the openness and honesty we had developed between us. So I told her. She was silent for a long time and then she asked, as I thought she might, "Can I see it?" (I should interject here that over time Boo had developed into a bit of a tease and a flirt and I was quite sure that had I said or done anything to initiate sexual contact between us, she would have responded eagerly.
However, with her asking to see my cock, we were definitely at a boundary and a crossroads. I must admit that I was feeling just a little bit aroused but simply couldn't cross that line. I was happy to educate Boo verbally, but this was just a line too far, no matter how much I was tempted.
I think about Boo a lot and hope she was able to develop a sexually normal life.
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