I was a late bloomer, and not feeling too good about myself9, since I was still a virgin. I didn’t even really have my first real kiss until 18, so my sexual self-esteem really couldn’t have been much lower.
Predictably my self-loathing brought me to internet chat rooms. I think it was on Excite chat when I happened to talk to a young lady who happened to live or 15 minutes away. Well, after an hour or so of chatting she asked if she could call me on the phone, I said fine. This continued for a few days, maybe a week or two at most, where she would call me pretty much every night. Of course, I was curious as to what she looked like. She had described herself as attractive, I think, so I was optimistic.
Well, she finally sent me a picture after some technical problems. She was not attractive, and her personal descriptions were inaccurate to say the least. Overweight, nay, fat.
But as I said before, I was a sad and desperate young man. I was also a doormat, unable to say no. So she became more and more forward and explicit in her phone conversations, finally saying that she wanted to give me a blowjob, to “loosen me up,” or something. So I guess that removed any remaining ambiguities in the situation.
A few days later she came over for a “date” or something, I don’t recall what the pretense was. Needless to say we never left my apartment.
She said she wanted to see the view from my balcony, and once we were out there she put her arms around my waist, and basically got in my face. (You know what I mean, it’s what women do when they don’t actually want to initiate a kiss, but are getting so close to your face that really you don’t have any choice but to kiss them. They are making their intentions and desire totally clear while still giving themselves plausible deniability. “But you kissed me!” You know what I’m talking about. But anyway)
So after kissing for a while, she brought me inside and pulled my pants off and started to try to give me a blowjob. To add another sordid dimension to the story, I was on Prozac at the time for my crushing depression so I couldn’t get it up. I guess I enjoyed it, and it was my first blowjob, but without an erection some of the fullness of the experience is lost. But we pressed on. She asked me if I wanted to go down on her (she was being understanding, knowing that I was almost totally inexperienced). I did, and was rather repulsed by the smell and taste, but it was pretty fun. She did orgasm, or so I assume from the very noticeable muscle contractions.
But sex was on the menu, or at least a pitiful attempt at it. It’s tough, stuffing a limp dick into a vagina. I did my best, as did she. Does this even count as sex? If it doesn’t, I didn’t lose my virginity until a few months later. That story is even more disgusting and sad than this one.
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Paulie
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