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Unsent Letters to a Crush

Three letters written months apart during freshman year of college to the only high-school crush I thought I might honestly have a chance with (and then only after high school when became close through letters); none of these were ever sent -- I think I would have written something that didn't jump right into sex if I had actually resolved to send something, perhaps a slightly edited version of the first one. But I never sent them, and the next year I was involved with Fred and so not much in need of boyfriend or sex partner for a while.)

9-6-91

Dear Rob,
Are you in a comfortable reading position, without anyone reading over your shoulder? This is a private subject I'm about to discuss, and I (and hopefully you when you've read it) don't want the entire world knowing about it. Stupid shyness.

I read your description of people you like. It sounded quite nice theoretically, but it doesn't seem to relate to reality except for you, who understand what you mean. I can't read your words and think, "OK, he'd like her1 but not her2," you know? And of greatest concern to me is "Am I someone you like?" Because I like you. As a friend, which should be obvious from all these letters. And as a guy. I wouldn't say "romantically" because I've told you my opinions of "romance" as usually thought of, but I think you're very good-looking. And I've been fantasizing about you since 9th grade. (There, I've actually written it. Now I just have to build up enough courage to send this letter, which is why I dated it, so if I ever send it, you can see how long it probably will have taken me!) But I've been shy, and you're not (well, nobody is) easily approachable on this subject. I couldn't just walk up to you after Latin or math or physics and say, "I've been sitting here imagining what you look like naked," even the many times it was true (or more; my imagination is not easily stopped when my hormones are at the controls).

So now I've become courageous/longing enough to write this letter, although it's pretty useless to be so since we're a county or three apart (my lack of knowledge of geography except for the immediate Bay area) even if you were interested, which has not yet been ascertained. If you happen to have read this without feeling totally disgusted with me for not being a simple friend, please tell me and maybe some suitable course of action can be collectively worked out.

Yours truly,
Josie

Dear Rob,
I've been fantasizing about you since I've know you, starting in Mr. Brown's class. I've wanted to take your clothes off, and do just about everything we could possibly do. I've even got stories, written-down fantasies about you and me.

I want to undress you and run my hands all over your naked body, and especially your cock. Then I'll take off all my clothes and sit down next to you and you'll kiss me, deeply, and caress my tits, and I'll spread my legs so you can see my cunt, and put a hand there to feel how wet the sight of you is making me.

I'll reach down and run my fingers over your now-hard cock, and then get down between your legs for a closer look and even a tentative kiss on the head, but then I'll rise back up again and recline on the couch so you can lean in for a close look. Then you position yourself between my spread legs and push your cock inside me, slowly at first, then more confidently and faster while I start to push upwards in time to your rhythm.

This goes one as long as we both can keep doing it, and then you moan that you're going to come and you do, and your orgasm sets mine off, and it's wonderful and then there's this satiated heap of us.

I wish this could happen.

Love,
Josie

Dear Rob,
This is going to sound weird, but I mean it quite seriously. I trust you. I consider you one of my best friends and I also find you quite attractive. So you seem like a logical choice for my first fuck. (Nothing like bluntness, is there?)

I forget who said "curiosity has broken more young maidenheads than love" but it's true, and I've been damn curious for eight years, about you for four of them. About time I satisfied my curiosity; why I waited this long I'll never understand. [Shyness and lack of opportunity, mostly.]

So are you interested in helping me out? If you happen not to be, I won't take it amiss. (Never could figure out how well I fit that list of what you like in other people.) Next time we're both home on vacation (is your spring break the same as ours?) when my mother isn't home (which is most of the time) or maybe even some weekend would probably be a good time, if you agree. Awaiting your answer,
Josie

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