tagFirst TimeBlack Book Diary Entry: Aileen

Black Book Diary Entry: Aileen

byPositiveThinker©

I had a lot of first with Aileen. Aileen was my first real love and my first imagined girlfriend. She was the first woman I had ever kissed, French kissed. She gave me my first blowjob.

I met her so long ago that you'd think I'd forget her, but I never have. I sometimes wonder where she is now and how different my life would have been with her in it. She could be dead for all I know, but that doesn't stop me from still thinking about her.

We were both 18-years-old and she was very pretty. The main thing that attracted me to her, of course, was the way she looked. She was taller than the average woman at 5'7", when most women were only 5'4". As Irish as she was beautiful, she had long, straight, blonde hair, a round face with smallish features, and hazel eyes.

She was the first skinny, flat-chested, blonde that I was ever attracted to. Before her, I was always attracted to short, brunettes with big tits. It's funny that I didn't married a short, brunette with big tits. I married a tall blonde with big tits. Perhaps, I guess, I took what I liked from one, tits, and looked for a woman who had the other, blonde hair.

There were always other people around us, whenever we were together. I could never get her alone long enough to tell her how I felt about her. In hindsight, a good thing because I never would have married the gem of a woman that I married, instead of Aileen. I married Aileen's best friend, Arlene.

Shy and lacking confidence, back then, I was afraid she'd reject me. Yet, in a way, I rejected her by not even trying to win her. I always wished I had thought of that back then, as a confidence booster to push me to ask her out, but now, I'm happy that I didn't.

We never dated, we were just friends. We hung out together. The only time I really spent any time with her was when we went to a party but with all the people milling around and loud music, I still couldn't get her alone long enough to have a real conversation with her. Back then, there was always a party somewhere.

I realized later that it turned out that she was a bit odd, cold even. She was the shy, quite, and reserved type. Everyone liked what she looked like from the outside, but no one really knew her for who she was. Except for Arlene, she didn't have any close friends. Arlene was always making excuses for her and dragging her out of places before she got into real trouble. Remembering the way she was, now that I think about her, she didn't have much of a personality. She was a bit moody.

Perhaps, I was attracted to her moodiness then, but I certainly don't like moody women, now. Perhaps, I saw her moodiness as mysteriousness. What did I know? I was so young and so very inexperienced. All I knew was she reminded me of Allison McKenzie, the role that Mia Farrow played from the television series, Peyton Place, and that was enough for me. My testosterone blinded my judgment.

Aileen enjoyed doing drugs, for one reason or another, probably because they were mind altering, pot, hash, pills, and cocaine, which would explain her moodiness. I never did drugs. I only drank. I knew enough about drugs to know that I really didn't know anything about drugs. After seeing how fucked up some of my friends were on drugs, I feared them.

Because she was into drugs, she started running with a different crowd and it wasn't very long before everyone had a turn with her. It was so sad, really. It was the sexual revolution and a time of free love, after all. It was a time where Woodstock created a better memory than a reality and everyone said they were there, even those who didn't even know where Woodstock was on the map. Only, Aileen wasn't part of the sexual revolution, she was parcel to it, a product and a fatality of it, doomed to repeat her mistakes of promiscuity over and again with, yet, with another emptied bodied, drug dazed partner.

I learned later that Aileen would do pretty much anything with anyone to get high. I guess I never considered her addicted to drugs or a druggie, but she was. I just considered her as Aileen, my beautiful friend, who I lusted over. Blinded by love, I couldn't go there with my thoughts in thinking any less of her. Only, she thought less of herself and used the drugs to disappear.

She was the first woman I kissed and the first time I kissed her was when I rescued her from the clutches of my friend, Mike. She was drunk and stoned out of her mind and he had been hitting on her, before making out with her at a party. Mike was a player and bedded women in the way that I changed my socks. I was angry that she was with him, instead of with me. It's amazing the things that go through your mind when you're so young, so dumb, and so full of cum. I was so naive. I was in love.

I pulled her away from him and took her out in the hall to get some air. Mike was too drunk and too high to know we had even left. When I was standing so close to her that I could smell her perfume and feel her soft blonde hair against my cheek, I remember imagining that she could love me as much as I loved her, once I kissed her. I looked into her glazed and glassy eyes and kissed her.

My first kiss was with the woman I loved. It was a soft kiss, a kiss that I had dreamt about doing for months and I swooned with the touch of her soft, full lips. Only, as soon as I inserted my tongue in her mouth, she pulled away, turned her head, and puked. How's that for a memory of our first kiss?

Then, I don't know if she was too drunk or too high to realize who I was but, out of practiced habit no doubt, she fell to her knees, unzipped me, and pulled out my cock. Before I could stop her, she had my cock in her mouth. I didn't think of her like that. She was my first love, but I didn't have the control to stop her from blowing me. She gave me my first blowjob. How could I stop my first blowjob? Maybe she thought I had drugs or had given her drugs, I don't know.

It didn't take me long to cum in her pretty little mouth. Only, instead of being excited about the experience, I was sad. Yeah, she gave me my first blowjob, but I wanted more. I wanted her to love me, as much as I loved her. Only, it would never happen.

There I was willing to ruin my friendship with Mike to protect her from him. Actually, I was more hoping to save her for me. Truly, I wasn't as much of a big protector, as I wanted her for myself. I didn't know my friend had already banged her at another party. I didn't know she already had multiple lovers. I still thought of her as a sweet, shy, pretty girl, a virgin. Had I known she had been with so many others, would it have made a difference about how I felt about her? Probably not. I was in love with her.

I couldn't help but feel a little bit like Nick Carraway in the Great Gatsby, in the way he lusted over Daisy Buchanan and in the way that I lusted over Aileen. Much like Aileen and I, Nick and Daisy were friends, who'd never be lovers because Daisy loved someone else, Jay Gatsby, just as Aileen loved whoever could get her high and take her where she needed and wanted to go to escape the sad reality of her life.

I never knew that about her, that she had a troubled childhood, a victim or verbal and sexual abuse. I just saw that she was beautiful and I was in love with her. To me, she was perfect. In essence, she was broken, too broken to ever be fixed and I was better off without her. Only, it took me a decade to realize that.

Merry Christmas Aileen, wherever you are.

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