After Joanne and I broke up, I figured I'd be fucking some other girl before long...but it didn't work out that way. I wouldn't have sex again for over two years, and I wouldn't have another steady girlfriend until my sophomore year in college. Her name was Amy, and she was a slim 19-year-old with short blonde hair, blue eyes, small breasts, and a sexy, fit body. She was athletic — a runner, to be specific — and a bohemian/hippie-type who liked to write poetry. I wanted her as soon as I met her, and eventually we became close through mutual friends. She was the first girl I truly fell in love with.

Amy was a virgin when we started dating, and we had sex for the first time on New Year's Eve 1999/2000. Despite her inexperience, she was adventurous and up for anything. I couldn't believe my luck...I had found an actual virgin/whore! Even though this was like 15 years ago, I can remember more specific sexual encounters with Amy than I can with any other girl I've been with. Such as...

- The first time I came in her mouth, which happened in her bedroom. She didn't know if she should spit or swallow, so she kind of just let the cum drool out of her mouth afterwards. She felt embarrassed about it, and of course I told her not to worry about it. "You can swallow it next time," I said. And she did. Many times.

- We had sex on train tracks, high above the water on a covered bridge. I was nervous that a train would come around and squash us, but she assured me that if a train came along, we'd be able to see it a long way off and get off the tracks in time.

- I put a belt around her neck while fucking her from behind, several times. She was into it.

- I stuck my finger up her ass while she was on top of me, many times. She was into it.

- We fucked in a rainstorm, hanging halfway out the backseat of her car while Neil Young's "Cortez the Killer" played from her radio. Still love that song.

- She rode my cock outdoors in a nature preserve, late at night.

- She sucked me off while we were driving on I-94, and I had the most intense orgasm of my life.

- I fucked her in her parents' basement, on their pool table and on the floor. Her dog came around and tried to lick my ass while I was fucking her, and it freaked me out. I don't think Amy noticed.

- I fucked her in the ass once. Without lube. I didn't know what the hell I was doing. Yeah, that wasn't a personal highlight, but I'll never forget it.

- She asked me to hit her once, during sex in a cheap hotel room, and I slapped her across the face. I'm still not exactly sure if that's what she had in mind.

I could go on and on like this. Amy wanted new experiences and she was a little dangerous. I was just along for the ride, and I loved it.

Around that time, BlacksOnBlondes was gaining popularity, and the site introduced me to Anastasia Blue — a petite blonde who looked meek but was sexually fearless. She immediately reminded me of Amy, and I started fantasizing about Amy being gangbanged by Mr. Marcus, Lexington Steele, and Jake Steed. I thought about how I could pimp Amy's tight pussy out to nasty black men. I *still* think about that once in a while.

Amy and I broke up in late 2000, I think. Our lives were heading in different directions, in a literal sense. (She was a country mouse, I was a city mouse.) Like Neil sang, "Now she's pushin' two kids, loookin' for that magic kiss..." Anastasia Blue died in 2008. Much love to Amy and Anastasia, wherever you are.

XVideos links:

Jake Steed Lex Steele & Jack brutalize Anastasia

Still afraid of possible Consequences (Anastasia vs. Jack Napier)

Anastasia Blue - Cock Smokers 12

Anastasia POV sex