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Everyone I've Ever Had Sex With: Male, 23, Austin
"I'm lucky she had a sense of humor, because looking back, that could have ended badly."
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The first girl I ever slept with, and my last relationship of any real substance. We were "in love" as only a high school couple can be, and she was a virgin too, which was a relief to me. Nine months after we started dating, we Did It. After I graduated, I moved in with her. Living together was surreal, and more than a little stressful. The sex was awkward, infrequent, and boring. We ended up making it to a year and a half before I broke it off. It was a clean break, and I'm happy to say we're still friends.
Sarah could have been my first, and every time I realize that, I nearly weep with joy she wasn't. She was an emotionally damaged, manipulative, drug-addled hot mess I had been friends with for years. There are not many girls I would "take back" if I could, but Sarah is on the very top of that list.
Vanessa was my first time having good sex, and mind-blowing, eyes-roll-back-good blowjobs. She was orally fixated, and she always swallowed. The one time we didn't use a condom, she hopped off my dick to swallow my load when I told her I was going to blow. So far, that's the only time that's ever happened. We tried dating after we had been hooking up for awhile, but it didn't work. I liked big words and she didn't.
Sally was my next girlfriend, who I dated for maybe six months. She was Pentecostal, drug-free, and a little crazy. I met her while picking up a buddy from work. She later went through the employee phone list for my buddy's number to bug him for my information. She was the first girl to cook me breakfast in the morning.
My sister's longtime friend. We had known each other for a few years, and had taken Chemistry together in high school, where I flirted with her for a year. She was over at my place hanging out with my sister, and they had decided stay the night. I was courteous enough to let Molly sleep in my room, and it turns out we both had the same thing on our minds. It was explosive in the way that only sex backed by years of unspoken sexual tension can be.
I met Jenny at the student union. If I recall correctly, I saw her a few tables away and said, "Hey you, come over here so I can flirt with you a bit." Later, we both got incredibly drunk at a party, and proceeded to make out in front of (and on top of) everybody. Rather than doing her in the bathroom, I decided to drive home near-black-out drunk to fuck her in my apartment with a condom (like a responsible adult). En route, her mother called, and she was drunk enough to give her mom my address. Soon after we got home and got into it, her mother arrived. After a lot of angry words and her mother slapping me, naked, in my own bed, they were gone. Her mother called me the next day to invite me over for dinner. I declined.
Gabby was the first girl to masturbate while I was inside her (which, to be honest, threw me off my already-tenuous rhythm). We would later go to a rave on Halloween, snort Ecstasy, smoke a joint, listen to Death Cab, and rediscover ourselves. We ended up fizzling out, though. She was dating another guy at the time, who she later ended up marrying. I think she made a pretty smart decision.
My first experience with an older woman. Jessica was twenty-five, I was nineteen or twenty at the time. She was a Jehovah's Witness who thoroughly enjoyed strawberry daiquiris, stand-up comedy, and the word "thoroughly." After we had sex for the first time, Jessica told her group of friends that I had a dick that "looked like a redwood getting pulled by two smart cars."
Sadie was was a smoking-hot punk rock chick who was way cooler than I was. We went out for drinks a few times, and during our first night together, I got my first case of whiskey dick. I remember being embarrassed, and more than that, confused. She was ridiculously good-looking, she was sucking my dick like she owed me money, but nothing was happening. It made no sense. The next few days I went full creeper and sent her a relationship request on Facebook. I never heard back from her again, and I honestly cannot blame her in the least.
The lowest of my sexual lows. I was at a party when Nancy latched onto my side and just sort of hung out there for the rest of the night. I was drunker than I should have been, and when our friends jokingly shoved us inside the only bathroom in the apartment, I just sort of took that opportunity to see how far I could go. (All the way, as it turns out.) Nancy was the first girl I kept around just for sex, which made me feel like a bad person and even worse when I found out I was only her second. The only other girl on the "take back" list.
NEXT: "... I was a little surprised when I felt her boyfriend's hand grab my cock."