I was 19, fresh out of my first year of college, armed and ready for the summer with my flawless fake ID. It was a full four months of bars, booze and flirting shamelessly with older guys. The only thing holding me back was the frustrating burden of my virginity.
However, a few minutes after entering my favorite bar one Friday night, I was approached by one of my guy friend’s older brother. He bought me a drink, and we talked. He was 29, attractive, entertaining and laidback.
After a few weekends of simply talking to him at the bars, he leaned down and whispered into my ear, “I would really love it if you came home with me.”
If I had been sober, I would have been too nervous and would have found some excuse to say no. But thanks to my alcohol-induced courage, I calmly agreed to his proposition. I’m not sure how many people have been in my position (about to have sex for the first time ever with a guy that you’ve talked to probably a total of 5 times), but I felt obligated to tell him that I was a virgin.
Easier said than done, as I figured out. Or, rather, easier thought than said. In what I still think has been my most uncomfortable conversation to date, I finally managed to spit it out. Not only did he already know, but he thought it was fantastic. This took a ridiculous amount of stress off of me that I didn’t even realize I had. As long as he knew what to expect, I was no longer worried. This situation was getting more perfect the more I thought about it.
After drinking wine and talking for about an hour or two, we finally went up to his room where I immediately collapsed onto his bed. It was about 5 a.m. at this point; I had a great buzz; I was lying on the bed of an exceptionally good-looking guy and he was into me. I didn’t even care what happened at this point, I could still brag about simply being in his room. He might have said a few things to me — I don’t remember — but what I do know was that he was finally on top of me with his tongue in my mouth. Suddenly, I was too drunk to even enjoy this amazing victory, I was only focused on getting more, which I got — quickly.
I immediately realized that this was nothing like the college guys that I’d hooked up with before; he was just so much older, way more experienced and so skilled. If I didn’t fuck him, I would never forgive myself. Somehow, all of our clothes found their way to the floor, and his tongue found its way down there. He went to town and acted like he could be down there all day, which made me feel absolutely amazing about myself.
Then, we were finally doing it.
Well, first he’d stopped me a few times to ask if I was sure, and to tell me that we didn’t have to and that “I really don’t want you to wake up in the morning and hate me.”
God, I’d never been so sure of anything in my life. I think I told him to shut up and get a condom, although I might have been more polite. I just needed him to stop being so nice about it and just fuck me, for god’s sake.
After initial and inevitable discomfort, things started getting really good, really fast.
He didn’t ask me if he could do something, he told me what he wanted me to do. Flip over, stand up, touch this, do that. This was not only helpful, but also extremely sexy. Every dirty thing he said to me was seriously intoxicating, and I was practically getting off on his words alone.
After a very long night of sex with a guy who did everything as close to perfect as I could imagine, I had one concern: I liked it way too much. He had made my first experience so enjoyable that I was scared I would drop any morals I had left to become more promiscious.
I spent every weekend night for the rest of the summer in his bed, and the more comfortable I got with trying new things, the more I worried about my future integrity. It’s not like I was in love with this guy—I was just in love with the sex.
If I have any good advice to offer, it’s this: Sleep with someone who’s at least 6 or 7 years older than you in the next few years. It feels nice to leave the world of college hook ups for a few nights. Clean and expensive sheets, no roommates, a kitchen full of actual food—not just frozen pizza and about 10 years more experience than you in bed.
We still hook up when I’m home, and to this day, I’ve still never had better sex than I do with him. And, out of all the stories I’ve heard from friends about losing their virginity, mine is hands down the best. Not that it is a competition. Wait, yes. Yes it is.