Everybody has a first time. Well, perhaps not everybody, but a lot of people have a first time. I’ve watched enough TV shows on CW starring unreasonably attractive teenagers to know that the first time is supposed to be special. It’s supposed to be with someone you love in a romantic setting. Ideally it will follow some big occasion, such as prom, graduation, a birthday, or a wedding if you’re extra weird. Everything will go smoothly and usually a soft melody will be playing in the background.
My experience was obviously nothing like this.
You see, I wasn’t always great at handling women. Truth be told, I’m still not that great. But at least now I’m tall, gorgeous, have amazing hair and binge drink. I didn’t have those things going for me until I was about 23 or so. Until then I was forced to rely on my personality. Don’t misunderstand, there is nothing really wrong with my personality. Well, there was nothing wrong back then; now I’m just a disaster. But back then I was sweet, thoughtful, nice, reserved, and sensitive. Everything women look for in a good friend, not someone to share a sweaty night (or 12 minutes) with.
Throughout high school I had plenty of crushes but few panned out. It was probably my fault for always having crushes on girls out of my league, but you have to go for the gold in life until you’re old enough to drink so you can settle for the consolation prize. I think I might have had a few close calls but I was too naive or scared to make any moves. It had to be special, after all. I continued to be a virgin by circumstance until I got to the slayer of virgins: college.
The setup
I was taking one of those random English classes people take in undergrad. A few weeks in we were assigned a group project and the teacher split us into groups. In my group was a girl that would change my life– Nikki (I think that was her name).
Nikki was 22 years old and not super interesting. She was a little overweight and not really that pretty– not that I was a prize myself. I wasn’t really attracted to her in the least, but I didn’t know a whole lot of people at the time anyway and she took a liking to me. She had just gotten out of a long relationship with a shitty boyfriend, so my nice guy routine was a refreshing change of pace. My birthday is September 14th, and this all went down sometime in late October. I was the mythical barely legal 18 year old.
We spent time together on the project, and I’m not quite sure how but we later started spending time not in a studying fashion. At some point she visited my dorm room and my roommate confirmed what I already knew; she was gross. The project wrapped up but we kept hanging out. It was roughly a week before Halloween and I ended up spending the night at her place. We made it all the way to hand stuff.
This went on for a couple days. We didn’t date or anything, I’d just come over and we’d make out then go to sleep. It was all very strange thinking back on it, and not something I would be into these days. But I guess that’s what you do when you’re 18 (and she’s 22?). She continually insisted that she didn’t want to corrupt me; I continually insisted that I was okay with being corrupted.
The fateful night
Halloween crept up and I didn’t really have anything going on. The day prior she invited me over and said her dad had ordered a costume that he didn’t need and thought it might fit me. On a normal person it would have been a caveman outfit. On a 6’5″ person (I grew a smidge more later in life; I’m now 6’6″) it was a caveman cocktail dress. She liked it, and told me to come to her Halloween party the next night. I accepted. After all, they were going to have free booze there.
The night of the party arrived and I showed up completely sober as an unintentionally slutty caveman. I was feeling a little self conscious, but luckily everyone was just as ridiculous. I found Nikki and started drinking. I laugh now, because I wouldn’t dare show up to a party sober. But back then I was a lightweight (literally a lightweight, I was 80 pounds lighter), so there was no need to pregame. I don’t know exactly what I drank that night; I’m pretty sure it was vodka and tequila but I can’t be certain. All I know is since I was relatively new to drinking I went from zero to train wreck in no time. She was in some kind of cat costume. I’m sure the costume was supposed to be sexy but the only clear memories I have are that she had orange ears on and was overweight. As a result, over the years the image of her in my mind has solidified as this:
The night continued and Nikki was getting increasingly drunk and handsy while I was just holding on for the ride. She noticed the door to her room was ajar so she dragged me along to see what was up. We opened the door to find two people in her bed half naked preparing to make sweet Halloween love. Nikki started screaming at them as they scrambled around trying to get their clothes back on and get out of her room. She turned the lights on and looked over on the floor and noticed something quite unpleasant: a massive pile of vomit on the floor next to her bed. Since she was a drunk 22 year old white girl, the obvious solution was to sit on her bed and cry about it.
She was bawling on her bed and I didn’t really know how to deal with this. Now I know the obvious answer is to just sprint out the door and never talk to her again. Let someone else deal with that. But back then I was nice to people, so I sat next to her, patted her on the back, and assured her everything would be alright. Her response to this? She turned to me with an unappealing mixture of tears and makeup running down her face and said… “lock the door.”
The first time
That’s right my friends. I’m not really sure how her mind jumped from “look at this puke on my carpet” to “I’m gonna bang this dude,” but I was now boarding the Pound Town Express and she was the conductor. I got up and locked the door (or so I thought) then went back to the bed. The party was still in full swing in the apartment, but we were now in our own world. I started to fumble around with various aspects of her costume, but nothing was working. I had never learned how to unhook a bra or how to smoothly remove various articles of clothing. To make matters worse I was impossibly drunk and nervous about what was in store for me. The furthest I had ever gotten was grazing a boob over a shirt, and that was with her two nights prior. I had no idea what I was doing.
How was I going to manage this situation? As it turned out, there was no need to worry; she had it covered. I felt like a dumb child while Nikki guided me through the next 10-15 minutes like a friend’s dad leading me around the bases in a tee-ball game (after I wrote this I realized how creepy the analogy is; I left it anyway). She had me taking off bras and pulling off clothes and poking and rubbing and slapping and stroking and really any other verb you can think of that would apply in this situation. It’s like she had read “How to Break in a Virgin for Dummies.”
Things hit an awkward peak when she was guiding me through a particularly advanced base. She pulled up me to kiss me then smiled and told me “you taste just like me.” I was puzzled by this, but explained that since we had been drinking the same drinks all night it made sense. She paused and said it again, with emphasis. ”No. You taste like… me.” A very embarrassing mixup. Sorry if that was more than you wanted to know. My young mind was not quite ready to process that, and it took me a minute to rebound.
Things were going about as smoothly as one could expect for a first time. I was drunkenly fumbling with parts I didn’t understand but still managing to get by. All of a sudden the door I thought I had locked burst open and some guy came in yelling about his jacket. Upon seeing us naked, he didn’t leave and instead started calling for more people to come into the room. Without hesitation Nikki jumped up completely naked and started screaming at him about not busting through closed doors. I felt like that wasn’t the first time she had been walked in on. Or even the fifth time.
After a short argument she chased him out then returned to the bed. She sat down next to me and for the first time I noticed how thoroughly unimpressive her body was. She leaned over and opened her drawer to reveal a plethora of different condoms and she started asking me about my size. How was I supposed to know? I’ll take the magnums please.
It was at that point I discovered just exactly how difficult condoms can be to work when you’re a nervous, incredibly drunk newbie. Thank goodness she had so many to spare because I went through quite a few before I got the trick. I watched The 40 Year Old Virgin a few years later and truly identified with his condom struggles.
The aftermath
After all that buildup, the sex was absolutely a letdown. It could be described with a variety of adjectives: underwhelming, awkward, lumpy, uncomfortable, squishy. Clearly none of these are good. I know I didn’t do a very good job, but for all her supposed experience I felt she really left a lot on the table. I guess there wasn’t really a chance for it to live up to expectations after 18 years of hype.
Afterward we cuddled quietly until we fell asleep (this was before I knew the tricks of escaping). The next morning wasn’t very fun either. I had the most miserable hangover of my life to that point (probably all the vodka and tequila… and the boning). With sex no longer on my mind it became alarmingly clear that I wanted nothing to do with this girl and just wanted to get out. Luckily Nikki had a test and I didn’t have to hang around and discuss it all. I dropped her off at school and promised we would talk later. In classic Lobrano style, we never spoke again. I had planned on dropping that class anyway, so I never went back. Problem solved.
Hooking up with Garfield might not have been pretty, but it was absolutely necessary. Besides, everyone knows the first time is a freebie. You can’t win them all until you win the first.
