Kari was my best friend from 10th-12th grade. She conveniently also lived behind my parent’s house. Our friendship epitomized the idea of proximity fueling affection.
One weekend, Kari and I decided to go through our parents’ jewelry boxes and pawn some of their old precious metals so we could go on a little shopping spree before school started again. Yeah, we were scumbags.
Kari and I actually stole a lot, but that’s probably a story for another time.
Anyways, we loaded up on old rings, necklaces and gaudy brooches we had never seen our mothers wear and drove three towns over, to this shit hole white trash town where the most exciting thing to do was visit a strip club in the morning and wait on some good crack cocaine to be offered up for sale.
Once in the shitty town, we went to a pawn shop and that’s where I met Greg. Greg looked like Daniel Radcliffe in his Harry Potter days plus about five years of hardcore heroin use. He had sunken in eyes and the bone structure of a sickly pre-pubescent boy.
He was working the counter with this other guy, Kyle, who took one look at Kari’s half missing acrylic manicure and busted out laughing, calling her nails “busted”.
Kari wanted to leave instantly, before even showing them our looted bag of jewelry, but I insisted on staying. We sat at the counter for about 45 minutes as they scraped, weighed, and tested the jewelry that we had brought in.
Somewhere between Kari signing the forms saying the jewelry wasn’t stolen and handing us the $400, Greg got Kari’s phone number.
It’s important to note that I did not have my own cell phone at this time (thanks Mom and Dad) despite being 17 and I frequently used Kari’s cell phone to make plans with my friends.
A few nights later and Greg and I had been texting up a storm. He wanted to hang out. I was stoked but super nervous because, well all the reasons.
So I arranged a double date with Kari and the douchebag Kyle, and Greg and I. We all agreed to go to the movies and see the Harry Potter movie. Kari was not stoked about the planned events at all and made it quite clear that I’d be indebted to her.
I thanked her profusely and we got cute together and headed off to the movie theatre.
Because we had met the guys a few towns over, we met at one in between ours. I don;’t remember much of the movie but I do remember groping his penis through his pants and his mouth hot on my neck. Oh, and Kari’s eye rolls from three rows behind us.
After the movie we went our seperate ways and Kari and I gossiped about Greg the whole way home. She did not enjoy her evening but she was a good friend.
The next week, and I had convinced Kari into doing me another favor and she was driving me to Greg’s parents house for dinner.
Not because he wanted me to meet his parents but because he lived with his parents.
I remember what I was wearing (this little school girl skirt and a red shirt) because as soon as I stepped out of Kari’s car and hugged Greg, he told me that I should have worn something else.
“My mom just hates skirts. She thinks they’re slutty.”
I instantly started freaking out, much to Greg’s amusement as he was fucking trolling me.
We walked up to his super fancy house and walked inside. There was a game room to my immediate right as I walked in and I saw a massive pool table centered in it. It looked as if it rarely saw use.
Greg’s mom met us as we made our way towards the kitchen. Upon seeing her, I wondered if Greg had had multiple motives with trying to lighten the mood. Greg’s mom had no legs beneath her knees and was seated in a wheel chair, the kind that was electric and requried no upper body work at all.
She was morbidly obese. I guessed diabetes but didn’t have the balls to ask Greg later when we were alone.
Greg and I made the usual small talk with his mom and she asked pretty much only the questions that I didn’t want her to. You see, Greg was 6 years older than me and when his mom found out that I was still in high school…well it didn’t take even a middle school education to know what she was thinking.
Greg and I excused ourselves to go into his room. We started making out instantly. I don’t think he and I ever actually talked about anything. He started getting super handsy with lingering touches up under my skirt and pushing the bubble of anxiety in my stomach down firmly, I pulled back, looked down at my lap and told him that I wanted to wait.
I told him I had had sex before and I wanted to (lie lie lie) but that I hadn’t really had the best first time and was still figuring out some stuff. I then told him I was down to do whatever else.
I gave him props when ten seconds later, despite the complete killing of the mood, he suggested that we go swimming in the pool.
I was down,and had brought a bathing suit in the event of this happening. I changed and we went in.
The water was fucking freezing and I hated jumping into it but I wanted to look cool. So head under and all, I plunged under.
Greg and I immediately picked up where we had left off in his bedroom. My legs were wrapped around his waist in the 4.5 foot section and his mouth was attached to mine.
He moved it everywhere, up and down my neck and I remember being surprised by how sensitive his mouth could still feel, despite competing with the cold pool water for my skin’s attention.
He plunged me underwater, not breaking his mouth away from mine and together, we realized that Hollywood seriously dramatizes those romantic underwater kisses in cutesy moves that make me want to masturbate.
We came back up and I was spinning. We frolicked about a bit more in the water until his mother rolled outside and told us dinner was ready.
At the dinner table, I met the rest of the family. Greg’s older brother looked like a slightly less lean version of Greg. Still impressively thin but neither of the spawn looked remotely like their parents. Both Greg’s mother and father were obese.
We ate steak. I don’t really like steak that much and my hatred for it only grew when Greg and his entire family snickered when I asked them to pass the Al Sauce.
I didn’t know it was pronounced A1. Whatever.
After dinner I offered, and was luckily refused, my assistance with cleaning up.
Greg and I went back to his room.
we messed around a bit and he got my pants off.
I didn’t think to remind him again that zero part of me wanted to have sex because the first time had been so awful.
His fingers clumsily poked at me and I tried so hard to make myself enjoy it.
I found it much easier to contemplate what exactly constituted “sexy thoughts” than I did actually thinking sexy things.
Greg ended up putting his penis in me. I didn’t even realize he had taken his penis out and it was inside of me. I pulled away instantly, feeling annoyed and slightly sickened.
He told me we should go watch TV and I texted Kari to come sooner than originally planned to retrieve me.
On the car drive home, I told Kari about how awkward the whole thing had been.
When I made a comment about not seeing him again she made a joke about it being good that I hadn’t slept with him.
I laughed dryly and she didn’t notice the difference.