Up until high school, I had never had a real boyfriend. It wasn’t that I was ugly, or that I wasn’t capable, it was more so that I had way too high of expectations. I watched one too many Hallmark movies around Valentine’s Day and read one too many “Y/N” stories on Wattpad. Therefore, it was just me and my right-hand index finger.
Though I was without a man, I was familiar with the idea of masturbating—and felt no shame in doing so. I would moan a cute senior’s name as I reached climax, imagining them and me, though I wouldn't have the balls to approach them in real life.
I remember my pre-boyfriend, sixteen-year-old days: masturbating in the shower using the shower head, after school, at two in the morning when I should’ve been sleeping so that I’d be up for school four hours later. I was content and therefore never really dwelled too much on the idea of being single. It wasn’t until my friends were all losing their virginities and creating memories that my fingers couldn’t amount to, that I realized I had desperately wanted a boyfriend.
It was now the end of sophomore year, and I was single and desperate. I had options, but I was picky…thanks to Hallmark and Wattpad. My ideal boyfriend had to be tall, taller than me by a decent amount. He had to be fit, like rock hard abs fit, and had to have curly hair. Oh! And he needed to be tan of some sort especially. I loved seeing naturally tan guys.
As I took in my options, looking through my messages on Instagram and seeing what male schoolmates may have been in my DMs, I noticed a boy, named Ben, who was known as “crazy” to many at school but fit my ideal profile. “Hi,” I texted Ben back, not caring about what others said about him. I mean, what does “crazy” mean anyways?
Ben and I began talking and we didn’t hesitate to make it known in school that we were talking either. He would come up to me and hug me, walk me to class, and sit with my friends and me at the lunches we shared with one another. I was known as a relatively quiet girl, so I was surprised at myself, seeing that I didn’t freak out and act super awkward when he came around.
Ben was the start point guard on the basketball team. He wasn’t disliked, for the most part, but as I’d said, many called him “crazy,” especially girls. One day after Ben dropped me off the class, a girl moved her seat and sat with me during the “free time” we’d been given after having completed an assessment. “Hi, are you the girl talking to Ben?” the random girl greeted me.
I nodded, “yeah!” I said with excitement. Being noticed in this way felt so cool. I wasn’t a loser or anything, but people outside of my friend group didn’t pay much attention to me beforehand. However the girl’s face changed upon hearing that, “you’re a virgin, aren’t you?” she questioned me. I quickly examined the appearance of this girl. She had massive boobs and wasn’t afraid to show them. She wore a floral top with a very low v-cut. It was evident that she wasn’t wearing a bra as her nipples were semi-hard. This particular class was a mixed grade one, so I was positive that she was a senior. Her boobs didn’t tell me that, but the excessive makeup, the “beautiful” tattoo on her collarbone, and the lip ring did.
“Y-yeah,” I stammered, debating whether or not I should lie for a moment. I feared that virginity could be smelt, and I didn’t wanna embarrass myself any more than I probably already was. I was a virgin and the only real kiss I’ve ever had in my life was from my friends who needed practice for when they decide to kiss their boyfriends.
“I’m sure you’ve heard about his craziness, right?” the girl asked me, to which I slowly nodded. “Yeah, but what does that even mean?” I wondered aloud to her.
“Well, if he’s serious about you, I’m sure you’ll find out. Just brace yourself, love, it hurts. Physically, and mentally,” the girl informed me. As if the bell had been a paid actor, it went off after that sentence. Unsure of what the girl meant, I chose to pocket the conversation and keep it zipped up forever. I know all about the snobby, jealous girls that get mad about you getting the guy everybody wants. She’s probably just mad that it’s me, and not her. Right?
I started dressing super provocatively for Ben, because of two reasons. One, that girl that I’d encountered that was dressed like a total slut seemed to have experience, and two, Ben and I were stagnant. It was the same old hug, walk to class, and eat lunch together. I was over it by week five of us doing this. School would be out in a week, and I hadn’t even had my first real kiss with a boy yet! All I had to my name was a love for porn and a roaming finger.
After telling my best friend, Kasey, about my feelings towards Ben and my “frozen in time” romance, she privately confided in Ben without my knowledge. I wasn’t mad at Kasey however, because, by the time I found out, it had turned out to be a good thing. On the last day of school as we were all saying our goodbyes, Ben gripped my entire neck with his massive hand, which was twice my size, and stuck his tongue deep down my throat. He seemed to figure out that I didn’t know what I was doing, as he licked around my mouth and sucked on my still tongue.
“Let me take you to my house,” Ben whispered in my ear. I texted Kasey, unsure if I should do it, and she encouraged me to.
“It’s now or never, you never know when you’ll have this chance again. Go!” Kasey encouraged.
Ben was a junior, heading into his senior year. I was a sophomore, about to be a junior. I assumed he wasn’t a virgin, given that he was a really good kisser and what I’d been told about him that day in class. I wasn’t exactly assuming we were going to have sex anytime soon, but, just in case, I had been steadily shaving my pussy for the last month.