The First Cut is the Deepest

For a long time, whenever someone asked how many people I’d slept with, I would say it with a half, like 3 ½ or 7 ½, depending on how many it was at that time. This wasn’t some sly reference to sleeping with a small person, or a person with a small penis, even though he did have one. It was how I equated the disappointment of my first time with a number others could understand.

To be fair, I don’t regret losing my virginity. It was my choice. But could I have made a better one? Probably. However, that would have required the wisdom and experience that only came after I did it. Virginity is often a catch-22 that way. But as I said, I don’t regret it, because for better or worse, it set me on the path I’m on today.

When my high school crush, Duke Ashton, passed on taking my virginity and then subsequently graduated, I was left as a senior with few prospects, or rather few that I would entertain. Eventually, I would chose Brock Bishop, a bisexual boy with a big nose. To understand this choice requires a background of my high school friends.

Friends were not, and have never quite been, my strong suit. By high school, I’d had the same best friend since 4th grade. Then, in sophomore year, I met Lily Dunsten when I joined the school newspaper. She was, in one word, infectious. Loud and opinionated with an older sister in college, who kept her up to date on all the best bands and indie movies, she was the kind of creative friend I thought I should have. However, Lily also came with a lot of drama, which, despite knowing me for such a short time, she unloaded on me each morning during our arts and humanities class. One of the first things I realized about Lily was that she was not a virgin in any sense of the word and this was from where a majority of her drama stemmed. When I met Lily, she was dating Brock Bishop, but also sleeping with her best friend’s boyfriend, who after his parents kicked him out, lived with Lily’s family. At the time, neither of us was even old enough to drive and somehow, she had a narrative going more intense than my mother’s favorite soaps.

To a degree, like my mother and her soaps, I found Lily’s exotic and complicated life very entertaining. That she also found my advice necessary to navigate such complications made her even more endearing. I had never had a relationship or sex, and I was caught up in my own personal demons, but Lily needed me. It was an escape and it made me feel extremely close to someone, which I, in turn, needed. It didn’t take long for our social groups to merge, her group of eclectic friends (including Brock and the best friend who’s boyfriend she was boinking) and my academic team/IT boys (including Duke, Elijah, and Stark). For a while, things were good and Lily and I were anchor points. But by the end of sophomore year, Lily’s infidelity became public knowledge and grudges and alliances began to form in the hierarchy. Yet, no one stopped being friends, which actually in the long run made things more difficult.

Gradually, the secure place that I felt in the group began to wane. I began to feel like the tagalong, more often left out than included. If plans changed, I was rarely informed, thus late and left behind. When we left the lunch room, they were offended if I didn’t wait for them. Yet if they finished first, I was often running down the hall to catch up. These infractions were petty and small, but over time and with increased frequency, they fractured a part of my evolving psyche that was already at risk. I felt even lesser than that I already did. There’s a reason people hold on to the hurt caused in high school, no matter how long ago or how small. In those years, we are forming the foundations for ourselves as individuals not just as our parent’s children. What is done to us then, will have ramifications for the rest of our lives. Sadly, most teenagers are oblivious to this power, as my friends were.

Then, something happened that for a moment almost restored me. In another sweeping act of drama, Lily became a lesbian in our senior year. She and Brock both came out actually, he as bisexual and her as gay. He continued to be interested in women mainly, but Lily began dating one of the butchest girls I’d ever seen. None of this particularly bothered me until Lily wanted to talk about going down on her girlfriend. For clarity, I’d often been just as adverse to when she used to discuss Brock going down on her. But it was her desire to be seen as a lesbian rather as a person that made communicating with her more difficult. Her relationship with Clara seemed more a ruse for attention than an authentic self-discovery. More than anything else, Lily was a narcissist. There was a general consensus that the love of Clara came more from the fact that she indulged Lily’s ego. Whatever the reason they were together, Lily became less of a presence in our group as she spent time with her girlfriend and this seemed to leave room for me to return to my former status as worthwhile friend. Specifically, this brought me attention from Brock.

He was never really my type, but as with Lily, I had a desire for him to like me, maybe because he impressed me that he could pull off girls’ skinny jeans, before they started making them for boys. So, when he started asking me to hang out on our own, I agreed. Brock worked at a gas station just a block from the restaurant where I worked as hostess. When I finished my shift, I would often stop there, wandering with him as he measured the gasoline levels or scratching lottery tickets while he and his friend cashed out the drawers. As the only friends in the group with jobs at the time, it was a nice sense of late night comradery. On one of our nights off, we went alone to see Clerks II in the theater, which as a side note is quite possibly one of the few sequels that was ever worth making. Kevin Smith, in my heart, is still all the rage.

During the movie, I had noticed Brock’s knee touching or hand grazing me, small touches that I could have wrote off as accidents, but I wasn’t that stupid. When the movie was over, he wasn’t ready to go home and he suggested we go hang out in the nearby park as the gates were never closed. With the lack of interesting activities in our pitiful town, the park wasn’t the most thrilling idea, but it was suitable. Beyond that, I was curious where this was going as well.

There were few lights outside of the picnic table area, where we sat first. For a while, we had generic conversation, then very quickly everything veered. Brock’s hand was on my leg, and he was interested in how much I’d ever done. I played it up of course. I’d kissed, I’d had a few hands on my breasts, all true things that I wanted to sound much less amateur than they were. Thanks to Lily’s inability to censor, I knew almost everything about Brock’s history and he was much more accomplished than I was. Part of this made him less appealing, even on top of the fact that I wasn’t particularly attracted to him and his faux Jew fro. Yet, I liked that he was aggressive. His hand gripped firmly on my thigh without shame. He faced me dead on. This more than anything sent my endorphins rising and then, the more I thought about it, I realized that he was my friend, someone I knew well and trusted. This could work for me.

We went to find somewhere with less illumination and settled on the kid’s playground. We climbed up past the monkey bars and swings into the playhouse. He started kissing me. It was adequate. It was fun. I knew I wasn’t going to have sex in a jungle gym, but besides that I was unsure how far I was ready to let this go. Knowing that I was about to do something new, something I wanted, made my heart pound with nervous energy, even more so when Brock reached up under my skirt, pulling down my underwear and tossing them onto one of the climbing rungs. While I wasn’t sure how predominately motivated I was by an interest in him, his interest grew increasingly clear. Eventually, we made our way back down to the ground, where I straddled Brock on the end of the yellow slide. I didn’t want to be a tease but I was uncertain of the next move. Finally, he gently gave me the hint and I took it.

As I kneeled down into the woodchips, I began rehashing every comment I’d ever heard from movies, television, books, and my other lascivious friends. Tight lips, wet tongue, no teeth, try not to gag, swallow always swallow, and for god’s sake don’t literally ‘blow.’ I repeated them over and over in my head. I spent the short time it took more concerned with what I was doing than paying any attention to his reactions or for that matter his penis, which became a prop for my own adventure than any identifiable figure in connection with a person.

In the car ride back, obviously once my underwear had been retrieved, Brock asked me again, “so, that was really your first blowjob?” I assured him yes. “Well, that’s was…good. Really good.” He sort of huffed, propping his forearm against the edge of the window.

“Thanks,” I said, suppressing the urge to do an outward dance. Instead, I just sat quietly, staring out the windshield until we got back to my car.

After that night, Brock did not become my boyfriend. I didn’t expect him to; I didn’t want him to. But we did become something where I relished in his attention and the allure of keeping a secret, which among our friends was a feat. It wasn’t a regular thing either, but at parties here and there, we would sneak off outside or to a spare room and fool around. It slowly became less of secret when he did things like sit with me under a blanket and sneak a hand down my pants while we watched zombie movies at Elijah’s house. But still no one discussed, until it became too overt to ignore.

In December, Brock’s parents were out of town and he invited a few of us over to spend the night. There was food, a few drinks, and both Bill and Ted movies on DVD. Like everyone else, I fell asleep on the living room floor sometime during the Bogus Journey. But unlike everyone else, I woke up at almost 3am. Brock had curled up behind me and, as part of his usual move, was sliding his fingers under the waistband of my jeans. I was tired, but I was down. So, in almost pitch black, I followed him, stepping over our sleeping friends into his bedroom. We kissed, clothes started to come off, and then when he was behind me, lips on my neck. I just said it. He stopped.

“Are you sure?”

I absolutely was. I felt in control. I trusted him. I knew him. There had never been even the slightest pressure from him to have sex. It was my decision. Mostly, I was tired of waiting for some perfect moment that would never hold up. Those girls who wanted candlelight and rose petals seemed like idiots to me, like the girls who were waiting for Prince Charming. Brock was not a Prince. I certainly wasn’t in love with him. But I genuinely thought that with him, this could be a moment I wouldn’t regret for the rest of my life, and that’s what I was a looking for, a memory I could enjoy. And if I’m really honest, the fact that his penis wasn’t that large reduced my anxiety about the whole process.

Once I repeated my request, Brock did not need any more convincing and we strategized positions. We started with missionary and my assumptions about size were proven wrong. It felt like I was being ripped apart from the inside out. I couldn’t breathe, my throat tensed up so tightly. I wanted to scream but our friends were asleep on the other side of the door. My eyes watered. As slowly as he moved, it hurt just the same when he went in the second time. This was not sex. This was hell. And Brock could tell. This time, his penis was not some prop, I was fully aware of its girth, its hardness, every motion inside of me and I wanted to rip it off. I couldn’t understand how my body could encourage this but I was wet, soaking all the way under my back.

He adjusted and tried again. It wasn’t any better. He tried massaging my breasts. Did not help.

“I’ve heard it hurts less from behind,” he said. I didn’t hesitate to flip over onto my stomach. After a couple thrusts, it still felt like I was being split in two. But for about a millisecond, there was a point that I could see how this could get better, it just wasn’t going to be tonight. I almost choked on my relief when he said, “I think we should stop.”

The entire thing had lasted all of 45 seconds.

My pain wasn’t the only reason we stopped. Brock stuck a shirt under the door and turned on the light.

“Holy shit,” I whispered. His room looked like a murder scene. What I thought was a natural reaction to being turned on was really the natural reaction of my hymen to being completely obliterated. A shank through the aorta could not have produced as much blood that pooled and spattered his sheets. His legs were covered. My back and my stomach were covered. I had red, blotchy hand prints on my chest. I helped him take off the sheets to go in the wash. When he flipped over the mattress, the red stain was still seeping through. THAT MUCH BLOOD.

He used the sheets to clean off and went to start the laundry. I shuffled across the hallway to the bathroom and got into the shower. Our friends were not idiots. A couple of them woke up, groggily wondering why I need a shower at 3am. “Because I felt dirty,” was horrible lie but rather than call me out they went back to sleep and so did Brock and I. Embarrassed that I had ruined his mattress and worried the stains wouldn’t come out and his parents would ask (which they did), Brock hugged me and laughed, telling me not to think about it. Still, I struggled to sleep, both from over thinking and the radiating pain from my vagina. Before everyone else got up the next morning, I was out the door. I had promised my mother that if I stayed with “Lisa,” one of my friends who was also at Brock’s, that I wouldn’t be late for church. I was five minutes early.

It was when I sat singing hymns, newly deflowered, that a sense of pleasure at what I’d done finally hit me. As awful as it was, I had taken control of a major event in my life. Afterwards, the pain that didn’t go away for over a week, became a bittersweet reminder. Sitting in the hard desks as school was a new punishment, one that my friends finally commented on. “You and Brock, huh?”

“It’s not a thing,” I said, praying that no one would tell Lily. As she never confronted me in a dramatic monologue fashion, I safely assumed she never knew I lost it to her ex-boyfriend.

Not long after the deed, I let my father know I needed to talk to him. After school, when I got to my dad’s for his weekend, I sat him down and with a deep breath said, “I had sex.”

“Was it good?” he asked without hesitation.


“What? Was it not?”

“It’s was…okay,” I said, not wanting to disappoint him like I had been. “You don’t seem surprised,” I added.

“You sounded so serious, I figured it was this. So, do you feel different?”

I shrugged. I hadn’t changed as a person. I looked the same in the mirror, but I did feel different. There was a little less mystery in the world. I was surprised by the soft melancholy this left in place of my virginity. It’s an almost impossible thing to describe. I am and will always be the kind of person who rushes into something new, any original adventure. Yet, sometimes, once the freshness has worn off, I mourn. It becomes one more thing I’ve already done and one less thing I have to look forward to. There’s a beauty to anticipation that seems oddly underestimated.

While I still didn’t like the phrase, I understood why virginity was considered a loss.


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