016 - Secret Boyfriend
May 1st, 2014. Away I go, back to Florida. My sophomore year was officially over, and off I went. That year was so strange. The place I escaped to first had now become undesirable. Call it wanderlust or withdrawal, rambling or retreat, the rope I had tied to pull me ashore had begun to drag me deep under the surface.

Over time, **** Lake became a haunted place. A time capsule of bad memories and squandered years. **** was becoming that too, in its own way. I was about to be an upperclassman, and all I wanted was a reset button. Some way to start over. Florida was the closest thing. I had become averse to going out or partying; I was going to the gym so much that alcohol began to represent nothing more than empty calories and wasted time. The winter that year was also the coldest I can remember, so that helped seal the deal on many a Friday night.

Instead, I spent more and more of those nights staying up talking to V. Getting to know more and more about her. V’s a Scorpio, to the T. Fiery, stubborn, not-so-forgiving at times, loyal, and a rather sexual being. All but the latter-most of those traits didn’t pose much of a problem, but the last was — as you know — effectively outer space to me. So I lied about it, shocking, I know. I was incredibly taken by V, and our connection had only continued to strengthen after I visited the first time. I left a note for her parents on the table, thanking them so much for their generosity, among other things. Apparently they were so moved by it that her dad even choked up while reading it.

Her tone began to change and I even received a couple “I miss you” texts over those two months. I had to lie to her about my sexual history. The alternative was coming clean as some meek virgin who crisscrossed the country to come see her. You get the idea. The poor kid, the fat kid, the loser, the no-life, the unconfident, the unwanted, the unloved, the unworthy — those labels had hung around my neck my whole life, suffocating me and keeping me from ever feeling comfortable in my own skin or my own story. There was no way I was going to let my lack of sexual experience scare V off. Which it totally would have.

It’s not like I wasn’t prepared, either. I had been fully committed to doing my best to catch up over the preceding years. I remember finding Reddit threads like “What do you find most attractive about the opposite sex?”, or “What non-sexual gesture makes you swoon?”, and reading the female users’ replies, for which rolled-up sleeves and putting your hand on the small of their back to guide them through a crowd ranked highly. I sought out what women liked, both inside and outside the bedroom. I knew that one day I’d enter the arena of sexual intercourse and I’d be damned if I wasn’t going to make the best first impression I could.

A lot of people’s first encounters with sex are awkward, intimidating, and short. As time dragged on, and I neared twenty — rightly or wrongly — I felt the goalposts moving further and further. The social acceptability of my situation was dwindling more and more as time wore on, and as a man, there’s a lot expected of you. I did all I could to be ready to meet those expectations.

I don’t remember a whole lot from that two-week trip in May. One evening, I have no idea how far into my stay it was, laying there in her bed, V turned to me and asked
“What do you think about us, well...being boyfriend and girlfriend?”

SKKKRRRRRRTTTTTT

I was dumbfounded. I never even remotely considered V might be the one to break that ice first. I ecstatically voiced my support for her idea, and let her know for the first time how I truly felt. One thing lead to another, and luckily I had been presciently hopeful enough to put a couple condoms in my suitcase.

All in all, I’d objectively say I gave a satisfactory first showing in the new frontier of sexual intercourse, but it wasn’t without its share of stumbles. Being the consummate gentleman, I prefaced penetration with oral sex. I’m sorry for the clinical terminology, but there’s really no sexy synonym for cunnilingus — eating out, going down, giving head — they all seem excessively blunt or juvenile to me. Whatever you want to call it, it was short-lived. She pulled me away and said it felt weird. Welp, I guess my research had mislead me. I will fully admit that I probably wasn’t the Michael Jordan of clitoral stimulation, but I had done the assigned reading, and gone over the material a couple times. Wikipedia had helpful diagrams.

With the previews fast-forwarded, it was time for the feature film presentation. With the sole focus of hanging in there like the kitten-on-a-branch motivational poster, reciting the names of presidents in ascending chronological order to distract myself, I am pleased to announce that there was no incidental release on my part. Instead, maybe fifteen or twenty minutes in, V just said

“Whenever you’re ready, you can finish. Don’t worry, it’s not happening for me.”

Well this wasn’t on the study guide. I had a rather realistic view of sex — it wasn’t a thirty-second scene from a romantic comedy, nor was it the hyper-staged world of pornography where some girl exclaims her “orgasm” to the world with a boom mic six inches above her head and a guy who smells like stale cigarettes thrusting a camera in her face under bright set lights, while she fails about like an electrocuted fish to entertain the absurd fantasies of ignorant male sexuality.

It was my first question after things wrapped up: was it me, was it something I did, what can I do...but it wasn’t. V informed me she had never had an orgasm. Ever. Not with a partner, not with a little bit of healthy self-exploration, I was shocked. Not even on your own?

“No, I think I get close, and it feels like I really have to pee, and then my arm always gets too tired.”

She told me the closest she had ever been was one time when she was in Milan, a little drunk, and this really hot — and apparently dexterous — Italian guy demonstrated his manual deftness in the bathroom stall of a night club.

I didn't know what to think. It was like my bar-mitzvah happened the same day as the 2016 election. Congratulations, you’re a man now — wait, what the fuck? He actually won?! There was no time for celebration, we had to figure out what the hell Russia was up to — collusion! Meddling! Voter Fraud! Was it my responsibility to figure this out? Did it lay on my shoulders to deliver her that tsunami of oxytocin like a carnal courier? Is it Prime Eligible?

I was too embarrassed or afraid to ask, and in my own hubris, assumed it my duty to liberate her from unfulfilling fornication. Hindsight is 20/20, and in reality probably much sharper than that. Caught up in the emotional maelstrom of young love, I made a lot of mistakes. Necessary ones. Lessons I’d have to learn at some point. Lessons most people probably learned far earlier than I did, but no matter. The nominal nature of our relationship changed things. But it also didn’t. We were dating, but we weren’t. Remember that surprisingly-liberal sleeping-in-the-same-bed thing? Well, that only worked with the plausible deniability of me as a platonic friend, not as her boyfriend. So to her family, for our own sake, the relationship had to be secret.

That was hard for me. Sure, when I was in Michigan, I could proclaim to the world my love for that woman. But even out to dinner alone, if we were somewhere someone might recognize here, covert once more. Behind enemy lines. I’d tempt fate, stealing little kisses when her parents were out of the room, or holding her hand in public — things that V sometimes didn’t mind, but would other times frustrate her in a playful way. I had built up two decades of romantic resources that longed to find an outlet. And unfortunately, the flow of them was limited when we occupied the same space as her parents.

The sexual side of things became complicated as well, V often being worried and stopping to make sure there wasn’t the sound of footsteps downstairs, or that the bed wasn’t creaking. It was like having an Associate’s Degree — sure, it’s something, but also not exactly a crowning achievement. That deep connection with someone, that affirmation — I finally had it, but with an asterisk. Like a timeshare. A relationship on eggshells. It was nobody’s fault; it was simply the nature of the situation. If I was seen as a suitor, that whole place would’ve been locked down. If I had been found out, that would’ve been curtains. If we had been caught in the act? Lord have mercy.

V was always my girlfriend to everyone in my world. But in her world, I spent most of the time as her friend, like a sucked-in stomach, waiting to be alone so I could relax and let it all hang out. The secret boyfriend.

Covert courtship aside, our relationship brought us much closer together, and dissolved the barriers from before. I would get to know who V was, I would get to know her story. I would learn just why she did the things she did and where her fears came from. I’d learn more about myself; I’d feel free for the first time. Empowered, confident, valued, attractive — all thanks to V.