Sex in the City: The Tale of All My “Firsts”

In the spirit of Valentine’s Day, I’m about to tell you a compilation of embarrassing stories about my sex life. And while I struggled a lot with whether to make these stories a public reference, I feel like they’re too real to not put out there. I’ve decided to change the names of the (few) partners that I’ve had mainly because their egos are too delicate to handle it. As for me, my ego has been hit enough to withstand the criticism. And as I’ve said before, I’m not afraid of much.

There are a few memories that I have attributed to my now understood prophecy of a traumatic love life. So I definitely have some overdue karma because the universe has been slapping me since the day I got my first valentine. So brace yourself, because you’re all about to learn the cringeworthy details of my Firsts. These stories are the foundations for my humbleness and the reason for my (lack of) sex life.

The very first guy that I ever made out with was in the back of a car during my junior year of high school. Now that might seem late but for the bulk of my youth, I was more preoccupied with my band groupie persona and my “I give no fu*ks” angst to care about teenage boys. But by the time I was a junior, I had dropped ten pounds, dyed my hair blonde and convinced myself that I was now a self identified surfer barbie. Either way, boys were taking notice and I was taking notice that they were taking notice.

So like any great teenage cliche, the bulk of my love life began with Junior Prom. At 16-years, I was a different kind of ambitious. The kind of ambitious that actually believed there was a 16-year-old boy out there willing to serenade me in front of the entire student body. Instead, I got asked to Prom with a pretzel. A subtle metaphor for all the salty boys that would enter my life in the next half a decade.

Just days before Prom, I discovered that my date had spread a rumor throughout the swim team that he would be sleeping with me. Followed by some questionable comments about how I would have to say yes. I will forever be confused as to what delusional boy logic was used to conclude that a mediocre, theme-park pretzel was a reasonable trade for my flower. But then again, a lot of boy logic is missing the logic. So this swimmer learned two lessons: his swimmers wouldn’t be doing any swimming on prom night and be cautious to mess with a girl with a lot of teenage angst. So I ditched my prom date two days before the event and found a new one the very next day. This little story may seem inspiring but it’s actually how I ended up with a gay date for my first prom. So much for that Disney fairytale, right?

But a few days before the dance, my eyes targeted Jake. He was a senior and I had a slight obsession for older boys that roamed florescent hallways. Jake was tan, built and spent his weekends down the shore, surfing. What can I say, I like a guy who fits my temporary personas. So I began to lock eyes with every hall passing and confirmed in my head that he would be mine. On Prom morning, I handed my best friend a nostalgic 90’s style handed-written note with my number on it to gracefully hand off to Jake at his locker. Needless to say, I was in.

We continued a constant flirtionship for a couple of weeks until I finally got the nerve to ask him out. Yes, you didn’t miss-read that, asked him out. TheAmeliaBurns was nowhere near being born and yet she was already more advanced then your basic 18-year-old-boy.

I was unbelievably nervous for my first official date to the point where my entire 4th period Algebra class overheard me venting and began providing advice. While some girls spend hours before their first date curling hair, I was receiving very public dating advice from my middle aged math teacher.

My life has always gone a little bit too much like a movie so naturally I should have been prepared for disaster. Someone once complimented me by saying I was the “lead” in my movie which isn’t always the case for some people. Unfortunately, with being the lead comes all of the comic relief that is needed to make the lead more relatable. So on my very first date, my guy tried to pay and his credit card declined. Second hand embarrassment instantly consumed me but like most boy ego’s it couldn’t just end there. So I continued to stand there while he pressured the frustrated cashier to swipe his card multiple times. (So much for cool senior Jake.) So I paid for my first date.

Eventually, he suggested a drive and we ended up at the lake in the middle of our town. I imagine he must have thought showing me his yearbook was a good topic of conversation. Nothing like high school nostalgia to kill a mood. But then he kissed me; And by kissed me, I mean he slobbered all over me. It was this moment where I realized that “super cool senior” Jake was nothing more than a Saint Bernard with a surfboard. And yet, I agreed to move to the back because he was still cute and I was still desperate to make my surfer fantasy work out.

Now this is the moment that I attribute to all of my future relationships because this is where it began. I should have know my love life was destined for an eternity of comic relief when I looked out the back window into the eyes of an older women who slightly resembled Mrs. Brady. She was so appalled by the site of Jake kissing my neck that she scooped up the 2 pugs that she was walking and ran in the opposite direction.

All Jake and I did was kiss but he somehow managed to bite out my earring, hit my head on the roof of his car and give me a seat belt burn on my inner thigh. Needless to say, this wasn’t true love. And I spent the rest of the year ghosting Jake until the last day of school; where I wrote a sassy note in his yearbook thanking him for “letting me be his last high school crush.” Maybe a little bit of TheAmeliaBurns was there after all. I didn’t see Jake again until two years later at a college party but that’s a story for another day.

Fast forward to my first real relationship, where I’m sure there is an eternity filled with embarrassing stories that are not worth telling. The story about how I lost my virginity however is. On the day that I was going to loose my virginity, I knew it. While most girls buy lingerie for their first sexual experience, I bought a new pajama set with Bulldogs on them. I guess I thought this was comforting and sexy but honestly, I can’t explain the reasoning behind half of my decision making.

So I’m not going to sugar coat it. Loosing my virginity was the most painful experience of my life. It was slow, ungraceful and nauseating. If my middle school health teacher had warned me about this kind of pain, I would have been an abstinent nun before ever agreeing to go through with this decision. But I had little warning and so much of it was intriguing. By the time we were 20 minutes in I was light headed. While I imagine most girls feeling beautiful and empowered after their first experience, I was throwing up in my boyfriends bathroom from the pain. I wish I was making this up. I went home slightly traumatized and angry at Carrie Bradshaw for lying to me.

The first year of sex was just as traumatic. To the point where I finally had to seek out a specialist to make sure that I wasn’t broken. So that’s how I ended up at my first gynecologist appointment.

I expected to walk away from this appointment with a magic pill that was going to transform my sex life into nothing short of a Kate Hudson Rom Com. Instead, I had a gynecologist straight out of That 70’s Show who provided me with the weirdest medical advice I think I’ll ever receive. At my first visit, I had a conversation with my doctor where she attributed my painful events to my long distance relationship.

“Having sex so sporadically  may be contributing to a pain similar to loosing your virginity all over again.” was the statement said to me.

And as if that day couldn’t get any worse, while I was getting redressed my gynecologist entered back into the room and gave me the unexpected medical advice to invest in a dildo. Imagine having to explain that prescription to your mother waiting patiently in the waiting room? Well I did, and she laughed the entire way home.

After years of being frustrated with my sexuality, I was eager to take control of things after my break up. It didn’t take long for me to come to the conclusion that I needed to step up my Sex in the City game and experience my very first one night stand. So that is how I met Michael.

Michael was self absorbed, charming and beautiful. We met at a party during the climax of what had become a terrible relationship. I met Michael because he tried to kick me out of an after party. I was minding my own business when an overcompensating frat boy attempted to pull the whole, “Who do you know here?” front. He was intrigued and slightly agitated by my demeanor but who can really blame him? I’m a lot to handle. But he had little faith in my explanation and actually accused me of lying about my affiliation as well as my own name. I did mention he was a real charmer, right?

Eventually, a fraternity friend came to my rescue which sent Michael into a slight panic as he over apologized for his behavior. As I said, I’m a lot to handle. So rather than just laughing about this misunderstanding, I had to let my alter ego kick in instead. So I purposely spilled the rest of my beer down Michael’s shirt, smirked and apologized as I followed my friends down the steps. I’ll never be exactly sure why but this was the moment when Michael became infatuated with me.

He spent the rest of the night flirting with me behind the bar, mixing me drinks and assuring that he would “keep me out of trouble.” The next morning, I remembered very little but I knew I left an impression because Michael had added me on every social media possible. I paid little attention at that time considering I was smack in the middle of my own Love Story drama.

But Michael was persistent. He threw me a lot of social media attention and talked me up enough to his fraternity that I got a weekly warning from my friends to “stay away.” But we all know that’s the one thing that you should never say to a girl because now I was intrigued.

I dreaded the morning, I was forced to post my Facebook-Single status. A bleak reminder that I had just been knocked off my pedestal. So I was in complete shock when he began hitting on me via my status and asking me to a formal. But I admired the guts. Michael had officially captured the attention of theAmeliaBurns.

I had decided early on that I was ready for my conquest. I was slightly broken and some extra attention from an overly cocky boy was just the kind of superficial confidence that I was looking for. But more surprisingly, Michael wasn’t as cocky once he actually caught my attention. I went from subtle hints to obvious invitations fairly quickly. Finally fed up and frustrated, I offered Michael an ultimatum; He either hang out with me or I’d be done talking to him. So he agreed, and I waited.

It didn’t take long for me to realize Michael was pre-gaming to hang out with me. This was a new one for me. Frustrated, I sent a text “Just come over, I promise I’ll still like you when you’re sober.” To which he replied, “‘I’m not drinking, and I’m coming.” This lie and unknowing pun would prove to only hurt him in the near future.

When Michael arrived, he was much prettier than my fuzzy memory had envisioned and I was at peace with my decision. He tried to play things cool but it quickly became clear that Michael was extremely nervous. To be honest, I don’t think he ever thought he would get this far and at the time, I had no idea the amount of game he had talked to his frat about his “affection” for me.

Later in the night, things were getting hot until panic started to fly across Michael’s face. I was instantly freaked out, pushing him off me and demanding to know what was wrong.  And here was the explanation that I got,

“Yeah, so you know how I said I didn’t drink? Well, I did… And now my body’s not… cooperating.”

So there I was, a girl who had just gotten dumped and my first one night stand couldn’t even get it up. This was not part of my Sex in the City plan and I was pissed. I tried to fake compassion and assured him that this didn’t need to ruin our night. But you know what most frat boys have in common? Their weak and defensive egos. Embarrassment instantly consumed Michael for the remainder of the night and I tried not to cringe as he awkwardly continued to assure me that this had “never happened before.”

That night was easily one of the most awkward experiences of my 20’s and I was relieved when it was finally over. But more surprisingly, Michael and I actually held good conversation. By 4am, I was laughing for the first time since my breakup; And by the very end, I felt like I had gained a friend out of the experience. So when morning rolled around, I was feeling very content when he kissed me goodbye and vowed me to “never mention this night to anyone.

Now this experience taught me two very important things. 1) I will never be the one night stand type of girl and 2) NEVER trust a frat boy with a bruised ego.

Michael would go on to tell his entire fraternity about how he F**ked me and I continue to ignore it while I focused on rebuilding my own bruised ego. But if you haven’t been publicly slut shamed for not having sex, let me tell you, it’s a frustrating and comical experience. I mean come on boys, if we’re gonna throw gasoline on fire, let’s at least make sure there’s a match to light it.

I’d like to tell you that since these firsts, my love life has gotten exceptionally better. But believe it or not, every story that has come after has managed to top these. I used to believe that these experiences would hinder my own self respect but in reality, they have only made me realize how beautifully authentic my own confidence is. And there is something comforting about knowing that each of these brutal memories can be topped.

I understand that this comic relief is what keeps me humble. But they are also a part of the reason why I will always be the lead and never merely the love interest. So thank you boys, for unintentionally making my love life into a feminist manifesto.




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1 Comment

  • Reply Carlita Kelly

    I randomly saw this on my Facebook feed. Loved this. Everything about it.

    February 18, 2017 at 3:50 pm
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