Mr. Highschool Crush

It's crazy to think this even happened. It was just a smidgen over 10 years of friendship, a few awkward sexually tense moments and a regrettable night at my apartment.

It all started at my suburban Asian populated high-school north of Toronto. We weren't so north that we felt "out of touch" but we were north enough to come off corny as fuck socially (out of the burbs).

I honestly can't remember how we met in high-school but I do remember where we started to become good friends. It was our church youth group... I spent a blip of time participating in because I was encouraged by a friend to go. It was there that Mr. High-school Crush and I began our friendship.

The first years of knowing each other were pretty casual, not remotely intense. He was a few months younger than me, very tall, very funny and very good looking. He had the whole Tommy Hilfiger model meets Sean Jean model look. Mister urban styled with a traditional boy next door look and possessed ridiculously full lips.

Bah what a shame. Sex ruins a lot of things and it just happened to be this friendship.

There were years of long nightly phone conversations, platonic hanging out when time allowed it. A few relationships sprinkled in between and we were very sympathetic to each other through fairly private challenges. But through it all there was this tension, sexual tension that I guess came from our chemistry.

Towards the end of High-school we had already kissed, there had been a few sexually charged brushes with one another in between relationships and even still our corky friendship was in tact.

As I grew older and very comfortable in my 20s I always felt as if our friendship got in the way of our sexual connection. In other words, I just wanted to mount the dick LOL. Once I finally accepted that's the next step I wanted to take, I paused to revel in my thirsty behavior. I was extremely open about how attractive he was and how esessentially I wanted to "turn him out"... but by the time I had truly started to mean my impulsive thoughts he had found himself in a very serious relationship. She wasn't spectacular, fairly boring, not remotely his fantasy...but that's who he wanted. So I began to back pedal sheepishly away, in the platonic direction. Avoiding all sexual tension and dodging any opportunity to corrupt our time spent.

Mr. High-school Crush grew bored of our platonic friendship and started to show signs of his own "thirst" as well. He opened up about his relationship...the ups and downs. And just as I thought, he was growing bored. I was supportive and told him to stick it out if he really cared for her and he agreed. But then something happened, that required a break. He was single again and I was in the friend zone doing what I do best...Me.

He started going out more with his boys, spending more time in the city and wanted to spend more time with me. He'd come by my apartment downtown and it would be visits filled with nothing but laughter and random stories of our work lives. I even had him model in my fashion shoot I put together for a business venture once upon a time. As my new friends wanted to know more about my very single Mr. High-school Crush I grew protective spewing phrases like "we have history" or "beat it" all in good fun of course O:-).

And then it happens. Weeks of subtle flirting, being unavailable to hangout and multiple pictures of my curves posted daily on bbm (pre-instagram) ignited bold initiative from Mr. High-school Crush that I had yet to see.

I was out and about with other friends when I missed his call and received his follow up text.

"where you at?"

I responded a few minutes later via text telling him "I'm out with people", he asks how it's going and if I'll be heading home soon.

I respond without a second thought of his intentions as I would with a girlfriend and somewhere in the response I use the word "eventually". He goes mute via text and promptly calls me again a few minutes later. This time I pick up and ask him what's up...he keeps it short because he's not alone, the background music is loud and shares he wants to stop by my place.  There was something about his voice, his tone...I couldn't put my finger on it but I told him that was cool and just to text me when he wanted to come.  

That night, I was tired and strolled home fairly early thinking Mr. High-school Crush might even flake. And by flake? Get too drunk to remember he wanted to hang out LOL. I was wrong. As I was lotioned my legs, watching parts of a Kardashian marathon he calls. It's about minutes to 10 at this point and he sounds pretty lucid. He explains he's not far, was at a friends house-warming and he's on his way. I'm still very chill, not suspecting too much I tell him that's cool and to text me when he's out front.

I throw on a pair of lulu's, a tank, take down my long stripper weave and let the wet wavy ringlets lay on my shoulders as I decided whether I need to put on a pair of socks or not. Before I could decide, my buzzers calling my phone. The bugger didn't text me out front. So I let him in my building and before I knew it… I'm greeting Mr. High-school Crush sans makeup and damp weave.

He automatically hugs me and as we pull away his hands drop from my waist down to my butt. He pulls my ass back into him and our pelvic bones are touching as he invades my face with his gargantuan lips. Is this really happening?! Wtf?! I taste no liquor on his tongue as he tries to clean my palate with his. So this was premeditated behavior in a lucid state!!! I just stop thinking and go with it. I end up guiding him and it happens. After 10 years of friendship, flustered almosts and flirty exchanges we... finally fuck. And I learned more about my friend that night and morning than I was prepared for.

Our sexual chemistry was there, but his experience showed. He had slid his regular sized dick in one too many inexperienced starfish and had no clue how to handle me. So of course I handled him. It was great being the sexually dominant one even though I didn't initiate it. A few rounds and as the sun rose we knocked out.

The next morning I woke up before him and of course I wanted more so I "got him in the mood" before he even woke up. There was one more round of sweatiness that was a prelude to utter foolery. As we finished our last round, the pillow talk started. In fact, this was the first real conversation we were having since he walked through my door. He tells me how stressed he's been and shares a few family issues that threw me for a loop. Nothing too crazy but enough to warrant pity. I offer up a back massage, as I reassure him that everything will be fine and the freaking out ensued. He begins to say how he regretted coming over and that he feels horrible doing this to his girlfriend. My stomach sank not because I was hurt or felt used...but because I just wasted one of my sex numbers on someone I'll never fuck again!!!!!!!! You know that Dave Chappelle skit where he talks about bad dancing making his dick soft? Well I could relate. Because all this post sex pillow talk made my theoretical dick Hella soft!

I masked my annoyance and disgust with being supportive. I gave him platonic advice about his situation. Putting my feelings aside and acting as if our exchange didn't just happen, I totally removed the image of us being stark naked from the moment. I ushered him out of my apartment nicely but swiftly, I felt it was appropriate since his phone was ringing off and now finding out he was no longer on a break from his girlfriend I knew exactly who it was.

After this, our friendship dynamic totally changed. He wanted to have sex again and I wasn't having it. We'd have our days where we could keep things totally platonic but the moment he felt too comfortable he just wanted more pink. Our friendship was strained significantly once he proposed to his girlfriend only months after what happened and was still trying to hit it after the fact. I grew tired of the back and forth between our platonic conversation and his lustful thirsty attempts.

After growing distance gradually and him flaking on my birthday I was over it. And before I knew it this cat had killed not only the curiosity but our friendship.

Mr. High-school Crush is a friend I miss but realize a friendship that'll never be rekindled. That experience taught me never to mount any of my good-looking friends again no matter how great the chemistry. And to be mindful of my sex numbers, cause a bitch can't lie! lmao