100 Guys, 100 Stories

The Diary of an Awkward Gay Boy

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#3 The Guy with Two Kids…Who’s Roommate I Fucked

So I honestly forgot I started this blog. I got really busy with college and life and all that is between. I saw the counter I put on my page and it’s almost at 10,000 views!!!! What?!!? And I have almost 100 followers now. That’s incredible. Well I graduate from college on Friday and I have FANTASTIC news! I just got a job as a flight attendant!! I start training soon and I am so ecstatic! Anyway I guess I’ll get to the story. I just met a guy who is stunningly handsome and built like you’d never even imagine. Why he likes me I will never know!

Seriously? What is my life?

So we met on one of those dumb gay apps that rots your brain and wastes way too much time. So we planned on just having sex, because let’s face it, that’s what those apps are for. I never imagined that after the best sex of my life that we would be lying in his bed talking about our lives and just going on and on about everything. It was so refreshing to talk to a real person when all I usually find on those fucking apps are jerks with big heads and small dicks. I soon find out that he had two kids, a boy and girl, four and three years old respectively. AND GUESS WHAT!? Their mother is a flight attendant.  Crazy right? So he pretty much schooled me on my airport codes since he was married to a flight attendant for 5 years and has travelled the globe with her.

It’s only been three days since we met and yet I feel so comfortable around him.  It’s more than strange. He’s even talked about visiting me when I move away in a month for FA school.  I’m not sure what to think anymore. He’s 31, I’m 21. What does that mean? Should I run away because of a number? Or because of the two kids? I am at a loss for words, but all I can think about is how he made my body tremble like no one ever has.


I forgot to mention that as we’re laying on the couch, in our boxers, watching Donnie Darko, his roommate walks in the door. Little did I know…the guy I was talking to in February, who I may or may not have hooked up with, is his fucking roommate…and ex of over a year and a half. I about shit my pants. Like how the fuck do I get this unlucky? At this point I don’t really care anymore. I just think it’s funny that he has to sleep in the room next to us and hear us having loud passionate sex. Lol

Well, that’s just another reason why my life is fucking weird.  

Filed under gay relationships 100guys100stories blog my life fml flight attendant what the fuck gay man gay guy college sex grindr traveling gay boys Gay boy problems donnie darko hook up hookup awkward diary boyfriend

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Anonymous asked: now chile you better be updating your previous story because i was getting my life from reading that. flawless blog, so relatable ~

I’ll throw in updates as I get them, for instance the barista has been poking me on facebook more and just commented on one of my statuses today. eeeek!!!

And thanks for enjoying it :) More to come!!!

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#2 8 Years and 400 Miles

January 6, 2013

I don’t even know where to begin at how fucked up this story is. I guess I could start off with the fact that this guy is really cute, has multiple degrees, has a great job, and is a complete gentleman, but if that was it then I guess I could just stop typing now. If that was the end of the story…well then it wouldn’t be my life.

A year and a half ago is when we became Facebook official friends (whatever that means). I’m not even sure why I added him. I didn’t know him. I had seen him out at the club once or twice and I thought he was cute, but I had never said a word to him. Fast forward to last week and it’s almost like we’re strangers. You know that app? The gay one? Grindr. Yeah, we all know what it is, and yes it’s used for many reasons, hooking up, dating, friends…etc. Well, last week we exchange our first words…on Grindr. Just a simple “Hey”, “How are you?”, “You’re cute.” kind of messages. That’s when we recognize each other. So the next night we make plans for me to come over, watch a movie, and have some dinner.

Cruel Intentions

When I pulled into his driveway the next day I got this strange feeling like I had been there before. I cautiously walk up to the door and knock a few times. Between the time I knocked and time it took him to come to the door, in that 15 second window, it hit me -kind of like what concrete would feel like if someone threw me out of an actual window. Ihadbeen there before. Just once. About 7 months prior. I’m not completely proud of the reason I had been there before. It was for a hookup. We all have a past, we all want to have some fun, and we also have those moments that we feel alone. On that summer day I was meeting a guy, but the guy I met was not the same guy who was about to open his front door and greet me…

He opens the door and I push the thought to the back of my mind, because if that’s all I can think about I’ll probably be acting like a complete and total spazz the whole time. After a couple drinks and a bit of conversation I figured it out. The guy I had met over the summer was indeed his ex. It wasn’t hard to put the pieces together because he mentioned his ex a couple times and mentioned why they broke up, because he was cheating on him.

He then gives me, the most indecisive person on the face of the planet, the task of picking out a movie. Luckily, his tiny collection of old DVDs made it much less difficult to choose. So I see Reese Witherspoon and Sarah Michelle Gellar on the cover an old 90’s movie and I’m SOLD. I mean what gay man doesn’t have a girl crush on Elle Woods and Buffy the Vampire Slayer?? Cruel Intentions, the name of film, never seen it before and it turns out it’s his favorite movie of all time (his favorite movie soundtrack, favorite actress, based in his favorite city, and it has his favorite car in it, a Jaguar XK140 Roadster). But let’s be honest, the title couldn’t be more spot on.

I can barely pay attention to the movie, partly because the guy sitting next to me is really cute, and yet all I can think about is how I had sex with his ex-boyfriend…in the same house. Again I decide that now isn’t the time to bring that up, I like the guy and I don’t want to scare him away by spilling my deepest, darkest secrets on the first date. I’m not sure we actually finished the movie, because by the end we were cuddled up next to each other in his bed, about to fall asleep, and I realize that 90% of our clothes were on the floor. At that point I suppose it was decided, I was spending the rest of my night and the next morning curled up next to him.


The morning comes, and no, I’m not curled up next to him like I envisioned. I’m at the edge of the bed with one arm over the side and my legs turned sideways diagonally across the bed, looking extra classy I’m sure. It’s 9 am on Sunday morning and we both kind of look at each other like, fuck this, I’m tired and I want to sleep in. So we squeeze back together and stay there until 12:49pm. 0 fucks were given.

Yeah, I know it’s lunch time, but he turns to me and asks, “How do you like your eggs?” I think about it for a second and go with what’s easy, “Scrambled I guess.” Then he smiles a crooked smile, “Good because that’s all I know how to make.” We laugh a little bit and finally get out of bed, but that goofy crooked smile is all I can see in the back of my mind.

I still wasn’t completely sure how to process my feelings when I left his house after breakfast, but somewhere on the drive home listening to some Lana, I decided I wanted to see this guy again, and again, and probably some more after that. And that’s what I did, I spent 3 more nights with him during the week and I finally built up the courage to tell him the truth about me and his ex. That’s a story within itself. I’ll save that for next week.

He seemed perfect, if it wasn’t for a few small details I left out. He’s almost a decade older than me, and this morning I drove 400 miles away, back to college. Winter break is over; it’s time to go back to the real world.

8 years and 400 miles separate us now, and I’m still not sure what to do.

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#1 The Barista With a Boyfriend

January 1, 2013 

The past few months a certain barista at the Starbucks closest to my home has been poking me on facebook. A lot. Not just that, but the liking and commenting and miscellaneous flirting. We recently exchanged phone numbers and one night I may or may not have told him I thought he was extremely cute. 

First mistake.

A few days later we finally start texting again and we make plans to see Les Miserables (even though I’ve already seen it). I show up at Starbucks to meet him and I have to wait one complete hour for him to finally come out. I honestly thought that he had stood me up or was trying to play some cruel joke on me since I knew he had a boyfriend etc. By the way, I wasn’t planning on any funny business…I just wanted to see what happened. So after waiting an hour, drinking and entire venti tea, and peeing twice, I decide it’s time to leave…I’ve had enough. (During this hour he kept saying that he was about to come out from the back and that I would laugh at the story of why he was taking so long) Fed up, I drive across the street and pretend to get gas at the store. I know this sounds stupid but to me, it was me giving him one last chance to redeem himself, which he did. I was over there for maybe 2 minutes when I feel a buzzing in my cup holder and it’s him asking where I was. Relieved, I quickly drove back over and he meets me at my car. I was too embarrassed to go back inside. His story wasn’t that funny, and I was completely unamused. But the fact that he wasn’t playing some sick practical joke on me made me feel less anxious and bothered.

We show up to the movie theatre about 45 minutes early because we decided we weren’t hungry enough for food (mistake…our stomachs growled the entire 158 minutes of Hugh Jackman’s vibrato). We sit and talk about our lives and our little quirks and he’s making me fall for him every second. I can’t help it. When we finally go into the correct theatre, I say this because it took us three tries to find the right one, we sit down and endure the 20 minutes of previews. You know, it’s hard to concentrate on the opening scene of the movie when all I can think about is the fact that the arm rest is still up, nothing is separating us but a few inches and the bare skin of my fingers. I want so much as to hold his hand, or to just rest my hand on his thigh. Finally 30 minutes in to the film, I build up the courage to do it. I clumsily throw my hand on his leg and pet it…almost like a cat. 

What was I thinking? Am I out of my mind? He has a boyfriend!

He makes a strange movement that tells me he obviously wasn’t expecting it and didn’t reciprocate the feelings. So I awkwardly pretend to crack my knuckles and remove my hand from his thigh. I sat for the rest of the movie, the next TWO HOURS, in silence; wishing I had never moved my arm and wondering what was going through his head.

The movie finally comes to an end and we both have to use the bathroom. So what do I do? As soon as you goes up to the urinal I walk up to the one right next to him…how in the hell can I be so fucking awkward? It things weren’t weird enough. So I have to stare blankly at the wall and pretend I was not curious at all as to what he was packing down stairs (every gay man knows they wonder!). We walk out of the theatre and our hungry stomachs decide we both need McDonald’s. They are pretty much like Starbucks in New York City, there is one on every corner. Fat fucking Americans. We sit down and the talking continues. Not a single silent moment. The kind of conversation I dream of having with a guy - when the conversation just flows and the subjects change faster than one of Taylor Swift’s boyfriends - that fast.

By now we’ve spent the past 6 hours together and I almost regret that I gave up on him at first. But I know that no matter what, he saw this date as nothing but a friendship. It hurts…but I know it’s true. So I drive home, alone, with the windows up, listening to demo version Treacherous on repeat, deciding if I should just get really high and forget about the events of the day, or just accept them and hope for a better chance next time. I chose the latter. Looking back, I haven’t decided if I chose the right one.

Here’s to 2013, this hope was treacherous, this daydream was dangerous, and I kinda liked it.

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I’m 20, I’m gay, and here’s my story.

Now that we’re starting 2013, I have had the chance to look back on a very scandalous 2012. I have also looked back on those awkward hookups, the times I thought I was falling in love, and the times where maybe I did.

Starting the new year I’ve decided it’s time to write it all down. A year from now I’ll look back and I guess you can be the judge. Did I find love or just another crazy night?

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