Sunday, May 25, 2008


This post is dedicated to the anonymous reader who left this comment: "Seems like every other post is about booze, pot, or music. Where is the sex?"

While I have made the conscious decision to not blog about my more recent sexual exploits, I will share particular experience that occurred last July. Previously, I posted a brief summary of the hot shit that transpired, but since it seems that all I post about are boring things, let's take a deeper look back at the Hottest Night of My Life.

If graphic depictions of guys having crazy sex bothers you, this would be a good time to hit the refresh button on your browser.

It was a hot, humid night last July, and although the beer in my hand was cold, watching the Cubs game while laying on my leather couch in an un-air-conditioned apartment was less than satisfying. Thus, I opted to watch the rest of the game at Crew.

Seeing as this was a night game on a Thursday Night my plan was to have a few pints and go home early. However, my eye was drawn to a tall, good looking frat boy type. Since I wasn't "looking" I remained perched on my bar stool and sipped beer while cheering on the Cubs.

After about 30 minutes, the hot frat boy guy hovered near me and tapped me on the shoulder and asked "hey man, do you shoot pool?". Why yes, yes I do. We introduced ourselves to one another and he got $5 worth of quarters. At this point I'm thinking "holy shit this is awesome, this guy is hot as fuck but this is probably just a friendly thing.

And it was. Half way into our first game he asks me if I'm single and I say am but when I pose the same question to him, he responds that he "kind of" has a boyfriend.

Upon further questioning he reveals that his "kind of" boyfriend is his Crew coach that he fucks from time to time. he wants more of a commitment than his coach/fuck-buddy/BF is willing to offer, and all of a sudden I thought that I was transported into some sort of bad plot line to a gay porno.

Crew guy proceeds to ask me why I'm single. He tells me that a good looking guy such as my self [blushing at this point] should not be alone and that any number of guys would consider themselves lucky to be with me.

Seeing as he was drunk I shook this praise off as him humoring me. But then he announces that he is going to find me a guy to go home with, that very night.

"Let's ditch this place and hit up Boystown" he says, and we do, eventually arriving at good ol' Sidetrack. But since it was close to 1AM on a weeknight, the place is fairly dead.

He encourages me to approach several guys, and though I do, I find none appealing. At one point I remarked, "why would I want to talk to these other guys, I'm already talking to the hottest guy in the room".

He smiles, we finish our drinks and leave. He gives me vague directions to his friend's place but we can't find it, and agree to go back to my place.

Within seconds of entering my apartment he grabs me by the back of my neck and we start making out. I lead him towards my bedroom while taking his jeans off, and responds in kind. Tongues everywhere on each others body and soon we're both naked and sweaty due to the lack of A/C and sheer lust.

"Get 2 ties and a t-shirt" he says. "For what?" I ask but do it anyway. He uses my old Brooks Brothers tie to tie my wrists together behind my head, another shitty tie from Target to tie my ankles together and then blindfolds me with the t-shirt. He then goes down on me and gets me close, but then backs off and says "OK - nice to meet you, I'm taking your keys, wallet and cell phone, good luck getting un-tied".

For a moment I panicked, trying to get loose from the tight knots he tied, but I can also still sense that he is still in the room and watching me squirm. After about 30 seconds I decide to lay still and he busts out laughing saying "got you!" and un-ties me and removes the blindfold.

We make out a little bit but in the process I grab a tie and get his hands together behind he head, turn him over and fuck him for at least 30 minutes in an assortment of positions, eventually firing my cum all over his hot body.

Both of us spent, breathing deeply and covered in sweat he goes "I want to show you something". Still in a daze i ask what and he responds that he really, REALLY wants to show me his Crew Uni. I'm again thinking this is something out of a porno, and decline, seeing as it's 3AM and I have go to work in the morning, but he refuses to take no for an answer.

Exhausted, but curious I drive us over to his place, letting him smoke in my car on the way (I don't smoke in my car, but seeing as I just fucked him, I didn't car). We arrive and gets out of my car and says he'll be right back. 10 minutes later he's back in my passenger seat, dressed just as he was before.

Then he unzips his tight jeans, and takes my hand, placing it on his now Lycra encased thigh. "Feels good, right?" is perhaps among the most redundant questions I've ever been asked.

He then removes this jeans, we make out and then he abruptly stops, opens the car door and gets in the back seat of my car. Keep in mind that I drive a small Japanese hatchback.

I'm thinking this is not practical, but then I'm also glad I brought a pocketful of condoms with me. We begin to awkwardly fuck in my backseat but it was then getting light out and doing what we were doing, parked on a residential street was not a smart move.

"I have an idea, follow me" and I do while pulling my pants on and crawling out of my car. We go into his apartment building, but not to his place proper. He has roommates, he says, so we enter the basement which is under construction with exposed framed walls and sawdust everywhere.

Improvising with my dick in my hand, I bend him over a saw-horse and we go at it again. I have to cover his mouth with my hand because of the voices he was making, but 15 minutes or so later, I cum again, big time, all over the place, as does he.

We practically on one another at that point but say nothing but breath heavily on each other's necks. It's now 6AM and we both have to work in just a few hours, so we reluctantly get dressed, exchange numbers and depart.

The drive home was bizarre to say the least. Here I am stuck in early morning rush hour looking every inch of a whore, bumping Mos Def and smoking with all my windows down. I didn't get much sleep night/day, probably less than an hour, but I still got to work on-time, and damn if I didn't have a stupid grin on my face the whole day.

I still have his underwear...


dollar said...

Hi Justin--

Sean Cody is calling--wants to know if he can buy the rights to your story for his next video.

borg_queen said...

Why, oh why, did you torture us by not including all the details on the first post?

Anonymous said...

Love it!

The New Me said...

I don't think your posts are boring at all. But THAT was inspired.

james said...

" (I don't smoke in my car, but seeing as I just fucked him, I didn't car)"

(the rest was just plain hot.)

jason said...

Lucky you!
July is coming up again, you know.

fred said... I'll never look at a saw-horse the same...well done

ex-roomie said...

EEEEEEW! So that's what was going on while I was out of the country!


Anonymous said...

Thanks for the story Justin, you should definitely rethink your policy of not telling us about your sexual activities within the last 12 months.

dwight said...

hot! Man, I was in Chi this weekend and a friend of mine thought he saw you walking down Halsted. I wish he would have pointed sooner so I could have put a face to all this cum shooting. ;)

Speedy said...

so I met this 22 y-o hepcat from Chi-town who wants to play pool again . . . we've already had two "pool" nights and they always end in bed . . . is this what all the hot guys in Chicago do, or what?