Time to explore! 😝

Well now that I’ve had this HUGE revelation of my sexual orientation and have made it known to myself, it’s time to see what’s out there!! One guy down…how many shall follow?! πŸ™ˆ I have busted down those closet doors!!

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Sunday brunch after a hellacious night of drinking on Saturday? And your friends want to tagalong again? Sure. Let’s do this. Bryan and I venture down the sidewalk on our mile walk to the diner for brunch, hand in hand, wearing our RayBans, looking cute as hell, but feeling deathly on the inside because of the mass amounts of alcohol that were consumed the night prior. Hair of the dog, right? 🐢

We meet his friends there and luckily they are feeling as bad, if not worse than we are. We are all INSIDE with shades on 😎 because that Chicago sun is just too damn bright. I can’t even function. I order the endless mimosas, because I’m on vacation, and the hangover special which arrives with bits of meatloaf, pasta, eggs, and God only knows what else. The first three mimosas had to be choked down, but it’s smooth sailing from there on out.

New text message from Andy. 😳 oh hell, what does he want?
“You’re in town, aren’t you?”
“Yes sir.”
“Come meet me at the bar and hang out!”
“I’m with friends and rather hungover and I’m drinking again, maybe a rain check?”
“Ha! Where y’all at?”
“Some diner on Halsted. Best hangover cure food EVER.”
***crickets***

Oh well, I’m with Bryan. No need to throw another guy in the mix. We are chatting it up with locals and watching basketball and drinking. Still wearing our shades. INDOORS. Time to break the seal. After relieving myself in the bathroom and walking back to the table, who do I see????? Andy. You guessed it. He’s smiling ear to ear. He comes up to me and says, “I gotta pee. Be right back.”

FUUUUUUUUUCK. How do I explain myself??? “Ummmm, Bryan. Another guy I was talking to online is here. What do I do?” Bryan just laughed and said, “Invite him over. There’s plenty of room.” Wow, very gentlemanly.

So it’s me, Bryan, Andy, and 4 of Bryan’s friends. Awkward. Andy made small talk with everyone and didn’t make it anymore awkward than it already was. Thank God!! πŸ™

The morning after…πŸ™ˆ

Well, it’s the next morning and we fell back asleep after brushing our teeth- so few words were exchanged.Β  This could go one of two ways- awkward or comforting.Β  Is he going to awkwardly make small talk and RUN πŸƒ or will we be comfortable enough with each other to hold a normal conversation and make plans for the day and the rest of my visit here.Β  He’s stirring.Β  The big spoon behind me is moving!!Β  I’ll play coy and pretend to be asleep 😴.Β  When I finally “wake up”- I stretch provocatively with exaggerated grunts and moans (not sure what the point in that was, but it happened).Β  He whispers in my ear, “good morning handsome”…INSTANT BONER!!! Hello round two!!!

Well after that refreshing romp in the sheets, it’s time to get cleaned up and head to brunch with his friends.Β  Luckily brunch is literally 2 buildings down from my hotel (AHHHHH the joys of the city life).Β  I would have much rather had breakfast in bed, mainly because I didn’t want to put on clothes, but also because it is damn near zero degrees out there!Β  Now I have to entertain his friends and be hilarious as usual, it’s exhausting being me.

Brunch is over, my belly is full, everyone has said goodbyes…all I want to do is nap.Β  Hotel door open, clothes on the floor, two naked men in bed- nap time!!Β  Just kidding, ROUND THREE!!!! Ok, now it’s nap time.

Before I doze off and take a much needed nap after a much needed “workout”, I am pondering over the last 18 hours.Β  18 hours ago I was nervous about meeting a man for a first date for the first time EVER and now I am naked in bed with said man.Β  Wow, wow, wow…amazing how much my emotions, my outlook on life, and my entire world have just changed in a matter of hours!! This feeling of euphoria has settled in and I hope this feeling never leaves. I AM GAY.Β  At this very moment in all of my 25 years of life- I have finally been able to admit it to myself.Β  I feel free and happy and scared to death!!!! I can finally be truthful to myself.Β  I’ll worry about the rest when I get home, right now I am taking advantage of as much of this new and improved life that I can!

Moment of truth πŸ‘¬

So you’ve been waiting for the juicy details?? Well, here they are- Brian and I stumbled into my hotel room, brushed our teeth, washed our faces, and crawled into bed. G’night 😴

Ok, ok. I have to be honest. I blacked out. I remember very little of my first passionate night with a man πŸ™ˆ I woke up to empty condom wrappers everywhere (at least “drunk Jimmy” was safe) and a naked, snoring man next to me. I didn’t feel slutty or nervous or regretful. I felt happy and satisfied…VERY satisfied. I went to pee and then looked in the mirror. DAAAAAAAAAAMN. Sex hair was not SEXy at all on me. I was a damn mess. I tried combing it, slapped a bit of water on it, but nothing helped. Fuck it. His snoring ass won’t care. But I did put some undies on.

I fell back asleep and was woken up an hour later by Brian wrapping me up into his arms and nuzzling his face into my neck. Aww 😊 he’s a cuddler!!! BIG BIG BIG bonus points for this fella.

Wow. Morning breath. 😷 Morning oral hygiene is a must, but how do I tell Brian that without sounding like a big ole bundle of bitch?!? Hmmmm. Not sure that’s even possible. Fuck it, just say it and let err bump. “Hey Bri, let’s go brush our teeth.” Naked and hard- he gets up, walks straight into the bathroom, takes a piss, and starts brushing his teeth. That was easy enough. After our death breath had been tackled and conquered, let the cuddle session begin.

Soooooooo, should I even ask what happened last night or should I just leave it a mystery?! πŸ˜•

Bedtime πŸ˜•

After all the drinking had ensued and the night was coming to an end and I was barely able to see straight, the big question was looming. ‘Where are you going to stay tonight, Brian?’ πŸ˜•

Oh hell. Am I going to be a gentleman and go to my hotel alone or shall I invite a certain someone back?! Of course we will only be having a late night snack, a possible pillow fight, and sleep fully clothed with a barricade in between us…right?!?! πŸ™ˆ

If it’s up to me I’ll be exploring my sexuality to the opposite spectrum and back a few times tonight. So here goes…wait…we are in the cab and he has already given the address of my hotel to the cabbie. Ok. I’m game πŸ˜‹

Before I get into the juicy details of my first night…did you ever stop to think about the “what ifs” of gay dates? Such as: what if we are wearing the same clothes? Now how fucking awkward would it have been if I was wearing a black sweater and jeans like Brian was?!? 😳 SOOOOOOO FUCKING AWKWARD! Luckily I have more exciting taste than that and went for a button up. But that could have been catastrophic!! Or I could have just went back into my hotel room and changed, but whatever.

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Or what about dinner? Who pays? Go Dutch? I just batted my eyes and he whipped out the wallet 😏 Jk…or am I?? Who’s going to be dominant in bed?!? Draw straws?!? The thought should always be in your head as to what to do if a “what if” happens. Be prepared my gay brethren.

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Meeting the friends?!? Already?!

So we have dinner at a nice restaurant which included several STRONG alcoholic beverages consumed by both parties and lots of great conversation. This is easy. It’s just like two guys having dinner. No pressure. No nerves. Just getting to know each other and having fun. Earlier in the week he had told me that he had a going away party that he had to be at the same evening of our date- which I figured was just an out if he needed it but then he shocked the hell out of me when he asked me to go with him to this party and meet his friends.

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Ummmmmm, what?!?? Already?! I just met you!!! What the hell! Might as well. I’m awesome. People love me. Why not go and impress the shit out of his friends?! 😊

CAB’S HERE!!! Here we go. We are a 5 mile ride from the party. It’s 9:00 pm. He grabs my hand and just held it without even making eye contact and had the cutest smile on his face. Made my night! Moment of truth. Here we are. He’s holding the door open. Even though I have a slight strong buzz going, I’m still a nervous wreck!!!

“Jimmy, meet my best friend Steph.” 😳 oh hell, she’s the one I MUST get approval from. She was excited to finally meet me- which means he has talked to her about me. Good sign. After meeting 10 friends with 4 of them being intimate friends, bring on the mass amounts of alcohol!!! It was ridiculously hot inside so Brian and I decided to step outside and get some cool air. As we walk outside some random DRUNK girl is halfway in and halfway out of a cab digging in her purse. The cabbie is yelling at her that it’s $8.00 and she was arguing back that his meter wasn’t on. I immediately went into beast mode and chewed the cabbie’s ass for taking advantage of a drunk girl and while I’m trying to help the girl out all while yelling at the cabbie that she isn’t paying a dime, Brian opens his wallet and gives the guy a $10 bill and tells him to go away.

I sent the chick on her merry, drunken way and led Brian to the exterior wall of the bar and asked for permission to kiss him. Of course he said “yes”, but who wouldn’t?!? These lips are delightfully plump and kissable.

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This is the moment that I knew that I love guys. That bearded, scruffy, manly kiss sealed the deal. Ahhhhhh…my past life is over! Let the new Jimmy come to light!

This is it.

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Well the messaging hysteria must come to an end, immediately. I’m getting so damn overstimulated it’s not even funny!!! We, and by we I mean me, have chosen two candidates to pursue. Drum roll please….Andy and Brian come accept your award πŸ†

So I plan my trip to the Windy City to meet Brian and Andy, everything is booked and awaiting my departure, until I find out I have to be in Washington D. C. for four days for meetings with legislators. FML. Really?!? 😩 This business trip overlaps my dates in Chicago. Fuck. After tweaking and bitching and complaining, everything is lined up for a smooth trip to the Nation’s Capitol and then onto Chicago.

The big day had finally arrived. I’m going to make sure I like boys today…dun, dun, dun. It’s Friday evening at 6:30, I’m waiting in my hotel room, and I get the text: “I’m almost there, meet you in the lobby.” AHHHHHHHHHHHHHH 😳 How do I greet him? Handshake? Hug? Chest bump? Wtf?! No chest bump, you dipshit! Follow his lead, he’s the one that knows he’s gay so he should know what to do.

It’s fucking cold out here. Where is he? Should I go back into the lobby? Nah, just stand here and look on your phone until he arrives. Ok. πŸ˜‹

Who is standing in my personal space and staring at me on the sidewalks of Chicago? Karate chop to the throat and a roundhouse kick should teach this creeper a lesson. Ready?? Set??? Wait, hi Brian!! πŸ˜• that could’ve been bad.

Oh, he’s leaning in for a hug. Or is this a chest bump forming? What to do?! What to do?! Aww, a sweet little hug followed by a once over glance and a smile. Yay, he gave approval!!!

The walk to dinner was full of nice conversation but in the back of my mind I’m thinking, “just fucking kiss me so I know if this is the team I want to play for or not” 😀

He ordered a drink and I ordered mine and he’s paying?!? Ok, I’m gay. Keep that wallet out, mister!! Gay date number one- full steam ahead!!

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Digit dropping…

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I better get a new cell phone number!! ASAP! Is there a manual or book for dummies entitled “Gay Online Dating for the Newly Gay and Highly Confused Non-city Boy- Do’s and Don’ts”? If not, someone write the damn thing IMMEDIATELY. Oh how this would have been extremely helpful and time saving for me and I’m sure many other males out there.

So after sending and receiving countless messages via the online dating site, I decide to give my number out to damn near EVERY guy that asked. Umm, oops?? πŸ˜•

So now the creepers can search me on Facebook by my phone number and then they have my last name and where I work and live and can snoop my other social media accounts, oh jeez- the insanity!!!!!!!! 😩

Lesson learned, take it slow and find out who these guys are before passing out my business cards, shit!! So far the conversations have remained good in nature and quality, with some “sexy” talk. But then the picture requests come in, and me being naive I send face pics and/or party pics with friends but I receive FULL NUDES accompanied by the request that I reciprocate. Whoa whoa whoa pony, slow it down!!!

My mom taught me to call my junk, my private parts for a reason. They are private. BAHAHAH! Who am I kidding??? I took the naughty pics and sent those bitches out left and right!! It’s like a head shot (pun intended) for the gay dating scene. Haven’t had any complaints, YET…

But seriously, I should not have expected great things to come from a relationship that started off with “wanna see me naked?” and I should have had more common sense than to send my naughty bits through pictures messages. We live and learn and now hope those pics don’t show up during our run for office during a political campaign!

Deciding who makes the cut

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My mind is on overload. So many guys. So little time. Staying up until wee hours of the morning with endless messages catching someone several someones up on 26 years of my life is damn near a full time job. Wonder if I can monetize online dating to a living wage? Hmm…I’ll need to look into the possibilities of that.

I’m not a heart breaker nor am I a game player. A bullshitter? Maybe 😏 but not into games and endless gloating and bragging. Put up or shut up, shit!

So let’s update the list: BYE BYE PANDA BOY!!! Sorry Cody #2 you’re hot as hell but I ain’t got time for a “bi” boy, sheesh! So we are left with the original Cody, Andy, Aaron, Brian, and Anthony aka Tony (WTF ever his damn name is 😀).

Is it too early in the game to choose favorites? Hell no, let’s rank these fellas 😏
-Andy and Brian (can’t decide πŸ˜•)
-Cody
-Aaron
-Anthony

I’m going to describe the qualities and cons of the top two contenders and I will attempt to think with the head above the waist but I’m making no promises. Here goes.

-Andy: smartass, funny, panty dropping smile (I wear boxer briefs, NOT panties, just for the record and for clarification), lazy with his career, not ready to settle down, wants kiddos, likes to date and make out with whoever is close by, sexually aggressive and pleasing.

-Brian: adorable, hilariously silly, clumsy, awkward in a cute way, family man, transitioning between careers, great smile, sensual, unsure, sends mixed signals, comforting, and a people pleaser.

Ugh. Why is the bad boy the one we all want but know we don’t need?!?! It’s a rarity for the bad boy to be “the one”, but hell who knows!!!

Brian was the first guy that I had any intimate and sexual contact with, EVER! Can you believe that shit???? Most gays have experimented years before they decided to come out but not this gay guy. The first time: I played around, liked it (A LOT πŸ˜‹), and came barreling out of those closet doors telling people left and right EXCEPT my badge wearing and gun carrying dad!! Andy was second, but it all happened in the same weekend. Oh fuck, I’m such a slut. I’ve been called worse, though. As long as you play safe and know who you’re playing with and their background, LET THE GAMES BEGIN!!!!!

I’ll take the lead

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Well if these gays aren’t going to message me, I’ll just make the first move. Just call me Rico Sauve impatient. Oh here’s a nice guy. We are both in the medical field with him as an EMT and myself being on the business side of things, which is so much safer than me being hands on with patients medically!! He’s about my age, tall, pale, and kinda handsome- he couldn’t possibly reject me, right?

Here goes nothin’. Wait, what do I type?!? “Hey what’s up?” No. Sounds lame. “Hey there, how are you?” HEY THERE? We don’t say that. Are we teenage girls??? Be normal, be yourself. So this is what I wrote, you be the judge: “Hey man, I like that you’re a family man! I’m not out to my family, yet, either.” *send*

Now we wait for a response.

WE HAVE A REPLY!!!! “Hey, how’s it going? Thanks for the message. How was your weekend?” HOUSTON: WE HAVE CONVERSATION.

Just as I began to engage in deeper conversation with this fella after thinking this was a waste of time, money, and energy because no one is interested in this small town boy, I instantly have 7 conversations going and the majority were initiated by the other party. πŸŽ‰πŸŽŠWoo hoo, GO ME!!πŸŽŠπŸŽ‰ I should have begun a spreadsheet with listings of the important facts of each guy, but I didn’t and that was a BIG mistake. Oops!! Could’ve saved myself some time and dignity.

So at this point I have a Cody, an Andy, another Cody (this is where the spreadsheet would have came in handy 😏), an Aaron, a Brian, a panda lover 🐼 (don’t ask, that one didn’t take long to weed out), and an Anthony that goes by Tony sometimes (just fucking tell me what to call you, it’s not that damn difficult).

Let the fun ensue!!!

Where do I begin?

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Oh jeez, here goes. No turning back, now. Busted down the closet doors and ran like hell!

Small town boy, comparable to Mayberry (you know- the town of Andy Griffith), son of the Chief of Police, just call me Opie. πŸ˜• Jk, please don’t!

So here I am in small town USA, thinking I’m gay and not sure what to do about it. Feel the frustration and/or confusion? Well, you should. Talk about uncomfortable. Everyone knows everybody, or at least they know your parents or next of kin, and this kids, is how the rumor mills began.

I. AM. A. GENIUS. or so I thought…
β€’Join a dating site they say.
β€’Find your soulmate they say.
β€’It’s free they say.
Ha! Well an hour and a half and $69.99 later, I became an official member of XYZ Dating Site. Let the flood of single, sophisticated, and sexy men come rolling in…

*crickets*

*more crickets*

*more fucking crickets*

Maybe I should answer more compatibility questions? Is there a 24 hour pending profile period? Are my pictures suitable? Wait, we have a hit!! So nervous 😰 Oh, it’s the welcoming wagon. 😀 Fuck this noise. I’ll check back in a day or so, and of course by that I meant in an hour because patience will never be a trait I possess.

“Three guys have checked you out”- what does that mean?!?! Like a library book?? They get to keep me for awhile? Oh shit, what about work? Where are they taking me? Deserted island? Can I take my cell phone? Who will care for my pups? *back to reality* Oh, so they perused my profile. They didn’t hit the like button? Why not? Not their type? Too forward? Fuck it. Over this shit. I’ll check it tomorrow…