Spicy Conversations over Burgers

My St. Patty's day recapitulation.

Keg stands in Chicago, IL this past weekend

Chicago is a necessary fast for my soul. Not like an intermittent fast where one indulges for an allotted time period before putting themself on timeout. Well, I suppose it feels less demanding than a fast and more tolerable like a diet—from Los Angeles. The Windy City is a salad that is good for me. One that is packed with kale and made by someone who was stingy with the ranch. It tastes unsatisfying with every bite.

And while some bites are worse than others, I wake up the next few days having more energy, feeling less lethargic, and looking skinnier. My stomach is flatter at the price of my tastebuds.

I touch down at Ohare on a gloomy Wednesday. I forget how big airports are and am stunned to find I’ve completed my fitness circles for the day and it’s only 6 AM. With all that walking around and Red-eye delirium, Fiona says, “Oh wow the lights are so pretty!”

They’ve never been here before and I tell them to brace themselves before we step outside and are gobsmacked by vengeful thrusts of wind. In all directions, attacking us up and down, left and right. There is no escaping it, only surviving it.

And then I think about LA and about how much better the weather is there, generally. Then I think about people at large. People who choose to live in environments like this. I wonder what the insides of their heads look like. I think about whispering in their ears, and asking them if they’re okay.

I nosily wonder about other people's lives, frequently. It makes up 30% of my internal dialogue, although I am thinking of cutting it down. Because I have done this for so long and do it so often, I’ve created a couple of shortcuts. I used to go around in circles of the endless possibilities to my inquiries and because this a slippery slope into an anxiety attack I figured wisely to develop a safety net to serve as bounds to where my mind can go looking for answers. I’ve come up with this to help prevent spiral.

There are certain factors to—without fail—take into account when tackling topics of humanity. Money is one of these factors and I’ll save you the trouble, it’s usually the answer to the question, whatever is being asked about regarding people at large and their living situations.

And given that it’s not too expensive to live in Chicago when comparing it to other large metropolitan cities, maybe that’s why people live there.

“They say it’s the last livable city in America,” I say to Fiona as we wait for our uber to arrive, trying not to shiver too noticeably like foreigners.

But the thing is, if you’ve managed to survive in Chicago, you can just as easily live in any of the major southern cities, at the very least. And you wouldn’t have to deal with such brutal winters and you’d get more than two or three months of summer weather. Of course, you’d be in the South, which has its own drawbacks, sure, but just order a pair of cowboy boots online and get the Vitamin D you deserve in person. Fuck the Amazon pills, go and get the real deal. The real sunlight. Why do y’all live like this?

The second answer to these types of situations is usually work opportunities, which do what? Help people make money. Unless you’re in school like I was when I decided to move to Chicago, which, you guessed it, cost a lot of money. Told you, saving you the trouble and time.

And with all this being said, I ask that you pardon me as I don’t mean to gerbil and make it seem like I want a refund. I wouldn’t trade my experience in the Windy City for any amount of money. For one, I think relationships are more valuable than cash and for two, I made so much of my most time-consuming art in Chicago. I wrote my first novel there. I made so many of my favorite songs in Chicago. I don’t wish I did anything differently or lived anywhere else, that’s not what this is about.

I’m visiting for the first time as a non-resident since I came on a school tour my Junior year. And I guess it’s been, interesting. I’ve used that word to describe the different occurrences I’ve had here in the 50-minute uber ride at least 5 or 10 times to Fiona and our Uber driver. I’m sure they’re sick of me reminiscing on old times but I can’t help myself before I eventually do realize that while most of the memories are exciting, they bring with them this feeling of hollowness, now that I don’t speak to half the people I made them with.

“Any food recommendations?” Fiona asks after I’ve trailed off and look somberly out the window and industrial land.

I feel the cold all around me and I ask myself how I withstood it for four years. Why I endured what I was not forced to do. What kept me here? I am yet to figure that out but as for now, I know it helped that I made such amazing connections with the people here. It also hurt and altered my brain chemistry when I lost those situationships. And so now, I’m sad.

“Try Giordano’s of Piccolos,” our Uber driver tells Fiona.

We slowly pass by a Portillos stuck in morning traffic.

I am hungry for meat and make the decision then to have a burger for lunch.

---

Chicago was a great city to discover my sexuality. Maybe not discover, because I knew I was attracted to men before that, but it was definitely a good place to explore all the different ways I am and show love. It helped that I was in a place like Boystown that is unapologetic about its LGBTQ pride. Before this, I had close to no pride in being attracted to men. I felt it was bastardizing. What was there to be proud of? Only shame and fear, and it’s like that for many still so beyond enjoying Chicago, I’m grateful for it. I’m indebted. And that’s why it’s so hard for me to leave all the time.

I even appreciate the dirtiness. The filth. All the grimy aspects of the Boystown scene. The dirty cum stained floors, the ass juice dripping out of stretched holes. The oiled-up dicks being sucked bare on the dance floor. You wouldn’t know it by this description alone but there’s a wholesomeness to a hot and musty gay club.

Like the guy who was a stranger seven minutes ago, giving me a hug and looking me in my eyes as he cups my face, telling me he never wants to let me go. The mean mugging security guard that has been yelling for everyone to back up is the same guy that calls me handsome before handing me back my ID. Just the boost I needed heading inside. Or when I’m stalling in a corner swirling my $14 tequila soda. Taking small sips so I can make it last. Savoring the taste, waiting for the alcohol to do its thing. Where you get warmer and more confident. And then a group of guys shows pity on me having been there before—afraid to ditch the shell—and ask me if I want to dance because I look like a lost puppy.

---

And then I realize as my Uber driver is taking us to Gabby’s apartment in Lakeview that I need to find time to make it out to Boystown sometime in the weekend. I wait to arrive at Gabby's before I close my eyes. Fiona and I fall asleep pretty quickly while Gabby goes off to run some errands. Around late lunch, I wake up Fiona and tell her we’re meeting with my friend Bella for lunch at Corridor, a brewery off of Southport.

I order the Double Steakburger and the girls get the Bean Burger. After asking for our waiter’s recommendation, I also order a large beer. We order Buffalo Cauliflower for the table, which is otherworldly. I look at the plate during bites of my burger to make sure there are at least a couple of pieces left over. Like if taking my eyes off them will mean they will disappear.

We finish eating and we sit there talking about how good the food is before hitting that wall that limits functionality. The one where you’re too full to even get up and use the restroom. When the hallucinations and the giggling begin.

“I’ve only had one orgasm before,” Bella says.

“Yeah, I haven’t had many, tbh,” Fiona responds.

“The worst part is having sex and feeling like just a hole and it’s over in like 10 minutes,” says Bella.

“Yeah, that’s why I appreciated my last hook up because he actually cared to make me cum. Most guys just fuck you till they come and roll over like they’ve done both of you a favor,” Fiona says.

It’s almost like they’ve forgotten I’m in the booth, the way the conversation has shifted to something only they can relate to.

“Well, have they not done you a favor?” I ask, earnestly.

“Like does sex not feel good for you?” I ask, innocently.

The girls look at one another and roll their eyes.

“You sound like such a straight man, right now, Tobi, seriously?” Bella says dismissively.

Fiona tried to find which side to take.

“What do you mean?” I ask with attitude, feeling something flare up inside me.

“When guys have sex with other guys, both people are enjoying themselves. It feels good to be fucked and it feels good to do the fucking. It’s a win for both sides and both parties enjoy the experience. That’s dick to anal and anal to dick,” I say.

The two girls' faces soften having seen where I’m going with this.

“What you two are telling me is that when guys fuck a vagina, it doesn’t automatically feel good, that there are other things that need to happen for it to feel good?”

“Well, yeah, I see your point. It is different. For girls, there are other things that have to take place emotionally and sensually, like foreplay and stuff. Most guys are just too lazy to do it,” Bella says.

“Yeah, also men have a G-spot in their anus, so that’s why it probably feels good for both parties,” Fiona adds.

This is something I know already but I let them explain it for themselves.

“Yeah, like they’re just too lazy to care about pleasing us and they go straight for pleasing themselves,” Fiona adds.

“Well do you think they know this? Like they know that penetration doesn’t just automatically feel good for you in the way that it does for them?”

“Of course they know, Tobi. Stop defending them,” Bella demands.

“No— I didn’t mean to defend them. I just was wondering, because this is my first time like really fully understanding and I imagine they don’t have women friends to discuss sex with,” I say softly.

“Oh, well yeah, they know,” Bella says flatly.

I feel bad for asking but when will I ever get the chance again?

“Do you guys think it’s harder for women to have orgasms because of the hardware you’re dealing with?”

Fiona and Bella give me a disapproving look.

“Like, think of a cock—“

“Ew, I hate that word,” says Bella.

“Yeah, I don’t like it either. Just say dick or penis or something,” Fiona adds.

“Oh, okay. Well, I guess it does sound pretty aggressive,” I stumble.

“I just mean like with a dick, it’s pretty simple, you go up and down and men are such dogs that you don’t even have to touch it before they reach their climax,” I say.

“They'll fuck anything that moves,” I add.

“You’ve stated for women that’s not the case, so do you think—“

“That some of it is biological? Sure,” Fiona chimes in.

“Yeah and you know, conditioning. Men are conditioned to embrace their sexuality and go out there and fuck whomever they want. Women are conditioned to stifle any of their more promiscuous thoughts until much later in life and even then, there’s still a stigma around a sexually liberated woman,” I say, feeling like an ally.

The girls nod in a decent amount of approval. Like black people to white people harping about how shitty other white people are.

“So would you say it’s easier for men to reach their climax?” I ask, eagerly.

“I mean, it depends,” Fiona says.

“Well, what’s the quickest orgasm you’ve had? Because for most men it’s been in seconds,” I say.

“Probably a minute,” Bella says, chuckling with her eyes recalling a time.

“Yeah I would say like a couple of minutes, maybe less honestly,” says Fiona, also smiling.

“The thing is my quickest times have been by me masturbating,” Bella adds.

“Like I obviously know my body so I know what turns me on. And you tell a guy the same thing and they do it for a little and then give up and stop after a while and just go back to fucking you,”

“Exactly! Like if men were teachable and ready to learn from us, then more women would have orgasms,”

“Yeah, but they’re too prideful. This conversation is depressing,” Bella says finally.

And the entire time, I sit there astounded by how much I’ve learned. I think about the new guy I’m seeing and how he knows how to make me orgasm. And how I shouldn’t take that for granted. And I get this political urge to broadcast this conversation into larger discourse. Because everybody deserves to cum. It’s your birthright.

And I think about people, again, but specifically women. And how I’m grateful to be friends with women. I’m astounded by how generous they are. And how the two women sitting next to me were strangers before today, but now talk like long-lost sisters. And it amazes me how open they were willing to be about their inner desires.

And I feel ashamed of men, because even I know to massage the clit and I haven’t touched a vagina in years. And I know for sure that this conversation or the rest of what was an eclectic and thrilling weekend couldn’t have happened in LA.

That's when it hits me. That the reason why people tolerate living in Chicago is because of the people. And the reason I love Chicago is because of the people. And the only way a city prospers is by agreeing to camaraderie. By doing good for one another. By listening to one another.

So when we step outside the brewery and are greeted by mini snowflakes and slippery concrete, I don't wince. I open my mouth and stick out my tongue.