u/shortproudlatino

I definitely think Chicago itself is a very accepting and diverse place, especially the city proper. There’s real progressive energy, good events, and an overall vibe that feels open.

At the same time, does it ever feel to anyone else like the city still carries a pretty strong Midwestern cultural undercurrent? For all the diversity on paper, the social and dating scene (and the long-term close friendships that form out of it) seems to cater pretty heavily to a specific type, tall, muscular, white/latino. It can feel more white-serving and heteronormative than a lot of other big cities.

And it’s not even like that standard is easy for most white guys either. A lot of them don’t live up to it and still get sidelined.

Although it could be that just the most established gay regions and resources are concentrated in white/centric places .

It typically takes about 10-15 minutes for my boyfriend or any other guy to actually start fucking after trying to get it in.

I don’t know if it’s just me being nervous but even fingers hurt a lot and when it’s time to actually fuck I’m honestly still in a lot of pain, but my boyfriend deep moans and reactions motivate me to keep pushing for him.

I do wonder though, do some tops get annoyed if it takes too long for a bottom to loosen up?

I’ve always felt a little insecure about my butt, it’s on the smaller side and can barely fit into size small jeans or pants. My boyfriend though is obsessed with it and calls it a perfect bubble butt. He loves the round shape and how perky it is.

It makes me wonder… is shape actually more important than size? I’ve been thinking about gaining a few pounds to chase one of those bigger round butts I see everywhere, but if shape is what really matters maybe I shouldn’t?

What do you guys think, shape or size? And would gaining some weight even help get the look I’m after?

My best friend is moving to Chicago in a few months. He’s from a small town in Tennessee (suburb of Memphis) and wants a neighborhood with Black presence and lgbtq/hipster activities, but also an easy commute to me in (I’m in Logan Square) so we can hang out easily. His new job is near the medical center in Humboldt Park, so I suggested that area. P

Is the West Side still a good fit for him, or would he feel more comfortable on the South Side or in Uptown? We only have 3-4 days to apartment hunt and don’t want to waste time commuting across the every day.

What do you guys think?

As a bottom every time I have sex with my boyfriend he’s a little above average at around 7 inches. His head hurts but once he’s through it’s easy

Meanwhile I remember before when I was with guys who were 3”-5” it would actually hurt alot

I see countless posts about the bad experiences in Chicago, and I get it, I even do that myself those complaints and rants are valid.

HOWEVER

This is one of the largest and most diverse gay cities in the United States. The scene here is roughly 1/4 Black, 1/3 Latino, 1/3 White, with a sizable Asian population and everything in between. You’ll find every type of gay imaginable: gym gays, intellectual gays, DL guys, college kids, political activists, religious folks, feminine, masculine, twinks, jocks, bears, otters, older, younger, you name it.

There are so many spaces for everyone. Sure, some of the big headliner events attract a very specific type. But for every 2,000-person party where you don’t vibe with the crowd, there are a dozen smaller events with 10–20 people you actually connect with. Find those events and those people.

This city is way too big to chase validation from one guy or feel ashamed because you don’t share the same skin color, body type, or interests as the person in the other room.

I’m an afro-Latino man, and I have a boyfriend. However my main goal is to find friends. I knew going to the south side or west side was best for this, however every gay guy I meet on apps or in bars, etc. down south seem to try to pretend they aren’t gay in real life and even shame gays they see publicly.

Not to mention the amount of men actually dating or married to a woman but frequently being around men untested. It sets a bad idea for us. I know certain communities can be unsafe but it’s 2026.

I have a close friend (also a bottom like me) and we have really good conversations. But he constantly makes self-deprecating comments about being 6’2 with a rugby build, saying how easy it must be for me as a 5’3 120lb bottom. He has no idea how attractive his body is.

Any tips on how to help him see it / shut this down nicely?

I’m a bottom and my boyfriend and I just moved in together. We’ve been having sex 3-4 times a week now, he’s very dominate.

I’m kinda insecure though be last time we fucked he didn’t cum for a while and I noticed I didn’t feel any pain at all. I looked afterwards and my hole looked pretty open. When I first met him, you could barely tell a hole was there.

Any tips to get it tight again?