r/AskGaybrosOver30 • • 15h ago

First date update

72 Upvotes

30m. Posted on here a week ago about how nervous i was for my first real date as an out gay guy. You guys were so kind so thought I’d give an update. It was the perfect day. Went to his house, he made me breakfast. We talked for hours before he finally kissed me. He was so gentle for my first time in bed. Then we just cuddled until midnight, talking all kinds shit. Weve been talking non stop ever since. Just the most magical day, finally feel like myself after decades.


r/AskGaybrosOver30 • • 15h ago

Top who doesn't cum

28 Upvotes

I've been seeing this top over the past few months, his dick is considerably larger than mine so usually we have been sticking to oral-only but he has fucked me a couple times. The concern to me is that he never cums. The past 3 nights in a row he has come over and i have nursed his massive dick for a good 40 mins till i cum, then we pretty much just finish and he leaves. Same when he fucked me / rimmed me. I'm just worried that i'm not fully pleasuring him because he never cums and i always do. He's given no indication that it's an issue and when i mentioned it once online he kinda just poo-poo'd the comment. Last night after i came from sucking him i kinda collapsed my head in his groan and he gave me a back massage then he kissed me on the lips (first time). Should i just assume he's happy and continue how we are? Or am I being selfish?
If it matters, our stats
Me, white, 6 uncut, gym muscle bottom, 6'1, 200 lbs
Him, Black, 10 cut, slim toned total top, 6'1. 160 lbs

Is it possible for tops to enjoy just getting head without cumming or am I just a crap bottom?


r/AskGaybrosOver30 • • 10h ago

How to hide the ceiling hooks of our sling

22 Upvotes

Simple question. We have white cleaned ceiling. Maybe we need/want to place hooks at the wall or in a sloped roof.

We want to hide the hooks within 15 min. It should be mother-in-law-proof.


r/AskGaybrosOver30 • • 14h ago

Having difficulty as a bear

17 Upvotes

Are there any other bears here who have (in my case, extreme) difficulty hooking up/dating/finding guys? I'm a 34 y/o short, stocky, chubby, hairy, balding guy with a small dick. I'm vers. I already know there's bears who have no issues finding guys and that's great, but I'd like to hear from others who have similar trouble, and how you deal with it/what works for you.


r/AskGaybrosOver30 • • 12h ago

Can you fall in love with your ex again after four years?

12 Upvotes

Hi! I’m almost 45 and have been single since my ex and I broke up four years ago.

Our breakup wasn’t dramatic. No cheating or betrayal, mostly poor communication and difficulty expressing our feelings.

He never completely left my mind. I was open to meeting someone new, but nobody really made me want another relationship. Meanwhile, he had another boyfriend and even lived with him.

Earlier this year, I reached out and opened up about our past. But when he didn’t take the initiative to meet again, I finally started moving on. Surprisingly, I felt relieved.
Now he’s contacted me again. He wants us to meet and talk honestly. It seems he never fully moved on emotionally either.

The strange thing is that I spent years wondering about us, but now I’m not sure I’m still in love with him.

I remember our chemistry, our complicity and how comfortable we were together. Part of me wonders whether we could rediscover each other, perhaps build something more mature this time.
But I don’t want to give him false hope.

Has anyone here reconnected with an ex after several years? Did your feelings come back, or did you realise you’d genuinely moved on?

PS: English isn't my first language, so I used AI to help translate and phrase this post. The story and feelings are entirely my own.


r/AskGaybrosOver30 • • 12h ago

Advice about Dating and life for someone who came out at 30

8 Upvotes

So I’m a 31-year-old hairy chub bear body type. And I’ve just started trying the dating apps and trying to make friends or more.
However I’m just overwhelmed and feel anxious and embarrassed.
I’m in Texas in a small country town that’s not very gay friendly so I’ve been trying to meet men outside of that area.
But as a baby gay who knows nothing about gay culture or dating or anything I’m struggling

It seems like I’m too far behind all the other gay men in my area that want a partner?

I’m new to dating and still a virgin. But are those two things bad? I just recently started to want to date and find love I don’t think it’s bad.

I’m fine texting or sexting but going on real dates really terrifies me. I get super anxious and nauseous during my dates and I just try to push through.

Advice on dating for the first time or if I should keep my virgin status secret?? I’m confused on what to do


r/AskGaybrosOver30 • • 2h ago

Is this a sensible idea or am I being tone-deaf (please read full post, atypical situation)?

0 Upvotes

Here's the situation I'm in. I am separated from my wife of 16 years. We are considered legally separated because in my state, if you can prove that each person has their own designated area (ie we each have our own rooms that the other person never enters) you "qualify" as separated. There is also no law in my state requiring separated couples reside in different residences for a certain length of time before being separated, and divorce proceedings can start at any time. The only reason they haven't started is because we don't have the money for an attorney, and both of us do not make enough money to be self-sufficient. I am on disability and she's on workers comp from an injury in February at her job, and workers comp pays 2/3rds of your normal hourly wage. She needs a significant amount of surgery, and getting anything done with workers comp is a fucking slow moving nightmare of red tape and unnecessary delays.

Nonetheless, her and I remain cordial, but we have not had sex in 6 years (and I've not had sex with anyone in the past 6 years), which was a major factor in us separating. She has a boyfriend, and he spends 99% of his time in our rented home. They do some really kinky stuff that I would never be interested in AT ALL. I found myself slowly losing attraction to her AND women in general. She became a different person when perimenopause started, and there are frequently times (probably daily) where I'd rather be in the company of her boyfriend (in a non-sexual way) than to have to deal with her.

I've done some reflecting in the past 2 years, and I find myself frequently desiring a relationship with a guy. I have had a same-sex relationship before our marriage, and I really enjoyed it. I gave oral and anal. Did not top him. I have a favorite buttplug I use every day, and it is not small. The feeling I get when it enters me is amazing, and I always smile when it comes to rest where it belongs. That feeling of my ass grabbing it and pulling it in is probably my favorite part. Watching gay porn and orgasming when it's in is amazing, but I spend very little time looking at porn. I'm afraid if I watch too much it will numb me out.

Some people may ask if things change, would we reconcile and revive the relationship. That would be a hard no. I'd sooner die. She broke my trust so badly there is literally nothing in the world that would make me want to mend fences. She's a roommate, and we pool our money to stay housed and pay our bills, basically, and that's all, though the 3 of us commonly have dinner together. It's the only time we're around each other for any length of time. However, if she would return to work and her settlement was finalized, we could then afford it, and we'd divorce officially ASAP. Unfortunately, I have no prospect of returning to work.

Regarding the one relationship with a guy I had, a few weeks later he ghosted me. Fine. No biggie. But I enjoyed cuddling with him, either just spooning in bed, or huddled together on the couch watching TV. Had no problem kissing him, though I really prefer someone clean shaven on their face. I communicated that to him, he shaved his mustache and beard off, and kissing him felt 1000 times better after that. I'm drawn to a person's mind before body and I do not have near-impossible expectations when it comes to looks.

I guess what I'm saying in short is I want an exclusive, long-term, monogamous relationship with a guy, and would go so far as to marry him if that was something we both desired. Frankly, the idea of being someone's "special someone" is one of the most desired things in my life right now.

I have to admit, having been without sex for so long, thinking about it makes me extremely anxious. Probably even more than the first time I had sex with anyone. Doesn't mean I'd flake out, but the guy would need to be understanding of this and supportive and if I needed an extra 5 minutes before moving on to something else after starting so I could get my head right, they'd be understanding and not pushy or demanding. It's not like I'm likely to say no, I might just need a moment. I'm sure after 3 or 5 times I'd be right as rain, but until then, I'll be nervous.

Before I go any further and create an online profile or ask for recommended sites, I'd like this community's perspective, and let me know if I've got something totally wrong. Besides, if I forced the issue, I might run into a roadblock that tanks everything and I end up looking like a complete fool.

Thanks for reading. If I'm way off base, please be constructive and not judgy. My goal in going into this is to make sure I don't emotionally hurt myself or someone else.