Ask Chad Archive

Who is Chad? Chad, the Queen of Queeries, is Cybersocket's in-house, know it all. Depending on his mood and how much he's had to drink, he could be naughty and nice. Chad is... that guy. Part douche, part dick, all sass. Plug In. Get Off. Do you have a question for Chad?
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by Novice Bottom
March 19, 2023

Hey Chad,

I am typically a top and have limited experiences bottoming, and the reason is because it hurts too much. Every time I go through the same thing, clean out, hype myself up, poppers, lube, and try taking it slow. But the outcome is always the same, it hurts and I can’t enjoy myself and then stop him after a few minutes because it is too unbearable. How do I bottom without it feeling like I’m passing a watermelon?

Thanks,

- Novice Bottom

Wow, thank you Novice Bottom for the graphic imagery. So to avoid passing a watermelon, try relaxing! Yup, that’s right, relaxing. It sounds like you’re too stressed girl, and you need to breathe and unclench that little bussy hole or else you’re gonna get a fissure! Make sure to take deep breaths as he’s pushing in, and make him go slow. Once he’s fully in, make him stay very still for at least 1 minute to allow your hole to adjust while he’s inside. Once you adjust, keep breathing deeply and allow him to go SLOWLY in and out in small strokes. Slow and steady wins the race. Make sure there’s plenty of lube and even take a hit of some poppers for some extra preparation. Even try some small to medium-sized toys before he comes over to loosen you up. Good luck in entering your hole era!

by Night Owl
March 19, 2023

Chad,

There’s nothing that ticks me off more than a flake, and lately, I keep getting ghosted on the apps. I get tons of messages when I first log on but by the time I am ready, or the later it gets, the more likely they are to flake on me and then I end up finishing myself and going to sleep. How do I get a hookup to come through?

SOS,

- Night Owl

Girl, you gotta get ‘em while they’re hot! Most guys get on the apps because they’re horny right now and ready to go. Don’t wait to douche and shower, get ready first and then once you click you better be ready to catch a dick. Play the field for the first 15 minutes and get the hottest one you can because the later it gets, the slimmer the choices you’re left with. Also, don’t be one of those endless chatters. If you’re there to get cock, don’t get hung up on the conversation or you could lose the load. Hope this helps!

by NotUrSugarDaddy
March 19, 2023

Dear Chad,

I am a little annoyed to have to even ask this but what is the policy on paying for dates? I recently went out with a guy for the second time now and I had to pay for everything BlOTH TIMES. He didn’t even reach for his wallet when the waiter brought the bill, or when we went to the movies! I feel like that’s so rude, like it should be his turn the second time right? Or do I have to say something about splitting the bill from the beginning?

Thanks,

- NotUrSugarDaddy

Major oof, nobody likes a broke ass bitch. You need to be more upfront next time with your feelings! I am a quasi celebrity so I don’t pay for anything, but girl you better get his form of payment up front or else it is a no deal. I would literally make a scene so big that Bravo would cast me on RHOBH. Fool me once, shame on me, fool me twice and I’m flipping a table. So tell that man the next meal is on him or it’s your fault for dating a fraud. Period.

by Frustrated Sugar BF
February 14, 2023

Dear Chad,

I'm in a bit of a situation. My boyfriend is super wealthy and because of that, he pays everything-- our rent, vacations, my car, dinners out, etc. But he's also an asshole about it and likes to lord it over me. He also likes to say he can fuck around because he pays for everything so he's entitled to have his fun, as where I am somewhere between a houseboy and a boyfriend. How do I find balance in my relationship?

Thanks,

- Frustrated Sugar BF

Dear Sugar BF,

A rich boyfriend is always the dream until they act like they have all the power in the relationship–which they always do, ’cause money talks. So ask yourself, how much do you love your lifestyle? Would you be ok living paycheck to paycheck with a boyfriend who is your equal or do you love your free trips to PV and Greece too much for that life? As for me, I like the gifts, but you do you.

by Muddy Top
February 14, 2023

Hi Chad,

Here's the deal: I'm vers and my fuck buddy was always a top. We've been fucking a month and a half or so (and we're neighbors so at least a few times a week), and I suggest maybe he start bottoming so I can get my top off too. Turns out, he is game to try bottoming with enough poppers, so we try it. And he is messy. But whatever, the first time out, I move on. We try it about 3 other times, and every time a mess. He's already self-conscious about bottoming so how do I bring up to him about cleaning out without him shutting down completely?

Help!

- Muddy Top

Oh, Muddy Top. That is not tea! Not every man is made to be a power vers. I would say this man is not your man, he’s your FWB. So use him as your dildo and find another guy to use as your ass. Let him just top you if he’s good at it, and get your rocks off elsewhere. If you want to keep it all with him, maybe buy him a douche as a gift. I always like getting gifts from the men I sleep with.

by Horny Neighbor
February 14, 2023

Hey Chad - Random questions. My neighbor is so hot and I always see him on the apps. When we pass in the halls or elevator he smiles or says hi, but when I tap or message him on apps, he NEVER responds. How many times can I reach out on Grindr before I look pathetic? Also, why be nice IRL and ignore me on the apps?

Thanks,
Horny Neighbor

- Horny Neighbor

Horny Neighbor,

I hate to break the bad news but it sounds like you already look kinda pathetic to this guy. Anything over two reach outs on a gay sex app is unacceptable. Maybe, perhaps, he missed the first hey, sup, or whatever, but after two, you’re done. He sees you in the hallway and elevator, if he was trying to fuck you, he would be flirting with you there. Block him on the apps if you can’t help yourself but don’t reach out again.

by Zesty Cester
December 4, 2022

Hi Chad-

I recently started playing around my cousin. It started as drunk flirting and then, when he got hard, I realized he was at least bi. It's been SO HOT. I'm like the second guy he's ever done stuff with and he can't get enough. We have to sneak around a bit but who cares? So here's why I'm writing, my cousin got a girlfriend and I'm pissed as hell. I don't want to be sharing his dick with some girl from the neighborhood. But how can I be jealous and clingy with my own cousin? What do I tell him without it sounding crazy? He's not out and we're cousins so there's no path that leads to me and him being together, but I want to keep fucking. Help!

Thanks

- Zesty Cester

Get it, Zesty Cester. Everyone loves an incest story. I’m rooting for you, even though this is impossible, girl. Give up. Back all the way up and don’t ruin this long term. He’s your cousin. That’s solid, secret dick for life if you play it right. Let him go and say whenever he wants better head from a guy, hit you up. Cousin dick once in a while is better than no dick, which is what will happen if you act like a crazy twink bf.

by Lonely Cruiser
December 4, 2022

Dear Chad,

I love getting off in gym saunas and steam rooms. I love the hunt of cruising in public, especially over hooking up on the apps. The only prob is that you can never have repeat hook ups. I like getting off this way but I crave connection sometimes. I'm almost 33. How do I ask for digits at the gym without looking sad and desperate to hang again?

Thanks
Dear Chad,

I love getting off in gym saunas and steam rooms. I love the hunt of cruising in public, especially over hooking up on the apps. The only prob is that you can never have repeat hook ups. I like getting off this way but I crave connection sometimes. I'm almost 33. How do I ask for digits at the gym without looking sad and desperate to hang again?

Thanks

- Lonely Cruiser

Ok Lonely Cruiser, you’re over thinking this. People ask for my number all the time! Like if a grocery store clerk can ask for my number while I’m buying snacks and lube, you can bet you can ask for a number after getting blown at the spa. It’s so easy. Just say, “That was awesome. Take my number if you want to do it again sometime, maybe on a bed or a couch.”

by Drying Out
December 4, 2022

Hey Chad

My drinking is killing me. I hate it but it's such a social part of culture, especially gay culture. I don't want to go into a program or anything, just stop blacking out with my friends on weekends. I don't want to be kicked out of the group for being the boring sober one. Any suggestions on how to still have fun but not be a wasted mess all over Chicago.

Best,

- Drying Out

Oh Drying Out,

That sounds tough. I haven’t been sober since 15 so this is a bit of a wrong tree scenario. I always find if you’re on drugs, you’ll drink less alcohol, but it sounds like maybe that’s not what you want either. So, tell your friends your “off shots” and just order your drinks not around your friends. You can get a club soda with a splash of cran and no one would be the wiser. You don’t need to drink but that shouldn’t stop you from going out and having fun. No one is policing what you’re drinking. It’s all in your head, so just be the person you want to be.

by Public Bator
November 20, 2022

Hi Chad. I love jerking off in public. It's the only way I can really get off and achieve the best orgasm. I started dating someone recently and when we were just fuck buddies, we'd hook up in public and it would be cool. Now he's worried about it because he doesn't want to get arrested and have a record because of this. The problem is I like him, but not enough to give up my public play. What do I do?

- Public Bator

Howdy Public Bator,

You are in a bit of pickle, aren’t you? Public play is hot. You clearly like the kinky idea of getting caught and that’s clearly stressing him out. You have to figure out which is more important, this guy or you getting your nut in public. If it is this guy, you have to adapt and hook up in safe public spots and at home. If it’s public bating, have fun man. Just explain you need this and you understand he doesn’t but now it won’t work out.