Ask Chad

Dear Best Friend Fucker,

Did you ever see My Best Friend’s Wedding? Didn’t turn out so well. If they’ve been together for years then it’s probably not going to change anytime soon. If you make a move and it backfires, you’ll be out with the trash. If you are besties, I’m assuming you’ve had drunken nights out and if you haven’t made out or fucked before then it probably isn’t in the cards. If you want to test the waters, head over with a bottle of wine in a pair of grey sweatpants. If he looks, then maybe you have a chance. If he drinks all the wine and doesn’t make a move, maybe you’re ugly. Just kidding…but you may forever be in the friend zone.  As far as the horrible boyfriend situation, could be you’re just jealous. If he is that horrible and your boy is still with him, then he must have a big dick. Threesome, anyone? If you can’t beat ‘em, join ‘em!

Dear Harness Harry,

It’s a fucking handle hold, dipshit. Grab onto your man’s harness and ride. If you’re in Palm Springs, you’ll notice a lot of the older guys mistake a harness for a bra. Don’t make that mistake. And yes, every gay needs a harness in their closet.

Dear New Rimmer,

Oh, Jesus – you can’t even spell out ASS? Gurl, grab that ass by the cheeks and go to town. Honestly, rimming is an art and a great rimming technique will get your bottom wet and eager and easy to slip in. That being said, the first time rimming can be eye-opening…brown eye-opening. I keep saying, porn is the best 1st education and most porn has become very hole-centric. My personal technique is to start off massaging, kissing, and gently biting their ass cheeks. Make sure you are in a comfortable position and have some leverage, a good rimmer takes their time. Next, test out the waters with your tongue playfully teasing the hole. Once you get it wet and get your bearings, GO TO TOWN. Use that tongue like a dick and go in and out. Also, try the triangle technique – move your tongue up, down the right, to the left, and back to the top. Also, take some moments and go back to the cheeks, and pull their dick and balls from behind and give those some attention too. If your bottom is moaning, you’re doing a good job. If he’s reading a magazine, you are terrible. ALSO, a good rim session isn’t just up to you. The bottom has to be CLEAN. No one wants a mud pie. It may take a few times for you to get comfortable with it but, just like a blow job, even a bad rim job is still a rim job. If you want to practice, I’m available. Can you host?

Dear Nosey,

Mind your business. I’ll see you on Grindr!

Dear Chubby Chaser,

It’s my opinion that your partner should make maintaining their looks part of the relationship and try to resemble what they looked like when you first start dating. Of course, life happens and things can change. BUT, we aren’t straight couples. Straight couples get married then get ugly real fast. We have a duty to each other and our community to look better than straights. If you are a shallow bitch, just dump him. If you have feelings for him, set the example and invite him to the gym, or hikes, or suggest meal prepping together. Also, just be honest with him. If he’s not a whiny baby, he’ll respond well to you being loving but direct.

Dear No Head,

Dump him. Or find someone else to suck your dick on the regular.

Dear Work Jerk,

Is there someone hot new at work, do you know why the sudden need for speed at the office? I know when I’m hungover, I tend to be super horny the next day and need to jerk a few times a day. Jerking off is also a stress reliever, maybe you have other issues going on. BUT, if your coworkers are starting to notice, then maybe it’s interfering with your job which indicates a bigger issue. Try jerking off twice in a row before heading off to work or consider quitting so you can jerk all day in the privacy of your own home.

Dear HomoChef,

Does it seem like I’m someone who can cook? Just save the hassle and order Postmates…if you want to impress him just put it on a plate like Mrs. Doubtfire did. If he’s bottoming, just order salads. Bloop! Unless you have a maid, the least sexy thing is a pile of dirty dishes in the sink or making your date wash them cause you drank too much wine at dinner…is that just me?

Dear Long John,

Despite all the romantic Hollywood movies, long-distance relationships just don’t work. Number one, there’s no fucking on a Tuesday. Number two, you just don’t get that boyfriend experience where you come home and talk about every detail about your day, then fuck. You also don’t get regular cuddling…did I say fucking too? Having been in multiple long-distance relationships (at the same time), it’s just impossible to keep up that boyfriend energy. Relationships are about the tiny details (and fucking, did I say fucking?) that come from being a drive from or in bed with your boo. You’ll notice little by little the FaceTime sessions decrease, little by little the texts stop coming, little by little the hot neighbor next door wants to Netflix and chill. ALSO, traveling all the time is exhausting and jet lag will affect your skincare routine. Just cut your losses now and save the heartache down the line or, if you are really in love, pack your bags and move with him.

Dear Damien,

P.S. I loved your work in The Omen! Most of my friends have made a lot of money on Fans accounts, especially during COVID. I would start one myself, but my sugar daddy won’t let me. You can make a lot of money from doing it, BUT people don’t realize it’s a lot of work. Not only is there a lot of competition out there, but you also have to book your co-stars, clean your goddamn room, get good cameras and lighting, AND be a good editor. No one wants to look at some amateur iPhone crap. There’s a lot of technical stuff involved to produce a good product and you have to push on Twitter just to get your stuff seen. You also have to be comfortable with putting your junk out in public. Once you start, you can’t go back…everyone will know you are doing porn. We have assholes in our own community who will put you down for doing Fans even though they are jerking off to it. Once you go back to work, rest assured if there is a fellow gay on your staff they will rat you out. That’s how I lost my job at the Gap, I was filming in the stockroom. Who knew that khaki wasn’t stain-resistant?