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Misha from Richmond, VA asks:

This is a real question. And I know you sometimes answer sex questions. So I want to know…how do you give the perfect blowjob? The type of blowjob that’ll make him call out to God; the type of blowjob that’ll make him curl up on his side and take a nap afterwards; the type of blowjob that’ll linger in his mind the next day; the type of blowjob that’ll make his highlight reel. You see I’m really competitive. And my boyfriend of two years admitted during pillow talk a few months ago that an ex from a long time ago was the best head he’s ever had. And he couldn’t even say exactly why. In fact, he tried to walk back the whole thing. But it’s been at the back of my mind ever since. And now I’m determined to at least be as good, if not better. So, can you help me?

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No.

No.

No.

No.

No.

No.

No.

No.

No.

No.

I’m not here to help with bird ass, Becky ass ambitions.

What is wrong with you Misha?

Who wants to be good at giving head? Why would you want to be good at giving head?

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Do you realize that the better you are at it, the more blowjobs you’ll have to give?

Do you think you can beat ghost head of Christmas past? He didn’t even stay with ghost head. All that A1 work she put in, and she’s just someone he stupidly mentions during pillow talk.

Also, what kind of pillow talk are y’all having?

No one should have to be on guard post-coital. You’re fucking with the afterglow.

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Ghost head didn’t do anything special. Ghost head probably just made him feel special. Ghost head gave him eager sloppy toppy the night Obama got elected and anything was possible.  How are you ever going to compete with that? You’ve been giving him head while Trump’s been running for president. That’s never not going to be depressing.

You’ve already lost Misha.

But fine.

I’ll tell you how to give Oscar worthy head. (Although I still can’t fathom wanting to. My real advice is to always look at the penis like you’ve never seen one before and you’re slightly unnerved by it. Make him feel insecure about his shit. Make him hesitate to put it in your face. But that’s just how I’m living my life.)

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Anyway, the first thing you’ll need is enthusiasm. And lots of it.

Actually you need equal parts enthusiasm and spit.

(How gross is that to write out. I’m already regretting this.)

Dry toppy is what you give when you want him to know the relationship is dead. He’ll rename you “cotton-mouth” in his contacts and stop calling.

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Actually you’ll need equal parts enthusiasm, lubrication and suction.

(Trigger warning. This is going to get really graphic so the squeamish should just skip to the comments section. Go ahead. Skip this.)

Good head requires multitasking (another reason I’m against it).

Lay him on his back. Don’t let him stand. You don’t want him to ever have worry about locking his knees. So on his back it is.

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Make sure you warm him up with a handy if he’s not already at attention.

A good handy uses both hands, lubed up, twisting gently in opposite directions and occasionally sliding his penis between you index and middle finger.

Once he’s at attention. This is when you lean in and with your hands still gently twisting around the shaft, you swirl your flattened tongue around the tip, then down his frenulum, then suck. Really suck. Suck. Suck. And then repeat. All the while you should be moaning for the added vibrations. And you keep this rhythm. Constantly changing it up is not the move. The best way to build on sensation is to maintain a rhythm.

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Now after you done this for a while and without stopping any of it, move one hand from his shaft to his jewels. And cup them up and towards him. And then release. And repeat.

So now, while you’re swirling, licking, sucking and moaning with your mouth, you’re also stroking with your dominant hand and cupping him with your other.  All the while, you’re listening and paying attention to him. The hitches in his breathing. The small moans. How tightly he grabs your head. Make sure you make eye contact as well if he’s into that. And make sure you pretend to choke (or really choke, like I would) if he’s into that. (I’m a method actress). Once you feel like he’s peaking (his jewels will tighten up) you should then go for the straight suction. Shaft then jewels. Jewels then shaft.  Making sure to keep moaning and maybe start playing with yourself.

This straight suction section is always going to take longer than you expected but you have to power through. No stopping.

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And then when he orgasms, you have to swallow. Ghost head definitely swallowed. And remember you’re competitive or whatever. And then you should get a warm towel and wipe him down. And then when you crawl into bed with him. Be the big spoon. And just as he’s dozing off. You kiss his shoulder and whisper “thank you”.

Now you’ve made the highlight reel.

And maybe, in a few years, while in bed, he’ll mention you to his wife.

Jay from Queens, NY asks:

I need an outfit for a boat ride in August. It’s basically a day party on a really nice, really big yacht and the tickets were $90 dollars all inclusive (unlimited food and drinks). It’s gonna be classy n’ shit.

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Two rules. 1. Don’t wear shorts unless you’ve been committed to leg day. 2. Remember to lotion the creases between your fingers and your WHOLE foot.

And wear something like this.

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Ignore that ugly ass belt though. And do not wear hard soled shoes. And do not roll up the bottom of your pants like an animal. The bottom of your pants should be half an inch from the tops of your shoe. And the shirt should pass the raised arms test. And notice I chose white pants for that beautiful blue shirt instead of the cream pants the model is wearing with it. Yes, they’re not both “white” pants. And make sure the pants hug your package (a little).

It’s 2016. Grow up.

Also, the only accessories you need are a watch and sunglasses. No chain. No earrings. No rings. No hat. And bring chapstick.

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Go to JCrew and Cole Haan for the look.

Shirley from Dorchester, MA asks:

What’s the best-case scenario for a Trump presidency? #possiblebrightside

I’ve thought about this a lot. And our best hope for a Trump presidency is if he turns out to be a 21st century Chester A. Arthur. Now, Chester, although not well known, is considered by many historians to have been one of our best presidents. And there had been no indication that he would be a good president. You see, Chester (look him up) had been a crook his whole life. And he’d strong-armed his way into the Vice Presidency, like crooks do. And then, James Garfield, the current president, gets assassinated and just like that, this long time enforcer {see: thug} in the republican political machine becomes president.

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But then a strange thing happened, as sometimes happens when one is entrusted with the weight of the highest office, Chester rose to the occasion. And he takes his job very seriously. In fact, he spent his presidency successfully fighting the same corrupt politicians he’d been in bed with, which must’ve made for some awkward pillow talk. You see, Chester knew where all the bodies were buried. And they couldn’t bullshit a bullshitter. He was basically a 19th century Frank Underwood—if Underwood had a change of heart. So that’s my best hope for a Trump presidency. That somehow the gravity of the office will make him give up his asinine ideas and put the country first. For real.