Sexytime Dilemmas: Facials, Masturbation and Butt Fingering

If you’re having consensual sex with someone you like, and you’re both turned on by the idea of him cumming on your face, then you should do it, duh! It’s bad to analyze these things so much that they lose their spontaneity and hotness (and the rules of “real life” don’t apply in sex anyway, so whatever). Basically, we should all stop being so hyper-aware of the sociopolitical context of our sex lives, and start focusing on other, more important things, like becoming famous.

Help me out here: how and when do I stick my finger up a guy’s ass? A lot of men think that’s off-limits, so I’ve never ventured back there, but I want to massage someone’s prostate goddamnit! How can I make this work?

-Susie, CA

If you want this to work you’re going to have to be very delicate, and take things slowly. No one wants a dry finger shoved up their butt at random. In my experience, guys are generally more open to new concepts, and trying out new things, when you have their dick in your mouth. (This is because fellatio slows their brain down to a point of temporary retardation, which means their guard is down.) This is why mid-BJ is a great time to bring up things like, “Are we official?” or “Can I please borrow your car and $700?”

So, while you’re sucking, start playing with his balls and then slowly move moving your fingers back in the desired direction. Be conscious of how he’s responding to your touch. If he flinches as soon as you start poking around in that area, that’s not a good sign, but don’t give up hope just yet. Wait a minute or so, then do something fancy with your tongue to distract him and try again, rubbing lightly around the outside of the hole, as not to scare it. It might take a while to “feel out” (lol) if he’s going to be down for butt stuff, but even if your first attempt is a total failure, that doesn’t necessarily mean it’s never going to happen. Maybe it just wasn’t the right time, ya know? (To be honest, even if you’re someone who’s generally into anal, sometimes you just don’t want someone back there, like if you have to go to the bathroom or if you’re hemorrhoid is acting up or whatever.) Basically, never give up and remember that with a little perseverance you can do anything you put your mind to, Susie! Just think: it took NASA a long time to figure out Mars, but they never gave up and then finally last month they achieved their goal of DJing a Will.I.Am song from space. #inspirational

Also, this is sort of a no-brainer, but make sure your nails are trimmed and that your fingers have some spit or lube on them when you finally go for it, because intra-anal lacerations are not not glamorous.

Hi, I’m 27 and only recently left the church. I’m still a virgin and for most of my life I didn’t believe in sexual gratification, but now I’m looking to have my first self-orgasm. I was wondering, is this a subject you could help me on, or should I just ask someone else? I’m a bit embarrassed and don’t really have anyone to ask.

-Michael
Well Michael, as you sent me this question via email, I assume you have internet capabilities. The great thing about the internet is that it’s full of useful information, most of which is easily searchable through a popular website called Google. I’m almost certain that if you put “help with sexual gratification” into Google that there will be at least, like, six or seven billion videos of guys “self-orgasming” for you to watch and learn from. But that’s just a rough estimate.

As I understand it, an efficient way to induce self-orgasm in men is to simply hold the penis with a loose fist and then slide the hand up and down the shaft until a milky gunk comes out. This will induce a full-body sensation not unlike that of Jesus shining his love-rays down onto you from the hereafter. Except times ten.

You’re welcome!