January 14, 2014

Dear Darren, 

My boyfriend insists on going down on me every time we have sex, but I’ve never been a fan of it (no matter the guy). It’s basically turned into a chore every time we have sex. I know he means well, but I don’t want to have to keep lying to him. How do I tell him that I don’t want him to go down on me without hurting his feelings?

Kate, Mt. Washington

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Dear Kate,

It’s best not to be honest about it because men are sensitive about cunnilingus. It’s kind of our thing. How would you feel if he told you you were bad at driving a car? It’d feel like an unfair stereotype, wouldn’t it? Personally, I’ve done cunnilingus so many times it’s like driving a car but maybe your boyfriend hasn’t so I’ll try to help you out.

One time, in college, I had a beautiful sophomore in my bed after a night of college partying. She was undeclared, but she could have majored in sex. She was that good. We frenchkissed naked for a while, then I started kissing and chewing on her collarbones. She was super into it.

By the time I reached her midriff, she grew frustrated with sexiness and pushed my face in between her legs. I knew just what to do. Rubbing my nostrils and goatee above and below her vagina, I began reciting the Pledge Of Allegiance, as I had been taught, putting emphasis on the sounds that required a lot of teeth, tongue and lips. She winced with joy. By the time I reached “one republic under god”, she was literally moaning.

She got so aroused that she began pushing my head violently into her business. Every time I tried to gasp for air, she’d grab the hair on the top of my head and direct me back to her crotch, not unlike the rat in ‘Ratatouille.’ Despite, or maybe because of the lack of oxygen, I was super into it.

That is, until I detected a strange feeling in the top front portion of my face, right between my eyes but a little bit lower, in the bridge of my nose-area, it felt like my sinuses were emptying. That’s when I realized the facial-vaginal collisions had given me a bloody nose. I was leaking blood like a faucet.

It was dark so she couldn’t see it, and she was also drunk so she didn’t notice the puddle of blood gathering about her anus and vagina. My initial reaction was to get up and plug the wound, but just as I was about to do so, I noticed the immense upswing in arousal she was displaying. So I kept going. The more I bled, the more wet with blood her vagina got and the results were phenomenal. I don’t want to be coarse, but she came like a faucet.

The next morning, I tried to blame the pool of dried blood on her, by implying that maybe she was a virgin and that the bleeding was hymen-related. But she insisted that she wasn’t a virgin, so I tried to turn it into a compliment, by telling her she had the vagina of a virgin. She was flattered. Once she stopped crying, she called her sister to pick her up and went to wait for her on the porch.

Since then, I’ve used blood lots of times and it works every time, as long as she doesn’t notice the blood. Noses, gums and fingernails are all viable blood sources that you can open up without too much fanfare, as long as you’re subtle about it. These days I just make a little cut while shaving, then open it back up a few minutes before the cunnilingus and I’ve got gallons of the stuff ready to go. I’ve also noticed that saliva works.

So, Kate, my advice is to use blood.

Love,

Darren

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January 10, 2014

Dear Darren,

Last year, I broke up with my girlfriend of four years and ever since, I’ve had a problem with premature ejaculation. The girls I’ve slept with recently are way hotter than I’m used to, so I’m worried that I don’t have the stamina to make it above my league. What should I do?

Anonymous, North Oakland

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Dear Anonymous,

Changing leagues is always tough, but even with its challenges, upgrading to a higher echelon of babe is what you’d call a “good problem.” Premature ejaculation is the easy part!

I’ve never had this problem myself, but one thing I like to do is just pretend that it didn’t happen. She won’t notice unless she sees it, so you’re going to want to make sure your penis is not exposed for her to witness exploding. Hide your penis in the vagina, or in a darkly colored condom, or sometimes I just tuck it back between my legs and cum into the blanket. They never notice.

If you lose control and she happens to witness the ejaculation, play it off like it’s pre-cum. If she acts like that’s not a thing, tell her to “look it up” and shoot her a mean glance, but don’t try to explain what pre-cum is, you’ll sound foolish. If she doesn’t believe that it’s pre-cum, just tell her it’s pee.

One time, I hooked up with a beautiful South American, named Diane, whose intense beauty and robust figure made me cum extremely quickly. This was at a room at an elegant hostel in Toronto where we were both staying, sharing the commune room. I met Diane playing foosball in the game room. She spoke English terribly, but luckily we both spoke the language of love: Cantonese. After some white wine and poutine, a spark was sparked between us and we were soon entangled in each other’s arms, nude, in Diane’s bed. Sex was gonna happen.

Her body was warm and profoundly soft and I soon found myself overwhelmed. In a sudden rush of wild and primeval ecstasy, I shot an inordinate amount of semen onto her stomach and bellowed a masculine moan. When I came to, Diane was wearing a look of considerable emotion.

She grabbed my t-shirt from the floor and cleared the semen off her abdomen, then instructed me to get hard again “so we could actually have sex.” I agreed and started trying to get erect, while Diane scowled at me lustily. By the time I was hard again, she said she didn’t feel like it anymore. The next morning, Diane was gone from the hostel and out of my life forever.

The point, Anonymous, is that Diane was out of my league and I prematurely came on her and now everything’s fine. Don’t worry about how you cum, just do it.

“Cum early and cum often,” I always say.

Love, peace, and potato latkes, Darren

January 2, 2014

Dear Darren,

I’ve been dating my gf for three months and I can tell she’s already getting bored in bed. I try to mix up positions and act dominant but I’m not a very sexually adventurous guy. I want to stay with her but I’m afraid I can’t hold her interest. What can I do to spice things up in bed without getting too crazy?

James, Shadyside

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James,

It sounds like the problem is that you’re not good at sex. Have you considered that maybe she’s not the one for you? Sex is the handshake that makes the business of love happen. And it seems like she’s better at shaking hands.

This may be harsh, but your girlfriend deserves to get her sponge wrung by somebody who knows how to do that kind of stuff, somebody on her level. What you need to do is find somebody as sexually terrible as you are. You’ll feel better.

If you really think this is just a matter of spicing things up, you could try something I call “Jiggledick,” a portmanteau of “dick” and “jiggle.” I invented this technique one day while I was watching an erotic video starring a redheaded bikini model shot on a webcamera. She had large breasts.

I remember after she helicoptered her boobs, she reached into the hamper, and pulled out the single largest vibrator I had ever seen in my life. It was the size and shape of a large penis. She looked into the camera hotly, then turned on the vibrator. It started flopping and convulsing in her hands, in a way that I remember thinking looked fish-like. She used it on her vagina, rubbing it on the top part and then inserting it into the bottom part, then started yelping with pleasure. She was super into it.

That’s when I thought to myself, “if gals use vibrations to get orgasms, then why don’t mens’ penises vibrate?” I pulled down my shorts, stood up and started mock-lovemaking the air like a human vibrator, shaking and jiggling my lower half as though I were being jiggled. After a minute, I flipped her over into imaginary doggystyle and accelerated the vibrations, letting them spread over my limbs, sort of like being electrocuted or having a seizure. My cousin Brandon has epilepsy so I know. I shook from head to toe, my arms and legs flailing passionately, while maintaining polyrhythmic thrusts with my hips and while also masturbating. It was a “eureka” moment.

Since that morning, I’ve used jiggldick every time I’ve had sex and it has worked I believe. So if you’re committed to making your relationship work, James, this is one thing you could try to make your girlfriend like having sex with you.

But remember, it only works if your whole body is moving and you are committed to the dance. “Be the vibrator,” I often say. Also, this technique works much better in doggystyle. Don’t use the dildajiggles in missionary, it will terrify her.

Good luck James.

Love,

Darren

PS: Brandon later pointed out I should have called this move “sexilepsy.”