November 12, 2014

Dear Darren,

I’ve been dating a girl for the past few months. She is insanely sexy and awesome to be around but she’s a bit of a prude. Handjobs and nothing else. She’s not a virgin or anything, she doesn’t have a secret boyfriend, but I’m worried about asking her about it. She just always prefers to jerk me off. What the hell is going on with this girl? 

Thad, Lawrenceville


Dear Thad,

Getting jerked off all the time doesn’t sound so bad. That’s one of those “good problems.” Handjobs are essentially the stickshift of sex acts, and to me, there’s nothing sexier than a girl who’s down with a manual transmission, if you know what I mean. (It’s a sex pun).

In the olden days, handjobs were sex. The penal-vaginal sex we know today didn’t popularize until the middle ages. Until then, it was all hands. Perhaps your lady is a history buff?

This reminds me of a girl I once dated, who had a similar passion for manual evocation. She was super into jacking me off. Her name was Tabitha, and throughout the two months we canoodled, we didn’t make it past third base, and not the sloppy kind. It was my Handjob Summer, capital H.S., and I was grateful to have it. We’d meet behind her cabin after lights-out and she’d just go nuts on the thing: passionately pulling, eloquently squeezing, twisting terrifically. Every girl has a fetish and Tabitha’s was handjobs. I loved her for it. Later she got sent home for blowing one of the counselors.

If you’re still feeling frustrated or bored, here are a few ways to make it feel less like a hand-JOB, and more like hand-GAME:

1. Beforehand, write a message to her on your penis using magic marker. It will be illegible when flaccid, and she’ll be super excited to see what it says, like a neat riddle.

2. Ejaculate prematurely to compliment her.

3. Put one of those funny handshake buzzers on your testicles so when she reaches down there she gets a shock she’ll never forget. You guys will laugh and laugh.

4. Create a spreadsheet to map the details of each handjob and see if you can beat your best time. Share it with her on Google Docs. This will show her you’re paying attention, you’re organized, and proficient in Microsoft Office.

5. Return the favor, dummy. That’s why God made fingers.

Hope that helps.




April 2, 2014

Dear Darren,

I have a shy bladder. My friends make fun of me constantly about it. I can’t stand pissing in public and the lengths I go to avoid it are embarrassing. Buccos games, tailgates, parties. I’m constantly stressing out about it. My girlfriend acts like I’m such a pussy because I can’t just go on command like most dudes, but I can’t seem to get over it. What do I do?

Pete, Friendship


Dear Pete,

Sorry about your weird problem. That’s no way to live. I bet it’s a brainpenis connection disruption, probably somewhere in the torso. Lucky for you, I’m profoundly “in-the-know” on this subject, so if you take my advice word for word, by tomorrow night I’ll have you peeing like an Australian: outside.

You see, bladder control is the cousin of sexual discipline. Once you’ve mastered pee and poop, taming your cum is like a walk in the park. So, here are a few ways to get your public pissing fears under wraps:

1. Hold it indefinitely.

2. Tell everybody you have diarrhea and just stick to stalls. You’ll have to sit down to sell it and farting also helps.

3. You only get one of these, but in a pinch, just go in your pants and play it off as a funny gag or an impression of someone you know who pees their pants.

4. Hold it until pee is literally dripping from your penis, then run to the nearest acceptable location and let it rip. More on that later.

5. Tuck your genitals back like Buffalo Bill. It works.

6. Suck it up and just pee on the fence with your friends like a normal person. If one of your friends makes fun of your probably small penis, just call him a “gaywad.”

*If you’re also having problems pooping in public, most of these suggestions still apply. 

If those don’t work for you, here’s a deep cut from my sexual past that might help you out.

A few years back, I was on a date with a vivacious Asian named Bethany. She was an absolute dime, as well as vivacious. Things had been going hotly all night, we were vibing on each other like ecstasy and viagra. Sex was on the menu that night and we had ordered a big platter for two. She was super into it.

But on the way back to her place, I began to notice that I had to pee really bad. Before long, I felt an ocean of urine starting to erupt in my loins. Gallons of Yeungling had made their way through my digestive system and now, they wanted out. In an effort to reverse the impending stream, I started mashing my penis inward, kind of stuffing it back into my body to relieve the pressure. Eventually Bethany noticed, so I played it off like I was jerking off.

“Just getting myself ready,” I shouted.

But I couldn’t hide it much longer. Every bump in the road was like an earthquake in my bladder and I knew the subsequent tsunami couldn’t be far behind. I asked Bethany to please pull over so I could take a piss and she said “oh, we’re like five minutes from my house.”

I stewed a moment. On one hand, this urinary urgency might ring feminine to her and she might decide she doesn’t want the biracial sex platter after all. On the other hand, I might piss my pants in her car. I couldn’t risk it. So I asked again that she pull over. She laughed and said “we’re here, I’m just looking for street parking.”

“I’ll just get out here,” I said.

“Chill out,” Bethany laughed. “It’s two seconds.”

“Damn you to hell!” I shouted.

I leapt out of the vehicle and ran for the nearest tree, unbelting and unzipping as I ran. As soon as my penis felt air on its face, it began furiously spouting urine indiscriminately. On my feet, on my shorts. I hadn’t even reached the tree yet, I was just a running, peeing man. But I didn’t care, it felt amazing. To this day, that sensation remains the single greatest orgasm of my life and it wasn’t even an orgasm. I must have peed for five full minutes once I reached the tree. By the time I was done, my flip flops were soaked and I was panting like a fat dog. I felt like a new man.

So I ran back to Bethany and apologized for damning her. To my surprise, she was un-repulsed and still super into it. We went upstairs, I changed out of my wet clothes and we embarked on a nightful of erotic canoodling. Compared to the divine ecstasy of my epic urination earlier, the orgasms were sort of by-the-books, but I was happy to learn a new trick nonetheless.

You see Pete, my bathroom emergency had actually turned Bethany on. It may not be sexy on the top layer, but genital passion is genital passion, it doesn’t matter which function is passionate. Having to pee a lot is basically the cousin of virility. Semen may be traded at a higher value than pee, but they’re both the currency of manliness. So own your digestive system, own it up Pete. Take pride in your pee, because no one else will.

Love, Darren

February 17, 2014

Dear Darren,

I think I gave my gf a very rare, non-fatal std. It has some very odd symptoms. She hasn’t noticed yet but I think she will soon enough. What do I do? 

Paul, South Oakland


Dear Paul,

Dude, you got Darren’s Disease.

For my readers who don’t know, I’m something of a Patient Zero in the world of sexually transmitted diseases. I’ve been called a venereal astronaut, a lab-rat lothario, an erotic rocketship, a pioneer on the plains of sexual exploration which is to say I have an STD named after me.

This all began the summer before my junior year at Pitt. I had a Residency at UPMC, working in the Department of Cell Biology and Physiology in the Mail Delivery Department. My duties involved walking around campus, bringing vital medical documents from building to building to exchange envelopes and signatures from important people. Basically a doctor. It was very erotic.

Each delivery on my route came with its own ejaculatory potential, by which I mean the departments were populated with vivacious women at every stop. I was cooed and wooed from all angles by seductresses of all ages. I had my pick of the litter. When I wasn’t rubbing elbows with the voluptuous secretaries, I bumped kneecaps with the looser nurses. It was nonstop. I slept with so many of them that by summer’s end, I could get through an entire afternoon’s deliveries without making eye contact with a single female. It was the dawn of my sexual prime.

It was also the dawn of my not using condoms and the harsh venereal consequences that followed. I learned the valuable lesson that just because a woman works for a hospital doesn’t mean she isn’t a filthy person.  In late August, my penis began stinging. By the first day of classes, my pubic hair had uniformly ingrown. I’d later come to know these symptoms as the early stages of Darren’s Disease.

I was prepared to live with the forrest of infected pubis and the hot-sauce-penis, I’m no prude when it comes to bodily pain, but soon my situation worsened. Basically, my penis got dementia, my wires got crossed. Every time I tried to urinate, I ejaculated; every time I was set for orgasm, I peed.

Never mind the awkward faux-pas of having a rib-crushing orgasm at a public urinal or peeing in a girl’s mouth at the end of a blowjob; the pain of cumming flaccid and peeing hard was debilitating. Paul, I know you know what I’m talking about. It feels like your penis is a broken icicle melting in salt, right?

After a week of cum-covered toilet seats and angry, pee-drenched women, I finally went to the doctor for a cure. Needless to say, he hadn’t seen anything like it before. “Holy hell,” I believe he laughed.

“Perhaps my seasonal bout of promiscuity has concocted in me a cocktail of erotic infection,” I explained, “a sort of hybrid Super-TD expressed in stinging peeholes, pubic acne and some kind of Freaky Friday rendition of penal function.”

He said “what?” then prescribed me antibiotics, scheduled me for some tests, and told me to “keep it in the pants for a while.”

Those were dark months. When I wasn’t in bed, staving off urges of auto-castration, I spent my afternoons at the hospital being prodded with needles and genital x-rays by some of the very nurses who infected me with this tragic, biblical affliction in the first place. It was unspeakably unsexy, but I knew this was my cross to bear: fighting infection in the company of my infectors, balls the blue of the bluest color blue, paying my dues for a sinful summerful of profound sexual excellence.

“You play with fire, you get all kindsa diseases” my cousin Brandon told me.

The tests found nothing medically wrong with my penis and by Thanksgiving, I was peeing and cumming totally separately and on purpose. Sure, my campus reputation took a brief hit, but those same jilted nurses who spread the rumors were also spreading an infant STD with my name on it. I think it’s likely, Paul, that your unnamed, very rare, non-fatal STD is the great granddaughter of Darren’s Disease. And as much as I’m sympathetic, I feel a strange pride in knowing that she’s still kicking around South Oakland, confusing women and destroying the lives of college-age males.

As for your specific problem Paul, don’t worry about it. Women couldn’t get Darren’s Disease if they tried. It’s a masculine affliction and seems to lay dormant out of respect for estrogen, much like its namesake. If you’re still peeing in her mouth at the end of every blowjob, I found that some women mistake it for an extremely large, unhealthy ejaculation, which can be a turn-on if you play it right. Whatever you do, don’t fret too hard.

STDs are signs of a life well-lived. STDs are battle scars. STDs are the tatters in a tattered flag. They’re a testament to your joie-de-vie. They’re a misdemeanor on a rap sheet. They’re the stuff that “doesn’t kill you” as the old saying goes. STDs are an invisible tattoo on your personality that tells the world that you’re much more than simply alive, you are LIVING. Amoxicillin works!




February 4, 2014

Dear Darren,

What is the best place for a first date in Pittsburgh?

Joe, North Side


Hey Joe,

A first date is like that thing where dogs smell each other’s anuses when they first meet. It’s an audition for your anus. The location of your first date shouldn’t matter to you any more than the location of the dogpark matters to the dog when he’s snout-deep. Don’t trick yourself into thinking location matters. I don’t care if you’re drowning together at the bottom of the Allegheny with sterling silver cinder blocks tied to your feet; if she doesn’t like the smell of your penis, you are donezo pal.

If you have to pick a place, make sure it’s unique, exclusive or dangerous. You want to stick out. That way, even if the date is bad, she’ll tell her friends about it and one of them will be super into it. If you’re having trouble getting started, here are a few options to get you going:

1. Night-picnic on a tandem kayak

2. A concert of her favorite songs

3. Throw pennies off the top floor of the Cathedral

4. Dinner at a romantic museum

5. Burn up the dance floors in the South Side

6. A half marathon

7. Build-your-own FallingWater

8. Casino brunch

9. Bike jousting

I once had a first date on the Monongohela Incline with a buxom Monongohela Incline operator named Irene. Her shift had just ended when I entered and we struck up a conversation as we waited for the trolly. Her uniform clung to her feminine shape like a condom on a penis, and she spoke to me of the weather and Inclines. But it was clear what she really wanted to do. She wanted to crotch-wrestle me all the way down to Station Square, and I was about to make weight (like a sex pun).

When the trolly arrived, I held the door and beckoned her into the car so we could “share the view.” She sat right next to me. For a moment, Irene and I sat in hot silence as we descended, the ancient gears and erotic pulleys sliding us down-mountain. All was well and right in the world, two beautiful strangers bathed in city light, gliding asunder and steaming up the night sky with our genitals. I was about to make my move when suddenly, the car stopped short and sat suspended, mid-mountain, halfway down the Incline. It was unspeakably dangerous.

As I peaked out the window thousands of feet down the looming rockface, my heart began racing and my tear ducts emptied cathartically. Irene told me to “get it together” and swung into action. Cool as an ice cube, she telephoned her colleague up top and started mercilessly asking him what caused the car to stop. I believe it had something to do with electricity. Once she hung up, Irene assured me we’d be moving in no time and gave me her jacket. I wiped my nose and smiled at her, and she smiled back. That’s when I realized this was about to be the hottest first date ever.

“I’d like to kiss you,” I said.

Irene immediately started laughing romantically and pinched my cheeks between her elegant knuckles.

“I’m married, but flattered,” she said. However, I could tell that she was very aroused and was still super into it. The chemistry was electrifying, the circumstances were perfect for naughty, public sex. But maybe I needed to prove my worth first. Perhaps my weeping had stifled her libido and led to that flimsily laid marriage defense (though I often find a shameless spell of crying in front of a potential lover has the opposite effect. Crying is a form of bravery in sexual warfare). But seducing Irene was going to require a more nuanced approach.

“I’m going to break this window, jump down onto the tracks and climb back up to the top to get help,” I announced and started checking the windows for weak places to break the glass, winding up my fists like tiny boulders with fingers.

Before I could even smash the first window, Irene was begging me to stay, arguing that I’d kill myself if I tried to climb the tracks. “It’s basically a ladder, and what are ladders if not ambitious train tracks?” I countered. “What are train tracks but lazy ladders? They’re shaped very similarly.”

Despite her protests, I began cocking my muscular shoulders and prepared to knock the window clean off its hinges when suddenly the older gentlemen sitting next to us put me in a headlock and Irene grabbed me by the arms and wrestled me to the ground. They did not want me to leave.

We tussled, the three of us, a tumbleweed of limbs and flesh and warm elbows passionately churning in over itself like a pile of sleepy puppies. We rassled.

Just as the commotion was escalating, the Incline kicked back into gear and resumed its graceful descent down the mountain as though nothing had happened. We responded in kind, pretending we hadn’t just engaged in a primal three way tango of strangers. Irene and the old man unhanded me and encouraged me to “calm down.” I agreed and winked at them and we sat out the remaining leg of the journey in silence.

By the time we reached the bottom, all bygones had been begotten and we parted ways on positive terms. Irene called me a “wild one” and smiled a sexual smile and went to meet her husband for dinner at Bar Louie. The old man told me to “take care of myself” and shook my hand. I apologized to his grandson and they left.

The lesson here, Joe, is that a bizarre date is just as good as a good date. Where it happens, what happens when you’re there; these are just petty details. A first date is all about two people dipping their toes in each other’s lovepools and deciding if they wanna jump in. The location of the pool has nothing to do with it.

Irene and I never went on a second date, but I had fun and I lived to date another day. And isn’t that what life is really all about?



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


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.



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


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



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.



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