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.




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