Best of Sex Advice

As far as months of the year go, August is one of the best for having sex. Sure, you probably think we say that about every month—but really, if there was one month that we'd promote recusing oneself from the computer to get laid for real, it'd be this one. Summertime isn't just a song by Will Smith—'tis the season of sand-encrusted bikinis, humid nights, third-degree sunburns, and a million-and-one other reasons to get buck naked and intermingle SPFs with the object of your desire. But before you venture out to try your chances, best spend a few more moments within the safe confines of cyberspace reading up on the best sex advice the internet has to offer. Because if the intention is to get caught with your pants down, you're going to look awfully silly standing their not knowing what to do next...

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TimeOut.com, Get Naked:

If I had a trademark on masturbation (hmm, perhaps I could still have a go at mazturbashun™), I'd forbid you from partaking in it because of the way you're perverting such a solemn and sacred act. The universe has granted us the ultimate blessing by placing our hands within rubbing distance of our pleasure centers, and there you go making a mockery of the Grand Plan by introducing ugly old men into the equation. Don't you realize--if only you had your head in the game--that every one of your orifices could be filled (simultaneously) by the entire Italian World Cup soccer team? That George Clooney could be humming "La Marseillaise" into your clitoris? That you could be dildo-fucking Brad Pitt's slab-'o-granite ass? Such is the power (and joy) of masturbation. I know I'm being a bit harsh, but I just hate to see quality fantasy time frittered away so pitifully. To be honest, you're not the first woman I've encountered who's had this particular dirty-old-man quirk, but... even though you find such men repulsive in a real-world situation, perhaps it's the idea of how they would react to you (i.e., with saliva dripping from their crusty, gum-diseased mouths all the way down to their rock-hard, droopy-scrotumed, gray-bushed dicks) that really gets you off.

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AskIsadora.com, Ask Isadora:

This may not seem like a serious problem, but it is to me. I met a man at a party and we have gone out three times since. There's a lot of mutual interests and a hell of a lot of chemistry. We've made out for hours and done everything but "the act". The thing is he has no idea how old I am. He says things like "at our age" or "when we were in school". Isadora, he's probably in his early forties. I'm 63. I'm afraid if he finds out he's kissing someone his mother's age, or worse, having sex with her, he'd be revolted. I know I look good and can easily pass for fiftyish, but that's with my clothes on. When he sees that my breasts sag, my tummy is soft and poochy and my thighs are crepey he'll know the painful truth. I really would like to have sex with him. I'd like to have a love affair with him, for as long as it lasts, and I don't know how to tell him my age, or whether I should, or when, or how. Help!

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AskHeartBeat.com, Dear Ms. HeartBeat:

Women have big mouths, cannot keep a secret and want to tell every damn thing they think and say and do. I don't understand it. Don't you realize that some of who and what you are as a woman is nobody's business but your own? You have things in life that need to go to the grave with you as YOUR SECRET and no one else's!! So "no!," you do not tell him anything. Keep your mouth closed about what you ALMOST did. What in the world would you tell him for? Women kill me with this "I need to be honest" shit!

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Nerve.com, Miss Information:

You're lucky you have a vagina, Safety Dance. They have a reputation for going on the fritz, and therefore they're a rich source of excuse material. If you can't muster up the nerve to ask Guy B to use a condom flat out, why not tell him that you suffer from frequent yeast infections, bladder infections and infection infections, and that condoms help prevent them from coming back. Unless you're dating a gyno, you're probably not going to get called on it, though it may put a damper on the oral sex.

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Eye.net, Love Bites:

I loved the article you wrote about visiting the many small porn theatres in Toronto. I was wondering if you found any stores that had good ol' glory holes. I am looking forward to taking my wife to one and having her in the booth servicing the many cocks that would come through the hole.

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The Stranger.com, Savage Love:

I'm a 100 percent straight guy from Toronto, VGL, all that shit. My girlfriend took me to a gay bar in Vancouver, where she's going to school, and this good-looking boy started coming on to me. My girlfriend asked me to make out with him because she thought it would be hot. Long story short: He came back to her place with us where he acted as my personal fluffer. He blew me while I ate the girlfriend, stroked me after I put the condom on, and in general did everything he could to keep me rock hard--for the girlfriend. Then I fucked the hell out of my girl while my fluffer licked my balls and ass. I never came so hard in my life. I thought I was going to shoot a few vertebrae right out of my dick. I want to do this again, my girlfriend wants to do this again, and my personal fluffer wants to do this again. No real problem here, Dan, but do you think I should turn in my straight-guy card now?

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AdviceGoddess.com, Amy Alkon:

This is gonna sound like a joke, but I swear it's not. I'm an unattractive guy (not hideous, but pretty ugly) who's overweight and really socially awkward. When it comes to talking with women, I just clam up. About the only thing I have going for me is a huge penis. While attractive guys with tiny penises and ugly dudes with suave personalities can land women, I never even get a girl to go home with me, let alone get into a relationship, which is what I want. I know a lot of women don't care about size, but I also know some do. Am I crazy to think some women would look past
my faults if only they knew what I was packing?

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Nerve.com, Sex Advice from 90's icons—Samual "Screech" Powers:

You got to tap it so good that she falls asleep. If she doesn't fall asleep afterwards, you have no chance. Rock it to sleep, baby. My test is that I'll pop in a movie, but first get her down. If she can watch the movie afterward, I didn't do it right...

To be slick, I always take a dip in a spa. The girl feels cool because she can sit down under the water and only her head is exposed. When the guy gets out, he should do the gentleman thing and hold the towel up for her. Hold it in front where you can't really see so she feels like it's a safety shield. Then you can bring the towel around the back. Don't wrap her around the front like a mummy, because then it's like you don't want to see her. Swing it around the back so that now she's totally exposed. Then take a shower to clean off the chlorine. Start out in the bathing suit and then those can come off in the shower.

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Previously: Best of Sex Advice Archive