Advice

On being a kinky bastard.

I never have sex with my girlfriend because the things I want to do in bed are things that would make her break up with me. I don’t think she’s into Sasha Grey type porn, and I don’t want the police called on me for trying to find out.

Um, did you ever consider sitting down with your girlfriend and, you know… talking to her?

Use your words, big guy. Don’t assume that she’s not into Sasha Grey type porn, but then again don’t start spitting in her mouth and throwing lit matches on her without a little pre-game pow-wow.

Give her a heads up, get her permission, and pick a safe word.

If she’s not down, at least your break-up won’t involve law enforcement.

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Advice

On putting him in his place

I don’t have orgasms when I have sex. I’m honestly not that worried about it because I have a pretty damn good time regardless, but the guy I’m screwing right now has told me I am one of two girls he has ever slept with that couldn’t have one. First off, I really don’t believe this and I think he has just been fooled by a good fake orgasm one too many times. But still, it gets really annoying when he says shit like that like there is something wrong with me so what kind of sarcastic and on point comments do you advise using when shit like this comes up?

If you want to crush his ego, fake an orgasm. When he acts all pleased, tell him you faked it and that he’s one of two guys you’ve ever slept with that couldn’t tell.

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Advice

On girl-on-girl.

Have you ever fucked a girl? And if so, are you bisexual, or just open in bed? Because I’ve always been interested in having a threesome, or foursome, or however many, but I’m not bisexual. Thoughts? Concerns?

The word fuck doesn’t seem right, but yes, I’ve embraced my bisexuality and had plenty of sex with women. I don’t label myself bi, but that’s because I have a problem with labels, not my sexuality.

Interestingly, almost all of my girl-girl experiences have been in the kind of multiple-partner scenarios that seem to have piqued your curiosity.

I’ve gone down on a number of girls who, like you, would never consider themselves bisexual. So really, when I hear the phrase, “I’m not bisexual,” I find that it could mean a number of things.

Sometimes it means that you don’t find women sexually attractive and you never will. That’s perfectly fine. Some folks really are a zero on the Kinsey Scale, and if that’s you, it shouldn’t have any effect on your ability to enjoy threesomes, foursomes, and moresomes other than having fewer people to fuck at any given moment.

Sometimes, “I’m not bisexual” means that you haven’t yet fully processed your sexuality, and regardless of any curiosity or latent tendencies you may have, there’s still a bit too much shame in your standard American upbringing to acknowledge the possibility of hitting a one or a two on the Kinsey Scale.

Sometimes, “I’m not bisexual” is just pure fucking denial, whether deliberate or unconscious. This probably doesn’t apply to you, but I’ve come across it before (usually from a girl who later confesses that she couldn’t wait to get me naked, but she didn’t want her boyfriend to think that she was a lesbian. Sad, but true.)

Either way, “I’m not bisexual” is such a self limiting phrase. It puts you in a box.

Instead, try the phrase, “I haven’t found myself sexually attracted to women so far.” It’s a much more open way to approach your sexuality as you start exploring, and if you never get turned on by a girl, that’s fine. At least you’ll know you weren’t closed off to the possibility.

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Best-Of Advice

On one night stands

i’m in college, i got blackout drunk and fucked this really adorable guy last night and he left his socks here. what do i do about that shit. in general, what are the rules on one night stands? sounds ridiculous, may still be a bit drunk, but i think you get it.

Nice.

First things first. It’s Sunday morning. Go have a Bloody Mary.

Now, as for the socks, throw ‘em in your dirty laundy. Wash them. Start your collection. I guarantee by the time you graduate you will have a respectable number of t-shirts, boxer-briefs, socks, and of course the occasional hat, piece of jewelry, or other interesting shred of evidence.

Over the years, I’ve filled an entire drawer just with the random stuff I’ve found on mornings after. I’ll spare you the full inventory, but highlights include a full clip of 9mm ammunition, a pink double-sided dildo, and a La Perla thong that belongs to one of the current stars on the Disney Channel (and no, those items are not from the same night.)

As for proper one night stand etiquette, if your adorable guy wants his socks back, it’s his responsibility to ask. Most guys consider small items of clothing to be an acceptable loss, especially if they got laid.

Any item above a t-shirt — a hat, jacket, or scarf — may have been a deliberate leave-behind as an excuse to call you the next day. Don’t get your hopes up with socks, though.

Feel free to keep the collection in rotation. Future one night stands might need a spare t-shirt or pair of socks — trust me, it happens. When they do, let ‘em choose from your collection.

In general, though, one night stands are best left to just one night. There aren’t any hard and fast rules other than being respectful the morning after. That’s all you owe each other. Respect.

You don’t owe him a morning quickie or your phone number. He doesn’t owe you breakfast or a phone call. The fewer the expectations, the less awkward the morning will be.

How’s that Bloody Mary tasting? I think it’s time for me to go have one now.

Toodles!

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Advice

On cock size.

As I imagine you’ve seen / fondled / stroked / inhaled / fucked your fair share of cocks, I turn to you for the truth. Mine measures 7” long by 5.75” in circumference. How do I measure up?

Thank you.

Unbelievable.

The entirety of your male ego — every male ego — is a house of cards built on a fault line of mere inches.

How do you measure up? Fuck you for asking, that’s how you measure up. I should ridicule your penis size on general principle, but that would be unfair to all my male readers out there with rulers and the good sense not to ask a woman such an incredibly stupid question.

Seven inches is plenty good, guys. Big. Not the biggest, but a damn fine showing. No one’s ever gonna complain.

Honestly, though. There are so many more interesting ways for you not to measure up as a man. Why’s it always gotta come down to this?

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Advice

On sex toys.

I’m in college, haven’t had an orgasm yet, and want to get a vibrator so I can work on fixing that. Tips on choosing one? Brands, styles, how do I know I’m paying a reasonable price for reasonable quality?

I could ramble on about shopping for sex toys, but it sounds like you want to get down to the nitty gritty.

All you need to do is visit freddyandeddy.com. Look no further than their section dedicated to vibrator reviews.

The site is run by two friends of mine, a couple named Ian and Alicia. They’re two of the loveliest people you could ever meet, and I’ve been a loyal customer of theirs for years.

They’re like the Consumer Reports of sex toys. They’ve plowed through mountains of adult products to find the very best stuff. They try everything out themselves and write detailed, informative reviews so you really know what you’re buying.

They refuse to sell cheaply made crap, so regardless of the cost, anything you buy from them is going to be quality.

Don’t be afraid to give them a call. Just ask for Alicia, and feel free to let her know what you’re looking for and why. I promise she’ll prove more helpful than you could possibly imagine.

Best of luck with that orgasm!

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Advice

On ex sex.

Probably not the best idea to be a fuck buddy with an ex with whom you still have feelings for right?

Good, earth shaking, familiar sex at the sake of playing emotional Russian roulette…

Sounds shaky to me, but pretty damn irresistible at the same time.

What do you think?

He’s not a fuck buddy. He’s an ex. He’ll never be a fuck buddy. You’re having good old fashioned ex sex, which can be damn good if you’re careful.

Still, fuck at your own risk. There is no lifeguard at that hot tub.

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Advice

On bad sex

I’ve been in a whole two relationships before in my life, so I am aware that I am no expert and completely inexperienced. If I wasn’t I wouldn’t be wasting your time. So a little background info as short as I can make for you: First relationship- deadbeat boyfriend that ended up moving into my house because he was poor, pathetic, and quite possibly was just that crazy and controlling that he felt the need to be able to keep an eye on me 100% of the time. Mind you I’m only 20 years old and I was living with my parents during this. The living with me part only lasted a month, he drove me crazy and I had to force him to get his life together. He was mean and verbally abusive (and I’m not just being some whiney cunt, I was just a young and stupid girl and fell for his lies and bull shit and he belittled me and somehow got control over me, something that will never happen again.) Second relationship: sex. typical girl meets boy, gets fucked, falls for said boy and boy gets other girlfriend. again, and again, and again. So now, 6 months into relationship number 3, I’m looking for some harsh words of encouragement not fuck it up. Hes fantastic, sarcastic, cute at all the right times and just enough ass hole in him so hes not that nice guy that everyone always talks about wanting but doesnt ever appreciate when they get. The only problems we have are when we have sex because im inexperienced (I’ve slept around a little but I dont whore myself out to any guy with a big dick and a nice smile) and insecure. Its a weird situation though, I’m insecure because often we will have sex and neither one of us will come because I cant handle his dick without eventually being in a lot of pain and he is on some obnoxious mission to make me come. This shouldnt be obnoxious, but he should just realize that after awhile when im in pain shit just aint gonna happen. So, sorry for the ramble but heres the point. I need to hear it from someone whose gonna give it to me harsh and let me know how things really are. I dont want to feel insecure, but the fact is no matter how many times he tells me if i wont come theres no reason he should, i still feel like a pathetic ass hole when i cant do it for him. we have been screwing for months and pretty much have been doing it the same way until this week when we had sex in two different positions other then the 3 or 4 weve been doing the whole time. i cant get past the pain and have come to tears almost multiple times just trying to grin and bear it so he could get off. and keep in mind that this isnt some wham bam thank you maam kinda shit. the sex has never lasted under 15 minutes and is on average a lot longer then that. after 20 minutes of it it hurts so bad, and its a depth thing not a friction thing, because its never a problem of not getting wet. so, take from that what you may, and tell me something that can help if you will. I dont want my insecurities to fuck this up.

There are a couple of things going on here that need to change.

First, you need to recognize that he is just as inexperienced as you. Like every boy born after 1985 he learned to fuck by watching porn, and that leads to the kind of endless, detached meat pistoning that you describe here.

It’s bad sex, compounded by the fact that he’s got a big dick. Big dicked guys should know better. They don’t get to go balls deep. Bruising your cervix is not cool. You should not be letting him pound your uterus. Since he doesn’t seem to get it, you just have to tell him — not so fucking deep!

Next, you two need to quit feeling responsible for each other’s orgasms. This is the most important trick to good sex. Neither of you should ever be “on some obnoxious mission” to make the other cum.

He thinks he’s being chivalrous when he says stupid shit like, “if you won’t cum, there’s no reason I should.” Call him out. It’s not gentlemanly. It’s passive-aggressive and childish.

You have to sit him down and tell him. Tell him. Make sure he understands. He is responsible for his orgasm. You are responsible for your orgasm. Most importantly, neither of you is obligated to have an orgasm.

I have a feeling that sports metaphors will work for him, so tell him that sex is not a sport with a half-time and a scoreboard. There are no points. There is no goal. No one is keeping track of statistics.

Sex can last five minutes or five hours. You can each have multiple orgasms or none at all. It doesn’t matter.

I promise, once he stops competitive porno fucking, your love life will improve instantly.

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Advice

On yet another shallow cunt.

I was in the top 15% of my highschool class. Now I’m in my 5th semester of college in NYC, have a mere 27 credits, and haven’t been to class since I turned 21. I’m constantly wallowing in existential angst, terribly unmotivated to grow up and get a normal job, and an inch too short to be a model. I’m thinking of just becoming a secretary, dressing provocatively then suing my boss for sexual harassment. Or maybe just becoming a house-wife. [fuck feminism, give me an allowance and a list of shit to get done before you get home…I get shallow marriage proposals every time I go out] Or maybe I’ll join the peace corps. What say you Dear Coke Talk?

best,
shallow, and self-depricating

Yeah, life sucks when you’re beautiful in the big city.

You deserve an ass kicking — not just for being a shallow cunt, but also for completely missing the point. Fuck feminism? You don’t even know what the word means.

Screw the peace corps. Go enlist in the army.

Also, don’t ever brag about being in the top 15%.

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Advice

On getting out of the closet.

Ok here goes, I cheat on my wife with random hook ups with men. I usually just get blown. I fucked a guy twice. I just do it for the release since I get nothing at home.
Your thoughts?

Listen up, Congressman. Stop cheating on your wife with anonymous dudes. It’s super creepy.

If you’re trapped in a loveless marriage, get the fuck out — in this case even if you have kids. You’ll do more psychological damage to your offspring as a self-hating closeted homosexual than you will as an openly gay divorcee.

Also, stop voting Republican.

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