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What Guys Really Think When a Woman Has Sex on the First Date

September 23, 2014

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Advice from three of our guy friends. This week they answer the following: “Does sleeping with a guy on a first date really ruin my chances for a future relationship with him? What if it’s obvious we really like each other, the chemistry’s great, we have a lot in common, and we’re both horny?”

Straight Married Guy (Figleaf): I don’t think first-date sex together ruins your chances but it does change them.  You know the critical little “voice in your ear” that says, “Hold off: good girls shouldn’t ruin their ‘reputations,’” even when you’d rather not wait?  Men get that too.  Only ours says “Go for it now: losers never get another chance.” Neither “voice” is telling the truth but they can have an effect anyway.  Sometimes when we have sex right away the social pressure those “voices” represent get in the way of everything else we might feel about each other. So for both men and women I think it’s worth it to wait at least for the rest of your feelings catch up. And since when did horny have a shelf-life anyway?  Even waiting a few days (three days, not three dates) gives you both time to talk, a chance to take showers and sleep on it in your own beds, a time to decide what you really want instead of what you think you should do, and… time to get your respective bedrooms tidy and kitchens stocked for intimate guests.

Gay Single Guy (Daniel): Thinking that putting out on the first date will kill off any romantic possibilities is pandering to an old skool way of thinking about sex and love: that the guy must court, wait a gazillion years while the woman’s heart oh so steadily burns and yearns and he tries to satisfy himself on a nightly basis, Onan-style, until they are finally wedded before sex can even be in the equation. In the 21st century, sex on the first date could very well just mean that you “have a lot in common and were both horny.” Sex doesn’t always complicate, nor is it always a barrier to further emotional intimacy. On the contrary, in fact. Consider all the gay couples around the world who meet each other on a sex date/Internet hook-up/anonymous sex excursion, find that there are other things they like about each other and end up happily part of a pair years later. What really ruins future relationships is being dishonest about your needs and desires. So fuck on the first date if you like! Any guy who would dismiss you for it despite having such a great connection otherwise is too much of a fool to keep on seeing anyway.

Straight Single Guy (Mark): I don’t think there are too many absolutes in this crazy game of love, so a first-date romp doesn’t necessarily preclude any future relationship potential. What is a universal absolute regarding potential relationships is that communication is key (trite as it sounds, it’s so true). Let’s say you and your date are lucky enough to totally “connect” in all the ways mentioned above, and are also comfortable enough to acknowledge to each other how much you are on the same page, even about getting physical right away (and of course, as Em & Lo have taught us, keeping in mind, and also communicating about, all the relevant important safety issues involved!). Well, in a way, you already have some fantastic “They were inseparable (figuratively in this case, heh) from the moment they met!” romantic potential built right in!  So why, then, does the fun have to stop at the bedroom doorway? Now, as we know, it’s not always such an ideal world, with perfect communication right off the bat, so exercising a modicum of restraint (and building up anticipation for the fun after a subsequent date soon to follow) isn’t the worst thing in the world, either. So go with the flow.

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Our “guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Gay Guy is one-time stripper and sex columnist Daniel; our Straight Married Guy is Figleaf, the guy behind RealAdultSex.com; and our Straight Single Guy is Mark Luczak, a tech god at Carnegie Mellon University (he was single when we first asked him this question, but he is now married!). To ask the guys your own question, click here.



How to Convince Two (Straight) Guys to Have a Threeway

September 16, 2014

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Advice from three of our guy friends. This week a straight woman asks, “How can I can convince two hetero dudes to have a threeway with me?”

Straight Married Guy (Ben): What you really need to do is figure out if the MMF threeway is a “Yes,” a “No,” or a “Maybe” for these guys. Yes? No problem — go for it. No? it’s never going to happen – stop wasting your time. Maybe? Well, then it’s negotiable. And, while it’s easiest just to come out and ask, you can also test the waters by sharing “a sexy dream you had,” or confessing a fantasy after a few drinks. Truth or Dare can be a good gateway game to finding out who’s a “Maybe.”

The “Maybes” are the ones that need convincing, and what that really means is setting some ground rules. Maybe it’s no guy/guy touching. Maybe it’s lots of touching but no kissing. Maybe it’s only one cock visible at a time. Whatever. If it’s a “Maybe” for your guy, the question becomes, “What do you need to make this threesome happen?” And that is a question that can be answered.

Straight Single Guy (Max): Barring the possibility that you could trick these “hetero” dudes into your lair (using beer, snacks or Ahnold movies) I’d say that your best bet is to try and wiggle your way into the arms of two friends or, even better, the bromance. Face it: a lot of guys go by the super homophobic rule of “as long as the balls don’t touch,” so you’re much better off finding two guys that are as comfortable with one another’s body as they are with their joint egos. After that, your best policy is honesty. You can’t be coy about getting two guys at the same time, so I’d say be up front: “If you boys want me, you’re going to have to share. I’ll be in that room. Come find me?” Oh, and please end any threeway with a lot of high fives. They’re free, and you deserve it.

Gay Committed Guy (Mark):

1. Get them drunk.
2. If that doesn’t work, you’re on your own. And when you find out, let me know.
3. “Dudes”?

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Our “wise guys” are a rotating group of contributors. This week’s Straight Married Guy is Ben, a writer and artist living in Los Angeles. Our Committed Gay Guy, Mark, is a writer and teacher in NYC, and our Single Straight Guy, Max, is a recent college grad in New England. To ask the guys your own question, click here.



Do Guys Really Care If Their Girlfriend Has a Higher Body Count?

September 9, 2014

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photo via flickr

Advice from three of our guy friends. This week they answer the following: Does the average hetero guy really care if his girlfriend/wife has had sex with more people than he has? And if so, why?

Straight Married Guy (Jamie): I may be somewhat in the minority here in that, while I have an extremely liberal philosophy about sex, I haven’t had a particularly high number of sexual partners (I was always a “girlfriend guy” and just didn’t rack up the big numbers).  I’ve also never bought into the whole men-as-players/women-as-sluts double standard.  Many of the female friends I admire most have had lots of sexual partners, but are also all well-adjusted, independent women.  To be honest, I’ve always been more attracted to women who have an air of worldliness.  I think it’s a turn-on to be with a woman who is confident sexually and knows what she likes.  And if that confidence came at the hands (or whatever) of more former lovers then I’ve had, well that’s just fine by me.

Gay Engaged Guy (Joel Derfner, author of Swish): As a gay man living in a major metropolitan city, I’ve lost track of the amount of sex I’ve had.  How then can I hold a partner to a different standard?  I recommend that everybody have enough sex so that both the boy and the girl can honestly say, “I’m not really sure,” and leave it at that.  That said, I asked my straight cousin, whose wife has always been very sexually free, and he said that his biggest worry had been that their kids’ attitude toward sex would develop far too early as a result, but this has turned out not to be the case.  I loathe children, so I’m going to stick with the “I’m not really sure” recommendation.

Straight Single Guy (L.A. Chris): Totally. He also cares if she’s stronger, smarter, or wealthier than he is. It comes down to our primal need for dominance. Unless a guy’s got a fetish or extreme dominance in one of those areas (i.e., a body-builder won’t care about a girl’s bulging biceps), it’s a turn-off to be second banana or subordinate. Truth be told, he’ll also feel a little bit jealous (it’s a big competition between guys since we were teenagers). And lastly, we want our girl to be a virgin slut, and we need to pretend that if we’re not the first, then at least we’re the best.

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Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Gay Engaged Guy is Joel Derfner, author of SwishTo ask the guys your own question, click here.



Why You Should Lie When He Asks About His Penis Size

August 26, 2014

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Advice from three of our guy friends. This week they answer the following: If a guy asks me how I think his penis ranks size-wise, and I honestly think it’s a little on the small side or perhaps too skinny, what do you think the best approach is?

Straight Married Guy (Fred): I’ll start answering this question with another question:  If I honestly think a woman is on the big side or perhaps a little chubby and she asks me if she’s fat, what do you think the best approach is? Of course I tell her that she looks great. But there’s a difference between these two situations: she can eat a healthier diet and exercise but he can’t do anything about his size. She may even be looking for a little motivation with the question, but it’s still polite to fib in this instance. Which means it’s imperative to fib in the other instance. Tell him that you think his size is great. You can add that you’ve seen bigger and, more importantly, you’ve seen smaller, and that he’s just right.  Adding that too big can be uncomfortable is always a good tidbit as well.  Being honest in this case will only serve to make him forever self-conscious or even more self-conscious than he already is (men hear all the time that “It’s not the size of the boat but the motion of the ocean,” but men also see the widening eyes and devilish smiles when women talk about sizable, girthy man-sausage). A finessed answer can give him the confidence that most women find attractive and will more than make up for his tiny dick.

Straight Single Guy (Chris): This is an easy one: Lie. If you tell the truth (“It’s kind of too skinny…”) his penis may never again work for you, ever. Put yourself in his shoes, “Are my boobs big enough for you? You seem to always look at girls with big boobs when they walk by…” Would you really want him to say “Well, honey, your boobs are cute, but they are much smaller than I prefer. If I could use magic to change you, I would give you natural 34DD’s.” So lie. But before you do, you need to know is that if his penis is small-ish, he already knows. He is already sensitive about it, and he is just hoping you haven’t been with any well-endowed men. So if you overcompensate with an outright fabrication such as, “It’s huge. It’s the biggest one I’ve ever seen,” he will know you are lying to spare his feelings and he will feel even worse. So just say, “Honestly, it’s not the biggest one I’ve ever seen, but it works great for me and you are fantastic in bed. Let’s do it right now!” Trust me, this is the only answer that can work.
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Why He Didn’t Call or Text When He Said He Would

August 19, 2014

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Advice from three of our guy friends. This week they answer the following: Why didn’t he call  (or text/email/Gchat/et al) when he said he would?

Straight Married Guy (Matt): There’s a simple answer to this one: it doesn’t matter. Most women I know get very worked up over this, and it never helps anything. It could be one of ten thousand possible reasons, and there is no chance that sitting and discussing it with your friends ad infinitum or stressing about it is going to help anything. It might just be some reason that has nothing to do with you (family problem, work problem, some other unrelated problem), or hey, maybe he likes you and he scared off the last woman he liked, so he’s forcing himself to pull back a little — or maybe your worst fear is true, and he isn’t actually into you.

You won’t figure any of this out by sitting there and worrying about it or analyzing every tidbit of your last conversation or email exchange looking for clues, so what’s the point? My advice is to do everything possible not to obsess over the guy’s delay in calling. Distract yourself with whatever you can, even a date or flirtation with someone else if that’s what it takes. And if he never calls back, fuck him. At least you can feel good about not having wasted all that time sitting by your phone.

Straight Single Guy (Colin): Let’s be optimistic for a moment. Maybe he was debating how long he should wait to call so that he wouldn’t seem desperate. But now he’s waited too long and feels silly calling so long after the fact. Okay now let’s be realistic. Most likely this guy fell into the trap we all do sometimes, saying what we think we should say instead of what we actually think. Maybe the sparks weren’t there and he didn’t have the heart to tell you. Try to get in touch with him if you can. But if he’s still flakey, give him a quick kick to the curb and move on.

Gay Committed Guy (Terence): While tempted to say, “He’s just not that…” I think not calling is more likely because the alcohol has worn off and/or another woman is already on the side. When a guy wants to get laid, and let’s face it, if he’s asking for your number, then he’s that kind of into you, the first question running through his head after getting your number is why didn’t we just go home then? Calling sets up a whole ‘nother time-consuming process that sometimes just doesn’t seem worth it.

Personally, I think not calling takes real balls — not the good ones. Either you’re an over-confident prick, or you’ve got a girlfriend. You’re over-confident thinking you can get someone better (easier), or you know you may get a little somethin’ started and then have to emergency bail out of the situation. Solution: always, always take his number even though it’s just as shitty to wait around for him to return your calls.

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Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week they’re all a little shy.



Wise Guys: Do Men Ever Appreciate a Handjob?

August 12, 2014

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photo via flickr

Advice from four of our guy friends. This week they answer the following: I’ve heard that it’s not worth giving a guy a handjob because he can just do it better himself. Is that true?

Straight Married Guy (Jamie): Sadly, yes.  But I think the problem is just one of misconception on the part of most women.  In my opinion many women think, perhaps due to their lovers’ penchant for hard and fast intercourse, that a handjob needs to be a vigorous yank-a-thon.  Ladies, please, you’re not trying to inflate a bicycle tire here!  Despite popular opinion, the penis is a very sensitive organ.  And, with improper handling, and without lubrication, it can chafe.  The truth is, we’re just really good at it all by ourselves. Don’t get me wrong, we love it when you touch us and we appreciate the thought but, beyond a little foreplay grabby-grab, leave the heavy lifting to the professionals.

Straight Single Guy (Chris): The handjob is the single most underrated and underused sexual skill in the mix. I suppose it’s a self-fulfilling prophesy, that guys don’t like handjobs because they are generally bad, and girls don’t give them because guys don’t like them, so they never get any better at them. Well, I for one protest. A good, thorough, properly lubed, and sufficiently practiced handjob can be an amazing and deeply fulfilling sexual experience.

Let me be somewhat specific while trying not to be too crude. First of all, you have a range of options of position and technique, grip, pressure, lubricant, and speed. In my opinion, far more than with any other “technique.” You have significantly more control, drawing out the orgasm and the, how shall I put it, location of completion? All of the best blowjobs involve significant participation of the hands, so why would anyone believe the hands aren’t a good option on their own?

Please, please ignore the naysayers and their, “If I wanted a handjob, I’d give it to myself.” Practice, practice, practice, and cultivate this skill. Feel free to practice on me if you need to…

Just please consider the following:

1. Never, ever, ever do it dry, under any circumstances.

2. Consider aiming at yourself (anywhere, but some places are better than others) rather than at our belly buttons.

3. Try from behind and underneath. Trust me.

4. Control it. Bring it to the edge and back again. And again.

5. Don’t forget the surrounding area.

Straight Single Guy #2 (Joe): Absolutely, unequivocally, 100% NOT TRUE!  Any guy would much rather have a handjob from you than from himself. First of all, guys do it by themselves ALL the time, so having you do it makes it a special treat. Imagine running your fingers lightly over your own skin: it feels nice.  Now imagine someone you are attracted to doing it.  Much better, eh?  The physical act might be identical, but having someone else’s body heat / touch / scent / sounds / smile there and then not knowing exactly what they’re going to do adds so much more to it.

Gay Married Guy (Jon Ross): Nothing could be further from the truth, because there is nothing better than having someone do your work for you. While it’s true that guys can technically give themselves better handjobs than anyone else, it’s the thought — and effort — that counts. Gay guys don’t have a huge advantage over women here either: while having a dick does give you some insight into what works and what doesn’t, every guy is different and what blows my load may not get my man off. Personally I like a nice handjob to lead to a great blowjob, but if that’s not in the cards for whatever reason, a good handjob is wonderfully satisfying.

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Our “guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Straight Married Guy is Jamie, a film editor in NY, our Straight Single Guy #1 is Chris DiClerico, and our Gay Married Guy is Jon Ross. To ask the guys your own question, click here.



Wise Guys: Why Do Men Like Strip Clubs?

August 5, 2014

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photo via Flickr

Advice from three of our guy friends. This week they answer the following: Why are some guys so into strip clubs? Do most guys buy into the fantasy that the stripper is actually enjoying herself — or don’t they care?

Straight Single Guy (Colin): Lots of guys aren’t into strip clubs. Probably more are kind of weirded out by them than you might think. For the ones who do enjoy an outing to the nearest nudie bar, it’s usually about the visual overload of the body parts we fantasize about all day long. Finally we can be praised for overtly staring at a woman’s breasts. We might imagine what women around us look like naked and a strip club is an opportunity to live the dream. It’s fun to pretend the stripper is enjoying herself, and some are at some times, but in the end it’s just pretending and most of us probably know — like a twelve your old who still plays into his parents leaving milk and cookies out for Santa Claus.

Gay Married Guy (Joel Derfner, author of Lawfully Wedded Husband): I’m not sure I’m really in a position to answer this, because I’ve worked as a stripper, and I kind of loved it. This is one way in which it’s much easier to be a gay man than a straight man:  you don’t have to worry that you’re objectifying female sex workers.

That said: I think the fantasy that the stripper is enjoying herself is exactly what makes strip clubs so exciting. Your average Joe is not the kind of guy at whom a gorgeous, scantily clad woman is likely to hurl herself. He’s just not attractive enough, or manly enough, or sexy enough, or powerful enough, or whatever enough. But the moment he walks into a strip club, gorgeous, scantily clad women start hurling themselves at him — a thing that couldn’t happen unless he were incredibly attractive, manly, sexy, powerful, and whatever. In a way the excitement isn’t about the woman in front of him at all; it’s about how she allows him to see himself.

Stripping has its own psychological rewards, by the way, at least for men who do it; these too come from how it allows the stripper to see himself. I have to imagine that stripping offers at least some of the same rewards to women who do it.

Straight Married Guy (Matt): Guys are into strip clubs because it’s not only visual stimulation, but it also changes the dynamic of who’s pursuing whom. In any strip club you’ll see the fattest, baldest middle-aged guy there being approached by women, each one asking if he wants a lap dance, with him waving off busty 19-year-old after busty 19-year-old, not giving most of them the time of day. Sure, most guys like seeing naked women, plain and simple, but it’s the flipping of the power dynamic that creates the strip club “regular” — the guy who gets blown off the most out in the real world and gets off on turning girls down (as well as having a 19-year-old ass grinding his package when he eventually gives one of them the nod).

Do we believe that the strippers are enjoying themselves? I think it’s a suspension of disbelief while you’re on the premises. So no, most guys who are inside the strip club don’t care in that moment if the strippers are enjoying themselves, and don’t allow themselves to think about it too much, or they’d lose their erections and head for the door.

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Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Gay Engaged Guy is Joel Derfner, author of Swish.To ask the guys your own question, click here.



Wise Guys: Which Would You Choose, Intercourse or Oral?

July 22, 2014

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apples_orangesphoto via flickr

Advice from three of our guy friends. This week they answer the following: “If guys had to choose between only intercourse or only blowjobs for the rest of their life, which do you think most guys would choose?”

Straight Single Guy (L.A. Chris): I think most guys would choose blowjobs, but they really should be choosing intercourse. BJs are the best thing to happen to sex since sliced bread, but with added perks (let’s just say it’s like taking your car in for an oil change and getting a free car wash). Most men don’t get as many blowjobs in their daily routine as they’d like, so the prospect of guaranteed hummers for life is a dream come true. But it’s a devil’s bargain. Blowjobs are awesome, but they’re unsubstantial — mere icing on the cake. And a man can’t feel truly satisfied on a diet of sugar frosting alone. At some point he’s going to want to connect meaningfully with his partner. And by the time he gets to be 30 or 40 he may even want to have a baby. (Yes, men have biological clocks too. Ours are not as prominent as women’s, they’re more like pocket watches, but we have them.)

Straight Married Guy (Fred): I think most guys would struggle with this one, but then decide that intercourse would be the better choice. There are more variations of intercourse, for one thing.  There’s more skin contact which is always nice. Giving her pleasure at the same time is a big turn on.  The fact that intercourse is active rather than passive makes it a more likely choice for guys.  We like to do stuff… like aggressive pelvic thrusting.

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Wise Guys: What Do Men Think About When They Masturbate?

July 8, 2014

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photo via flickr

Advice from three of our guy friends. A while back, one woman wanted to know “Why do men masturbate in relationships, even when the sex is good and regular?” In his response, Max (one of our Single Straight Guys) said, “Trust me: You don’t want to do the things that we’re thinking about when masturbating.” So we wanted to know “What DO guys think about when they masturbate?” Ironically, of all three guys’ answers to this follow-up question, it’s Max’s that we thought was the most tame:

Straight Single Guy (Max): In order to masturbate, I have to have some kind of scenario in my head. It can be past experiences, girls that I’ve been with and (perhaps most often) girls that I want to be with. It might be the girl that was making eyes at me earlier in the day (though the likelihood is that I was making eyes at her and just misinterpreting her look of “what are you staring at?”) or perhaps stranger subjects, such as fictional girls from dreams, co-workers, or women that you might consider out of your age range but still attractive (there’s a reason that MILF is a household word).

Oftentimes, the male mind is most interested in the forbidden. For instance, the girlfriend that wouldn’t try anal? It’s only going to happen in your head. Already have a girlfriend but have the hots for her friends? Save everyone the heartache. You really want to break into your workplace late at night and pour champagne all over each other and do it on your boss’s desk? You won’t get arrested if it’s just a dream. Bisexual fantasies? Go for it. Essentially, I view masturbation as a time for completely uncensored fantasy. Whatever comes to mind and turns me on, I go with it. And as far as girls’ fantasies go? I’m amazed when I talk to my girl friends and they all say that they don’t think about much of anything… just concentrating. Weird.

Gay Committed Guy (Mark): As a very private person who sticks to a fairly small collection of gay vanilla porn for solo gratification, the specifics of this one are probably out of my league.  Fantasies are boundless and infinitely various — that’s sort of the point, right? — regardless of whether one is a man or a woman.  (Although I’d like to ask Max, a.k.a. “you don’t want to know” what could be so bad.  Violence?  Unsanctioned excrement?  Pets?) That said, some educated guesses as to what some straight guys might be thinking of while wanking:

1) Women who are not their wives/girlfriends.

2) Their wives/girlfriends doing really degrading stuff (see above).

3) Men.

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Wise Guys: Do Men Ever Turn Down Casual Sex?

July 1, 2014

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Advice from three of our guy friends. This week they answer the following: Do guys ever turn down casual sex? To ask the guys your own question, click here.

Straight Married Guy (Jamie): My own experience with casual sex is a bit limited.  I was always a “girlfriend guy” and it was only between relationships that I occasionally had the chance to get freaky with someone I wasn’t dating.  I’m sure there are plenty of reasons why a guy might choose to go home to his Xbox over a no-strings-attached BJ, but in my case it was almost always because the girl was way too drunk.  Call me old-fashioned, but there’s just nothing sexy to me about that slack-jawed, half-lidded stare from some girl in a bar who spills most of her drink wobbling over to you to invite you home.  The couple of times I did go home with someone who was far less than sober, the sex was always overly urgent and awkward and (shocker!) I usually regretted it.

Straight Single Guy (Chris): Yes guys do, contrary to popular belief, turn down casual sex on occasion. The number one reason given, “That bitch was crazy!” It’s really simple. Guys love casual sex when it is actually casual. If the chances of the girl going sideways and stalking, calling every day thereafter, or crying hysterically is too high, the risk to reward ratio is simply not good enough to take the chance. In all likelihood, any guy who is trolling for casual sex has a handful of booty-call numbers in his phone anyway, and isn’t scared to use them.

Gay Married Guy (Jon Ross): Gay guys turning down casual sex is like Tara Reid turning down a drink, but it does happen from time to time. The reasons can include just about anything from “I’m too drunk” to “you’re too ugly,” to “I’m going shopping with my mom,” but I find the most common reason guys turn down casual sex is because they’re in or starting a more serious relationship. And straight guys? I don’t think they’re any different from gay guys in this respect (except for, perhaps, the shopping thing). To a lesser extent, guys abstain from doing it no-strings to avoid passing on any temporary if nasty bugs. Gotta be clean!

Our “guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Gay Married Guy is Jon Ross and our Straight Single Guy is Chris DiClerico. To ask the guys your own question, click here.

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