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September 11, 2007

Hi, my name's [name]. Want to have dinner?

Last month, I received this query:

I've had some fun with dating sites this year and moved onto trying to pick people up in the real world. Had successs on the two times I've tried - once was a friend of a friend of a friend in a pub and once picking up someone behind the counter of a shop.

In both of these, I had a the chance to make chit chat before I asked them
out. Easy and fun!

For my next amazing trick, I want to try meeting people who I only see for
milliseconds at a time - waiting for the lifts or in busy coffee shop. Hard
places to strike up any kind of conversation.

Do you think this is too direct:

Hi, can you tell me what your name is?
Uh, huh. My name is XXX. Are you a scary lawyer?
Thought so. Would you like to have lunch/dinner with me?

Or better to try and create some chat first?

I would love to have something insightful and brilliant to say, but I really don't. Mostly, I think this is a great idea, and I'm certainly getting a kick out of thinking about it!

Pros: It's playful, fun, lighthearted, and you don't end up spending a lot of time or effort on any given attempt before taking the dive and seeing if it goes to a date-like event.

Cons: It's pretty much a snap-decision sort of issue, so your personality (assuming you have one! which you seem to) doesn't have a chance to shine. I'm guessing that you're reasonably good-looking, though, if you're considering this sort of approach, and that will obviously help. Good grooming and a confident carriage also, obviously, are key here.

I'm guessing you'll get turned down a fair amount, but I wouldn't be surprised to hear that women took you up on this more often than one might expect on first blush. I definitely want to hear how this goes for you!

May 8, 2007

The 20 Year Old Virgin

More backlog in readers' questions:

To start with, I'm a 20 year old virgin. I've made a few postings on the CL CE section in my city over the last two months with little luck. I've tried posting ads that mentioned I was a virgin, and a couple that didn't. For the most part, I usually don't get any responses (from women, at least) which I suppose probably shouldn't surprise me, given the over 50 to 1 ratio of men and women.

Oh, boy.

Okay, so, CE is great. And it's especially great for people who have unusual predilictions, interests, leanings. And it's not inconceivable that someone who has an interest in virgins would be looking there. But it's not likely. And it's especially not likely that the person looking for virgins will be a woman.

Here's the thing: Our culture has a weird hard-on for female virginity. There are plenty of stories about the deflowering of this woman or that one, and the whole bloody sheet ritual that could be, for all I know, myth and legend, but it's still part of our zeitgeist. Firsts are always a big deal, but few firsts are built up to the same impressive, overblown status as the first time a particular pussy meets a cock. Especially if that cock already has a few miles on it and knows what it's doing. In the mythos of our sexual culture, the man should know what he's doing, and he should share his sexual prowess with the inexperienced young woman.

This puts young, inexperienced men at a distinct disadvantage. While not all women demand that their lovers know what they're doing, most do, and few want to deal with what they may perceive as a training exercise. After all, many of us have had to lead even experienced lovers to the promised land. Why would we want to start from scratch?

Now, don't tell me all the good reasons there are for taking a young lover who I could get started with before he has any bad habits. I know there are good reasons to do so, but I also know there are good reasons to avoid it, and, ultimately, the thrill of the first doesn't get me over the hump. And I think that's likely to be true for other women, too.

On another note, as you may imagine, I'm not particularly one to romanticize sex, but I probably wouldn't suggest a casual encounter for one's first sexual experience, either. I have plenty of friends who had that experience, and they liked it, and they're all healthy and happy now, so I certainly wouldn't say my take on this is the only good way to do it, but I'm glad for myself that my first sexual experiences were with people I was dating.

If you're convinced that you want to lose your virginity through the facilitation of the internet, I suggest that you not advertise it as such. Don't lie and make like you know all there is to know about sex, because, frankly, you're sure to embarrass yourself. I don't know how, but it'll happen. I won't tell you the stories of the things I look back on from my early days having sex that make me cringe. Let's move on.

The thing about virginity is that it seems like a burden when you have it, but we pretty much all get rid of it eventually, so don't sweat it too much. Get out there, have fun, and the sex with come in good time. Probably once you've given up feeling desperate and settled for feeling resigned.

April 24, 2007

Wait, how's that work, again? Nonmonogamy as an option

I have a bit of a backlog of questions from readers, which I'll try to work through in the next couple of weeks.

I read something on your blog that leads me to believe that you don’t like cheating, yet apparently you have main squeeze and you sleep around. Do you consider that cheating or do you have another definition? This is all new to me since I was married and monogamous forever, but I am not interested in going back to that. Soooo how do you have a main squeeze, and still fool around without someone getting hurt?

You're right; I don't like cheating. In general, I find it foreign and questionable. I understand that there are lots of situations where cheating is the lesser of the available evils, but I have a hard time understanding how people end up in situations where that's the case. Honesty is important to me (though I'm not fanatical about it), and I prefer to involve myself with people who are living basically up-front lives. Furthermore, I am continually baffled at cheating people's openness with strangers about their status while being deceptive with the person who is, in theory, the person they've chosen to spend their lives with. But, hey, I'm also baffled at people's fascination with American Idol, so, big deal.

What do I do? I do have a regular lover and I do sleep around. My lover knows I sleep around, and if we were more serious, I would tell him about all of my hookups. As it is, I just tell him about the extra fun or interesting ones. And if he asked, I'd tell him about the less spectacular ones, too; it's just not normally important to bring up. What is important is that he knows that I have hookups and that a) I'll talk about them sometimes and b) he can ask whatever he wants or needs to know. Meanwhile, he has other lovers, too, and people he's dating more seriously than he's dating me. I know about them and they know about me. In fact, I met him through his longest-term partner, with whom I'm very good friends.

Is your head spinning? Then you've probably never heard the term "polyamory", though that's not a term I particularly care for. Still, if you do a web search on it, you'll find more web pages full of people spouting on about how to do it right or wrong or best or worst than you'll know what to do with. Some of these might be useful. I haven't done such a search recently, so I have no idea what the state of information is at the moment.

Personally, I prefer the term nonmonogamy, and I describe my variant of it as consensual nonmonogamy. I keep people informed, and I expect they'll do the same. Those might be additionally useful search terms for you to consider. I bet they'll lead you to a variety of useful and useless places, but with any luck, you'll find something good.

I'm not going to go into more detail about this stuff, because I find it largely boring to talk about, but before I sign off, I do want to say one thing, and that is that I don't think it's possible to have relationships without someone getting hurt from time to time. More important than pussyfooting or tiptoeing around hoping never to cause pain is being clear and honest and communicating effectively with the people you're involved with. And when pain results, then it's your big chance to be thoughtful and considerate in dealing with it. This is true in any kind of ongoing relationship, whether sexual/romantic, familial or friendly. We can't avoid hurting people close to us, though I hope we avoid doing so on purpose; what we can avoid is being an asshole after we've caused pain. Ignoring or avoiding addressing the unintentional hurts we cause strikes me as vastly more problematic and flawed than causing them in the first place.

February 28, 2007

Kissing and asking

I'm going to get a bunch of details wrong in this post, I bet, because I'm too lazy to verify my memory, and that's not the main point, anyway. Following up on my last post, on first kisses and asking permission:

Back in the mid 90s, Antioch University (I think) decided to deal with a problem they were having with date rape and sexual harassment on campus by making a rule that a person had to verbally ask his or her partner's permission before taking a makeout session to the next level. There was a big stink about this on college campuses everywhere (or maybe just mine) and in a variety of newspapers. Absurd! they decried. How unreasonable!

Well, it did strike me as stiff, but after thinking about it a bit, I realized that it could actually be incredibly sexy to have a partner ask, if he did it in a creative way. No eye rolling or heavy sighing, but if he did it with a twinkle, so that it was an anticipatory rush, or a tease. He could ask permission to take off my shirt, and then not do it, leaving the potential to blossom in my mind. I could ask if I could slip my hand into his pants and watch his eyes react to the idea...

And that's when it occurred to me that asking permission to kiss someone could be entirely sexy. There are the other classic ways of making a first move, and they have a lot going for them, but in a setting where you want to be sure not to make an unwanted advance, and you think there is a not unreasonable chance of misreading signals, I go with the explicit question every time. And it's not even a fall-back. Try it; you'll like it!

February 21, 2007

Kiss me, baby!

I just got my first email from down under, if I read things right! This fellow is newly single after a long time:

So now I am exploring the world of casual loving and am loving going on dates, meeting new people and all the excitement. I've had some great experiences, have come across a problem I've never faced before at the age of 33 - first kisses. Just about all my relationships/shags involved me be seduced rather than the other way around as is usual. Now I have to start making the first move! ... I can sometimes tell when the right time is when the girl is giving me all the well-known body language signs, lots of eye contact and we are generally having a good time. No problem there.

But there are other times, I think when the girl is more reserved that I'm not sure...

So what are some amusing/fun/disarming ways a bloke can go in for the first kiss?

I love this question, and not just because I was fantasizing about kissing on my drive home tonight. Kissing is really great, and it gets short shrift in the world of casual sex; people are often rushing ahead to the main event, missing a lot of great scenery along the way.

I think I'd like to address this question in the course of multiple posts, because there are so many great ways to make a move, and I'd love to hear from readers on both sides of the first kiss (kisser and kissee, if it went down with someone initiating, or kissers both, if it was entirely mutual). What are first kisses that have gone well? What are moves you wouldn't make again if someone paid you? What's a trick that didn't go smoothly but worked out anyway?

But first, let me tell you a first kiss story that has come up several times recently, and that is a very fond memory:

There's this boy. He's super cute, and at the time this story takes place, I'd known him socially for a handful of years, but only peripherally. Around this time, I was getting to know him and his wife better, and we all ended up at a sex party together, where he and I spent some time chatting about a variety of things, including how weird it can be to be at a sex party where it's kind of unclear what your role as an observer is... but that's neither here nor there.

So we're chatting, and partway through the conversation, I was struck absolutely stupid by the desire to kiss him. He was still talking and, apparently, I was, too, though I really don't know what either of us said, because all I could think about was kissing him, and here we were surrounded by people in various states of undress and somehow, I was not in the middle of kissing him, and that was causing me all kinds of consternation.

But, a real problem here is that I'm shy. Oh, sure, I flirt like nobody's business, but when it comes to making a move, I'm about as smooth as a thirteen year old boy. So, of course, I went with the classic route of hoping he'd kiss me. But it wasn't working and thus, we still weren't kissing.

Well, this went on for an embarrassingly long time, until his wife came collect him for bed for the evening. Seeing my moment escaping from me, I decided to leap, and before I tell you what I did, I want to say that in retrospect, I think this is a classy approach that I would recommend to anyone:

We were wrapping up the conversation (I still don't know what we were talking about at that point) and I looked him in the eye and said, "Would you mind if I kissed you?"

He made an eyebrows-raised surprised face and then said, "No, I'd like that!" So we did, and it was awesome. Contrarily, I'm still shy to initiate with him (though, actually, that might add a little bit of fun to our flirtation), but I've had a hell of a lot of fun kissing him from time to time, and I look forward to doing it more in the future.

(Full disclosure: After I told this story to his wife, recently, she then passed it on to him, and he came back to me and said, "But hadn't we kissed the year before at that other party?" And, I'm embarrassed to say he's entirely right, so this isn't actually a first kiss story, but it acts like one, so I'm just adding this addendum onto it, even though it makes me look silly for forgetting the first first time I'd kissed him!)

November 29, 2006

Sex, love, and (non)monogamy

Last night, I went on about nonmonogamy, but I didn't really talk about the last part of my reader's question: "How have the social constructs of sex and love impacted you, or your partners, if at all?"

To some degree, this entire blog is a response to this question. Social constructs of sex and love are so massively overlapping that it took me a very long time to separate them in my emotional landscape, and I was lucky enough to grow up in a liberated setting where it was never implied that you can only have sex with someone you love. Still, as we all know, there are a lot of social equations that influence how we think and act without realizing it, and our culture certainly has managed to conflate sex and love.

For a long time, it was easier for me to believe that one could feel love for multiple people than that one could lust after more than one person at a time. Now, is that the most ridiculous thing you've ever heard? Come on, there's so much evidence for people desiring multiple others simultaneously, both looking around my immediate environment and looking at media examples, both fictional and non. Where did that idea come from? I blame the ether.

The ideas about sex and love that I find most appealingly countered in nonomongamy center around possession and agency. In a traditional monogamous pairing, partners more or less belong to each other. The degree to which a partnership plays this out varies significantly, of course. For example, my cousin has been dating an incredibly possessive fellow for several years. He gets twitchy when she goes out with male friends, and he insists that if she dresses up and looks hot that she's trying to make him jealous (and, it appears, succeeding.) What she gets out of this clingy form of love, I have no fucking clue, but, then, I obviously prefer a freer version of commitment.

Even when I think I might like to be able to have more say over who my partner spends time with, I'm glad I've chosen a relational style that doesn't allow me to do so, because I don't actually want to be possessive, and this makes me look closely at those urges when I have them. And it also means that I have largely dismantled the idea that love and exclusivity prove each other. I'm sure there are ways to break out of the ownership frame while conducting a healthy monogamous relationship, but since I haven't done that, I don't know what those ways are. Any of y'all who have? Pipe up!

November 28, 2006

Playing with nonmonogamy

I came across a post or two in the archives where you mentioned the logistics of casual sex in tension with a committed relationship. This caught my eye since I've been dealing with that very issue a lot lately. I've been in a serious relationship with my girlfriend coming up on four years now. I'm nearly 22, and we've moved in together after years of commuting between nearby cities. Recently, we realized that we had never done much of anything, sexually, with other people. Were we missing out on anything? Were there vast secrets of sex which were entirely lost to our naive conceptions? With these considerations in mind, we decided to give one another leave to mess around with other people, because hey, we're open-minded and "hip," right? So that's been working out moderately well, we've explored a bit and learned things and had fun. Trouble is, we both seem to sometimes get the predictable instances of nagging jealousy. I know each of us, when hooking up with another person, is fully aware that it's in no way serious, emotionally - but as a third party to the transaction, it can be difficult conceiving of that hookup occurring, and what it means to one's own lingering competitiveness and possessiveness.

I was wondering whether you had had any similar experiences, perhaps in the early stages of your ... casual sexperiment, as it were. Have you ever run up against these issues, or was it always an easy thing - I'm unattached, sex is fun, I'll go have some? How have the social constructs of sex and love impacted you, or your partners, if at all?

I love this set of questions, but, wow, what a can of worms! Fortunately, I'm not writing for a newspaper, so I can go on as long as I want, or until Law & Order distracts me too much.

First, you won't be surprised to hear that I think it's great that you've decided to check out what else is out there in the world of sexual experiences. A partnership based on affirmative choice is necessarily stronger than the same partnership chosen by default. Not to mention that there is something to be learned, technique-wise, from a variety of partners. For example, I learned to do this thing with my tongue recently that my past lovers will never get to enjoy. But I digress!

I hope, though, that you're not doing this because it's hip. Is nonmonogamy hip? I don't even know. There are plenty of good reasons to play with it, but that's not one of them. But you're a smart guy, so you know that, already.

Jealousy? This is obviously par for the course. As a rule, when I have a regular partner, I don't have any trouble with the partners they have in place when I enter the scene, but I frequently struggle with people who come on board after I do. If I could apply logic to my feelings, I would be able to say that the more clear my partner's commitment to me is, the less insecure I feel when my partner finds someone new. Unfortunately, this isn't the case, so I'm not going to tell you that since you and your girlfriend have a solid relationship and clear communication, this shouldn't be an issue for you. Are there ways to eliminate jealousy? If there are, I haven't found them.

I'm least likely to feel jealousy in very light relationships, obviously. The less invested I am, the less it matters if my lover has other things going, because I don't feel possessive of my time with him or my place in his life. I'm most likely to feel jealousy in a longer-term relationship that wants spicing up that I can't do, because that's something I can't do. I hate things I can't do for someone I love a lot.

Things that help me include talking to my partner and getting reassurance from him that he wants to be with me. That might mean spending extra time together or simply being sure that the time we spend together really "counts" (that is, doing whatever makes me or us feel connected, whether that's sex or reading to each other or working on house projects or walking in the woods or what-have-you.) This can be a good time to check our relationship for lazy spots (Do we spend a lot of our time together both of us IMing with other friends? Are we in a rut that's not taking us anywhere interesting?) and reaffirm our choice in being together. Or it might just be a time to have him hold my hand (or for me to hold his) and say, "Yes, this thing we're choosing to do is hard sometimes."

It may be useful to identify the details of what's happening. Rather than, "I'm jealous when you're out with him," you might examine more closely what's going on. Are you hanging out at home alone while she's out having fun? Do you spend a lot of time mooning over your new lover? What, specifically, gives you pause? I often find that focusing on the little things helps me work through my difficult feelings. After all, I'm not insecure about the big stuff, so even though jealousy feels big, it's often simply a reaction to small things.

There are a lot of things I love about being nonmonogamous, and I could go on and on about it, but far be it from me to suggest that it's the right thing for everyone, and jealousy is one of those things that just about everyone runs up against. That doesn't mean you're doing anything wrong, and the main thing I can suggest for dealing with it is to communicate clearly about what's happening.

Tomorrow, I'll talk about sex and love and how that relates to nonmonogamy for me.

November 8, 2006

Flirting with waitresses

Well, then! I will certainly give someone a blowjob in celebration of the hopeful turn of yesterday's election. But first, I need to have some anal sex to mark my specific celebration with regards to Mr. Santorum of PA. (For those of you who don't understand the link, click here.

But I now return to my regular night job of dispensing opinions, advice and all-out snarking:

While in a local bar the other night I found myself flirting with my waitress. She seemed to welcome it - lingering at my table, holding conversation beyond "what do you want to drink next", etc. What suprised me was that she actually made physical contact with me - touched my shoulder when asking if I needed another beer, and leaned up against me lightly to point me in the direction of the bathrooms.

So I have two questions: one, was this a sign that I should have left her my phone number (I didn't, though I left a nice tip), and two, is trying to pick up your waitress extra-gauche?

I'll start by saying I've never waited tables, so I could totally blow this one. I encourage any women who have direct experience here to weigh in.

But! Yes, you should have left her your phone number. If you ask me (and you did), it's never gauche to pick up a woman who's clearly flirting with you. (Okay, that's not true if it's, say, your best friend's fiance the night before the wedding and she's really drunk and they haven't talked about it first, but let's consider most reasonable examples, here, shall we?) As long as you, personally, are not skeevy (and if you are, she's probably not flirting with you), you're in good shape. Also, leaving your phone number is extremely low-key as come-ons go.

In fact, my first thought here is that, well, of course you should leave your number! But because women are often used to being the pursued rather than taking the initiative, if you actually want something to happen, you might do better to ask for her number. But, really, if she's flirting that much, she ought to be able to pick up the damn phone herself, right?

So, now I have an assignment for you: go back to the bar, flirt with her, leave your number, and report back, 'k?

November 1, 2006

How do I handle my partner's problems? With care.

Today, I address a question from a reader, which I got ages ago and just rediscovered:

Should a guy just listen, or try to solve the his girl's problems?

My friends joke about "male answer syndrome," which is what happens when they talk to their boyfriends about a problem and the boyfriend immediately starts offering solutions, even if they're just looking to vent.

I've seen this pattern repeat itself irrespective of gender, though, so let's broaden out the question a bit. This isn't just a matter of how a guy should be with his girlfriend's problems, but how people, in general, can be helpful to each other.

First, if you have a problem, you can help yourself by being clear on whether you're looking for sympathy or suggestions. I'm often looking for sympathy and rarely for suggestions, personally, and I can save myself the aggravation of unwanted advice if I start the conversation with, "I just need to vent." That way, I figure I'm perfectly justified in biting the head off the imprudent person who tries to tell me what to do!

But many people don't do that. So, say you have a lover who's talking about an issue. What should you do? I suggest a clarifying question: "Are you looking for ideas or advice, or just a listening ear?" That's really the only way to know what the right approach is. Save this question for later, too, because the answer will be different in future conversations, as well.

Sadly, there is no one-size-fits-all answer. If only life were so easy. Of course, then I'd be complaining about it being dull.

August 29, 2006

Why is sex so important?

I recently received this query:

Why is sex so important in your life? I mean I of course understand people want to have fun and I'm not at all against it, but I think smoking pot while listening to good music, or drinking half a bottle of tequila while listening to rock music, or jacking off while looking at pictures and videos of your favourite kind of perversion on the internet is a lot better than usual sex, because, in these cases, you don't have to adapt to the wishes of somebody else and make him/her adapt to yours, but you can just do everything as you like. So, why?

I'm having a "same planet, different worlds" problem trying to think about how to answer this question. Maybe it's because I've never smoked pot? I have drunk half a bottle of tequila, though, and I like sex more, so maybe it's just a different experience of the same sorts of things.

It's true that playing by myself is pretty great, and it means I can do whatever I want to myself, within my abilities, and I would never, ever give up masturbation, but neither would I give up partner sex. In some ways, these two things are so different that it wouldn't even occur to me to compare them. It's like the difference between hanging out at home with a video vs. going to a party. I'm unlikely to do both in the same evening, but my life just wouldn't be complete without a bit of each, and some other stuff, too.

But, then, I've been accused of being a bit of a variety junky.

Still, why is sex important to me? For some of the very reasons that you seem to think it sucks: I like adaptingg to someone else's desires, and I like having others adapt to my desires. Having sex with someone else brings a totally different kind of energy into the bedroom (or living room, or kitchen, or...) [Note to roommates: Don't worry, I put a towel down on the couch, first.] Getting myself off is completely different from fucking, or sucking cock, and no matter how good I am with my fingers, having someone eat me out is a whole different thing, too. No matter how much I try, I can't give myself the same electric buzz of a lover's hand stroking down my back, and I don't care what kind of attachments they're selling for vibrators these days; there's nothing like having my lover fuck me from behind.

Even setting aside all of that, sex is great because it's an opportunity to connect with someone outside of myself. It's not a very popular attitude to have these days, but I really like people. I like the differences between them, and the similarities. I learn new things with every new person I meet, and the things I learn from new lovers are some of my favorites. I feel powerful when I'm having sex, and I feel vulnerable, exhilarated, protective and protected. I get a huge rush from sex with other people that is completely unlike the release I get from jilling off to porn on the internet.

I would no more trade sex for masturbation or alcohol (or vice versa) than I would trade people for books. For me, these are entirely orthogonal drives and desires.

August 28, 2006

Logistics of out-of-town hookups

I posted last month about the joys of the out of town hookup, and I received a couple of questions about that sort of arrangement.

First, how do I protect my valuables?

This, of course, is an issue at home, too, and I'll admit that I'm actually pretty lax about this. I don't tend to think of guys who are looking for casual sex as big into thievery, but, on the other hand, you never know, right? At home, I make sure that my valuables aren't sitting out in plain sight. I actually have to admit that my room is a little on the messy side, and I think that probably makes it harder for someone who might otherwise be inclined to take advantage of something sitting in plain sight to do so. Also, I rarely leave a guy alone anywhere in my house for more time than it takes me to run to the bathroom, and I wouldn't unless I knew him well enough to have an ongoing arrangement with him.

In a hotel, I'm probably better off, since most of the hotels where I stay have safes, and that's where I put my wallet and anything else valuable I might be carrying with me on that trip. I suppose a guy might run off with my business clothes, but it would be hard for me to get too upset about that!

The second question was how do I decide where to meet people when it's not my "home turf"?

It's true that when I'm at home, I know the neighborhoods and I know where I'll be safe at the time of day I'm meeting my potential hookup. I also know the cafes and bars that I like to visit, whereas, when I'm out of town, I'm going on someone else's say-so. As a rule, I like to use my hotel's bar or lounge, if it has one. This has two advantages: I don't have to venture out on the town in an unknown neighborhood, and if I like the guy, we can easily go up to my room.

There have been two times when this plan wouldn't work. Once, I was in a hotel with no lounge, and the other time, there was a very nice lounge, where many of my company's clients were enjoying an after-dinner drink. In both of these cases, I'm afraid I just lazy-ed out of the hookup. In the case of the hotel with no lounge, I'd already been in contact with a couple of potential guys before going to the hotel. Once I got there and saw that I'd have to find another option (and that my hotel was in an uninteresting business area), I decided I was more interested in watching reruns of Law & Order than trying to manage logistics, so I emailed my guys to say it wasn't going to work. In the case of the hotel with lots of clients, I knew that was going to be the case, and I simply chose not to make any hookup arrangements.

The truth is, I'm lazy, so if a hookup is going to be too much work, I'm unlikely to bother with it, especially for an out-of-towner.

August 22, 2006

What to wear!

One of my loyal readers wrote me this morning to ask,

I had an interesting first meeting w/a potential hookup recently that brought up a question for you. We were ogling each other over drinks and the topic of clothing choice for a hookup date came up.

Specifically, the question of how much skin to show. She preferred tight shirts that showed the definition of pecks (for men) and breasts (for herself). I tend to go with a button-up shirt that shows a little neck and like seeing ample cleavage on a woman (not that she necessarily needs to be well-endowed, even cleavage on small women works for me).

What are your preferences, for yourself and the men you "see"?

This is funny timing because just last night one of my lovers and I were talking about clothing and what's sexy. Some friends bought me a custom corset for my birthday, and almost everyone I know thinks I look particularly good in corsets, but he was saying that corsets leave him cold. Go figure.

The thing about clothing is that there are, as usual, several things happening. First, you obviously want to wear something that feels good, comfortable, flattering. And you want to wear something that's going to attract your (potential) lover. When your date is someone you don't know, though, you don't know what will be attractive to them! So, what to do? Fall back on what's attractive to you, of course.

This makes sense, and I think it's a good approach. Alternately, there's always the choice of wearing an outfit that nets lots of compliments.

Personally, I like to wear an outfit that looks good (to me), but, more importantly, that feels sexy. I'm pretty sure that when I feel sexy, I project sexy, and that's a good thing to do on a first date (and even better on a second date!) So, what am I likely to wear? In the summer, which is, I must say, way better for flirty attire, I'm fond of flippy skirts and a lacy camisole. This ends up showing a fair amount of skin and being rather clingy, at least on top. I also have a couple of fun little dresses that I like. And, depending on how I want/expect the date to go, I may or may not wear panties. But that might be another post.

As for my dates, I'm not sure I care a whole lot about what they wear. For a first date, I like to get the impression that he's put a little effort into his attire, but it's far from a deal-breaker if he hasn't. I mock men whose pants fall off their hips at the slightest provocation, but I like it when I find that my date's pants needs only the most gentle encouragement once we're in the bedroom. I love touchable fabrics, as they give me an excuse to put my hands on him. And I really like my date to look comfortable in whatever he's wearing. That sexy thong isn't doing you any good if you spend the whole evening squirming as a result of wearing it, after all.

July 13, 2006

Webcams: hot or not?

One of my readers recently emailed me with this query: "Have you ever had an internet sex experience using a webcam or otherwise? What do you think about them?"

I'll answer the easy part first: I'm a technological stick-in-the-mud, so I don't have a webcam. My laptop is 5 years old, and I think it would die a horrible death if I tried to make it do more than the basic web-browsing, music-listening and blogging that I currently do with it. I have watched other people's web cams, but since I'm not all that interested in watching guys jerk off if I don't even have the chance of (ahem) hands-on participation, it's a lot less interesting to me than it seems to be for the guys who like the chance to be an exhibitionist.

So, yes, I've had a sex experience using a webcam, if you count me having the webcam window running in the background while a guy jerked off, but it didn't do anything for me, so it didn't feel sexual to me.

As for what I think about webcams... well, I've had some fun with sapiophile's, but usually when she and I are getting frisky and teasing another friend of ours, but that's mostly interesting because we all already know each other and are just playing around. It's not, for me, particularly hot. But I certainly know women who enjoy it a lot.

For me, I'd rather be doing it in person, or playing more with my imagination, which means either phone sex, or the much maligned "cyber". The benefits of playing face-to-face are so obvious that I won't go into them. But why would I prefer phone or cyber sex to webcamming? Well, what if I'm feeling cranky and out-of-sorts and don't feel like putting on a show? Or what if I want to think about doing something that's too logistically complicated to actually act out? Or what if I want to ... well, pretty much everything I'm looking for in a sexual exchange that's not in person involves my imagination, which works best if it's not distracted by having to watch someone or think about how I look while I jill off. Or, um, whatever.

So, no, I don't have much interest in webcams, but I'd actually be interested to hear from folks who like them a lot, because maybe I'm just missing something because of lack of experience or exposure.

June 21, 2006

The big O or a big dud?

This morning, I received a query on a topic that's often on my mind:

Dear ClueChick,

I've run into an interesting issue of late and I'd love your thoughts. The last two women I've met for casual encounters had the interesting issue of being unable to have an orgasm when having sex with a stranger (i.e., me). They assured me it wasn't my performance that caused the lack of orgasm, just a general issue with all new guys they sleep with. Despite this, they continue to have and enjoy casual encounters.

How important is the orgasm to the casual encounter? Do you experience one the first time you're rolling around with someone new?

Now, I could go on and on in my response, here, but I'll try not to bore you all too much. First, of course, each person places a different level of importance on the orgasm as part of the sexual experience, whether casual or otherwise. I happen not to place a lot of importance on it, because I almost never get off when I'm with a partner, casual or committed, but I still enjoy sex quite a lot (obviously). For someone for whom orgasm is less of a hurdle, I suspect that the big O plays a more important role in the whole experience.

So, no, I don't come the first time I'm fucking a new person, and probably not the next several times, either, because it takes me a while to get comfortable enough with someone to be able to talk about the details of my complicated relationship to orgasm. To say it's a loaded topic would be both an intentional pun and an understatement. I've never wanted to turn my sexual experiences into a possibly-fruitless quest for an orgasm when I enjoy the whole shebang uncomplicatedly without.

That said, I always like it when I'm with a lover who cares about my pleasure. This can be a tricky topic, itself, because, of course, I like my lovers to give me the opening to say what I need, but I don't want them to be pushy about it if I say I'm not going to come. On the other hand, I imagine it must be frustrating for them. I imagine how I would feel if my lover never came, and I'll tell you, it would definitely make me doubt my mad skills in bed, so I've decided to go on a quest to get off with partners more often. The trick there, of course, is to find partners with whom I can explore this topic, touchy bits and all. Needless to say, this is not casual encounter fodder. That's another post, though.

All that said, I assure you that sex can be a hell of a lot of fun, even if there's no orgasm, and as long as you're giving your lovers a chance to tell you what would help them get off and are showing that you're interested in making that happen for them, you're doing what you can. Reaching orgasm in any encounter is a two-person interaction, and if your lovers say they just don't get there the first time(s) with someone new, they ought to know. With any luck, you'll get a chance to test the theory that it's just the getting-to-know-you factor.

June 14, 2006

To reject or to ignore: the dating woman's email dilemma

One of my female readers asks, "The men that have contacted me I'm not interested in. Am I obligated to respond or is it better to just ignore them?"

Ahh, the ongoing question of how to deal with men you're not interested in. This is always a struggle. On the one hand, you don't want to be a jerk and ignore them, but on the other hand, it's awkward to decline them, and ignoring them is less blatant and rude online.

I will admit that I often feel like I'm being rude when I don't respond to someone's approach in response to one of my ads or profiles, but that doesn't stop me from doing it, and I think that's okay (obviously). On those occasions when I've responded to say, "Thanks, but no, thanks," about a quarter of the time I don't hear back, a quarter of the time I get an appreciative response, and half the time I get the guy badgering me to give him a chance. Sometimes it feels worth it to me, and other times not, to take the trouble to respond, but I never feel obligated, and you shouldn't, either.

On the other hand, if a guy has obviously taken a lot of time to write a thoughtful and interesting email, I'm often pleased to be able to say, "Hey, I appreciate the effort you put into your email," even if I don't find him appealing. And, unsurprisingly, the guys who write the good emails are more likely to be the ones who respond positively when I decline.

June 11, 2006

On being emotionally available in relationships, casual and otherwise

A readers asks, "How much emotion should a guy show?"

As always, with this kind of question, I'd like to begin with the caveat that the answer depends on at least three factors: the guy, the person he's dating/fucking/whatevering, and their relationship.

First, the guy: How much emotion is it natural for you to show? I don't really buy the line that men are naturally less emotional than women, though I do see that men are given fewer socially-approved opportunities to show their emotions. I, for example, play my emotions relatively close to my chest. This means that when I'm in a new relationship, the person I'm seeing is unlikely to get to see a whole lot of what's happening under the surface. Furthermore, there are layers of what's happening. If I'm having a good time on a date, I can be happy and smiling and laughing, or I can choose to open up more and talk about how much I enjoy spending time with my date, or open up further still and talk about what I think that might mean for the future of our relationship. All of these are choices about how much emotion and/or internal life to share with a date. Only you know what's comfortable for you.

Second, the person you're dating: I've been on dates with guys who tell me too much too soon, and it's not pretty. I don't want to know about your depression support group on our first date, and I don't want to know that you feel so comfortable with me that you can tell me about your embarrassing thumb-sucking habit over coffee. I do like it when people are comfortable with me, but until I know you better, I don't have enough texture to my sense of you to be able to respond reasonably to early oversharing. This makes me feel awkward, and I hate feeling awkward. On the flip side, if we've been dating for a while and we're still having only superficial conversations about the weather, I'm going to think you're one of "those" guys who never makes room for a real connection, and I'm likely to write you off.

Third, the relationship: Are you casual fuckbuddies? In that case, even after a few months, your relationship isn't going to have the structure to allow for conversations that bare the soul. Just because I've sucked you off doesn't mean I want to hear about how your parents were never at your elementary school plays and how much that hurt you. On the other hand, if you have a relationship that's heading for more significant intimacy, whether friendly or romantic, it'll be weird for you to keep your partner at arm's length and never talk about the things that are on your mind, whether good or bad, whether related to your relationship or simply the day-to-day workings of your life.

Finally, the balance of what to share, in terms of your inner life, with a friend or a lover, is one that many people make unconsciously, and that often works well. Conscious awareness of some of the factors that play into this never hurts, though, right? In general, people take turns opening up and seeing how the other person responds. If I share more about myself and the person I'm talking to doesn't get all weird about it, and then, in turn, opens himself as the conversation continues, we can continue to deepen the intimacy/personal-ness of the conversation until someone takes a step that the other person isn't willing to match. Then you stop there, and either try again to deepen the intimacy at a later date, or the relationship stays at that level. (To be clear: staying at a given level, as long as both people are happy/content there, is a great thing.) Over time, friendships and romantic relationships shift around, sometimes being more and sometimes less intimate. In new relationships, however, you're still working out where your baseline level of shared comfort is. It's up to you, when your partner makes an intimacy-overture, whether you want to meet her or not. And pay attention to whether she meets yours.

Finally, beware of rushing into intimacy before your relationship has the structures to back it up. My one blazingly bad idea of a fling was a case of both of us diving head first into the emotional intensity of the potential of our connection without checking whether our lives could actually fit the shape of the thing together. In the end, we couldn't, and the dramatic backlash of that has fucked up the potential for some steamingly hot sex ever since.

June 8, 2006

Deal breakers in early flirtations with guys I meet online

A while back, I asked people to ask me things they'd be curious to know about, and Lil wrote wondering about deal breakers in serious and casual relationships. I'll start with talking about deal breakers even before I get to the relationship stage.

There are a few:

I won't fuck guys who are cheating on someone in order to fuck me. It makes me feel yucky and I don't like it. (Yucky is obviously very different from naughty, which is hot.)

I don't do guys who smoke (cigarettes).

I won't even talk about sex with a guy who gives me a hard time about condom use.

It won't get as far as talking about condoms if a guy can't write coherently and in a way that doesn't make me feel like he thinks I'm an object for his pleasure and convenience rather than a person with wants, opinions and interests of my own.

No doubt I could come up with some others, but those are the bare bones ones that leap to mind when I think about the hurdles a guy has to pass before I'll take him seriously as a prospect.

June 1, 2006

What's the best casual sex: fuckbuddies, one night stands, or something else?

While I was away, B asked, in response to styles of casual sex, whether I have a preference of what style of casual sex to have.

I do, in fact.

I find one night stands tiresome. Because I expect some email exchange before arranging to meet someone, and then a non-sex meet-up first, before even getting around to the fun part, one-offs are a lot of work for not much payoff. Also, although I know some people really get off on the first time with someone new, I find that I have more fun in subsequent encounters. As I get to know a lover better, I relax more, and we become more comfortable with each other, not to mention moving into fun fantasy territory.

I enjoy the light, ongoing thing, where whenever we're both available and horny, we can make plans and have some fun. This is the epitome of no strings attached, for me, because it's very fluid, but by getting together regularly, a light relationship does form, which provides a platform for more adventurous exploration.

These days, however, my favorite is the friends with benefits style arrangement. Here, the sex may be casual but the relationship isn't, and depending on how you set things up, you may arrange playdates ahead of time, or just play it by ear like with the looser arrangement I described above. Mainly what I like about this is the opportunity to plan ahead, which, since my life is pretty full, helps me be sure to make time for sex (I know, it's kind of sad that I have to plan ahead for it, right?) in any given week.

In fact, recently, my sex drive is high enough that I'm considering actually picking up a regular old boyfriend so I can plan on having sex on an even more regular and frequent basis. But that's a whole different post :)

What about you all, readers? Do you have favorite formats of casual (or otherwise) sex?

May 29, 2006

No, still no pictures here, sorry.

In response to sapiophile's well thought-out post on picking up hot fat chicks, DJ commented, "Hi ClueChick. Why not post a pic on here so we can see how beautiful you really are?"

I don't post a pic for several reasons:

First, I like to be anonymous. I don't need my parents surfing their way here and finding a big picture of me attached to a long story about how I fucked that hot guy I met on the internet. Furthermore, I don't need my future employers doing a web search on me and finding the same. And that's not even getting into the messy can of worms I'd prefer to avoid with people who know me in real life thinking that just because I write a blog about casual sex means that I'd love to fuck them casually and whenever they like. A funny little secret about me is that I'm actually quite picky and (don't tell anyone) kinda shy.

Second, I already get lots of offers from my readers to let them take me out for drinks or the like. I didn't set up this blog as a way to meet people, and I think a picture would confuse things.

And third, people could look at my picture and do one of two things: Either they'll see how gorgeous I am and decide they have to get in my pants, thereby ignoring my advice. Or they'll see how totally not gorgeous I am (hey, everyone's taste is different, right?) and decide that all my advice is sour grapes and thus not worth listening to.

My point in writing this blog is not to set myself up as some fabulous sex symbol, but just to be the voice of everywoman, or at least every-woman-who's-enjoying-casual-sex, and toss out some of my observations and advice in hopes of a) helping clueful men get laid and b) helping women who like casual sex have better options among the men.

As I've suggested in the past, if it would help you to picture what I look like, you should feel free to think of some woman you think is extraordinarily hot and imagine her writing this blog. Just for kicks, of course. Alternately, you can think of me as a fairly average woman: hotter than some, less hot than others, but who happens to write reasonably well, which is why you keep coming back to read my blog, right?

May 11, 2006

The key to casual sex

Sapiophile asks, "Does exchanging keys and reserving a drawer in one another's domiciles always mean it isn't casual anymore?"

Yes.

I'm tempted to leave it at that, but that's not much of a post, now, is it?

Casual relationships can take any number of forms, some of them more regular than others. In fact, though none of my casual relationships have involved trading more than phone numbers and saliva, I can imagine an ongoing-but-casual thing that would result in trading keys. In fact, that could facilitate the playing out of all kinds of fantasies, but that's another post.

But the point at which you're making room for each others' stuff in your homes, it's no longer casual. Sorry.

May 9, 2006

Everything I do for fun is kinky. How do I talk about that on the first date?

In a comment on yesterday's post, wotw asked,

This problem comes up repeatedly. It's a first date. We hardly know each other. She asks: "So what do you do for fun?". The honest answer is: "Stick weird foreign objects up women, set people on fire, host (with invaluable help from invaluable friends) large get-togethers for sexually open people, etc."

I do usually get around to telling them about this stuff, usually on about, oh, the second or third date or so. But the first five minutes of the first date seems a little soon.

On the one hand, this stuff takes up a lot of my time, and crowds out a lot of other things I might do for fun---so if I don't mention this, I'm sort of at a loss for an answer. I end up saying someting really stupid like "Oh, you know, I like all kinds of stuff."

Or I say something like "I read a lot", which is moderately accurate (actually, "I buy a lot of books" is more accurate), at least as a matter of fact, but grossly inaccurate, I think, as far as conveying information about my funloving nature.

Help me, Cluechick! How do I answer this question?

This is a great question. There are lots of kinky people online, as we all know, but there are also lots of people who aren't kinky. And there's a time that it's reasonable to talk about your kinks and darker desires, but the first few minutes of conversation are rarely that time.

So, I recommend that you lie.

Okay, wait, no, sorry, I didn't mean that. But it doesn't hurt to have a few innocuous things that you can talk about in those first minutes before you get into some of the more, ah, extreme interests. While I'm a strong proponent of honesty in general, I'm also in favor of the occasional white lie to help people save face or to keep a new social situation flowing smoothly. This is probably one of those times.

Your approach of talking about books is a good one. Other fairly innocuous topics might be movies or current events (though that gets dangerously close to politics, which might also be best avoided), travel, or what have you. Now, innocuous topics will not, in fact, help immensely in conveying your fun-loving nature, as you put it, but they will help to break the ice, let you and your date get comfortable with each other, and come to feel comfortable enough that you can broach the topic of the last weird object you inserted in a woman. (That reminds me of a fellow I fondly called Insertibles Guy, but that's another story.)

Remember, in the first few minutes of talking to someone, you're not necessarily trying to convey every last tidbit of information about yourself, but rather, are just getting started on striking up a rapport.

There is, of course, another hand to this answer, however: If you would not be interested in dating/playing with/fucking this woman if she's not into the sorts of things that you're into, then you have very little to lose in scaring her away early. If she's into the sort of play that you are, she's probably not going to be nonplussed by your opening the conversation in that vein. I, for example, have been known to enjoy a variety of activities that might not be found on the regular menu, and I'm generally pleased when someone I'm flirting with lays out his interests early so we can see what overlap we have.

On the other other hand, you never know what she might be interested in trying after getting to know you and how fabulously attracted she is to you.

All of this is to say, then, that you have two basic options, both reasonable: Start on innocuous topics (which you will probably want to think about ahead of time), or dive right in. I recommend that you use your judgement on which to use based on the balance between how disappointed you will be if you don't get to stick weird objects in her because you've scared her away and how disappointed you will be if you get invested and then find out you won't get to stick weird objects in her.

May 6, 2006

How many people are out there enjoying casual sex, anyway?

The other day I posted wondering what questions you all might have, or topics you'd like to see me post on. I had a few responses, all interesting. Today, I'll address b4f's question:

How much casual sex do you think is actually going on out there? Is it a select few folks like us who choose to spend their nights pawing and sniffing each other or is the world essentially one giant pick-up bar with a few prudish naysayers on the sidelines?

The truth is, I don't have any good idea about this, because I spend almost all of my time safely ensconced in the cozy and, yes, sexually free environs of my home and neighborhood. Here, even those people who aren't engaging in casual sex either have in the past, or take a rather laissez faire attitude toward it, which makes it seem normal to me. I understand that in vast swaths of the country, and even in other social circles in my very city, this isn't the case.

So, although I may perceive that there are lots of people running out and having as much casual fun as their hearts may desire, I think the truth is that we're probably a rather select few.

Looking at Craig's List for a bit of insight here, there are many hundreds of posts each from people in my city alone. And they're all looking for casual sex. Now, sure, there's a lot of repetition, but you also have to assume that not everyone is looking there. And then, of course, there's the bar scene.

So, I think there's a lot of casual sex happening. Probably most of it is happening in younger crowds; I'm 30, and by this time, most people are settled or settling down. And probably most of it is happening as a filler, rather than as a life-oriented practice. But not all of it! I know there are plenty of people of all ages who enjoy casual encounters and have no desire to change that. I just don't have any idea how many there are!

I do, though, think that we are the few... the proud... the, um... well, I don't know what our title is, but we're out there!

May 2, 2006

Casual sex and insecurity

Dear CC, Why does casual sex make me insecure? Signed, Hot But Insecure:

Dear Hot But Insecure:
First, casual sex IS less secure that committed sex. After all, sex in a r'ship has a structure and clear expectations and boundaries. When you're dating someone, there's a generally accepted path and unspoken rules that most people follow. Casual sex, on the other hand, is fluid and doesn't have much in the way of rules. So, while, when dating, you can reasonably expect your lover to maintain regular contact, be it a phone call the next morning or an email touching base midweek, in the casual sex setting, you can reasonably expect your lover to either call you in the morning or not, to let you know what he's doing later that week, or not, etc. That's unsettling, and it leaves the niggling gremlins of your imagination to go to work.

And what do those niggling gremlins focus on? The natural insecurities that everyone has, of course. In this case, they probably make you think things like, "He hasn't returned my email in 12 hours. That must mean he never wants to talk to me again! And the reason he never wants to talk to me again is that I'm unattractive and boring and I give horrible head! This means I'm a bad person, and I'll never find anyone to date, or even fuck, ever again!

Pay no attention to the gremlins in the corner. The insecurity is normal, and if it drives you to distraction, you may decide casual sex isn't for you. Or it may mean that in your casual engagements, you need to set up systems or understandings that clarify the process for you and help you avoid those insecurities. And, of course, doing what you can to allay your own fears is important. Remember, you're awesome. Make a totally immodest list of all the awesome things about you. Ask your friends to help. I don't know if that'll help with the insecurity, but it sounds like a fun project, doesn't it?

Best, CC

April 25, 2006

The weirdest thing

Yesterday, I got an email, perhaps inspired by Sunday's post asking, "What's the weirdest thing one of your people has asked you to do?"

Before I answer this question, I want to make a general statement:

People, be careful what you ask me, because I'm basically an open book, here, and some of you aren't going to like what you read.

So you should only keep reading if you're really sure you want to know the weirdest thing (by my lights) that a lover has asked me to do since the commencement of my little fling with casual sex.

Okay, you're still reading, so I'll tell you: About six months ago, there was a guy who presented as basically normal, and who was generally fun in bed, when we got to that. But he really took me by surprise when, mid-fuck, he asked me to spit in his mouth. I mean, I know people get off on all kinds of things, and intellectually, I get the appeal of the spitting thing, but in practice? It's not so much my thing. Of course, as the spitter, it's pretty low-impact; it would've been different if he'd wanted me to be the spittee. Needless to say, though I found his request weird, it was also easy to accommodate.

I'm sure some of the other things I've been asked to do would rate higher on some people's weird scales, but that one definitely took the cake for me.

April 19, 2006

Cuddle up while you can, before summer makes it too sweaty for touching!

The other day, this query appeared in my inbox:

How cuddly should a guy be?

I have to tell you, I don't really know how to answer this kind of question, because the answer depends so much on the individual you're with. Really, the best way to find out how cuddly you should be is to ask your partner. Or act as cuddly as you like, and if she finds it excessive, she'll probably take some of her space back. Or if it's not enough, you'll find her touching you more.

Speaking for myself, I tend to be a little less on the cuddly side than many. I like to touch, but I don't like to be entwined or tangled for more than a few minutes. I like spooning, but I far prefer to be on the outside 99% of the time. I love friendly touch: stroking his arm or back or standing close enough that our shoulders touch. I also like to receive that kind of touch.

So, now you know what to do if you ever get me into bed. But, really, if you're sleeping with someone else (which I assume you are, since you're not sleeping with me), I suggest you ask her what she likes!

March 23, 2006

What do you disclose about your relationship network, and when?

I'm a bi poly woman who likes to have casual things with strangers a couple of times a year. My steadies are fine with this, and I always follow the rules, like condoms and stuff. But I'm never sure should I tell the people I'm picking up about my other partners, or does it even matter?

I love this question., in part because I'm really not sure about the answer! But I'll take a stab at it, anyway.

The good news is that I think you're in the right either way. Barring objections from your partners, you can tell your fuckbuddies whatever you like: You're following the rules you've agreed upon, and it may or may not be relevant to share that those are rules you have with another person. After all, you may be using condoms in part because you've agreed with your partners to do so, but I certainly hope you'd be using them even if you were otherwise single!

An advantage to telling your flings about your other partners is that if you have rules that are more strict or unusual than "the norm" (whatever that is), it's an easy excuse/reason. "Why do you have to use latex gloves to touch my dick?" says he. You can say, "My boyfriend's only okay with it if I use gloves. You choose." I can't imagine a guy on CL who'd turn down a gloved hand in favor of no hand.

A disadvantage to telling, though, is that you may then find yourself explaining that, no, it really is okay with your boyfriend, and, yes, that's how you do things, etc. Some people love to talk about their relationship structures, and others find it tiresome. That's totally up to you.

Obviously, the main drawback to not mentioning it is that if your fling turns into something more serious, you have to find the time to bring it up, and, personally, I think there's no good time after fucking to say, "Oh, by the way, I have this person I've been seeing for a few years..."

I'd be curious to hear what other nonmonogamous readers do on this one.

March 22, 2006

Why haven't you dated a black guy?

My post on race generated a flurry of responses, in comments and in my inbox, and I'd like to address the primary question that a couple of people asked me: Why do I think I haven't dated a black guy?

I suspect I'm not the best person to answer this question, but I'm not going to call my therapist for her insight, so you'll have to make do with my self-analysis. I have, of course, received responses from black men to various posts on CL, and to a couple of my profiles on dating sites, and there have been some instances where I was interested enough to email back, and, a handful of times, to meet up, but it's never gone beyond the coffee date. Why not?

First, and possibly most impossibly lame: I feel a certain amount of embarrassment about my theoretical interest in black guys, and this makes me distrust my evaluation of the attractiveness of any particular black guy I meet, because, gosh, is he actually hot, or am I just in love with the idea of fucking a black guy? I mean, I think about it, and I imagine how my pale hand would look touching his dark shoulder, or my tongue on his nipple, or my mouth on his... well, you get the idea. I'm not comfortable being hot for an idea and projecting that onto an actual person, even if the person in question wouldn't actually mind, and, needless to say, I've never actually brought it up in a conversation with one of my potentials (though a reasonable argument could be made that I ought to!)

Second, I know I'm racist. (And you are, too. If you think you can be free of racism in this society, you're fooling yourself.) And I worry about how that might play out in a relationship, even a light one, with a black man! When I spend time with a black guy in a setting with a lot of potential, I feel shy, that I might say the wrong thing (more than usual; despite the blog, I'm not actually all that smooth) or do something silly, or just generally prove what everyone already knows: I'm a white girl who mostly hangs out with white folks.

I'd like to get over these hangups, and I like to think that I will, eventually, but I hate to think about dragging some poor guy along with me for the ride. And that's the main reason I've yet to date or fuck a black guy.

March 15, 2006

What about the boy looking for a threesome? (MMW, that is)

On Monday, I wrote about couples looking for men for threesomes, and in response, I received this query:

What if i'm a guy and I want to find another guy and a girl to hook up with? What's the best way to find other people who are into this?

Well, first off, you probably won't have trouble finding a man, because, well, as I've previously remarked, there are lots of men out there looking to play. The trick, with regards to picking up men for your purposes, may be in finding a guy who wants to play with men and women. Straight guys don't want to get in bed with boys, and gay dudes shudder at the thought of getting naked with a girl. So, you have to find that rare type: the bisexual. Or the heteroflexible, which may be more likely. Or the gay boy who isn't skeeved by tits. In general, I find that people have a hard time with that gray area in the middle, and especially men are caught in this bind.

(Side note: if you think that only women are hurt by "the patriarchy", think long and hard about just how inflexible and limiting images of male sexuality are in popular culture. If liberation means that we all get to live in ways that honestly reflect our inner selves and desires, then it's clear that men have a long road ahead of them before they're able to break free of rigid images of the manly man ideal.)

As for finding a woman, of course, you know this is going to be a challenge. Because women are fewer and farther between in the casual scene to begin with, and then, on top of that, you're looking for a woman who's open to something that's slightly off the norm. But I'll tell you a cheery little secret: lots of women fantasize about getting with two guys. And lots of the women who are already inclined to go looking for casual encounters are probably the types who are sexually open enough that they're the sort who just might be interested in some hot boy on boy on girl (or boy on girl on boy, or girl on boy on boy, or... well, you get the idea) action. So, in fact, simply by looking for this sort of thing, you're setting a "hook" in your ad that is likely to help you in your search.

I would recommend that you try posting several variations of your ad. You may find that this works best in a couple of steps: first meet one, then together look for the third. Or, you may find that you meet up with people who like the idea of getting with a totally new combination of people. You never know. But, oddly, I'm more optimistic about your chances than those of a regular guy looking for a straight-up boy-girl thing. I definitely want to hear back from you on how it goes!

March 13, 2006

For couples looking for hookups with men

I know this is a little off topic for you, but I'm married, my wife and I like to have threesomes, but mostly with other men. I'm bi, but our guys don't have to be... whatever works is good! Even though there are lots of men looking for hookups out there, we sometimes have trouble finding the real deal. Any tips?

Gosh, I have to admit, there's part of me that's shocked to hear that you're having trouble picking up men. I mean, sure, as a couple picking up men, you're limiting your field a bit in comparison to say, my field, which is pretty wide open, but even so, there are an awful lot of men out there, many of whom are open to somewhat, ah, unusual experiences and encounters.

That said, on the other hand, a lot of guys are pretty freaked out at the idea of getting naked with another man, even if there's no suggestion that there might be contact between them. Because of the all-or-nothing view of homosexuality, especially male homosexuality, even a whiff of comfort with other men in a sexual context can strike fear into the hearts of many. Lame? Absolutely. But real? Yes, that, too.

I suggest that you alternate between mentioning your bisexuality and not mentioning it, in different ads. In my experience, picking up men for MMW play, those men who are interested in a bisexual sort of encounter will mention it on their own, even if they've never done anything like that before. If not, then on those occasions that you don't raise bisexual play as a possibility, you shouldn't mention it, either. If, in fact, you're happy with either type of encounter, you can cast a wider net by not pushing that fear button.

On the other hand, part of me wonders how much fun it really would be to have an encounter with someone who might flip out to know the rest of the story. Sometimes, patience is a better bet.

February 13, 2006

Married men and the online scene

One of the very most common questions I get is from men who are in a (closed) marriage or relationship and wan