I've been getting a lot of questions about having a threesome. Mainly, how does a guy go about getting one? Ah, yes, the threesome. A huge fantasy for all guys. No doubt I'm being asked because I had a threesome with twins, which is the ultimate guy fantasy.

Personally, I have no interest in threesomes anymore. Or even one-night stands. Of course, if you've read my book God is a Woman: Dating Disasters you already know all this.

Women wonder "What's the big deal? Why would you want to be with two women at the same time?" There are two butts, four breasts, four legs... it's simply a matter of math. Why not three women, then? Or four? Please, are you trying to kill us? We're not machines! (In other words, we would if we could.)

Truthfully, there seems to be an innate desire in men to experience a variety of types of women. We have an insatiable desire to know what a blonde looks like naked versus a brunette. We wonder if a redhead's hair is the same color in all places. Naturally, the idea of experiencing and taking in visual comparisons on the spot is especially appealing.

In the end, a threesome is not that big a deal and not as fulfilling as a good relationship with the right woman. Of course, no guy out there is going to buy that until he experiences a threesome himself. Some things you just have to experience for yourself to believe.

My first threesome was with cousins (not mine, you idiot). My second was with twins. I screwed up a chance to have a threesome with sisters and passed on the chance to have one with a girlfriend and her best friend. Notice a pattern?

Like most guys, I always thought women would have to be strangers to be involved in a threesome, which is perhaps why I couldn't have one, previously. It wasn't until I worked with a comedian who had been a disco DJ in the 70's that it was explained to me. He once had been with three ex-girlfriends all together on his birthday. When he shared the story and that all three girls were tight friends, I told him mine and that I was surprised that the women were all tight in these threesomes.

"Oh yeah, absolutely. In a threesome it's the women who are tight. They feel safe and really want to experience a lot and share with their best friend. They can talk about it later, analyze it, and know exactly what the other is discussing without her having to describe the situation. You're just the dick to ride, no more than an amusement park ride. I'll take it, though. It's not so bad, huh? Yeah, you'll never have a threesome unless the two women are really close. In fact, they've probably talked about having one. You're the stranger because they don't want any other friends to know about it and they don't want guys they know to start to expect it or to bug them about being in one. So it won't be with their boyfriends, either."
 
Hearing this and looking back, I realized the sisters who I screwed up a chance for a threesome with had set me up from the start. They had probably discussed having a threesome before and I was their mark. Unfortunately, I blew it.  

This is where most guys screw up: they try to have a threesome with women who are strangers. Odds are against it, unless both ladies just have sex all the time with whoever, whenever, and are probably druggies who aren't remotely attractive. The key to a threesome is to recognize when the ingredients are there and then to steer the conversation gently toward it. "You guys are really close. You mentioned threesomes. Have you ever had one?" Feel it out, see how they respond.

One woman I dated for a while got drunk one night while we were out and kept suggesting a threesome "with her hot friend with perfect breasts." Then she quickly backed down and refused to give me her friend's info to set it up (she and her friend had discussed it and apparently the friend was interested). It would not surprise me at all to learn that the two of them did have a threesome but with another guy who was a stranger. When it comes right down to it, women curious about threesomes really don't want to sexually share their boyfriends with close friends. This is understandable and if you want your relationship to continue, I advise against it. This is why I passed on the opportunity for a threesome with yet another girlfriend and her best friend.
 
If you really want to have a threesome, keep an eye out for women who are close. Give them both an equal amount of attention. Flirt big time. Are they both flirting back? Do they both appear equally interested in you? Steer the conversation in the direction of threesomes. See how they respond. If they don't squirm or become uncomfortable, discuss it a little further. Maybe ask who is a better kisser, or—better yet—if they, as close friends, discuss things like how to kiss, mentioning that guys don't discuss such things but you heard women do and were just curious. If they say yes, joke that you're willing to kiss them both to see if they have a similar technique. What else did they teach each other...?
 
Incidentally, one thing that can come out of a threesome is increased sexual awareness. While a woman you are sleeping with one-on-one is wary to give you tips, a second woman may be very willing to tell you to "try touching her there now" or "lift her up and down really fast right now!" I learned some really good things I never would have learned outside a threesome.

Be sure to pick up a copy of Ian’s bestselling book (not only because it’s full of good stuff, but also because I’m not paying him), God is a Woman: Dating Disasters.

And find excerpts and Ian's other columns here.