The Not-so-Straight Girl’s Guide to PIcking Up Chicks

I get a lot of requests from women wanting to know how to go about finding another woman to experiment with. This interest has been piqued, to a degree, by the advent of many celebrities coming out as bisexual (Megan Fox and Fergie, just recently, for example). There’ve been a handful of television shows with bisexual characters as well of late. And, too, there is a more generalized acceptance in society for same sex experimentation among women. This visibility has led to it becoming “safer” for women to admit that they’re interested, and to explore those interests in many cases.

If this is something you find yourself thinking a lot about, you can rest assured that you’re not weird or abnormal. In fact, according to Dr. Lisa Diamond, female sexuality is largely fluid and a great many women go through periods where they have a desire to experiment, arguing that for women, sexual attraction tends to be much more gender nonspecific than that of men. I know from my personal experiences that is true for me.

If you’ve been reading me for a while, you know that my in-depth exploration of Sapphic sex began very shortly after my first experience with Nikki. I seduced one of my closest girlfriends, and we in turn seduced our next two closest friends. For several weeks after that, we paired off in various combinations and enjoyed a great deal of sexual experimentation. Words just cannot convey how intense that period of time was for me.

Subsequent to that, I went on a binge, seducing eight more girls while I was in high school, and another 15 or so during my first year in college. It literally became sport fucking for me. And I won’t lie, it was a great deal of fun; I really enjoy seducing “straight” chicks.

Nowadays, I find myself able to pick up women with relative ease. Some of that, I’m sure, can be attributed to the fact that I am in San Francisco. Many people here just aren’t uptight about exploring their sexuality. It wasn’t too terribly difficult in Miami, either, nor was it in Tennessee (not coincidentally, the heart of the Bible Belt).

When I talk or write about my success, people invariably want to know how I do it, or what the secret is. I don’t know that there is a secret, per se. I suspect that the self confidence I project has something to do with it, combined with the fact that I don’t hide my sexuality. I project an aura of self-confidence that many people find alluring and am a huge flirt, especially with other women. And I have a pretty broad understanding of the psychology of human sexuality so I know what trips peoples’ triggers and how to elicit sexual reactions. So all of these things have kind of developed over the course of the past eight years or so to get me to the point I am today. Maybe I should take a hidden camera along with me the next time I go on the prowl? :lurk:

Or not. 😛

When I walk into a lesbian club, I’ll flirt and make certain sexual overtures that let everyone there know I am looking for someone to play with. With women, I extremely forward and even aggressive in some cases. I’m not that way at all with men – I tend to be put-offish and reserved. The reasons behind that have been discussed to varying degrees in other posts I’ve made here on SL. So I suspect that the true path to success has more to do with knowing what you’re doing and having the self confidence to carry it off.

Somewhere in all of this lies the answer.

Easier said than done, no?

If you do reach that point and you find yourself in a position to experiment with another woman, you’re in for a real treat. I posted an article some months ago about the differences between sex with a man vs. sex with a woman. While it may not be the easiest thing you’ve ever done, I can almost promise you once you’ve been there you’ll come away from the it with a much greater appreciation and understanding of your own sexuality, even if the experience itself is largely negative.

Many women are open to the idea

I have said it before and I’ll say it again: In my estimation, a good 80% of women would try a sexual encounter with another woman if they were put in the right set of circumstances. Your trick, of course, is A) to find a woman who’s open to the idea, B) get her into the right mindset, and C) take advantage of it.

One of the ironies of the sexual double standard in today’s society is that it is much more acceptable for girls to explore this side of their sexuality than it is for guys to do so. There is much less stigma associated with a woman exploring her lesbian side and this leads many women to seriously entertain the idea of finding another female to “play” with. (For the record, I don’t subscribe to that standard. In my opinion, guys exploring their bisexuality is just as valid, and exciting, as women doing it.)

So how do you go about doing finding someone to play with?

First Things First

Before you get started looking for someone, you are going to have to be comfortable being sexual and taking the lead in terms of trying to foment some type of relationship. For many women, they still see it as a “guy thing” to pursue a girl in order to hook up and whatnot. If you’re one who’s not averse to asking a guy out, or overtly flirting with a guy, making the first move, etc., then you will stand a better chance of success in your pursuit of a woman. However, if you’re not one who can be the pursuer or make the first move, you’re going to have some problems, generally speaking. Everyone gets lucky occasionally, so it may not be an issue for you. But in the long run, if you want to be successful, you’re going to need to get yourself into a mindset where you can be the one who’ takes the initiative and is doing the chasing.

Second Thing: Get over your fear of rejection!

This is the single biggest obstacle most first timers have to get past – the fear of making a move and being rejected.

Everyone gets rejected at some point, even those who lie and say they don’t! The trick is to realize this and not let it get you down. I make that sound easier than it is, I know, but the fact is you’re not going to develop the confidence you need until you understand and accept that.

I know you’ll be shocked, but even I’ve been rejected before, once very publicly. I asked a woman out while she was near a group of her friends (big, rookie mistake). ((Never ask a woman out in front of her freinds where she’s forced to deny her curiosity to save face)) When I asked her if she’d like to go out sometime, she said, quite loudly, “I’m not a lezzie, you fucking dyke.” I just snickered and walked away. I may have turned red, I don’t know. It happens.

Regardless, it’s not like you’re looking for a life partner at this point – you just want someone to play with; to experiment with. If someone shoots you down, fuck ’em. Just move on to someone else.

Finding Someone to Play With – The (relatively) easy route

One of the easiest, quickest ways to pick up another woman is to go to a lesbian club. Many larger cities have these. Just by virtue of the fact that you walk in the place, everyone inside is going to assume you’re into women, and you almost invariably (depending on the club) will be hit on if you stick around very long. If you’re just looking for a random fuck, then this is generally the single best option for you.

The down side to this, if you want to call it that, is that people will generally be picking you out as opposed to you picking them (you could go in and hit on someone, of course). This means you may encounter someone who’s not your type. The best way to handle this is be straightforward and honest with them and let them know. Or, lie and tell them you’re waiting on someone else. Going to a club is often a good solution if you’re not comfortable making the first move.

Using online services

Another option is using the W4W (Women for Women) section under the Personals on Craigslist or Backpage. You can peruse the ads and reply to any that interest you, or you can construct and post your own, specifying exactly what you’re looking for in a potential partner. You can meet people who live in the same town as you if you’re comfortable doing that, you could pretend you’re in town looking for a first time, or you could construct any other kind of scenario that works for you. In fact, if your job requires you to travel a good bit, using CL or BP is a really good way to meet someone in another city. Just construct an ad, post it, and sort through the replies.

There are a couple of important points to keep in mind about using CL or BP. A lot of people post/reply using fake photos, and there are a lot of guys who like to post pretending to be women, or respond to ads pretending to be women. While it’s okay to use CL/BP to locate someone, before you meet them, voice verify them – make two way phone contact and verify that the other person is actually a female. And, when you do hook up, do so in a very public place, such as a Starbucks, a mall, or some other location with a lot of people around. You should also let someone you know and trust know where you’re going. You’ll likely get replies from men who can’t seem to understand that you were seeking a woman (their eyes apparently block visual access to the “wo” on the front of that word), and may even get a reply from a couple looking for a threesome partner. How you handle those is up to you (the best way is to just ignore them).

You could also consider joining and using services such as,, or similar sites. The down side to this is that they typically cost money, but they’re usually a lot more reliable for finding someone you’re compatible with. The same rules apply when meeting someone from these sites – verify, meeting in public, etc.

The not so easy route

For many women, though, they don’t want a random person or a stranger for their first experience; they want someone they know or trust, or at the very least someone they are familiar with. The obvious problem with this is that the person of interest may not be into women and, if you elect to display some interest in them, you run the risk of alienating them if they don’t respond favorably, thereby potentially damaging a friendship.

Even if they do react well, and you are able to have that first experience, what happens if it isn’t what you’d hoped for and it turns out you are straight? Or they’re straight? Or (statistically unlikey) you’re both straight? Your relationship with them will be forever altered and things may be awkward for you. There’s no way around this – you just have to decide whether or not the risk is worth it to you.

Unless you are seeking a potential long-term relationship with a woman, I’d highly encourage you to experiment with someone random, or a casual friend you can do without should the relationship sour because of the encounter (I know that sounds terrible, but we’re dealing with reality here!).

Finding someone to play with

Assuming you’re not going to the club, or the club doesn’t work for you for some reason, or Craigslist turned out to be a shitheap, where do you go? That depends on what age range you’re looking for, really.

If you’re looking for late teens or early twenties, raves, regular dance clubs, college parties, or any other gatherings where you might find women that age is a good place to start. If you go to college, classes can be a good option. Sit close to someone who interests you and become friendly with them as the semester progresses. Talk to them, flirt with them (most women don’t recognize flirting by another woman as “flirting,” believe it or not), and eventually ask them to eat lunch/dinner with you. Befriend them, work your way into their psyche and see where it leads. Again, in this case, you’ll need to be comfortable taking the initiative.

If you’re looking for women older than that regular bars work best, especially hotel bars and those close to hotels and airports. There are a lot of women who travel on business who like to play around while they’re on the road, largely because they know they won’t have to stick around if the encounter goes south. They get to play and get out of town, and no one from home knows they’ve been playing with another woman. Pole dancing classes are good for meeting other women who’re exploring their sexuality a bit, as are jazzercise classes, or any other place where someone is working on their body (gyms, YWCAs, etc.).

Many people will suggest that if you can get some alcohol into someone, you’ll stand a better chance, as it tends to reduce inhibitions. That is true, of course, but I’m not a big fan of using someone else’s intoxication (even light intoxication) as a tool to further my own sexual agenda. I am a huge believer in the concept of fully informed consent and the presence of alcohol tends to put that into question. I do know women who hooked up while they were drunk, lived to tell about it and never mentioned it to one another again.

What if I have someone I am interested in?

If you work with, go to school with, or live near someone you’re interested in getting close to, you need to work your way into their psyche. How do you do that? Rather than spending an inordinate amount of time and space here explaining it, I’ll be recommending a book for you to read in a moment. Just hang loose. First, though,you’ll need to work out a way to figure out if they’re even remotely interested in being with another woman. The best way to do that is through investigative exploration! 😆

Find out how open they are to bisexuality or woman-on-woman sex. You can do this through any one of several mechanisms. First, you could simply bring up something from the news about bisexuality or a lesbian in the news. For example, when [W:Angelina Jolie] is in the news, make a comment about seeing why other women would be attracted to her and/or wondering if [W:Jenny Shimizu] (AJ’s publicly-admitted one-time female lover) enjoyed fucking her. See how your target reacts to that. If she reacts favorably, then that is generally a good sign.

For younger women, [W:Megan Fox] has come out as bisexual and has something close to the same kind of draw on younger women that AJ did for women who’re now in their late 20s and 30s. If a story about Megan were to show up on TV (or if you pulled one up on YouTube), you could make a statement about “going lez” for her and see what kind of reaction you get from your friend.

You can also rent a flick with a lesbian or bisexual scene in it and invite your friend over for popcorn and a movie. When the scene(s) plays watch her reaction, maybe even making a comment about how hot it is. Imagine Me and You works, and is a good movie to boot (and isn’t “in your face” lesbian). Something a bit more forward is to buy a book about lesbian sex, or a book of erotic photos of women and leave it lying around out in the open when your friend is over. Keep an eye on her and see how she react when she notices the book. With a movie, if there’s a vigorous objection to the scene, you can always deny knowing what it was about. It’d be kind of hard to do that with a book, though. 😆

Other suggestions for places/situations to exploit might include:

  • If you’re at a party, sometimes there’ll be games played where you can interact with another woman. Truth or Dare, Spin the Bottle, etc. (Yes, I know they’re juvenile!) If you have a friend you can trust, get them to dare you to kiss the woman you’re interested in.
  • If you know someone who is bisexual or lesbian, and feel that you can approach them, you may seek counsel from them. You may find that they would be willing to “initiate” you into the world of sex with women or perhaps hook you up with someone who will.
  • Use MySpace, FaceBook, or similar sites to find someone.
  • You could consider hiring a professional. Many escorts will see women in addition to men. Some even promote that they offer women first experiences, and you’re pretty much guaranteed success. The sex will be incredible, but if you’re like me, you prefer the thrill of the chase, so this might not be the best option for you if that’s what you’re looking for.


Regardless of how you come across a woman you’re interested in, you’ll need to begin the process of getting close to her. And, just as you would if you were working on a guy, you generally start out by flirting. The key to this is to flirt just like you’d want to be flirted with. Not like guys flirt with you or other women, but like you prefer to be flirted with. That’s one advantage you have – you know what make you take notice and most women will be similarly inclined. There’s no magic to it, though sometimes it takes a bit of practice (and a change in mindset) to be able to flirt as you’d wish to be flirted with.

You’ll also want to be sure you look for signs that another woman is flirting with you as well! As I said earlier, it doesn’t occur to most women that another woman might be flirting with them. We haven’t been indoctrinated culturally to “watch” for that and put up our defenses with other women like we have with men (plus we’re generally a lot more subtle about it than guys are). You know how to flirt, and so you should watch for the signs that another woman you’re with might be flirting with you and perhaps capitalize on it. After all, she may be just as interested in you as you are in her.

From this point, you’ll have to pursue the development of the relationship just as you would one with a guy, keeping in mind that you’ll need to modify your specific tactics to work with a female. Again, think about how you’d like to be approached, flirted with, seduced, etc., and apply that to your target.

Sex With a Woman

If/When you get to the point where you’re ready to actually be physical with another woman, you’re going to approach it, again, just as you would want a partner to approach you. The only real difference is that, once you get down south, there’s not going to be a cock there, but a nice, wet, warm, sweet cunt to dive into.

As with sucking cock, getting it right takes some practice, and any partner who knows this is your first time will be patient with you I promise. And, of course, each individual is unique, so even if you’re a pro at it, you’ll have to spend some time finding out where her magic spots are. There are plenty of web sites online that offer specifics on how to have sex with another woman, so I’m not going to go into all of the possible variations at this point. Google it and see what all you find – the more ideas you get, the better off you’ll be anyway.

Reading Assignment

What I’ve written above will get you started, but there are two books that you absolutely must read, regardless of your age, if you really want some good insight into how to go about hooking up with women, especially if you want to get serious about it.

The first is the Straight Girl’s Guide to Sleeping with Chicks. Author Jen Sincero provides a lot more information about potential places to pick up women and so forth, and also gets into a lot of details about positions, things to try, etc. Some of the information is basic common sense kind of stuff, but it may spark some ideas for you and is definitely worth reading if you have the time and drive to do so.

The second book is Robert Greene’s The Art of Seduction. Greene’s book is a thorough examination of the psychology behind seduction. It is long (almost 500 pages), but it explains the various types of lovers, and the various types of targets (he calls them “victims,” which I absolutely detest. “Victim” suggests non-consent.). Once you understand how the psychology works, you’ll be better equipped to apply that knowledge in your pursuits, and it will work whether you’re a male or female doing the hunting. This book will explain how to get into someone’s psyche (as I indicated you’ll need to do above) based on what type of personality they have.

I read this when I was 17 years old (twice, in fact), and credit it with my success in seducing other women (as well as providing me with an understanding of how men try to seduce women, by the way). Some of it is pretty cheesy, but the main concepts he describes about how to get into peoples’ psyche is right on target.


Those two books, combined with the concepts and ideas I’ve outlined here should give you some information to begin working on figuring out how to find someone to play with. It’s not terribly different than finding a guy to play with, it just involves a bit more effort, and an acceptance and understanding that things may not go the way you’d planned.

And keep in mind that it may just not be for you. It’s not uncommon at all for a woman to get nothing out of an experience with another female (they don’t call it bi-curiosity for nothing). If that happens to you, maybe you’re just really straight, or perhaps you picked the wrong play partner. I’d encourage you to try it again if there’s any doubt in your mind whatsoever, though. Some women just don’t click – the chemistry has to be there just as it does with a male-female combination.

I hope that helps a bit. If you have any questions, post them as comments, since others may have the same questions. I’ll try to answer them if I can. And, of course, if you want to share your ideas or experiences, feel free to do that as well.

Good luck. 😉


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