How to Have Sex with Lesbians (When You're a Guy)

Normally when you see an article title referring to having sex with lesbians, you’d probably assume that it was think an article geared toward women. But, in today’s case, you would be wrong. You would be very, very wrong.

One of my friends is a suave South American stud, and I remember a few years ago he would constantly – and proudly – reference his ability to have sex with lesbian women, even if they had never had sex with a guy before. Sometimes he’d say that he could even convert them.

But most of my friend group just laughed it off as idle talk. They said that the one lesbian (or at least what they thought was one) girl that he was able to hook up with had been a complete fluke. But I didn’t adopt this incredulous attitude. Not I, Colt Williams. I looked at this situation with a great deal of intrigue.

The man is a really good friend of mine, and I knew that not only had he hooked up with a couple of lesbians, but he was also dating a girl who had previously been a lesbian and had never even touched a man before. So I knew there had to be something to his claims; I knew there had to be some kind of method to the madness.

And then as I started taking a more concerted look around me, I noticed something very interesting. My friend wasn’t alone. I also thought of a couple of other acquaintances I had who were dating girls who used to be lesbians. And then to push things further, I thought of some of my girlfriends who were once entrenched lesbians but who now are dating guys (one of them just got married to a man, actually).

So toward the end of last year, I made a more concerted effort to try to unravel this mystery of lesbians. And did I succeed? Well, you’ll have to be the judge of that.

I have always had a hunch about lesbians. And this hunch is based on what I’ve come to understand about women in general.

Venus vs. Mars

When I was in high school and college, I was absolutely fearless in regards to asking girls about their sex lives and sexual practices. That’s probably why being sexual is second nature to me these days. I find sexual dynamics fascinating, but I’ve always been wary of the limited scope that men bring to situations.

Men are very dopamine-based creatures when it comes to the mating game. We just want to stick our little head in as many holes as possible, and get the neural reward for conquering another mountain. And that’s pretty much what drives us toward sex. We are very straightforward about it. We want to know if it’s happening or not. And with gay men, this paradigm is often taken to an extreme. Gay men look at each other, and know whether or not it’s on. And if it is on: there’s no hesitation.

And an interesting observation I’ve made about homosexual men is that they have absolutely no sexual interest in females (once again, this applies to most cases. Have to consider the sweeping majority here. There are always exceptions to rules). Some gay men almost seem repulsed by the idea of being around the nether parts of a woman.

But in terms of the mating game – and homosexuality – I’ve found women to be much, much different.

First off, women can have a million different motivations in the mating game when it comes to having sex:

• Some do it for pure satisfaction (and oh, women do love sex). And in my opinion, they love it more than men do)

• Some do it to create another human being (the traditional reason, if you will)

• Some do it out of vengeance or competition with other women (they are also as competitive, if not in certain cases more so, than men)

• Some do it to keep a man around and secure his resources (not necessarily gold-diggers. It can be a very mutual and loving motivation to one day start a family or to just have a strong pair bond)

• Some do it to make a living (enough said here)

• Some do it to make themselves feel better (maybe they need validation because a guy dumped them or they feel unattractive)

• Some do it because they are bored (this is not a joke; some girls will actually just engage in sex for lack of better things to do)

• Some do it to experiment (bdsm, sex toys, black or Asian guys, etc.)

There are so many other reasons too. And because women can have a million and one different motivations for having sex with a man, they will have a lot more flexible stances on sexual practices and sexual openness.

So back to high school and college. When I was in high school and college, I was also fascinated by those Girls Gone Wild videos. On one hand, it was for obvious reasons (no pun intended). But on another hand, I was asking myself: “Who are these girls? Surely they aren’t anyone *I* know.” But I really wanted to find out.

So rather than sit around and scratch my head, I set out and began asking. I asked about everything. I went to friends and acquaintances with questions like:

1. Do you ever masturbate? If so, how often?

2. Have you ever kissed a girl? Would you?

3. Have you ever thought about having a threesome? With another girl? Another guy?

4. Would you ever flash someone?

5. Would you get naked in public if no one you knew would ever find out?

I just asked question after question like these and gathered very valuable information. And this information led to my eventual hunch.

No True Scotsman

I once read a fantastic quote that I like to reference often on this site. Men like sex. Women are sex. What this means is that women truly embody every aspect and facet of the sexual belief and practice.

And this has really been confirmed through experience after experience after experience with women.

And this led to my hunch: women are open to all kinds of sexual experiences, both with men and other women. The question is to what degree it’ll be.

In my experience, I have never encountered a straight woman who would not at least kiss another straight woman. And I have rarely encountered a lesbian who would not at least kiss a straight man. And this is where women’s embodiment of all things sexual comes in. And if you ever want to inquire for yourself, I really encourage you. It can be fascinating to take a look at these things from an insider perspective and hear them straight from the horse’s mouth.

So, no matter if they are straight or a lesbian, you have a chance to get sexual with all women. And though you can’t necessarily have sex with any lesbian, there’s a large population of those who are open to it. And my friend discovered this truth long before many other men. He was truly ahead of his time in this respect.

So how do you do it?

#1: Be Open-Minded

A lot of the times when my South American friend would get messages from this certain girl who he had been hooking up with, he would often say things like: “the lesbian wants me to come over and hook up with her.” And whenever he said things like this, he would either get looks of confusion or incredulity. That is because it simply was not in the schema of most men to think that a lesbian woman would want to hook up with a straight man.

But what is interesting about the seduction game is that the limiting factor for all men in any area of women – from one night stands, to sex in public, to choking, to threesomes, and to sex with lesbians – is that they simply do not believe that it is possible. In many cases, this is the only thing that actually prevents men from having success.

This is the only thing that prevents men from having wild, book-worthy stories. Well, in the sphere of lesbians, if you have read most or all of this article up to this point, you should now at the very least be open to the possibility of it.

Women’s sexuality is all over the spectrum, and once you understand this fact, you will find that it is actually not that strange for lesbians to have sex with straight men. So you should look at the situations with curiosity and openness rather than discomfort and limited thinking. Because if you go into a situation with limited thinking, you will likely fail to have success.

Women (lesbians included) fear nothing more than being judged. So even if you encountered lesbians who would potentially want to sleep with you, you would not make any headway with them if you made them feel embarrassed or uncomfortable for having those thoughts.

So stay nonjudgmental and open-mind.

#2: Understand That Most Lesbians Are Hypersexual

I do yoga fairly regularly, and I have had this new, very funny and eccentric teacher who very often talks about being in touch with your body. And when she is demonstrating poses, she will make references to orgasmic breathing and really using your nether parts and sexual energy to anchor yourself while doing various poses during practice.

And from the first 15 minutes that I sat in that first class, I knew without a doubt that she was a lesbian. Why? Two reasons:

1. Most lesbians are hypersexual. They are very sensual people and very in touch with their bodies and their own sexual energy. But it is not that most straight women are not also as sexual. It is more so that:

2. Lesbians have permission to be more sexual. As this woman was leading the class and making her sexual comments, a lot of the class already knew her. So people were generally laughing and smiling and celebrating her for her commentary. But had most people in the class not known that she was a lesbian, or at least expected it, then the reception probably would have been much different. Because straight women who are hypersexual are considered strange or fringe individuals.

   Whereas straight women get negative feedback for being openly sexual (read: slut shaming), lesbians are celebrated for their sexual freedom by both men and women alike (albeit for different reasons).

So you have to understand that if you want to have sex with lesbians, then you yourself have to be very in touch with your deeply sexual side. And if you are not already deeply in touch with that side, then you have to be open and willing to get in touch with it.

#3: Go to Places Hippies and Hipsters Would Go

If you want to have sex with lesbians, it’s probably useful to know that the non-hyper-masculine ones tend to be hipsters or full on hippies. You can normally find them in places like jam band shows, yoga studios, Buddhist/Taoist spiritual gatherings, hipster coffee shops, meditation centers or schools, acupuncture centers, burlesque performances, etc. And this is of course with the caveat that you should only do it if you’re comfortable with these environments (or at least curious).

Lesbians seem to be individuals who are very adamant about deviating from the norm, so they are usually quirky, deeply sexual, and deeply spiritual people. And as this is a post about having sex with lesbians, I thought I’d actually point out where you’re most likely to find them.

If you live in a big city, going to your capitol hill area is probably where you’ll find the most lesbians who are open to sleeping with men.

#4: Game Lesbians Like You Would Any Other Women

A few days ago one of my good friends came to me and said that he had met a girl at his yoga class. When I heard this, I was really excited for him (though not all that surprised, as he’s quite good with women).

But he added that the situation was kind of unusual. I was intrigued.

His narrative went:

“After the class was over, I flirted with her a little bit and then asked if she wanted to go for a walk. She gave me a great big smile and said that she was definitely up for it. We then went for a really nice hour-long walk and the sparks were really flying.”

“And then… out of nowhere… she starts talking about her girlfriend.”

At this point I stopped him. I leaned in and asked if this was a platonic woman or a romantic woman. He blushed and said ‘romantic’. And then I urged him to continue.

“Yeah, so, we kept on walking and even though she mentioned her girlfriend multiple times, she kept being touchy and flirty with me. And then we got to right outside of her apartment and made out. And just when I was at my maximum level of confusion…she asked if I wanted to have a threesome!”

I lost it at this point. His energy, excitement, and surprise upon saying this was so incredibly endearing and invigorating. I was really, really happy and excited for him. But I also told him that such things are normal for lesbians.

As we already know, they can access all ends of the sexual spectrum, so her mutual attraction for both him and the girlfriend is not unusual by any means.

But he did what all men should do: he didn’t crack under the pressure of her girlfriend talk, and he kept gaming her as a normal girl.

And that’s exactly what you want to do. You want to keep the vibe extremely playful and sexual and continue to game her even if she mentions her girlfriend. She will test you to see how you react. But don’t fool yourself. -If you think a girl is flirting with you, she is flirting you.

Guys have this incredible way of second-guessing their instincts when it comes to flirtation. Just because she’s a lesbian doesn’t mean she’s not flirting with you.

My First Lesbian

So after all of this analysis and speaking with my South American friend, I knew I had to have the experience of sleeping with a lesbian myself. And my first opportunity came near the end of last year. I was having a party at my house and found myself in a refreshingly intellectually stimulating conversation with a girl who I thought had been flirting with my friend all night (don’t worry, I didn’t break the bro code, he ended up with someone else).

Through a very deep and connective interaction, she eventually revealed that she was a lesbian. But she also added that she was very attracted to some men. She also told me about some insecurities that she had about men not finding her attractive. But she was certainly an attractive woman.

So I kept flirting with her, and then knew that I had to move her as I would any other girl. So I unapologetically invited her up to our guest room in front of all the guests, and she happily acquiesced.

As we were up in the room, I began to psychologically break down her insecurities, which were admittedly rather deep. And after escalating the sexual tone, I asked her: “What if I told you I wanted to kiss you right now?”

She blushed, looked down, and didn’t say anything. I knew this was a high-pressure question so I changed the subject to something more innocent while letting it marinate in her brain. And then she began to get antsy and continued to look down and blush even while we discussed very mundane subjects. I knew the thought of us together was something that was deeply intriguing her.

And eventually, she brought it back up. She said that she wanted to have a good time with me. I responded by saying: “I do not want to end up being another guy you hate or resent.” And she reassured me that that would not happen. And to add to the dynamics of the situation, she had told me that she had known a couple of her lesbian friends who had been disappointed by a couple of sexual encounters that they had had with men in the past.

“One of my bi[sexual] friends told me one time that she had to jack a guy off with two fingers!!”

“Hmm, maybe he just had a really small penis. I bet he was either white or Asian.”

“Colt! That’s terrible! You cannot say things like that…” she paused “… okay he was Asian.”

And then I dropped one of my favorite lines: “Meredith… I just want you to know… and this is really important… I have a small penis.”

This only works if you don’t have a particularly small penis (no hate whatsoever for the guys for whom this is the case). But it’s a great tongue-in-cheek comment to say with a very serious face that releases some of the pressure of the situation but at the same time still keeping the sexual vibe going.

We joked around for a few more minutes, and then I stopped for a second and gave her ‘the look.’ And then I slowly moved toward her and made my move. And we began to make out for a few minutes.

She definitely seemed like a fish out of water, and she voiced her reticent excitement: “I think you’re really attractive, and I’m having a lot of fun, but I just don’t like not being good at things in life…”

“What do you mean?” I asked with feigned ignorance.

“Well… I’ve just never really touched a… penis… before. I really do not want to be bad at it.”

A let out a hearty laugh and reassured her that I would show her the way. And that last statement capped off what led to an intriguing and enjoyable night.

Do Some Girls Become Lesbians Because of Men?

Or rather, I should probably ask: do some girls become lesbians because of a lack of men? It is a classic sitcom joke that a man disappoints or humiliates a woman and then she quickly turns to lesbianism.

And although it seems like good fodder for TV, I’d have to say that there is a kernel of truth in these fictional narratives. I cannot say that this is the case for all girls by any means, but there are definitely some women out there – many who start out straight or at least consider themselves mostly as such – who experience some form of disillusionment because of a man, and quickly move over to experiment with lesbianism.

When I started making a more concerted effort to think about lesbianism, I started more actively noticing and being reminded of how many girls I know who dated a guy – sometimes for quite a while – broke up with the guy, started dating a girl, broke up with the girl, and then went back to dating guys.

This phenomenon is especially prevalent on college campuses. So it’s good to be aware of the fact that some girls really do like men in their heart of hearts, but are just afraid to get hurt or experience another frustrating or disappointing man.

Wrapping Up

So now let me ask you: Can you have sex with lesbians as a man? Absolutely. Even if close-minded people around you think that it is a ridiculous notion, it is really not that ridiculous of a phenomenon in the free willing society that we live in.

The sexuality of women is wide, pliable, and constantly changing. So if a woman is truly attracted to you, she will not stop you from trying to make something happen with her, regardless of what kind of label she puts on herself. The main thing that will stop you is a lack of precedent that will force you to get in your own way.

But now I have armed you with the best weapon for your arsenal: information. And now you have the insider scoop to have confidence in stepping out of your own way.

It is just up to you as to whether or not you will put on the yoke of the intrepid pioneer. Will you be like my suave South American friend, trailblazing the way in order to transform the skeptics into nonbelievers? And will you have some pretty wild adventures and make some crazy stories along the way?

Well, there is only one person who can answer that question.

Carpe diem,

Colt