As someone who knew he was gay from age eleven and was also born by c-section, I was both confident and content with the fact that I had never come into contact with a vagina. But what would I discover if I actually gave this whole "woman" thing a try? After all, I think women are awesome in general, so maybe having sex would turn my "like" into "love." Would I enjoy it? Could I increase the size of my dating pool? With grim determination and thoughts of liberated sexuality, I set out to see.

1 (very willing) woman
1 gay man
3 gay porn magazines
1 bottle of Jack Daniels

Most people agree that it's possible to know you don't like something without experiencing it, like rock climbing or The Hills. So while the idea of female genitalia wasn't gross, it was about as sexually enticing to me as a paperweight. And so — while I had made out with girls in a we're-drunk-it's-funny kind of way — I comfortably stayed away from any downtown action.

The only problem with this lack of experience was that, as an emotional masochist, one of my favorite pastimes was developing doomed crushes on straight men. These would often be guys I was good friends with, who appreciated the way I helped them with their girl troubles (and missed my occasional grimaces of soul-crushing pain). While I would never say this to them — the straight male is a fragile and easily frightened animal — I'd think to myself, "Well, how do you know you wouldn't like making out with me if you've never done it?" I knew it was wildly hypocritical, but that didn't stop me.

So, in an effort to put my money where my mouth was (or wasn't), I decided I would have sex with a girl. It wasn't going to be easy. While in eighth grade girls often went crazy for the safety and dependability of a soon-to-be-gay guy, currently the ladies are not banging down my door. I figured two things: one, this would have to be a girl who was well aware that I was gay. No point in getting someone besides myself hurt in the process. Two, I'd want the actual experience to be as spontaneous as possible. I'd need to keep my wits about me, as I had long ago turned off the part of my brain that noticed any sort of interest on the part of womankind.

All the requirements were fulfilled one particular Friday night. Jenny was not only a good friend, she also had many of the things I look for in a guy. She is taller than I am (not hard, since I am quite short), easy-going, and a hard drinker. That drunken night at my apartment, our conversation turned to our own personal sexual frustrations, which, in your early twenties, is like saying "our own personal oxygen." And that's when I saw my chance to literally do it for science.

"I've been a bit curious, about um... havingsexwithagirl."

"Well," I said, "I've been a bit curious, about um." I clammed up. "Uh, um, uh..." I felt like a fifteen-year-old boy. I said in a quiet mumble, "...havingsexwithagirl."

She looked nonplussed. I drunkenly explained about my straight-guy philosophy, and the nature of my experiment. She considered for a moment. "Well... sure. Why not?"

And so it was on.

We started slow. If this was going to happen, I was going to do it right, goddamn it. We made out on my bed, and it felt like freshman year of high school for both of us. This was the territory I was familiar with. Normally making out with a girl was sort of fun, but knowing that it was the first step in a larger process made me hyper-aware of everything that was different. There was no stubble, for one thing, which I actually missed. And I wasn't sure if I was supposed to touch her boobs — how would I even do that? My arms moved gracelessly, looking for some nook between our bodies to exploit.

Still, the lead-up was not the point, so soon our clothes came off, and it was time. I reached into my drawer for a condom, and had the luck to pull one out that I'd gotten at a sexual-health event a couple of weeks before. The wrapper was adorned with a rainbow background and a stunning picture of a man's ass. It was both perfect and completely inappropriate. On it went.

And then I did it, full-on genital penetration. I know that there was probably a lot more preparation I should have done — going straight from making out to sex seemed like a leap you're generally not supposed to take — but it was truly a now-or-never moment. If nothing else, I was generous with the lubrication — having had nothing but gay sex, it was de rigueur. And if there was anything like an improvement over sex with a guy, it was that the concordance of male and female genitalia — both being towards the front — made missionary-position sex slightly less awkward. To my mind, though, the actual feelings in my junk, through the double screen of alcohol and latex, were pretty much the same. The whole act had a mechanical quality. Make sure you do this, make sure you touch that, and you're in business. Once again I found that boobs only served to confuse me. I knew that they were supposed to be star players in this whole sex-with-a-woman thing, but I was on top of her. How could I touch them without doing the sexual equivalent of a one-handed push up?

Commentarium (59 Comments)

Oct 08 09 - 12:16am

I agree that using a condom doesn't really give you the full extent of how wonderful a vagina can feel, but with a normal condom, at least you get the basic idea. And heck, the author probably uses condoms for anal, so he's used to that. It just dawned on me, though: given the "male butt" logo on the package, did the author use extra-thick condoms, the ones designed specifically for anal sex? Those are TERRIBLE for vaginal sex. Thick condoms suck to begin with, and a super-thick condom could easily make a vagina feel no different from an anus (since you're not feeling all that much to begin with), eliminating one of the best parts of heterosex. Anal sex is great fun and ridiculously hot, but on a strictly tactile level, vaginal sex without a condom (or with a sufficiently thin condom) is close to the Platonic ideal of Nice Places To Put One's Penis. It'd be a shame for the author to go to all that effort, only to do the equivalent of going to an acoustic concert wearing industrial-strength earplugs.

Oct 08 09 - 12:41am

Lame. Not going down on a girl during sex is like watching a movie with your eyes closed.

Oct 07 09 - 3:17pm

while the conclusion was foregone (he's GAY, y'all. condoms or no condoms, anal, oral, vaginal, mutually masturbatory, whatever, he's not sexually attracted to/isn't into bangin' chicks), the experiment itself was brilliantly executed, thoughtful, and well-written. good on ya, dude.

Oct 07 09 - 3:34pm

Did you give her a Dirty Sanchez?

Oct 07 09 - 4:01pm

nice one. bold and honest. interesting read, thanks.

Oct 07 09 - 8:00pm

After reading this, I'm petty sure the last dude I made it with is gay too

Aug 04 11 - 3:35pm
Mucho Picante

Oh c'mon now.

Apr 11 12 - 5:06pm

I was thinking something similar about an ex.

Mucho, if were a girl who'd been with a guy who acted this way, this article would pretty much just be confirmation for what you would have already suspected. >_>

Apr 11 12 - 5:09pm

Ah-hah...I hadn't...read...the full article yet...okay. Well, my ex didn't actually pull out gay porn, I mean...I wouldn't need confirmation at that point!

(I still think a dude who doesn't do any foreplay or touch my boobs is obviously gay.)

Oct 08 09 - 11:50am

Marc, I thought this story was hilarious-- in the right way. Thanks for sharing.

Oct 08 09 - 5:03pm

Interesting article -- as a "straight guy", it's something I've always wondered as well. People on both sides of the fence are so afraid to bat for the other team that they burn their bridges before they hatch. For anyone to say that they are exclusively straight or exclusively gay seems shortsighted somehow. (You know, "says the straight guy"...)

Jul 11 12 - 10:04am

as a "straight guy", it's something I have not wondered about, I've turned down sex with both genders, managed to remain friends. It is conceivable there is a man I would want to have sex with (top+bottom) haven't met him. I like anal sex, only have experience with female rears, have been both T&B like T a lot more.

Seems to me if you aren't hurting somebody, it comes down to what you want, which stems from what you like, experimentation, desire and opportunity all mixed in.

Oct 08 09 - 11:08pm

Did you give her a Dirty Sanchez?

Oct 08 09 - 11:23pm

dSc, please stop asking that. This is an actually well-written article, so don't bring it down.

Oct 09 09 - 8:38am

There is no real commitment to wholeheartedness here. I see only reluctance at every step. I'm 100% straight and I think I could have better and more passionate sex with a dude than the author's half hearted fumbling with this woman.

Oct 09 09 - 10:35am

dre -- In that case, I'm gonna have to reduce your 100% by a few points, because I was in fact surprised by how much more able to try to do this with a woman he was than I would be willing to do it with a guy. So no, you're not 100% straight.

Dec 11 11 - 7:30pm

SG: So not true. You can be 100% straight and still give gay sex a try while doing it wholeheartedly.

Oct 09 09 - 1:17pm

SG -- I think it depends on the definition. If one is completely repulsed by the sex act with a member of the opposite sex (or a member of the same sex, depending on their "starting point"), I think that is more of a mental problem. I'm not saying that homo- or heterosexuality is a mental illness. I am saying that a failure to recognize academically that the sensations experienced through a physical expression of sexuality that differs from your own can be pleasurable demonstrates and ignorance or intolerance that runs deeper than any social experiment can overcome. There are several reasons that prevent me from trying it, but they're primarily based on social reasons, not a presumed inability to experience pleasure.

Jun 11 12 - 3:00am

So... wait. It's NOT wrong if gay guys are turned off by girls but it IS wrong if straight guys are turned off by guys? How about this: I don't fuck guys because I find the idea unattractive, if not repugnant. That's not societal, I just don't find men attractive. I have no desire to stick my dick in a cat either, but does that mean I'm being closeminded? I'm not saying that homosexuality is repugnant, but to ME the idea is as alien as bestiality.

Oct 12 09 - 12:42pm

I think you may have had a way better time had you decided to try your experimen with a queer femme top. That is, if you are a bottom. She would have taken care of the situation, made you feel like a princess and fucked the shit out of you. Straight as can be!

Oct 12 09 - 12:43pm

Correction: Perhaps you should have had sex with me!

Oct 12 09 - 3:04pm

I'm surprised to learn that nipples don't play an active role in gay sex. I'm male, and (potential TMI warning) my own can be terrifically sensitive. I could also suggest that you should have spent a LITTLE time reading up on basic female anatomy as it applies to sexual intercourse, but then there are plenty of straight men who need to do the same.

Oct 12 09 - 4:35pm

SG- The test of how straight you are is not how repulsed you are by sex with the same gender. The test is how turned on you are by those of the opposite gender in conjunction with a lack of desire for the same gender.

Oct 12 09 - 6:00pm

I've never believed that a person's sexuality could be summed up with one word.

Oct 12 09 - 7:58pm

I never thought I'd enjoy sex with a guy (I'm a girl). But I let myself try it. What did I discover?

I just like sex, good sex, in general.

Now, if you lined up a guy and a girl and asked me who I wanted to have sex with, I'd still choose the girl (after I made sure a 3some wasn't possible).

Some people like it, some people don't. We're all different, and that's the beauty of the world.

Oct 13 09 - 1:11am

Simply put: Thank you...

Oct 13 09 - 9:11am

I very rarely read articles all the way to the end but this was super interesting! Thx for bothering to go through that!

Oct 14 09 - 12:43am

As a straight man with many gay friends (both male and female) this topic has risen many times. In the past I had questions about my sexuality, and even thought I was falling for a man. I gave it a shot, and much the same as our author discovered that there was something very intrinsic missing. Simply put we are what we are, and I give great kudos to our dear author for giving it a go. (Ps, my male partner found my lack of erection so amusing he actually appologised to me. Talk about embarassing. )
Thanks for showing us that the curiosity to explore does not translate to a different sexuality, just to curiosity.

Oct 13 09 - 8:58pm

NN i adore you!

Oct 15 09 - 2:14pm

Off-topic: I'd do that guy on the magazine cover, he's hot.

Oct 17 09 - 7:55am

i like guys a lot, but have never ruled out sex with a woman. when i think of a man and a woman having sex, it turns me on as much as two men or two women. i get really interested in having sex with a woman even though i like guys more.
i guess just the thought of doing something that vbiously looks fun makes me itch todo it.

Oct 18 09 - 11:57am

Thank you for this article! It was definitely entertaining as I have thought about sex with a women myself. I can that I am pretty odd myself because I like watching straight porn. I love watching the men going in and out of a girl, and as long as there not doing to many close ups of her face and her boobs then Im good. But I could NEVER actually do it with a girl. I have always been more attractive to men and I have more in common with men. You have a good friend there! Im pretty sure most girls would run and tell a friend.

Oct 21 09 - 5:07am

After thinking that I was purely gay from the ages of 12 - 23, a girl chased after me for a while and I gave in. Yes, she knew that I liked boys. When the time came, she simply slid down onto me as I was reaching for the condoms (I was trying to do the right thing!). We had explosive sex. That led to a twelve month sexual relationship.

Now I know that I'm not purely gay. I am slightly bisexual. I prefer guys but I'll be happy to have sex with a nice, willing chick if she wants me and understands the situation.

Nov 01 09 - 10:15am

I have let a few guys guys go down on me. (straight guy here). I don't think that makes me gay or bi. They put on straight porn and I just let go. There is also something about not guys. In the head. like its another dude and you don't have to worry about feelings. Just getting your dick sucked.

Nov 08 09 - 4:21pm

This is a great story. I feel like it should be published in some science journal.

Nov 12 09 - 12:56am

The thing about it is we convince ourselves to the fact, gay men because of the years of 'finding themselves' & later defending themselves on the choice to come out & be open about their sexuallity. & straight men because most are raised hating the idea. raised to think it's only right when a penis & vagina get together. Women are actually more open to all of it, physical & emotional. Keep an open mind & the limits fade. I identify myself as a gay man. but have experienced deep attraction towards women. & have had hetero sex, i didn't mind it & tried it out a few times. not because it was great. just to see if it would be easier than the first time. I had opened my mind to it. & it was easier. it was better. I enjoyed it. I still will say gay when asked. & don't actively chase women. but if it happens to come by. I wont deny

Jan 07 10 - 6:58pm

LOL! good on you mate, I have personally tried this experiment myself, it has never actually worked out though, I just have problems actually getting aroused11110 with women ... and yes boobs are very odd :S

Jan 12 10 - 12:13pm

Definitely adopting doggy style would have made matters easier AND put the breasts into play..

Jan 15 10 - 12:47pm

props to you
Personally i am bi so i think your conclusion fits someone who is one way and no real attraction to the other and were willing to experiment to see if that would change
Kudos man

Jan 21 10 - 7:11pm

I would have enjoyed some commentary on the aesthetics of the vagina from Marc's perspective as well as what he thought about the possibility of giving oral.

Mar 11 10 - 4:14pm

I applaud you at your effort. My ex just came out of the closet (it was actually the reason why we broke up) and our sex life was okay. We both got our rocks off but there was definitely something missing and I think we both knew this. If you're not into it, you're not.

Apr 13 10 - 3:56pm

The real test is to taste her.

Jun 02 10 - 10:42am

Well done, man! Best line "...the real shame would be if I actually had the capacity to enjoy it, but never bothered to find out."

Jul 13 10 - 9:14pm
u suck

that's why I'm asexual...

Aug 17 10 - 8:36pm

Thoroughly enjoyed the A for effort on the heterosexual intercourse, the humorous story, but mostly the clever writing in which it was told. Certainly felt a kindred connection not only to your style of writing, but also with a curiosity of having sex at least once with a girl, wanting to do it right, and especially, the idea of always setting yourself up for failure by falling for a straight male friend. Matter of fact, that is how I found your blog. I'm just googling different information about guys who came out later in life, but had sex with women...all motivated by a likely ill-fated crush on someone who is probably straight as an arrow, but exhibits some "gay" characteristics and occasionally says things to me that others would observe as flirtatious. I guess I'm just looking for information to corroborate the gay anomalies in his behavior....based on the odds, not a smart idea.

One day, I hope to learn not to play with fire. Your blog might have helped a small bit in that effort, so thanks for the great read.

Aug 26 10 - 9:17pm

Kudos to you. I've never tried it with another man but that's mostly due to my not knowing anyone who is into that. Personally I am a strong supporter of the old saying try everything once

Sep 11 10 - 12:57pm

Interesting article & experiment. First time I've read the like. Heard of a gay guy that eventually got hitched to a girl, & didn't go back. Never understood it tho. My ptnr was married to a girl, they had kids. But I've never understood how he cud perform - if he really wanted a guy...the above comments helped a little - but i still need to understand.

Dec 04 10 - 5:04pm

And how did she feel after the experiment?

Dec 30 10 - 3:34pm

As to the author's message to cute straight guys in their 20's, I have to say this - "Well, buddy, that's why Jesus Christ invented the strap-on dildo."

Jan 19 11 - 8:53am

very interesting story, really entertaining

Feb 11 11 - 8:51am

I think you weren't thorough enough. First, you should have tried it more than once with more than one girl. I'm not saying that you necessarily would have turned straight, but it's always possible to have a mediocre experience depending on the person, etc. Second, you needed to do more than just stick it in and hump. Break it down into categories. Explore her body with your tongue. You would have figured out the boob thing if you'd used your mouth and really gotten into them during your brief foreplay. Lots of gay guys I know LOVE female boobs.

You should have gone down on her until she came, and licked her ass as well. Really get into it, and let her give you head. Tell her she represents all women and she needs to do a great job for the team.

And I know condoms are a good idea, but if you really want to know what the female gadgetry is all about, you have to go bareback. That's hard because no sane woman should have sex with a gay guy bareback who is just experimenting unless she really knows him and trusts him. And even still probably not.
Lastly, if you're going to compare apples to apples, anal needs to be a part of it. Not only that, but she should have done you with a strap-on if you want to be thorough. Just my 2 cents.

Feb 18 11 - 12:04am
Download Joselyn

That's thought-provoking point of view. I wanr to return to your blog couple days later.

Feb 18 11 - 5:48am

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Mar 09 11 - 3:49pm

"Could I possibly enjoy sex with a woman?"

Not to belittle the author's efforts (or his admirable writing talents), but wouldn't the answer be a definite "no"? I mean, a lot of geighs (myself included) came out after at least one or two failed hookups with women--doomed attempts to find the "right girl for me"--and if there was no sexual spark felt then, why would there be one now?

That said, I think the point of this piece was to humorously encourage sexual exploration between the sexual binary of hetero/homo, so it's not like this was a pointless endeavor. I'd just be surprised if the author actually expected to get turned on by sex with a woman.

Apr 08 11 - 9:51pm

very interesting story...definitely enjoyed reading it...i honestly thought you'd be repulsed but at least you were open minded.

Nov 22 11 - 2:52pm


Jan 29 12 - 11:42pm

It's my opinion that the author really shortchanged hetero sex; since he knows he's gay and has never had straight sex, why not ASK the lady what makes for good sex and take the time to explore and just PLAY.

Instead he did a cliched, teenybopper first fuck: a little kiss, a little feel, and bangety-bang.

Feb 29 12 - 2:40pm

Thanks for the interesting article. It reminded me of my super-wacky performance at my first homosexual experience.
Nevertheless, I agree with the previous post; communicating always makes things work better... especially in a heterosexual intercourse since people are expected to work with a system they may not truly know.

Aug 12 12 - 8:14am

Great article. I have been hearing alot about married men sneaking off with gay guys. Wanted to know if my husband might be gay and what exactly a gay man having sex with a female would be like. This did answer questions. My husband loves my boobs.

Also I am totally hetero but I must say when watching porn I love watching chicks do each other. Have had the opportunity , but no . I like my masculinity through and through, The porn is all the fantasizing I need. Great article.