Ask Professor Foxy: How Do I Have Sex With a Straight, Cis Guy?

This week-end column “Ask Professor Foxy” will regularly contain sexually explicit material. This material is likely not safe for work viewing. The title of the column will include the major topic of the post, so please read the topic when deciding whether or not to read the entire column.

Hi Professor Foxy,

I’ve been reading you column since you began writing for feministing and I love it. You’re the only person I can think of to turn too.

So I’m a mid-twenties queer lady with a conundrum. I have identified as queer or gay or a lesbian, depending on my mood, though these days I just think of myself as queer. I have never had a boyfriend or had sex with a cis man. I have mostly dated and slept with femme cis women. But lately I have found myself deeply attracted to cis men. I’ve been watching straight porn, fantasizing about men, and thinking about it frequently. This is something I’ve experienced before, but whenever I fooled around with guys it was boring. To be fair, this was all in my teenage years, and I have not hooked up with a guy in almost 6 years. I’ve changed a lot since then, and am light-years away from the awkward, self-conscious teenager I once was.

So anyway there’s this guy (I’m sure you saw that coming). I am attracted to him, I’m pretty sure he’s attracted to me. We are incredibly flirty and sexual, super affectionate with each other, and talk about sex a lot. I know I could have sex with him if I wanted to. And well… I want to. He knows I have never really been with a cis dude, and is totally cool about queer stuff. We get along really well, we’ve only known each other a month or two but I have a major crush on him. I can’t remember the last time I crushed on a dude. In the past I have ignored any attractions I had to men because it was so hard to come out as gay, and I felt like I had to stick to what I said, and sleep with ladies.

But I want to actually explore these attractions now that I have been letting myself experience them more and more lately. (and now that I have a more fluid understanding of sexuality and gender). What it comes down to is: I want to have sex with a guy, but I’m scared that I won’t know what to do. I don’t know how to please a man sexually, or even allow myself to feel pleasure, and I’m incredibly anxious about being bad in bed. I’m also worried it will bring up body issues for me, I used to be anorexic and now have a mostly healthy relationship to my body. I’m a curvy girl, some might even call me fat, but women have always made me feel sexy and beautiful, despite scars, stretch marks and imperfections. I worry that a guy wouldn’t understand or would be more judgmental.

How can I feel confident in bed as a 26-year-old woman who’s never slept with a man before? I really want to experiment and explore my desires, but what if I’m awful in bed or he hates my body?

Thanks for all you do, Foxy.

Potential Hasbian in San Francisco

Dear Potential Hasbian,

Yay for being light years away from our awkward earlier selves (even when we’re feeling a tad insecure)!  You’ve learned that desires are not stationary and now you’re ready to act that out. You’ve been having these desires for a while and now you’ve found someone who may actually fit them: take a minute to celebrate.

Being good in bed is not defined by the gender of the person we are having sex with. All the skills you’ve learned with earlier partners will still translate. What makes you a good lover? Do you have a sense of humor? Are you toppy, bottomy? Receptive to suggestions? These are likely already coming across in your flirty exchanges and they will still be there. And if there are certain things you may be less comfortable with (sucking cis cock comes to mind) then don’t do them. On the other hand, if you’ve been dreaming of sucking cis cock with a guy you feel attracted to, now you’ve got your chance. Enjoy! Let’s also not forget a queer girl’s best resource in this case (after Professor Foxy, of course), a good, non-judgmental gay boy friend who can walk you through the cis male body like nobody’s business.

He is signing up to sleep with a queer/gay/lesbian. He finds you hot and is not likely expecting sex to be the same as it is with a straight girl. Frankly, that is probably one of things he finds hot about you: the idea of having sex with someone from a different sexual background. You may be giving him the freedom to act out his hidden fantasies too. Have fun finding out what he wants and giving him the space to not have the same expectations.

It may bring up body issues for you, but it may make you feel super sexy and beautiful. Straight chicks don’t have perfect bodies either and if he is looking for whatever scar-free, stretch-mark free, “perfect” body the media has fed him, he ain’t worth it. Some straight guys are super judgmental, so are some queer women.

And, to point out the obvious, he’s flirting and being affectionate, he knows what your body is generally like and already finds you hot.

Put on whatever outfit makes you feel hot and good about your body. Go to dinner/drinks/coffee and have a flirty talk. You’ve already got a good base. Ask him what he wants, tell him what you want. If it feels right, take him home. Use latex barriers as appropriate, have some emergency contraception around just in case, and let go. If you aren’t feeling great about your body or still a little nervous, leave the lights off.

You have a fantasy and you’ve found someone who is likely able to complete it. What an amazing opportunity! All signs are pointing towards a fun, exploratory time. If it doesn’t work out, you’ve taken a major step towards completing a fantasy and will be even more ready the next time an opportunity comes along.

Best,

Professor Foxy

If you have a question for Professor Foxy, send it to ProfessorFoxyATfeministingDOTcom.

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2 Comments

  1. Posted August 21, 2010 at 4:21 pm | Permalink

    Hey Potential Hasbian,
    Like you I’m also a curvy girl, recently I had sex for the first time EVER with one of my guy friends. I’ve also had body issues especially with my recent weight gain and normally private nature. I was a little nervous once he began undressing me, because he was the first guy to see me completly naked, but soon after I felt very comfortable being naked in front of him. So comfortable that I wasn’t really nervous about the expirience.

    I think if you trust the person and get the issue of protection taken care of, maybe that it’ll be easy to turn those nervous/shy/body concious, feelings off, but that was my expirience.
    Good luck and enjoy yourself.

  2. Posted August 23, 2010 at 3:31 pm | Permalink

    Potential Hasbian, as long as this guy knows what he’s getting into and you can communicate well with him, go ahead and experiment. I’ve been the last-boyfriend and the cis-dude-experiment for several lesbian-identified women. Some of those experiences were fun, some fell flat but did no harm, I learned a lot and have some good memories, and one lesbian friend that I fooled around with, fucked, bottomed to and topped alongside about fifteen years ago is still a friend, and we’re both settled down in the ‘burbs with kids now. If I had it to do all over again, the only thing I’d do differently was more talking about what we wanted and didn’t want and liked and didn’t like.

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