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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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The Feministing Five: Jay Smooth

BERJAYAJay Smooth, as longtime readers of Feministing will know, is one of our favorite commentators and male allies. Jay is the founder of New York City’s longest running hip hop radio show, WBAI’s “Underground Railroad,” which has been around for twenty years now. You can also hear him on NPR’s “Morning Edition” every week, talking music and culture.

But what really got our attention, and what secured Jay’s inclusion in the ranks of Salon’s Sexiest Men Living in 2008, is the commentary he does about the intersection of race, gender, politics and pop culture. At his website, Ill Doctrine, he does trenchant, funny and thought-provoking commentary on everything from the phrase “no homo” to the 2008 Republican National Convention.

Most recently, Jay has garnered attention for his video “How to Tell People they Sound Racist,” a fascinating guide to having a productive conversation about the most divisive issue in American culture and politics. The video, which should be shown to every incoming college freshman (and every pundit, and every one of your friends, and everyone who wants to be included in our national discussion about race), is three minutes of desperately-needed genius, and with it, Jay has done us a real service (seriously, watch it).

It was a genuine pleasure to be able to pick Jay’s brain for half an hour, to hear how his experiences of race have shaped his views on gender and to find out exactly which Feministing editor he wants to take to a desert island.

And now, without further ado, the Feministing Five, with Jay Smooth.

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What We Missed.

On the female victims of the flood in Pakistan.

“Mama grizzlies” and their race problems.

A drug to treat congenital adrenal hyperplasia can also “curb” potential homosexuality.

One fifth of Americans think that Obama is a Muslim. I don’t like to call people stupid, I prefer to disprove their arguments, but this is stupid. And scary.

Have a good weekend folks!

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Life Lessons from the Kardashians

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I’m ashamed to say but I have a minor obsession with “Khloe and Kourtney Take Miami.” Don’t judge me. I never watched any of the Kardashian E! shows until a few months ago when my friend put it on and I got sucked into the madness. Next thing I knew I was watching marathons and episodes 2 or 3 times. Smh. But I’ve found that watching this trainwreck of vapid dialogue, puffy cheekbones and self-sabotage can be both distressing and therapeutic.

The first episode I saw featured a pregnant Kourtney (who looks the youngest but is the oldest) and the drunken antics of her sociopath boyfriend (now babydaddy) Scott in Las Vegas. In this infamous episode, the family flies to Vegas for Kim’s birthday dinner and party which is a huge promo opp for the family and a simultaneous dinner with some potential investors for Kim and Kris’s (the mom) diet pills. Scott drinks all day with the rest of the guys (including the younger Kardashian brother Rob) and gets so wasted that when it’s time to get ready for the party, he’s too trashed to go anywhere. Kris bitches Scott out (after she finds him and Rob in a drunken testosterone-fueled wrestling match) and they all leave him at the hotel to sober up.

Fast forward to the dinner where scumbag Scott rolls up still drunk to try to show his face, since he is supposed to be representing the Kardashian’s business. The waiter refuses serve him anymore alcohol (under Kris’s orders) so Scott verbally assaults the waiter and then shoves a $100 in his mouth…and then asks the poor man if he wants another one. See it in the clip below:

I was appalled but hooked.

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Social justice philanthropy

The true measure of the wealthy should be their generosity, said Bradford Smith, president of the Foundation Center.

“If philanthropy is indeed becoming the new status symbol of the wealthy it will do a lot more to change the world than buying Gucci bags,” he said.

This is an excerpt from a recent Reuters article about the way in which philanthropy has become a new status symbol among the ultra-wealthy. On the one hand, it’s promising and true. Indeed, if more wealthy people were donating to Oxfam, that would have more of a social impact than were they to use this same amount of money on a shopping spree at Tiffany’s. It doesn’t matter what their motivation is as long as it gets money out of their bank accounts and into those of organizations doing good work around the world.

On the other hand, it reminds me of how wildly far we are from going after real parity when we’re giddy about the fact that rich people might donate their monthly handbag budget to “those less fortunate.” As INCITE! details in The Revolution Will Not Be Funded, the dynamics of philanthropy are far more complex than most of us admit. Wealthy donors making idiosyncratic choices about who deserves money, and how much, replicates the power dynamics that created inequalities in the first place, and rarely do much to foster real, systemic change. For more on this and other foundational ideas of “social justice philanthropy”–a radical new approach to wealth redistribution, check out Tyrone Boucher, below, who also writes a blog called Enough. (This, by the way, is one of eight new videos that some friends of mine have just produced in conjunction with my new book, Do It Anyway.)

Thanks to Felice for the heads up.

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