Every few months, a new debate pops up in the comments section of one of our most popular, evergreen posts — “Confession: I Want to Do My Boyfriend with a Strap-On” — written by an anonymous female contributor a few years ago. The standard fare is usually something tired about how “it’s gay and feminizing for men to be pegged, that the failure of ‘real men’ to refuse to enjoy receiving anal attention is the downfall of civilization, thanks feminazis!” But in the past few weeks, there have been some refreshingly interesting arguments questioning why it’s okay for a woman to try to convince her boyfriend to bend over when the same sexual pressure from a man on his girlfriend would be harshly criticized.

PointingOutTheObvious felt that “if a dude had pressured a chick for anal people would be pissed and calling him an asshole, yet people want to condone what this woman did, shit’s fucked up.” So POTO rewrote the original article by swapping the genders and then asked us if it was morally sound:

Our contributor, a man who wishes to remain anonymous, has a confession to make.

My girlfriend’s butt is beautiful. It’s pretty. It’s plump. It fits in the palm of my hand. I can’t keep my hands off it, and simply touching it turns me on. I’ve spanked it, kissed it, rubbed it, grabbed it, bit it — and now I want to stick something in it. My dick to be exact. I want to bend that girl over, face down, bum up, and do her in the most dirty of ways. I want to make her ass giddy with anal afternoon delight.

So last November I said to her, “I want to do you in the butt. I think it’s only fair.” She’s made me go down on her vajayjay, so I should get to poke her in the tush.

“Um, no.” She laughed nervously and changed the subject. Needless to say, this no-bullshit approach did not work.

Unwavering in my attempt to stick my dick where the sun don’t shine, I approached her again in December with a more sensitive strategy: “Just because I want to pack your fudge and you let me doesn’t mean you are gross, baby.” I thought assuring her it wouldn’t be gross, but rather a try-anything-sexual would work for sure. Sadly, this simply wasn’t the case.

“I know,” she replied, “I just don’t want a dick in my butt. It’s not going to feel good.”

With this important information, I devised a more detailed put-it-in-the-pooper plan. In January, sounding oh so scientific (and as cute as can be), I spouted off some knowledge gleaned from this very site:

“The prostate gland is similar in size and shape to a walnut. It is located at the base of the bladder and surrounds the ejaculatory ducts and urethra. It is essentially the equivalent of the female G-spot, hence it’s called the P-spot. When stimulated during anal sex, it can produce orgasms. The P-spot is your best friend and you’re ignoring him. That’s not very nice, now is it? From what I hear he is very fun to hang out with. Perhaps you should make a play date.”
I said, “See honey, even men like it, if another dude would let me do it to him, then you should definitely let me do it to you.”

Silence…more silence…then finally, what my ears have always wanted to hear. “Maybe…”

After a month of many talks about how to travel the brown brick road, we agreed that starting with lube and the head of my dick with a vibrating cock ring would be the best way to get things started. February arrived and with it a text message from my girl that read, “I’m really excited for you to do me in the butt. Wanna go get a cock ring today?” Hell yes I do. Head today, full on dick tomorrow!

Last week we went to Fascinations, a local sex shop, and purchased the lube and cock ring. We rushed home, stripped off our clothes and jumped into bed. She looked a bit uneasy.

“Are you sure you want to do this?” I asked him. “I only want to do this if you’re comfortable with it.”

“It’s probably going to feel like a turd,” she laughed. Not the response I was hoping for, but she bent over, face down, bum up, just as I’d imagined, and after applying the lube I eased the head in.

I started slow and soft, in and out, in and out, then applied a bit more pressure. After a few minutes I turned on the vibrating cock ring. It was loud. Very loud. The longer I sat there on my knees behind her, the more I felt like I should be wearing latex gloves and a lab coat; perhaps throw in a clipboard and stethoscope as well. Probing is the word that came to mind. It felt far too formal for my liking, and I could tell by her silence and her face in the mirror behind our bed that she was not enjoying the ride.

“Okay,” I said. “Let’s try a different approach.” We sat for a few minutes and discussed what would feel good. We agreed that foreplay first without the anal was a good idea.

Some anal-free fondling led to some anal-free fellatio. And when she was good and ready, I popped the head back in and started rubbing her clit at the same time. She liked this combination of front and back attention much better, as did I. But after a while my hands needed a break and I was getting tired, so we resumed the ass exploration in the spooning position. I inserted the head half-way in and angled it up towards her belly button to start. “That feels really good. I like the vibration.” Then I pushed the head all the way in and started feeling around left to right. “That doesn’t feel so good,” he said. So I started making soft, slow circles inside. She liked that a lot.

After about an hour our anal endeavor was over and the search her ass was called off. She didn’t orgasm and she was strangely quiet as we lay there. It occurred to me that maybe I was asking too much. Maybe expecting amazing orgasms from just me putting it in her ass was unrealistic. Maybe we should have thought of anal as a side dish rather than the main course. Maybe pooper stimulation just doesn’t work for some girls, just like some dudes hate having it up their ass…

Then she turned to me, (trying to please me like the submissive little bitch I treat her as) smiling, and said, “Practice makes perfect, baby. I’m ready for round two. What about you?”

Like I said, butt plug today, strap-on tomorrow.

We are big fans of the role reversal in order to expose some kind of ridiculous inequity, like sexism or racism, our favorite being Gloria Steinem’s essay “If Freud Were Phyllis,” which decimates some of his most sexist theories. But we felt PointingOutTheObvious’s attempt to do the same fell short. POTO ended with “I get that I missed a few of them, but you get what the fuck I’m sayin,” so we responded as such:

Hmmm. You missed quite a few of them. The main one being the line about the narrator having ALREADY been boinked in the butt by the partner! That’s absolutely essential. In the original article, the boyfriend has already been on the giving end of anal sex with the narrator — and now she would like the favor to be returned, for HIM to try to be the recipient of anal play like SHE has already been. That fact somewhat softens the slightly crass goal-orientation of the post. She is not pressuring her boyfriend to do something they’ve never done before, she’s just asking him to try letting her do to him what he’s already done to her.

(Also, by not giving your role-reversal treatment to the paragraph about the prostate, you inadvertently highlight the fact that men as the recipients of anal play actually makes more sense than women as recipients, because men have got a special spot internally that can especially enjoy that attention.)

We agree with you that no one should be harassed or pressured into doing something they really don’t want to do. And if this post were written by a guy who’d never enjoyed anything in his own butt, then yes, he would be a jerk. But because this writer HAS enjoyed her boyfriend up her own butt, we don’t see anything wrong with her trying to persuade him to do to the same, by using solid health info and progressive arguments against homophobic knee-jerk “No’s”.

Around the same time, IveSeenBothSides made a similar case, just more elegantly:

I’m a 28 year old woman who’s been in 2 serious relationships (the second one I’m currently married to). The man in my first relationship greatly enjoyed anal play (although he seemed embarrassed about it, not because of how I reacted to him asking mind you, I was fine with pleasuring my partner in any way he wanted). My current relationship, ie my husband, is a very firm “Hell no!” on the matter.

Now as a woman who’s experienced both sides of the fence…do I think my ex was gay? No. Do I think my husband is a homophobe? No. I think every person in different.

I don’t enjoy anal myself and there’s certain positions that just aren’t as pleasurable to me. So how can I expect my husband to do something he doesn’t want to do when he respects me enough to not ask me to do the things he knows that I dislike or find unpleasurable? On the other hand…or foot, I find having my toes sucked feels amazing (clean, right out of the shower toes mind you, otherwise that’s just gross)…..does that make me disgusting? Some people would say so regardless of cleanliness, but then there’s others who would agree with me that they love it. But the thing is, I can’t control that I like the sensation of having my toes sucked. It just feels good to me. I either like something or I don’t.

So I can’t judge someone else for liking something that I dislike, unless I want to be judged as well for things I like that others may not. But most importantly, when it comes to anything sexual, your mind has to be in it…..if every time I had my toes sucked I was thinking in my head, “Eww, that’s so disgusting!” or “Oh my gosh that tickles!” I wouldn’t find any pleasure in it. I think likewise for men who have in the back of their mind during anal play, “This doesn’t feel right, it feels gay” or “This doesn’t feel good, it hurts”, also aren’t going to get any pleasure from it. And a man shouldn’t be judged for not wanting something done to his body that he doesn’t want, any more than a woman shouldn’t be judged for not wanting something done to hers.

I felt like while reading the [original] story, I kept thinking, “If this was a story written from a man’s perspective about his girlfriend not wanting anal sex and how he pressured and talked her into it over the course of months, it’d be a different story in the comment section. Everyone would be saying how much of a jerk he was for pushing her into something she obviously wasn’t comfortable with.”

And you all know it’s true, if the roles were reversed most people wouldn’t see what this woman did as okay if she were a man pressuring a woman. I feel like if you’re partner is wanting something done TO them sexually that you’re not comfortable with doing to them, that’s one thing…but when it’s YOU wanting to do something to your partner’s body that they don’t want and are not comfortable with, it’s not okay to push the subject. If they change their mind later on down the line it should be their idea, not yours and not because you won’t stop asking them to do it. That’s just you guilt tripping or coercing them to do something you’ll later regret and they’ll later feel bitter over.

We couldn’t agree more, except with one caveat:

Like we mentioned to PointingOutTheObvious, the key to this post is that the narrator’s boyfriend has had anal sex with her butt — she is only asking to let her do with him what he has already done with her. So the comparison to a story written by a man pressuring his girlfriend to do something she didn’t want to is not quite fair. The boyfriend obviously doesn’t have a problem with anal sex in general being dirty or gay or something he just wants no part of — he’s previously enjoyed it — he just wants it one-directional, which suggests that his aversion is based more on homophobia (“it’s gay to receive”) or sexism (“it’s girly to receive”) rather than on a sexual preference he can’t control. Again, coercion ain’t cool. But this is more a case of what’s good for the goose being good for the gander.

We thought OH of OH & W summed up everything quite nicely the other day:

Love is a two way street. The more you give , the more you get. What if it was the other way around ? What if the guy wanted the girl to use strap on on him ? Should people in a loving relationship not share what they want ? Of course they do already. It’s just that this is not your everyday talked about thing. From the looks of all the strap on’s and stores about pegging on the internet, it is more prevalent than people are willing to admit. Of course it’s not something to discuss at the water cooler.

Want to encourage your boyf to bend over?
A Kinder, Gentler Way to Introduce Him to His Own Prostate