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Mae West said, “Too much of a good thing can be wonderful.” Which can be very true. But sometimes it can just be, well, too much. If your man is packing large down below, the trick to good sex is twofold: control the depth of penetration, and keep him the hell away from your cervix. Here are some ways to comfortably enjoy all his glory.
With him kneeling, the trick to this position is finding something slightly lower than his hips to prop your sweet ass on, like a sturdy coffee table or a pile of pillows. Sit on it and make your legs into a V-shape. When he has to enter you downward like this, it keeps him from going super deep. You get the feeling of being well-taken (oh yes!) without being impaled.
Lie on top of him on your back and have him enter you from behind. This position has a semi-awkward angle that keeps him from hitting you too deep, but still strokes the sensitive top side of your vagina. Even better: lube your upper thighs so they stimulate his shaft with every thrust. He also has direct access to finger your clit from here, which is always a bonus.
Stand facing each other and lift one of your legs, wrapping it around his waist. Have him enter you standing like this (he may have to squat a little). One of the disadvantages of standing positions with a man less bountifully endowed than yours is that you just can’t…get…him…deep…enough. But that’s the good part here. You’ll get plenty of him, just not too much. Part of this is because you’re lengthening your vaginal cavity, but don’t bring that up during. Or ever, probably.
Hard to imagine that something that starts with sitting cross-legged could be so hot, but trust. Have him sit cross-legged on the bed, and straddle him, using his raised thighs to support your butt so he doesn’t go too deep. You control the thrusts (control = good): go slow and rock back and forth, letting him slowly in deeper. Also good for deep, hot kisses, plus you’ll have a free hand for self-love on your clit.
Warning: this position is not only way advanced, but involves being in that crab walk position from grade school gym class. With him in the crab walk position, stand straddling his hips, squat down to let him enter you, then lean back onto your hands so you’re in a crab walk position too, with him inside you. Yeah, it’s kind of funny seeing each other doing a naked crab walk, but you’ll both forget that immediately when you lean back and start thrusting against him.
I’ll start this column with a confession. Male ass play is a hard topic for me to explore. (See what I did there?) I prefer to be dominated sexually, and therefore I attract hyper-alpha males who get off on being the sexual aggressor. So, other than slipping an occasional finger in an eager b-hole while I’m blowing a guy, I have very little practice in this department. Don’t get me wrong, I’m an expert in assholes, just not the anatomical kind.
But the fact that some hetero men appreciate the joy of butt play is seeping into pop culture, from Broad City’s infamous pegging episode in 2015 to Kanye’s #FingersInTheBootyAssBitch.
This is a conversation we haven’t really been having—until now. As a friend observed, “A lot of men claim they don’t like it, but in the heat of the moment THEY ALL FUCKING LOVE IT.”
IT DOESN’T MEAN YOU’RE GAY
If you’re a hetero male, and you are curious about butt stuff, I repeat: It. Does. Not. Make. You. Gay. This is very, very important to take in. I like it in the butt, and that doesn’t make me gay. It simply means you have a butt with lots of sensitive nerve endings. If your knee-jerk reaction to ass play is, “No fucking way, I’m not gay,” then congratulations, you just broadcast generations of internalized homophobia. Educate yourself. Talk it out with a shrink. Open your mind (and butthole).
The italicized quotes in this piece are from the men I talked to, all of whom promised to be perfectly candid in return for their anonymity.
I think there is a lot of conditioning that makes young men and boys psychologically terrified of somehow maybe secretly being gay and not knowing it. All the negative homophobic stuff that impacts how we feel about our masculine identity growing up. So even exploring at first was a bit taboo. Growing into being more secure in my own identity and sexuality neutralized that.
You’re led to believe that men put the thing in. Women have the thing put in them. So it’s not ‘right’ to have stuff put in you. Also, let’s face it, most things that you can put in you are the shape of a dick.
THE STIGMA IS REAL
Just the fact that Amber Rose can publicly dis Kanye for liking a “finger in the booty ass bitch,” still, in 2016, very publicly exposed the stigma of men who enjoy ass play and showed what a long way we have to go culturally before we are at full tolerance. The first step to dismantling double standards is recognizing they exist and analyzing your relationship to them.
The initial stumbling block is embracing the experience of being receptive, as we tend to be conditioned to see that as feminine or gay. Then I think there is shifting the associations from the ass as unsanitary and shameful to being an erogenous zone. Some of it is being curious and secure enough to explore. Some is becoming better educated on the whole spectrum of sexuality in general.
Maybe it’s some of the stigma that makes it work for me. I doubt it would push the same psychological buttons if there wasn’t that slight thought that you ‘shouldn’t’ be doing it. It’s like the paradox of swear words. It’s absurd that the word ‘fuck’ is shocking, but I’m happy it is, because that means I can use it to be shocking.
TIMING IS EVERYTHING
All the men I interviewed seem to agree that butt stuff at the right time feels amazing. They wanted it “occasionally,” most echoing the sentiment, “I’m happy with, happy without.” The mood needs to be just right for successful ass play no matter what the gender, and communication is always necessary.
I’m into it. Into ass play in general. But for me, it’s much more the concept than the sensation. It’s more of a mental thing. It’s the sense of transgression, rather than the nerve endings. Except for rimming. Being rimmed feels amazing whatever your headspace.
I can’t imagine my butthole is that different from yours. Sure, mine is cute and pink and not hairy and probably cleaner, but I bet all the pleasure I get to receive can be yours for the taking as well, if you just relax into the idea of it.
Rimming: always great. Fingers: often great. Pegging/larger toys: this takes patience and effort, but it can take me somewhere higher and deeper than the physical sensations alone.
One finger when already aroused, edging, and especially right before and at orgasm. They don’t call it the male g-spot for nothing!
Ass play intensifies the entire area’s pleasure sensation and heat, linking all those nerve endings in a powerful way. Seems to generate an orgasm from deep inside the pelvis and belly. Super-intense, intoxicating and deeply relaxing release.
Pegging is when a woman inserts a strap-on dildo into a man’s anus. This absolutely deserves its own column, and it will get one. For now, I’ll say this: If you aren’t familiar with it, work up to it. Pegging is the fourth base of ass play.
I dug the concept of a strong, sensual, smart woman with a strap-on. One of the first lesbian porn scenes I watched as a teenager was a group of women fucking each other with strap-ons, so I imagine that may have influenced the formation of my fantasy.
Transgression/taboo are what does it, with that, for me. It also takes quite a lot of patience and effort for me. I’m not that great at taking larger items, so there’s also the sense of achievement/overcoming something. Which probably pushes similar buttons to overcoming being spanked or some other masochistic act.
Something I learned in retrospect is how incredibly important it is to work up to anal sex. She inserted two fingers into my ass with lube, then an anal plug that was about double the size of her two fingers. I had explained that I was an anal newbie, and this gal was a pro. She was stretching me out and warming me up.
Antonia Crane wrote a fantastic piece for us in 2014 about why some soldiers like pegging. Many of the men I interviewed spoke about the adrenaline rush they get from ass play, either because of the taboo or because of the actual physical sensation.
Pegging made my skin crawl and heightened all my senses. My memory of that moment is so vivid now because the pain and shock were so extreme. I had no choice but to be completely present. And that presence of mind persisted throughout the day. Afterwards, I was awake, like a years-long fog had cleared.
Lightning shot up my spine and into my fucking irises. My eyes rolled back in my head inadvertently. I couldn’t think.
A friend said it best, “Try to make your asshole smell less like an asshole.” Maybe do some grooming so it’s not just a hairy swamp ass. Use baby wipes.
We covered risk and prevention in last week’s column, and I got some more information on anal douching (enemas). Dr. Susan Philip, director of disease prevention and control for the San Francisco Department of Public Health said, “Douching does not decrease infection risk and could actually be irritating to the rectal lining, which could potentially even increase risks for infection. People may decide to do it from a personal preference standpoint, but there are no proven health benefits like there are with barrier methods, such as condoms, dental dams, etcetera.”
If you’re in a relationship with a partner you trust, and you’re going to explore anal penetration, it won’t hurt to give yourself an enema. In fact, according to the adult film stars I spoke with, it will make for a much cleaner experience and one you will be more inclined to repeat. If you don’t know the STD status of your partner, you can still give yourself an enema, but ALWAYS USE PROTECTION.
THE BEST WAY TO BRING IT UP
Ease into the conversation if you aren’t sure where one another’s boundaries are. Men aren’t the only ones with double standards regarding male ass play. Asking questions will help you get a feel for what she’s into and what she isn’t. If you say, “Have you ever eaten a man’s ass?” and she looks like she sucked on a lemon, maybe wait until you’re more comfortable before you confess your love of getting rimmed. Or better yet, offer to try it on her first.
It depends on the partner. If it’s someone more vanilla, then it might be something I’d introduce slowly, a few things at a time, and in the context of a series of conversations about things we’re into, or might consider, either while lying in bed, or over some drinks. If it’s someone I already know to be kinky, and the conversation has escalated quickly to lists of likes, then I’d probably roll it out fairly quickly. It’s just butt stuff.
I do it myself as part of foreplay, and they usually want to take over, at which point I explain what I do and don’t like.
What is the best way to access it?
Rectally, or if you put pressure on the perineum (the ‘taint’) you can also put pressure on the prostate. If a man is on his back, insert a finger rectally and press down. There is a walnut-sized bulge. That is the prostate. If he is on all fours, press up towards the back.
Any specific tips to minimize discomfort and maximize pleasure?
It’s very important that there is adequate foreplay, stimulation, arousal and lubrication.
What is the best way to stimulate the prostate for sexual gratification?
During oral sex, with your fingers, or during regular intercourse with a finger and/or toys.
Do males have psychological resistance to this, and if so, what is the best way to overcome it?
Older men are somewhat more resistant. It wasn’t part of our sexual dialogue and activity back in the 60s, 70s and 80s. As young girls back then we were taught this wasn’t an area of pleasure for men.
The climate is changing due to the porn industry, which is full of highly-charged sexual imagery, context and behavior. Millennials have a huge amount of freedom and empowerment with their own bodies and sexuality. They are expressing this is natural and not something we should be ashamed of; that our sexuality is something we should be reveling in. Because of the Millennials, the old-school mindset is now limiting. Anyone under 30 is licking, probing, blending, and they’re sensitizing the male brain to a higher level of stimulation. Now all of us, even us older ladies, are having to keep up with this newfound love of ass play.