Simon says, "Gimme that ass."

Simon recently asked a question that often (ok, always) lurks in the minds of men.

"I would love to rim my girlfriend but she won't have any of it. A few times when I have gone down on her and played with her, I've put one finger in her ass. I made sure it was well lubed with her pussy juices, but I don't think she likes the idea. She enjoys her ass being tickled while I finger her and stimulate her clit, and that makes her cum loads, but if I just touch her ass alone she screams at me. She's just not keen on me touching her sexy sphincter. I want to eat her and fuck her in the ass eventually. I love exploring my girl. How do I get there? In all endeavours, I am her first sexual partner."

Great questions, and thank you for sharing them. I won't claim to be an expert on the calibre of Nina Hartley, Tristan Taormino, or Jack Morin, but I'm happy to respond from the tussled silk sheets of my own experience.

Not everything here will seem relevant for you personally, Simon, but I'm sure it may for somebody. Let's start with some pre-fuck basics, k?

(1) Beware of the Chinese fingertrap

Never try to "convince" a partner to do something she hasn't already expressed a desire to do. This should be a cardinal rule for any safe, sane, consensual adult who likes to fuck.

Aw, c'mon, baby, why dontcha wanna go to a swing club? Aw, c'mon, baby, why dontcha wanna have sex with the babysitter too? Aw, c'mon, baby, let me rest the beer can on your head just this once. Aw, c'mon, baby, aw, c'mon, baby, aw, c'mon, baby. Please. Show some dignity.

Even if she has been fantasizing about anal play (or bondage or spanking or whatever), the more she feels pressured, the less likely she'll want to explore. That is the Chinese fingertrap: the more you struggle, the more you don't get want you want. Ask and discuss, sure, but don't hound her. If things reach that point, you can either reconsider the relationship if it's that important to you, or you can shut up and watch YouPorn. Trust me on this: when you listen to her (and I mean genuinely, not as some dickhead manipulative strategem), when she feels that her needs and desires are being respected by you, her lover, she'll be far more willing to experiment with you. Why? Because she'll trust you, and in trusting you, experimentation will feel like the fun it should be and not the coercion it could turn into. And woe betide you if you fuck up that trust, especially if you're her first partner ever. Your dick is swinging over some fragile orchids, man.

(2) Put yourself in her place

Sex, and anal play especially, requires that trust. How much? Consider a Maxim magazine-style analogy: see her enjoy a pitcher or three of margaritas with the girls, and then give her the keys to your 2009 Murcielago. It's only a car, right?

Exactly. And it's only her ass.

While you're at it, ask yourself: how might you respond if she asked for a threesome... you, she, and your best friend or some dude she found on Craigslist or the tall, Italian concierge at the Hilton, and she wants to watch you guys go at it too. She wants you to get fucked in your ass while she's watching from the couch and jilling. Don't laugh: many women get off on gay porn, dude, and there's a reason.

Sure, you have needs and desires too. You want her ass, and that's cool. Sure, as your lover, she ideally would want to be GGG with them and help you out. But it's all in the attitude, intent, and delivery, especially when it comes to potential discomfort to her body (or her heart).

And if there's any lingering question, here's a lab-tested Rogue-approved method for comprehension: wearing some well lubricated latex gloves, explore yourself. Get an idea of what sensations you'll be escorting her through. When you feel ready, get yourself a modestly-sized dildo, buttplug or similar toy, some of your favourite non-sticky lubricant, close your bedroom door, and try it out. Trust me: you'll gain respect for your partner's backdoor right fucking quick. You might even discover your prostate (I haven't). You might even discover that you like it (I'm iffy). And, it's your body, so, no, it doesn't "make you gay."

(3) Do not regress to the third grade

This might be TMI for you, but it's important. "Bodies," Shayne often liked to remind me, "poop." Deal with it. Naturally, an intelligent person will comfortably prepare if she or he expects to engage in anal play (Diva discovered her appreciation for enemas this way, to my complete ignorance at the time), but sometimes the unexpected happens. Take this to heart: if you ever have any intention of seeing your partner feel comfortable enough to want to do this again, under no circumstances have a freak-out if you happen to acquire some body-matter on your cock. Most likely, you will know this is occuring before it becomes a problem. In my experience, it's very rare.

Pre-penetration probing helps: by the middle knuckle or so, you'll feel blockage if it's present, and then it would be time to wash hands and progress casually to other things. If something more significant occurs, don't lose your cool. Stop what you're doing, kiss her on the shoulder, and suggest you take a time-out for a sensual shower together. Maybe you kept a moist, warm towel near the bed just in case.

Relax about it. If you would expect her to wipe up your blood or puke after a car accident, she can damn well expect you to behave like a mature dude if you happen to encounter the tiniest hint of waste during a moment of passion. The last thing you want is to have your partner mortified by not only what might be happening, but by you regressing to age twelve. In my experience, this almost never happens to any great extent, but this is a moment that literally separates the men from the boys: don't fuck it up.

(4) "You never go ass to mouth, Randall!"

Remember that while porn may be sex, not all sex is porn. When I was in my early teens, I learned my first lessons about sex from three sources: porn, Cosmopolitan magazine, and Our Bodies, Ourselves. I'd still recommend the book to youth. The magazine? Probably not. And porn?

When I discovered porn, it still featured enough semblance of storyline and plot twist that perceptive kids like me actually learned something positive about sex from time to time. Most post-80s porn however, especially "gonzo" porn, is so bereft of sensuality that one would think that most women can take a ten-inch cock in the ass while also blowing two guys and feel as comfortable as if they were getting a pedicure.

Think about how many men (and women, probably) are growing up today with the unconscious expectation that this is typical, desirable, "normal."

Like you, I enjoy porn. But I also know that when I'm with a partner who is new at something, I remember that my every move is going to make a lasting impression. You'd be busting your partner's mental cherry as much as her vaginal or anal one, so you have a duty to make sure that her introduction to anal play is a positive experience that she'll want to repeat.

This means that you must be patient, nurturing, listen to her body language, be patient some more, and then be more patient. Know that not all women will respond the same way, and be prepared to adjust yourself to suit her responses. Have no expectations, especially about full penetration during the first few tries. Get used to the idea that she has to get used to the idea that her anus is being explored, espcially if she hasn't explored it herself during her own jilling sessions.

Always wash your hands before and after anal play (try gloves). Never insert a finger or a toy that's been in the ass into pussy. And, despite what you see in porn, never go ass-to-mouth.

That's a lot of basic ground to cover. Let's get to the crux of your question now, mm?

(5) How do I get there?

Simon, your partner might be 'screaming at you when you touch her (anus) alone' because you're not giving her the gradual build-up she needs, she's feeling pressured, she's self-conscious, she doesn't like it as much as you might think, or any of the above combined. If she is responding well to your touch when she's hot and randy, then it might just be a question of build-up and overeagerness, but only she can say. Have you asked her, and in a non-demanding way? Do you guys take sexual "time-outs" to talk, really talk, about what you're doing with each other? If you're her first partner, then she's probably in a world of overload as it is, so helping her process what she's discovering about herself, about you, about bodies, would probably do her (and you) a world of good.

But, that said, if she wants to explore anal territory, you owe it to her to go at her own pace. She already knows that you want it: give her time to find reason why she may (or may not) want it too.

If she doesn't like rimming, she doesn't like rimming. It's a freaky sensation for many people (personally, I love watching a partner go through the discovery when I'm doing it) because a part of the brain is shouting Hey! Wait! and another part is cooing WooOOoOo...

If and when she does though, explore her slowly. During the first time, simply caress and stroke the outside ring of her sphincter, teasing it, pressing gently on it and swirling your fingertip there without making any penetration at all. Do this while going down on her, massaging her, fucking her slow. If and when she wants more attention there, ask her to let you know, and be prepared to stop at a moment's notice.

Her pussy juices are not enough lubricant, and what might make its way there may likely get absorbed in skin after a while. The same with spit. Use lube, and lots of it. Then use some more. The sheets can get washed.

When the time comes for you to begin digital penetration, go slow and easy. Keep asking how she feels. Use your fingers to gently spread her anus very, very gradually. Use more lube. Don't poke: probe. Do a little more some other night, and so on. In time, you'll be able to ease two, maybe three fingers into her shallowly, and as you continue, as she gets used to the sensations, she may find herself enjoying more.

When it does come time for cock, remind her to relax and breathe deeply. Let this first night be one of extreme pampering for her: a hot bath, a massage, see that she cums at least once before you do anything. Give her awesome head. You want her as relaxed as possible, as accepting as possible. If she's new and you don't have the patience to do this, you're not worthy to be the man to slip cock into her ass. It's just that simple.

And when you do slip cock to her, remember that your head will the widest part of you. It's when the glans makes its way just past the sphincter, the "pop," when she'll have reached a peak of sensation. It's all about depth and girth from there, so take it easy. Use really shallow thrusts. Let her be the one to buck back toward you first. If all goes well, she'll reach a threshold where the sensations will change for her and it's choir practice from there.

What I'm suggesting is this: when it comes to anal, forget about your own cockpleasure for a while. Nurture her into discovering what pleases her there. In time, she'll reach a point where her receptive levels will be in sync enough with what your cock wants that you'll be fucking her just fine, and she'll be enjoying it. Unless she discovers that she doesn't... in which case, you accept it as a boundary, case closed for forseeable future.

(6) Informed lovers are hot lovers

Instead of watching hardcore video, try opening some wine and do some reading together, exploring Jack Morin's Anal Pleasure and Health or Tristan Taormino's Ultimate Guide To Anal Sex For Women. You might also enjoy Nina Hartley's Guide To Anal Sex on DVD. Or, if you're feeling particularly social, explore the net for sex-positive shops or events in your area where anal education workshops are possibly presented.



But, in the end (ha!), I'm still a guy sharing these thoughts and ideas. Some commentary from the women would definitely be in order. In an informal textmessaging survey today, I asked some of my hot and spicy friends about their experiences. The question was:

"What do you like, and dislike, the most about anal sex?"

Alix: I like it because I cum harder from that than anything else. Plus, I love being face-down, and I feel like I can give up a lot of control and just BE, just plain enjoy when a thick cock stretches me. I like the intensity of the feeling the best, the line of almost pain to pleasure. Great question.

Molly: I think what I like most is crossing that threshold from a bit painful to a whole new kind of pleasure and orgasm. What I dislike is probably when it's rushed and the ensuing injury causes discomfort for days.

Kay responded by email: Anal is still a relatively new experience for me. I've only had it twice, and only the first time was successful. The second time, I made him stop because he was hurting me. Not sure why, not enough lube, not enough warm-up with toys beforehand, something. But I know its never supposed to hurt, and it did, so I called a halt to the proceedings, much to my partner's dismay.

Still, I love the feeling of a cock sliding into my ass... that first pop as his head eases in. Him holding very still for a moment or two while I adjust. And then, him still not moving, but letting me move myself back, further onto his shaft, one teeny tiny bit at a time, till he's fully in me. That feeling, that incredible feeling, of fullness. Of a cock pressing into my gspot from an entirely different angle, stimulating it in a way that I have never, ever felt before. I also love playing with my clit while my ass is being fucked, and if the guy can reach around me enough to bury a few fingers in my pussy at the same time, all the better. I had an orgasm almost immediately that way the first time I got fucked in my ass.

But I don't like the fact that when having anal, at least for me, every time I have to start from scratch: fingers, then toy, then bigger toy, then cock. I'm tiny and require a lot of warm up, and anyone trying to just shove their cock in there without warming me up sufficiently first will be rebuffed. Immediately.

Which leads me to my next dislike, which isn't about anal sex, per se, but rather the pressure I have received throughout my entire life by men for me to let them fuck my ass. Why, why, why so obsessed? It became rather monotonous at around the age of twenty or so, and I wasn't ready (didn't think I'd ever be ready, to be honest) and eventually started tuning out whenever the subject was brought up. I did have someone try to 'slip it in' during regular sex one time when I was drunk, and I screamed so loud that I practically burst my own eardrum. Big, big mistake. I dumped the guy immediately. Asshole jerk.

Simon, I hope this helped. I also hope that you and the other readers here, especially the bevy of magnificent women who cum here, will continue to share thoughts and comments. Happy buggering!



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