directions toward the tender part, part 2

This post continues my directions for anal-sex beginners; you can read the first part here. Go and read it if you haven't already. I'll wait until you get back.

Step 5: The In, The In & Out, The Out

The In: Ok, so you’re in bed, you’re prepped. Let us assume some pre-anal lovin’ steps that follow whatever erotic dance you and yours enjoy. Remove the butt plug, or have your partner do so (see step 3 in part 1 on removal).  Now you’re ready to get spelunked as you’ve never been before.

I like every position for buttfucking—missionary (though I doubt it’s what they had in mind), doggystyle, woman-on-top—it’s all good. But if you are feeling nervous, be on top. That way you can control how deeply the cock or dildo goes in your ass. Plus, I think that it’s nice to be able to see your lover’s face when you’re doing something new. It feels less scary if you can make eye contact. Moreover, a position facing one another facilitates communication between you and your buttfucker, and that, in the improbable words of ex-con Martha Stewart, is a good thing.

You or your lover need to lube the cock or dildo. Your ass has been pre-lubed by the plug, but you can still add more if you want. If you’re on top, it’s easiest if you guide the cock or dildo into your own ass, sort of sitting down on it gently. If you’re on the bottom, it’s easiest if your partner slides it into you, still gently. If your partner is holding a dildo in his or her hand, there are obviously many more position options. Pick one you think you’ll be most relaxed in and go with that. Be gentle with yourself (and if you are the lover, rather than the lovee, be gentle with him or her). Take it slowly and find what feels good for you

Take deep breaths. Relax as much as you can. Go slowly. Accept that for all your play you will be feeling something new and initially uncomfortable. It will pass and in its place will be, if you’re anything like me, an amazing, indescribably, primal pleasure.

Essentially, it’s going to break down like this: the head of the cock will enter you a lot like the buttplug—there will be discomfort and a kind of audible “pop.” That’s where the similarity to a buttplug ends, for a cock is a lot longer than your plug. There’s more of it, and you will learn to accommodate what you want to accommodate. Understand that you will feel a bit freaked and a bit overwhelmed. It’s ok.

One way to relax is to push out slightly with your rectum. Oddly, this opens you up so that you can accept more cock in you. Since you’ve cleaned house, you don’t need to worry about poohing, even though you will feel like you have to (however, you’ll be expecting this feeling because you’ve been playing on your own). You aren’t going to pooh. It’s all cool, baby. Just relax with the knowledge that the exquisite need to expulse that object that has just entered your rectum will pass. I promise.

I’m not going to lie to you; you will feel some pain. You will feel some pressure. You may have to tell your partner to pause while he or it enters you. Do so. You should be in control. Understand that when your lover pauses, your body will relax. Work incrementally, and if you need, have your lover withdraw and add more lube.

The In & the Out: When you begin to feel the need to poop dwindle, you will begin to experience a feeling of pleasure. Trust me. It’s there; you just need to find it. Free your ass and your mind will follow. You will want to experiment with rhythms. Some people like quick, short strokes. Others like slower, smoother strokes. I enjoy long, deep strokes that pause at their apex.

If you’re a woman, try to aim the cock toward your g-spot through the wall separating your rectum and your vagina. It’s actually pretty easy—I do it by tilting my pelvis up and forward toward my lover if I’m on top of him or under him, or tilting up and back, also toward my lover, if he’s behind me.

If you’re a man, try to aim the cock or dildo toward your prostate. (I have no idea how easy that is being utterly lacking in one and, hypocritically, not being into the bendover boyfriend thing my own darn self. I guess this is where your pre-game onesy warm-up will be helpful.)

One thing to note about anal sex that is very different from vaginal sex is this: you don’t want the cock or the dildo to pop out, really. You kind of just want that cock to stay in there because removal can be rather messy. And re-entry can be kind of uncomfortable. Therefore changing positions can be tricky. I’m not saying it’s impossible, but I am saying that it can be problematic. Therefore find a position you like at the beginning, at least in your virgin anal days, and stick with it.

I like to touch my clit while I’m buttfucking. I like to touch my clit in general, but I really like to touch it when I have a lovely hard cock up my ass. Nothing, really, makes me come harder. But I’ve said this before, and this is your time in the sun, so figure out what works for you. If you are a dude and you are enjoying some anal play, you probably want to have your lover touch your cock with hands or mouth. Or you can let your lover concentrate on your ass and watch while you touch your own. (We like to watch.)

Expect your body to experience and react in new and unforeseen ways. It’s cool. As long as you don’t feel excessive pain, you are good. Excessive pain: bad. A little pleasurable pain: good. Only you know what you’re feeling, trust yourself and go with it.

Finally, don’t freak if you don’t come the first time. I mean, how often in your sexual history have you? It took me many years to learn to love a lot of different sex acts. Give yourself permission just to experience new things, and you’ll be amazed what pleasure you can feel.

The Out: Removing a cock or dildo from a rectum is not at all like removing it from a vagina. You need to let the cock get a little soft, actually, and your man needs to remember to hold onto his condom when he withdraws to lessen the chance he’ll leave you a little party (dis)favor. Regardless of whether it is a cock or a dildo leaving your rectum, you need it to exit in a slow and orderly fashion. Don’t just rip it out or it may be joined by Mr. Hanky. Nothing puts a damper on the naughty hot monkey butt lovin’ like surprise pooh.

Exit slowly. Hope for the best, and keep your towel handy.

To recap: lube; go slow; talk; be patient; breathe; repeat; enjoy; towel.

Step 6: Love Me Tender, Love Me Sweet

Here’s the big fat downside to anal: after it you have to negotiate the difficult terrain between the hygienic and the emotional. Poop is dirty; butt-fucking is vulnerability-making. You need to clean up and you need to cuddle. But you need to clean up first.

If you’re a chick who has been butt-fucked or a dude who has been buttfucking, you need to pee to cleanse your urethra to help prevent a urinary tract infection. If you have been the buttfuckee of either gender, you’re going to need to poop. Which you’ll probably want to do in private, I’m assuming. The rule here is this: if there’s one bathroom the buttfuckee goes first (and the buttfucker has to clean the toys. I didn’t make the rules; I just have to give them out). You can, if you want after your various forms of elimination, invite your lover into the bathroom to shower with you, which can be quite nice. (And if you're the man and you've had buttsex without a condom, you need to clean really very well. Might I suggest anti-bacterial soap?)

However, my suggestion is this: wash up quickly and hop back into bed. Because you need to cuddle.

Anal is incredibly emotional. It takes a transporting leap of trust to accept an object as large as a cock in your rectum. It takes an almost metaphysical level of openness to find pleasure in that acceptance. You and your lover need to acknowledge this. Nothing gives me greater pleasure than anal sex, but also nothing makes me feel more vulnerable, more in need of reassurance and affection, more craving of ruthless tenderness than being fucked in my ass.

You may be somewhat blindsided by the emotional repercussions of buttfucking. I have been. I don’t do it with anyone I don’t trust within an inch of my emotional life because I have learned that to do so is to throw an openhouse to heartache. You might be different, but even if you are, some lovingkind cuddling never goes amiss.

Take care of yourselves together.

Step 7: Odds & Ends

Odds 1) D’jaevle asked me how many times in a night you can buttfuck. I don’t know. How many times in a night can you buttfuck? It’s really the call of the ass. And that is why you don’t want to do the sodomy dance when you’re impaired. It’s just too dangerous. Sure, have a cocktail (insert pun here), or smoke a bowl. But don’t be totally fucked up before you totally fuck. D’jaevle, if your lady love can take it in her accommodating behind three or four times in a night, and you all are being scrutinously hygienic, knock yourselves out and color me impressed.

If you can only do it once, that’s good too. My last lover, Donny, has incredible stamina and could fuck for an hour or more. I mean, fuck. For. An. Hour. And sometimes it got to be a bit much, and I’d have to whimper “Poodle,” my safeword, and we’d stop.

It is always up to the discretion of the buttfuckee to say when. Always.

Odds 2) Have a sense of humor because accidents will happen. The ass is where the pooh lives, and as much as you may do your best to prevent it, the pooh will escape. Your pooh is Steve McQueen; it’s in prison and it wants to make a break for it, and it will, often at inopportune times. You gotta, metaphorically, let it go and giggle.

And then clean up.

Odds 3) Don’t worry if it doesn’t work for you the first time. Like St. John’s Cathedral, everyone’s sexuality is constantly under construction. I didn’t love buttfucking the first time I did it way back around fifteen years ago. It took me until the last couple of years to relish my buttsluttery, something I suspect that has to do with a more holistic acceptance of my sexuality in general, rather than something directly having to do with an evolution of my ass.

But if you like it, try it again, even if you don’t come. It can take a while to figure out what works for you and yours. As long as you talk (and use a lot of lube), it’s all just good, dirty fun.

Ends 1) You may find yourself sore the next day. You may even bleed a little bit. If you’re really sore, or if you bleed a lot, you need to go to a doctor, and for the love of god tell the truth. You did not accidentally sit on something. You had anal. Accept and move on.

You cannot buttfuck every day of the week. I consider it more of a treat than a meat. I wouldn’t eat bacon every day—nor should I—but a BLT once a week isn’t going to do my heart any badness. Trust your ass (and your heart) and do what seems right for you.

Ends 2) I don’t claim this overlong post does to be the final word in buttfucking. It’s not. It’s just a little overview. To pare it down to the essential components: lube, safety, play, talk, patience, and love. And a towel.

It is the tender part, this anal sex, as much as it is the forbidden zone, the naughtiest of the naughty bits, the love that dare not speak its name. It is the tender part; treat it with joy, with laughter, with reverence, with patience. Treat it with love.

And lube. Lots and lots and lots and lots and lots of lube.

Comments

[S.C.]

Again, my compliments on a very well written How-To.

[figleaf]

I repeat: I've read a lot of other anal instruction. Yours tells you *how.* I especially appreciated your emphasis on the emotional elements and the need for cuddling and/or emotional release after. Thanks again, CG. It means a lot.

figleaf

[Alohalani]

Hold on to that thought, darling. I'm running off to class. Miss you! (Sexy wench!)

Adoringly yours,

Alohalani

[introspectre]

Free your ass and your mind will follow! Hah! Now I must go get funky with my buttplug, etc. My mind requires freeing.

[Gander]

oops, there I go again. CG, you're a veritable ambassador to buggery. Put it in the stack with The Cunting Linguist's guides to oral for some fabulous, motivational primers to doing it with style and grace. Thanks.

[Quanzer]

This is great. Even though I've had experience with this before, I could use this step by step how-to guide to convince any future prospects. Thanks for the detailed summaries.

[Goose]

Nice, CG. Very nice. I hear Gander promised you flowers.....Goose

[VS]

I love you!I love this post! I love my ass!

xxxx

[remittance girl]

CG,

What a great, thoughtful, humorous HOW TO. Plus, I can't stress enough that, if you are feeling icky about doing it because of the "dirty" factor... the enema really helps make you feel a lot safer about that. We'll it did me, anyway.

Hugs,

rg

[chelsea girl]

Wow.

Gosh.

All's I'm trying to do is make the world a more pleasurable place, one anus at a time.

xxxxx to each and every one of you,
CG

[becky sue]

To some, you are evidently the Boddhisatva of Booty. But to me, you will always be the Fornication Fairy, showering the world with light, joy and Tushiesprinkles wherever you go.

[ben]

If I weren't quite smitten with you already, this series of posts would have done it.

Dayum.

So, you wanna come over and coach us? Make sure I remember all the steps? Blow a whistle and throw a flag if something goes awry? :)

I bet you'd be the best buttfucking coach in history!

[v]

whatever we know, we don't know enough. ty for the nuts and bolts.

[db]

My favourite way of prepping her for anal love is to shower with her. Let my hands slide all over her.

Washing her.

Taking her to the bedroom.

And licking her. Letting my togue slide over it lightly. Probing just a little bit.

In no time, she's begging for it.

And of course - I'm more than happy to give a woman what she wants.

[chelsea girl]

Gentlemen,

Thank you all for your love and attention, and your love at attention, and your loving attention, and your attenuated lovin'.

And so forth.

And DB, I'm guessing from reading both your comments and your blog that you have progressed far beyond anything I could possibly presume to teach you and yours.

So kudos to you and your beloved.

And Becky Sue, "tushiesprinkles" might be my new favorite ice cream topping, you know, after rainbow jimmies.

Cheers,
CG

[schuey]

"It takes an almost metaphysical level of openness to find pleasure in that acceptance"

That is beautiful indeed. I'm not a big fan of "sex" blogs, but yours is very different, emotional.