February 18, 2006 4:50 PM   Subscribe

[SexFilter] After much bruising, my boyfriend and I would like to try again.

After trying a few times, we've been unsuccessful in anal sex (It's my first time trying with anyone). Usually it leaves me in intense pain and bruised. I'm usually the one leading the action, often in a "doggystyle" position, and very plentiful with the use of Astroglide. What are we doing wrong? What hints/positions/techniques are known to work? I'm female, by the way.

Anon because I didn't know if it was appropriate. If you prefer to also be anon with responses, e-mail me at kalatamahara AT hotmail DOT com.
posted by anonymous to Human Relations (26 answers total) 3 users marked this as a favorite

I would suggest that anything which leaves you in intense pain and bruised is not worth pursuing.
posted by A189Nut at 4:58 PM on February 18, 2006

I'm going to assume that his penis isn't enormous. If it is, good luck.

Here's the trick: get your boyfriend to finger your ass first. Start with a well-lubricated single finger. Go slowly. When you can handle the single finger without any discomfort, add a second finger. Keep adding fingers until the width approximately equals that of his cock. Once you can handle the fingers without discomfort, try the actual intercourse.

The work-up process should take a while. This isn't a race, take your damn time... this is about getting you used to having something up there.
posted by Netzapper at 5:03 PM on February 18, 2006

Netzapper said it before I could. This is something you need to work your way up to with fingers first. Take your time and use a lot of lube. It's worth the effort, IMO.
posted by Meredith at 5:12 PM on February 18, 2006

Pick up some analgesic lube if you can find it -- sex shops often have the stuff, like "Anal-Eeez" or names like that.

Try this out: Lie on your sides, spoon-style, with him behind you. Lube up. Have him start by just pushing the tip of his penis against your anus, using a steady semi-quick rhythm, just as if you were fucking normally. He shouldn't try to insert it right away, just push the tip against the hole for a while, keeping the rhythm steady. When you're relaxed enough, he can start to push the tip inside, but still keeping the semi-quick rhythm -- if he slows the rhythm, you may find yourself anticipating how much it's going to hurt and you'll tense up and clench, which'll make it hurt. Have him fuck you like this for a while, with just the tip going in and out, steady rhythm, no stopping or slowing down. After you're relaxed enough with that, he can push it in a little further, and so on in that fashion until he's all the way in. Eventually you're much more relaxed with the whole thing and you can try different positions and speeds.

This may not work for everyone, but I've found it pretty effective in the past.
posted by Gator at 5:17 PM on February 18, 2006

There are probably good reasons not to do this -- blocking pain doesn't prevent tearing and injury --, but the first time I tried ass-fucking a gf, a female mutual friend of ours suggested, based on her own experience, that my gf get very drunk before hand. My gf did, and it worked, but she did complain of pain for the next week or so.
posted by orthogonality at 5:27 PM on February 18, 2006

Pick up some analgesic lube if you can find it -- sex shops often have the stuff, like "Anal-Eeez" or names like that.

This is absolutely the worst idea imaginable. Pain is a signal from your body. The signal says "you are injuring yourself". Ignore your body at your peril.

You can enjoy anal sex, if your partner is patient with you. It doesn't hurt if you do it right. But you do have to ask him to be patient and go at your pace, not his.
posted by evariste at 5:49 PM on February 18, 2006

This can be quite difficult for beginners, particularly since in a doggystyle position you tend to put pressure on the very muscles which, if not relaxed, will cause you pain - so in that position be mindful of how you're holding your ass.

If you're both beginners, maybe it's too much to expect that you're both going to get it right, so perhaps you should take the lead, you on top/ him on his back, and ease yourself down onto him. That way you can learn for yourself the pace at which you need to go, and then be in a better position to inform him of what you need him to do when you try it doggystyle.
posted by forallmankind at 6:10 PM on February 18, 2006

Go slower. Much slower. Relax more. A lot more. Lubrication is important, but it's not sufficient by itself. Work your way from touching, to fingering, to intercourse.

Read the Anal Sex HOWTO.

And good for you, sharing this experience with him and patiently trying to do it well. You're clearly a great girlfriend!
posted by majick at 6:14 PM on February 18, 2006

A little bird told me that doggie style is among the *worst* positions for n00bs to try. A variant of the missionary position is apparantly one of the easier ones.

And no, 'anal-eez' is not the worst idea imaginable. That's why they make the stuff.

relaxation is key, though.
posted by drstein at 6:20 PM on February 18, 2006

It would not hurt to peruse The Great Ass-Fuck Conspiracy.
posted by stet at 6:26 PM on February 18, 2006

God, I can't believe I'm not blushing, but as a female fan of the ol' backdoor howdy, here's my thoughts:

Sloooow. You won't be able to cram it in there as soon as you slick his penis up, you have to ease the sphincter open. Really, think of your bum as a muscle, you want to do prep work and warm up first right? Otherwise you'd get a muscle cramp (or a busted asshole). So, fingers, 1, 2, 3 (make sure his nails are trimmed and smooth!), scissoring motion combined with a nice in and out. Butt plugs and slender dildos might be good toys to look into. Analingus would also be sensual and make you more at ease. Foreplay is essential before the buggering.

Second, any position where he can get in deep is probably not good til you get a handle on how your body works. I freaked the first time it went "too deep", which you can do, and guess what, you're dealing with tissue that's more delicate than your vagina. Spooning is good.

Lube! Water-based, no anal-eez or whatever evil BS product you come across (heh). You want something that'll stay wet and slick and not dry up. Also, condoms to take care of that "not so fresh feeling" you might sometimes have, unless you've incorporated enemas as part of your prep.

Lastly, please research as much as possible before you attempt again. Don't be that clueless chick that winds up in the emergency room because she and her boyfriend didn't know what they were doing.

Good luck, and happy butt-fucking.

P.S. Rent bend Over Boyfriend. What's good for the gander is good for the goose.
posted by lychee at 6:47 PM on February 18, 2006

whoops - how could I forget? puckerup.com
posted by forallmankind at 7:08 PM on February 18, 2006

the two keys words here are "SLOW" and "talking".

the finger method works great generally. Its how i got it all to work with my first girlfriend. This latest girl however finds the wrinkled nuckle skin too irritating so i usually just put the penis right in. Lots of lube. Just pushing at the brown button at first untill she is more turned on and relaxed. Then just the head. Talking the whole time - make him take his cues from you. when you're ready for him to try going a little deeper, let him know. Make sure he knows this is your tender hole so you get to be in charge.

also, i was hoping i could work in the phrase "kicking in the brown door and painting it white on the way out" to my answer, but couldn't :T
posted by Tryptophan-5ht at 7:37 PM on February 18, 2006

What's the pain like?

If it's bruising pain or really unbearable, you're starting too fast.

If it's burning, switch the lube you're using. If you're not worried about safer sex, try an oil-based lube. Crisco is the subject of many jokes but it's actually awesome.

Anyway the number one trick for anal sex that no one ever tells you is PUSH OUT. yes, like you're trying to shit. it sounds counterintuitive, but it completely relaxes the first sphincter in your ass. You won't shit -- you shit beforehand, right? You don't have to really bear down, and with practice you'll learn to isolate that muscle so you can relax without thinking about it that way.

Also, when he starts in with the first finger, it's better to start pressing the hole with the pad of your finger and then "tip" the finger in, rather than starting with the pointy tip of the finger. pointy things poking at your hole with make your hole snap shut pretty fast. it's much better to rub around, increase pressure, and just let it slip in when it's ready.

Position suggestions: I agree with spoons, because it allows both people to stay still and move when they want. Another good position would be your ass at the edge of the bed with your legs up, and him just walking up to your ass. Although I would really suggest practicing with toys first (not neccesarily alone!), since toys have no secondary motives to get it in there more quickly than you're comfortable with. He may not be able to (or want to!) keep it up for 15 minutes of 1/4"-at-a-time with breaks for breathing.

<3 anal <3
posted by crabintheocean at 8:34 PM on February 18, 2006

Doggy style is the worst position to start with. And advice from a gay friend: Start with more lube than you think you're going to need, then add even more.

Oh, and you might like to use a vibrator during. Takes some of the edge off. (Though a doctor at a cocktail party once advised against that, as vaginal stimulation can lead to what he called "anal winking.")
posted by klangklangston at 8:36 PM on February 18, 2006

I am female, and my b/f and I have done this, and the only time we ever seemed to manage penile penetration into the anus was via intense sexual arousal and especially through vaginal stimulation. I think if you stimulate the vagina - something you're used to (familiarity) - it makes you more relaxed and enables your muscles to relax better, causing less pain. If you're putting too much pressure focused on anal penetration, it will make you tense up. Also, that time I believe he stimulated the anal/perineum area for quite some time (helping muscles to relax in that area) before penile penetration. The intense arousal seems to help in that if you feel intense desire, it's almost like your body conforms to your desire. So in other words, from my experience, you have to feel literally hot and almost sweaty as if your sheer hotness of intense arousal is elevating your temperature, and a sensation I would call "burning desire," like a "deep hunger" for it, lol... to turn it into a romance novel here.

Inevitably we have to begin with fingers though. The penis is way too big to start out with... unless your anus is exceptionally large or elastic (hehe, or unless your boyfriend is exceptionally small :P )

Also, I hate to suggest substances as a crutch... but a little beer and marijuana can go a long, long way....
posted by mojabunni at 8:47 PM on February 18, 2006

Lol. My boyfriend said he wanted me to say "We've tried this but it never works because my boyfriend is really, really big."
posted by mojabunni at 8:49 PM on February 18, 2006

1) It can take more time than you can possibly imagine. It's a project for a whole evening, and there are going to be plenty of funny moments, so prepared to be silly and relaxed. Maybe open a bottle of wine, if you like that sort of thing.

2) Get a really big pile of pillows and do whatever it takes to prop yourselves up very comfortably on your sides. After all, you're going to be there for a long time.

3) Some people find toys very helpful.

4) You might eventually decide it just isn't for you. That's ok too.
posted by tangerine at 9:02 PM on February 18, 2006

It's a project for a whole evening,

Are you kidding? Never... not even when I lost my anal virginity to a man with a 10" penis has it taken me more than half an hour to get warmed up. The same is true for everybody I've ever assfucked. It might well take longer--I'm not arguing that--but I can't imagine this being an all-night sort of thing. That said, it certainly shouldn't be planned as a quickie.

A good beginning position is with you lying down flat on your stomach, him above you. However, if your boyfriend listens to you (and he does, right?) then I would argue that doggy-style is not actually such a big deal. Just talk to him the whole time; tell him how you're doing.

Also, make sure you've taken a shit recently. Nobody, including your boyfriend (and excepting the folks whose kink is scat), wants shit on their dick. Similarly, a rubber might not be a bad idea. At the very least, make sure he takes a piss immediately afterward--the number of men I know who've gotten UTIs from ass sex is staggering.

Oh, and rub your clit while this whole thing is going on. You may find that you like it in the ass enough to drop the self-gratification, but it definitely makes it easier to get accustomed to the sensation.
posted by Netzapper at 12:04 AM on February 19, 2006

drstein: Tristan vehemently disagrees (thanks forallmankind)
posted by evariste at 2:50 AM on February 19, 2006

an commenter who wanted to remain anonymous sent this email. This is not from me though I agree with most of the advice.

Saw your post on askmefi and I wasn't comfortable with posting this publically. First off, in my (relatively limited, rather recent) experience, anal sex does take some getting used to. It can be rather uncomfortable at first, but it shouldn't be to the degree of intense pain and bruising. I would take that as a sign that you're going too fast.

It sounds like you've already discovered that going from zero to ass-fucking doesn't work for you, most likely because your boyfriend is too big to take in comfortably. Perfectly normal. The bruising is probably because you're not used to (how can I say this?) the pounding.

Instead, try starting out with a small, well-lubricated toy. Most importantly, make sure you're relaxed and *very aroused*. I'm not sure what relaxed involves for you, but I found that pot intensifies sensation in a negative way when it comes to ass play. A glass of wine or a cocktail works well for me though, obviously YMMV. Just don't get so wasted that your pain receptors are dulled. You want to be very aware of pain, because it's your body's way of telling you that you need to make adjustments. (This is why I think analgesic lube is a very bad idea) It probably goes without saying, that if you experience intense pain, stop and try again another time.

Being very aroused really helps the process along. One of the best ideas my partner ever had was to insert a small butt plug just as I was going to orgasm. *whew!* My only previous experience was with a very clumsy ex and I was pretty skeptical about enjoying anal - I can say now that I'm a fan.

The main idea is to work your way up in size, and avoid anything too large (Work your way up from rubbing outside, to inserting fingers, progressing to small toys, then larger toys, and finally The Penis. This could easily take months. Enjoy the process!) avoid a lot of friction, at first (working up to insertion is all well and good, but make sure you *also* give yourself time to get used to in and out. Lube is your very best friend) and avoid doing anything for too long a period of time. That way lies cramps, and you don't want to go there.

The only other thing I can think of is to be careful and go slow when removing toys - if you go too fast, it tends to cause an uncomfortable 'burny' kind of pain which isn't very fun at all. Your instincts on leading the action are dead on - good on you for trying again. Believe it or not, it's worth it!

By the way, I'm a girl if it helps. Good luck!
posted by jessamyn at 7:00 AM on February 19, 2006

For what it may be worth, my experience with analgesic lube has been that it's fairly mild stuff, and won't totally numb the ass or mask severe pain, or tearing, or anything serious like that. It's just something to help ease the buttsexee into the buttsex, and certainly no worse than a couple glasses of wine to help take the edge off the initial discomfort. One's mileage may vary, of course.
posted by Gator at 8:28 AM on February 19, 2006

Go to tinynibbles.com Violet strongly advises AGAINST any anal-eeze. All it does is mask pain that is your body telling you something is wrong! Don't use anything like this product!
posted by 6:1 at 10:57 AM on February 19, 2006

"drstein: Tristan vehemently disagrees (thanks forallmankind)
posted by evariste at 2:50 AM PST on February 19 [!]"

Yeah, I read that.. but it seems that there are others that say it works just fine. Six of one, half dozen of the other.
posted by drstein at 2:00 PM on February 19, 2006

I don't have any experience in this area, but found the thread intriguing, and Just to respond to netzapper - DEFINITELY wear a condom. Yipes.
posted by radioamy at 10:49 PM on February 19, 2006

The first girl I tried this with couldn't take it. We ended up going to a sex shop and buying this thing called an "anal training kit". It contained three butt plugs of varying sizes. We worked up to the largest size over the course of a week (the largest was just smaller than my own girth) and from there it was, with judicious use of lube, smooth sailing.
posted by cactus at 3:53 AM on February 20, 2006

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