Two newbies & anal sex:

Cuba

My girlfriend and I have decided that we would like to get into anal sex. With her being the recipient, of course. She has never engaged in said sexual act, so it's new for the both of us.

Off the top of my head, I know that this is something that we have to ease into; as in, I am not going to "surpirse" her one night, and just go for it. I can also imagine that I would want to use a lot of lube, especially the water-based kind, like Astro Glide.

We can obviously just Google this and read what we find that way, but I am interested in hearing what other people, who have actually gone through these beginning stages, have to say.

Thanks in advance for the help!

mime

I think you've got the basics, make sure shes ready, lots of water based lube, and unless shes on some other sort of birth control and you're certain of your std situation, use a condom. And I'd hit up google anyway, theres a FAQ floating around on some newsgroup that was pretty helpful to me.

Al_wat

I think the more "turned on" she is, the easier it will be as well. A big part of going in the A-hole is being able to relax about it, it helps if shes really horny from foreplay.

EggyToast

I have no interest in the act so I don't have any firsthand experience, but reading enough savage love makes it seem that there are 3 important things. In order of importance:

1) Lube
2) a plug
3) fasting for a day beforehand.

Lube is important because the anus is not self-lubricating like a vagina. A plug is important, even for a short while, so that she can relax and get used to having something placed in her anus. And fasting for a day should allow her to excrete any fecal matter hanging around, which should reduce her desire to defecate and make the experience cleaner overall.

It's somewhat glorified in pornography, but it's not exactly easy or always pleasant in real life. if you stick to the 3 points above, you should both be able to enjoy it without any unpleasant surprises.

PirateJon

Enema's.

or you could find yourself in deep shit.

FirstComradeStalin

Consider using an enema, to prevent any surprises.

Edit: Beat'd

KalTorak

I'm told (by gay guys, so your situation might be slightly different) that a condom is pretty much essential, even if you're not worried about STDs; the smoothness will help you out and help guard against hurting her.

Marathon

Condoms are a good idea even for heterosexuals. Your digestive tract is basically a long tube filled with bacteria.

xizoesira

Yes, bacteria. Be careful if you want to switch back to the vagina in the same session, as it really doesn't appreciate those bacteria.

Cryogen

Yes, wash thoroughly if you plan on switching holes, in either direction.

Tips for her :

It will probably be easiest if she's on her side, and you're behind her, spooning her as it were. She'll need to relax her sphincter. Its a similar technique as pushing outwards gently like you were going to take a shit. (this is also why its important she doesnt need to do that ) If this is something she really wants to do, it may pay for her to buy a small plug and just try having it in for longer and longer periods of time until shes fairly comfortable with having something in her ass.

For you, its already been said. Plenty of lube, condom, go really slow. Make certain you obey her EVERY instruction, she needs to be in control of this. And if she says pull out, do it. It will probably be VERY uncomfortable for her at first.

Also, its interesting you say "with her being the recipient, of course". It can be a very pleasurable experience for guys, as well. But you have to be into it of course, enjoying it doesnt 'make you gay' (well, unless its someones penis :P ) but like any sensation not everyone likes it.

UncleChet

a few things that may help. Try just finger play for the first couple of sessions. This gets her to realize if she likes butt play or not. You may want to get latex gloves though, cause fingernails wil fuck shit up. If after a few sessions, you can pleasantly work 2 or 3 fingers in there, and it's not too much stress for her, you'll be all set. Also, if she controlls the pace, it'll likely go easier for her. Have her stradle you and lower her self onto it, I think if she has the penetration control it'll go a lot easier and smoother. Also, enema's are a good before hand and LOTS of Lube (astroglide cleans up well, just don't use anything warming), and condoms can really help with clean up as well.

MuddBudd

they sell desensitizing gel for this as well.

supabeast

Advice from a man who can take sex toys the size of beer cans:

1. Cut your fingernails first.
2. Enemas are helpful, but unless the bottom has bowl problems just taking a dump first usually cleans everything out.
3. People with irritable bowel syndrome should never, ever, bottom.
4. Use a generous amount of lube. Get a pump bottle and just shoot a big blob right up in there.
5. Don’t overdo it on the lube, or the bottom will be shitting it out for days.
6. The chemicals used on many condoms with irritate the anus. If you use condoms for anal, get unlubricated condoms and lube it yourself.
7. Start with toys. Do NOT just shove your dick right up in there.
8. The faster you can get it in, the less it will hurt. This is because the sphincter will loosen up once there’s something jammed in an inch or two beyond it, but contracts around anything until then.
9. For God’s sake, do NOT use painkillers/booze/drugs to kill the pain while doing anal. That will just lead to extra damage. The same goes for desensitizing lube—that stuff is for people who want to take massive objects, not beginners.

You might also want to try working some toys up your own ass. This will reassure her that you’re not just some evil man planning to rip her anus apart and leave her to die. It will also give you killer orgasms.

Fantasma

The use of enemas have a nasty side effect, if you abuse of them, the motility of the colon could be lost.

By the way, unprotected anal sex can cause fungus infections on the penis (Glans), which is difficult to cure.

apotheos

You need to be having frequent enemas for it to become a problem.

Starting with toys is the best idea, working up towards diameters the size of your penis. If done properly it will not hurt at all, it will just be uncomfortable at first. With practice that goes away.

The best way to penetrate her for the first time is something I learned from Dan Savage: lie your fucking ass down and don't even think of fucking moving. She is 100% in control.