What is the trick to having anal sex without pain?
Lubrication. Lubrication. Lubrication. Since there is no natural lubricant present in that…uh, orifice. This is the most important thing, in most people’s opinions.
Slowness. Take it veeeeeeeeery slow, and gradual. It might require as much as 10 minutes for the “receiver” to become fully comfortable.
Relaxation. The receiver must be relaxed, and comfortable.
No violent actions or moves by the giver. Just steady, slow, gentle actions.
…I dunno…I just love the fact that Anthracite answered this…
The person on the receiving end should be the one doing the moving. The person with the penis should hold still. I highly recommend the female on top, face to face position for the first time. If you push outward slightly, it will help relax the sphincter muscle.
Hey Sqrl, Matt, Esprix- looks like we’ve been doing it all wrong…
Now, don’t draw any conclusions from this. I know a bit about piercings too, although I’ve never had one…
Lubrication is important, as Anthracite mentioned–but so is muscle control in the reciever, especially if it’s someone who’s never done it before.
It most likely -will- hurt the first time, but the trick over time that you learn is to control the muscles more effectively in order to more easily accomodate your lover. It helps if you can get tease them and get them to ‘loosen’ up a little first–using whatever harmless methods your naughty mind conjures up.
After that–lubrication is of course a must. You should also use a condom.
If the reciever is a male–and they feel pain after being touched in the prostate–it’s usually a bad sign. They should have it checked by a licensed physician.
Also–a -tiny- bit of bleeding might be normal if it’s the first time. Remember–I said -tiny-.
Have fun.
-Ashley
There are lots of ways to have anal sex that is not painful and even more where it is positively orgasmic. Let’s see for a beginner, lube as mentioned helps. I prefer KY Jelly as it tends not to dry up as fast as the more watery lubes out there. Also, if you need more it is easier to clump more of that kind on rather than the water kinds.
Other things that deal with comfort are as follows: fullness of bowels, amount of lube, positions, relaxation, and the speed of your lover.
I will start with this, make sure you go potty a few hours before trying and it is a good thing if you aren’t sure if you are done to take an enema. They are available over the counter. Purge yourself for a nice clean experience. 
Also, it feels better if you don’t pack in the dirt into a tiny little space and have basically a free sliding tunnel of love in its place instead.
Next, positions. There are many positions that you can do it in. Most people think it must be done doggy style but this simply isn’t the case. I prefer either lying on my back or riding on top. My ex liked to bottom on his side or on his stomach. I find that the side allows for the least amount of penetration and that can be painful too because if the penis doesn’t pass the first sphincter it hurts. That is the real muscle you want to relax. Also, doggy style tends to be rougher generally speaking and the penis always feels like it goes in farther.
I already mentioned relaxation. You have to be ready to accept it. If you can take a big poo without it hurting then you should be able to bottom. If you tense up you won’t be able to accept it and if your partner tries to force him/herself you will get injured and having a butthole injury is not fun. Analingous also helps loosen up the outer anal sphincter and helps you to relax. Have your buddy try it out with you before hand. If done properly (and you are clean) it can also add a slight bit of extra lube.
Along the lines of relaxation when you are bottoming is the speed of your lover. You are the one who receives the pain if it isn’t done right generally speaking so go at your speed not his/hers (thinking of strap-ons and such). Go as fast or as slow as you like and you will be able to have a pleasurable experience.
Check out The Joys of Gay Sex or The Gay Kama Sutra for positioning advice and extra information about different lubes. Play safe and at your speed then you will have just added a nice skill to your sexual repertoire.
HUGS!
Sqrl
PS. One tends to be the most relaxed in the morning right before getting out of bed. If you get used to it then the evening/anytime romps can become a little easier.
HUGS!
Sqrl
Using the 3-finger method is good, too. To open up the anal sphincter muscle, massage it gently, first with one finger and plenty of lube. Then progress to two fingers, again going slowly and plenty of lube. Then finally 3 fingers and again, PLENTY of lube.
Take your time and don’t rush. This isn’t a race.
…and I love that someone by the screen name of poohpah chalupa responded in a thread about anal sex.
What Sqrl said. (Damn he’s good! Er, um, I mean, at explaining things like this! Stop that giggling! Stop it! Argh! ;))
Esprix
Well, it happened to me once.
Me and my boyfriend were showering and he just did the deed, without asking me.
It took me a minute to notice, so he must’ve been lubricated quite well, as I didn’t really feel anything.
I don’t see what you guys see in it, but to each his or her own.
Some women enjoy it, but see, men have this little thing called a prostate which, when stimulated properly, can result in mind-blowing orgasms. It is, in effect, the male g-spot. Women don’t have a prostate.
Esprix
Why am I always left out? Who do I have to blow to get on the Official SDMB Gay Guy List?
Definitely no compliment to the guy
That is because you are not a male. We have prostates that respond warmly and happily to anal stimulation. If Americans weren’t so sexually limited, straight guys could get in on the action with their girlfriends using anal beads or strap-ons.
Like the other posters wrote, the important factors are cleanliness and lots of lube.
sunrise,
I don’t have any firsthand experience with receiving that will help you out, but I’ve been on the giving end more than a few times and have taken note of what works out well. The best suggestion I can offer is digital stimulation of the genitals during the act. Whether you masturbate or your partner assists, this will help to relax the sphincter. This is particularly good when you achieve orgasm and repeated orgasms as the muscles in question will spasm and relax, allowing easy penetration. Also, anal penetration during orgasm has a tendency to prolong and enhance orgasm by controlling the extent to which the sphincter can spasm.
Realize, though, that not everyone can enjoy anal sex. It just might not be your style. Don’t ever push yourself to tolerate things that you don’t really enjoy. Sex is supposed to be fun for everyone involved. A good way to determine your own capacity to enjoy such things without over committing yourself is solo exploration. The insertion of a finger or vibrator during masturbation, particularly as you reach orgasm, will give you a good indication of how your body will react when you try it with a partner. Determine on your own how slowly you need to proceed, the best position, and your capacity for enjoyment before offering yourself up to a partner.
sunrise_4836, for you or your partner?
As the above person just said, its not for everyone. Try something else. Some people can bleed quite a bit & need to see the doctor. Some can bleed afterwards for a couple days.
Bleeding has been mentioned a few times. This is common, but should not be treated lightly or ignored. As there is a great quantity of very active bacteria in that region and the tissue is very delicate, infections can be a serious concern. A tiny tear of said tissue can develop into something frightening in short order. On the other hand, your butt is very good at repairing itself and does so frequently. Generally, you do not need to be concerned, but if you do notice bleeding, please use a topical antiseptic designed for treatment of delicate tissue.
It’s been implied in this thread that women cannot appreciate anal sex because there is no prostate to be stimulated. This is patently false and should be disregarded. There are women (I’ve known a few) who truly enjoy hot, slippery butt love more than life itself. At the same time, there are men, gay or not (I’ve known a few), who cannot tolerate even thinking too hard about receiving. The presence or absence of the prostate does not determine one’s capacity for the enjoyment of anal stimulation.
moo
Sorry of the hijack…
No offense, but goboy, this should be your new sig!
Sunrise_4836, you seem to ask quite a lot about sex related issues. Having a partner go slowly is always a must at first, and lubrication is key. If you’re not relaxed, it’s gonna hurt. This also goes with vaginal sex the first few times.