Your ass will take a very small object (a lubed finger or very very small
dildo)
without actually relaxing. You can play around back there and it never actually unclenches, but it doesn't hurt because a finger is small enough to just slip in.
With anything larger than a couple of fingers, maybe your friend's erection for example, or a
dildo the size of a banana or bigger, you aren't going to get anywhere without the cooperation of your sphincter. Next time you have a finger up there, give your finger a squeeze - that is the area we're talking about. You can squeeze because you have a sphincter under your direct control.
But immediately behind that is another one that you can't just relax when you want it to. (sorry if you already know this anatomy lesson but it is worth saying) This muscle has final say over whether you get to experience the pleasure of anal sex.
Yes, it has a mind of its own. Yes, it has the power to make or break your evening of pleasure. Until it decides to relax, nothing you just jam in there will feel like pleasure. It will feel like your ass has a stomach ache and road rash at the same time.
So, to avoid that, you have to get it to relax.
What works for me is to take a good-sized
dildo lubed up, and apply a little steady pressure. It doesn't even have to really go in. Just push till it stops. Go to the point at which if you pushed any more it would feel bad. Just hold it at that point. Don't go overboard, because you will know it instantly. It is good to practise or prep with a
dildo but my bf can just do the same thing and wait at that point..
With
gentle but constant pressure, your ass will go from saying "no", to "undecided", to "okay, maybe", to "hell yeah give me more." You can feel the moment it finally gives in and decides to go for it. It actually kind of quivers a bit.
Once it gives in, it is absolutely comfortable, there is no discomfort you have to put up with, and you aren't forcing anything. It just finally is ready for sex and it lets it happen. You don't have to put up with pain or "just get used to it." When things are ready to go, it really is total pleasure.
Sometimes though it just doesn't want to give in. Don't push it. It is a lot easier to stay hard when you aren't shoving something up your ass when it isn't in the mood. Often I can try again a half hour later and all is well. Once in a long while, it just doesn't want to go that night. So, there are a million other things to do in bed. Also, the nice part about two guys is you can switch up, or at least that works for my guy and me.
By the way as far as cleanliness, you don't have to make a chart or anything but start paying attention to when you usually go to the bathroom. That is probably not the best time to do anything anal, but maybe an hour after the fact would be no problem. Because of how the body works, a man's ass is free for fun and games most of the time. But trying something when you are usually about to go to the bathroom is asking for trouble.
As far as stretching things out of control, you should never feel pain. If so you have gone overboard. The only thing I have felt is a bit of weird pressure while I wait for things to relax. But nothing overwhelming or worrying. Everything should tighten up just fine once you're done. I've got some fun toys in assorted sizes (nothing too freaky) and a rather large boyfriend to be honest, for 10 years, and everything works just fine.
