End of the road for my anus?

I have a rather embarassing question but I really need help. When having anal sex with my boyfriend, after he inserts it and all it comes to a point where it is almost like it will NOT go any further. It's like his penis is hitting a wall of some sort and it really hurts. I am very relaxed before we start so the initial penetration is not a problem at all, it's just that there is something stopping his penis from going all the way in. what is causing this and what can I do about this?
Heather Corinna replies:

No need to be embarrassed!

Understand that the rectum is not a straight line, but is curved. It's not only curved, it's kind of curved twice: if the anatomy of your rectum from a side view was a map, we'd essentially go in from the anus, take a left, take a right, then go up again towards the right. So, what's possible is that your partner is hitting one of those walls, and either a) you two need to find a different position to have anal intercourse in or b) try using toys designed for the rectum for deeper anal play for you, rather than your boyfriend's penis.

Know, too, that the anus and rectum are pretty strong muscles that can have a good deal of clamp, so it may well be that you've simply reached the depth that is comfortable for you for now: just like with vaginal sex (and in some cases, more so) not everyone can have partnered intercourse where the penis is "all the way in" to its base, so the expectation that that's always possible with every penis, every vagina or every anus/rectum isn't so sound. Too, most people need to take a long time to introduce anal entry pretty gradually, taking baby steps with given sessions: if you're going to do this, I suggest stopping the depth of entry BEFORE a point where you experience pain (or if you get to pain already, then just have your partner pull back a little and stick to a level that is comfortable and enjoyable for you) and working with that for a few sessions before trying for more depth.

Are you introducing anal entry VERY gradually? Is your partner able to be pretty patient with this? The way the anus works, it tends to respond poorly to things being pushed into it, and instead, usually responds better when whatever you're introducing to it is pressed against the anus until the anus makes an inward pull, pulling it in. With a penis, toy or finger, it's pretty easy for the person who isn't the receptive partner to feel that pulling if they're being slow, patient, and paying close attention. Sometimes, if the receptive partner is the one in control of entry -- by taking a position on top where they can control the depth or speed of insertion, or by being the one to press back if you're on your knees -- rather than your partner pressing forward, it can be easier to suss that out and also to experience pleasure, rather than pain.

Too, are you using plenty of lubricant? That's really key with anal sex of any sort (as is also using a condom, but you may know that already), since the anus and rectum -- unlike the vagina -- don't produce any lubrication of their own.

Lastly -- and this is hopefully obvious -- that muscle relaxing also has to do with you being aroused and enjoying what you're doing: feeling really good, rather than just avoiding pain. So in the case that the anal sex you're having -- or any anal sex -- isn't what YOU want to be doing and doesn't feel wicked good for you, that may well be the biggest issue right there, and in the case that it's really not, then the answer is just to decline that activity, just as any person would delcine any activity that just isn't their thing or which doesn't feel good.

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