Stretching out your butt hole

Insightful breakdown of Anal Sex:

Straight guys and anal sex
I myself am bisexual and have enjoyed the wonders of receiving anal sex from both male and female partners for several years. But I've also known a...

Great introductory Anal toys?
My wife loves the feeling of my cock, fingers, or a vibrator on her ass. We've only had successful anal sex once, as the other three occasions were...

Okay....we have skirted around this issue in many polls. Straight to it now....IF you enjoy anal sex, is there part of it you DON'T like?
For those fans of anal, are there parts you DO like but others you don't...but are still a fan?

Did I make a mistake with this plug?
I enjoy anal sex, though it's something that I am not completely used to doing; an ex and I used to do it regularly, but it's something that the new..

Bigger penis = better anal orgasm?
I've always been fascinated with anal sex. By the time I began masturbating it was always anal sex porn that made me the horniest. When I finally got.

First thing first, if you are having pain, STOP!!! Anal play, no matter what kind, should not hurt. I would guess that since you are experiencing pain it is harder for you to relax, which is the key to anal play. You guys need to slow down and make sure that the anus is well stimulated before hand.

As far as toys go, find something that is the same size as your man. I recommend a dildo or vibe, a plug may work too but since the neck is smaller than the bulge it does not really help to stretch the anus. Once you find a toy the same size, work up to it slowly with other toys or fingers. Once you can get the dil/vibe in with no pain, then your man can get his fun, not until then.

Remember that pain is your body's way of telling you something is wrong, listen to your body, it knows what it's doing.

I agree wholeheartedly with everything that DWTim wrote.
I would however add that your husband should perhaps rim you before insertion. I've found this to really relax my partner and open her up, prior to intercourse.

The first two posters had it spot on. You need more playtime/warm up. Slow down, if it hurts then stop or slow down. It shouldn't hurt.

Anal play shouldn't cause pain. Anal play does create intense sensations, but you want to stop before pain.

A good lube, patience and a glass of wine will do wonders.

My goodness. I'm with the crowd, here. If it hurts, you're doing it wrong!

So, if what you were asking was "how do I warm up"---everybody seemed to answer you "For the love of everything sacred, warm up!" without giving you a lot of indication of how to do it.

So, here are my thoughts. When I was new to anal (young, still a virgin, etc), my very first toy was a hard plastic tube with a round end, I'd say it was similar to the Elodie, and I'd insert it on a pretty regular basis, probably every other night for a few years. It was easy because it was so firm, and the diameter was nothing challenging.

By the time anal sex first came up within the context of my relationship, I didn't need any warmup at all because I'd put in the "training" earlier. To this day, anything up to 1.25" and I won't need to warm up at all.

But, if I want to insert something bigger? Or if I know an anal session will be really rough and I want to make sure, in advance, that I can handle it? There are two things I'd suggest. First, you can stretch out with a tapered plug that goes to a size just a little larger than your partner's penis. Check out the Tantus Bronco, or something in a similar shape. Before your partner's even around, insert this a few times to loosen yourself up.

Another option is to use a plug with a thick neck, and wear it for an hour or so before sex. (You'll want to try that out without sex being planned, just to make sure it agrees with you, the first time). Maybe the Sexy Spades Small (I linked you Dwtim's review, because he talks about the neck a lot).

Hopefully one of those methods will get you stretched out in advance of your sessions with your husband. Good luck!

It should not hurt. Pain during anal can cause damage and is counterproductive (it makes you tense up more).

For all "normal" penises you really don't need to stretch. What you do need to do is relax, and that takes some learning. Because you have pain problems STOP AND GO BACK TO THE BEGINNING. Yes, I am yelling at you (sort of), but that's probably the only way that you'll ever have comfortable anal.

Start with a lubed finger (yours to start) around the outside of your anus. Get used to the sensations, start to enjoy them. Then slowly (think after a couple of days) move to penetration. Go in and out, around, stimulate the outside and penetrate again. Learn to enjoy this, that it can be pleasurable and does not mean pain is coming.

After about a week move to a small toy that's about an inch, or two fingers. Same thing, learn to enjoy it and learn to relax. Then about an inch and a quarter or and inch and a half. Enjoy, play with different positions, see what turns you on most.

At some point bring your partner into it. START BACK AT THE BEGINNING - you need to learn to trust him. Outside play for a while, single finger play, and so forth.

Eventually you'll be comfortable enough to go from a little warmup to a penis sized dildo on your own. Then it will be time to consider "full" penis-anal sex again, but make sure you can trust your partner to stop if you say so, and make sure you can trust yourself to say stop if it hurts.

i'd say a plug & lots of lube. and go slow

I would suggest successively larger plugs with an unbelievable amount of lube. Or a “stepped” plug with graduated sizes.
Link

I had the pain issue in the past which is why I hated anal sex. But I got the anal start (horrible material but great dildo) and I play with that, then another toy, and then him...and its pain free all the way.