Holy painful anal...advice?

Contributor: ShadowedSeductress ShadowedSeductress
We have tried anal sex a few times before and it was painful. We prepped a lot more this time, and used a toy that was close to the size of his penis. I was relaxed and we were both well lubed. It was still super painful.

He was gentle and patient. Managed to get his whole penis in but it was too much so he pulled out some. It wasn't painful when he had the head in and it actually started feeling kind of good!

Problem is he's one of the guys who's head is smaller than the shaft of his penis. I honestly don't know what to do. I don't see how we could possibly prepare more than we did! I mean it was bad. It was painful to the point of making me cry a little when he was all the way in.

Any advice?
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Contributor: Mwar Mwar
Sometimes having an orgasm before hand or having a vibe on your clitoris will help, along with the lube, time and relaxation you are doing.

Good luck!
Contributor: - Kira - - Kira -
I have the same problem. I'll prep for hours beforehand and use enough lube to kill someone and it still hurts. I was given the advice to bear down upon insertion, but I've been too nervous to try that out.
Contributor: Kdlips Kdlips
wow it good for me no pain
Contributor: Nora29714 Nora29714
Originally posted by Mwar
Sometimes having an orgasm before hand or having a vibe on your clitoris will help, along with the lube, time and relaxation you are doing.

Good luck!
I agree
Contributor: tami tami
I am with you it HURTS!!! it is very painful and I am not doing it ever again..I did cry and hubby felt so bad that he said he would never ask again. Even if he does ask the answer is a firm HELL NO.
Contributor: Dixiemomma Dixiemomma
just prep work and a lot of lube... helps if you're relaxed too tho, if you tense up even once it's over!! might not be something you ever get used to and he might just have to understand, sounds like you're really tryin hard to make it work tho
Contributor: ScottA ScottA
If you want to do this you'll need to keep going slow. Since the tip started feeling good, try this a few times without putting any more of his penis in.

Later, when and if you're completely comfortable, you can try putting a little more in. It might be a good idea to do something else sexual first so he isn't quite as eager to go.