Verified answer

Do your research, my dear dear friend. Lubricate. VERY WELL. Plenty of KY. Prepare before you Penetrate, and above all... -CONDOM!!- If it's not done right, and with a great deal of consideration on both your parts, it -WILL- hurt... and you can do serious damage. Embarrassing emergency room damage that could take the pleasure away from you forever. Think heavily on what you would tell the ER doctor sewing up your bum. :)

There are plenty of books in the Sexuality section of local bookstores. Read up on them. There is a beautiful book called "Anal Sex for Women" That is probably the most informative one I've read yet, but there should be -something- either in your bookstores, or in the library. Make sure _HE_ reads them, too.

Don't give in to his pressures, or the pressures of your peers if you are not ready. It's a big step, and it takes preparation. It's not something you can just bend over and do. or -SHOULD- just bend over and do.

Remember that you can contract sexually transmitted diseases... some as non-serious as crabs... others life-threatening, like AIDS.

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It can if you are not careful.

Go to an Adult store or website like adam&eve.com, and buy some Anal Lube. It has a slight numbing effect on the anus, and then try some toys so you know what is going on.

Also, don't forget condoms, and then read up on anal sex like at websites like ivillage.com.

Just be sure you both go slow and easy and have fun.

It's a good sign that you're concerned about him !! Yes, use a proper anal lube and take your time: lots of foreplay to get him ready, ease it in very slowly so he can be accustomed to it. Even when you are all the way in, he will be dealing with new sensations: he'll feel "full", feel like he has to go to the bathroom (when he doesn't) and things that may feel like discomfort until he gets to like them. But it absolutely doesn't have to hurt. My first time was great - yeah, some things to get used to but my Top was very patient and considerate and I sure didn't want him to stop !!!! It will all come naturally to you and will be something you both remember . . . . Enjoy !!!!

First penetration will hurt some, but just have him go slow and easy use plenty of spit or lube if that's your thing, lube takes some effects away I think! But it also depends on his size but given a slow approach and maybe some lube their isn't a man out there I couldn't ride! But this is about you so I've known a few guys that just can't relax enough to have a good time! So go slow, have him tongue it and make it slimy, relax, have him slide in once part way then stop for a second then pull out, let your body re relax and you should be ready for the feelings I can't get enough of!

the 1st time for me didn't hurt as my bf at the time was very understanding took things slowly and used allot of lube and fingering. if he really likes you and you explain your worries he should be understanding and take things easy

no more that straight anal sex does. lol

truth is if your well prepared and the toping guy is skilled enough it dont hurt. sometimes it does if ur not using right equiptment eg lube and the guys ablity to aim makes you thankful he dont play darts. thats what makes it hurt or not, in my experience a massive penis from someone who nos wot to do dont hurt compared to a normal sized one that is crap!

Duno yet, I want to know too, thanks for asking that question :)

I know he wants to do that too, its his body language or, erm, bum language.

I know he knows that I want it too, cause I sort of go nuts when he licks & fingers me & I, em, squirt buckets. He sort of whimpers when I do the same to him but I think he s too embarressed to say how much he s gagging for it :)

Sorry I cant really say what its like & I dont mean to be rude. I guess im in the same boat as you, Hungry??

My b-f, I can trust to be carefull & gentle, make sure your b-f is going to be carefull & gentle with you. :)) David

Oh yea guys thanks for the good answers & for the bad answers from the homophobes, go stick a rocket up there, its the only bang your ever likely to get!!

Only if you rush it and don't use enough lube. Take it slowly at first, and make sure to lube up both the penis and the entrance to the anus before you start.

i can tell from experience that the first couple of times yeah it'll hurt but then you'll get used to it, and depending on your partner make sure they take it real slow