Alright, my girlfriend and I have had anal sex probably about 4 or 5 times, and usually she doesn't like it much, but this last time, she said it wasn't that bad. She may have been saying it just to make me feel less guilty, but I don't really know. Knowing all this, what are the chances that if we keep going with it she'll start to like it better?

At least she shut up about it. In my experience, anal isnt worth listening to them bitch about it the whole time.

Although, I tried it one time with my current partner. And she just whimpered softly the whole time. It was very sexy.

Yeah she usually does stuff like bite the pillow and things, but I know it's out of more pain than pleasure, and ultimately I'd like it to be something we both enjoy

Theres nothing wrong with her being in pain.

But my last partner would whine about it the whole time "ehhh, it's just wierd. ughh" in a real whiny voice.

I find that vaginal sex improves if we use astroglide.

What position are you usually doing? You should warm up her asshole a bit before intercourse. Just stick one finger and make circles inside with it. Lube would be great since it reduces friction of course.

I did anal with my exgirlfriend just once and she really enjoyed it. She had a great orgasm while I fucked her anus and she touched her clit.

Oh yeah, well I'm definitely a proponent of Pain + Pleasure, but I love this girl quite a bit, and I don't want to really hurt her bad, but a little pain on her side doesn't mind me. Ultimately I'd want her to not mind it.

EDIT: Oh yeah, I use lots of lube, and I do need to warm her up a little more probably, but we usually do it in doggy, but I've heard it's better to start in missionary

Buttsecks takes some time to get used to, so it may very well be that she'll like it much better after a few more times.

If you take things slow and are very considerate then it will work ok. Ask her to move toward you at first.

Owwww!!! Doggy the first times!

Well there you go. Try the spooning position. Her rectum and anus will be relaxed and that gives you BOTH control. I PROMISE you she'll be grinding AGAINST YOU.

Oh and lightly rub her clit, of course. That helps.

Anal sex is disgusting, think about it, you wouldn't want her shoving stuff up your butt.

I propose a pegging experiment to verify.

Speak for yourself.

Speak for yourself.

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What?

I suggest doing it in the missionary position with her legs back as far as possible. Then start by making quick small thrusts and as the resistence fades push in further and further. If you go to slow it pulls, to large of thrusts off the bat and she'll cramp. Once you get going you can make larger thrusts. I suggest angling your penis in an upward angle towards the pelvic bone to hit her G-spot. It will take a few times for her ass muscles to stretch out, kind of like working up to the splits. Start with just of minute or two of anal, and then start going longer with each session. You can also get butt plugs to help stretch the sphyncter muscle. She'll really moan if you get a vibrating one and fuck her pussy while it's in her ass. To make her feel more comfortable, let her finger your ass to rub your prostate or use the butt plug too. Nobody will know unless you tell people.

http://i33.photobucket.com/albums/d62/Sailort174/peniswhere.jpg

Ok, that said:

Spooning the best way to start, for her. More control, more relaxed, less pain. Lots of lube, LOTS. Start with a finger, work up to 2, keep her relaxed and LUBED.

thats like saying "vaginal sex is disgusting, think about it, would you want her shoving stuff up your urethra.