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Good luck, and dont give up! Its a wonderfully imtimate and pleasurable experience!
We've talked about this subject together alot and I had to weigh in on this one. You know my story, I finally tried anal about 7 -8 months ago now and I LOVE it with a capital L!
First I agree I dont think the kind of lube matters but the amount does. My guy is way thick, and we've found that there just is no such thing as too much lube. We use KY, I've found that the silcone ones and some of the other lubes meant for vaginal play (like Liquid Silk, etc.) can cause a burning feel in my tush. My opinion is the clear gel-type water based lubes are much easier on my insides so KY works great for me.
Second I agree with luvmybabies about the more you're turned on, the better anal feels and the easier it is to go hog-wild nuts and lose control and all those fun things. I have intense G-spot orgasms and we always start out with one of my my G-spot toys inside and buzzing away. It's not necessary for me to pop first but if I do he immedialtely can just slide his big boy right up there without the least resistance. It's a matter of my orgasm or even just being really hot and bothered super-relaxing my butt for him.
Next is positions. The missionary with my knees pulled back and a pillow under my lower back is wonderful. It lets him have a hot up close and personal view of my (can I say "pussy" here without getiing in trouble?") and my anal area. It also seems to be a perfect angle for him to go deep easily and he says watching it happen is better than any porn flick. Plus either of us can operate my g-spot toy easily at the same time.
Another great position for us is me laying on my side with my top leg forward and my bottom leg scissored back. He straddles my bottom leg and pulls my butt cheeks apart to get at my opening. This takes a little getting used to but he can go very slowly and easily in a little at a time while I'm warming up to him being in there.
Doggy style is good except I'm long legged and my butt is just a bit too high for him to push into when he's rock hard. We usually save this one for when I've laready cum 2-3 times and my butt is wide open and gaping, and it's his favorite for filling my tush with his cum load.
If you're having trouble getting to the going fast and hard and getting crazy part, try masturbating to orgasm with a toy while he's fingering your butt. Then like DevilDoll says, push outward a bit with your tush like you're on the toilet and relax your sphincters at the same time - he'll suddenly just pop right in like nothing. While he's starting his slow thrusts, work away at your clit or your g-spot and cum if you can...you'll open wide open then and the craziness can commence!
Another good lube, BTW - if your guy can pop more than once, a tush full of semen makes everything more slippery and fun...
Keep us posted, I love seeing other people enjoying this awesome kind of sex like I do!
Lisa

Hey Duckblind I tried Astroglide and for me it burns in my butt...not so with your gal? We still love it, though, it's the best for a slippery hand job (Liquid Silk is also great for that, but that burns in my tush too)
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