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The Anal Data Sheet

The Anal Data Sheet

I PMed Stalin a couple of days asking this question, but I thought I'd bring it here as well.

Can any of the guys that have tried anal sex with a condom tell me anything I may need to know?

The reason I ask is because I've never even successfully put the head of my dick in a woman's ass because the times I've tried there was lots of bleeding or she jerked away and wouldn't let me.

I should be having my first anal experience with a girl I'm seeing now and she is new to anal as well.

I want to use a condom for several reasons.

If I really lube up her asshole and the condom extremely well will I be able to get in there without the condom ripping/breaking or being pulled off once inside? I have no idea how tight a woman's asshole is, and if like many people say it is tighter than any pussy, that is a little worrying because I've had some women with super tight grips vaginally speaking.
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