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First Time Anal Sex

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I've been seeing this guy for a while, and a few months ago he mentioned that he wanted to try anal. We didn't have lube or anything, but we were both pretty drunk, so we decided to try anyway. It hurt way too much to go through with it. He was really understanding about it though. He hasn't even brought it up since.
So, I want to surprise him and try again. I'm going to buy lube and everything. Is there a type of lube that you can recomend? Also, is there anything else I should do in preperation to make sure its clean? I'm really paranoid about that.
Lurker
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My advice is to make sure you give yourself an enima before you do it so you are clean. Make sure you use a condom and plenty of water based lube. Also make sure you are relaxed and that there is plenty of foreplay with lots of touching and playing with your anus. His fingers should be used to enter you first to allow you to get used to it and loosen you up. I also recommend you trying to play with your own behind with your fingers or possibly a toy before you do anything with him. The cleaner, more relaxed, and more foreplay involved before actual penetration by his penis the more enjoyable it will be. Hope this helps and you enjoy!
Rookie Scribe
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Use lots of lube and if you insert a butt plug first and leave it in for a while first it will help you a lot...Good luck