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Anal

Not everybody is going to enjoy it. If somebody doesn't enjoy it - things will probably just tighten up even more. I'm just thinking out loud here - but if she says that she doesn't find it enjoyable, then that is probably a hint for you to abandon the idea altogether - and to concentrate your energy on something that she enjoys. 

We would recommend "Nina Hartley's Guide to Anal Sex" by Adam & Eve Productions.  Great informative DVD with anatomy,  a demo featuring Nina Hartley and Anna Malle, and group action featuring Nina Hartley, Anna Malle, Hank Armstrong, and John Decker.  Secrets of backdoor love from the best butt in the biz.  Erotic, yet filled with common sense.  Check it out.

lots of lube and trust. those are essential. though as the above posts mention, maybe it's not for her, focus on other stuff. if she is interested but just can't work through the pain then Deuces suggestion is a wonderful place to start. 

"You can only do this if you have the desire.  Your anus will always listen to your heart, not your mind." - Nina Hartley

Try stimulating the opening with just the tip of your finger or better yet your tongue. There are a ton of nerve endings there and it's a super sensitive place, go easy with no intention of penetration. She may respond and she may not, but ultimately it's her call.

for me it was different and slowly easier, it started when i was very young, in school like 14, too many boys teasing me about my butt...and in the end i gived in and was also curios and wanted...so from start was first 7 8 guys just finger and eating my butt

noo...i didnt do ..first 7 8 times with different guys

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Wow sexy picture damn.  

Stimulate the outside with a small vibrator  while using your mouth and other hand to pleasure other spots.. but don' put it In the first time. Like put the vibrator to the hole while sucking her nipple. Omg I luv that one lol. Eventually you wanna feel sometginh up there