Painful anal sex

67% Normal
5 Comments

There is this girl that I am good friends with, in fact I think of her as my little sister. We have been intimate in the past, we had a threesome couple of times with her and my ex-friend of 12 + years; that is a whole different story, however. Going back what I mentioned earlier, we have great trust in each other. She is very comfortable with me and I with her, sexually and otherwise. Now she has a different boyfriend, a better person. Nevertheless as you might imagine when she comes over I am sure her bf would not be happy with how "comfortable" we are in-front of each other. Any way long story short, my question is about anal. She tried anal with this ex-buddy of mine and the previous bf before that and it was all bad experience, she was in a lot of pain etc. I remember she would blame hemorrhoid, so I checked her myself and found nothing wrong with her butt. She would also complain of constipation and blood when pooping. That was just her diet and everyone has blood in poop from time to time. She is short and curvy in all the right places.

Next time when we make love I want bring up anal with her. She is really against this since she thinks its going to be unpleasant. She has an adorable bubble butt and cute little asshole. Any tips you can give me to relax her and ease her in to the idea; any strategies or exercises she can do on her own? Are just some females too tight? I look at some women they seem to have little trouble with this, I wounder was this always like that for them? Your thoughts and input would be greatly appreciated, thanks in advance.

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Comments ( 5 ) Sort: best | oldest
  • Notsonormal83
    12 years ago | pl

    Use a lot of lube and slowly massage her hole to gently stretch it. Go slowly when you first go in. As as a woman, I know it can be painful at first, but that usually goes away after a few seconds once you're good and loosened. I don't think she's tighter than others. Everyone has a tight hole or we'd all be pooping our pants all day. You just have to use a lot of lube, tell her to take deep breaths while you're inserting, and start really slowly until it's loose.

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  • 100jimi
    6 years ago | pl

    My wife was on her v back for her first anal. I played alot with her pussy and put my dick near her asshole. I penetrated her during her orgasm and she praticly felt no pain. After that was only pleaser for her.

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  • reneerenee
    12 years ago | pl

    Enema and butt plugs

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  • [Old Memory]
    13 years ago | pl

    Hmm okay lemmie think.

    You could tell her to relax, get her a vibrator to use on her clit while you use lube and your fingers to loosen her up a little. One finger then two when she is comfortable with it. Then graduate to a dildo, not one huge but an alright sized one. Use it slowly on her, let her get used to it. Make sure to use lots of lube because the skin in there tugs easily. Keep her using the vibe. Then when she is ready, you can slide your cawk in there. Slowly. After the prep in her ass (and maybe some attention to her pussy from you) it should be fine from there. Also, keep her comfortably on her back for all if this so that she is relaxed the whole time. Do not start her out on all fours because it's impossible to relax in that position.

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