As you can tell by the title I am here about anal sex. I have a sincere enjoyment of anal sex both receiving and preforming it. My girlfriend, goddess bless her, wants to give it to me and has tried multiple times.
It's a complicated issue, something we've been working on for years. One time, ONE TIME, I managed to actually give her an anal orgasm. But the same method didn't work twice (damn our female bodies and their constantly rearranging pleasure zones). I've done everything I can think of from ensuring cleanliness to slowly working up from small toys (about this size of a thumb) to the size of an average phallus (5x1). It feels okay, at least she can take it with only a minor amount of discomfort, till about this http://www.edenfantasys.com/anal-toys/anal-probes/key-to-your-butt however after that it just hurts too much.
I was willing to drop it and let it go. I figured you know it's not that big a deal, and if the smaller ones work for her then okay we can still have plenty of fun with just that. But she feels really guilty about not being able to give me one of my fetishes. She actually cried the last time because she felt she had failed! FAILED! I was thrilled that she had tried so hard for me! It made me want to fuck her even harder!
She says it's because I give her all her fantasies and work so hard to do what she likes. She wants to make sure she can make mine come true. I reminded her that I am good at her fantasies because I enjoy giving them to her and I get pleasure from them too. So I don't want her to do this if she just can't get pleasure from it to. But she wants to, and I want to. But I don't want to hurt her. But she feels OBLIGATED to take it!
I'm at my wits end! I want to make this good for her. She really enjoyed it when we made it happen that one time and I think we both want to take it to that level again. This isn't something that we do every day. It's maybe once a month or so when we're feeling ready for that level of (frankly) effort.
I want to just make it pleasurable. I want to help her enjoy it. It's not impossible and I've done my best to read up on it. Well now I'm after more practical advise.