I am very keen to experience anal pleasure but am worried about it hurting. I'm also not sure how to approach it with my partner, in case she is put off by thinking it is homosexual. I have had anal sex with her and feel that it would be a nice sensation for me as well. Can you help? Your advice would be much appreciated.
This is a great question that I get frequently from men who want to enjoy anal but are afraid of two things: 1) it will hurt and 2) it's connected to being homosexual.
I want to address #2 first. Just be honest with your girlfriend. Let her know that you are afraid that if you receive anal pleasure that she might question your sexual identity. Most likely she will appreciate your vulnerability and honesty. If she does think that pleasuring you anally has something to do with your sexual identity or preference, you can reassure her of your sexual preference. This also gives you the opportunity to educate her about anal pleasure. It makes sense to most women that they like anal pleasure, and that doesn't mean that they are homosexual. We all have anuses and they all have pleasurable nerve endings regardless of our sexual orientation. Most straight men that I know enjoy anal pleasure when it is done right.
That leads me to address your question about it hurting. If anal touch is done right it shouldn't hurt. I think of the tissue of the anus like a balloon. If you poke the balloon too hard it will pop, but if you ease into it slowly with your finger you can touch the other side of the balloon. It's the same with anal tissue. Tell your girlfriend to go slowly and deliberately with her touch and to spend plenty of time massaging your anus externally before penetrating. And use lube ! I recommend Aloe Cadabra or another natural lubricant. Have your girlfriend massage your anus and when you feel ready for penetration, she can work your first anal sphincter and eventually move to your second anal sphincter. As your tissue relaxes you can receive more and more stimulation. For you it is important to breathe deeply and relax as much as possible. It's about surrendering to her touch and the pleasure of the experience.
If you need to learn techniques for anal massage it might be nice for you and your partner to watch some instructional videos together (my Red Hot Touch: Exquisite Anal Massage DVD has received rave reviews) or take a workshop on erotic massage. There are also a number of books on anal play and pleasure if that feels more comfortable for the two of you to explore.