I want to learn how to make anal love to my girlfriend in such a way that she doesn’t describe it as hurting. Should we try a different position? I want it to feel so good. You are the woman who can help me.
–P.J., Reading, PA
I wish I could hop on a plane and give a personal tutorial to each couple who seeks my advice and guidance. I would arrive with a fully stocked briefcase of lube, latex gloves, condoms, vibrators, and butt plugs. I would let you two get revved up with lots of foreplay, and when you were both ready, I would lead you through anal penetration step by step. Go slow and be gentle. Use lots of lube. Work your way up, beginning with a finger or slim butt plug or dildo. Ask her if she wants clitoral stimulation; some women like to have their clits played with while getting fucked in the ass, others like their partners to concentrate solely on the butt. If she wants your hand or tongue or vibrator on her clit, give it to her. Talk to her the whole time, see what turns her on and what doesn’t work.
When you are ready to fuck her with your cock, find the best position. People always ask me: “What’s the best position for anal sex?” My answer: the one that works for both of you. Missionary position can be great, unless keeping her legs in the air or over your shoulders isn’t comfortable for her. Spooning works if your bodies line up naturally, and the man can get a good angle. If you choose doggie-style (my personal favorite), you can do traditional on-all-fours or do head-down-ass-in-the-air. With doggie-style, you can get a great angle to hit her G-spot, just remember not to go too deep at first. When you first enter her, just put your head inside, stop, and stay where you are. Let her sphincter muscles and anus get used to the feeling. Sometimes, she will actually suck you inside — when we are aroused, our anal canals and rectums start to contract and we can often pull a dick or a toy right in. If she doesn’t suck you in, slide into her very slowly. Many men make the mistake of trying to just shove it in there, and even with the most experienced woman, that just won’t work!
You sound like a very sensitive, caring, anal-sex-loving partner. Have you communicated your desires and concerns to your girlfriend? If she knows that you are caring and promise to be gentle, it will definitely set her mind (and her sphincter muscles!) at ease. You need to emphasize that, as the receptive partner, she’s the one in control of the action: it’s her call on how fast or slow, how deep or not-so-deep, and how much. That’s how I’d handle the situation in person. But, alas, my schedule just doesn’t permit it! Listen to her body and her verbal cues, go slow, and pretend I am there guiding you through it!