Hello!

In general, when you're starting to get into anal penetration, your best options are to start on your back or lay on your side, both with knees bent and up to your shoulders like a fetal position. It's the most relaxed way to be, similar to why it's good to use a squatty potty or any other kind of foot stool for toilets when going #2.

You'll also want to make sure you're not tense and nervous. Using fingers, small butt plugs to start for stretching, analinus (rimming) with the use of a "dental dam" for your partner's safety. I always recommend using an enema before starting. If you feel yourself unable to relax or you are tensing up, trying pushing just a little, just enough to relax you but not have an embarrassing moment (which will happen, so accept it now). And of course, safe, water based lubricants made for such an occasion.

Moving to other positions are better once you're properly stretched, have graduated to larger plugs, and you've become accustomed to anal penetration. Curvature doesn't play as large a role as you might think, but on your back facing your partner will more naturally fit the usual upward curve (some frown downard).

Hope this helps! less

Yeah, thanks. But you never know...
I can't imagine myself looking eyes-to-eyes with my gf, i she ever agrees

If I may ask, how old were you and your wife when you got into pegging, if she was the one you started with? how much time have you lived together before that? less

My wife and I don't engage that way, nor am I into pegging. I have been around long while and learned a lot about how best to approach anal with my previous partners (my first time was done all wrong). I also started using anal toys on myself for P-spot stimulation. So, my advice comes from my experience with other women and my personal experience with toys.

Why are you concerned about making eye contact with your female partner? less

well, it doesn't matter if with wife or someone else, I'm just interested in the age when men get into anal and do it regularly or not too reguarly. Not the ones who previously were gay or bisexual, but people like me.

eye contact? I don't know, it feels embarrassing. Yes, I know it's not gay, yes, it's your girlfriend/wife/SO, etc. But still, when I picture it, I can't help feeling shame less

Age might play a factor, but perhaps not as large a factor as the age we live in. As I get older, I notice I don't care about the smaller things as much, especially what other people think of me. That combined with sexuality becoming less demonized in the United States, I became more open to the idea of trying different things that I may previously thought were strange or worried others might think so. I think I was about 30 when I started to experiment anally on myself and not just on others.

Sex feels more amazing than probably anything else available to biological creatures such as ourselves. As good as 10 feels, we're still trying to find ways to make it go up to 11. Human nature. What goes against our nature is the introduction of shame. Shame is one of the worst things humans have visited upon each other. We are naturally naked and naturally feel sexual attraction to the opposite sex, same sex, both sexes, or neither (I may have left out larger parts of the spectrum, but not purposely). Yet, we've been conditioned to remain clothed and to feel that sex is bad, especially if it's homosexual sex. These attitudes we are taught prohibit us from exploring or just even relaxing enough to enjoy sex and get good at it. I have a theory as to why, but it's much larger and I don't want to distract from my point.

It's evident in your replies that these attitudes still have an adverse effect on you. The only advice I have would be to get passed it in any way you can. Be honest with your partner, let him/her/they know what you want and what is keeping you from getting there. Let them help by suggesting or trying other things, like maybe maintaining eye contact no matter what you're doing with each other is the challenge see if it helps. More often than not, practicing things how you want them will get easier the more you do them. The most important thing to keep in mind throughout is that it's not weird, it's not "gay" (and if it were, who gives a flying fuck at a rolling donut?), it's nothing to feel shame about. It's your body, your pleasure, your life and you only get this one trip around. Why spoil it by accepting other people's insecurities (i.e., gay bashing, sexual taboos)? Go for it and keep going for it until you've finally comfortable. less