My boyfriend and I think anal sex is super hot and are determined to be pros at it! We’ve played with fingers and anal toys and managed to have a pretty successful penile-anal penetration experience once, but it hurt so much that now I’m afraid to do it again.

I’m not against anal sex or anything mentally, but I think my body might be against it physically? Where do we go from here? Is there a way to make this work or are we doomed to a life of plain ol’ vaginal sex?

Anal sex with your boyfriend’s penis, like Rome, wasn’t built in a day, but was rather built stone-by-lube-slathered-stone and with a lot of patience. You won’t be building an entire, tourist-packed city of pleasurable anal sex in one night.

It sounds like you’ve done some good — ahem — “leg” work here what with feeling mentally engaged and turned on by anal sex, which is an often-overlooked but super-important initial step. That giant sex organ called the brain is too-often neglected, especially with anal sex. When we feel afraid what does our butthole do? It tightens right up, making penetration difficult and painful. Being genuinely mentally into the sex you’re having is very important.

However, as you’ve learned, your body can’t always work as fast as your brain. Fantasizing about letting your boyfriend’s number one celebrity kick through your VIP backdoor entrance like some kind of anal sex rockstar doesn’t make it so. You say you’ve worked up to this shining, lubey moment by playing with fingers and toys (small buttplugs, I’m assuming) which is great.

But are you taking the time to warm up with these familiar friends-of-your-fanny directly before penile penetration? Or are you banking on that one time you used a buttplug last week to tide your tushy over? Just because you managed your biggest booty plug that one time doesn’t mean your butt is now open and available to you throwing whatever you please in there…continue reading…