The V-Spot: Hell-Bent on the Back Door


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.

Before your boyfriend’s penis goes anywhere near your anus, you want to be mentally and physically turned on. Start with ol’ faithful sex acts that get your juices flowing. Don’t hesitate to have P-in-V sex for a little while first, either. Just because you want to have The Anal Sex tonight, doesn’t mean you have to skip straight to it without passing Go (… down on me). Just because you start with your favorite butt toy or fingers doesn’t mean your boyfriend’s penis will be barred from the patootie party. Take your time. Your butthole and his penis aren’t going anywhere. Warm up with smaller object penetration. Slather on thick, anal-friendly lube like my favorite Sliquid Sassy Booty formula.

Then, THEN when you are finally on the slow, pleasurable train to P-in-A town, don’t forget to enjoy the scenery. I’m talking simultaneous stimulation: put a vibrator on that clitoris, your favorite companion dildo in that vagina, his mouth on your mouth, whatever lights your firecrackers. Simultaneous stimulation not only feels delightful, but the familiar pleasure tends to put the mind and body (especially that booty) at ease, making penile penetration easier.

Your recent painful experience puts you at a slight disadvantage because you need to work on letting go of that butthole-clenching feeling called fear based on the memory that this hurt last time. If you move slowly, paying sexual and sensual attention to your other favorite bodyparts, warm up your booty, and use a lot of lube, anal sex doesn’t need to hurt (contrary to popular myth). But if it does, stop what you’re doing and either go back to the last pleasurable thing you were doing, take a break, or stop for a minute, a day, or a week. Pain is an indicator that something is wrong. Don’t ignore it or push through it, buying the idea that “this is how anal sex goes.” Because it doesn’t.

Finally, HBBO, remember the saying, “When in Rome, do as the Romans do?” Take your time, communicate emphatically, and use your hands a lot. You’ll be a pro in no time.•

Yana Tallon-Hicks

Author: Yana Tallon-Hicks

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