You know, ladies, you can buy your man a lot of different holiday gifts, but most of them are things he could just as well purchase himself. But there's one thing only you can give him. Yeah, I'm talking about giving your boyfriend the prostate massage he told you he's been fantasizing about. If you've never done it before, you might be a little nervous, but I'm going to give you the 101 on fucking your guy in the ass.

First, tools: Get some latex gloves—any drugstore has them—to keep your hands clean and to keep your fingernails from scratching your partner's insides. And some good thick lube, because spit will not do for this. I like the "Sex Grease" brand.

Those are the two most basic requirements. You can get a big response fucking your boy with just fingers, especially if he's an ass-virgin. But let's talk about dildo selection.

Definitely get something that cannot accidentally go all the way up someone's ass. I have dealt with exactly one episode of a toy getting away during anal sex, and while everything—ahem—came out okay, it really wasn't a good experience. Everything's going to be slippery, and there may be a lot of wiggling around, so get a toy with a big flat base, or a scrotum, that cannot possibly escape your fingers.

Something roughly the circumference of two or three female fingers is a reasonable size for beginner butts. I suggest a toy that vibrates, as vibration relaxes that tight little ring of muscle, and prostate glands like the buzzing sensation too.

You don't absolutely have to have a strap-on harness, although they are fun to wear and I love mine. But I've also had a great time fucking boys with a dildo that I was holding in my hand. There are different styles of harnesses, so if you want one, go down to Babeland and let them help you pick one out.

Now, let's talk positions. The classic all-fours pose is my favorite. Once you're both more experienced, you can try putting him on his back, but he'll have to pull his legs pretty far up, and it's a more strenuous position for a newbie.

Glove up and get a good-sized dollop of lube on your fingers. Then start by just massaging his rosebud for a few minutes. Don't push inside, just rub gently and slowly. If he's nervous, kiss his neck and remind him, "I'm not going to suddenly ram my fingers into you. We're going slowly." Give him a little reach-around fondling if you can get to his cock easily—or let him play with it himself. Keep massaging until you feel the ring of muscle relax and soften up a little under your fingers.

Then add some more lube and slide a finger in. With ass-virgins, even one finger often gets a big reaction. Just hold still for a minute or two and let him get used to the sensation. Then start moving your finger slowly. If you press down gently, you should be able to feel his prostate gland—a small rounded bump under your fingertip.

Finger-play may be all your boy is ready for on his first time out. That's common. But when he's ready to try something bigger, put a condom on your toy for easy cleaning, and get it all lubed up—there is no such thing as too much lubricant when it comes to butt-sex. Warm up his ass with finger play, then slowly work the dildo into his ass one slippery inch at a time. Don't rush, keep checking in verbally, and back off immediately if it gets too intense. With deeper penetration, it's possible to get some santorum, so keep some paper towels handy.

Taking even a slim dildo all the way to the hilt takes practice—you're unlikely to be really pounding your boy's butt right away. But once he's ready for more energetic fucking, then you can get out the strap-on harness. Now's when that vibrating dildo really pays off for you—it'll feel good buzzing against your pussy as you slide it in and out of your boyfriend. After all, the best gifts are the ones that bring pleasure to both the giver and the recipient. n

Kink Calendar

FRIDAY 12/16


Socializing and BDSM play at a private location. Women only, 8:30 pm–2 am, $10/$15, RSVP to Evee at


BDSM play party for the boys. Wet Spot, membership required, or 270-9746, 10 pm–3 am, $15, male ID required.


Swing club Redmond Ranch throws a holiday party with a strip show. Single men must RSVP for waiting list, couples/single women can just show up, 425-868-8169. Doors at 7 pm, new people must arrive by 8 pm, $45 for couples/$25 for single women.



Got basic flogging skills but want to improve? Noted percussionists Russell H. and Erika G. will teach you the fine points. Everyone pairs off and takes turns being the practice dummy, so bring a heavy jacket and a flogger if you have one, although some loaners are available. Wet Spot, info at 650-5234, 2 pm–6 pm, $35, membership not required.

SUNDAY 12/18


A clothing-optional "swim and be social" event at an indoor pool. The Longhouse in Redmond, or 270-9746, noon–4 pm, $10, RSVP required.



Teach your ankles a BDSM lesson at Seattle Center's Winterfest Ice Rink, situated in the kinky Fisher Pavilion. Fisher Pavilion, Seattle Center, $5 to skate/$2 skate rental. 11 am–5:30 pm.