How To Anally Stimulate Your Boyfriend Like A Champion

By Gigi Engle

I'm sure this will come as a surprise to approximately no one, but I'll say it anyway so that we can begin this article coming from a place of truth and understanding -- I'm very into butt stuff.

All things revolving around the derriere I find utterly fascinating. Just yesterday, while standing behind bae in the shower, I found it literally impossible not to repeatedly smack his butt while he washed the shampoo from his hair.

I'm just into the butt. I was doing some light reading about the prostate the other night as I often do and it occurred to me that all of my personal anus exploration has been almost exclusively trial and error.

Sure, there are plenty of “how to have anal sex” guides to assist us through the conquering of our own lady-butts, but there is no manual to guide us ladies through the passageways of prostate stimulation.

Being no stranger to all things anal on my backend, I wanted to know more about getting up in a guy's a-hole. I wanted to make a little “how to” for all you wayward butthole adventurers to have at the ready for the next time you want to go to town on your man's butt cherry.

To help in this endeavor, one that I have no doubt will earn me a Pulitzer and possibly the Nobel Peace Prize, I asked Amy Levine, sex coach and founder of "Ignite Your Pleasure," to help me help you.

WTF is a prostate?

You might be asking yourself, “Um. I'm sorry, WHAT is a prostate? Because it's freaking me out.”

Let me put your worries to rest, little ones. The dictionary definition of a prostate is, “a gland surrounding the neck of the bladder in male mammals and releasing prostatic fluid.” Its main function is to release prostate fluid, which is one of the elements of semen. This small, walnut-shaped gland is essential to the reproductive process.

It's located just inside the rectum and can be reached through the butthole.

Here's a diagram so you can see where it's located:

Web MD

Many men enjoy having their prostate stimulated. I asked Levine why this is and she simply said, “It feels good.” Sometimes these things don't have a real explanation, they just are the way they are.

Why do men get weird about it?

Some men are weird about letting their girlfriends do stuff to their butt. The reason for this is rather simple: many guys are insecure about their masculinity and status as “alpha male.” They think if they let their girlfriend into their a-holes, it takes away their status as a male.

Of course, this is ridiculous.

As Levine puts it,

It stems from homophobia and what it may mean if they enjoy it. All it means is that they like their prostate touched -- it's not an indication of their sexual orientation.

Enjoying prostate stimulation does not make you gay. Every man has a prostate gland and it feels good to have it stimulated, no matter which gender you prefer.

What do I say to gain access to the anus?

Levine says that a conversation about experimenting with prostate stimulation is a must. You shouldn't just go sticking your finger in your boyfriend's ass without his consent.

I know, I know. Most of us ladies have had a rogue finger up our butts before, sans convo, but that doesn't make it right. If you want your boyfriend to feel comfortable with it, you have to talk about it.

Levine suggests making it about a larger discussion about anal sex, “It's a conversation starter about if he wants to try anal sex on you. And you can say, 'I'm open if you're open to anal exploration too.'"

You have to give a little to get a little. Mostly, it's about being honest and open. Sex should be fun and explorative, not this high-pressure thing.

How do I penetrate the man cherry?

Even before you have the conversation about anal play, you can gauge your boyfriend's interest in butt stuff by engaging his perineum. Also known as the taint, the perineum is the space of skin between a guy's ball sack and his butthole. It can feel really awesome to have it stimulated.

The next time you're giving him a BJ, reach up and press two knuckles against his taint and knead gently. He may not even know this was exactly what he wanted.

I suggest trying prostate stimulation either during a blowjob or while you're in the reverse cowgirl position. You want to be able to easily reach the area without too much strain on your body. It's not the easiest gland to reach during sex.

Levine gave us a solid breakdown on how to reach the prostate,

When he's lying on his back. Either of you can slide a well-lubed finger or toy slowly into his rectum along the belly button side of his body. The gland can be felt about three to four inches deep. [While] the prostate is actually on the other side of the tissue, this is how it gets stimulated.

Once you get to the prostate, you can gently touch it or hold a toy against it to increase stimulation.

I usually put a condom over my finger before going up the dirt road because I have long fingernails. Just a suggestion, ladies.

If you're looking to use butt toys, Levine suggests The Hugo. I'm a big fan of Doc Johnson's butt toys. Just remember that butt toys need to have a flared bottom. Otherwise, you risk losing them in the anus and that could mean a delightful trip to the ER.

Do not put a regular vibrator or dildo up a butt. It is both gross and you run the risk of permanently tainting your toys with an unpleasant odor.

Be sure to sign up for Gigi's newsletter for the latest in love and sex.