Start with a finger and go slow
When massaging the prostate, don’t just jam things in there
Lynn Don
Sex Columnist
Some of you may have read the hilarious story of the man who got a vibrating dildo stuck up in his rectum and live-tweeted the subsequent trip to the hospital — going as far as to post an x-ray — dildo and all.
When one of his followers asked him why he had stuck a vibrating dildo up his butt he replied unapologetically, “Have you ever stuck anything up your butt? If you hit the right spot, it’s fantastic.”

Yes, boys and girls, this is the x-ray photo that twitter user Grawly posted of a vibrator stuck up his butthole. Photo courtesy: Twitter.com/@Grawly
He’s referring to hitting the prostate, sometimes known as the male G-spot. When pleasured just right, it leads to a mind-blowing orgasm.
I’ll unfortunately never be able to experience this orgasm, due to lack of prostate. But perhaps I can help some of our prostate- having readers get acquainted with their dirt star and their male G-spot.
I recommend trying out some solo techniques first before you bring another person to the prostate party. The chocolate starfish area is still often seen as a taboo area sex-wise, understandably.
The main purpose of your rectal area isn’t exactly sexually appealing (unless you’re one kinky motherfucker), but let’s keep an open mind here. Plenty of people love butt play and one of those people could be you.
If you’re super uncomfortable with the idea of sticking anything (including your own fingers) in your ass, try this instead: when masturbating — once you feel like you’re right about to cum — rhythmically press on your taint (the area between your balls and your asshole).
If you hit the right place/rub it the right way you can stimulate the prostate and it can kick your orgasm up a notch. This is a matter of luck though, because it won’t always work. If you succeed, you’ll get an idea of what a prostate orgasm is all about and maybe be more willing to do some ass exploring.
A big part of this is being relaxed. Have a nice hot shower or bath beforehand. Maybe wait ‘til you’re alone in the house so you aren’t interrupted.
Now get on your back and kick your legs up against a wall. It’s time for some self-love. Try and get in a position where you have easy ass access and you’re comfortable. A bed would make sense. Putting a pillow under your bum might help you get comfier and give you better reach as well.
Massage the area around your anus with your index finger, moving closer towards it as you get more comfortable. Apply more pressure as you go. When you’re ready, apply some lube to your index finger and slowly enter.
The prostate is a small chestnut-sized bump located roughly two inches inward. Every guy is different in terms of what will get him off, so do what feels best for you. It might be gentle thrusting; it might be a constant pres- sure against the prostate.
Give it some time to figure out what feels best. Don’t get frustrated if it doesn’t feel amazing right away, but if you just aren’t enjoying it no matter what, that’s okay, this isn’t for everyone.
It’s good to start off with just a finger (or two), but a toy might be more your style. Be careful not to get anything stuck up there.
There are many sex toys made purely for stimulating the prostate, so give it a Google or visit your local sex shop. Remember, silicone is the way to go. Many are hands-free so you can service your penis while getting prostate pleasure.
Or, if your partner is up for it, they could give you oral while simultaneously stimulating your prostate. A butt plug could also be used during other sexual activity. If you’re into dudes, getting fucked in the ass will almost certainly hit that G-spot.
And let’s not forget the still- taboo act of pegging, which is when a woman penetrates a man with a strap-on.
This isn’t something everyone is going to be down for, but if you’re into it, talk to your partner. If you’re an amateur to anal play you might want to build up to it through other anal stimulation before you jump right into getting pegged.
If your partner is uncomfortable with pegging, starting with a finger might make them more at ease than just handing them a strap-on and saying, “How about it?”
There are many possibilities for experiencing the prostrate orgasm. I know butthole stuff makes a lot of guys feel uncomfortable (particularly straight guys).
But if you can get past the awkward stage you have a lifetime of intense orgasms to look forward to. Have fun with your ass!