Dear Richard: Dil-dos and Dil-Don'ts

By: Dear Dick

Dear Dick,
I'm a young 19 year old gay guy and I have a few dildos that I like to use. I love the pleasure I get from them but right after the grand finale happens all that pleasure turns in to pain. I was wondering if this is normal, or what?


Dear Normal,
If we could only tell you the untold hours we spend here in the labs testing the pliability and depth of of 19-year-old mens' anuses.

Hundreds of volunteers have to be herded in to help test various lubrications, dildos, and anal stretching devices. You'd think we'd all be exhausted from that, but no. We then need to test these same orifices with the very real penises of our staff.

Yes, it's arduous work, but scientists — and even a few former prison guards with a bent for research — stay dedicated to the final results: Data that can improve your butt pleasure.

All of our testing facilities are monitored by seasoned experts, closed circuit video cameras, and in some cases personal iPhone cameras, to catch every expression and declaration of pain and pleasure as our young volunteers go through a battery of examinations and tests. These tests often for last hours, or even days at a time.

OK. All of the above was a fantasy. But it was a nice one, right?

We did poll the guys in the office, a few of our more experienced friends, and that cute guy that works in the coffee shop downstairs, and here is the consensus of both opinion and experiences:

Your experience seems to be pretty consistent with the other guys we know who like to put stuff up there. One of the differences between a dildo and the real deal is that a dildo stays a consistent girth and rigidity no matter what. Once a real penis unloads (in a condom, please) in your butt it begins to lose some of it's hardness and thickness. Sometimes it just pops right out.

Also, if you are riding the rubber stallion to your own orgasm, your anus and rectum can contract right at orgasm and stay clenched for a bit. That's great news for your partner, but the rubber stallion could care less. So there will be no loss of size or rigidity when you are removing it. It might help if you wait for a while and really concentrate on relaxing before you plan your exit strategy.

This too: Just as you have to concentrate and bear down enough so that the actual aperture of your anus relaxes enough to admit Mr. Big, you might also try experimenting with the same technique for the big goodbye.

Some other things to consider: Many randy young men like you have eyes bigger than their openings. Because you can take your time and squirm about for hours on that thick column of silicone to eventually get the WHOLE THING up there, you are probably taking in something much larger than the average guy. It only makes sense that you might have to go through some discomfort in the afterglow.

And if you are using any drugs, even stuff as benign as poppers, it's going to make dido removal more challenging. We don't recommend that.

So, as long as we are here, talking about you sticking stuff up your butt, let's review a few of the basics of dildo play:

• Go slow and relax.
• Plenty of lube
• If you share toys at all with your lover, fraternity brothers, or mailman, always put a condom on the dildo before you put that dildo in you.
• As much fun as it is to stick amusing things in your slot, stay with approved sex toys. You don't want to be some emergency room technician's favorite story of the night.

So good luck and happy stuffing, young man. Be sure to get back to us and let us know how "it all comes out." Hey! Send pictures, huh?


Dear Richard is not a medical doctor, a licensed psychiatrist, a counselor, a reverend, or a rabbi. He has not been evaluated by the FDA, the CDC, or the BBC, and his words are not intended to diagnose or treat any condition. The information is for educational purposes only and it not intended to serve as medical advice. Dear Richard does, however, love hearing from you and answering your questions. Leave a comment or send him an e-mail.