Huh. I’ve always worn underwear with my jammies. (Panties, not a bra, of course).
Pajamas have uncomfortable seams just like regular clothes. There’s nothing like going pantiless with a pair of pj pants on, and having that big nobby seam junction in the crotch of the pants, introduce itself to your delicate parts.
Night gowns. Much more comfortable.
Here’s something that nobody else has suggested, and I offer it only because it’s a possibility for some boys:
If the boy is intact (not circumcised) and (possibly) if he recently experienced the ability to retract his foreskin (which some boys cannot until puberty - a variation on normal) - or if his foreskin has grown to have an overhang - then it may be that some urine is pooling inside his ‘anteater’ after urination, and dribbles out after. In this case, an answer might be to have him skin his foreskin back to urinate/shake, and/or use a bit of tissue.
If he is cut, then it’s possible that now that he’s reached puberty, the chafing of his underwear is adding to his number of daily erections, with a small amount of pre-come being released.
Hmmm. I would aim for something subconscious here. No offense, but I whacked it like it was going out of style when I was that age, and never went through excess clothing. If I had, and mom noticed, I’d have figured something out pretty quickly. If he understands the concept of pointing it at the toilet, it’s not a great leap to avoid spewing on yourself.
If he’s peeing 4-7 times during the night, I’d say that’s an issue too. Maybe I’m weird, but I never peed 7 times a night for as far back as I can remember. Maybe once or twice, but I’d probably just wake up if I had to go really bad.
The kid doesn’t have an STD or a UTI either, unless someone’s experience extends a lot further than mine on the subject, that kid would be twitching if he had gonorhea for a year… and I’d bet he’d have said something.
I say set up a routine physical with the doctor, but tell the doc beforehand what’s up, explain it’s a secret, and tell your son it’s time for a checkup. Kids don’t know any better, and checkups are a pretty mundane thing at that age anyway.
I second the sex book, my folks did the same with me, with a copy of “The joy of sex”. It was weird, but I got over it pretty quickly due to the “never speak of it again” nature of the transaction.
Do not, under any circumstances, acknowledge masturbation in any way. There’s nothing nastier than hearing it from mom. My mother never said a word of it to me, and she caught me who knows how many times (We’re talking opened the bathroom door while my foot was on the sink and the other foot was on the wall caught me.) She acted as though she saw nothing, as should you.
A amle friend, whom your son has bonded with, is the best choice for this, be it Dad, brother, cousin, anybody both male and not mom…
(Sorry, it’s just icky talking about sex with mom, trust me…)
Sorry, one more detail that may be of help. My Dad was really good at this sort of thing, having had four boys before me, and he had honed it to a science.
He passed on a great deal of wisdom telling stories, which may or may not have been true, but which included details that were helpful. It took many years for me to realize how much information had handily passed between the two of us.
One such story included a boy he knew growing up, who was older than the boys he was friends with, who bragged about being able to masturbate, which none of them knew how to do. They told him he was full of it, so he showed them in his dad’s garage how he did it. This story was accompanied by appropriate gestures I’m sure you can imagine.
A similar story about your brother, or some other close male relative or friend may help, including a detail about them using a towel and later switching to toilet paper. It gives the kid some clues without broaching the subject directly.
Yeah, my Dad was a genius 
It is, however, easier for males to segue into the subject of masturbation. Don’t ask me how, it just is. With some creative storytelling though, I think you could manage it without it being obvious.
Speaking of crazy foreskin, is it normal to have a section of the foreskin still attached to the underside, right under the glans to where you can only retract it a little bit past the head? And oddly enough, it’s just connected there at a point, so I can pull it back farther on the top of my dick than the bottom. 
It may be normal for you. Your penile frenulum may simply be short. There are variations in frenulums all over the body. The frenulum under the tongue can be thick and fibrous, to the point of creating ‘tongue tie’, or it may be almost non-existent. There is a similar thing under the upper lip, at the center. I don’t remember what it’s called. Here is a photograph of the penile frenulum (not work-safe). One of its functions is to pull the foreskin forward to cover the glans when the penis is not in use. I would be surprised if the foreskin at the top of your glans acted exactly like the foreskin at your frenulum.
I imagine, as long as yours doesn’t hurt you when you retract, and doesn’t interfere with (or hurt during) masturbation or intercourse, it’s as normal as anybody else’s.
Yeah, that’s basically what mine looks like. (for all those people out there wondering what my penis looked like :p)
I’d also make sure your son does NOT find out about the Straight Dope. Having Mom know he’s wacking it is bad enough-imagine how he’d feel when he finds out she told a bunch of strangers online!
I dunno about the OP’s kid, but I hate doctors. If I had some horrible, painful condition, and my mum gave me a choice between “confessing” to masturbation vs going to see the doctor, I’d tell her I was wanking, even if I wasn’t. That’s definitely the lesser of the two evils!
Max.
I temporarily became incontinent during puberty. Erections were previously associated with a full bladder, but little came out - my bladder wasn’t full and I began to dribble. I couldn’t do a complete pee - more seemed to come out in spurts, if I kept up the pressure. Pee shyness ensued. I began holding it in by tightening my sphincter like one does when trying not to pee. This led to me not always making it to the bathroom on time. It stopped after I discovered masterbation.
So the solution might be…
[Robot Voice] DANGER, DANGER, Will Robinson! Apply lubricant immediately or your penis will burst into flames![/Robot Voice] 
Have you tried the hairy palms test? 
May I offer a bit more advice, vis Kleenex? The stuff just isn’t strong enough. Little bits of it tear off, and you wind up having to peel this high-protein paper mache off your knob if you’re not careful rub it off before drying. It can be an uncomfortable nuisance to say the least.
Something tough and absorbent, yet gentle on the skin would be great. Maybe a few rolls of a high-quality brand of paper towels, plus a nice tub of Handi Wipes for any tacky residue, placed discretely next to his nightstand, would be a boon for all involved.
[hijack] I’m SO glad I’m a girl and don’t have to deal with this. What a mess!
So much for penis envy, Dr. Freud. :rolleyes:
[/hijack]
So, dragongirl- what’s the verdict?
Isn’t that kinda… breezy?
It’s not breezy if you say it’s breezy.
[/obligatory Friends ref.]
Don’t you use sheets or blankets?*
*Also, if you’re involved with someone, it allows Easy Nighttime Access[sup]TM[/sup]
Well, yeah, but, but… I mean, don’t you walk around the house too?
Not to mention, one purpose of underwear is to have something you only wear one day so you can wear your jammies more than once, right? I mean… eww. Maybe I’m just damper than other females.