And clear out those follicles and acne too, right? We are on a tight budget.
Have him soak a towel in as hot water as you can get, then wipe his face thoroughly with it before and after. That’ll make the shave less irritating and the skin feel less taut accross his jaw. It’s one of the most irritating things about starting to shave. I currently wear a respectable facebear, but usually shave when I’m doing job interviews and the like and the sensation that the skin on my jaw is actually bursting with stubble is one of the reasons I wear a beard.
If he’s using a bladed razor, tell him to try shaving in different direction and figure out which he prefers. For me, it’s always in towards the mouth, except under the chin where it needs to go straight down. But this varies greatly from person to person.
Also tell him that he is under no circumstances allowed to grow neither moustache nor beard before he turns 20. (And then the moustache only if he changes his last name to Selleck.) If he allows any stray hairs to grow longer than a quarter inch, it is in fact entirely permissible to tackle him and forcibly shave them off.
You kiddin’ me? She’s a single mom. I’m sure she has waxing strips somewhere. 
As a girly girl who ALWAYS had problems with shaving rash, I totally recommend aloe gel as a shaving implement . We found this as a shaving gel for swimmers in the 90’s. It’s amazing. No rash at all, use it still.
If he’s interested in trying an electric, I highly recommend a Braun Mobile Shave. It’s a pocket-sized electric with a rotating blade cover. Only around $20.
Obviously it’s not as good as a $200 Braun, but it’s much better than anything else even CLOSE to that cheap, and it’s a really useful shaver to have as a backup if he upgrades later on. I always have one in my glove compartment for “emergencies,” and it’s great for taking on trips.
It’s also a really, really great bit of industrial design.
It’s all in the technique. If you shave correctly, you can use an off-brand multi blade razor with something like Barbasol ($1.20 per can) and have a close, irritation free shave.
If you don’t shave correctly, it really doesn’t matter; you could use really expensive stuff and still have a hard time with it.
The 2 real keys are to shave WITH the hair, and to just glide the razor over your skin. The point isn’t to dig in with the blades, but just let them cut, which requires no real pressure.
Shaving with the hair means that you’re not pulling partially out in the opposite direction from the angle that they naturally grow at, which helps with not tearing up your face and giving yourself too much irritation.
An electric is probably a worthwhile investment for the time being. I’m sure it varies based on genetics, but IME, electric razors are for kids. But that’s OK, he is a kid. In a few years he’ll want a closer shave, and that’ll require a razor. The goofy multi-blade technology really does work better than the disposables. I have no idea how much these things would cost for a regular user, though – I’ve been bewhiskered for over a decade, and with shaving my neck clean once every week or so, I can get by on one or two refill packs a year.
–Cliffy
If you use a blade, the most important thing is to dry it afterwards. Not doing so means that the blade or blades rusts at a microscopic level. Drying the blade rather dramatically increases the life of the blade.
Do they make special little towels for drying razor blades?
Or should it be dried with, say, a blow dryer?
Depending on how hairy he is right now, maybe just plucking the more noticeable whiskers would work.
I dip them in alcohol. The higher the percentage the better.
You could use a shot glass, then drink what remains, toasting your close shave.
I’m obviously doing it wrong: to get a smooth shave, while the first stroke may be with the grain, I have to shave against the grain for the final stroke.
I’ve tried shaving in the shower, and find that most of the benefit is from the soaking in hot water. Which I can just as well do by taking a shower, then shaving at the sink afterwards.
To summarize: take a shower before shaving; it will make things go smoother.
And, FTR, I need to shave against the grain to get a close shave. If there’s more than a day or two of growth, I might need to make a first pass with the grain.
Every beard is different. I have no regular grain. A clean shave requires several different directions to get everything.
This is a disgusting suggestion to make in this thread. Obviously the OP’s son is already missing a father figure in his life. He’ll never learn any responsibility if his mother is paying for his hookers. He needs to grow up, get a job, and pay for sex himself like the rest of us.
I find that the aloe varieties of Barbasol or Noxzema (the green can, in either brand) reduce irritation from shaving for me. I also shave in the shower, for that reason as well.
The can with the grey cap is the one for sensitive skin. Highly recommended.
Shower before and after shaving.
And if thou do not shave every day, shower on those days as well, else you be seen as unclean, sayeth the lord.
For this and a dozen plus other little things a guy will need to know:
A Boy Should Know How to Tie a Tie: And Other Lessons for Succeeding in Life
OP, get this book for your son. Trust me.