Hump my leg. (I like submissive boys)

some guys like to be stepped on with stilettos, although you've probably done that. step on his balls with them?

make him jerkoff using icyhot or bengay as lube

i'm guessing you've already tried human furniture?

Use dental equipment as local pressure tools of torture.

ooo invite several girlfriends over and make him be your nude waiter/butler for the evening

I like the way you think

I realize that living in the 18th century has its advantages. No Rand Herp! Har har har.

As for Lucy's initial question, I had a short discussion with the Bastille's torture master. He suggested flaying, as the human skin is the last barrier of intimacy, removing it is quite humiliating.

Then again, I'm not sure if flaying is allowed in 21th century's New France...

My torture master also suggested using the patient's personal phobiae. If he suffers, for example, from aibohphobia, you may force him to recite palindroms in public.

Besides this, I don't have much to suggest you couldn't figure out for yourself. Forcing him to urinate into his pants on a ball; covering him with honey and burying him next to an anthill; putting maggots into his pants before going to the opera; forcing him to disturb a fox hunt disguised as bunny - all these ideas are not new and I am sure you already had them.

Did you already try the old trick with the goat and the salt on the feet?

Your Majesty;
Would it not be more entertaining to have him disguised as a fox?

There's nothing worse than the pustules of idiocy sprouting on one's "fountainhead."

Indeed, that would be much more entertaining. Especially if he wears a fresh fox hide, as the foxhounds are dressed to follow the fox smell.

I don't know where you came from, but you're my favorite new member since I don't remember when.

No. Furries are bad.

Fixed!

i don't know anyone, outside of a hilarious episode of Entourage, who can stay hard in a fur suit.

I've got one (by the way, the riding the leg thing was pretty hot, I never thought of that, maybe make him do it while watching in a mirror to see how he looks)

I remember seeing a cartoon many years ago that talked about how a man is comfortable naked in front of his doctor, and naked in front of his wife, but not naked in front of both of them. It showed a cartoon with a guy squirming in discomfort naked on an examination table, while his wife and doctor talked in front of him.

Think about making (forcing) him to take off his clothes in an uncomfortable situation. In front of you, and somebody else. He's used to it with you, but what if someone else was present?

Think about, you're and artist, and he's your model, he's posing for you, nude, and then the UPS, or FEDEX, or whatever, even pizza delivery comes by, and you answer the door to pay for the stuff and he's sitting there, not knowing what to do with himself.

I've never used this fabulous invention you call "telephone", but I imagine when you make him telephone with his mother while you do things to him his mother certainly would not approve, this could be quite embarassing for him.