My suggestions:
1) tie him spread-eagled on his back for maximum helplessness; you want him to feel *vulnerable*, so strip him down as much as he'll let you (and that you feel comfortable with). Once he's tied naked, get naked yourself (or as undressed as you feel comfortable getting). The fact that he can see but can't touch should drive him crazy.
2) do a quick 'spider-walk' tickle all over his body to see where he's most ticklish; get every area at least a little, to reinforce the idea that you *can* get him anywhere you want to. Remember, much of this is a psychological game! This will also ensure that he's tightly tied. Tell him you have to "test him, to make sure he's adequately tied up" You don't want him to get away!
3) use a blindfold at times, but not all the time. when he's blindfolded, walk around the bed and zoom in for quick tickle attacks; pause between attacks and remind him that he doesn't know when it's coming; in other words, mess with his head! keep him off balance by getting one side of his body, and then -- when he least expects it -- the other. don't linger in one place too long!
4) when he's not blindfolded, straddle him and wave your fingers in front of his face, taunting him. zoom in and stop before you actually touch him. You might be able to get him to laugh at 'phantom tickles'. This can be a great psychological game. Also, try starting at his wrists, stroking them very softly with your nails; then move down -- slowly -- toward the insides of his elbows and toward his armpits. If his armpits are ultra-ticklish, you may be able to get him begging for you to stop before you even reach them. If he does, ask innocently, "what's the matter, is that area off-limits? I don't think you're in *any* position to declare *any* areas OFF LIMITS!" On the words "off limits" get him really good -- right in his armpits! Also, try a variety of tickles over and around his armpit area (and any other ultra-ticklish spot). try strokes, pokes and even massage/kneading.
5) once you've found his *worst* spots, play games with him like, "if you can hold out for 30 seconds, I'll stop." of course, you can do the counting (and make it slow!), and -- when you get close to 30 seconds -- zero in on his WORST spot, making *sure* he doesn't make it. Then you can "punish" him for failing the test.
6) use your fingernails and fingers -- forget the other implements.
7) if he begs too much, threaten to gag him; then gag him anyway and tease him when he tries to speak through the gag.
8) be thorough! don't forget often neglected areas, such as the knees (tops and bottoms), the pelvis, his balls, the insides of his thighs, his back (behind his ribs) and his neck.
9) don't forget to taunt him while you tickle him! consider this play-acting -- and play it to the hilt. Suggestions:
-"awww, poor baby, what's the matter -- are you too ticklish to take it?"
-"come on -- it doesn't tickle *that* much, does it? you must be FAKING it"
-"tell me your most ticklish spot -- or I'm going to tickle every inch of you until I find it, and then you'll really be sorry!"
- "look me in the eyes while I tickle you, and don't look away, or you're really going to get it!" [works best when you're straddling him]
-"if you say stop, I'm only going to tickle you more"
-"if you want me stop, say 'please tickle me'" [when he says it, act as if you've forgotten your earlier instruction, and say, "you want me to tickle you, ok!"]
10) if you want to get creative, tie him to a high backed chair, ankles to the back legs (forcing his soles upwards, and easily accessible), and his arms high over his head and back over the top of the chair. Again, strip him down as much as he'll let you. Then put him in front of a mirror, so he can see how helpless he is. Stand behind him and tell him to look in the mirror as you run your nails all over his body!
11) be very careful about retaliation! In other words, don't dish it out, if you're not able to take it!!
Those are my suggestions. Happy tickling!
Oh and this is assuming it goes that far.
