There's several things that can help make that one stroke count. Like others have said, putting a lotion or oil on can help. Also, rubbing ice and then pouring rubbing alcohol just prior can help. You can also use an irritant such as figging, icy hot, or for the truly brave you can try Finalgon. It's like icy hot x1000, but be very careful as the "sting" lasts 3-4 hours instead of the normal 20-30 minutes of other irritants. For more check out
This thread on fetlife.
As for the actual stroke, find out if the bottom prefers something more stingy or thuddy, and use the opposite. If marks are acceptable, I'd recommend
The Howler - from personal experience it is very intimidating.
The other option is to hit a very, shall we say, sensitive spot?
Get a
misery stick, and use it on the underside of the shaft, just beneath the head where the largest concentration of nerves are. Combined with icy hot (or for the truly sadistic the Finalgon) I guarantee you a truly memorable shot.
For even more intense fun, take a q-tip, put some of the irritant on it, and slide it just inside the tip of the urethra.
When using irritants, I'd recommend waiting 5-8 minutes between application and the stroke.
Good luck!