I happen to love role-playing in a spanking, although I know that many guys prefer just straight-up ass-whacking without "scenes" or inventive situations. Role-playing, to me, not only heightens the excitement of a spanking session, but is also an opportunity to "live out" various fantasies.
However I have to admit that my favorite role-play scenes are nearly all timeworn cliches -- "A Visit To The Principal's Office,"
"Son Brings Home Poor Report Card,"
"Angry Coach and Smart-mouthed Jock," and stuff like that. I have helped develop a few more exotic scenarios to cater to the particular tastes of some guys, though. One such was "A Visit to the Behavioral-Modification Psychologist," for a guy who was into tops wearing a business suit. Another was "Burglar Caught In The Act By Angry Homeowner" -- THAT one was a lot of fun! The "burglar" ended up getting a thorough paddling with a heavy silver cake-serving spatula which he'd put into his bag of "loot."
From talking to some guys, I have found that some men who like the idea of role-play feel intimidated about actually doing it -- like an insecure actor getting stage fright. They're afraid they won't be good at it and that as a result the scene will come off as silly instead of _s_e_x_y. I always do what I encourage others to do -- just go with the flow, and don't try to "act" too hard. Agree on a basic fantasy that turns you both (or all) on, and let things flow naturally from there.
At the other end of the scale is the occasional guy I meet who thinks he has to perform role-playing with all the histrionic excess of a community-theater Shakespeare production! That ruins a scene, for me, because the _s_e_x_y fun part of role-playing is that gentle pretense of reality. If you have to throw yourself into dramatic poses and shout out stilted dialogue, well, any semblance of reality is shot in my opinion.
The problem with elaborate fantasies is that they often require a lot of props, or things that are difficult or impossible to achieve for real. I suppose you could hire an eighteenth-century mansion for the evening and rent appropriate period clothing from a costume supplier for a "Caned At Eton" fantasy, but really -- who is going to go to all that trouble and expense?!?!
I did once know a guy whose ultimate fantasy was to be spanked and paddled on his briefs until the undershorts were literally "spanked off" of him -- the fabric of the seat destroyed by the paddling so that only threads and tatters remained on his bare ass. I thought it was a hot fantasy too, but obviously paddling anyone long and hard enough to destroy the seat of his jockey shorts would cause unacceptable damage to his ass! I tried several experiments, privately, before surprising my spank-buddy with his fantasy made real. From having ruined clothes accidentally with too much bleach in the wash, I knew that bleach weakens cotton fiber. So I saturated the seat of a new pair of jockeys with bleach, waited about ten minutes, then rinsed them out thoroughly. They still looked and felt like new, but when held up to the light it was clear that the seat was very weakened in the fabric. It worked perfectly -- he wore the briefs (which I hadn't told him about in advance) and as I paddled his bottom, the weak cotton began to slowly disintegrate under the force of the whacks. Before long, there was indeed nothing left but threads and tatters hanging over his red-hot asscheeks! He loved it, and shot a huge load into the front of the briefs over my lap. I enjoyed it a lot too, especially growling "I'm gonna beat those shorts right off your ass, boy!" and the like.
Role-play can be a lot of fun. It doesn't have to be tightly-scripted or elaborate. Just go with a fantasy you like and "live it" for a spanking session!