I was wondering if others have any aspects of BDSM play or certain specific activities that they love but hate at the same time. Something that you are powerfully drawn to but find very challenging or even unpleasant while they are happening?

For me it's having a session continue after I am brought to climax and being forced to endure until I am able to be aroused again. I'm one of those people for whom enjoyment of BDSM play is directly connected to sexual arousal and for whom that enjoyment evaporates instantly with orgasm. The times I have negotiated a CNC component to a session to allow for this to happen have been very intense. The anticipation leading up to the session is all consuming and not long after the memories become very erotic. Even the second portion of the session after 'recovery" seems somehow more intense and vivid. Yet, while it is happening, it is very much a "what the hell was I thinking" sort of thing.

I know I'm going to hate that part of the session and yet I keep getting drawn to it. Anyone else have experience with this sort of dichotomy?

Yes I have. There are different types of masochists. One type achieves subspace almost mechanically through pain. However others such as you and I approach the Mystery of Pain in a more complicated manner.

It is definitely the tens unit. The penile and anal insertion, at the same time, is a roller coaster ride. The automatic setting is seducing at first but gradually increases in intensity. One of my favorite Dommes wires me up to this while going to work on my nipples and teasing me with her feet. It is everything all at once. I love it when it begins but am relieved when it is over.

When I am on the receiving end of a bare bottom spanking, the first part of it is all pain and no pleasure. The pleasure is gradual with the rubs to my ass as it heats up. By the end it is all a twisted version of pleasure. It reminds me of swim lessons as a kid. Jumping into a cold pool is the furthest sensation from pleasant. After a few jumping jacks and my body temperature adjusting, it was invigorating. Maybe all good things come with a little bit of dread.