1) Have you been spanked much in your life?
I would say no. I was spanked a few times as a child by my parents for disciplinary actions and such. I've been spanked quite a few times ever since I found it arousing but sadly not by anyone but just by myself, even though it of course has been ordered by other people.
2) Describe the background of the hardest spanking you have taken.
I don't remember too much about the background of the hardest one I've taken, but I do believe it was before getdare, and this is where I kind of don't do this dare complete justice as it was delivered by myself and it was just something to do.
b.This isn't exactly a hard spanking but it's just something I like to relate to. The background of this spanking was I was temporarily subbing under a Mistress where she had 24/7 control over me four a couple of days and I was just her fucktoy. She later became a more full-time Mistress but since then our time together in that capacity has passed.
3) List the conditions of this spanking:
I think it may have something to do with a dare. I don't quite remember as this was a long time ago and like I said something to do when bored plus I enjoyed sending pics to my then Mistress at the time.
b. The conditions of this constant spanking was a rule of hers instated. That every time she said "good boy" I was to bend over and spank my ass ten times to remind myself that even when I was being good, I was still her bitch. If she said very good boy, it would be upped to twenty.
3a) Implement used? (hand, paddle, cane, etc.)
I used a leather belt for most of it if not all of it.
b. At least see for this particular rule I've used a crop, a hairbrush, two ping pong paddles, just whatever I wanted as long as it hit with a bit of force.
3b) Force used? (gentle, medium, hard, extreme)
Judging by the fact that my ass was red after I was done I'm pretty sure it was hard, but not extreme I don't want some of the bruises that I've seen.
b. Always as hard as I could go. I wouldn't say extreme, even though if she was actually the one administering them, they would be.
3c) What were you wearing? (jeans, underwear, bare, etc.)
I almost never get a spanking unless it's bare-ass. I'm pretty sure I was naked at the time as I usually was when speaking to my Mistress although I don't think I was at the time.
b. Most of the time I was mostly clothed with my pants and underwear down around my ankles, but when I first got this rule I was completely naked.
3d) Who did the spanking & their gender? (self/other, male/female)
Myself, male.
b. Same myself, male even though this time it was instated by a Mistress.
4) What was the number of spanks you took?
I think it was upwards of 100, in fact it might have been upwards of 300, like I said it was a long time ago I don't remember much of it.
b. Every time she said those words it was either 10 or 20 at a time depending on if she said "good boy" or "very good boy"...she took pride in saying these phrases a lot and I honestly had no objections. 
5) How long did it take for all the soreness & sting to go away?
Honestly, don't remember.
b. It never really lasted too long because it was such a small number.
6) What was your reaction to this spanking? (anger, tears, arousal, etc.)
Arousal, it hurt my ass was red but I did it out of boredom and I felt excited to show a picture of my red ass to my then Mistress.
b. Always arousal, without a doubt, my favorite rule I've ever had to this date.
7) From the implements you have experienced which are the least and most painful?
Least painful I'd probably say a ruler and the hand as it seems to hurt my hand more than my ass. Most painful my ping-pong paddle or a hairbrush. I can't wield a belt as well as I used to but it does provide a nice sting to it too.