Skin Hurts

After doing about 5 strecthes only lasting 10 seconds, even though the flaccid is longer why is it my skin stings when I touch it and when I continue stretching it?

You are probably stretching the skin more then the whole penis. I start feeling discomfort when I grasp my unit more towards the shaft. Try pulling as close to your glans as possible, that solves the problem for me.

I pull the skin back and grab the head (or just under the head) - I’m uncut. Not because my skin used to hurt (maybe only with SD/BTC stretches) but because it kept slipping.

Try this: westla90069 - BIB Hanger useful for manual stretching