Most painful: My ex-fiance, that I adored beyond anything in this world, leaving me for a guy she was fucking, and to see her 12 months later on Facebook, 6 months pregnant in a bikini, holidaying on the Greek Islands with him all loved up and looking amazing, sadly carrying his baby, not mine.
Most cruel/ hurtful: My ex-wife and I going through an ugly divorce, and to try and fuck my life up even more... her telling our friends and family, her 'new' boyfriend was actually a guy she'd been fucking for years, with me knowing, willingly encouraging it and always watching while I masturbated. Plus following it up with, that I was a cuck, I had a tiny cock, I usually would cum within a minute or two, that I was very bi and loved sucking cock, especially while dressed as a sissy wearing panties, heels and stockings.
