I've had countless CBT encounters but the harshest had to have been while I was with my first wife. We'd been getting deep into bondage and S&M, each time she would push further limits on me. Skipping all the lead up, she'd advanced to the point where she enjoyed watching me being manhandled, even raped and abused by other men. The first 4-5 times were intense but great, it was the 6th that got out of hand. She'd found, or paid, 5 guys to rape and abuse me. The "rape" was intense and violent but it's when they'd lost their lust that it got bad. They began focusing on inflicting lots of pain to my cock and balls. As severe as it was, I at first enjoyed it but they didn't let up and became almost blood crazy. My cock was beaten, burnt, and even pierced until it looked like ground beef, the head was even split. My balls were just as bad with my scrotum being torn and my poor battered gonads hanging out. My genitals had at one point been used as target for a dart game and now someone stabbed each testes with a dart. My wife didn't try to stop it, in fact seem extremely excited about it all. Someone produced a knife and suggested castrating me and dicing up my battered cock and she was all for it. Thankfully one of the guys, apparently somewhat of a leader for the group, intervened saying the police would get involved if they went any further, even if my wife and I consented, and that ended that session. Almost miraculously when I went to the ED, the MD was able to patch me up and in a few weeks it was hard to tell I'd had so much damage done. More CBT followed but never to that extent again.

The most embarrasing situation I got myself into has to be when I stuck my cock through the glory hole in a public toilet wall & the guy on the other side stuck a huge hat pin all the way through my cock shaft. the pin was much longer than the width of the hole. He left. I was trapped there for over an hour unable to free myself. The 2nd most embarrasing has to be being suspended by my cock & balls on the landing at the top of a guys staircase. The cord snapped sending me headlong down the stairs. The result was I cracked 2 ribs & slipped 3 discs in my back. The ambulance crew were clearly amused by my predicament

define "worst". these sound more like "best", in my book at least.

My first GF and I loved CBT. We would play for hours on end a few times a week. She got that into it, that one night she tied me up tightly, hooded me, and branded her initial into the head of my cock. Thankfully her initial was the same as mine so now I have a "S" brand on the head to remind me of this night.

My worst CBT encounter was with a guy who did serious burns to my cock with a box knife he heated up on a stove flame and then cut into my cock. I still have scars around the base of my cock from that.

I've never been fisted before, and a guy I met kept trying to fist me. Lucky I wasn't tied up. Then he wanted me to eat his cum and I was like "No sir, I do not know you well enough for that."