Almost. Years ago she applied some kind of muscle relief cream to my dick while I was blindfolded and restrained. It took a while to ease the pain with soapy wash cloths.
Many times. We're into ballbusting and during sessions (about once a month) she insists on me being naked and she wears pointy stilettos. She kicks very hard and won't stop until I'm literally crying.
Not yet. It really turns me on to think about though. I don't think it would take much more caning by my Mistress for instance, as it's so painful. Unfortunately, I have high levels of testosterone, which is believed to inhibit crying, and certainly I very rarely cry. I managed about ten minutes when my parents died I think.
Prior to chastity, we were into bdsm play. It started with me as the Dom, then switching roles, and eventually her the Domme. A client of her business is/was a professional Domme before emigrating to America and became friendly with my wife. When she showed the business side of her home (dungeon) my wife asked a few questions to better understand the business for expense reporting and also out of curiosity. The next quarter some more questions led to an offer to show her how things were done and after she had my wife comfortable with various implements, had her bring me for a visit. I got a tour of her home and then a tour of her basement while my wife was suppose to review some files. Imagine my surprise when my wife walked in dress as a real Domme and ordered me to strip. I was tied to a naked to a cross and the Pro Domme gave my wife lessons on flogging, canning, and whipping. The Domme would show her a technique and have my wife repeat it on me. Some adjustments were made with stance, delivery method, and placement and by the end of the night I was sobbing like a baby. A week later, we were building a dungeon in the old wine room in the basement previously sealed off prior to us buying the house. It took digging out the dirt floor (leveling), rough plumbing a bathroom, pouring a concrete floor, and framing out the walls. Slowly we insulated, soundproofed, and finished the space and I started building the furniture. There are several nights a year when she still takes me from a defiant man to a sobbing baby and I do enjoy every moment when I look back.
Many times! During (BDSM) play the physical and mental connection is so strong you’ll find your inner soul and tears are inevitable. It is great and so healing. But also during personal talks if you can be open, honest and sometimes vulnerable. And both ways! It is okay to shed some tears together.
Right when we started 24/7 Chastity in early 2020 after about 60 days in chastity my Wife/KH allowed me umcaged and inside her. She rode on top of me to emphasize She was in control and the Dominant one. That orgasm was so emotional for me that I did cry while my body shook under her. Her reaction was mind blowing, She place a finger on my lips with a soft shhhh dismounted me and walked into the bathroom to expell me from Her. This was the first and only time I have cried at climax, it was beautiful and I will remember it forever.