My KH summoned me to the bedroom and had me grab our Fleshlight. We keep it open on both ends so we can see the head sticking out, since that’s what we prefer. She told me to masturbate while she watched in full clothes but kept her hands off. After a bit, she asked if I was nearing the end, and I said yes. Then she gave me an ultimatum: “I want you to show me a ruined orgasm within the next two minutes. If you don’t deliver a proper ruined one, or if you have a real climax instead, I’ll take your chastity cage for a week.” Since I’m really enjoying being in chastity, that threat was quite motivating.
I went at it with intense focus, trying not to worry about going too far. It felt like I would go over the edge and then hold back, repeating this cycle three or four times, maybe five, but no clear result yet. With thirty seconds left, she started counting down in fives. I reached what seemed like the right moment and ceased all movement; the sleeve stayed on my penis, but I wasn’t actively touching it myself. After a full five seconds of stillness, I got that familiar internal sensation from previous ruined orgasms.
Here’s where it gets interesting: instead of leaking out as usual, it shot out. Lying flat on my back, I had three or four strong spurts reaching up to shoulder height. Before getting locked in this cage, shooting past the belly button was uncommon for me. My KH and I just stared at each other in disbelief. She asked, “Did you actually cum?” I replied, “I don’t think so.” The sensations before and after felt like a ruined climax—no letdown afterward, still feeling ready to go again—but the actual release seemed more substantial than usual.
So I’m left puzzled; what exactly happened? Was it genuine or was it ruined?