So my KH called me up to our bedroom and told me to break out our fleshlight masturbation sleeve. We have one open on both ends because we both like to see the head poking out. She instructed me to masturbate while she stayed fully clothed, observed, but didn't touch. After awhile she asked if I was getting close and I said yes. She then told me "I want you to show me a ruined orgasm in the next two minutes. If you fail to show me a ruined orgasm or have a real orgasm I will take away your chastity cage for a week." I am really liking chastity so it was a strong motivator. I worked feverishly at it and would stop worrying about going to far. This go like crazy and then stop kept repeating itself 3, 4, 5 times, but I didn't have an orgasm ruined or otherwise. We hit 30 seconds left and she was counting down by 5 second intervals. I reached a point where I thought it was right and I stopped all stimulation, the sleeve was still on my penis, but I wasn't touching it. A full five seconds passed with no stimulation and I had the same internal feeling like my last ruined orgasm. Here's the thing though, instead of dribbling out like last time, it shot out. I was laying on my back and I had three or four solid spurts that went as high as my shoulder. Pre-chastity north of my belly button was rare. So my KH and I are just looking at each other like what the heck? She asks "did you just cum for real?" I'm like "I don't think so". The precursor and post orgasmic feeling felt like a ruined orgasm. I had no let down after and I was still raring to go, but the actual orgasm felt more like an orgasm. So I'm really confused, what the heck just happened? Was it real or was it ruined?
If you stopped all stimulation at he point of no return, then I say it was ruined. Should have felt something less than satisfying.