On day 96 I had a weak moment that resulted in an orgasm. I was dry humping Mistress ( still in my cage and underwear ) and she gave me permission to try and get off as long as it was only a ruined orgasm. Once she gave me the green light I got a bit more into it, not fast like a jack rabbit just pressed up against her with more pressure and concentrating a bit more. At first I thought this feels good but I don’t think it will be enough to get me there and than Mistress began to touch me more. She was just running her fingers up and down my back but that was all the extra contact I needed, in a matter of seconds I found myself at the edge and over.
I don’t know how to explain the experience, it wasn’t a good orgasm but it didn’t seem like a ruined one either. I did feel one spurt but the rest just seemed flow out instead of squirt, the size of the mess on the bedsheets is what made me believe it was more than a ruined orgasm. I have had ruined orgasms in the past but it’s not something we practice, most of my experience is with teases going too far and me not being able to hold onto the edge.
At the time I convinced myself it was a ruined orgasm but as I thought about it more the next day I started to consider it a fail. I’m rather disappointed in myself for letting it happen, I was so close to the finish line that I should of avoided stimulation for the last few days. I’m still proud of myself for making it that long but sad and mad for not reaching my goal.
I’m still locked up and tomorrow is my 100 day marker, as for what’s going to happen to me I’m not sure. Mistress hasn’t gave any information on how she feels about my failure. I personally don’t think she will make me start all over from scratch but she could surprise me with that. As much as I don’t want to dive into another 100 days right now I think it would be appropriate punishment for failing that close to the finish line. As always only time will tell
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