Day 65

 I have now set a new personal best, 65 days without an orgasm or release ( besides pre-cum). I am really proud of myself and I feel accomplished now that I’ve passed a milestone. At least 35 more days to go and that still seems like a long time even though I’m over 2/3s done.

Frustration and desperation is starting to set in more now and I always seem to have sexual thoughts on my mind. The last few play times I’ve tried negotiating with Mistress to see what’s allowed and her definition between orgasm and release.  I was hoping maybe a ruined orgasm might be allowed but not so much. Mistress more less said anything more than pre-cum could be considered an orgasm,   we haven’t really played around with ruined orgasms (on purpose) so Mistress hasn’t perfected the act to guarantee that it would be a ruined orgasm and not a real or full orgasm.  Yesterday Mistress put her foot up to the cage and said I could try to make myself cum and she wouldn’t count it as an orgasm but I still had to pay the price for below the knee. It crossed my mind but I really don’t think I could of made myself cum from that with the cage on.

Milking has also been a subject of conversation lately. We have played with it a bit in the past but I don’t think we ever had success. Mistress said she would accommodate to me but I have to ask her for it and be specific about what I’m asking for. We do have toys for milking and for pegging and that’s why Mistress wants me to be specific. Our experience with both activities are very limited and have never resulted in any form of release in the few times we have tried in the past. If we were more experienced with those activities and we knew what the outcome was going to be I’d have no issues with asking. As of right now I have mixed feelings because I don’t know if I’ll get any release or possibly too much of a release and push the boundaries of an orgasm.

Mistress did confess to me that a wet dream will result in punishment but she won’t consider it a fail to the 100 day challenge. Before she confessed this I wanted to be milked to avoid a wet dream but now that I know it won’t be a fail my desire to be milked only sets in while we are playing and my frustration level is at its peak. I know Mistress would prefer me to go the full 100 days with out any release so as of right now I’m refraining from asking for a milking just to make her proud, but in the heat of the moment as my frustration builds so does my desperation.  I just need to stay strong and not give into temptation in the next 35 day.