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.

Day 50.

Potentially half way done my challenge and 11 days away from a new personal best.

There isn’t much to write about since normal life has been really hectic lately. We are kind of in a play time drought right now. We have only played once in the last couple weeks and it was more of a “ give me an orgasm real quick while the baby is asleep” situation. Nothing too special a bit of foreplay to moisten things up , than rub Mistresses clit until she came. I received a bit of attention in the process and that’s all it took too drain out some pre-cum or chastity tears as I call them. Chastity tears is still the only form of release I’ve had so far which really shocks me, I thought by now I would of had a wet dream but maybe Mistress has put a scare in me about that.

I’ve been a really good boy lately, going over and above all my required chores and also taking on daddy duties. Mistress has noticed this and thanked me several times but I haven’t got much of a reward or even praise for it. A few weeks back Mistress kind of bribed me by saying “ if your a good boy all week I’ll put on something visually stimulating for your spankings”. Well I was good and she did, it was a black corset and thong.  It was sexy but she has way better outfits in her collection, I didn’t expect her best since my behaviour was only good not great. I’d say my behaviour has been between great and excellent for almost 3 weeks now and the lingerie drawer hasn’t opened up. I know I shouldn’t expect rewards for my behaviour but I’m starting to feel that all my hard work has got me nothing. Sure I’ve got verbal thank you and appreciations but after weeks of well above good behaviour I feel I need more than that as incentive to keep it up.

I don’t want this to turn into a big rant so I better wrap this post up. Thank you for letting me vent to you and hopefully I can write about something less negative in the near future. Please feel free to comment, I’d like to hear some feedback and if for some reason the comment section isn’t working let me know on OD ( I’m pretty sure that’s how all you readers found out about this blog).