Happy Boxing Day, all. While it’s a not a holiday we celebrate in the US and has become more akin to Black Friday elsewhere, it is still a named day and it sure as fuck sounds better than a regular “happy Monday” that we have a chance of hearing 52 times more after today before starting another year. Axel and I are back from a week in the desert with friends which was an amazing time, but we both missed the boy and we also missed what would have been our first white Christmas at home. Until his kid grows up a bit more we want him to never miss a holiday where they can be together, so separate trips will have to suffice until then. But, for now, we are back and the world is right as he is under my desk as I type this happy as he can be (as am I too.)
Anyway, if you are a long time follower you will know that once a year I give Jack the option of whether he wants to ejaculate on New Year’s Day, which will serve as his orgasm for the year, or decline his chance as a tribute to the training he has and continues to receive. There is no wrong answer as this annual choice is his and almost the only one he will ever get when it comes to his penis and ass, aside from those rare days I let him choose whichever plug he wants to carry that day though I sometimes make him double the size if he picks too small. On January 1, 2021, he decided against coming, though that was only about his third month in chastity and I am not sure he thought I was as serious as I turned out to be. On January 1, 2022, he also chose to not partake in the pleasure as he decided that another year locked would only help him grow in his slave role and I can honestly attest that it has. He was very aware that he was giving up an entire year to the titanium in his pants, but he owned that and, from what I have gathered, does not regret it, though I will admit to not having ever asked him if how he feels about it one way or another now, as it doesn’t matter to me anymore honestly as the decision was made. Also, I am a bit worried that if he did regret it, I’d probably like it so much that I might not be so kind now to remember his 2023 choice but I digress.
The 2023 choice will be presented to him today and he has until 6pm on New Year’s Eve to tell me his decision. As I mentioned, I will not feel like I failed if he says he wants it or not, as he has exceeded all wishes in the chastity area that I had specified for him. And, just to be clear, if he did chose to come, this would not be ruined or through the cage or anything of the sort as he has earned it. We would do our best to make it as sexy, hot, romantic and down right dirty as he would want it as that time, unlike everything else with us, is for him (and a bit Axel who really wants to see him come).
So, the next post will be Jack having decided, explaining why he agreed to another full year locked in my cage or why he wanted to reset the clock with the one, amazing, orgasm he has earned.
Curiously, what would you do in this situation? What advice would you give Jack?
He will see you Sunday with a full report of his 30 minutes of pleasure or sooner with this denial of his right.
Again, Happy Boxing Day.
The Drew Duality 
I’d choose to have a vibrator applied to the cage until I came. I don’t think those of us permanently locked should come by stroking or similar sensation. JMO.
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But choose wisely, for the true grail will bring you life, the false grail will take it from you….or something like that is a line that comes to mind. Indiana Jones and the last crusade I think is where it comes from. Anyway, the choice, as I see it is to have an orgasm. Nowhere in the guidelines have I ever been given the option to actually touch what doesn’t belong to me. Maybe not so coincidentally, I asked last year or the year before that if I ever were allowed to come that I wouldn’t be allowed to actually touch it. Of course, he readily agreed to the no touching by me part. 🙂
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Good point and now an option.
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I’m really curious to read your next post, to learn Jack’s decision.
I can’t help but think, after so long, that an explosive, delicious orgasm would ignite the cravings. (When I see Sir and am allowed to pleasure him with my mouth I become a cock greedy slut for weeks after. That’s harder than sitting in the status quo of waiting for him.)
Sending best wishes to jack in his decision making. And I hope you enjoy his choice to the fullest.
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I do think I find some quietness in the waiting. Ebbing and flowing of the craving of a sexual nature is expected. It’s ever in the background. Regardless the bond and craving to be the best slave my Master could possibly train me to be is more my drive than the ejaculation part. Regardless, the burden of choice is for once solely the slave’s. One I have been thinking about for a year. One I have already decided, yet not officially decided, for the record, just yet.
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To be stroked would be an awesome gift so that Jack would be aware of what he has been missing. After a year its cock should be extra sensitive. I would want post orgasm torture to experience as much as possible while unlocked. Possibly even whipping of the cock. As much sensation as possible.
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To this extent, I have experienced a full body, mental orgasm, complete with that post orgasm calm, except the actual ejaculation part. I’ve leaked lots (in relative terms for me. I am typically not a leaker, so when I do, it feels like buckets. I fucking love it). So I’ve had better than just physical sensations I’ve never had until I chose to give all of me to MY Master. Part of me thinks a “normal” orgasm would just be quite underwhelming at this point. Part of me also thinks you never know unless you try.
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You are right, a normal orgasm might be underwhelming at this point. But post orgasm stimulation could be quite overwhelming.
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I’d say let him have the biggest baddest orgasm ever. But what do I know?
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See above. Lol. The most intense orgasm I’ve ever had involved no physical ejaculation at all. So maybe I need a better definition of biggest, baddest orgasm ever.
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I have many thoughts, all of which are influenced by my position in life as a Dom. But I will try to be empathetic to Jacks plight. Apologies in advance for what may seem like just random thoughts.
As you said you have no preference to the outcome, then the consequences of the orgasm will be for Jack alone. In some ways, a true gift from his Dom, the ability to have a choice. But do slaves really value choice? Or by their nature do they find the absence of choice the most fulfilling? In which case is this truly a “gift”? ( my word, not Drew’s)
In our lifestyle slaves serve by choice. Although some may enjoy enforced slavery, our society and common morality do not allow for that form of non-consensual slavery. Jack chooses to serve, and gives control of his body, mind and soul to his Master, for many what would seem an extreme decision. But I suspect it is the extremity and intensity of the lifestyle that, in part, appeals to Jack. To create the life of a true slave, to give up all control and all decisions to his Master. There is a purity, a simplicity, to that kind of life. And to live that life without physical sexual release is an extension of that purity, that simplicity. Curious why Jack would chose to add an imperfection to his otherwise perfect slave life.
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I love the thought you have put into this. I think Master’s lack of preference to the outcome is a way of letting me know that the answer I chose is neither right nor wrong. It only exists. As I do live in the muggle world, my work worlds are filled with literally life changing choices. So yes, I do value choice. I also find the absence of choice quite fulfilling and that absence allows me to focus on one thing, service in whatever form Master chooses. So, if his choice is that I make one choice, service is my answer? Framed in such a way, either answer I give is service because he has allowed me one choice. Either answer is fulfilling to him, I believe.
Also, I have made the ultimate choice to give every part of me to serve him, physically, mentally, emotionally. There is something so pure and simple and incredibly, perfectly imperfect in that, I wouldn’t see a choice to orgasm to be an impurity, as the choice was given to me to make with a mind that I have given to my Master. Thank try for your rambling, as you called it. It allowed me to ramble and somehow it has filled a titanium cage with a dick my Master owns and reminded me how a slave and his Master can grow love and trust from full submission.
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I would choose to have an orgasm since (speaking as if I am boy Jack for a moment here) my Daddy wants to see me orgasm and my Master does not have an opinion one way or the other. Back to myself again. I would do it chained spread eagle. Being teased and on edge for a few hours then at the stroke of the new year finally the release
Before the cage is placed back on.
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I would put a tick in the pro-orgasm column given the fact Daddy wants to see you orgasm Jack. I am enjoying reading all these comments from everyone who is much further along on this journey than I am. Slave Samuel
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