Day 42. Yesterday was an unforgettable experience for me. An absolute core memory. Domina Penn greeted me with a wonderful surprise and proceeded to rock my world. I am so thankful for the perfect ending to a long, challenging, and profound journey and, even more so, for the journey itself!

Day 41. There is definitely some magic in chastity. I woke up this morning like a kid on Christmas morning. That sort of excitement, joy, and anticipation is a precious thing.

Day 40. I had to go to urgent care yesterday for a minor injury (I‘m fine!) and on the way there it occurred to me, “I really hope I don’t have to take my pants off for this!” Thank god it was a hand injury.

Day 39. I feel like i can finally see the light at the end of tunnel! Just 3 more days until the end of my Locktober (Longtober?) sentence. Of course, NNN is already here and I’m late to the party. What will that mean for my near future?

Day 38 This has been a crazy week which had the benefit of keeping me so busy that I haven’t really had a moment to think about my horniness. But this morning it hit me like a ton of bricks, thanks in large part to a message from Domina Penn. I‘m going to be feeling the edge of horniness all day.

Day 37. In the mornings, when I’m often feeling especially horny and pent up, sometimes I find myself just staring at my cage trying to remember what my erections looked like. I feel this deep longing in the pit of my stomach for a sensation I haven’t had in what feels like a lifetime.

Day 36 I’ve grown to oddly like the way my cock looks in its cage. Something about the way it presents my full balls, the way it just gently holds my soft cock while keeping it safely chaste, and of course the way it looks when my dick attempts to burst through its confines, red and throbbing.

Day 35. Picturing my key on Domina Penn’s necklace makes me so happy and is an image I return to frequently throughout the day. It is such an honor to be in her service. I cherish every pang of desire, every ache of desperation, because each one brings her presence into my life.

Day 34 There is a good deal of vulnerability in chastity. Of course giving your keys to your domina leaves you profoundly vulnerable to their whims. Today I’ve been thinking about the vulnerability of release, how there’s almost no demand I would refuse for it, how chastity has crumbled my defenses.

Day 33. Went for a long hike today and I could feel my heavy balls bouncing around the whole time. Luckily my panties we’re on the tighter side today and provided some support, but together they were a constant reminder of my chastity and current state of denial.

Day 32. 10 more days, that’s all there is between me and (extremely temporary) freedom. It’s a sentence I will gladly bear for the privilege of serving Domina Penn in person, but I have a feeling it might be the longest 10 days of my life.

Day 31. What an intense, frustrating, and wonderful month it’s been. The journey has been as rewarding as it‘s been agonizing and I’ve relished the opportunity to deepen my devotion to Domina Penn. It’s hard to believe I’ve made it so long and yet my sentence isn’t over…

Day 30 Not being able to touch myself has provided me the opportunity to really work on my training. Without the distraction of coming, I go much longer, pursuing any possible outlet for my horniness. I’m proud that I’m now comfortable taking my very largest toys for extended periods at both ends.

Day 29. I had vivid dreams of being unlocked by Domina Penn last night, which made it all the more frustrating to wake up still absolutely packed into my cage. It also makes me embarrassed to think about just how quickly I would come if she were to unlock me. Maybe just a touch is all it would take?

Day 28 The recent cold weather has had an interesting effect, numbing most of the pleasurable and teasing sensations I felt while walking to work in my panties. However, once I get inside and everything warms up, all the sensation comes rushing back and my cock quickly swells to bursting in its cage

Day 27 There’s no way to understand how it will feel to be this denied until you go through it. The horniness comes in waves, where the cage really just feels like a new normal most of the time, but whenever I let my guard down it hits me and can be nearly overwhelming. I find it best to keep busy!

Day 26. Somewhere along the line this month I seem to have developed a major praise kink. I’ve always enjoyed being called good boy (who doesn’t?), but never considered it a part of my kink. At this point the smallest compliment from Domina Penn makes me melt and I find myself chasing her praise.

Day 25. I woke up wanting a release so so badly, but while I was fantasizing about freedom I realized something. Previously, while staring at my cage longingly, I always pictured me jerking myslef off but these days I imagine a different pair of hands, yielding my autonomy even in my fantasies.

Day 24 I nearly had an extremely embarrassing incident on the train. I set my coffee between my legs and before I knew it the vibration running up the seat, my thermos, and then into the tip of my cage had me on the edge of coming. It happened so fast I barely had time to register what was happening

Day 23 Last night was hard, seriously hard. Domina Penn granted me the reward of attempting an anal orgasm. I was on the edge almost the entire time but after nearly an hour of wanting so desperately to burst and feeling sooo close I had to give up. I went to bed more frustrated than I’ve ever been.

Day 22. It’s wild how giving someone your key gradually but powerfully centers them in your thoughts. To be clear, Domina Penn has been living rent free in my mind for a while now, but giving her absolute control over my pleasure and even my arousal has dramatically intensified it. She owns my mind.

Day 21 Three weeks! Three whole entire weeks without coming or so much as really touching myself. I’m hornier than I even realized was possible. Even the slightest touch through my bars makes me moan. Its torturous, but I also like how slutty it makes me feel to be so easily stimulated and sensitive

Day 20. I think I’ve officially crossed over from general horniness to genuine desperation. How do I know? Last night, while cooking dinner, I caught myself gyrating against the kitchen counter. I’d like to say that I stopped as soon as I noticed…

Day 19 I was allowed to unlock for my weekly maintenance. While the chance to urinate upright remains a small thrill, I found that I missed my cage. I’m not entirely sure why yet; perhaps I’ve just grown accustomed to it, maybe I feel safe from temptation, or it could be the connection it provides.

Day 18. I’ve noticed that I’ve started leaking whenever I get the slightest bit horny. I wake up leaky and proceed to leave wet spots in my panties just from the pleasurable sensation of the lace rubbing against my balls while walking around. It’s humiliating but makes me feel soooo slutty.

Day 17. These edging sessions are driving me up a wall. I think about them all day long and then they’re over before I know it and I’m cramming my rock hard cock back into its cage, even more desperate than before. Which raises the question, do I have the will power to resist the momentary freedom?

Day 16. I like femdom porn as much as the next guy (ok, probably more) but while edging lately I’ve found my mind drifting to Domina Penn and all the kinky things she’s done to me. Somehow those memories and fantasies are all the more potent these days, more so than any scene I could find online.

Day 15. Two weeks of chastity has me on such a hair trigger that I can barely even touch myself while edging. By the end of the 5 minutes I can only last one or two pumps before needing to pull my hand away. It’s maddening.

Day 14. I managed to finally take my largest plug yesterday! It was a bit of struggle on the way in, but the sensation of it popping past my sphincter was euphoric. And then it felt amazing to be so full while i was edging, a heady cocktail of submissive slutiness.

Day 12. Pulling my hand away from myself when the edging timer went off took all my will power. I had to stop several times over the five minutes because i was just so sensitive and close. Stuffing my cock back into its cage afterwards was also quite a struggle, it just didn’t want to subside.

One thing I didn’t expect is for the cage to actually feel good. The gentle tug of the ring on my balls, the light grip of the cage on my shaft that quickly becomes firm as soon as I think about it. It’s a particularly cruel irony that the instigator and denier of my arousal are one and the same.

Day 11. Some stray observations: I didn’t actually realize that my balls could get this full. The weirdest part for me isn’t not being able to come, but the fact that I haven’t even had a full erection in nearly two weeks. And yet, my body hasn’t tried to get hard this frequently since puberty.

Day 10. I enjoy ass play but this week I have been craving it as my only form of stimulation, which is reframing it psychologically as a primary source of pleasure and I want to feel even fuller so I bought two new plugs. The first I took no problem but the second makes me sweat just looking at it 😰

Day 9. I woke up literally throbbing in my cage. I mean, I could actually see myself pulsing as my cock pushed through the bars of my cage. I don’t think I’ve ever wanted to touch myself so badly, but all I could do was lie there taking deep breaths until I was finally calm enough to go about my day

Day 8. I’d swear that my balls are getting heavier. They certainly feel tighter and faaaaar more sensitive. Every innocuous rub of my boxers or errant tug from my cage sends a teasing bolt of pleasure through me that I try desperately to not give away with my face.

Day 7. I’ve made it one week! While the challenge has only begun to ramp up, I’m genuinely proud of myself for this milestone. Now it’s just... 24 days to go. Well then, guess I’ll just have to take it one increasingly horny day at a time!

Day 6. The horniness is really settling in, like a growing warmth in my crotch that is making me feel increasingly needy. I’m so thankful that Domina Penn is letting me put my plug in today, so at least I have some stimulation even if it is ultimately unsatisfying.

Day 5. I somewhat regularly go 3-4 days without cumming because I enjoy the buildup of horniness, so the sensation of the denial itself has been familiar so far. However, from here on out we’re heading into uncharted waters. Definitely a little nervous, but mostly excited for new experiences.

Day 4. The first couple nights in chasity were uneventful, probably because I’ve been running pretty dry due to certain last minute pre-Locktober activities. However, last night I kept on waking up with my cage near to bursting. 1/2

Day 3. I’m not going to lie, I was initially pretty nervous to wear my cage into the office. It felt almost like the bright pink of the cage could radiate out through the fabric of my pants and I was hyper aware of the shape it made. 1/2

At first I was constantly scanning people’s eye lines to check if they were examining my crotch, but after a few hours I realized no one was noticing and the bulge was really only noticeable to me. Once I got over that initial fear it became thrilling, like keeping a personal and risqué secret 2/2

I woke up this morning still locked up, which turned me on. And there was nothing I could do about that, which also turned me on… I think I’m beginning to understand how this works.

Woke up and locked in this morning… quite literally. First day of Locktober, here we go!