So I did this last night before bed! To spice it up, I also wore a prostate toy inside me (which made me continually move my hips throughout the day trying to cum in frustration) and watched a hentai movie (which lasted almost the perfect amount of time).

Since I needed to hold a tablet with one hand, I alternated nipples each time (left for the first 5 minutes, right for the next, etc.), but I really pinched/twisted and abused them. They're fairly sore today, and they were definitely a bit puffy after.

Each five minutes I'd roll and do the ball slaps. Some of these hurt! I rolled 4, 4, 1, 6, 3, and a 4 from what I recall (it's several hours later, but I think that's right to my recollection). So that's about 110 ball slaps. Any that I felt were too gentle, I repeated as well, making sure I could feel them all.

By the end, my nips were sore (still are) and my balls were a tiny bit, and with the prostate toy, I was just frustrated. I desperately wanted to cum with no way for relief. I even remember reaching down to stroke my cock and feeling it caged so I couldn't... Best I could do was tickle my taint a few times, but it's not like I can cum like that. This was fun - thanks!

So after completing all the others, I did Paladintwk's version last night, and my god was it intense - thank you!

After already a fair bit of anal play from my Monster Quest chastity tease, I stuck in the rotary + vibrating prostate vibe and turned it on fast rotation + pulsed vibration. I layed with my legs above the headboard on the wall and a pillow between my ass and the headboard and balanced my wand vibrator on it so it rested at my perennium and the underside of my balls. Every few minutes when I wanted more intensity, I'd hold it and press it into my perennium. I also had a timer where I'd change settings every 3 minutes to go through all 20 settings. (I must have not pressed a button hard enough once, as I ended up having to do 63 minutes instead of 60.)

I managed to have my first sissygasm holding it pressed to my perennium only a few minutes in. It was intense, without all the relief of a normal orgasm, but definitely a feeling of being emptied that was satisfying in some ways, and almost painful/uncomfortable in others. I made sure to keep holding it through the orgasm when it got oversensitive before balancing it on the pillow again...

Before too long (maybe 20 minutes into the hour), I had another sissygasm. These were fascinating to watch as the first one bubbled over with some cum (which I scooped up on my hand and licked up), and this one I was a little softer and the cum bubbled into the translucent purple cage, trapped with my cock. It was really surreal to watch - it looked like my cock was in a mini-smoothie-maker with cum sloshing around it. Again, the cum itself was uncomfortable and a mix of pleasure/pain/overintensity, but some sense of relief at finally cumming.

At this point, my legs started to feel sore and seriously shake to the pleasure against the wall as well as being up for this long. I seriously wondered how I'd complete the hour. I kept watching porn (which I'd been doing the whole time) and by the last 10 minutes or so, while struggling to keep my legs up and still shaking pretty intensely, I managed to hold the vibe against my perennium firmly and sissygasm a third time, adding even more to the sloshing cum smoothie (similar level of uncomfortableness as before, though definitely less coming out at this point).

When I was finished, I was fucking EXHAUSTED, after releasing three sissygasms full of cum into the cage. It was SO HOT to cum this way - I don't think I've ever cum from anal + perennial stimulation alone, with my cock locked away and untouchable. I'd cum from direct vibration against a cock cage, but never like this. Despite all the cum (sort of a ruined orgasm, though some pleasure was had, but some uncomfortableness as well), I'm just as horny today as if I hadn't gotten to, paradoxically.

I carefully stood up and was able to catch most of my cum load as it ran out of the cage in my hand, which I of course licked up. I cleaned up the bare minimum and passed out in bed, sore and exhausted but content. My cock feels a little sore from the cum still on its flaccid form - I look forward to showering and cleaning it well and the inside of the cage tonight. This was fun, if challenging!

That finishes all the dares in this thread. It's been ~10 days of chastity so far when I had only planned for 7 (and it's my first 24+ hour experience with a cage ever!).

At the moment, all I have are three rounds of Monster Quest to get through in order to earn my release, though that's proven more difficult than I anticipated (as each loss adds another 15 minute session). Technically, it's possible I could do all three tonight, if I don't have any/many losses, but that's probably easier said than done:

https://www.getdare.com/bbs/showthread.php?t=340457

I suppose this thread also remains open for more before-bed teasing suggestions using the toys listed in the original post until I am released. I'm so close to getting out I can taste it, but at the same time nervous because I'm not out until I'm out!