In chastity and diapered 24/7 until the end of the month. Make it harder for me?

[LimitExplorer]

I was on a vacation with a (platonic) friend the first half of the month, and we shared hotel rooms, so I didn't masturbate at all during. Now that I'm back home, I figured I might as well try to keep that streak up until at least the end of the month, especially since it makes me more excited and willing to do fun stuff and try new things...

Then, I carelessly added the third rule to the cumulative Person Above AB/DL dare:

1. Loser wears diapers 24/7 for the rest of the month.
2. Loser can only cum in diapers.
3. There must always be a risk of the diaper being slightly exposed when in public.

The chance that I'd get boomed that early in the dare honestly never even crossed my mind; As it turns out, that was naive of me... Now I'm locked in diapers 24/7 until the end of the month, they have to be peeking out of my trousers at all times, and I'm in self-imposed chastity as well.

In for a penny, in for a pound, so I wonder if anyone wants to make it harder on me? Give me some tasks or rules? Anything within my limits is welcome - if you're unsure, just suggest it anyway.

I'll let you know if I accept your challenge and, if desired, can provide proof through my kik in the signature below.

[Sakurai]

how unlucky well I got something for you. You may only change when you have permission from someone too, and your only allowed to ask when your diapers are getting close to leaking!

[LimitExplorer]

Originally Posted by Sakurai

how unlucky well I got something for you. You may only change when you have permission from someone too, and your only allowed to ask when your diapers are getting close to leaking!

I've never had to ask anyone for permission before .
That'll certainly be a new challenge :-) thanks for the rule...

Now I need to find some benevolent people to talk to 😬

[LimitExplorer]

I had not really given it any thought, but it's pretty difficult to find people on GD to ask permission to when I get out of bed (in Western Europe)... I'm going to have to come up with a solution.

I considered asking people i know in real life to ask permission without telling them what I needed permission for, but that would never fly, they'd definitely ask what's up...

I'm afraid I ended up breaking the rule because I definitely wasn't going to go to the office with a wet diaper I'd been wearing all night... Sorry Sakurai!

For today, my way to get permission was to post in the Response time Kik dare, where I'd get permission if I responded in time. So far I had one that I decided shouldn't count because I hadn't gone to the office yet - too easy to win - and I got one that I didn't even get close to responding in time to; they won and I had to send them a picture of my diaper, which I did and frankly enjoyed doing

So now I have no permission yet (but also no need to change yet)...

Later today I'm giving a presentation in front of my colleagues - hope my diaper doesn't show, that would suck...
And after that I'm going to the gym. Not breaking my 24/7 diapered rule though! I'll just have to find a quiet moment in the locker room to change into my sweatpants...

[HomerJay28]

you should definitely wear a plug and ballstretcher while you are diapered at work, thatll remind you

[LimitExplorer]

Originally Posted by HomerJay28

you should definitely wear a plug and ballstretcher while you are diapered at work, thatll remind you

Thanks for your tasks, I'll try to get it done tomorrow, or otherwise on Thursday and report back to you .

Originally Posted by LimitExplorer

So now I have no permission yet (but also no need to change yet)...

Later today I'm giving a presentation in front of my colleagues - hope my diaper doesn't show, that would suck...
And after that I'm going to the gym. Not breaking my 24/7 diapered rule though! I'll just have to find a quiet moment in the locker room to change into my sweatpants...

Well over the course of the day I got a few more people messaging me on Kik, but most of them weren't playing the Kik response time challenge, and to make matters worse I responded to them too late each time anyway. I knew 20 minutes was going to be challenging with a day filled with post-vacation catch-up meetings, but I really underestimated how much time I would spend not looking at my phone today.

I still don't have permission to change yet... I do have some alternative ways lined up to get it, so I'm optimistic I'll be OK.

The presentation went without a hitch - I had a fairly long T-shirt on that hit everything well, though I did make some pretty loud crinkling sounds when I went to lean against a wall during the Q&A part...

After work I did go to the gym. I ended up waiting in the locker room for 5+ minutes, looking for a quiet moment to get out of my jeans and into my sweatpants without anyone seeing my diaper. I finally got a short window where there were only two people in the locker room, and I could find a spot behind some lockers that was out of their view. I guess I looked like the most never-nude guy ever to them, stepping away from where I was getting undressed just to change into sweatpants . Right after I'd pulled my pants up, someone walked in, so it was a really close call.

It also turns out that Tuesday evening between 6 PM and 8 PM is prime time for the gym (no shit, right?)... My sweatpants were really bad at concealing the padding between my legs, and I made a lot crinkling sounds with each rep I did on most of the machines, that I hope got drowned out by the music for the most part. (I could hear it through my earbuds though, so it was definitely noticeable to me.

The riskiest machine I used today was the shoulder press. Because you have to push weights up into the air above your head, my shirt kept riding up well above the band of my sweatpants. I don't think anyone saw anything, but there were so many people there that it's kind of guaranteed that someone must have.

Finally when it was time to get dressed the locker room was packed. I didn't want to expose myself in front of them, so I went to the toilet, took off the diaper, and then put it in my locker. Then I showered, and afterwards went commando in my jeans, back to the toilet. I didn't have permission to change, so I had to get back into the sweaty & wet diaper for the ride home .

Oh and I don't know why but when I went to shower the showers were all unused. I took the one in the far left corner of the shower room, and for some reason a dude decided to take the one right next to me even though there were 7 other showers available... I don't know if I accidentally gave him some kind of signal I wasn't aware of (or if he was giving me one I don't know about) but it was really odd to me.

I learned two valuable lessons through this whole ordeal:

1. If you're going to switch to your gym clothes in a locker room while wearing a diaper, you really need to act as if it's the most normal, plain thing ever. I'm bad at that right now, so I constantly looked like I was "up to something", which just drew attention to me. If I'd just nonchalantly taken my pants off and put on my sweat pants on as I would've if I were wearing boxers, I don't know if anyone would've noticed or said anything, but because I was acting so nervous it just made people look at me more and made me have to wait for them to leave before I could do anything.
2. Having dares to do or rules to follow makes going to the gym a lot more enjoyable. Honestly a pretty nice way to keep motivated :-).

[LimitExplorer]

So today was relatively uneventful - I didn't get around to doing @HomerJay28's dare, so I'll have to see about doing it "tomorrow". It's 3:15 AM as I write this and my alarm will be going off in 3 hours and 45 minutes, so I don't know if I'll have the time, energy and health to pop in a plug in the morning . In the worst case scenario I'll need to postpone that until Friday, but I really wanna do it, so no worries there.

I chatted a bit on Kik during my work day and kept up my 24/7 diapered challenge, with a short break to A. take a shower, and B. model some of my crossdressing clothes to someone on Kik that preferred the show be sans diapers. I guess I live to serve.

Tonight was my regular pub quiz night, so I went out drinking a bunch. I prepared by adding a stuffer to my diaper, but now that I'm back from the pub I'm definitely starting to leak a little bit... I still could pee more, and I still need to drink about 1L of water to stave off a hangover... I'll definitely need to change... Hopefully someone on Kik will be willing to grant me permission to do so




So my plans for Thursday are:

1. Keep being diapered
2. Survive another work day
3. Wash my gym clothes

I intend to go to the gym again on Friday. It occurs to me now that this will have some interesting implications if I do end up wearing a butt plug & ball stretchers that day. Clearly I've got some stuff to think about and plan ahead...

[LimitExplorer]

Nothing special happened today - I woke up with a bit of a hangover and had too little sleep to really get up to much during the day.

I have set a ballstretcher and my selection of butt plugs on my kitchen table, ready to use tomorrow. I know from experience that the ballstretcher can start to pinch really painfully after a bit (especially after moving around with it a bunch), so I'm curious to see how long I can hold out.
Being plugged at work seems like it might be fun - it will definitely be a constant reminder of my current predicament. :-)

I'm looking forward to the weekend. I have various fun things I'd like to do, assuming people will let me. I'll elaborate when the weekend is finally here.

[Sakurai]

I want you to go out for 2 hours with your new bag, and actually use it. so change yourself in a bathroom somewhere!

Have fun sir

[Legendary]

When you go to the gym you won’t change in to sweat pants you will change in to a skirt! Because youLOVE cross dressing

[LimitExplorer]

Originally Posted by Sakurai

I want you to go out for 2 hours with your new bag, and actually use it. so change yourself in a bathroom somewhere!

OK, I will try to find some time to go for a long walk or travel someplace and change halfway through. Thank you for the dare <3.

Originally Posted by HomerJay28

you should definitely wear a plug and ballstretcher while you are diapered at work, thatll remind you

Well I finally did this dare yesterday and it was absolutely disastrous .

I woke up a bit groggy and didn't have a lot of time to prepare, but figured I'd just go with the flow and attempt the dare. Quickly lubed up a medium-sized plug and put it in, and put some silicone ball stretchers on before diapering up and heading off to work.

For starters, being Dutch, I cycle to work every day. 20-25 minutes of riding a mountain bike with a plug in was not a very relaxing start of the morning. My ass was really sore by the time I got to the office .

After about an hour I went to the toilets just to take it out for a second. I was super super horny due to not cumming at all for over three weeks, so I foolishly also decided to quickly edge myself... Mistake!
I think the ball stretcher added just enough pressure to the mix that I went over the edge and came . I tried to ruin the orgasm as much as possible, but it couldn't stop me from feeling A) super disappointed in myself, B) empty inside (emotionally, I mean *wink wink*), and C) no longer very aroused. I always get that after an orgasm, but this was worsened by the fact that I felt like I'd ruined a great three week streak and let myself down.

I had caught my ejaculation in my hand, and as punishment I quickly forced myself to eat it all. Not something I'd ever done before. I think I liked it, but I didn't enjoy it as much as I would have if my disappointment with myself hadn't overshadowed the experience so much.

Because I was now not as aroused as I had been I didn't put the plug back in. I did leave the ball stretcher on for a bit, and since I didn't have any other underwear with me I also kept my diaper on.
After another 90 minutes or so the ball stretcher was really pinching my skin, so I took that off as well...

Luckily during the workday my disappointment subsided and my arousal returned pretty quickly. By the end of the workday I was already really happy to be in a comfy, pink diaper.

I think I may have to re-attempt the dare again another time, but:

1. I probably shouldn't have it in while riding my bicycle
2. I should prep more, with better cleanup and working my way up to the medium size plug instead of jamming it in first thing in the morning.
3. I should do it when my skin is less sensitive, so that I can hopefully last longer with the stretcher on.

All in all I still enjoyed the dare, but it didn't go as planned at all.