Hey Bubblegum, I've got a dare for you:  do a full shift at work wearing a buttplug. Bring more than one, and shift to a bigger size each break you get!

Did this on Wednesday. I had a night shift, so I thought it would be fun to spice it up a bit. I've got four different plugs at home, but two of them are the same size so I brought only three with me. Perhaps I should buy some more for the next time... (˵ ¬ᴗ¬˵)
Since the dare didn't specify when to wear the plug, I thought it would be fair to take it at home right before leaving. Fuck what an idiot, I had to drive! ◕_◕
Anyway... I started preparing myself at 6 p.m.: pulled my pants down, got on my couch and gave myself a little flick of encouragement. I felt sooo sexy right then! I grabbed the plug—a small pink one, silicon, t-shaped, around 1 inch wide—lubed it up and pushed it in. I must have been a good girl cause it fit like a glove! (˶˃ ᵕ ˂˶) Gave myself a little spank and pulled up my pants, ready to go to work.
I'm used to walk with it around the house, but when I sat at the wheel I realized I made a mistake: I kept feeling it poking at my bum! I couldn't drive like that, so I had to pull it out and... Well... (⸝⸝> ω <⸝⸝) Sucked at it like a lollipop, deciding that if I couldn't keep it in my ass I would hold it in my mouth instead...
It felt so hot, my tail wouldn't stop twitching!
I made sure to park the car in the farthest, most isolated parking lot I could find from the hospital, so I could slip it back in without anyone noticing.
I walked into the building swaying my bum like a bitch in heat, but quickly lost my confidence once I reached the changing rooms. (⁄ ⁄•⁄-⁄•⁄ ⁄) So many colleagues! I had to be quick, cause I wasn't sure no one would notice the pink base poking beneath my tail.
Luckily my scrubs are way less revealing, and soon got comfortable enough to get to work. For the first hours it was pretty normal: I got into the flow and soon forgot I was wearing a plug at all. ( ˘ ³˘)ノ°ﾟº❍｡
That was until my break...
It was around midnight. I got into a bathroom, and stared at my dumb self in the mirror: I was giggling like an idiot... Pulled my pants down, cunt puffy and dripping, and switched the first plug to the second—a metal one, 1.5 inches or so, shiny and with a little pink jewel on its base. I felt it stretching me a bit, this time clearly feeling it forcing against my bum. I licked the pink one clean and stored it in my pouch, getting back to work walking a bit funny.
This time every step was hell—the plug shifted, pressed deep, my insides kept pulsing like crazy. My tail kept twitching as I shuffled through beds, dodging looks as best as I could. The worst thing? I KNOW some of them go straight to my bum. (ʘ‿ʘ)
Anyway, I knew this was hard, and I knew the next level would be harder, so I decided I would take my last break only a bit before leaving.
The dare didn't say the breaks should be spread even so I say it counts. ☜(꒡⌓꒡)
I did my best to ignore the plug, working like a soldier, but around four in the morning I was pissing myself so hard I decided I HAD to take the break.
I took out the buttplug as soon as I sat on the toilet, feeling relieved for the blood flowing back freely. I massaged my bum a bit, feeling it so tired it would give no resistence at all. (◉‿◉)
I looked at the last plug a bit scared... It was sitting right in front of me, on the sink. Black, slick, an absolute beast of a toy. I swear it was way more than 2 inches... But some part of me wanted it BADLY: I was looking at it like a kid in front of a cake, drooling like an idiot with eyes bigger than my stomach...
I felt my cunny agreeing with wet approval, so I did just what any good girl would do... Lubed it up and pushed it in—shit, it stretched my ass so much! A sharp burn melting into heat. My tail shot up with an "eep", and I felt it shifting slowly, my bum doing its best to adjust to its size. (๑﹏๑)
Luckily I only had to work one more hour before I could leave and get back home.
Do I need to describe how miserable that hour went? Just picture this: at one point one of the PATIENTS asked ME if I was ok.
Like, HELL NO I'M NOT! Do I look ok!?! I've got a freaking fist up my bum, how do you think it feels like?
"Peachy! Thanks for asking! Gotta go now!" (ﾉ◕ヮ◕)ﾉ*:・ﾟ✧
When my shift ended I was a mess. My legs were shaky, I was soaked, and just as I got into my car I made the mistake of sitting! A wave of pain hit my spine, I honestly jumped like a cat splashed with water... (๑﹏๑)
I collapsed in my car, tail limp, still stuffed. Horny, pissed, alive—this dare fucked me up and I loved it. (⁄ ⁄>⁄ ▽ ⁄<⁄ ⁄)
I pulled out the plug marking the dare DONE, and I think my bum has never been so grateful about something before. I swear, when I went there to assess the damage I found an absolute gorge! It was the first time I was wearing something that size, and boy did it break me... ( 0 _ 0 )
Needless to say, I wanked myself dry twice: once on the spot, then writing this report.
Thanks for the dare, Bubblegum off!
( ˘ ³˘)ノ°ﾟº❍｡

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:iconnyxapnea: made this sketch for me a couple of days ago, on the couch while I was reading Werewolf 5e to them.
Can't wait to try it out!
I got the idea for this pic looking at a model online, thinking I love how nurse scrubs drape down slightly covering the waist even when pants are down.
This "see, don't see" game turned into my request to draw Kat looking at her bum through a mirror, wearing her work outfit. A buttplug was just the perfect excuse for this pose, and well... Once I saw the finished sketch I just HAD to write something about it :3