(Okay, this first request was by @Muli4)
Bendy's POV
"You have to! Remember? You have to do everything I ask. So just put it on." Cuphead glared at the frilly dress in my hand's with his hands crossed, looking like I'd just asked him to do the impossible.
"No way! I want to keep my dignity thank you very much!" I laughed, shoving the clothing into his arms. "You never had any dignity to begin with. It's just a day Cups. I'm sure it's not that bad."
He grumbled but took the outfit anyway, walking upstairs to change while Mugs and Boris laughed from beside me. This had all started when we'd just finished lunch and made our way to the living room, about to watch some TV when the doorbell rang and a package came. One that I immediately knew the contents of and that had started this whole drama.
"Why do you even have that by the way?" Boris asked, tilting his head to the side while I waved a hand dismissively. "I ordered it yesterday with my phone at the dance. After Cups had lost the bet I had the idea to make him wear that, so I bought it online."
"Woah." Mugs looked at the now-empty box on the ground. "That came fast." (that's what she said (I'm so sorry)) I nodded, smiling at the sudden profanities being shouted from upstairs. "It's because I got the one-day delivery. It cost extra but it was so worth it."
There were footsteps down the stairs and we all turned our heads as the figure appeared in the door. When my eyes connected with Cuphead I think I died on the spot. I'd seen the outfit before obviously, I bought it! But seeing it on him was something else.
"Are you okay, Bendy?" I vaguely heard someone say but it was all just background noise as I stared at him. Black and white maid outfit, lacy frills and a black pair of high heels with laced stockings riding up his lithe legs all the way to his thighs. "Bendy? BENDY?" I turned at the shout to see Boris right next to me, a tissue in his hand.
"You-You're nose is bleeding." He explained at my dumbfounded expression and I brought my hand up to my nose quickly, bringing it away to see it tainted with red blood. "Oh..." Still in a stupor I took the tissue from him slowly and brought it to my nose to prevent more bleeding, turning my attention back to Cuphead who was angling his legs together to cover as much as he could while readjusting the headband.
"This is so stupid. I feel like a moron." He pouted and Mugs laughed, bringing out his phone and snapping a picture. "Blackmail. Also, you are a moron Cups."
Cuphead, who I couldn't tear my eyes from, had an unimpressed expression on his face despite the pink blush all over his cheeks. "Hardy har Mugs. Very funny. Seriously though why is the skirt on this so short! Do I really have to wear this all day?"
My mouth was moving before my brain even had a chance to catch up and I let out a very quick "yes," In response to his question, feeling my own face feel hot at my reaction. I coughed after my squeak to cover it up. "You have to do whatever I say so yeah, you have to keep it on for the rest of the whole day." This time I spoke more sensibly, managing to get my words out right.
Cuphead was covering as much of himself as he could just by his stance and by crossing his arms when he sat down next to me, yelling out a string of swears as the tiny skirt he was wearing rode up his ass even more.
"This is so embarrassing." He whined out, pulling on the stubborn fabric to try and save the small amount of dignity he might have had left.
His stunning face blushed an even darker red at Mugs and Boris' hysterical laughs while I just looked down at his exposed thighs, feeling more blood run down my hot nose. "I'm so gonna send this to everyone!" Mugman laughed out, staring at his phone as Cuphead lunged forwards, trying to wrestle it out of his hands.
"Don't you dare! I'll never be able to go out in public again!" I stopped. And I think my mind must have stopped working because as Cuphead had lunged forwards he'd also exposed the white panties I'd also made him wear to me accidentally, giving me the full view that made me stop working as my face grew even hotter like a computer that had just crashed.
Boris looked over in my direction and Mugs and Cups squabbled over the photo, now looking concerned. "Are you okay Bendy? You face looks really red." I nodded stiffly and swallowed thickly, trying not to dwell on the image I'd seen briefly. "I'm fInE." My voice came out cracked and high pitched and Boris sniggered at my despair.
I coughed, turning my head away and hiding my shame in my hand, dying into the couch while wishing it would swallow me whole.
"Someone put me out of my misery." I moaned out, voice muffled due to my face now being buried into the couch. I heard Boris laughing somewhere behind me and I just groaned louder, also hearing Cuphead yell in dispair. "No! How could you!? I'll never be taken seriously again." I looked up to see that Mugs had posted the picture in the middle of the squabbling they'd both been doing.
My phone buzzed inside my pocket and I pulled it out to see mugs' post, a clear picture of the frilly short outfit Cups was wearing, looking embarrassed beyond belief with ruby red cheeks. I wasn't ashamed when I saved the picture to my gallery, smiling to my myself when I realised I'd be able to look at that for the rest of my life.
You know, and blackmail him over it too.
(I know, I know. It's been a long time. I actually did this a while ago but then lodes of stuff happened and I was super busy with school. But I'm here now and I hope you all enjoyed this strange chapter. Thank you for the suggestion @Multi4 I hope this was satisfactory.)