Day 25 - Anal Training


The smell of coffee and bacon mingled through the air of the Gadget household as breakfast was sat on the table.  The inspector himself, Wynona, Penny, and even Brain were all gathered together, enjoying the most important meal of the day.  Yet all too soon, the peaceful scene was interrupted by the sound of a phone ringing.  Gadget continued happily munching on a piece of buttered toast as his girlfriend and niece shared a look.

“Um, Uncle… I think that’s the Top-Secret Gadget Phone,” Penny said.

“Ah!  Thank you, Penny,” he said, sitting his piece of toast down.  “If you’ll excuse me, dear.”  Wynona nodded as he got up from the table and walked a few steps away before he tugged the antenna out of his thumb.

“Hello?  What’s that, chief?  You’re where?  … Right away!”

Gadget looked around the kitchen, before walking over to the pantry and opening it up.  Chief Quimby stood inside.

“Ah, good morning, chief!  Nice of you to join us for breakfast.”

“Here’s your assignment, Gadget.”

Chief Quimby held out an envelope, which Gadget accepted and opened.  His eyes skimmed the page, mumbling as he read his assignment.  After gathering the information that he needed, he balled up the message.

“No need to worry, chief!  I’ll get to the bottom of this phony at once.  Inspector Gadget always pegs his man!”

The coffee that Wynona had been sipping on choked her the moment she heard that exclamation.  She sputtered and began coughing, causing everyone in the kitchen to look at her.

“Are you okay, Aunt Wynnie?” Penny asked, reaching over to pat her back.  Wynona nodded, covering her face with a napkin.

“Yes, yes.  I’m fine,” she said with a slight cough.  “Went down the wrong pipe.”

She was trying her hardest not to burst into laughter.  The last thing she needed was to have to explain why what Gadget said was so fucking funny to his ten-year-old niece, his boss, and him…  Or maybe just him and his niece, because his boss held his face like he knew exactly what was going through her head.  That reaction only made Wynona crack up, and she quickly rose from her seat.

“E-Excuse me,” she said, before rising from the table and retreating down the hall.   She ducked into the half bath, stifling snickers as she turned on the sink and splashed water on her face.  God, she needed to get herself together and get her mind out of the gutter.  There was a tap on the door soon after.  She walked to the door, cracking it open to see Gadget standing outside.

“You okay in there, Nona?” he asked.  “Just wanted to check on you before I went off.”

“Yes.  Yes, I’m good.”

After confirming that she was okay, Gadget smiled and leaned against the door frame.

“If I didn’t know better, I’d say you seemed a little tickled,” he noted.  The man wasn’t nearly as clueless as people made him out to be… Okay, maybe he was pretty darn close to being that clueless, but he did have those rare moments of perception that must have got him the job.  “Mind telling me what tickled you?”

Wynona frowned.  She didn’t want to be the one to tell him.  She never wanted to embarrass him or make him feel silly.

“I… I can’t, Gadget,” she said with a shake of her head.  “It’s too dirty.  It was completely inappropriate.”

The amused expression faded from his face and he straightened up.  “… Was it something I said?”

She hesitated, then eventually nodded.

“C’mon, Nona.  What was it?” he said.  “If it’s that inappropriate, I don’t want to accidentally say it again.  Especially not in front of Penny.”

In his defense, that was a damn good argument.  Wynona took a breath and ran her hand down her face.  Shit.  She was going to have to fess up.  She motioned him closer.  After he leaned in, she began whispering in his ear.  His face went from pink to red in seconds.

“Wowsers!” he exclaimed.  “Who does that?”

Wynona shrugged.  “I dunno.  Plenty of people.”

“Really?”  His disbelief was evident.  One hand came out of his hat to rub his chin as he pondered this.  “Why?  Wouldn’t that… hurt?”

She waved him back down and whispered another explanation in his ear, which caused him to cover his dropped jaw.  She looked back up at him, trying to gage his reaction to learning about what had to be a taboo topic to him.

“How on earth do you know all that?” he whispered back.

“Don’t forget that I was a bad girl before I met you, Gadget,” she said, donning a smirk before patting his back.  “Good luck on your assignment.”

 

⚙⚙⚙

 

“Have you done it before?”

Wynona looked up from her book, looking over at Gadget as he lay beside her in bed.

“Huh?  Done what?” she asked.

“That… Peg thing.”

The book on Wynona’s lap was shut and sat over on the nightstand.  This was going to be an interesting conversation.  She looked at him a moment, studying his face for a hint of what answer he was expecting.  She’d dated plenty of guys before Gadget, and had experienced a little bit of everything under the sun, at least in comparison to him.  She couldn’t lie to him, but she couldn’t bring herself to answer out loud.  She swallowed and bobbed her head.

“Can we do it?” he point-blank asked.

“Wh-What?”

“You did say it feels pleasurable, right?”

“I mean… Yeah, some guys do enjoy it.”

“Maybe I’m one of those guys!” he confidently said.  “Only one way to find out!”

She certainly admired his gung-ho attitude about it.

“Gadget… I admire how intrepid you’re being, but maybe we should start smaller first?”

“Smaller?” he asked, tilting his head.  “Like how?”

She bit her lip, hating that she was about to suggest this.

“… Like my fingers.”

Gadget grew flustered, sputtering and trying to come up with a proper response.

“You… You don’t find that gross?”

“I mean, yeah.  It kinda is, but you’re clean and my nails are trimmed.  So, like, it shouldn’t be too bad.”

He nodded as he stared with wide-eyes at the foot of the bed.  She held her breath, wondering if perhaps she had pushed him too far out of his comfort zone by suggesting this.  Eventually, he looked over at her with a lopsided smile.  “Ready when you are!”

 

⚙⚙⚙

 

Gadget’s extra hands definitely came in handy during a time like this.  While he clung to the sheets, one covered his mouth as Wynona drew her fingers in and out of his tight ring.  The first finger was a bit of a doozy, but after he got used to it, that second one just doubled his pleasure.  He loved the feeling of her digits slowly sliding in and out of him.  He’d never felt anything like it!  His eyes rolled back as she curled the fingers inside him and pressed against his prostate.  Ragged breathing hitched every time she stroked a sweet spot, making his cock twitch against the strained fabric of his boxers. 

“You’re doing so good, Gadget,” she cooed.  “How do you feel?”

Knowing how dangerous it was to remove his hand to actually answer, he just nodded.  It felt great.  Phenomenal!  He couldn’t wait until he could try that peggy thing that tickled her so.