Day 26 - Pegging


“This place must be popular with inspectors,” Gadget whispered to Wynona as she studying the wall of merchandise in front of her.  Her brows furrowed at this remark, and she looked around to understand what she was talking about.  Her hand clapped over her mouth when she noticed that the majority of patrons inside the establishment were also donning trench coats and hats.  “Funny.  I’ve never heard of it before.”

Wynona shook her head, touching Gadget by the arm to draw his attention onto her.  “Never mind them.  Let’s just say everyone’s on a bit of a personal mission,” she said.  “Now, focus.  I need you to pick out one of these.  Which one do you like?”

She gestured at the toys of various shapes, sizes, and materials.  He hummed and rubbed his chin as he looked them over again.  After a while, he scratched the back of his head and shrugged.

“Gee, I don’t know, Wynona,” he said.  “Is there just a plain one?  I don’t think we need a fancy gadget to get the job done.”

She nodded before leaning down and grabbing a box off the bottom shelf to pass to him.  It was a simple, no frills silicone dildo.

“What about that one?” she asked.  “It’s not too big, has no special features.  I think it’s a decent one for a beginner.”

A light pink blush spread across Gadget’s face when he looked down at the box in his hands.  He quickly passed it back to her to pop the collar of his coat.

“… Not in here, Nona,” he leaned in to whisper to her.  He quickly glanced around before continuing.  “What if these are my colleagues?”

She forced a straight face, not having the heart to tell him that these men were in no way police inspectors.  She just tossed it in the basket with the leather harness and bottle of lube she’d already picked out.

“Anything else you want to look at while we’re in here?” she asked.

Gadget did a quick scan of the store before bashfully casting his eyes to the ground and shaking his head again.  With that confirmation, she took her basket and walked to the counter in the middle of the shop. A bored-looking cashier typed the prices of each item into the cash register before stating the total price.  Wynona looked over at Gadget, who fished his wallet out and passed some cash her way, which she used to pay for the goods.  The change was given back, along with a discreet black bag.  After thanking the cashier, the two of them made their way out of the shop. 

They had to walk a block over to where the Gadget-mobile had been parked.  He was awfully quiet the entire time, causing Wynona to reach over to rub his back.

“You okay?” she asked, and he nodded.  “You know, if you don’t want to do this, we don’t have to…”

“No, no,” he said, shaking his head.  “Inspector Gadget doesn’t let a little bit of nerves get in the way!”

Wynona chuckled at this as he extended his hand to reach for the handle of the passenger door to open it before she reached it.  After she got in and he shut the door for her, he stepped around to his side of the car and climbed in.

“Okay, well,” she started.  “Just know you can call it off at any point if you’re not feeling it.”

He nodded in acknowledgement as he started up the car.

 

⚙⚙⚙

 

While the toy looked like a mere plaything in the store, it was rather imposing when strapped to Wynona’s hips like that.  Gadget had gotten used to a few fingers inside of him, and now that Penny was off at a weekend computer camp, he could finally experience that peg thing that Wynona had mentioned weeks ago.  Even as on edge as he was, he was getting painfully erect at the scene that was beginning to unfold, particularly the sight of Wynona stroking lube up and down the shaft of the toy.

“Drop the pants, Gadget,” she said.

“Y-Yes, ma’am!”

He rose to his feet and began fumbling with his belt buckle.  The knowledge of her eyes trained on him made it suddenly the most impossible task in the world.  He eventually managed to get his belt undone, then his fly.  His pants dropped to his ankles and he stood there before her in his button up and boxers.  He stepped to the side, kicking the pants off his feet, and awaited his next task.

“Turn around and get on the bed,” she said.

He spun around and scrambled up on top of the mattress, assuming a position on all fours.  He glanced back over his shoulder at her for validation.  She walked up behind him.  The mattress dipped when she joined him and stood on her knees.  The cool air of the bedroom was soon felt on his bottom as she pulled the boxers down.

“Last call,” she said.  That strap of hers brushed the inside of his bare thigh.  Any doubts or reservations he may have had about this escaped him upon feeling that.  He gulped and shook his head.  “Okay.  Here goes… Lean forward a little.”

He did as she instructed, leaning forward to give her better access.  The lubed-up silicone slipped between his cheeks, sending a shudder through his body.  It brushed past his hole a few times, making him bite his lip in anticipation.  Then, her hands gripped his hips and adjusted her position.  He sucked in a breath when he felt the tip of the toy against the ring of muscle.  It pressed in, stretching him as it inched inside.  He gasped and tensed.  This was definitely thicker than those fingers of hers. 

Wynona noticed his posture and stopped going any further.  Her thumbs stroked his hips.  “How we feeling?”

The breath that Gadget hadn’t realized he had been holding escaped him, and he inhaled deeply before mustering an answer.

“L-Like I’m getting split wide open,” he stammered.  A soft laugh left him and he shook his head.  “… And loving it.”