A Buttplug

You smile as you retrieve the stainless steel buttplug from the drawer. While not comically large, it was big enough to be uncomfortable. At the base was a flat pink gem which would twinkle between her cheeks. Bringing the toy into to view, Lily's eyes went wide with fear.

"No, Sir, please, I'm sorry!" She whimpered, her beautiful body trembling. "I won't complain anymore, I promise!"

"Of course you won't," you slyly respond. "Not after spending the rest of your day with this in!"

"Master, I've... I've never had anything in there..." The blonde blushed, averting her eyes. "I don't even think it'll fit!"

"Then you better lube it up." Holding the thin part between your fingers, you bring the plug to her lips. "It might really hurt otherwise."

Lily met your gaze, her wide eyes making one last silent plea for mercy. While they did not find cruelty in your eyes, she did find her answer. This would be her punishment, and she would have to accept that. Without further hesitation, she slipped the bulb into her mouth.

You held the butt plug for her as she sucked and slurped all over the toy. Drool dripped onto your desk as Lily did her best to cover the plug with spit. Bobbing her head back and forth. Running her tongue over every inch. Everything in her power to make its eventual entry into her ass as easy as possible.

"Alright, that's enough," you say after about thirty seconds, pulling the toy back. It leaves her mouth with an audible pop, a trail of saliva left behind.

Lily looked on with trepidation as you circled around the desk. You could tell she wanted to flinch away, to get her ass away from you. However, she was a good girl who knew she had made a mistake, and so obediently stayed put.

Coming up behind her, you flipped her skirt up, revealing a pair of black lace panties. You used two fingers to rub her crotch, eliciting a shudder from Lily. As you had suspected, they were soaking wet! Chuckling to yourself, and imagining how red her face was at the moment, you tugged at the waistband. The panties dropped down to her ankles, revealing her bare bottom.

"These will stay off for the rest of the day," you informed her, using your free hand to palm her ass. "I may need to check that your plug is still in, after all."

"Yes, Sir," the blonde whimpered, a hint of arousal in her voice. She could not help it. Despite not looking forward to her punishment, her Master's hand was on her ass! The reaction was practically automatic.

Pulling one of her cheeks to the side, you exposed Lily's tight asshole. The hole winked at you, as if it knew what was about to come. Bringing the plug close, you pressed it against the entrance. She winced as the cold metal made contact, at first simply feeling uncomfortable. However, this soon turned to pain as you began to apply pressure.

"Just relax, Lily," you instructed, more as a command than an attempt to soothe her. "It will make this easier."

You could tell she was trying her best, and slowly but surely the hole yielded to you. Still, every millimeter was a battle as her body fought to keep the plug out. If you had any doubts that she was an anal virgin, this dashed them completely!

Then, just when you thought you might need more lube, the rest slipped in all at once. Lily gasped as her ass swallowed the toy, her body practically jumping in the air. Examining her ass, you saw the gemstone twinkling above her asshole. You gave it a few flicks with your thumb, and watched with glee as Lily shuddered.

Curious how she really felt about this, you brought your hand lower and cupped her cunt. Indeed, it was even wetter than before, her arousal soon coating your exploring fingers. Lily bucked and mewled in your grasp, like a bitch in heat. You could feel blood rushing to your penis, and considered taking her right here right now. However, you felt giving her that much pleasure might undercut the punishment aspect of this exercise.

Showing restraint, you just gave her a swat on the ass. "Stand up!" Lilly quickly complied, rising to her feet and turning around. You could see her shift from one foot to another, getting used to the uncomfortable object now shoved inside of her.

"You will make sure this stays in all day," you instruct, the blonde just nodding her head. "Only take it out before you go to sleep. Then, leave it on your night table. A little reminder in case you start questioning your place in this household again."

"Yes, Master," she replied, hanging her head demurely. "Again... I am sorry for complaining. I... I should not have disobeyed you. You know what's best for me..."

You sighed, placing a finger under her chin and tilting her head up. When her eyes again meant yours, they met a more forgiving gaze. You had been hard enough on her, and thought a bit of tenderness might go a long way.

"It's okay, Lily., you are still learning," you assure her. "This punishment is really to help you adjust to your new life. You are still one of my girls, don't worry."

"Thank you, Master," she gushed, smiling sweetly. Leaning down, you gave her a loving peck on the forehead.

"Now get back to work!" You order, giving her another playful swat on the ass. She jumps at the impact, amplified by her new plug, and scurries out of the door.