Only a moment later, Alan's hand was gone, and Aspen was violently brought back to reality. He blinked, only to his at the sensation of Alan sliding the damned cock ring on his penis. It was ... weirdly tight, but not to the point where its presence made Aspen want to run away.
He sucked in a breath and ran a hand through his hair.
"Have you ever used a cock ring before?"
"No, Master."
Alan smiled. "I'm glad I get to be part of so many of your firsts. How does it feel?"
"Not too bad."
"We'll see how you feel in a moment, won't we?" Alan left him standing and went over to the corner of the room, grabbing the chair that he'd sat on to spank Spencer.
He placed it down in front of Aspen and sat, demonstratively folding up the sleeve of his dress shirt.
"Come kneel here," he then said, pointing at a spot next to his legs, "with your back to the door."
Aspen sucked in another breath and then did as Alan had bid him.
"Now, get over my lap."
Aspen awkwardly laid his torso on Alan's lap, and his friend grabbed him by both hips and gently lifted him further so that his ass rested on Alan's legs.
"This is what people call an over-the-knee spanking," he informed Aspen while he rubbed a hand over one of Aspen's exposed cheeks. "I have other positions that I prefer, but for now this will do. You'll receive ten, and I want you to apologize for snapping at your employee after each of them. Do you understand?"
"Yes, Master."
"What's your safeword?"
"Red, Master."
"Good."
The rubbing stopped, Alan's hand disappeared, and then it was back, landing on Aspen's cheek with a crack that made Aspen gasp. He wasn't entirely sure what he had expected. His skin tingled with pain, but after a few seconds, the sensation made way to warmth.
Alan hummed appreciatively and it reminded Aspen that he was supposed to apologize.
"I'm sorry I snapped at my employee."
"Good boy."
Crack.
And with that, Aspen and Alan traded apologies for spanks.
It was over before Aspen had even really realized it.
"You took it well," Alan praised him. "And your ass is a lovely pink now."
Hands found their way to Aspen's hips and he was lifted off Alan's lap and placed on his knees on the floor.
"Not to mention the toy did what it was supposed to."
That comment made Aspen look down, and indeed, he had a hard-on. He felt heat rise to his face like it had to his ass, but he just sat there, on the floor, in silence, and waited.
"I already told you you wouldn't get to cum today, and I intend to keep it like that."
He curled a finger at Aspen and Aspen took that as a sign to get up.
"Usually," Alan added with a smile, "This would be where you have an orgasm and I take this toy off, but I can manage since you're not awfully hard."
Somehow, Alan managed to roll the silicone ring down Aspen's penis like a condom, and then Aspen was free of the slight discomfort that it had brought him.
"A good submissive says thank you for the punishment when it's done."
"Thank you for the punishment, Master?"
"And what did you learn today?"
"I learned that it's very rude to snap at your employees."
"Good. Turn around."
Aspen heard the cap of a bottle pop and then the cooling sensation of some sort of ointment on his red cheeks."
"We're done here," Alan announced. "Off to bed you go. And don't even think about touching yourself."
Aspen wanted to say something, but he turned his head only to be met with Alan's strict gaze as it settled on him.
So he thought twice about it before he nodded. "Goodnight, Master."
"Goodnight, Aspen. Sleep well."
Aspen almost fled from the room at that and then locked himself in the bathroom, twisting and turning in front of the mirror to try and catch a glance at his ass. His ass flashed pink in the mirror and he gasped at the sight.
He hadn't expected it to hurt, and he flinched when he reached out and dragged his fingertips over the agitated areas, hissing through his teeth. Damn.
Alan really wasn't playing games.
There was a knock on the door, and - as Aspen almost expected, it was followed by Alan's harsh voice. "If you are touching yourself-!" he warned, prompting Aspen to unlock the door immediately.
"I wasn't-" he started, but Alan cut him off.
"I can see that. I thought I told you to go to bed."
"You did. I just- I guess I wanted to see."
"And now you're embarrassed."
Aspen couldn't bring himself to admit it, so he just bobbed his head. And then, all of a sudden it dawned on him - he was still naked.
"If you ask nicely tomorrow morning, I might humor you," Alan said - almost as if he had read Aspen's mind - winked, and pushed past Aspen into the bathroom.
Aspen huffed as the door shut in his face and then dashed across the hallway into the guest bedroom. He fished a pair of boxers from the closet and slipped it on, hissing as the rough fabric rubbed over his ass.
He climbed into bed, trying his hardest to get comfortable, his mind slipping into an endless string of confusing thoughts about Alan, their relationship - whatever you might call it - and the spanking.
It wasn't as bad as he thought it would be, but he knew that was because he was new to this, and Alan was practiced in decency. But still, he wasn't exactly sure if he wanted to experience something like that again.
It had hurt, and now that he had seen the aftermath of it, he was ashamed - and embarrassed, as Alan had pointed out.
He felt like he had gotten himself into a whole mess.
YOU ARE READING
COMPLETED | Take Me Down The Rabbit Hole (BDSM | 18+)
RomancePrequel to Take Me To Wonderland | Can Be Read As A Standalone COMPLETED ➜ 08/10/2025 ____ "I don't know." "I could teach you," Alan said, a grin forming on his face. "And you know I'll pay well." Aspen laughed. "Are you trying to bribe me?" __...
