Spanking from Santa

After months of scrolling through Grindr, I thought nothing could surprise me. However, I was proven wrong one cold, December night. It was my first winter in grad school and I was stuck on campus doing research over Christmas. Around midnight, I was trying to come up with a thesis statement when I heard the tell tell ping on my phone. I opened the app, expecting another mediocre dick pic. Imagine my surprise when I was greeted with Santa. No, not an avatar. But a hot ginger man with twinkling emerald eyes dressed up in a bright red suit with white trim, the classic Santa hat, and tall black boots with a bag marked "XXX" slung over his shoulder that bulged with what suspiciously looked like dildos.

"Have you been naughty or nice this year?"

Intrigued, I immediately wrote back. "Santa, I've been such a naughty boy. I was performing as a drag king all weekend when I should have been studying for finals. Am I going to get coal in my stocking?"

"This year, Santa is doing something a little different. Bad boys can earn their place on the nice list, but it's going to hurt. How badly do you want to be good?"

"What would I have to do to become a good boy?"

"Let Santa spank your ass as red as mistle toe and maybe you'll like what you see under the tree this year."

I'd never been spanked before but I fantasized about it for years. I needed a release from writing all day and the stress of finals week. We exchanged a flurry of messages about boundaries, STD status, safe words, and what I wanted Santa to call my anatomy since I'm a trans man. Then I sent Santa my address.

I answered the door in a velvet Christmas apron open to the back, an elf hat, and a smile. Santa was tall, at least a foot taller than me (I'm a short king at 5 foot even), and cuter than his picture. He was broad and built with a football player with a sexy beer gut. He stepped inside, put down his large sack, and let loose a loud guffaw. "You have been a naughty boy, you dirty slut. Why you're baring your bubble butt for the first man you meet. You know what that means, don't you?"

"That I get a hard spanking?" My voice slightly hitched at the end of the sentence. Suddenly, my fantasy was becoming real and I didn't know if I could handle it.

"That's right. But if you take this like a good little boy, I'll move your name to the nice list." He grabbed a chair from the dining table and put it in the center of the room. Slowly, I walked towards him, my stomach fluttering. He sat down, grabbed my hand, and pulled me across his lap. Suddenly, all I could see was his red velvet pants and his snow covered black boots. The apron offered no protection for my ass and my front hole. I felt embarrassed and small but also was incredibly turned on. All the control I had to maintain in my daily life, to say the right thing in class, to publish a paper in a respected journal, to command the audience as a drag king on the weekends, was gone. I was Santa's plaything and that's just the way I wanted it.

"Now, do you remember our safe word?"

"Rudolf."

"Good. Now, I'm going to spank your ass with my bare hands, then my gloves, then whatever I see fit until you cry like the naughty boy you are. You can wriggle and moan but unless you say 'Rudolf,' I won't stop. Is that understood?"

"Yes."

With a whoosh, a hand landed on my ass and I slightly yelped. "Yes, what?"

"Yes, Santa!"

"Good boy. Now, I want you to thank me after each stroke."

The spanks started off slow and he alternated cheeks, rubbing my bottom between each. I was thinking this wasn't so bad when the next one jolted me forward, almost making me lose my balance. "Ow! That hurt!"

"It's a punishment. It's supposed to hurt. You were a naughty boy and need to take your medicine." He spanked the sit spot where my right ass cheek connects with my thighs three times in quick succession then did the same to my left. After a few repetitions, I felt thick, coarse fabric grab my ass hard.

"You know what this is?"

I gulped. "You're wearing your gloves?"

"That's right. Right now, your ass is tinged with a delicious blush but soon it's going to be as red as my hat. Don't forget to thank Santa or it won't just be my gloves you feel."

I barely had time to steady myself before I felt the full impact of his hand on my left cheek. I squeaked out, "Thank you, Santa." But I wasn't loud enough. His hand landed in the same spot and I jerked forward, my elf hat falling off my head.

"I can't hear you!"

"Thank you, Santa!" I felt embarrassed at how eager my voice sounded, at the yearning for more.

"Good little elf." His chuckle was positively mischievous. He spanked each cheek fifteen more times and I made sure I was loud enough. Tears started to drip from my eyes and it became harder to thank him. After five more on each, I was openly crying and whimpering. Just when I was about to say our safe word, I heard him strip off the gloves. Then I felt his calloused hands graze my front hole.

"Dirty boy. You're so wet. Spread your legs for me, you little slut." I quickly did what his told, my T dick throbbing. He massaged my T dick with his thumb and it grew hard under his ministrations. He teased my front hole, tracing his fingers along my lips as I wriggled my hips. I felt one finger plunge in, then two. He pulled them in and out slowly, making me lightheaded. Next, I heard him rustle into his bag and the sound of a vibrator turning on. He held his hands down for me to see. Santa was wielding a vibrating candy cane dildo in one hand and a thick wooden spoon in the other. I gulped.

"You've earned some pain with your pleasure. I'm going to fuck your tight little front hole with this candy cane as I spank you with Mrs. Claus' spoon until you come. What do you have to say about that?"

"I deserve to be spanked for being such a little slut."

At the same time as the vibrator plunged into me, the spoon landed on my ass. I didn't know if I was moaning in pain, pleasure, or both. Soon, all I could think about was the throbbing of my T dick, of the stinging of my ass, of my need to have that candy cane as far in me as it would go. If you asked me what my name is, I'm not sure I could have answered. All I knew was this desperate need to be filled, to be punished, to come. I wasn't sure if it had been thirty seconds or thirty minutes, but my front hole started spasming around the stripes of the candy cane as the orgasm rushed over me. I felt Santa's thumb rapidly stroke my T dick as the spoon landed at a furious speed.

"Yes, Santa! Yes!" After ten more good, hard spanks with the spoon timed perfectly with deep thrusts of the candy cane into my front hole, I fell limp across Santa's lap.

Slowly, he pulled the vibrator out and gently rubbed peppermint scented lotion all over my stinging ass. Then he pulled me up onto his lap and cradled me as I came down from the orgasm. "You took that spanking so well and earned your name on the nice list." After a few more minutes of sitting on his lap, Santa left peck on my cheek and helped me stand.

He picked up his sack and crossed the room to the door. Just before he walked out, he turned and said with a wink, "Don't forget to leave out cookies on Christmas Eve if you want Santa to come back with a present for his good boy."