Please, Santa, I Want More #Halloween #erotica #FreeStory #spanking


Hope you’ve been enjoying the free stories I’ve been offering up all day. For this final M/M story, I thought I’d focus on that huge holiday coming up -you know the one. It’s run by a large, rotund elf who says “Ho ho ho.” Xander thinks this will be just another fun night of serving a woman. He didn’t expect Santa.

Thanks for reading. Please don’t copy/paste elsewhere.

*****

Please, Santa, I Want More

Closing the door tightly behind him, Alexander dumped his book bag on his desk chair and collapsed onto his bed. “Damn, but I’ll be glad when college is over,” he groaned. Every year just seemed to get harder. Classes this fall term had been brutal. Part of it was that he doubled the number of credits he normally took, but also, all were high-level classes and assumed they were the only one he had, so over the last four months he wrote twenty-five papers, took twelve exams, did six group projects, and gave three oral reports.

“College sucks.”

Graduation was looming in less than six months and he could hardly wait. Fall term classes were over, the only thing looming ahead was finals and thankfully, six of his eight classes had required papers for their final. So, he only had two exams to take. And those wouldn’t start for a week.

A buzz from his pocket made him jump slightly and he lifted up his hip so he could get his phone out. It contained a single message.

Tonight. 8pm. Karrington – 1459. 3-piece suit.

Shivering, his face turned up into the first smile in three weeks. When he first came to college, he worked odd jobs—as a barista, a retail clerk, and even as a UPS man for a semester before he caught a break. He was working the front desk of the Karrington Hotel when he was first contacted. As he came back from break there was an envelope on the desk with his name on it.

It was from an escort service. It was the end of his sophomore year in college and he was tired of having to dig into the corners of the crappy sofa in the dorm looking for loose change just so that he could go out and have fun. His parents could afford to help him, but as his dad told him all the time growing up, “Hard work never hurt anyone.”

True, but, it certainly made it hard to study and enjoy himself. The idea of being an escort had at first been embarrassing. But over the next few days as he caught a glance of himself in a mirror or in the reflection of a glass door, he began to wonder if being an escort might work. It took three months of covert meetings, physical exams, and several tests before he got his first assignment; to accompany a seventy-year old woman to her class reunion, acting like her boy toy. After four hours of being pinched, rubbed, and kissed, she gave him a two-hundred dollar tip, and that was on top of what the escort service paid him.

He loved his job. In the last year and a half, he was called up almost every Friday and Saturday night by older women who wanted a young man to make them feel wanted again. The money was fantastic and the sex? Out of this world. Some of these women were simply freaks and he enjoyed every minute of it. Well, except for the weird one who wanted to put his cock in a cage. That was the night he found he actually had a boundary he would not cross. She was disappointed, but he went down on her for over two hours and by the time he left, she gave him a three hundred dollar tip.

“The 007 of the escort world,” he said cockily as he stood up. Tonight’s rendezvous excited him. He had only been called to the Karrington Hotel three times and each time had made him so much money that he would have been able to take months off of work… if he hadn’t enjoyed his job so much. The only part of the job that was annoying was the monthly physical, but he took it in stride. Heaven knows he didn’t want any diseases and condoms did not necessarily block everything.

Grabbing his notebook, he jotted down the basics in a code only he knew and then rushed to the shower to start getting ready. Over his eighteen months with Pony Express, he had been with one hundred and forty-two women and each one of them had taught him something new. He could hardly wait to see what this evening’s lady would ask him for.

***

At 7:45 p.m., he sauntered into the Karrington in his best 3-piece suit, an Armani he purchased after one banner month with the company. He kept it in the back of his closet, only using it for these occasions. His expensive suit, ultra-shined shoes, and good looks made everyone assume he belonged there and nobody batted an eyelid as he pressed the button for the elevator and stepped inside. The fourteenth floor was the penthouse level and he could practically feel the extra money that would soon make it to his offshore account.

At 7:57, he stood outside suite 1459 and knocked. One minute passed and a second minute. He was used to this. Some of these women made him wait until they were ready to open the door. He was paid to be the perfect escort and the perfect escort he would be. The sound of a latch coming undone occurred at exactly 8:00 and he pasted on his most charming smile as the door swung open.

Standing in the doorway was a man slightly taller than his 6’ stature with raven hair that was going silver at the temples and brown eyes. He wore suit pants and a white dress shirt with the sleeves rolled up. The man’s deep brown eyes wandered down Alexander’s suit and back up before he nodded. “Xander?” he asked in a deep voice.

Surprised at a male answering the door, but quickly masking it, Alexander nodded. The service had suggested he use a different name than his own. He had tried several at first, and while Xander was technically a part of his own name, every client he’d had said it had sounded so good they had to ask for him. So, it had become his escort name for the last fifteen months.

“Come on in.” The man stood back and Xander walked inside. When he’d worked at the Karrington, he caught a look at the fourteenth floor suites once, but only from the doorway. Now he would get to see how they really looked. He walked in to a small foyer. “Go and stand in front of the balcony.”

He was used to being told what to do and slowly moved through the inset living room with large leather chairs and a long leather couch, only stopping when he stood in front of the open balcony doors. Figuring this man had purchased him for his wife or his mistress, he stood and waited. That had happened twice before. Rich men who wanted to watch another man fuck their girl. He loved it, but it still felt weird.

A strong presence stepped behind him and he tensed as two strong hands landed on his upper arms. “For tonight, you can call me Santa,” the man said in a husky voice.

“Okay, Santa.” Internally, Xander chuckled. The other rich men who had purchased him for the night to fuck their women thought they were giving him a gift too. This one had obviously decided to take on the role of the ultimate gift-giver—well whatever floated his boat. Ho ho ho. Where was the scantily-clad woman who needed him? He briefly wondered if she would be dressed as an elf.

Santa reached around and unbuttoned his suit coat. “Let me remove this for you,” he said. “The last thing we want is to wrinkle an Armani suit. Do we, Xander?”

A slow shiver went through him at the sound of his name. It sounded like a caress and he was confused at how he felt about that. “No, Santa.” He shrugged out of his coat and turned to watch the man walk over to a closet and hang it up.

“In fact, I would hate to see anything happen to those pants or that shirt. Strip.” The command in the voice surprised him and he stared open-mouthed at the tall, nicely built man who raised an eyebrow when he did not respond to his command. “Do I need to cut them off instead?”

Blushing at the rebuke, Xander reminded himself this was part of the game and quickly removed his shoes, pants and shirt, leaving him in bright red boxer shorts. It felt festive when he put them on. Now they seemed in keeping with this man’s Santa-esque persona. As he moved to walk the clothes over to Santa, the man held up his hand. “Halt.” He froze. “Stay in front of the balcony, Xander.” Santa quickly put his clothes in the closet and then walked back toward him. When he got to the living room, he sat in a large brown leather chair and stared.

Trying not to fidget, Xander kept his face as impassive as was possible and glanced toward the door to what he assumed was the bedroom. What was Santa waiting for? Xander had stood nude in front of tons of women in this line of work, but he had never felt so naked before. Santa’s brown eyes missed nothing—the convulsive swallowing, the way his fingers tapped against his hip as he dug his toes into the soft carpet. “I was under the assumption you’d been doing this awhile,” he said quietly. And yet, through that quietness came a strength that made Xander’s heart take off.

“I have, Sir… uh, Santa. Eighteen months now.”

“You seem awful edgy for someone with that much experience. Do I make you nervous?”

Frowning, Xander deliberately looked at the bedroom door, wanting this man to bring out his girl. Let’s get on with it, he thought ruefully. Neither of the other men had made him this nervous and he wasn’t sure why. “I’m used to being looked at by women, Santa.”

Chuckling, Santa shook his head. “Come now. You’re a gorgeous, fashion-conscious male. I’m sure many a man has undressed you with his eyes. I just happen to be able to do it without others watching. Remove your boxers.”

His eyes widening, he once again glanced at the closed door.

“Don’t worry, Xander, we’ll get there. I ordered you for the whole night. No reason to rush things. The sleigh will wait.”

The sleigh? Must be a sleigh bed. Even as the thought crossed his mind, he realized what Santa was saying. Frozen, Xander stared at him. He ordered him? He wanted him? But he had never served men. Ever. Sure on his form he said he would work with them, but he had never been called to before. He cleared his throat nervously. “I think there has been a mistake.” He tried to sound as firm as Santa, but his quivery voice gave him away.

Santa smiled, stood up, and walked toward him, looking like a fucking cat coming in to play with a mouse. Reaching out his hand he cupped Xander’s cheek and rubbed it with his thumb. A gasp left Xander’s lips as his cock chose that moment to make an appearance. Santa’s eyes fell to the bulge and a smirk covered his face. “Definitely no mistake, Xander. You want to experience this as much as I do. Take the boxers off. Now.” The last word was spoken clearly, firmly, brooking no argument.

Xander’s hands shook as he pulled his boxers down to his ankles and kicked them away. Why was he turned on by this man? It made no sense. He liked women, big-busted, hippy women! This man was the exact opposite. Firm, and tall, and he smelled amazing. Wait. What?

“That’s better,” Santa said. “Let’s see if you have been a good boy this year, shall we?” He turned and strode back to his chair and then crooked a finger at Xander. “Come.”

Taking a deep breath, he walked toward Santa, ever aware of his cock bouncing to and fro with each step he took. “Children sit on Santa’s lap, but you are not a child, Xander. As such, you can bend over my lap.”

Spanking. The man was going to spank him. He almost giggled. One of the women he had served had been into spanking and had asked him to spank her. He complied, but could not understand what she saw in it. Spanking hurt, didn’t it?

“Now, Xander.”

The commanding voice made his forehead break out in a sweat and a weird sort of nervous reaction take place in his abdomen. He bent stiffly over Santa’s lap. With a grunt, Santa shifted him so that his ass pointed up in the air and his head almost touched the floor. His breath caught as a hand began to knead his buttocks. “You have a fine ass, Xander. I’m going to enjoy painting it red. Then you’ll wear a special outfit I have planned.”

As he considered his position, Xander figured letting Santa spank him wasn’t such a bad thing. He could handle it, get his money and go. Taking a deep breath, he relaxed.

SWAT!

As fire spread across his left ass cheek, Xander gasped.

“Feels good, doesn’t it?” Santa mused. “Spread your legs.”

Frowning at the request, Xander didn’t move right away. SWAT! “Fuck!” he gasped, moving his legs apart.

“That’s better,” Santa said in a smooth voice. A hand reached between Xander’s legs and he moaned as a digit caressed the sensitive area between his balls and his ass. “Very nice.”

Two more smacks came in quick succession.

Gritting his teeth, Xander tried not to yell out. Each swat hurt worse than the one before it and fire was chasing across his ass at an alarming rate. Five swats later, he was panting at the pain, but refusing to call it quits.

Once again, Santa’s hand drifted between his legs and Xander let out a long moan as a hand stroked his cock. “You are a very good boy, Xander,” he crooned softly. “And your ass is a nice soft pink. We have a ways to go before it is red. In the meantime…” Whap! Whap! Whap!

A cry left his lips as the pain seemed worse than before. Almost immediately that hand was stroking him again and the pleasure began to mix with the pain. What the fuck?

Santa’s hand came down hard and fast, taking the burn up to a flame.

“Please, please, please,” he moaned, though what he was begging for, he wasn’t sure. The spanking was painful, but it was also pleasurable. What kind of kinky Santa was this? Xander was not a masochist. No siree!

“Good boy,” Santa crooned, stroking one finger around Xander’s asshole. “Have you ever had anyone in here, Xander?”

“No,” he grunted, fidgeting at the strange sensations that were shooting through him. A finger on his asshole should not feel good. But it did. It really did.

“If you are a good boy, you will tonight.”

Before he could react to that line, Santa spanked him again. Harder. His palm slammed against Xander’s ass cheeks, both hurting and exciting him further.

“Please!” he moaned. “Please, Santa!”

“Please what, boy?” Santa asked in a very Santa-ish voice. “Please stop? Or please give you more?”

Xander opened his mouth to say “please stop” but the words would not come out. He tried again. And again. But to no avail. He couldn’t lie lying upside down on Santa’s lap. “More,” he moaned. “Please, Santa, I want more.”

“Ahh, good boy.” Santa chuckled. “We are going to have a great night tonight.” Santa began to swat him firmly on his ass and thighs, interspersing it with stroking his cock and before long Xander shuddered with need he had never felt before. He seemed to have passed the ability to beg. His mind was muddled, searching out the next swat or stroke to feed his desire.

Something wet spread over his anus, making him squeak.

“Hold on, my boy. You are going to cum harder than you could ever imagine.” Santa began to reign hard slaps onto Xander’s ass cheeks at the same time one of his fingers began to move the wetness around his asshole.

“Ohhhhhhh!” Xander moaned as each swat took him higher, made his body tense more than he could imagine, and yet he wasn’t getting close enough. Please! he begged in his head. Please, help me come!

Even as the thought bounced around in his head, something entered his ass. As a loud cry left his lips, Santa pushed his middle finger all the way in, increasing the intensity of the slaps. Xander wanted to beg him to stop, to let him come, to hit him harder. All the thoughts were converging into one and he started to let out a strange sort of keening noise. As something even bigger entered his ass, he cried out.

“Shh, Xander. It is just two fingers.”

Before Xander could even try to think of a reply, hell before he could even think at all, something rubbed up against something that felt really fucking good. “Ahh!” he hollered, arching his back.

“There we go,” Santa murmured. His swats came quickly without a breath separating them, but at the same time, his fingers continually rubbed against that spot.

It was all too much. Pleasure, pain, need, desire, tension, excitement… all of it converging on Xander in one long rush. As his keen went up and he started to practically screech, his body burst into an orgasm. His balls felt like they exploded while his cock continued to spray the floor below him. Muscles from the top of his head to his tiny toe convulsed and shuddered for minutes, unable to stop.

When the overwhelming sensations began to slow down and make some sense, Xander realized he was whimpering and that Santa was rubbing his back in slow circles. “Are you all right, Xander?” he asked quietly.

A huff of laughter escaped his lips. “All right? That is a unique way to put it. I’ve never felt anything that…” He couldn’t come up with the right word for everything he had just gone through. Amazing? Wonderful? Orgasmic? Painful? Life-changing? They all fit. And somehow, being bent over this man’s lap had been a bit of a turn on as well. “I don’t think there is a word that fits,” he finally admitted, making Santa laugh.

“Ah, Xander. You have never submitted to a man before have you?”

“Uh, no, I haven’t.”

Patting Xander’s ass which made him hiss in discomfort, Santa said, “Up you go.”

Grimacing, he stood up, turning around and staring at his bright red ass. “Whoa.” Slowly he turned back until he met Santa’s eyes.

They crinkled with good humor. “The rest of the evening is up to you, Xander. You will get paid for the whole night whether or not you stay as you have been so accommodating. But if you would like to stay? You will experience many more painful pleasures. And some that are just plain pleasurable. What do you say?” he asked as he pulled out a wallet and tossed ten one-hundred dollar bills on the coffee table. “That is yours. You can take it now if you wish.”

Xander’s eyes fell on the amazing tip and he slowly licked his lips. Leave? But… He needed time to think. “What felt so amazing?” he asked to give himself time to consider his quandary.

“That, my dear Xander is a spot far too many men do not know about. Your pleasure spot. Felt good, didn’t it?” Xander nodded eagerly. “Just think of how it will feel to have a cock rubbing up against it over and over.”

A shudder went down his body, but he nodded. Once again his eyes fell on the money. “This is mine if I stay too?” he asked.

Santa laughed. “Of course. That money is yours.”

Grinning for the first time since he entered the suite, Xander nodded. What the hell. He had learned a lot about sexuality from the women he had been with. Looked like Santa could teach him so much more. “I’ll stay.”

“Marvelous.” Rubbing his hands together, Santa stood up and walked out of the room, returning five minutes later with a brown costume. “Put this on.”

Xander grabbed the costume and unfolded it. It took all of five seconds for the realization of what it was. A PVC reindeer costume that consisted of skin-tight shorts with the ass cut out and a hole for his cock, a set of antlers, a black nose with a band to keep it on and a tail attached to a butt plug.

“Hurry up, Xander,” Santa said with amusement. “The rest of the reindeer will be here soon and it would not do for you to be naked.”

Chuckling at the bizarre nature of the whole evening, Xander got dressed. The PVC shorts took forever to get on, but the antlers and nose were easy. Then there came the tail.

“Bend over my lap,” Santa encouraged, sitting down on the leather chair again. “Let’s get that tail inserted.”

Moaning, Xander did so, half of him afraid Santa would swat him again, the other half hoping he would. Surprisingly, the plug went in easier than he thought, but then again, it wasn’t much larger than two fingers. Before he could stand up, the door to the suite opened and the sound of male voices rang through the room. Looking over his shoulder, he snorted as seven men dressed in the same costume he was wearing, two dressed as elves, and one in a tight white teddy stood observing him.

“Is the sleigh ready?” one of the elves asked.

Sleigh?

Santa popped him on his ass. “Up, Xander.” Quickly, he stood up. “Into the bedroom where the sleigh awaits!” All of the others ran for the room and he cautiously followed. With a chuckle, Santa tugged lightly on his tail, making him moan. “The pleasure has just begun, dear Xander. Just you wait.”

Through the door to the bedroom, Xander momentarily froze. Instead of bedroom furniture, there was a huge red sleigh sitting in the middle of the room and all the reindeer were standing in front of it in what looked like a harness. There was one empty spot in the front of the line. “Take the spot next to Vasher, Xander.”

Feeling like he was in some amazing, weird, and kinky dream that he did not want to wake from, he walked over and was strapped in to a harness by one of the eleves. This night was getting weirder and weirder.

And he could hardly wait to see what came next.

*****

Don’t disappear yet. There are two more stories coming up. One is an m/f spanking story and the other? Well, let’s just say it will make you think… and perhaps actually look forward to election day. Or wish election day was like this *grins*