Sleepless Hollow

by mrmidnight

Rating: mature
Tags: Sweetie Belle, Original Character, Porn, Button Mash, Adventure, Rumble, Sex, Anthro, My Little Pony: Friendship is Magic, Alternate Universe
Length: 9270

Rumble Crane finding himself crushing over Sweetie Belle is in big trouble when he runs into Button mash and the mysterious Headless Horsewoman.

Rumble Crane finding himself crushing over Sweetie Belle who's considered one of the prettiest girls in school but only finding himself the target of Button mash, who will stop at nothing to keep him away from his girl. Rumble only finding himself safe in the woods where he finds himself meeting a mysterious headless horseman, but what if there is something more about this headless being.

Contains Monster girl sex, Headless woman, Big tits, Giving head (Pun intended) and more

Published 2020-01-10 14:00:01 UTC
Last updated 2020-02-14 15:37:27 UTC

Part one

In the small town of Sleepy Hollow. Many things had happened in this small town. Most people know the stories. The place is haunted by ghouls and Goblins. Spirits long since passed, and horrors like those that never die. The most excellent story from this town was that of the Legend of Sleepy Hollow.

For those who don't know this classic Equestrian short story, it's about a man named Ichabod Crane, the School Master who'd tried to steal the heart of the lady named Rarity Belle. Before, he had mysteriously vanished without a trace. Some said he was chased out of town by the mysterious Strong Bone. Others claimed that he was murdered. Some of those souls believed he had an encounter with the mysterious Headless Horseman. The Horseman the creature of legend that most men feared. The dark specter that is still thought to be haunting the land, riding in its black steed.

Though how about we go to where our story begins, and that would be the beginning. That seems like the most appropriate place to start after all. So that's how we’ll do it. Our story begins in the town of Sleepy Hollow, at the local high school's Library. Where a young man was slowly placing books on the shelves. A man by the name of Rumble Crane.

At first sight, Rumble Crane isn’t much to look at. He wasn’t a remarkable looking guy. Though he was tall, that's for sure standing close to six feet tall, and basically looked skin and bones. Not the most impressive looking fella, in fact, Most people would have mistaken him as a skeleton. Who wouldn’t, no the most exciting thing about Rumble was his last name. His last name had brought on an ideal legend that he might’ve been the direct descendant of Ichabod Crane. A birth that happened from a one-night stand, with some local farmer's daughter. That happened sometime before his mysterious disappearance. Rumble didn’t know if this was true, though he liked the idea of that.

“I’m the descendant of the man who was killed by the Headless Horseman!” He laughed about as a child. He still remembered that proclamation of that fact. The truth was he didn’t know if that was true, though. He’d asked his father once when he was a child. But his old man had looked at Rumble at his young age and said to him.

“Don’t be silly, it’s just an old story. There’s no such thing as a Headless Horseman. We’ve just got a silly name.” But that made Rumble wonder. He tried not asking his father questions. It seemed as though they never gave him many answers. So the young man would do the only thing he could do. That had been, this had given him is a fascination- no his obsession with history.

That had been his spark, that caused him to find his love of books also. Now Rumble didn’t have that many friends so most of his time when he was at lunch or just had a free class. He’d spend most of his time in the library. It had gotten to the point that the Librarian, Miss Jones. basically offered him a job, at least forced him to put some of the books away since he basically lived in the place. Rumble didn’t mind why not it never killed him.

Today had been a particularly long day, as he pushed the small cart lined with different books, while he placed them over in their respective places. The sounds of the books brushing against each other seemed to remind him of the sounds of the wind blowing on a cold autumn morning. Rumble kept his eyes on the shelf when he suddenly felt the cart push into him. It caught his attention as he looked down. That’s when he saw her.

She was beautiful, and one look at her almost caused Rumble to drop the book he was holding. Sure it bumbled and bounced for a second but he got a hold of it just in time. The woman's name is Sweetie Belle Bone, though you could call her Sweetie most people do. She was a beautiful woman with short light purple hair that wrapped around her horn, a soft smile with a bit of baby fat on her face, but she definitely looked pretty, and her voice seemed like an angel.

Sweetie Belle was standing there as she reached over grabbing ahold of the cart, some who managed to not knock Rumble over. He looked over at her with a simple smile,

“Thanks, Sweetie almost landed on my butt.” He exclaimed, giving a small laugh while rubbing the back of his head. It wasn’t right. He knew he wouldn’t fall but he figured it would give her a little smile. As he tried filling the awkward silence. They would look over at each other for a second or two. Then Rumble decided to ask her.

“Is there anything you need help with?” Moving over, raising his hand over to the book pile. There Sweetie who suddenly felt herself being pulled back into reality, looked over some as she realized what was going on.

“Oh yeah, I need a find a specific book.” She smiled slightly, as Rumble moved away from the cart.

“I’m sure I can help you, though what book?” Sweetie seemed to stop and trying to remember what book she might’ve been looking for as she came to a conclusion.

“Yeah, I need a book by Twilight Velvet.” Rumble smile grew wide, upon hearing that name Twilight Velvet was probably one of his favorite fictional author, who had a habit of taking classic monsters modernizing them with a rather exciting twist’s. Rumble knew just where to look. So he gave Sweetie the biggest smile.

“I think I can help you with that. Come on, I knew exactly where they are.” He moved her over and they walked off towards the fiction section. Rumble had to take a second remembering where William's work was driving around looking through the different books. Examining each book, looking over some, he saw a bit of Horror King, Night Storm, Lewis Carrot. Ahh there she was Twilight Velvet, his books were placed in a neat row and in perfect order for each book in his Monster series.

“There you go Sweetie, one section of books with Twilight Velvet.” Rumble would give a little minute as he watched her for a second. Sweetie looked back at Rumble giving him a smile.

“Thank you so much, Rumble, I appreciate it.” Rumble watched her going over and picking out one of the books, where she got ahold of one of William's earlier books. ‘Curse of the Mummy.’ She moved over slowly examining it and looked back.

“I’ve been looking for this book for a while, and it hasn’t been in for weeks.” She would move over basically putting it in her bag. Rumble didn’t think much about it though looked over watching how her body bounced with how she was slightly bouncing in her excitement for finding the book. Rumble never actually seen someone this excited for one of these Books. He honestly thought he was the only one.

“Well, I’m glad that I was able to help, heh, She’s one of my favorite authors. I wish she was still writing books.” Sweetie seemed to only agree with him as she looked back to him giving that calming yet sweet smile. That seemed to grow with every second.

“I know right, it’s just a shame that they don’t publish her work. I’d honestly love to read and find out what Rainbow Storm is doing now.” Her laugh seemed to grow some. Rumble was sure that if she kept it going, she might’ve even snorted some. It was pretty cute.

“Well, if there’s anything else I can do, I’m willing to Help Sweetie,” he said feeling somewhat confident and proud to find another lover of the written word. At times it seemed like there weren’t that many people out there who really did. Sweetie nodded with a sigh heading off to the front desk. Beginning to check the book out and would head off maybe preparing for class. Looking at the time, Rumble saw that it was close to the end of the day. Time to get everything put away. Sure, he could just stay over maybe some overtime. But he had something he wanted to do after school.

Rumble walked back to the cart. His mind wandering some. Thinking of something. It didn’t really matter, it was just some abstract thought to distract him. Keep his mind busy for the next hour. He didn’t manage to notice the figure coming up right behind. He was getting close, picking up one of the books. It looked to be one by Horror King. ‘IT’ He was sure of it. Just from the pure size of it, and the big name of Horror King. He didn’t even bother looking at the title.

Before the young man could do anything. He suddenly felt grabbed from behind and basically forced against the bookshelf.

“Um.”

That was all he could manage to say his head-turning. This led to catching his attention. The long stand of silence when Rumble looked overseeing just who did that. What or who to be specific. It was Button Mash, Button Mash was the opposite of Rumble. He stood a little shorter than Rumble being around Five-Nine. Though weight over Two-Hundred pounds of pure muscle. With a dyed blonde-haired look with chocolate brown eyes. That had basically matched his skin color. Button Mash only gives him that dark sneering look. It was filled with anger. His teeth were crooked yellow. Definetly a earth pony with his sure strength and size

“Is there something wrong, Button Mash?” Rumble stammered as he felt himself being pulled up into the air. His back against the shelf.

“Yeah, there’s something wrong. A little faggot like yourself been talking to my girl. I don’t like that.” Button Mash shook his head with how he looked at him. Rumble didn’t know what to say right then. He looked over towards the side. No one was around them. What could he even do? He tried fighting this when he tried saying something.

“I was just helping her find a book, man. Relax, Button Mash I wasn’t even trying to do anything.” He tried saying though it was clear that Button Mash wasn’t taking this the way Rumble thought he would as he felt himself being slammed back into the wall a growl coming from him.

“I saw the way you were looking at her. That laugh so stays away from her, you freak.” Button Mash stated when he lessened his grip. Dropping Rumble who only slid down till he was sitting on the ground. Button Mash didn’t say much to him as he turned around walking off. Taking his time, as he went out of the Library. Rumble just shook his head with utter annoyance.

‘Well, someone compensating for a micro dick.” He thought and began putting the rest of his books away. He really didn’t bother with much. Why should he since he had some work to do. It was just another day in his life. It all only becomes one and the same.

~~~

It would be another half-hour before he managed to get his work done. It wasn’t much in terms of employment. Though Button Mash's words ran through his minds slightly,

‘I saw how you were looking at her.’ It was small though it just kept passing through him. Sure he admired he liked Sweetie, but the thing was she was dating Button Mash. A profusely dickish guy. But he wouldn’t try pursuing her. It wouldn’t work out. At least that's what he figured, he’d probably end up falling on his face if he tried asking her out. Then there was the fact he’d end up on the wrong end of Button Mash’s wrath. Now that was something he didn’t want to deal with. Button Mash’s family basically ran the town.

That might’ve been another thing for Rumble as he thought of it. There was another difference between him and Button Mash. It was social status. Button Mash was a rich punk who got anything from his daddy. The guy had money, more money than Rumble would probably never see in his life. There was no way he competes with the guy who basically runs this town.

Rumble only sighed while walking down the street’s just letting his mind slowly wandered. Rumble would begin moving down the road and started taking a turn walking off to the forest. The forest was known around town as the Whispering Hollow. The place had been around since the beginning of the city and thought to be where the original schoolhouse was located. The place where Ichabod Crane had supposedly met the Headless Horseman.

Rumble Crane began walking through the Whispering Hollow. The place was calm and quiet the perfect place to think. You couldn’t have a worry in the world walking down the trail. His breathing was soft and gentle with a book in hand as he moved down letting the fresh air breeze past him. The place was quiet and calming. The only sounds he could hear from off in the distant the occasional car driving by from the road. Then there were the sounds of birds chirping. They just made the sounds of them singing.

‘It’s just calming. I can just toss my troubles away for now. Though where should I relax?” He thought while continuing with himself. His head off in the clouds. Rumble was so preoccupied with where to relax, he never noticed how the birds stopped singing, and that everything seemed quiet. Moving on down the dirt road, for a long moment, that was when he started hearing a light noise that came from a distant.

“What’s that? It sounds like hooves?”

They did sound like that though they were slightly soft. The way it seemed. Rumble just imagined that it was coming from one of the local farms that resided close to the Hollow. So Rumble just decided to keep walking and going on his way. The only issue was that it seemed as though the clopping sound kept coming closer to him, moment by moment. It was coming right behind him when he looked back there. He suddenly noticed that fog was rolling in wrapping around him.

“Where this fog come from?” Rumble wondered as he suddenly began seeing a dark figured coming closer to him, and the sounds of the hooves coming towards him. Rumble was starting to feel every instinct in his body telling him to, “Run- Run!”

Rumble slowly began moving at a much faster pace, his heart pounding as he tried to get away. He didn’t know why he felt so afraid, but he didn’t want to stick around and find out. Though no matter how far he ran. It seemed whatever was coming closer. Nothing he didn’t seem to work, nothing he could do just brought the beating of hooves to get closer.

“What the Hell is going on?” When he looked back there, he began seeing a massive black figure. It looked onwards going towards him for the time, as he started to see a black steed. It was larger, more significant than any horse he’d ever seen before as it came straight towards him, and the creature’s eyes whereas red, almost like fire. The fires of a burning Hell. This brought on a wave of fear and panic. Though on top of this hellish steed, there stood a figure. But Rumble couldn’t tell who or what was riding this horse.

The figure seemed like a blur, as it stormed closer to him. It rode faster, as he listened to the horse snorting out its breath seemed heavy, But Rumble didn’t care he ran as though the Devil was chasing after him. Though maybe that was the case. Perhaps it was the Devil chasing him wanting his very soul.

It really didn’t matter, since he was trying to get out of there. Moving off, Rumble realized that no matter what he did, he couldn’t manage to escape the rider. So Rumble would do the only thing that he could and that jumped out of the way. Rumble moved to jump off the side down a pretty steep hill. As he rolled down. Grunting with each roll. As he did all, he could to slow down. But nothing seemed to help. As he managed to slow down. But was stopped when he hit a rather large tree.

“Dear God, that hurts.”

Rumble mumbled. When he moved slowly pulling himself up. He looks up the hill. There were a few things he saw. When he looked up and there, he saw. There he saw the Rider. The significant dark figure was sitting upon the dark stallion. The horse seemed to be scratching at the ground while the figured riding it just looked around. Like it was holding something, Rumble was feeling so nervous his heart racing. Showing no sign of slowing down as he thought himself somewhat tense, not knowing what might happen.

The closer that Rumble looked up, there was something odd about the rider. It was then he realized when Rumble noticed that this strange being had no head. This rider was headless. Which freaked Rumble out pulling all his will holding back as he was close to screaming.

“What the hell is that thing?” He muttered. But it wasn’t long before the Headless Rider began to hit the rains on that hellish horse, and there it was gone. Heading off to who knows where in some far distance. But Rumble stayed there refusing to move. He was frozen in fear. Imagining that that creature would come back.

‘What would I do if that thing came back?’

If anything Rumble would have to figure that out later. After all, He had to get out of here, if he didn’t know surely that thing would surely capture him. Going on, he managed to climb his way out of the ditch. His side just hurting. Rumble couldn’t help but wonder if his ribs were cracked. Slowly he managed to get out of the ditch, doing so He groaned, realizing that he was all alone. There was nothing there, except for a book. It was lying there. Rumble knew the book since it was his, as he slowly moved over limping, clearly banged up. As he picked it up.

“Oh, you’ve got to be shitting me.”

He simply picked the book up examining it, or rather what was left of it. The thing was destroyed. Pages ripped trampled. There was no way the situation could be even salvageable. As Rumble was watching the sheets that were ripped off flying off into the air, going on their own little adventure never to indeed seen again. Now, this wouldn’t have customarily caused Rumble such distress, besides the fact that. The book he had was somewhat rare and cost him a pretty penny. Just seeing it in this state just made his blood boil. Now he should’ve known better than to take a book like this out in the woods only to read, but the thing was. How was he supposed to know there was going to be someone riding on a damn horse coming right after him!

Sadly the deed was done. There was nothing that he could do. So he just sighed putting the book down and leaving it there. He didn’t want to have the reminded and only began limping his way home.

By the time Rumble had gotten home, it was late. The sun was setting for the evening, and the moon was in full bloom in the sky. This had been annoying. That was when his father came in, pulling the door opened.

“Where have you been boy?” The gruff voice coming from his father who just standing there at the door looking at his son, Who was only pushing his way into the house some.

“What happens to you Rumble?” His face turned somewhat concerned noticing how beat up he looked.

This was where Rumble had a choice telling his dad, the truth and understand about how he ran off the side of a trial by some crazy man riding on the back of a hellish horse or Lie. Just not to seem like he was going crazy. Rumble took in a deep breath and made his choice.

“I fell, Dad, nothing more. I wasn’t paying attention and just rolled down the hill wrong, banging my leg up just a little bit.” Rumble decided to go with a half-truth, since he did fall, by accident though not the way his father would expect. The old man just looked at him for a moment, watching over him with fatherly concern. Before shrugging off.

“Well, if you’re ok, get yourself cleaned up ok. I’ll be watching the game.” He walked back towards the living room. Rumble shook his head and just walked upstairs, His head wandering slightly wondering about what happened earlier today, was it all real? Or could it have only been his own imagination?

When Rumble got into his room, he sighed limping towards his bed and falling into it. The day had gone from being an ok day to a rather crappy one. So that was all. He was just glad that it was finally over with. Maybe tomorrow would be a better one.

That was when he heard a small buzzing coming from his pocket. As he caught his attention as he reached down towards his pocket and seeing who it was that had decided to call him around at this time. So Rumble looked down at his phone, seeing an unknown number that was calling him. Usually, Rumble would ignore these kinds of things, but a gut feeling just told him that he might as well go and give it a try. So he over and began to answer the phone.

“Hello, This is Rumble?” He asked cautiously as he waited for an answer. If it was just an electronic voice, he’d probably just hang up. Though nearly instantly, someone did answer. A somewhat familiar voice.

“Hey, Rumble. It’s me Sweetie.” Rumble wanted to felt his head sling right up. His eyes widening, hearing just who it was. How’d Sweetie even get ahold of his phone number?

“Sweetie? Wait, how were you even being able to get ahold of my number?”

There was a second of silence between the two of them, while Sweetie had answered,

“I asked one of your friends, and he simply handed it over, though that’s not the point I really wanted to ask you something.”

“Well ok… What do you want to ask me about?” He was rather curious, as she had spent time getting ahold of his phone number, just to call him.

“I’m going to be having a party at my house for Halloween, and I was wondering if you’d like to join me?”

Rumble imagined if he had something to drink, he would’ve choked on it, and spit whatever was in his mouth.

“Wait… what?!” He felt himself resisting the urge to shout when he investigated his phone. Seeing if this was a joke, but all Sweetie did was giggle slightly when she moved onwards.

“Like I said, I’m having a party, and I thought I’d invite you. So would you like to join me?”

“But what about Button Mash?” Rumble asked, trying to keep himself calm as he remembers what happened just this morning when him and Sweetie had barely even talked. Though Sweetie just continued,

“What about Button Mash? Come on now, he’s just a sweet guy he wouldn’t mind.”

‘Sweet my ass!’ Rumble thought, as he felt his heart racing, what was he going to tell her? No- He probably could but for some reason, he just couldn’t something in his gut wanted him to go, and Rumble just couldn’t seem to explain it.

“Well, I guess I can come over for a bit. It shouldn’t be too much of a problem.” Rumble responded as he felt like he had no choice. Everything seemed so crazy, and he didn’t know how to feel. So he decided to go with it.

“Oh god, thank you, thank you so much Rumble. I can’t wait to see you there. Here’s my address, please be here around eight this Friday.” She would begin telling him where her address was, and not long after that, she proceeded to hang up on the spot. Rumble sat there for a minute in utmost Silence, as he felt the phone slowly slip out of his hands and hit the ground.

It was nearly impossible to believe what was actually happening. Just the idea that he was invited to a party with such a beautiful woman was something he could only imagine in his dreams but here he was. Invited to some party with a girl he barely knew who he was seriously crushing on. His heart pounded, and soon Rumble found himself going to sleep and falling into a dreamless slumber. Not a single thought about the headless horsemen. Simply relegating in the background.

Author's Note

Well here's a fun parody of Sleepy Hollow with some of our MLP CHaracters and please let me know what you think of part one and part two should come sooner or later while i work on it. If you enjoyed this let me know what you think, and also if you enjoy this follow me on twitter or my discord, plus I've got a patreon if you want to support me.

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Eri Stoner

a new way to get head

Friday couldn’t seem to arrive fast enough, at least for Rumble, at least. He was looking down towards his phone, Watching over it. While Remembering observing the Address. His long strides as he walked quickly. Rumble didn’t seem to pay attention as he walked on. The street wasn’t the most helpful compared to the rest of the town. But for Him, his mind was somewhere else as he walked off.

Rumble’s phone finally indicated where he was As he looked up, and soon realized something. This was definitely Not Sweetie’s house. The place was an old home long since abandoned.

Rumble tried walking away, feeling annoyed. It was clear that all of this was some kind of joke. As he didn’t even bother trying to get inside. He eventually turned around and walked back the way he came.

But that was when he realized someone was right behind him. Looking and saw two figures standing there. A light laugh, it was Button. A toothpick set between his lips as he chuckled,

“Look here the Faggot actually thought he was invited to a party. What a shit, fuck.” He chuckled, looking over at one of his pals. The guy just laughed while smashing his fist into his hand. Rumble took a step back since he didn’t like the odds, as he started to run.

“Get him!” Button growled, there the chase began. Rumble felt his heart racing hard, as he was running harder than he had in his life. But the way it went, and Button was definitely faster than him. So he needed to think fast. The only thing that came to mind was running into the road. A car coming down and pretty quick, It was such a surprise Rumble didn’t get hit as he reached across the street. But Button didn’t seem to take the risk as he screamed something out to Rumble, but the young man couldn’t hear him as He was too busy running the other direction. His breathing was getting heavy, and his legs were burning.

Till finally, Rumble had to stop and Rumb ran over. He just stayed that way trying to catch his breath, though before he could have a second, he heard Button screaming out to him much louder,

“Oh, you better fucking stay there cause if you run, it’s going to be much worst when I get my hands round your neck!” Rumble’s eyes shrunk, watching as the jock was standing across the street looking back and forth, as the roads began clearing away. Rumble gulped. Fight or flight finally took over, and Rumble did the only thing he did best… He decided to run.

He realized he was getting closer to the woods, and something just clicked as he turned into it and ran inside. He hoped for the best as he ran deep within the dark forest. Rumble might’ve been hoping that the trees would hide him from Button's wrath, and eventually, the man would give up in his hunt for Rumble Crane. Though no matter how far he ran he could hear the man calling out for him screaming his name,

“Rumble, you fucking bitch get out here and fight like a real man!” He tried thinking of something when he stood in the middle of the trail. As he noticed how he was in the same spot where he’d seen the headless phantom. Riding away,

“Oh, wow, I really wish It would show up. I think I’d rather deal with that think than Button.” He tried looking back and forth when without warning, he felt something pull him back. His head jerked back as he looked back and saw none other than Button. The crooked smile growing as he was close to lifting Rumble off his feet,

“I told you that it was going to hurt more if you ran, and it’s definitely going to hurt you.”

He reached raising his fist ad Rumble tried to escape Button's grip, but nothing he did seemed to work. As he felt a punch slam right into his face. The pain was overwhelming; in fact, Rumble imagined that his noise might’ve been broken, his eyes burning up. But soon he heard something. It was the sounds of hooves clicking on the ground, getting closer.

“Oh, no,” Rumble said as he tried looking around. He was imagining the headless Spector would arrive soon, but Button wasn’t paying attention, as Button was too busy beating the shit out of Rumble. His punches getting harder on Rumble’s face. Never noticing the sounds of hooves getting closer.

Then without warning, Rumble felt himself being thrown off as He looked over and saw that Button was against the tree knocked out cold. His right arm was Rumblet off in the opposite direction. It didn’t look right. Button's arm was definitely broken. He reached over and was getting ready to check on him. Sure the guy was beating the shit out of him, but still, he looked pretty beaten up.

“Button, are you alright?” Though it seemed that Button didn’t respond. Rumble reached over and touched his neck as he waited for a minute until finally, he felt a heartbeat. It was clear he was alive. So that was a relief.

“Well, I should get up before he wakes up, Cause it’s not going to be pretty.” He turned around and realized something. He still wasn’t out of the frying pan, he was in the fire. Standing there upon a black horse stood the figure, clearly without a head, He finally looked in closer

The character was more feminine than he remembered tall and slender even while on the horse, her body was like an hourglass, as she wore black leather over her body clinging to every inch of her. Her breast was rather significant, about as big as his head maybe more significant. If Rumble could guess she was a G cup.

Rumble looked towards the figure more, as he tried taking a step back. He wanted to run but was frozen in place, Rumble could actually imagine that this would’ve been the end. How would he be able to escape from this hellish beast? That was when he heard the voice.

“Hey, Hey!” The feminine voice calling out to him till finally, it caught his attention. The hand moving over and began pointing down towards her side. He looked towards that direction. Hanging from the body, wrapping around the belt was long flowing hair red hair, like fire. It looked soft while shined as he continued searching, seeing what was dangling from those locks of hair. He saw a face.

It was a woman’s face, and to Rumble, Her face was beyond words. Eyes as stunning and as deep as the blue ocean. Sure she had some scars and marks over her chin. But added character. The only thing that was distracting from this was the fact her head wasn’t attached to her body.

The woman detached head spoke.

“My eyes are down here’s! Quit looking at my Tits!” She seemed to eye him. It wasn’t long before her hands reached over untieing the locks of hair as she raised it up and looked at his face to face.

“Oh, um. I’m sorry… I’m just not used to a woman who didn’t have a head on her shoulders.”

“Ha, ha Haven’t heard that one before. Who are you, and why did that guy try and choke you out?” She wasn’t amused by this as she seemed to be looking over Rumble more. Since he didn’t want to anger her, he told the truth.

“Honestly, Button, here’s a jealous dick, I talked to his girl, and I guess it really pissed him off.” He tried keeping a calm look as he did his best to take a step back. But when he did. It seemed the headless woman kicked her horse to cause it to push forward.

“Hmm sounds like a man my grandfather told me once. About a man named Brom Bone.”

“Wait, did you say, Strong Bone? As in Strong Bone from Sleepy Hollow?”

“Yes, that story, My grandfather says that it is rather inflated and gayly.” The headless woman said for a pure calmness.

“Wait, so your grandfather… Your grandfather was the headless Horseman!” this was rather exciting and terrifying as he was looking at what could be considered a legend. Though Rumble would pick himself up, while The mysterious woman moved on some,

“He was though my father laughs at this story, claiming it was incredibly flamboyant and very much a myth. Grandfather said he never even touched The old schoolmaster. More like scared him as he rode off into the night.”

“Wow well, that was… Insights, um, thank you. My name Rumble.” He raised his hand up though he realized it was his right hand, which was straight at her face. So quickly changed over going to the left.

“Hello Rumble, I am Tempest Shadow. It’s an honor meeting you.” She would slowly proceed to walk away riding on her horse, as it seemed to be close to the end, but Soon Rumble moved following behind you.

“You said that the legend of Sleepy Hollow it was a myth, How so? I mean, if your grandfather was there and was, in fact, the Headless Horseman?”

“We prefer to be called Dullahans lad if you don’t mind, and to explain it, We refer to it as a myth, as My grandad, was never a mercenary, and was brought here from his home in the Emerald Isles. Forced over and found himself wandering around this quiet little town. Living off in the old forest in the west before it was cut down many years ago.”

“Well, that’s interesting, Dullahan’s So basically Irish fairy’s.”

“Is there a problem with that?” Cara said with a slight smirk as she seemed to be reaching over to her whip, But Rumble raised his hand, as he held it up.

“No- No, not at all! It’s pretty cool, really.” They seemed to walk off going more in-depth in the forest Rumble wasn’t thinking much about it till finally, they walked towards what looked to be an instead run-down schoolhouse, She motioned over slapping the horse by the side causing it to gallop faster. Rumble began running after her faster doing all he could to keep up till Cara stopped in front of the schoolhouse.

“So, this is where you live?” Rumble asked almost stupidly, while he Rumblet over taking a deep breath, Tempest looked over with as she simply stated,

“It’s much nicer on the inside. This was once the location Icabod Crane uses to teach his students before he ran off.” She was so calm almost cold, but she looked towards the young man who was even more shocked looking towards the schoolhouse. His attention overwhelmed as he imagined this place was beyond legendary, and soon he couldn’t help but wonder if this might’ve been related to the old schoolmaster, Besides he was standing next to an actual Headless Horsewoman.

“Come in if you want; otherwise, you can follow the trail back home.” She pulled herself off the horse and showed she was a few inches taller than the man, and that was without her head as she held it up with one hand and used the other to begin unlocking the door while she headed inside.

Rumble proceeded to follow her. Walking right inside as he got a good look at the place, and Tempest was right, it wasn’t such a crapshoot as the outside looked like. It wasn’t perfect being messy, but it was a decent and calming home for most people. It felt homely.

“Take a seat and pick up your Jaw we don’t have all day here,” Tempest said as she let out a smile She soon put her head on the chair as she rested it over. Rumble just seemed curious as he watched her body walk off into the back vanishing.

“Uh, where’s the rest of you going?” Rumble asked, instead of wondering more as he took a seat by Tempest’s head.

“Oh The rest of me is just freshening up. After al, riding off in the late night can be taxing a girl’s got to keep her image up.” She laughed as she rolled her eyes as she seemed to get more comfortable.

“But don’t you need to control your body and tell it where to go?” Rumble quickly asked more curious as Tempest seemed to only sigh as she appeared more aggravated by the repetitive questions.

“My body can do stuff on its own while I’m not around it while, we’re here, it’s so used to it that it could walk around blindfolded, and could find its way.” Tempest giggled slightly at her wording, though, for Rumble, it took him a moment to realize it and soon joined the head in a fit of laughter. Rumble laid back some getting comfortable as he looked around a little more,

“I do owe you for helping me out there. I mean, Button really would’ve kicked my ass back there.”

“I think he would’ve done worse if I hadn’t arrived. But yeah, you owe me, and this is the second time we’ve met.”

Rumble blushed more as he remembered him falling over sliding down the ground when he tried avoiding her the first time,

“In my defense, I’ve never met a headless girl before, and I hadn’t realized you were one, So, I kind of freaked out.”

“Obviously, though, what's wron never seen a girl with a good head on her shoulders?” Rumble burst out laughing at this unable to control himself at the terrible, terrible pun. Tempest thought wasn’t amused by that,

“Though in all seriousness what were you doing in my Forest?

“Well, like you saw before, I was trying to escape a beating from Button, nothing more.

“I’m beginning to see a theme, well I think you’ll be fine if I send you back home, I’ll even let you ride Mist. If I must.” Giving a smirk as she begins jerking her head off to the side while she looked over towards the door when she looked toward it. It was clear her body had returned wearing only a towel.

“Hey, put some damn clothes on!” She yelled at herself, but it was clear her body had a mind of its own, while it pushed her head and sat down, seeming to get more comfortable. Tempest only growled in annoyance as she realized that her body was no brains all heart. And looked away with a grunt.

Rumble wanted to laugh, but was too nervous about offending her, and what she might do to him if she had a chance.

She hasn’t tried hurting me yet. Rumble thought while taking a deep breath and getting more comfortable, He was a guest after all, as he leaned back.

“I guess you’d body has a mind of its own.” He snickered slightly as the head groaned in annoyance. While she took a deep breath,

“Are you thirsty? My other half can get you something before we go any farther?” Tempest asked though Rumble shook his head, trying his best not to look over at Tempest’s naked body. She was definitely a sight, and In truth, this was the first time he was ever in front of a naked woman. Sure there was the internet, but being in front of a living woman, even one who was headless, in this situation was quite the sight.

She looked over towards her body and told it,

“Grab me a tea if you will.” The Body only nodded and gave a thumbs-up before walking away. It would go away for a few minutes and soon bringing a cup of tea and a straw as it sat it in front of Tempest.

“Thank you.” Tempest’s head said as her body moved now sitting next to Rumble. Her body seems to do its own thing as it started wrapping its arm around Rumble.

“Well, I really do owe you, Um if you ever need anything, I’m here.” Rumble chuckled trying to rub the back of his head, almost surprised, not knowing what to actually say. Though Tempest smirked,

“Yeah, I imagine you do, and I have you at your word if I ever need anything you’ll help. And we’ll definitely be seeing each other soon.” Suddenly Rumble felt Tempest’s hand running down his arm rubbing it slowly getting a good feel as it started moving over towards his waist. Rumble looked over at the body as it seemed to be moving on its own for the second, and he laughed almost nervously.

“Is your body normally this affectionate?” He was curious looking back to the head across the room, as she shook it.

“No normally not, hey you stop that!” She yelled at her body though it seemed like it wasn’t listening. It’s hands moving around in various forms,

“What the hell do you mean fuck off he’s yours!”

“Is your body speaking in sign language! What is she wanting?” Rumble asked but Tempest didn’t need to give him an answer as he felt her body squeezing between his legs as he bounced into the air before falling down. He let a slight groan, as her hand felt night against him.

Her other hand began doing all the talking, moving back and forth communicating with her head,

“I don’t care if we haven’t been with a man in ten years, You keep your hands off him!” The body only flipped her off much to Tempest’s annoyance. Rumble would suddenly feel his zipper coming undone, and soon heard it as the sound went off as he looked down, watching those delicate hands from the Dullahan moving over and pulling out his soft cock.

Rumble somewhat wondered what the body was thinking or what it might say but he groaned as Tempest started wrapping her hand around him and started jerking him off.

Tempest hand moved back and forth jerking him faster as he let out a groan. He found himself unable to move but in some ways it made the experience feel even better. His hands grabbing the couch holding on for dear life. While he grunted.

Tempest’s head on the other hand was much more annoyed,

“Seriously body, right now, Couldn’t even have convinced me into trying to seduce him… I mean he doesn’t even look like he’d need much convincing.”

Rumble grunted as he felt the second hand grabbing ahold of his junk moving faster, as he arched his head back lost in his pleasure, while thrusting his hips humping her hand with such a desire. Lust slowly consuming him.

“Alright that’s enough let him go, I’m sure you’ve freaked him out enough, or gotten him overly excited.” Than Rumble felt slightly annoyed as her hand slowly pulls away. Rumble watched as he saw her getting up and walking back towards the other chair while Tempest smiled at her body,

“Good now that we have that settled we really should get you back home.” But before she realized it, Her body grabbed ahold of her head and soon pulled it back over, shoving her face right into his cock. Tempest’s lips pressed against his lips as Rumble grunted groaning hard.

Tempest only muffled in confusion as she rolled her eyes back towards her body and muffling something. But Rumble couldn’t hear her as she was soon getting a mouth full of his cock penetrating her moving down as He gasped harder.

“Oh, fuck!” His head rolled back as he never felt so alive. His hips moving as he gave a grunt. Tempest’s mouth was feeling even more amazing. But not long as he felt something push against his face. Rumble quickly opened his eyes and found him face to face with one of Tempest’s tits her nipple sticking out and hard, and not being one to deny a generous gift proceeded to suck on it, his mouth wrapping around it as he gave light nipples.

Tempest, though seemed to moan and grunt more, as he felt her nipping his pecker. It caught him off guard and nervous as he looked down the best, he could without removing his mouth from that fine breast. His other hand reached over caressing and massaging the other one.

Sure it was bright Tempest annoyed in the situation. Her hand pushing her down on his thick cock, but she seemed to be a good team player. Rumble proceeded to play with her breast. Firm and warm. As he massaged her right bosom, he could feel her heartbeat, it was racing by the second steady thumps as he continued playing with them.

Though soon like all things it came to an end when without warning he called out, feeling an orgasm spring out,

“Fuck, I- 'm Cumming!” His release was strong feeling it fills the Dullahan’s mouth. Making him wonder where all his spunk would go, would it drip down from where his throat was all over the ground? It didn’t seem to be the case as he watched her swallowing and coughing some before the head finally pulled her away from his member. That for all sense and purposes managed to remain erect.

“I swear you could’ve fucking warned me!” She growled, looking towards her own body. Rumble actually felt rather sad about that, and more while he simply said,

“Sorry I didn’t mean too.”

“No, you’re fine. It’s this bitch. I swear if you weren’t my body, I’d kick our ass!” She growled more annoyed though the body clearly never gave a fuck while moving over and pulled the body onto her shoulders as she seemed to balance on there for a second.

“Well, I guess that’s the end of that. I think we should be. Wait, what the hell body you want more!”

Rumble definitely knew what her body was planning. While he gave a grunt, as the body got right on top of him directly on his lap, as his member rested right between her butt cheeks. Her butt giving it a light squeeze as she looked towards him.

“It looks like my loins are doing all the talking at this point. Once my body gets an Idea nothing going to stop her so just lay back and enjoy yourself.” Her breathing seemed to be getting heavy as she balanced herself on her shoulders, pushing Rumble back against the couch cushions.

Rumble Nodded as The Dullahan, simply Smiled some. It was clear she was going to enjoy herself since she had no control over her body at this point as she lifted herself up, her ass jiggling as she used her right hand adjusting his cock while moving over. Some the head pushing against her pussy. It felt warm against his cock head.

Tempest felt her body push down and gave a slight groan, as she could feel what her body felt and the cock was spreading her pussy apart with a long moan, as she thought it penetrates her more profoundly moving slowly. Her hips rolling back and forth grinding, While Rumble gasped his hand, reaching over cupping the monster girls fine ass so firm in his hands as he held onto each cheek. Tempest groaned as she grabbed his shoulder. Soon bouncing on his hard warm cock.

“Like that, Rumble? Do you like how fucking my tight pussy?” She gasped more as she began riding him, Her body shaking, her heart beating faster by the second. The couch rocking under the two as they continued fucking faster, and quicker.

Rumble breathing heavier. This was his first time. He couldn’t describe it at all but what this woman was doing to him was something he never expected. But it was something he’ll always remember. That was when he reached over and soon slapped her ass. The sound of their skin connecting, as it began jiggling. He grunted more as He felt Tempest grabbing his shoulders, slamming down onto him with a hard grunt, while moving over more, Her other hand grabbing her breast, soon massaging them.

“Fuck!” She moaned more, as she felt a fire burning into her, as the pleasure was running through her.

Tempest was in control as she howled like a banshee, letting her voice e heard for miles around as she enjoyed herself. She wasn’t even thinking of Rumble as she was riding him faster, like a horse. While making sure that she felt her pussy tightening around his member. Her eyes rolling to the back of her skull.

“Yes, yes, Yes, ohh fuck yes!” Tempest was bitting her lips if she did it any tighter she might’ve started bleeding. There was nothing more to it as she felt herself getting closer to the Big O.

Rumble was getting overwhelmed his cock was so sensitive and he was getting closer to his second orgasm, It was a hard breath as he was about to reach another second orgasm, while he moved his hips faster, thrusting faster, as she was driving him insane. What was he going to do as he was breathing heavily. His heart Racing also, while he looked over watching just how the woman tits bouncing faster.

Rumble actually felt himself getting closer… His balls filled with cum as he wanted to feel released, but he tried holding it back, He tried his hardest but how This Fairy was bouncing on him he couldn’t as he exclaimed to the heavens,

‘I’m Gonna… I’m gonna cum!”

“Me too, Oh yes, Fuck it’s been fucking years since I did this!” her tongue sticking out as Tempest felt as if she was going to explode. The two just kept going at each other almost unrelenting, as though they were trying to starve their orgasm, and not wanting to cum. But in the end, it didn’t matter, as Rumble was the first one to release his seed, and pumped it he did. Rumble filled her with everything he had, as Tempest screamed off into the heavens as she began feeling herself orgasming harder than she had in a long time. She felt as if she wouldn’t use her fingers or even her own head to satisfy her again.

For Rumble, everything seemed to go dark, as he felt completely relaxed for the first time in his life, and soon Rumble would find himself falling into a deep sleep.

~~~

When Rumble finally woke up, he found himself lying in his own Bed. His own alarm clock going off, as it beeped excessively. Nothing more, a Book by him that read with the Cover Sleepless Hollow. It only caused him to groan, as he soon pulled himself out of his bed, when he realized that he still had the same clothes he was wearing the other day, and grunted.

“I must’ve been exhausted, I don’t even remember getting into bed. Weird dream.”

He proceeded to change and get ready for another day at school. After all, it was Monday and it wasn’t going to change that.

When he would eventually make it to school, he began hearing things. Apparently, Button had gotten attacked his arm broken when he was discovered passed out in the woods. When people tried prodding him more, he simply remained silent, not wanting to say a single word. It was inevitable though. With how fucked up his arm was, He would never be able to play football again. His arm would never be the same.

He walked on to his last class when he heard a voice that seemed almost too familiar.

“Mr. Crane, you’re Late!” He looked away from his book as he realized he was looking over at none other than Tempest, the Dullahan, who seemed to be looking towards him somewhat annoyed. She was wearing fine, elegant clothes that gave her a professional look.

“Um, sorry it won’t happen again… Where’s Mister Bone?” he asked, almost curious though it seemed that Tempest wasn’t much of a talker there.

“You can say he lost his head. Now please take your seat this instant.” Rumble would oblige.

The class went off without a hitch though before he left, Tempest would soon call out.

“Rumble, you are to stay here for a moment. For being late You’ll be serving detention.”

Rumble cursed under his breath as everyone walked away, and when they were all alone, Tempest only smiled and sat down, crossing her legs almost teasingly as he noticed she was wearing a set of black panties.

“So Mr.Crane, do you make it a habit of being late?” She asked as she moved back, getting more comfortable sitting on her desk as she reached over. Rumble imagined she was going to move some of her hair, but instead slowly took her head off her shoulders…

“No words. I should punish you for being such a naughty boy.

The end

Author's Note

Hey guy's well sorry it took long to get this done but here it is the newest and last chapter to Sleepless Hollow I hope you have some fun with it. I enjoyed having fun writing it thats for sure. and if your Interested I am taking Commissions, so PM me if you want and we can have a disscussion. Also if you want to support what I'm doing check out my patreon. or just buy one of the books I've written I'll leave a link there also
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Also here's a pic of how I imagine Irish creatures Spend a friday night