Daring Do: The Night Before

by CeasarTwain31

Rating: mature
Tags: Profanity, Romance, Porn, My Little Pony: Friendship is Magic, Dr. Caballeron, Sex, Daring Do
Length: 2479

What really happened the night before between Daring Do and Dr. Cabelleron

Daring Do and Dr. Caballeron head back to Daring's hotel room after a long day of promoting their new co-written book together. But with liquid courage having been consumed by both of them earlier, things heat up between the former enemies.

My first Clop attempt so please be merciful.

Also, this is a prequel to another story of mine, Daring Do: The Morning After

Published 2020-07-15 13:40:01 UTC
Last updated 2020-07-15 13:40:01 UTC

The Night Before

Author's Note

This is my first attempt at clop......

please have mercy!

The Night Before

The taxi carriage screeched to a halt in front of a large High End Fillydelphia hotel and two ponies clumsily stepped out of the carriage and through the front doors of the hotel. With it being around 11pm, most of the guests were already asleep or out somewhere in the town. The only pony present besides the two from the carriage was the front desk clerk, who saw the two enter in the lobby, stumbling and huddled next to eachother as they made their way across the lobby floor and into an elevator.

The hotel was currently hosting a large convention about one of the most popular literary creations in Equestria, Daring Do. The convention had ended that day, and many ponies had shown up for it. The ponies dressed up, purchased merchandise, took pictures, and even got to get their books autographed by the series current co-authors A.K Yearling and Groom Q.Q Martingale. With all the tourists and cosplayers, the desk clerk assumed that the two who entered were just some inebriated cosplayers coming back from a bar, so he went back to his book.

Though in reality, the two ponies that had stepped into the elevator WERE the co-authors of the books, only, they weren't wearing their author disguises. They were Daring Do and Dr. Caballeron.

The two had spent the morning signing books and taking pictures with fans, until dropping the disguises and wandering around the convention, and due to all the cosplayers, they were able to pass as just a few normal fans.

After wandering the floor for a few hours, the two decided to grab a bite to eat at a nearby Fillydelphia pub, where they had just a little too much to drink.

After some lewd comments and nearly breaking a table, Caballeron hailed a taxi carriage, and took them back to the hotel. The entire ride, and up to the elevator, Daring Do was nuzzling herself quite heavily into Caballeron's side. Once in the elevator they separated while the elevator went up.

"You should really watch your alcohol." Dr. Caballeron said to Daring, very amused at how bad she was at holding it, considering how drunk she was. Daring smiled back at him with an intoxicated gaze.

"Oh, shut up you! You had some too!" Daring argued.

"But not as much, and I'm also bigger, so I can hold it better than you, being as thin as you are." Caballeron slurred out, looking over the slender mare. His gaze landed on her compass marked rump, where he held it for a while. He was still drunk alright. Daring spoke again.

"Psssh, whatever, just help me get back to my room." She said with an eye roll. Caballeron nodded and slung his arm around her again as the doors opened and they stepped out into the hallway.

The walked slowly to the end where Daring's room was. She took a moment and drunkenly fumbled with her room key before finally unlocking it. After it opened, Caballeron helped her in and the two stumbled out into the room, and the door shut behind them.

Daring was about to thank Caballeron for his assistance, when she looked into his eyes. They weren't spectacular, but they had something about them that Daring liked. She trailed her eyes up to his mane before looking down to his stubble on his face and his chiseled jawline before going all the way down to his chest and over to his flank. Daring looked back up at his eyes and gave him a seductive grin.

"You know, you're quite the Hunk Dr. C." Daring said. Caballeron blushed for a second before eyeing her up as well, from her greyscale mane, her rosy eyes, her slender figure, and her supple looking flank. Caballeron grinned.

"You're quite the eyeful yourself Miss Do." Caballeron said, pulling her in closer.

"Oh, what are you saying Dr.?" Daring asked. Just then, Caballeron gave her a playfully sinister smirk and quickly pushed her up against the wall, pinning her to it up on their hind legs. Daring let out a gasp and blushed as she looked at her position.

"I have you now Miss Do!" Caballeron said in a way similar to how he would in her books. Daring knew what game he was playing now.

"What are you gonna do with me?" Daring asked, giving him bedroom eyes. Caballeron simply grinned, he reached his head up and tossed her helmet to the floor using his teeth before moving back down and pressing his lips against hers and pulling her into an intense make-out session. His hooves slid up and down her thin sides and smiled as he heard her let out little squeaks and moans. Daring started to press her tongue against his lips, which he quickly responded by parting his lips and meeting Daring's tongue with his own. Their tongue began to wrestle with eachother, ultimately ending with Caballeron's tongue pinning Daring's to the bottom of her mouth.

After an long session of making out, Caballeron pulled away panting. Daring's face was overtaken with a very strong blush.

"Wow, went right in, didn't you?" Daring asked with her eyes half-lidded. Caballeron smirked back at her.

"I'll go further if you want." Caballeron said. Before she could respond, he leaned back in and began kissing around her chin, cheeks and neck. Occasionally he nipped and nibbled on parts of her neck, making her moan and squirm even more. He traveled lower, eventually reaching her green shirt. He then used his teeth to start undoing the buttons one by one.

Caballeron took a second to process what was happening, here he was with his former nemesis, alone in her hotel room, and he was undressing her. He smirked and continued unbuttoning her top, eager to continue.

Daring's slightly sluggish mind also began to process their current position. Pressed against a wall by one of the many adversaries that she had spent years fighting, giving into his caresses and kisses. And she loved every second of it.

After the last button was undone, Caballeron spread the shirt open and continued kissing and nuzzling the tufts of fur on Daring's chest. Daring herself started to nuzzle into Caballeron's frizzy mane. Caballeron's hooves, which had been rubbing up and down her sides, slid all the way down to her flanks and began rubbing them.

"Oh." Daring moaned as she felt his hooves on her rump. Caballeron smiled as he continued to kiss her chest and rub her flanks. He moved his hooves in circular motions and pressed harder against them occasionally, getting more squeaks and moans out of Daring. After a few minutes of this, Daring lifted her head out of his mane.

"You really like my ass don't you?" Daring asked. Caballeron lifted his head away from her chest and back to eye level. He simply responded with a smirk and squeezed her rump once more.

"Does that answer your question?" He asked as he slowly rubbed it more. Before Daring could say anymore he slid his hooves back up Daring's body and removed her shirt completely, leaving her whole body exposed to him. Daring smirked as well, and once Caballeron was done undressing her, she slid her hooves up to his shirt and pulled it up and over his head and tossed it on the floor by her shirt and helmet. The last thing left was his ascot, which he untied himself and dropped it. Daring rubbed her hooves against his chest, feeling his muscles.

"You wanna keep going?" He asked. Daring answered by feverishly attacking his lips again, drawing him into another make out.

As they made out once more, Caballeron felt around her body and could feel something else begin to stir down between his legs. He brought one hoof to one of her flanks and began massaging it again, while another hoof went down between her legs and began rubbing her slit, which was already beginning to become slick and wet.

"OH! Oh My Gosh!" Daring moaned as Caballeron's hoof came in contact with her wetness. He began to rub it slowly at first, but slowly gained speed. Daring panted and moaned as Caballeron worked his hooves over her rump and pussy. Daring kept panting and moaning louder and louder until the constant and quick rubbing led her to her orgasm. She buried her head in the crook of Caballeron's neck as she rode out her climax, coating Caballeron's hoof with her juices.

After her climax subsided, Caballeron retracted his hoof from her slit and brought it up to his muzzle. He took a sniff and licked it. "Mmm, delicious." He said with a seductive expression to Daring. She decided to move their next activity to a place more comfortable.

Using her wings, she forcefully pushed off the wall, effectively pushing herself and Caballeron towards the bed. Caballeron fell backwards onto the bed with Daring landing on top of him, sprawled across his chest.

"Eager huh?" Caballeron asked as he wrapped his hooves around her back. Daring nodded.

"That, and the bed's more comfortable." Daring said before plunging her lips against his again. Caballeron slid his hooves down and once again began to rub her rump. As they made out on the bed though, Daring felt something brush against her chest. She pulled back and looked beneath her and grinned.

"Who's the eager one again?" Daring asked. Caballeron grinned and rose one of his hooves before swiftly bringing it back down and smacking one of her flanks, making Daring let out a noise that sounded like a moan and a yelp combined.

"I think we both are." Caballeron said. Daring smirked and planted a kiss on Caballeron's nose.

"Well then, let's not keep you waiting." After Daring finished speaking, she began to kiss down his body, moving over his chest and belly before finally reaching his member, which had grown to its full length, which Daring found very impressive.

"You're a bigger stallion than I thought." Daring said smugly. Caballeron playfully glared at her.

"Hey!" He said, about to argue back before Daring began a lick at the bottom of his shaft and dragged her tongue up the length of it. She licked it several more times before taking the tip into her mouth and bobbing her head on it.

Caballeron watched her as she gave him head, and placed a hoof on the top of her head, simultaneously signaling her to keep going, and stroking her grey mane. Daring continued to take more and more of his cock into her mouth and began to pick up speed. This time it was Caballeron letting out the moans. He felt the pressure mounting in his loins as the intense feeling of Daring's mouth and tongue against his cock began to make his climax quickly approach. But before it could fully come to him, Daring retracted her mouth from his member, leaving Caballeron disappointed and slightly angry.

"Hey! I let you cum!" Caballeron said angrily. Daring placed a hoof against his mouth.

"Shhh, I decided to leave the best for last." Daring said sensually as she climbed higher over Caballeron's body. She stood on her hind legs, placing her still dripping pussy over his still erect member. Daring looked at him, and he gave her a wink and a nod, and she dropped her pelvis, and his cock went inside her.

"AH! Oh YEAH!" Daring shouted out in pleasure as his cock went in her. She hadn't had sex in a long time, and now she could remember how good it felt. Caballeron laid his head back as Daring began to ride him. His hooves clenched around Daring's rump, groping her as she slid up and down. Caballeron eventually began bucking his hips up in time with Daring's bouncing.

Daring continued moaning and gasping in pleasure, she looked down at Caballeron who was now looking up at her with a grin and a lustful look in his eyes. Daring smirked back at him and plunged her lips back onto his and began to make out with him as their hips kept moving.

The burning feeling inside Daring kept growing and growing for her, before eventually hitting it's peak. "AAAAH!" Daring moaned out in pleasure as she reached orgasm a second time. Her juices spewed out of her pussy, coating Caballeron's member in the process. Despite have came, Daring kept riding Caballeron, since he still needed to finish.

"You...you are the sexiest, most amazing mare in Equestria!." Caballeron said between gasps as he kept bucking his hips up, the burning feeling beginning to be felt as he rammed his cock inside her again and again. Daring blushed hard at the complement, knowing the irony of that statement, considering their relationship in the past.

"I...I'm close!" Caballeron suddenly said. Daring plunged herself on his cock a few more times before pulling out completely and seeing his tip flare and spew forth the white liquid partially onto Daring's body and the bed. After his orgasm subsided, Caballeron fell back onto the bed limply, and his tongue was hanging out the side of his mouth. Daring giggled as she looked down at the mess they made.

"Wow, looks like we got messy." Daring said as she climbed up and planted a kiss of Caballeron's snout. He smiled back up at her. "I'm gonna clean off, be right back." Daring said as she slowly got up off the bed and limped over to the bathroom. Caballeron simply laid back on the bed and stared up at the ceiling, feeling really good right now.

After a few minutes, Daring joined Dr. Caballeron back on the bed and laid beside him. She looked over and saw that he was already drifting to sleep. She quietly leaned over and planted a kiss on his cheek and nuzzled his neck for a second, he suddenly opened his eyes and looked back over at her. He rolled over on top of her and started to kiss and suck at her neck again, making Daring laugh.

"Okay, okay, that's enough for one night!" Daring said, placing her hooves on his chest and pushing him slightly off her. He placed his hooves on either side of her and looked down at her with a smile.

"Thanks for such a good day, Miss Do." Caballeron whispered. Daring smiled back and pecked him on the cheek.

"Don't mention it.......Martingale." Daring said mockingly. Caballeron snorted before shuffling back down beside her on the bed.

"Goodnight, Ms. Yearling." Caballeron mocked back at her. She let out a small giggle before yawning and reaching over to turn off the bedside lamp.

She snuggled back into bed next to Caballeron, and drifted off to sleep...