It had taken much effort for Luna to convince the others to never speak of what had happened in the game room again. Gregory was willing, but Maud proved to be a shrewd negotiator, requesting a number of tax reforms which, as Luna pointed out, would directly benefit Pie Industries. While Gregory insisted that Maud was taking things too far, that blackmailing royalty was a serious offense that could lead to serious consequences, Maud merely asked where she could find Queen Celestia this time of day and Luna came up with all manner of rationalizations that they were simply engaging in private negotiations. The trio parted on seemingly good terms, with Luna rushing back to her game room to relieve her anxiety.

“I can’t believe you just did that,” Gregory said as he lay on his bed, staring at Maud. What she’d done, and how calmly she’d done it, scared him. However, as he thought more about it, he realized that it wasn’t actually fear he was feeling, but excitement.

Maud had been arranging the crystals on the windowsill according to hardness; he’d started a small collection since their first trip to the crystal shop; when she caught a glance of the way her stallion was staring at her. She rolled her rump slightly; drawing his attention to where she felt it belonged as she pretended not to notice.

“You seem to have trouble believing a lot of things I do,” she said casually as she inspected a citrine, recalling that Gregory had once said it was his favorite. “Maybe the issue isn’t with me, but your belief system?”

“I believe you’re purposefully shaking that flank of yours to entice me,” he growled. “How does that sound?”

“An interesting theory,” Maud said dispassionately as she set down the stone and turned to face him. “Do you have any evidence?”

“Were you shaking your butt at me a second ago?”

“Yes.”

“That’s my evidence,” he smirked.

“Compelling,” Maud said as she strode up to the bed. “But I’m afraid we can’t follow through until you can prove beyond a reasonable doubt.” She stopped with her face less than an inch from his.

Already able to feel the heat from her muzzle, Gregory leaned closer. “So, hypothetically, how would a guy go about removing all doubt that his sexy mare was shaking her sexy flank in his face?”

“Well…” Maud averted her gaze, looking strangely guilty. “There is something I’ve been meaning to ask.”

Gregory pulled back, frowning in confusion.

Not saying a word, Maud walked over to the book shelf, retrieved a tome, and brought it back for Gregory’s inspection.

The book was not one he recognized as his. Reasoning that Maud must have brought it over at some point, he noted the arcane symbols on the cover indicated that it was a spell book; though not of a kind he was familiar with. It was definitely not something Peach had ever shown him. At Maud’s urging, he noted the blue bookmark and turned to the desired page. His jaw fell as his eyes fell upon the title at the top of the page.

Fun Times with Magic and Anal Sex

“Sorry,” Maud apologized, staring at the ground and rubbing a hoof against her leg in embarrassment.

Gregory opened his mouth to speak, but decided to remain silent and let Maud explain herself.

“I found this book a while ago and… maybe… possibly left it here in the hopes you’d notice and… well…” she trailed off, unable to complete her thought.

“That I’d take the hint and practice the,” he coughed, glancing back at the page, “spells?” Maud was clearly having a hard time and he knew, despite her earlier boldness with Luna, that he needed to be gentle with her feelings. He looked down at the book, skimming the subheadings. Unsurprisingly, pretty much everything was related to butt play, from cleaning, to lubrication, to the various applications of magical pressure that spilled over into the next few pages. “Maud…”

“I understand if you don’t want to.” She was still unable to look him in the eye. “And I’m not saying I haven’t loved everything you’ve done up until now! Especially the stuff you do with your mouth,” she added quietly. “It’s just that…”

“You… want to try something… new?” Gregory asked carefully.

“It’s not new,” Maud admitted. “I’ve always liked doing it donkey style.”

Gregory’s brow furrowed in puzzlement until it hit him. Donkey equals ass. Duh.

“Whenever I went into heat, I would always use this special two pronged cooler. I, uh, still own it.”

“Why didn’t you tell me?” At her questioning look, Gregory shook his head. “Not the cooler. I mean,” he held up the book, “this. Why didn’t you just ask me, well, directly?”

Maud lowered her head. “Because I’m a mare. Its… embarrassing to want to do it like a stallion.”

“Wow,” Gregory deadpanned. “That may be the silliest thing I’ve ever heard, and I’ve met your sister.”

Maud looked up, her ears perked in interest.

“That is, not that you’re silly, but…” Gregory went back to reading over the book before he stuck his hoof in his mouth again. “I guess arbitrary taboos on sex are a burden across all dimensions, huh?”

“It… um…” Maud continued, a bit more optimistic. “It’s also considered disrespectful for a mare to do that to a stallion. It’s like saying that you’re… just a toy and that your, well, seed isn’t good enough for foals.”

“Oh,” Gregory nodded, finding this explanation slightly less arbitrary. “But you don’t see it like that, right?” He already knew the answer, but felt he needed to ask for her sake.

“Of course not!” Maud asserted. “You’re my stallion and I love every part of you.” Her face reddened when her mind caught up with her words.

“You just want to feel good,” Gregory said plainly. “And you’re asking because you care about how I feel.”

Maud gulped, sensing the tone of appreciation in her stallion’s voice. “So… you don’t mind that…”

“My sexy mare wants it in her sexy tail hole?” He finished with a sly smile. “Not one bit.”

Maud’s face turned beat red as she stared blankly at her stallion. She had always feared what might happen if stallions found out her fetish, which was regarded as highly taboo in the more conservative parts of Equestria. Of course she trusted Gregory not to do anything rash like kick her out of the herd. He loved her and she knew it. However, she had still braced herself to calm down his disgust and make amends by offering to do it any way he liked. But this…

“Which, um, which one did you want me to try first?” he asked, indicating the book.

Maud blinked, snapping back to reality. “Oh, uh, the first one.” She pointed at the top of the page just below the introductory explanation. “Cleaning,” she squeaked. “It’s the s-simplest, and a st-standard part of a-all…”

“I get it,” Gregory assured as he began reading in earnest.

Maud stood silently, grinding her thighs together in anxious anticipation as her stallion studied. The grinding only served to stoke the fires growing in her loins and she was overcome with the urge to do something. She left him on the bed and hurried to the bathroom where she retrieved a number of items they might need; toilet paper, lubricant, and herbal stimulants to name a few. Let none say that Maud was a mare who didn’t come prepared.

Peeking out of the bathroom to see her stallion was still distracted; a still anxious Maud decided to disrobe. Her frock was quickly removed and folded neatly. Looking at herself in the mirror, she grabbed a comb and started fiercely attacking her mane and tail, removing all traces of imperfection, which took less time than she’d hoped. She didn’t want to pressure Gregory by asking him to hurry. It would be criminal to be so rude after he was going to such trouble for her sake. However, her increasingly distraught mind was beginning to contemplate jumping him and forcing it inside, without lubricant, and just riding him the rest of the day and all night.

“Alright,” Gregory announced calmly. “Seems straight forward enough.”

Maud walked up towards him, set the supplies down on the floor, and angled her body so that he was facing her side and her rear was aimed at the open door to the bathroom. She wasn’t especially literate in magic symbols, but it still seemed courteous to help out in whatever way she could. “R-ready whenever you are.”

Gregory held his hoof in front of his face, as if trying to touch the spell as he read. “Alright,” he exhaled. “Here goes… something.” And he cast the spell.

Maud gasped and collapsed to the floor. The pressure inside her rectum was brief, but the feeling of being touched so intimately by magic was incredible. There was the slightest wet *plop* that came from the toilet. Maud exhaled, clenching her rear around the pressure her mind told her should still be there, but there was nothing. The spell had done its work, cleaning out her insides thoroughly and ensuring nothing would get terribly messy.

“Maud!” Gregory dropped the book, hopped from the bed, and rushed to her side. Seeing the way she shook made his heart sink and he rubbed his hoof against her mane.

Maud looked up and blinked at her stallion. “I’m… fine,” she grunted.

“You sure?” He surveyed her body anxiously for anything that seemed out of place. “I mean, you just-”

“It was your magic touch,” Maud exhaled contentedly. “Cliché as it may be, it was magical.”

Gregory chuckled giddily as he rested his cheek against hers. “You’re something else, you know.”

“I’ve had suspicions, but thanks for confirming,” Maud said flatly. While normally she’d be content to just rest and cuddle with her stallion, they had a mission to carry out and she wagged her flanks against him.

Gregory took the hint and stood, looking down at Maud questioningly. “So, um, how do we start?”

The earth pony did not speak as she lifted her rump high in the air, flagging her tail back as she kept her front half pressed against the carpet. “First, I’ll need a pillow.” Gregory nodded and promptly swiped one from the bed, setting it beneath Maud’s head. “Second, I’ve had plenty of success letting you explore on your own,” she said with a playful shake.

Purposefully, Gregory slipped off his pants before walking around behind Maud where he had to stop himself from drooling at the delectable sight. He’d seen her privates before, but now her anus was winking just like her pussy, inviting him in. He set a hoof on her rump, less than an inch away from her ponut as it winked all the faster.

Maud coughed, getting Gregory’s attention as she pointed at the supplies, particularly the lubricant. He moved to snatch it with his magic, only to return and find that Maud had reached behind and spread her left plot cheek back, presenting herself fully. “I don’t want you to miss,” she deadpanned, snorting cutely at her own joke.

“Should we, um, stretch you out first?” Gregory asked. “I don’t want to hurt you.”

“Don’t worry,” Maud groaned impatiently. “Pony bodies are really flexible, plus I’ve had a lot of practice back there. To be honest, you probably don’t even need the lube. I could have…” Maud paused, eyes widening in realization.

“Could have?”

“Could have just used my mouth,” she said with a sulk at the missed opportunity to fellate him.

“Next time,” Gregory chuckled lightly. Now more confident, he took another glance at the still opened book and nodded at the directions. Gregory hopped up onto Maud’s back, using her rump for support as she cooed in delight at the pressure of his weight atop her. Having long been out of his sheath, Gregory let his dick flop between Maud’s soft cheeks. He began humping up and down her crack, the slickness of her mare juices coating the underside of his cock as he did. Remembering the bottle of lubricant, he undid the cap and poured a generous helping onto his shaft.

Maud cooed as the cool liquid flowed around her ass, creating a wonderful contrast with the burning dick. She gave her rump an enticing shake as she fought the urge to clench around the length too soon. Unable to form words, Maud looked over her shoulder and gave a pleading squeak.

Gregory nodded. “Alright.” Positioning the tip of his penis against her winking ponut, Gregory leaned forward with a gentle push. He gasped sharply as Maud’s tail hole opened for him. It was tight, but he managed to slide in surprisingly smoothly. Guess she really did practice. He continued to slide in until he felt her dripping pussy against his balls.

Maud covered her muzzle to muffle a cry of joy. Her stallion was so amazingly gentle in how he’d entered. And now he was inside her forbidden hole, her mind unable to grasp anything apart from the feeling of warmth and fullness he was giving her. The way her insides churned and moved aside to make way for their guest was divine.

“I…” Gregory gasped, body quivering anxiously as he felt her anal walls grip around his shaft. “I’m going to s-start now.”

Maud peeked up from her hooves to find Gregory’s eyes trained on her. He was asking permission, and she nodded.

Gregory pulled out slowly, savoring the feeling of her anal walls clenching around him, but also the quiet moaning of his mare. When only the tip was left inside, Gregory slammed back in with as much force as he dared, earning louder moans from his mare.

“Harder,” she begged.

Gregory nodded, repeating the process of slowly exiting followed by a swift thrust inside. “Oh Maud!” he moaned amidst the wet sloppy sounds of their fucking. Without realizing, his horn had begun glowing as magical hands materialized around his fore hooves. His magical construct fingers gripped around her flanks, paying special attention to her cutie marks. At Maud’s growing cries of pleasure, Gregory intensified his thrusting.

“Harder!” Maud growled.

Gregory obeyed, growling with lust as his thighs slapped against her flanks. All notions of rhythm were lost as he pounded away wildly into her amazing ass. With one final thrust, Gregory bottomed out inside Maud and let out a triumphant howl.

Maud felt Gregory’s tip flare before he came inside her ass, filling her with his warm hot cum. She buried her face into the pillow, crying out in muffled ecstasy. It happened. It had finally happened. A real stallion had just cum in her anus, and she loved it. She’d also cum, her pussy spraying her juices all over Gregory’s balls and thighs.

As with their first time, Gregory collapsed onto Maud’s back. Though, to his credit, he managed to not fall asleep this time. Gripping weakly around her middle, Gregory looked up for a view of Maud’s face. Her face was obscured by the pillow as her body rose and fell with her breathing.

“You… did it…” Maud said softly.

“I did,” Gregory whispered back.

“It’s so warm inside me,” Maud moaned, clenching her butt around the flaccid cock.

A goofy grin spread across Gregory’s face. “Pleasure, m’lady.” He tilted his imaginary hat at her.

Dismounting slowly, Gregory elicited a final moan of delight from Maud as he extracted his cock from her ass. Her anus remained gaping only for a short while before closing up again, sealing its liquid treasure inside.

Maud eventually found her hooves again, though Gregory remained by her side in case she still had trouble. The gesture was unnecessary, as they both knew how strong she was, but she leaned on him regardless as he helped her to the bathroom. After flushing, they climbed into the tub and showered off their excess sweat. Maud insisted on using her mouth to clean Gregory’s cock, uncaring for his concerns that it might be dirty. As it turned out, the cleaning spell had worked perfectly, as indicated by her moans of pleasure.

“I p-probably should have mentioned this earlier,” Gregory said through gritted teeth as Maud worked. “B-but I’ve always h-had a b-bit of a-oh-butt fetish.”

Maud ceased her ministrations and climbed out from beneath Gregory, fixing him with a deadpan glare, causing Gregory to fidget nervously. “If that’s the case, I don’t suppose you’d mind tending your mare’s plot more regularly?”

Gregory grinned and kissed Maud’s nose. “If that’s what my mare likes, then that’s what she’ll get.”

Author's Notes:

Clop number 2 and good times ensue. These two open up a bit more and have a lot of fun in the process. Also, super sorry for the long delay. Will try to post more frequently, but I have other stories that take priority at the moment.