"Are you sure you want me to do this? I mean, seriously. Really, really, sure?" Anon fidgeted, unable to find a place to put his hands. Before him, a tall, regal pony sat on her haunches, staring up at him. She held a riding crop in her mouth, somehow appearing stern and powerful in spite of her submissive posture and innocent eyes. She placed it gently on the bed before her.

"Yes, Anon. I understand that you are... hesitant, but you asked me if there was anything out of the ordinary you wanted us to try next time we were intimate. I believe your exact words were..." Her muzzle twitched into a playful grin. "The 'freakiest thing I could think of?' Well, here we are."

Since his arrival in Equestria last year under the newly founded Earth Equestria Exchange Program, Princess Celestia had taken Anon under her wing. As he grew more and more comfortable with life in this new world, their relationship had turned from a scholarly one into a romantic one, thanks to one incredibly brave first date request. The two had become closer and closer in the last several months. As a bonus, a formal courtship between the Equestrian leader and the first human ambassador was certainly a good public relations move for their worlds' new political alliance. On Anon's arrival, he never could have imagined feeling the way he did about a non-human, but amazingly, here they were, almost a year later.

Despite his apprehension, he felt a familiar arousal at her form. He had never pictured the strong, elegant ruler before him asking to be... dominated. Trained. But her lithe, powerful form and stately aura created an intriguing contrast with her current position. Celestia rested on her haunches on top of the sheets, bowing her head slightly. Her large eyes stared up at Anon like a dog expecting punishment from her master. Hell, she appeared downright cute, a true accomplishment for the normally strong, proud mare. Around her were arrayed a collection of items - sex toys, a collar, several small chocolates, and most intriguing of all, a riding crop, once again clenched in her mouth.

"I'm ready.... master."

His cock began to rise at that. Who knew something like this could be so... interesting? Since their relationship had turned intimate, she had always been his equal, or better, in the bedroom. He approached her slowly. His hand went to its familiar place on Celestia's long neck as a cool evening breeze blew in through the open window. He could smell the blooming flowers on the castle grounds, even from in here. Her soft white coat brushed against his fingertips, before they moved into her gently flowing mane. Anon always loved watching it. She leaned into his touch and closed her eyes softly. She began to purr, a soft hum coming from deep in her chest. It was a sound she always made when he touched her like this. This, at least, was comfortable to him. Anon chewed his lip hesitantly, but she was as enthusiastic and receptive as ever. It put Anon at ease, and soon he had removed his shirt and begun to unbuckle his pants. They moved closer together.

The two kissed. Their eyes closed. Celestia nuzzled against him as he kissed down her neck. Her forehooves wrapped around his lower back, and he stroked her horn and mane. Anon moved his face back up to meet hers, and they kissed again, more passionately this time. Their lips met and pushed into each other, and soon her tongue was exploring inside his mouth. They rolled, groping and kissing, across the soft satin sheets. Sunlight filtered in through the chamber's window, illuminating the smooth stone walls, the stately four-post bed, and Celestia herself.

Then, he was on top of her. Celestia's legs splayed out in the air, and Anon slowly moved his hands down her belly, between her flanks. Wetness stuck to his fingers as he drew them lightly across her entrance. She gasped. His heart began to beat harder in his chest. You know what?, he thought to himself, I'm doing this. It'll be fun. An idea struck him.

"Lay down."

The harsh, forceful tone of command in Anon's voice surprised him, but not as much as it seemed to surprise his ruler. She instinctively began to comply... but then stopped. "No." She grinned mischievously.

Anger flared up in him, fueling his arousal. "What did you say?"

"No." Her grin grew wider.

Anon reached for the first thing he found - the riding crop, and struck. The blow landed on her muzzle - not at all hard, but apparently enough to shock the both of them. He fumbled and almost dropped the riding crop. For a moment, Anon feared her reprisal, but then, incredibly, her expression changed to one of submission.
"Yes, master." Her silky, regal voice took on a fascinating inflection of submission. Her tone and downcast eyes sent Anon's cock twitching, and her lying down on her side made his jaw drop for a moment. He slid off his boxers, his erect cock staring straight into her face.

"What do you want me to do?" Her rear was positioned towards him, her tail lifted slightly. He knew what she wanted... but they could both wait for a little while for that. He wanted to make this last.
"Give me your head." She complied quickly, looking up at him with puppy dog eyes as he slipped a red nylon collar attached to a leash around his Princess's neck. Anon felt her heart rate quicken. She closed her eyes in pleasure.
"Good girl." He fed her a chocolate, and she took it gratefully. She chewed, swallowed, and licked her lips, rolling over on her back, legs bent in the air. She looked at him silkily through half-lidded eyes. She slowly rolled back over onto her belly, legs curled beneath her. Anon brought his member to her mouth and she gently took it, her lips parting to accept it. Her long tongue lapped up and down, and he put a hand on her long horn for support. He could see a faint trail of wetness appear to run down from her nethers. He moaned. Suddenly, her teeth scraped him painfully, and he lashed out.

"No!" he yelled, pulling up on her leash. Her head jerked up painfully.
"I'm sorry, master!" Her wide, almost teary, eyes begged him to let her continue, and he quickly relented. Her pace increased, and her arousal became more and more clear. He kept tight control of her leash as she sucked and licked, finally taking his entire cock into her mouth. He could feel his first orgasm approaching, and her pace increased once more. Anon could feel that familiar tingling warmth spreading through his loins. His climax was coming, soon. She fell into a steady rhythm - up, with her tongue brushing against his cock from base to tip, and down, taking it as far as she could. Her half-lidded eyes staring up at him was what finally pushed him over the edge. An intense wave of pleasure washed over him as he released inside her mouth. Celestia slowed her pace as he finished, and anon’s pleasure relaxed its hold on him. She stared straight into his eyes submissively as she swallowed his cum down to the last drop, and finally, he pulled back, still completely hard and ready to explore further. He could tell she was begging to take him. He looked down at her, some cum still clinging to the soft white fur of her muzzle. It hung in ropey tendrils of milky white off her nose and mouth. He was still panting, feeling at once relaxed and ready for more. The musky scent of sex hung in the air. She licked her lips, tasting the last remnants of her lover’s orgasm, and they both smiled.

"Good girl. Now, turn around." She backed up a bit, her half-lidded eyes never leaving his.

"Present yourself to me."

Celestia smiled, this time only with genuine gratitude. "Thank you... sir." Anon smiled at that himself. He leaned into her, and hey shared a chocolate and kissed. "I'm glad you talked me into this," he whispered, breaking character for just a moment.
"Me too." She giggled. Celestia lay on her side once more, this time positioning herself with her rear end right in front of Anon's kneeling form. She looked back at him out of the corner of her eye.

But Anon's attention was fixated somewhere else. Her strong, stately flanks sat before him on the bed, and he let his eye trace their curves, down to her long, crossed legs, down to her hooves, resting atop one another. But her tail, raised and pushed to the side, gave him a perfect view of what he really wanted.

Celestia's royal pussy lay before him. Normally hardly noticeable, she was now almost fully aroused, and it showed. Her lips swelled up, spreading apart and giving Anon a gorgeous view. Her soft, pink opening was practically overflowing with her juices. Her clitoris was enlarged and glistening, and he could even make out the subtle twitching that told him beyond a doubt that she was ready for him.

But not yet. Anon began took her leash in hand and began kissing and nipping up and down her flanks, down to her legs. Celestia let out a high-pitched moan as he reached her soft hooves, and she began to writhe and stretch.
"Stay!" he commanded. Holy shit, who would have thought I had it in me?, he thought. He yanked on her leash swiftly and smacked her flank with the riding crop. The harsh *Fwwhip!* of the blow turned him on even more. She whimpered softly. Satisfied, Anon resumed kissing her flanks and began to move towards her pussy. He teased her, licking and kissing all around her entrance, denying her the pleasure of direct contact. Suddenly, his tongue touched her lips and he licked, long and hard, up her slit, barely grazing her clitoris. It was too much for her, and she once more began to tremble and moan loudly, but he let it go. He licked her lips up and down, teasing her clit more and more, before finally putting his tongue fully inside her. Celestia pressed her rear into his face and whimpered harder, and Anon pulled down sharply on her leash. "I'm sorry!" she cried. Anon rose up and positioned himself at her entrance. He could feel the heat.

"Are you going to be a good girl, Celestia?"

"Yes! Yes, I will!"

"You'll do what I say?"

"Yes, I will!" She was panting now.

"Yes, what?" He snapped her head up with the leash and smacked her flank hard with the riding crop. Another wonder Fwwhip! rang out.
"Yes, master!"

Anon smiled. "Good." He pressed the head of his member against her soft, wet pussy. The trembling mare visibly struggled not to push back against him instantly. "Oh, very good girl, your highness."

Anon rewarded her by slowly inching his cock inside her. He could feel the tingle of her wetness as the head of his member pushed past her lips and into her soft lips. She gripped his cock, almost seeming to pull him in subconsciously. Her eyes were once again closed in pleasure as he slipped inside her warm, wet pussy. As he hilted himself into her, she finally pushed her strong flanks back into Anon's hips and moaned with pleasure. He pulled out, one hand in her soft mane, the other holding her leash, and pushed himself in again. And again, and again. He varied his rhythm in time to her signals - her breathing, her movements against him, the hardly-noticeable way she spread her legs lower and lower. . Sometimes, it was difficult to keep up the pace exactly where he knew she liked it, but he persevered. The sun was noticeably lower in the sky, visible through the window when he felt her speed up. Soon, she began to buck against him more and more. She lowered her forelegs and looked back submissively. It struck him once more how amazing it was that the tall, powerful pony could look so innocent, so cute, so seductive. But this time, there was no confusion or hesitance - only lust. Her submissiveness turned him on more than anything, now, and he began to feel another orgasm approaching. Another tingling, warm sensation spread throughout him, far more powerful this time. He closed his eyes involuntarily. Anon felt it building, closer and closer, with every thrust.

She was showing the familiar signs as well. Her long, powerful white legs spread apart, and her mouth opened, eyes still closed. She began to buck her flanks into him in time with his thrusts, and he could feel her begin to shake under him. Celestia's regal, pink pussy was wetter than it ever had been, and he knew her own climax was approaching too. If he made this work, it would be the first time they had ever came simultaneously. The thought of seeing the princess's orgasm almost sent him overboard, but he held back. Anon pulled back on the leash and Celestia let out something halfway between a whinny and a moan, and he knew it was time.

The royal mare shook, twitched, and convulsed underneath him as he came, shooting jets of cum deep inside her. Waves of pleasure rolled over him. Celestia's own orgasm lasted even longer than Anon's, and she was still trembling when he pulled out of her. His cum dripped out of her, clinging to her fur, and she collapsed on the bed with a sigh. Then they looked at each other, and smiled. Anon held her as she panted and nuzzled his neck.

"We need to do that again next time."

Author's Note

Updated and improved with some generous help from some critics. Gonna work on part 2 soon-ish. Maybe Celestia can be in charge this time? ;)