A Night to Remember

by The Camera Man

Rating: mature
Tags: Fancypants, Sex, My Little Pony: Friendship is Magic, Dark, Original Character
Length: 1777

Cherry Blossom is having the night of her life at the Grand Galloping Gala. Fancy Pants intends to make it a night to remember.

Cherry Blossom is having the night of her life at the Grand Galloping Gala. Fancy Pants intends to make it a night to remember.

Published 2015-05-31 17:20:02 UTC
Last updated 2015-05-31 17:20:02 UTC

Rule Number 2

Fancy Pants looked over the unconscious mare on his couch, and immediately checked to make sure the door was locked. That was Rule Number One, after all. Satisfied that the door was properly locked, and that there wasn't any chance of some hapless pony stumbling into his room, he walked back over to the unconscious Cherry Blossom.

She really was quite attractive. Bright red coat shining like a fire star, a mane of silken gold, and eyes like twin sapphires—both had a smattering of freckles underneath.

In other circumstances he could have easily seen himself taking her out on the town, seeing the sights, gradually working his way into her affections until this juvenescent mare would be all too happy to lift her tail for him. But as luck would have it, they’d met at the Gala. And that allowed him to be much more . . . direct in his affections.

But there were rules. And The Rules had to be obeyed. If you were a good pony, and you followed The Rules, then you wouldn’t get caught. It was just that simple. Only bad ponies didn't follow The Rules. Fancy Pants was not a bad pony.

Back at Cherry’s side, Fancy Pants lowered his head and put an ear to her mouth. Drowsy Tree nectar was a most remarkable drug, capable of rendering a pony dead to the world with only a few drops. It was virtually undetectable—tasteless, odorless, colorless. And for as long as Fancy had been using the nectar, it had always worked perfectly as intended.

But Rule Number One stated: take no chances. And so Fancy Pants made sure that Miss Cherry was breathing properly. And after he had insured that she was respiring normally, he gently put out a hoof and nudged her with it.

“Oh, Miss Cherry,” he said cordially. “I do believe that you've fallen asleep on my bed. Are you all right?”

The young mare was still.

Fancy Pants nudged her again, harder. “Miss Cherry Blossom, I do believe that you might have had a smidgen too much to drink. Miss Cherry?”

Nothing. Cherry Bloom was out like a light.

Fancy Pants smiled.

Gently, he began to undress her with his magic. Leaving the clothes on could result in damage to the clothing—or even worse--stains, that would of course lead to the owner of said clothing asking questions about how such things had come to pass. And such questions would not lead to pleasant answers.

He started with her stockings, gingerly folding each one before placing it on the floor, then he began on her dress; this proved much more difficult. Because she was a pegasus, he had to exercise extreme caution in pulling her wings from their slots without irritating them. Pegasus wings were very sensitive, after all. But Fancypants was very well-versed in the ways of getting a mare’s clothes off and in short order, she was naked before him.

He took a moment to take the sight of her in. Like most pegasus, she had a body made for speed rather than strength—lean and lithe from a lifetime of flying. She looked almost sculpted. Fancypants put a hoof on her flank, running it over her cutie mark. She had a very nice flank.

And now, she was all his. Pearls before the swine.

But first thing's first: The Rules had to be observed. Slowly, he lowered his head to her belly and touched her with the tip of his horn; there was a flash of blue light, and then silence.

An anti-pregnancy charm. The same charm that one could pay virtually any unicorn in any clinic or hospital across Equestria to perform. Quick, simple, and unquestionably effective.

At last, he could begin.

Fancypants could barely contain himself as he traced a line from her belly to her neck with his nose, taking in the softness of her coat, the smell of her perfume, the sound of her muted breathing. Then, he traces a line back down to her belly, and then lower, to her mons veneris, to the two nubs of flesh betwixt her legs. Her teats, soft and supple, just as beautiful as the rest of her, laying exposed and vulnerable. He lowered his head and takes one of her ripe teats into his mouth. Running his tongue over the nipple, sucking on her soft flesh, kneading it with his teeth; in seconds he feels it begin to harden from his attentions. He takes his hoof and begins to run it up and down her other teat, massaging it into hardness.

And then she moans.

Fancypants froze, like a thief that’s been spotted in the night leaving a crime scene. One of her succulent teats is still in his mouth--the tip of his tongue on her nipple. He waits for a beat, then a second, third, and smiles. "Oh my. Having a little fun are we? What a naughty mare you are, Miss Blossom."

Cherry Blossom’s slack face makes no reply however.

He wants to take her right then and there. Just roll her over and fuck her like a dog. But he doesn’t. He can’t. The longer the wait, the greater the weight, as his father always used to say. Delayed gratification is a lesson that he’s learned all too well. So he lowers his mouth to her other teat, and gently massages it with his tongue.

He’s hard now. Almost painfully hard. He could feel his cock pressing into his belly, reaching out to the soft fold of flesh between her legs. Fancypants wants to fuck her so badly. He’s almost shivering with the promise of release. His breathing is coming in ragged gasps now. He lowers his mouth and tastes her sex. Spreading the lips of her pussy with his tongue, his legs nearly collapse from need.

He has to come. He has to come now.

He pulls away from her crotch, and goes around to the front of the bed. Her mouth is slightly open. A single line of drool running down her chin. Fancypants licks his lips, and presses the tip of his cock to her mouth. Her lips are pliant, accepting. She wants his cock. Slowly, he slides the entire length of his shaft inside her mouth. She makes a muffled gagging noise, and tries to turn away, but Fancypants grabs onto her head with both hooves and thrusts. The feeling is amazing, her tongue rubbing against his cock, her spittle lubricating his cock. With every thrust he feels it coming on, inching closer and closer to the final . . . RELEASE!

With a great moan, Fancypants’s cock starts to throb, pulsing with the bound tension of his seed, and he feels it pumping into her mouth. He pulls her head tighter to his crotch, not wanting any of it to escape. When he’s done, he pulls himself out of her mouth, and thin trail of white stretches from his cock to her open mouth. He smiles and pulls her mouth open wider, it’s filled with his cum, like an offwhite lake in her mouth. He closes her mouth and tilts her head back. She makes a slight gagging noise again, and then starts to swallow. It’s a natural reflex.

Fancypants waits until she stops swallowing, and makes his way to the other side of the bed. Gingerly, he rolls her over onto her stomach. His cock is spent but he can already feel it growing to full hardness again.

It’s time. Time for the mane event.

Fancypants uses his magic to lift her tail. He raises himself onto his hind legs and places a forehoof on each flank. He uses his magic to grab line his cock up with her entrance. It’s still slick with spittle and his own seamen.

Slowly, he inserts the head of his cock into her pussy. It takes every ounce of willpower he has not to ram his full length into her. But he has to be sure, sure that she’s not—

A Virgin! He stops dead. There’s no mistaking what he’s feeling. There, rubbing up against his cock head, is the thin, membranous resistance of a hymen. Cherry Blossom is a virgin. His is the first cock that has ever been in her pussy. And no matter how long she lives, or how many other stallions she fucks, his will have always been the first.

The dam breaks.

Fancypants can no longer contain himself. With a roar, he sheaths his slick cock into her pussy fully, skewing her hymen more with each successive thrust. He’s faintly aware that she’s mewling slightly, probably from the pain, but he doesn’t care. Her pussy was so tight, it felt like a vice grip upon his cock. He can feeling it coming on him already, he comes into her, filling her virgin pussy with his cum.

He falls on top of her, and heaves a sigh. His cock is still inside of her, still throbbing. Still filling her with his cum. Fancypants almost wishes that he hadn't cast the contraceptive spell on her. The idea of not only taking this mare’s virginity but also impregnating her with his child was a strangely tantalizing one. He imagined it: his virile sperm making their way into her fertile womb. Her eggs, laying there defenseless as his sperm swarmed over them. Penetrating them. Filling her womb with his child.

He was hard again.

Fancypants was a little surprised to feel his cock once again growing hard with the thoughts of impregnating this delicate little mare. But not unpleasantly so. He was growing quite virile in his old age, he thought to himself with a smile.

Fancypants pulled his cock out of Cherry’s newly deflowered pussy, it was dripping in her fluids, his semen, and her blood.

It was a shame that he wouldn’t be able to enjoy her more, but there were rules. And the rules had to be observed.

Rule Number 1: Take No Chances.

Rule Number 2: Leave No Trace.

So, with a sigh, Fancypants pulled out his kerchief and began the slow process of cleaning up the mess. After he wiped the assorted fluids from Cherry’s mouth and pussy, he got into the shower, and cleaned himself off. After he was clean, he redressed Cherry and returned her to her room.

Perhaps in the morning he would check on her, maybe ask her out to breakfast or dinner. Wine her and dine her and maybe enjoy her again. As long as he obeyed the Rules, everything would be all right.

Author's Note

Dedicated to the great Bill Cosby.