Rarity's Generous Plan

Through the pane glass of the picture window, five distant figures moved off towards the setting sun, pacing down the road together. Laughing. Joking. Playing. Not a care in the world as they soaked up the late summer sun and pranced in the warm breeze.
And here Rarity was stuck sewing.

It wasn't fair.

Not that she cared about herself, of course. Not that she would be so petty as to feel jealousy for her carefree friends while she slaved over a sewing machine to create wearable masterpieces of artistic splendor, each a unique product of incomprehensible fashion genius custom-tailored to the very ungrateful foals now trotting happily down the road without sparing her a single thought. No, this had nothing to do with self-pity, or jealousy. Because Rarity wasn't the type to feel sorry for herself.
She was only worried about her friends. Magnanimous as she was, knowing only generosity and consideration for others, all she could think as she ran the golden swatches of fabric repeatedly through the machine was that they were truly the unfortunate ones.

How pitiable they must be, to think so little of their most helpful and generous friend. Without judging, without hate, she felt sorry for them. They weren't the well-rounded friends they thought they were. They were... deficient. Lacking. Naive. Untrained. She couldn't be mad at them, not as warmhearted as she was. She only wanted to make them see. To enlighten them.

They needed to be brought into adulthood.

But how could she do that? How could she make them see how much more mature she was, emotionally? How could they know the true depths of the pool of friendship, like she did, if they still cantered about in the shallow end? Pinkie was throwing parties like a little foal and Twilight barely knew what friends were.

They didn't know the wholeness of the world, the other aspects of friendship. They couldn't see the hardships, the trials of friendship. They couldn't understand the loss, the love. They had never labored as Rarity did, with her complex relationships, her mature and sophisticated interactions. Could a brutish and uncultured pony like Applejack even know what it was like to long for the refined touch of a Prince Blueblood, or show him the perfumed air of a boudoir? Could they even comprehend...

That was it.
That was the key.

Their childish notion of what friendship really was, which stunted them in their empathy for the selfless white unicorn, had to be broken down. It had to be smelted down and reforged into something new. Something better. Something more... full. If they knew the depth and breadth of friendship, as she did, they wouldn't be so childishly dismissive and callously cruel to someone only trying to help them. They just needed their virgin minds expanded. Rarity had experienced the sights and sounds of the world, the tastes of more complex friendship, of relationships far deeper, smokier, more cultured. She was no naive filly, but a grown mare. She had known the touch of a wild stallion, and it was the enlightenment of adulthood that came with it.

That was it.
That was the key to helping them.

They had to know the true depths of friendship. The surge of love. The touch of a stallion. The passion of lovemaking.
If she wanted to help her friends, she was going to have to get them all to leave their virginities behind.

The elegant, benevolent, unappreciated white unicorn tossed her fabrics aside and replaced them with a small black notebook. Flipping it open, she produced a quill from her desk and held it high, her regal horn glowing with spectacular energy as it manipulated the ink across the page in her swirly script.
It was time to plan.

And a brilliant plan it was, really. It's amazing it hadn't occurred to her sooner. Rarity knew that her friends were all... inexperienced. Of the entire group, she was the only one who had truly graduated to adulthood, who had given her innocence to a wild stallion in a steamy boudoir, amid the lace and silk of the sensual sheets. But the others were all still virgins. And they couldn't possibly explore the depth of emotion in the world without having their own depths explored. So it was up to their very best friend, their generous benefactor, their guardian angel, to properly see to their education.

Of course, there might be complications. They might not understand, at first, the generosity of these efforts. They might not realize just how helpful and pivotal she would be in their maturation, their transition to true adulthood. But if you spare the rod, you spoil the child. Tough love was still love. And anyway, they'd surely thank her in time. Once they came around, they'd thank her. And then they'd all apologize for treating her so brutishly. For ignoring her.
For going off to play while she slaved over their fashion-ignorant whims.
And then they'd all go off to play together, the very best of friends once more.

So she could not emphasize enough how important this plan was.

Who would be first? She had to orchestrate their breaking-in carefully. Simply getting them into a situation where a stallion could bring them to adulthood was not enough. She wanted to make sure they were in no danger, of course. Not to be physically harmed. She wanted to make sure the colts she incorporated into her scheme took proper... precautions. She wanted to teach a lesson, but a careful hoof was required.
And of course, none of them could know she was behind it. It simply wouldn't do to show her cards too early in the game.

Handling each of her friends would be a delicate matter. She began to write notes, brainstorming furiously as the quill scratched brilliance across the pages of her notebook.
Twilight Sparkle. Bookish. Ivory tower. Naive. She would be an easy target. For all her book smarts she would never see a setup coming. Who would be the colt for the job? It wouldn't matter. Spike? No, he might back out. Might try to get her out of it in some misguided attempt at "helping" her. Better to go for a clueless colt. Even better that they could be insinuated under the guise of a student seeking tutoring. Who was that slow pony with the big ears? She wrote herself a note.
Applejack. A challenge. But so eager to help anyone in need she could be manipulated. A girl as tough as her would need a... sizable man to break her in properly.
Fluttershy. Almost too easy. She'd need a light touch. But firm. Rarity might have to intervene directly. Don't want to hurt her. Maybe find one of the less well-endowed colts in town to handle her.
Pinkie Pie. A stifled laugh. It would be like a game. If she told her it was a game, she'd probably tie HERSELF up and save Rarity the trouble. She needs a party she won't forget.
Rainbow Dash.

...Rainbow Dash.
A girl that stubborn, that strong, would need some real fancy maneuvering to get to. But it would be two birds with one stone: bringing her so helpfully into adulthood while also doing her the favor of dispelling her misguided notions of homosexuality. What better way to show her the pleasure of men than to have her experience it directly?

And who better to make her into a woman than the very men she respected most? It would be glorious. Lovely. Rainbow Dash being united in sexual awakening with her heroes.

That would be her pièce de résistance.

She continued writing. Furiously flipping page after page as her plot began to unfold on the paper before her. Her mind raced and her heart quickened, as the realization washed over her that such a plan truly was within her grasp. She had the wiles to get the stallions she needed to go along with it, as if they needed any more motivation than the virginities of these tender young fillies she would be giving away. She had the connections to get what she needed. She knew the right people. She had the right access. She briefly wondered if Celestia's guard could be bribed to turn a blind eye. For an even briefer moment, she considered getting them in on the fun directly.

Before long, Rarity had it almost all prepared. She knew she would have to act quick, to make sure her plans for her friends weren't spoiled. They wouldn't know it was generous Rarity all along who would be responsible for their blossoming into women. Not until the very end.
When it was too late.

Now, she nodded. Now she merely had to make one more big decision. Brought back to where she had started.
Who would be first?