How Cherry Blossomed

As morning dawned and birds began to sing outside her window, Cherry Jubilee drifted into wakefulness. She smiled and snuggled herself back against the vast, powerful bulk of her coltfriend and stud. Feeling a pleasant ache in her marehood, she recalled that John had roused himself to her the middle of the night, overwhelmed by some lustful dream. He’d manhandled her willing body upon his massive cock and bounced her up and down on it for a good 15 minutes, taking her to one screaming peak after another before erupting with a fountain of cream that flooded her womb.

“Oh, John, that was incredible...” Cherry had moaned when he finally let up, stroking her coltfriend’s hairy chest as his grip on her flank loosened. “Why, we’ve coupled countless times, but I never knew you to be such a beast!”

“Sorry if I woke you, Miss Jubilee,” John had mumbled, already shifting beneath the blankets and swiftly falling asleep once more.

Now the tables had turned, for it was Cherry’s turn to enjoy the pleasures of John’s slumbering body. She gently reached beneath the sheets and gripped his fluid smeared cock, which rested in his usual state of half-readiness, like a carnal sentry listening for the cry of a mare in need. John quickly stiffened beneath the touch of her experienced hoof, and Cherry leaned into his ear and whispered the magical words that every stallion longs to hear from his lover...

“Today is the first of the month, John. You owe me another 400 bits.”

John grunted with slow wakefulness and reached for Cherry’s cum oozing marehood, repaying the soft pleasures Cherry was bringing him with a thrusting finger. After some minutes of loving kisses and mutual fondling he felt awake enough to speak. “I suppose I do,” he agreed with a yawn. “But I’ve been thinking, and I’d like to propose some new terms for our deal, in a way that’ll be pleasing to both of us.”

Cherry smiled as John’s thick thumb strummed her winking clit. She did love a good business negotiation! After all, John had saved her over 1,000 bits so far, just by convincing mares to take his cock in lieu of the usual payments or bribes. Zecora, Redheart, Mayor Mare... oddly enough, even Octavia seemed to be in a better mood these days. With all that her coltfriend had done for her, Cherry was happy to offer a little flexibility on the price of her love... she might even go down to 375 bits!

“See, it all seems a mite inefficient,” John explained. “I’m about to go off and work all day at the mill, and it ain’t easy work. I turn over my pay packet to you so I can fuck your girls, and that money goes right back out as them same girls’ salaries. Meantime you’re rushing around cooking and cleaning all day, when you ought to be focusing on promotion.”

John grinned. “The way I see it, there ain’t no reason why the Cherry Hill Ranch couldn’t be famous all round Equestria — and I mean bigger and more successful than Sweet Apple Acres.”

Cherry offered a thin smile to this ambitious idea. It was cute that her gentle lunkhead believed he knew how a brothel ought to be run, solely because he was the most effective marefucker Equestria had ever seen. Yet such thoughts had to be nipped while still in the bud. Cherry’s coltfriends inevitably seemed drawn to the idea of taking over the Cherry Hill Ranch and reducing her to a well dressed and well fucked figurehead. Yet even if there were a stallion with the business sense to run such an intrinsically feminine concern, it was not as if Cherry tended to attract the brainy type!

“John, why are you so concerned with the way I run my business?” Cherry asked the surprising pushy human. She lowered her muzzle to the tastiest part of his delicious body, tasting their mixed cum on the salty, weeping flare of his satisfying cock. “For you, the proposition ought to be quite simple: your bits go in, and our skirts go up.”

“That’s what I’m saying, ma’am.” John ran his fingers through Cherry’s mane as she treated him to his usual morning blowjob — on the house! “Simple’s how it started, but we made it all complicated, by bringing in matters of the heart. Like it or not, I’ve become a part of your business. Now, why don’t we get married, and take things back to simple again?”

“M-married?” Cherry’s tongue abruptly stopped moving across the head of John’s cock. This was not where she had thought this conversation was going!

“I reckon right now, most of my pay goes into your safe anyhow.” John smiled wryly. “Or to barrels of cider, or replacing Miss Muffins’ bed frame, or any of the dozen other expenses you’ve convinced me to pay with one of your heavenly smiles.”

“I do believe I gave you more than a smile for that new bed frame, John. You had no complaints at the time, as I recall.”

John blushed vividly. “B-be that as it may, the costs do add up, and at the end of the month I find myself with hardly a bit to my name. I reckon I’m in so deep that I might as well give you all of my money from now on, and get a fine wife into the bargain. Now, what do you say?”

Cherry raised her mouth from John’s cock and looked him in the eye. She bit her lip and set her hoof back on the human’s arm, her mind whirling and her heart sinking. “John, I am beyond flattered by your lovely offer, but i-it would be better if we kept our relationship as it is.”

“So you’d rather be my whorse than my wife?” For the first time Cherry Jubilee heard genuine anger and pain in John’s voice.

Cherry inhaled slowly, fighting back the tears. “It ain’t a matter of what I’d rather, John. Circumstances are such that I cain’t accept your generous offer.”

“Now, what the hell kind of ‘circumstances’ is more important than what’s in our hearts? Damnit, Cherry, I love you!”

Cherry’s heart was stabbed as she heard the most beautiful words at the worst possible time. Oh, how she wished she could go back to the way things were just moments ago! That middle ground between whorse and wife, the scrap of land labelled “marefriend,” was a paradise island where Cherry had just spent the happiest weeks of her life. That peaceable kingdom had suddenly vanished, sinking beneath the waves of John’s sudden proposal and her quick rejection.

Cherry steeled herself for the difficulty of what she had to do. “John, I will expect your 400 bits in instalments, and we will speak about this no more,” she insisted. “Your good looks and your kindly ways have made me careless, and I fear I allowed myself to fantasize beyond the bounds of my station in life. I am a courtesan, and you my generous patron. If this arrangement is not satisfactory to you, I am certain Sweet Apple Acres will take you back as a customer.”

John sighed deeply. “Well, I was going to kiss my fiancée and dream of our wedding, but if you’re nothing more to me than a whorse, I reckon I’ll spend the morning fucking your plothole open instead.”

“O-of course, John. Whatever you think is right.” Cherry rolled over on her tummy so John wouldn’t see the tears fall from her eyes. “You’ve paid to drain your balls into any convenient hole, and this whorse will see that you get your money’s worth.”

The morning ass fucking was fierce and angry. John forced the maregasms from Cherry’s body rather than simply inviting them. His hips bashed against her wobbling plot over and over as he thrust atop her, his meat stretching her to the utmost limit. His sweet, loving, innocent dirty talk was replaced by dark mutterings and groans, and after bloating Cherry’s guts with his load, John did something he’d never dared before: he pulled out and presented her with his soiled stallionhood, fresh from the depths of her asshole.

“John, you just... it’s dirty!”

John only nodded. “Wouldn’t need you to clean it if it weren’t.”

“Y-yes, sir.” Of course, she obeyed him. She would do anything for this perfect cock. Anything, it seemed, but accept the love of the man who wielded it!

Yes, make me do nasty things... teach me I was wrong to love you... Cherry silently sobbed as she tenderly licked John’s meat. Even mixed with the heavenly taste of his sperm, the tang of her plot was an ultimate degradation, a slap in the face from her once kind suitor.

This way would be better for both of them, she thought. Cherry Jubilee was a whorse, and never would be anything more. She was destined to perform the filthy acts that proper ladies shied away from. Whenever respectable females denied their husbands, she was here to pick up the slack: with her asshole, with her mouth, with her tongue upon another mare’s clit.

For a whorse to dream of her own life of love and passion was ludicrous. Cherry’s place was right here, in a bed that stank of sex, licking the taste of her own ass from a huge prick until it shined and glistened, clean as a whistle.

To make things worse, John didn’t even bother to stroke himself off and spew a second load all over Cherry’s face. He pulled up his trousers without even letting Cherry move her tongue further back, and clean the night’s sweat from his ass! All that musk, going to waste!

“Serves me right, falling in love with a damned whorse...” John muttered as he fastened his belt. He wiped a powerful hand across his tear filled eyes as he departed Cherry’s bedroom, heading away to his job at the mill.

Once the door closed behind him, Cherry Jubilee hid her head beneath a frilly pillow and bawled her eyes out. Long ago, she’d promised herself to the zebra soldier Zorago, and a lifetime of loneliness had been the result. Now, once again, an exotic stallion had loved her, wooed her, and asked her to marry. Why couldn’t she say yes to John?

“It’s too late for me!” she wailed into her pillow. But John didn’t think it was too late.

“I’m old, and fat, and ugly!” Again, the human seemed to disagree, hungrily worshipping her mature body long into the night.

“He’s from another world! He’s too different! We could never have foals together!” But rumours from Canterlot, and happy news from the Mayor’s office, said otherwise...

“I... I... I just cain’t!”

The truth was harsh, yet simple: Cherry Jubilee still held out an impossible hope that her first love would return and sweep her off her hooves. Across the years that intervened since their sudden parting, despite the utter impossibility of this fantasy and the sting of Captain Zorago’s betrayal, she still dreamed of her handsome zebra finding her, begging forgiveness, and carrying her to the chapel for the wedding day she no longer deserved.

There was still cause for such hope, ludicrous as the thought might be. Equestria was full of strange creatures, after all. Perhaps Captain Zorago had fallen victim to a cockatrice, and been turned to stone for decades. Now, finally restored to the body of the young stud she remembered, he searched Equestria for his lost love. Perhaps this very day was the day they would meet again. Yes, maybe today she’d hear the name she’d used with him, so long ago. She’d hear her lover’s deep and gentle voice say—

“Cherry Spice?”

Cherry blinked with confusion. Suddenly she stood at the front door to her brothel with a wet mop in her hooves. She had been sleeptrotting through her day, and it was now nearly noon. Derpy Hooves stood outside the door, here not as a whorse but as a mailmare on her rounds, holding a letter in her mouth. The lace of the fancy underthings from Cherry’s recent trip to Manehattan could be glimpsed through the sheer cotton fabric of the pegasus’ postal uniform.

“Eh? Derpy? What?” Cherry shook her head, trying to remember anything from the morning except for her endless agonies of self pity. “What did you just say?”

“I just wanted to know if you went by another name when you lived in Dodge Junction,” Derpy repeated. “Cherry Spice... does that ring a bell?”

Cherry Jubilee gasped at the name from her long buried past. “H-how did you know?”

“Appointed Rounds cleans out the dead letter office on the first of the month.” Derpy held out the letter with outstretched wing. “She mentioned a letter to Cherry Spice that keeps showing up. She always sends it back to Dodge Junction, but I remembered you used to live in Dodge Junction, and the name was close enough... so I thought I ought to check.”

Indeed, this letter had obviously been in transit for many years, travelling back and forth between Ponyville, Dodge Junction, and Zebrica, with occasional journeys to Appleloosa and the main post office in Canterlot. The name Cherry had used with Captain Zorago was nearly invisible beneath the layers of ink stamps and official stickers. “MOVED TO PONYVILLE” “NO SUCH EQUINE” “NOT FOUND IN ZEBRICA” “NO FORWARDING ADDRESS...” Yet beneath all of that, in rounded letters pressed onto the page by some strange zebra machinery, was written: Cherry Spice, 101 Tumbleweed Way, Dodge Junction, Equestria. That humble address was the location of Cherry’s first business, the original Cherry Hill Ranch.

With a trembling hoof Cherry Jubilee opened the envelope addressed to the smiling, confident young mare she’d been so long ago. Derpy looked on happily, enthusiastic about matching a long lost letter to its recipient, fully unaware of the turmoil she’d set off within her boss’ soul.

Within the envelope was an official notice written in Zebrican, which Cherry couldn’t understand. She would have to have Zecora translate it. Yet it was the other slip of paper which caught her attention immediately. This was a simple note written in his hoofwriting, a poem in Ponish jotted in Zorago’s elegant script upon a sheet of paper that had crinkled and stained by years of rough transport. The years seemed to fall away from Cherry Jubilee’s soul as she read her lover’s final message to her:

The night is deep outside my tent
My thoughts become now penitent
I think of you, my pony bride
Betrayed by stubborn zebra pride

My final dawn has near begun
My soul will set ere does the sun
For soon the battle cry will sound
And blood pour forth upon the ground

We could have grown old by the fire
Our hearts entwined, my one desire
But honour called, and so I fled
Dishonouring my love instead

Advice is all that I can give
My time draws short, but you still live
I beg of you to love again
Don’t tie your story to my end

Let go, my love. Be joyous, free
I ask but this: remember me.

“Cherry, are you OK?” Derpy asked.

Once again tears were pouring down Cherry Jubilee’s cheeks, and she didn’t know if they were tears of sadness or joy. “G-go to the mill!” she begged the stunned pegasus who’d just delivered the most horrible, most wondrous letter of her life. Zorago’s final words had released her from what felt like a lifelong curse. “F-find John... tell him... tell him yes, I WILL marry him!”

“D-did he ask you to marry him?” Derpy queried with puzzlement.

“DO AS I SAY!” Cherry Jubilee huffed.

“OK, geeze!” Derpy squawked.

As Derpy turned and launched herself away from the porch, Cherry galloped frantically up the stairs towards the bedroom where she’d just made the greatest mistake of her life. She wailed out a wordless cry, unleashing years of bottled up emotions, praying to every Princess there ever was that it wasn’t too late, that John still held some tender feeling in his heart for her. She tore open the door to her wardrobe and pulled out every single garment, searching for the lonesome wedding dress that had been present in her bedroom for the last 20 years, a silent witness to all of her struggles and sorrows.

“It’s been so long...” she whispered to the dress as she finally clutched the delicate white lace to her barrel. “But I promised you I’d wear you on my wedding day. Of all the promises I’ve made in my life, there’s one I can keep, at least.”

Through all these years, she believed she’d been saving this dress for Captain Zorago’s impossible return. Yet in John, Cherry Jubilee had found the fulfillment of every youthful promise and romantic notion she’d ever had. She’d finally found the stallion this dress was really meant for.

There was only one problem:

Cherry Jubilee no longer fit in her wedding dress.

She didn’t fit at all!

Her ass was 20 years wider and deeper than the slim mare who’d worn this dress. Her teats were far too big now, and hung out entirely. With the pudge that padded her barrel keeping her from doing up a single button, she looked like a delusional spinster swept away in some fantasy, imagining herself to be a young and blushing bride.

What could be done? This dress needed to be taken apart at the seams and sewn into an entirely new garment. She’d have to take it to Coco, unless... could Rarity help? No, no, no!

Coming from another pony, Cherry’s tale of love lost and found would captivate Rarity’s romantic heart, yet that unicorn bitch had never forgiven Cherry for sucking off her hot young dragon boytoy. (What was Cherry supposed to do, turn down a paying customer?) The mood from Applejack’s friend whenever they met on the street was polite, icy hatred. Rarity would never help Cherry Jubilee, even to give an old mare her long delayed happily-ever-after.

With a crash of breaking glass, Derpy suddenly corkscrewed through Cherry’s bedroom window, bouncing on her bed and slamming into the wall. “John says he’ll be at the town hall in 10 minutes!” came her muffled voice.

“A-are you OK?” Cherry asked, a worried hoof to her chest as Derpy slowly slid down the wall. Fortunately the clumsy pegasus instantly sprang up off the floor, uninjured, her eyes bouncing around wildly. “Mr. Broadbeam is going to be his best stallion! Oh my gosh, this is so exciting!”

“W-wait, 10 minutes? John wants to get married right now?” But of course he did, and so did Cherry! Oh, but what to do about the damned dress?

“He also says he hopes you didn’t take your potion this morning!” Derpy added with a wink.

Cherry couldn’t remember a thing about the emotional mess that had been the morning, but it was a dead certainty she’d forgotten to down her usual contraceptive draught. This was a good thing. Birth control and wedding nights did not go together, as far as Cherry Jubilee was concerned — and it seemed that John agreed!

“You’re my maid of honour!” Cherry made the split second decision as she struggled to pull a tight lacey sleeve over her chubby wither. “The other girls will be my bridesmaids! Go and fetch them while I... unnngh... put on this dress!”

“M-maybe the green dress would look better on you?” Derpy suggested, holding up a Coco Pommel design that Cherry had senselessly tossed upon the floor. “Do you see how it has... erm... enough space for your butt?”

Cherry Jubilee stomped a hoof so hard the mirror rattled on her vanity. “This is my wedding dress, and I aim to wear it for my wedding!” she insisted.

“Jeepers, I always knew she’d be a bride-Ursa Major...” Derpy muttered to herself. She tossed open the bedroom door and galloped downstairs, eager to awake her fellow whorses and tell them the good news.

With no time to waste, Cherry sucked in her tummy and forced herself into her wedding dress. She strategically ripped a slit down the back, let the skirts ride up her hips and left the buttons undone. She no longer care how she looked, or what others thought of her. She was doing all of this for the young mare who’d sucked hundreds of dicks to earn the money for the most beautiful dress in the shop. For the mare who’d worn that dress long into that horrible evening, as the shadows lengthened and the tears flowed.

In her years as a whorse, Cherry Jubilee had performed every degrading act the mind of pony could conceive of. Now she would willingly give up her final scraps of dignity, exposing and abasing herself in public, if it meant that poor mare would finally get her wedding day.

The reaction was more than she could have hoped for. John’s jaw dropped when he saw Cherry walk down the aisle, bursting out of the ancient garment. His cock thickened to a fat bar of iron in his work jeans, much to Mr. Broadbeam’s embarrassment. John could hardly keep his hands off of Cherry’s plush, bountiful body as he said the words she had waited half a lifetime to hear. This noble human promised to love Cherry, and cherish her, and show her every pleasure his own young body could muster, forever and ever.

And so it was, that in the end, Cherry Jubilee didn’t have to wear that dress for very long at all...