Heartmend's Bad Day

by thatonestupidpony

Lost Bets

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Pegasus were generally a very stubborn race, it was how things had always been. They were prone naturally to be competitive. This was where Heartmend had made an error that would change the rest of her afternoon. Heartmend had been lying on a cloud earlier when Thunderlane flew by, stopping a bit ahead of her, the other grey coated Pegasi turns towards her and calls, “Hey Heartmend, hows about a bet”

The stubborn coal colored pony looks at him, she makes a small snort like nose, as if to dismiss him. “Naw, I’m resting now” She tells him. He makes an upset face, and edges her on, “Aw come on Heartmend, just a small bet, come on, I’ll race you to that cloud and then back” he says, pointing a hoof at a cloud about 300 meters ahead of them. “Don’t be a killjoy” he insists.

The mare sighs, and stands up, stretching on the cloud where she stands. “Okay, what’s the bet” she asks a bit dismissively, she really didn’t care about this. The other pony thinks for a moment before speaking, “Looser has to do whatever the winner says” he states, and then as if for emphasis adds, “Anything they say”
Heartmend rolls her eyes at him, a bit annoyed, “Yeah, whatever lets fly, who’s gonna do the countdown?” Another Pegasus close by, a white mare, with a blue main and a grizzly voice agrees to do it, and she does, counting down from three…two…one.

And they were off, Heartmend wasn’t really trying her best, she was flying quickly, but not as fast as Thunderlane, who reaches the cloud first, stomping down on it and looking pleased with himself. “I won” he states, Heartmend doesn’t look terribly impressed, but she doesn’t seem to care too much. “What do I have to do?” she asks.
“Just meet me in Canterlot at sundown, by the donut shop, okay?”

Heartmend doesn’t understand why the message is so cryptic, but she nods, “Yeah, okay I’ll see you there” she states, twitching her ears back a bit. And so she goes back to town, but as soon as sundown rolls on by she’s in Canterlot. Thunderlane is there too, standing in front of something that looks like an old stockade, but more modern, made out of a shiny metal. “Okay, get in this, so we can start your half of the bet” he instructs.

She recognizes the object and her stomach sinks a bit, “What, but that’s for sex,” she says, frowning, “are you gonna have me flaunt my mare hood around Canterlot?” she asks, her voice loud, nearly yelling at the stallion.

The stallion simply chuckles and nods, and she looks mortified, but realizes that she did agree to do anything, which unfortunately meant she had to do this, especially because the white Pegasus from earlier had showed up, as if to verify the fulfillment of the payment of the bet.
The stubborn, coal coated Pegasus steps forward and steps into the stockade, resting her head through the head hole and her front legs where they go. Thunderlane secures her hind legs into rings that are tacked in the ground.

“You’re to stay here all night, free use for whomever comes by and wants to use you” Thunderlane chuckles. She’s mortified, but can’t say anything, she has nothing to say. Thunderlane himself doesn’t defile her, no, he just sits back and waits to watch Heartmend get fucked by whomever wants too.

The first pony that approaches is a member of the royal guard, he looks at the mare for a moment, as if he is going to comment about something being against the law, before he shrugs, and walks around to her back, “Well prostitution is illegal, but it doesn’t look like your charging” he states. He looks around though, as if to see if there was anyone of high power around, anyone that could get him fired from his job before he pushes his hips forward. His cock is not a terrible large thing, about 12 inches, which was in pony terms rather small, but it pleases him when he pushes into the mare and finds her rather tight.

Heartmend, grimaces a bit, whining as the guard pony fucks her hard and fast, depositing his cum inside of her, which makes her gasp out with a “Hey, you can’t do that!” He rubs his cock against her face, wiping the cum off of it there, and Heartmend can’t deny that this pleases her somewhere deep inside.
Heartmend feels her heart pounding roughly in her chest, she didn’t get to cum from the first stallion, and she wants to cum, but she refuses to admit it. As she stares at the crowd of ponies, she notes some of them laughing at her, “Look at that whorse” they say.

She feels tears in her eyes now, what if one of them knew her, she could never ever own up to it. The next pony to approach her is Donut Joe, the owner of the shop that they were outside off. “Well well, look at what we have here” he says, chuckling, his cock hard underneath him, 18 inches long, and rather girthy.
He positions it in front of her face, “Lick” he says, and she does, while she wants to bite his member, she knows that if she did, she could get in trouble and possibly even go to jail. She knew that even if she old the court what was happening, the people who were watching her were in a greater number.

She licks and sucks at his cock, which tastes sweaty, and then he asks her to lick his balls. They taste possible worse, but she does it. When the donut pony pulls away his long tool is slick with spit, he uses this for the justification to use Heartmend’s other entrance. He presses the flat head of his broad member to her unused entrance, popping it in with a groan.
Another creature approaches, a minotaur named Iron Will who was doing a seminar is Canterlot, thinking his assertiveness training may be of better use to the nobility there. What he finds makes his member harden, its full 20 inches.

The bakery pony continues to shove himself inside her, working himself into a quick rhythm, enjoying the tightness off her ass, as Iron Will strokes his member, moaning and grunting. Heartmend lets out a light moan herself, almost enjoying this. When Donut Joe comes he approaches her face again, telling her to suck his dick, and that’s what she does, her black bangs brushing over her eyes.

Iron Will approaches her now open marehood, thrusting his large member inside of her cunt, soon both he and Donut joe have a rhythm as they fuck different parts of her body, keeping her in a spit roast . They thrust and hump quickly, and it throws her over the edge, Heartmends stretched marehood makes her cum. The boys laugh, finish up, and pull out. Iron Will uses a hand to write, “Whorse” Across her forehead in a red marker.

Heartmend feels utterly humiliated when they walk away, leaving her dripping with warm cum, which dribbles down her chin and legs. The night is almost over when the last ‘customer’ approaches. A Diamond dog. He was in town doing some sort of pawning, and is interested in this mare. Brothels and public sex were not common in the Diamond Dog culture, so he looks thrilled when he sees her, his member angry red and tapered, his balls swollen under her.

“Pony for fucking?” he asks, Thunderlane interrupts Heartmend to nod and say, “Yep, that’s right” The diamond dogs cock isn’t as big as the pony or the minotaur so shes relieved when he pushes into her, it feels good, very good, and he humps and thrusts himself against her, balls thrusting against her, making her moan out a bit as they hit her clitoris. Then the swelling happened.

The bulbous base of his cock grows and thickens until it is the size of a grapefruit, locking them together, she gasps in pain as he stretches her to the brink and keeps thrusting against her, until he simply cant anymore.

The Diamond dog stays locked in her for nearly an hour, his knot not releasing its grip on her insides. Many ponies walk by, giggling, and pointing, some even inquire if she’ll be back next week. This entire event had been awful, and yet, as the dog thrusts the last bit before pulling out— she cums again.
Thunderlane chuckles, as he looks at the other, spent pegasi. She looks tired, and he is tired, “Well I’ll leave you here, and have Cloudchaser come and unlock you in the morning” he states, trotting away.

Heartmend feels so very alone, and almost hopes someone else shows up.