Yes.

You resolve to march onward, thinking of the guard's sword for a second time. Thankfully the town does come into view an hour later. When you end up in it's streets you're already used to keeping your head down and you do so for remained of the walk. This practice of looking down seems to be the only thing that keeps you going as people call out and laugh at you in the street.

When the cart stops you take a brief glance around to see a guardhouse nearby with other carriages parked outside. You must be in some rear stable area off the main road. Your owner disembarks and you muster up a look at her.
"Follow me." she says, tugging on your leash.
You fall to the ground, exhausted from the journey.

It takes the last bit of your strength to get back up and keep going. Behind you the sounds of the other boys being let out can be heard. A heavy metal padlock clicks, footsteps follow, and whispered gossip begins. You could turn back to see them but you'd rather not. You can't take that shame, instead you say nothing and stare at the ground.

When your owner finishes leading you, she fixes your chain to a post at the back of the guardhouse. You hear the other boys being lined up close by but you dare not look at them.
"Want to do this now, Vicky?" your owner calls.
"Yeah, it's getting late. I want to sell these orphans before sundown."
You hear a knock on the door nearby. When it opens, you continue to stare into the dirt while listening to your owner talk with some other women.

"Hey, girls. The mistress at St Anne's sold me one of their sissies." your owner starts.
"He isn't good for any house or anything. I'm gonna keep him around, have him clean the floors and take cock." she says. A crowd laughs.
"You offering some boypussy, Leah?"
"Yeah, he's chained to the post right now. Any takers?" your owner, Leah calls out.
"Hell, I've got some time between shifts. Lemme see him."
"I'm in."
"Same."
"Let's see this piece of ass."

You hear chairs being moved around and armor clinking as footsteps come out into the back road. Banter fills the street.
"Is this him? He's a cutie."
"Hello boys."
"Hey, boys."
You hear Vicky's voice.
"Curtsy for the nice guards." she says and chains rattle in response.
"Very polite."
"How charming."
"Leah, why do you have the others here? Are they up for grabs too?"
"Nope, they need to watch this. For their own good. Orphanage wants it apparently."
"Aren't you going to have the first go, Leah? He's yours isn't he?"
"Officially I guess but I'd say he's the guards now. Besides, I'm married, you know that."
"Sheesh, doesn't mean you can't have a little fun."
"Yeah, Leah. Loosen up a bit."
"No thanks, I'll be home with my sweetheart soon enough. One of you girls can have the first go at him."

Someone tugs at your chain. You look over to see Leah surrounded by a crowd of guardswomen, all eyeing you up. You stare back down at the ground.
"Get on your hands and knees." you so do.
"At least he takes orders okay." one of the women says. You look into the dirt.
"Well, from what I saw, he wasn't so good at that back at St Anne's." Leah replies.
"You do exactly what these girls say. They have my personal permission to take you to the guillotine if you don't. Understand?" you nod again. Leah commands again but this time it's to the boys nearby.
"Watch closely, boys. This is what happens when you don't listen to your betters."

Someone pulls at your panties, tugging them down to your knees. You feel something cold and wet poke at your asshole. It feels like one of the guard's fingers. When it pushes past your asshole you stifle a yelp from the sudden pain. Stare at the ground, you think. Just let it happen and soon it will be over. Just don't look. You struggle to relax with the finger sliding in and out of your ass.

"Damn, he's tight."
"Not for long." someone laughs.
"Sorry to show you this, boys."
"Yeah, it's just how it is. Be good to your women and you won't end up like this."
"Get it over with, Sarah." Leah says.
"Fine."

You feel the finger withdraw, giving you a moment to relax, but you know there's more coming. The sound of ruffling is followed by something bigger pressing against your hole. You stare into the dirt, breathing heavily. It pushes against you but to no avail. Your breathing worsens. The thing against your asshole pushes even harder, then harder, then harder still, until finally popping inside. Your fingers dig into the dirt as your suppressed scream escapes in a pitiful sound befitting some wild animal. Your anus is stretched painfully wide by some hot and thick girlcock that is now inches inside you.

Exhausted from the hours of walking and wracked by pain you collapse forward into the dirt but strong hands grab a hold of you and pull you back up into position. The cock inside you begins to push forward now, diving deeper, it slowly pushes into your ass. You're making whimpers now. One of the guards holds you in place while a tear of pain runs down your face. You stare into the dirt. Don't look at the boys you think. Don't look. You close your eyes.

"Oooh, he has a nice ass." Sarah says.
"Damn, might even be a virgin." another says.
"Probably is."
"You boys watch closely. This kind of fucking is what you can expect from upset owners."
"Be good and a woman will always treat you tenderly."

As the hands on your hips pull back the cock is pushed even deeper inside of you, rearranging your insides, and causing you to tremble. When it finally stops, you feel that you've been pulled up to the guardswoman's crotch. You can barely move, paralyzed by the feeling of being hilted for the first time. You don't have long to think about it because the girlcock suddenly slides out then it rams back in. You whimper uncontrollably. When the real fucking starts you find yourself unable to stop whimpering with each powerful thrust. Sarah takes you rough a deep.

After a few minutes of this, your body is growing used to the monstrous intrusion that's hammering away at you relentlessly. There's even a sense of arousal that starts to build in you, replacing the feeling of pain with a gradual and mounting pleasure. You don't know why, but your cock begins to harden while being taken doggystyle behind the guardhouse like some street mutt. Eventually, your whimpers turn to moans and the guards take notice.

"He likes it. Look, he's getting hard."
"What a slut."
"You getting close, Sarah? My shift starts soon."
"Fuck, almost. Ah damn. Damn. Damn, that's good."
"Don't break him, girl."
"Nice catch Leah."
"Yeah, he looks like a keeper."
"Yeah, nice catch."
"Mind if we take him inside?"
"Fine by me. Just finish up here first."

A few more hammering thrusts and you can't take the pleasure anymore. You cum into the dirt road and let out a long drawn out moan. Your asshole spasms, tightening uncontrollably around Sarah's massive girlcock. It hardens like a rock as it dives into you for a final thrust. Pulled against the guard, her grip on your hips tightens like a vice as she unloads a heavy load of semen right into you. The feeling is amazing. The gooey warmth causes your cock to spasm again. Sensations of fullness you've never felt are washing over you now. And then, it hits...

The teachers of St Anne's had warned you many times but in all the days events you had forgotten about it until this moment. The ****-like effects of the internal girlcum creep up into your consciousness and you realize your world is starting to spin. Hitting you like a crashing wave, a hazy numbness washes over you. You're unable to form proper thoughts. Your body feels warm and tired. Sarah releases her grip on you. Like a used rag, you crumple to the ground, hearing a popping sound as a spent cock leaves your abused ass. The sound is distorted, all sounds are distorted in fact. You hear people talking but their words are hard to make out. Warm semen pours oozes out of you. You drool, mouth agape.

In your **** state you barely make out the sight of the other orphan boys being led away. You make out faces of horror and shock but you're not sure how to feel about it. It's really tough to think in general. Someone strong grabs a hold of you. You hear chains rattle. You're lifted up, sending spurts of cum out of your ass. Once you're brought inside, a guard tosses you onto a comfy bed that feels absolutely heavenly. Another girl grabs a hold of you and rolls you over before easily slipping her cock into your cum-lubed hole. It feels great to have another one in you. The drunked feeling combined with the sensation of being filled is the best thing ever. The first thrust is almost enough to make you come instantly. For the next while you're face down, ass up, creampied over and over by the guard. Your ass is red from being slapped over and over while a small lake of cum is gathering between your thighs. After what you think is your fourth creampie your increasing cumdrunkenness is too much for your little body to handle. You pass out from utter bliss and darkness takes you.

(Your journey is over. After failing to impress any potential owners, you were sent away to be sold in the city to the highest bidder. Instead of accepting your fate, you tried to escape and wound up caught and humiliated. Rather than being sold to a decent woman, you were given away for free to the city guard. After a long walk into town you were brought behind the guardhouse and were fucked in the ass right before the other undesirable orphans. After serving as a lesson in dickgirl superiority you were brought inside. That day the guards ran a train on you until you passed out. In the coming days your new life was laid out for you. You would spend your time on all fours, speaking to no one. With one word you were to present to the guard and take their seed anally like a good house sissy. Though there was talk about getting you to clean or work, the effects of the guard's combined semen quickly warped your mind. After a month or two, you became nothing more than a cumdump who's only skills are moaning like a whore and milking cock with your ass.)

Bad End.