Like a proper sissy.

It's tough to say whether it's Josie's pleasantness or the guardswoman's humiliating display, but something has killed your rebellious spirit. It's time to give in to this buxom woman and take your role as her obedient property. The male's place in this world is all to clear now. No sense in fighting it. You step forward and curtsy just like you were taught back at the St Anne's.
"Pleased to meet you." you reply.
"Well. Aren't you a proper sissy." she says.
"I was worried you'd be one of the rotten ones with no manners." she continues, brushing your hair affectionately.
"How about you say goodbye to guardswoman, Leah. We've got a carriage to catch."
"Goodbye, Miss Leah." you say to the tall brunette.
"Be good." she says in a commanding voice before wandering off to sell the other boys.

With the amazon walking away, you're led by Miss Josie to the roadside where a number of carriages await. It doesn't take her long to flag one down. When you hop inside it's remarkably nice with padded cushions and little windows that peer out into the city. Josie sits beside you and puts her hand on your leg, rubbing up and down your thigh.
"Now, Taylor. You know what this means right?" she says, momentarily flashing your ownership papers.
"You're my new owner?" you say, trying to act cute just like you were taught.
"That's right, Taylor." she says, sliding her hand further up your leg. You feel a warmth start to spread throughout you.
"If you act like a proper boy then I'll always treat you right. Understand?"
"Yes, Miss Josie." you say, feeling your owners hand moving closer to your crotch. You're starting to feel turned on. "What's happening?" You think to yourself.
"Good." she says, pulling her hand away.
"I'm not one of those ladies who buys sissies like you because they can't get a spouse. I run a little business that needs cute boys like you."
"I expect you to work just like the other boys I've bought. Understand?"
"Yes, Miss Josie. I'll be good. I promise." you say. She smiles in response and runs her hand further up your dress. Your cock is hardening fast. Something about acting submissive to this woman is driving you wild. The brief brush of Josie's hand across your panties is enough to make you moan audibly. It feels so good.

"Shhh." she says, holding a finger to her lips. She leans close and whispers softly.
"We don't want the driver to hear, sweetie."
You nod in agreement. The sensation of pleasure is rising and a small wet spot is starting to form at the tip of your cock. You're going to ruin your undies if Josie keeps stroking you like this. You stifle your pleasure noises, breathing heavy as your new owner molests you in the back of the carriage.
"That feels good, doesn't it?" she whispers again, moving her hand a bit faster along your cock.
"Yes." you whisper, panting now as you feel the heat building. Moments later and your fingers are digging into the cushions as your body tenses.
"Gyahh..." you moan gently, trying your best to be quiet as your orgasm rides through you. Your dick pulses as Josie's hand cups your balls. A sense of bliss is followed by the feeling of cum oozing and sticking to your clothes. You continue panting, even after Josie's hand retreats.

"Good boy." she says.
The carriage comes to a stop and the lady at the front calls for you to hop out. What timing, you think. Your owner opens the door and steps into the road, holding her hand to help you.
"Come now, Taylor."
You take her hand and step into the street, legs still a bit wobbly from your recent orgasm. The sticky wet feeling around your crotch is icky but bearable. you follow Josie.

By now the evening has truly come. All around you lanterns hang from street posts and lights from nearby shops cast dim lighting into the city. There are no sissies in the streets, only women walking about. In fact, there is very little activity around here altogether, save for a single establishment nearby from which the sounds of clinking glasses and drunken revelry are easily heard. You're led towards this spot and notice the sign above the door that reads "Josie's Tavern", well that explains that, you think.
"After you." Josie says, holding the door open. You curtsy again before stepping inside.
The room is grand and rustic with wooden fixtures and a burning hearth off to one side. Tavern tables are filled by women enjoying food and drink served by sissies in maid outfits. The atmosphere is vibrant enough that your haziness starts fading. You spot a peculiar girl that seems to be giving orders to the different boys running about. She's a long haired redhead with freckles on her cheeks. From her spot behind the bar she turns to greet you two at the door.
"Guid eevenin, Josie. Gotcher self a new wun, did ye?" she calls in a heavy accent while passing a tankard of ale to a woman at the bar.

Josie walks to the bar and you follow in tow. There's a lot of excitement all around. Much more than what you'd seen at the orphanage. When you get to the bar Josie turns to face you.
"This is my assistant, Kyla. Kyla, this is Taylor." Josie introduces you.
"Guid te meit ye, Lass. Goddess yer a cute ane." Kyla says. You blush and curtsy.
"The pleasure is all mine, Kyla." you say.
"Good. I'm going to show Taylor his new room. I'll be out to help with things soon."
"Tak yer tiem, Josie. Tis all dun well this eevenin. See you rund, Lass."

Soon you're wandering down a hallway at the back of the room. The sounds of feasting are replaced by murmurings behind closed doors, snoring patrons in their rooms, and the thumping of baseboards accompanied by girly moans. As you're brought down this hall you eventually make a turn and wind up in an area that is almost completely quiet. A sign above the hall says "Staff Only". Josie pulls out a jingling keyring and opens one of the doors. Inside you see a somewhat spartan living arrangement. There's a bed big enough for a woman, set in the corner next to a dresser and a nightstand. The furniture reminds you of what basic amenities you had at the orphanage but they come with a private room. Though, you note that the bed is far more spacious.
"This is your new room, Sweetie. I hope you like it. It's not much but it's cozy. Bathroom's down the hall if you need it. There's clothes in the dresser for you."
"It's very nice, Miss Josie. Thank you for all of this." you say in response.
"You take it easy in here tonight and we'll start your training tomorrow. Sound alright?"
"Yes, Miss." you say with a bow.
"Good." she says, before giving you a kiss on the cheek and a warm smile.
With the evening coming to a close there's not much to get up to. Josie seems to hang in your doorway as you look around.