Obstacle Arises

Zack stared at Jessalyn in utter shock.

“Did you just… you’re pregnant?” Zack asked, stunned.

“Of course I am pregnant! We laid together four months ago, and now your bastard child is in my womb.” Jessalyn said, clearly surprised that Zack didn’t remember this.

“Right. Yes. I do recall now.” Zack blinked.

“Now, why is Lady Ashley Woodsen in your carriage?” Jessalyn demanded. Zack took a second to think.

“I am not wedded to you, Lady Jessalyn. I have no obligation to remain faithful to you.” Zack said, trying to put off some of whatever charm got Medieval Zack all the girls.

Jessalyn placed a hand on Zack’s arm, and she tugged him closer, and Zack was shocked as her breasts mashed against his chest and their lips met.

“You have no obligation, true. But I am yours, my lord.” Jessalyn murmured softly, stroking Zack’s cheek.

God, this was so fucking WEIRD! These women who Zack had no memory of being with were all over him. It was mind-bending trying to adjust to this. If only there was some way Zack could get the memories of his medieval self, then he’d have some clue of how to navigate around the people of this odd alternate reality.

“I am glad to hear that.” Zack said weakly, and stepped back from Jessalyn.

Jessalyn seemed to understand Zack was done talking to her, and she nodded, and walked to the door of her carriage.

Zack walked around Jessalyn’s carriage and climbed up into his own, and sat down opposite Ashley, who looked worried.

“Is everything OK?” she asked, as the carriage started rolling forwards again.

“I think so. Apparently, medieval Zack got Jessalyn pregnant. It’s so hard trying to figure conversations out with zero context.” Zack sighed.

“Wow. That’s… pretty hard to wrap your head around, huh?” Ashley said.

“Yeah. But I mean, I guess this is easier to understand than waking up in bed with my cousin.” Zack muttered.

“I wonder just how many women medieval Zack got with? I mean, he’s a lord of the most powerful non-royal house in the area, isn’t he? He’s gotta have a big head.” Ashley theorized.

“That actually makes a lot of sense. So, what, he just tosses his title around, and then sleeps with whoever he wants?” Zack shuddered.

“He sounds like an asshole.” Ashley smiled. Zack gave her an unsure smile.

“Oh, I’m not calling you an asshole.” Ashley quickly clarified.

“I figured, but I wasn’t 100% sure.” Zack admitted.

———

An hour or so passed, but it was hard to tell because watches weren’t a thing yet.

The carriage rolled to a stop, and Zack got out of the carriage first, and then he reached up and offered Ashley a hand. She laughed and took it.

“How medieval of you.” she winked.

Zack and Ashley walked up to the front door of the looming McRose estate, and Zack rapped the rose-shaped knocker a few times.

The door was opened by a plain-faced boy that Zack vaguely recognized from his math class.

“We are here to see Lady Chloe.” Zack said politely.

The plain-faced boy gave an apologetic smile.

“Lady Chloe isn’t here presently. Her sister, Lady Holly is, if you would like to see her instead.” the boy apologized.

“I’m afraid we must see Lady Chloe, urgently. When will she return?” Ashley inquired. The boy looked at her shyly, and Zack guessed quickly that the boy was crushing hard on Ashley.

“I- I’m not sure, Lady Ashley.” the boy apologized again.

“Could we speak with Lady Holly, then?” Zack asked.

“Of course. I will see if she is welcome to you visiting her.” the boy bowed, and closed the door in their face.

“So, Chloe’s not here?” Zack sighed in disappointment.

“Should we make a bet on whether medieval Zack and medieval Holly slept together?” Ashley asked.

“Holly’s only sixteen!” Zack stuck up for his best friend’s little sister.

“No she’s not. If we’re both twenty, that means she’s eighteen.” Ashley reminded Zack.

“Oh. Yeah, right. It’s weird being two years older than I actually am.” Zack shuddered.

“Everything about this world is weird.” Ashley huffed.

The door opened again not long after, and the boy wore a sheepish grin.

“Lady Holly is currently occupied. If you would like to wait for Lady Chloe to return or Lady Holly to become available, the parlor is available.” the boy sighed. Zack and Ashley exchanged glances.

“Could you just let Lady Chloe know that we came by?” Ashley asked. The boy nodded eagerly.

“Absolutely. Yes, ma’am.” the boy said, eager to please Ashley.

“Thanks.” she said, looking a little amused.

Zack and Ashley walked back towards the carriage.

“So, what now?” Zack asked.

“Let’s go back to House Bishop. We can work out a plan there.” Ashley sighed.

“Alright.” Zack said, and looked up at the carriage driver.

“Back to House Bishop, please.” Zack said.

———

It was late at night when the carriage rolled back into its’ parking spot at House Bishop.

Ashley was sleeping soundly, and Zack was exhausted. Zack opened the carriage door, and, not wanting to wake her, he lifted Ashley up in his arms.

The world was incredibly dark. There were no lights, whatsoever. The carriage driver lit a lantern.

“Shall I escort you to the front door?” the carriage driver asked quietly, glancing at the sleeping Ashley in Zack’s arms.

“Yes, please.” Zack nodded.

The carriage driver led Zack across the pitch-black grounds and to the front door, where he knocked.

The door was opened by Madison, and Zack gave an instinctive smile upon seeing the girl, holding a lantern in her hand.

“Lady Ashley fell asleep on the carriage ride in, can you lead me to an empty room for me to put her in, Maddie? Uh, Madison, I mean.” Zack hastily corrected himself.

“Of course, my lord.” Madison said.

She led him through the manor to the nearest empty bedroom, and Zack laid Ashley delicately down onto the bed.

Then, he let her be and quietly closed the door.

Zack turned to Madison, who was looking at him with wide, almost anticipatory eyes.

“Could you escort me to my bedroom?” Zack asked. Madison nodded.

“Yes, Lord Zack.” Madison said softly, and she led the way through the quiet manor.

When Madison reached Zack’s door, she looked at him, and Zack was a little bit surprised to see hope in her eyes. What was she hoping for? A tip? Did one usually tip their servants?

“Thank you, Madison.” Zack nodded, and headed into his room.

He saw a figure laying in his bed for a second before Madison closed the door behind him, and the room was thrust into darkness. Zack fumbled with his shirt and pants and stripped down to just his long underwear, before feeling his way through the room to the edge of the bed and climbing in.

Zack heard stirring on the other side of the bed. The occupied side.

“Zack?” a voice murmured. That raspy voice was easily identifiable. Taylor.

Oh, no. Medieval Zack was sleeping with Medieval Taylor, too?

“Hey. Sorry to wake you.” Zack said softly. More stirring, and then Zack felt soft hands on his chest, and then a body pressed up against his, and he felt hair under his chin.

“It’s ok. You know I don’t like sleeping alone, anyway, little brother.” Taylor sighed contently. Oh. Maybe she wasn’t sleeping with her brother. Well, she was, but she wasn’t like SLEEPING sleeping with her brother.

“Well, hopefully now you’ll sleep peacefully, then.” Zack said.

“Where were you today?” Taylor murmured.

“Visiting a friend.” Zack answered, not untruthfully.

“Hm.” Taylor said, and then her breathing turned regular. She was asleep.

Zack was kind of a toss and turner, but with Taylor snuggled up against his chest, he couldn’t do that, which sucked.

But eventually, Zack managed to fall asleep.