Schoolhouse Library - Twilee Tales

by The1Ryu

Planning Ahead

Planning Ahead

“Cheerilee I think it’s time we have… sex”

Cheerilee’s fork dropped from her hoof and clattered to the plate loudly. The patrons around the table the two mares were sitting at looked over with various levels of curiosity and contempt. But as Cheerilee started at her date in stunned silence most decided that the disturbance was at an end and went back to their meals.

“W-what?” Cheerilee stammered, as Twilight fidgeted in her seat, starring down at the table, her cheeks a little darker.

It wasn’t that Cheerilee didn’t like the idea of going to bed with the beautiful young mare across from her. In fact she had been dropping plenty of hits that she would have liked to enjoy that benefit of dating when they made things official two weeks ago. When Twilight didn’t respond to her signals Cheerilee guessed she wasn’t ready, or too inexperienced to understand the subtle hints.

Now Cheerilee was wondering if Twilight had picked up on her signals and this was a reaction to her feeling pressured by Cheerilee.

Cheerilee gave Twilight a soft smile and gently placed a hoof on Twilight’s, “You don’t have to say it like that Sweetie,” Cheerilee reassured her. “We’ll get around to… that when you feel ready, no pressure.”

“Oh yay I know,” Twilight nodded letting out a nervous chuckle. “But this is just the ideal time and we shouldn’t miss it.”

Cheerilee tilted her head, a confused looked coming over her face, “Ideal? Ideal for what?”

“For our dating timeline of course,” said Twilight, reaching down into her bag and pulling out a notebook. “I’ve done lots of research and it says the ideal time to have sex for the first time is near the four month mark.”

Cheerilee smiled lovingly at this. It was so like Twilight to try and schedule and organize something she was so nervous about, and Twilight had to be the most virginal young adult mare Cheerilee had ever met. It made her very cute at times.

“Twilight,” Cheerilee started in a gentle tone, “You can’t schedule something like that.”

“Not easily,” Twilight agreed, a proud look spread across her face. “But after a lot of research I found the most ideal times for everything. Becoming exclusive, physically intimate, family introduction, saying ‘I love you’, fist vacation, discussing kids, moving in together, and getting married. Then I charted them out on a relationship timeline.”

Twilight cringed a little as she stunned look on Cheerilee’s face turned to anger, and she didn’t feel much better when it became calm, a smile spreading across it. She realized had done something wrong, but this situation had never come up in her research.

“You know Twilight, I think we’ll wait a month before we become, physically intimate.”

“But,” Twilight stammered looking down at her notes, “That’s when we’re supposed to meet each other’s family. I can’t do that with my parents near-by.”

“Two months then,” Cheerilee countered her offer, unable to help enjoying watching the presumptuous mare across from her squirm.

“But-but,” Twilight looked back and forth from the notebook to Cheerilee.

“Do you want to make it three months,” Cheerilee asked in a warning tone.

Twilight struggled to find something to say, but just slumped in her chair and gave a weak, “No ma’am.”

Cheerilee’s smile brightened at Twilight resignation, but there was one more thing she needed to do to make sure Twilight knew where they stood.

“Oh and Twilight,” Twilight looked up nervously, “I love you.”

Twilight gave a last pleading glanced down at the useless notebook clutched in her hooves, then met Cheerilee’s eyes and gave a resigned but completely honest. “I love you too.”

Author's Note:

The random prompt for this one was presumptuous. I knew right off that Twilight had to be the presumptuous one in this scenario and it was going to have something to do with progression of their relationship. One Google search later and I had all the material I needed.

Comments

[Talon and Thorn]

Awww!

“But this is just the ideal time and we shouldn’t miss it.”

What right now?

Right Now

In this restaurant

Yeah!

Fair enough then

[The1Ryu]

5802046
Oh god that's hilarious.

And to the pegasus question: Ground ponies fighting over rocks, not their problem.