On the Road.

Ultimately she decided on something she could take off and put on easily.
Knowing begrudgingly that was probably part of the days agenda regardless of the details of what Olivia and Master had planned. So she wore a flowy knee length sundress.
Boyshort full bottomed panties and a cute pushup bra. As small as the buttplug was it was still a lot for the cheerleaders virgin asshole and it took her 3 tries to get it in.
She found the feeling odd but not unpleasant, and took a few laps around her room to see how it felt while walking, found she could walk comfortably but was aware of it with each step, when she sat down to insert the vibrator there was an odd pressure as the plug was shoved against her.
But if anything she kind of liked it.
Inserting the vibe took decidedly less lube. She had broken her hymen horse back hiding years ago and the small vibe slipped in without much protest.
She experimented with pulling it out by the loop and shoving it back in a few times getting braver with how far she pushed it each time.
Having to hold herself back from getting too horny and happy with how secure inside her it was she put her panties back on feeling oddly full.
She had another 15 minutes to wait before her phone dinged with a message from Olivia telling her to come downstairs. Her legs felt like lead as she walked out of her apartment saying goodbye to her parents.
Olivia was waiting outside of her building not having even gotten out of her car.
"Hey baby how much for an hour" She joked as Amy went around to the passengers side. Simply thankful she got to ride clothed today.
Olivia started playing with her phone as soon as Amy sat down. Suddenly there was a low rumble of vibration inside her. Amy half gasp and half moaned. It felt so good.

The vibration was starting to get more intense, causing Amy's panties to get soaked within seconds. It felt like a warm fire inside of her, burning and spreading through every inch of her body. She could feel each vibration, sending shivers down her spine with every passing moment.

Olivia started to grin, watching as Amy squirmed and moaned in her seat. She cranked the vibrations higher leaving Amy to squirm.
"You will ask permission to climax."
A few minutes later Amy was panting and getting very close to an orgasm.
Through gritted teeth she asked
"May I...May I cum."
"No you may not" came the reply as Olivia swiped on her phone and the vibrations went to almost nothing.
Amy was left panting and frustrated as she felt the near-orgasm fade into a deep arch.
The toy keeping her elevated but not doing nearly enough to give release. About 20 minutes of highway driving later Olivia, trademark smirk in place, asked her.
How badly do you want to cum right now?" She boosted the speed of the vibrator, just a bit, after she asked.
"Really badly." Amy admitted breathlessly face burning with shame.
"Get naked and you can." Amy couldn't believe she was actually considering it.