Disclaimer: I don't own Pokémon, and sadly never will…
(A/N Ash is 18 Jessie 26)
It wasn't often Ash found himself a hostage of Team Rocket. Rarer still to find himself guarded only by one of them, Jessie to be exact. He had been blasted off along with Team Rocket accidentally from one of Pikachu's more powerful Thunderbolts and wound up in Viridian Forest with them.
They were quick to tie him up, but after a while, they got hungry, so Meowth and James were sent to forage for food while Jessie kept guard over him. Needless to say neither of them was in a particularly talkative mood, but Ash was going insane from the lack of anything to do, so he tried for a conversation.
"So…" he said, "does blasting off always hurt that much?"
Jessie turned to face her captive "why the hell do you care?!" she growled, mostly from hunger but some due to the fact that she was never polite and would never want to be so.
"Dunno," he admitted "just trying to kill the boredom, I guess."
Her eyes softened a bit "a little," she said "but we've gotten used to it."
As if by fate his stomach growled and Jessie chuckled a bit "Hungry are we, twerp?"
"Yeah, a little" he said. Even though she was technically the enemy, it was good to talk to her, after all it was killing time and some of the boredom.
He saw her reach into a small sack they had in the Meowth Balloon and pulled out a blue berry the size of her fist. She cracked it in half and held in front of his face, "it's an Oran berry," she explained "used to make pokéblocks but safe for human consumption."
Ash looked at her sceptically before taking a bite, living up to its name, it tasted just like an orange. He finished what she held in her hand before she started on the other half.
"Just don't tell James I fed you, 'kay?" she said
"Sure!" he smiled a genuine smile despite being her prisoner.
After another hour of no James and Meowth, Ash and Jessie started to get bored again.
Jessie sighed, "Got any other ideas to pass the boredom?" she asked her captive.
Ash thought for a second "…Truth or Dare?" he suggested.
Jessie looked at him considering what he might be planning in that tiny twerpish brain of his before nodding, "Okay but you're first." She said.
"Okay," he said, "Dare!"
Jessie thought for a second "Hmm, okay. I dare you to let me kiss you." She said with a chuckle.
To say Ash went red was an understatement he was blushing so hard he could have put the sun out of business. "F-fine" he said. Jessie smiled and crouched down so she was level with him and pushed her lips against his. Ash felt his blood start to rush south, but was prevented from doing anything by two things, one: he was tied up so he couldn't move and two: she was the enemy.
After she pulled away Ash spoke, "okay," he said "you're turn."
"Truth" she said instantly.
"Why did you kiss me?" was the question he asked.
She thought about it before assaying something so quietly Ash wasn't sure he heard her correctly.
"What did you say?" he said hoping she would reaffirm his suspicions
"I said I love you." She replied, lowering her head.
"R-really?" Ash asked, stunned.
She slowly nodded her head. "Yes, this is why I'm going to do this."
She reached into the sack once more and pulled out a knife, she walked over to Ash who paled.
"Don't worry," she said kindly, possibly for the first time in her life, "I'm going to cut the ropes and let you go."
With those words said, she cut the ropes as quickly as she could.
When the ropes finally fell away, she kissed him once again and said "Go, now. I'll tell James you escaped, but I want you to keep this little thing a secret okay?"
Ash nodded before running towards Pallet Town.
'Thank you, Jessie' Ash Thought to himself 'I love you, too'