She does, and she keeps making her cum in increasingly humiliating ways.

A few moments after Erica had squirted her juices all over the floor, Lisa spoke up:

"Wanna try again, Erica?" Lisa, sitting on the bed cross-legged, looked down at the defeated girl, who didn't get up from the ground "same rules, if you win, I'll strip and masturbate, but we need to make it more exciting if you lose, deal?"

"... Okay." Erica slowly sat up, she was still kneeling on the ground, her eyes were misty eyed, it seems Erica's orgasms came with a few tears.

"Rock, paper, scissors shoot!" Erica lost yet again.

"Not your lucky day, Erica," Lisa shook her head, laughing internally at her downcast victim "let's see, I have a magic marker to decorate your cute little body with as you masturbate this time."

Lisa stood up and rifled through her suitcase, pulling out a magic marker to use, she began scribbling and calling out what she was writing:

"let's see, lost a bet...."

"mosquito bites..."

"Lisa's toy..."

"free use on your pussy."

"huge slut..."

"There we go, start again." Lisa commanded, and Erica obeyed, she lay back on the floor and spread her legs open, bringing herself to another orgasm, Lisa noticed that the juices were not so much squirting anymore as it was a little trickle this time around.

This pattern didn't stop, Lisa kept offering Erica the rematch, and the latter kept accepting without any complaints, and obviously, Lisa did not lose once.

By the end, Erica found herself standing outside in the hotel hallway, leaned against the wall with one hand, wearing a buttplug and a little vibrator egg nestled in her now sore pussy all while being filmed by Lisa on her phone as she rubbed her clit, she had lost count of which orgasm this was.

when all was said and done, Lisa let her little toy rest, after all, she'd have a long and eventful day of losing ahead of her.