Playing "The Game" Ch. 02

Task 5: Put Full Finger into Ass

3:00

This time Olivia didn't even need 3 seconds. Her finger went into her ass easily like it was being sucked in. She let out a moan as it entered and she felt a little pain. Her mind raced as the pleasure of feeling accomplished, of feeling slutty and being on the high of extreme horniness meshed with the slight pain of her ass receiving something for the first time. It all worked together to make her feel the best feeling of her life.

Level 9 came and went quickly as it focused on her pussy. It progressed from sucking her fingers and tasting her wet pussy to finger fucking herself with two fingers for two minutes. It drove her wild doing all of this and showing it to the camera, letting whoever was behind the game see it. The time limits, even on the things that felt amazing, were hard to deal with, but also made the whole game hotter for her. Masturbating and wanting to cum is stopped by a limit of time. Having to do what she is told when she is told to do it. It all came together to make an experience like she had never tried.

Level 10 started and she hoped it would end with her cumming finally. She had worked herself up so much that she didn't know how much longer she could hold on.

Task 1: Suck on Marker and Insert into Ass

2:00

Olivia grabbed a marker from her desk and slid it into her mouth sucking on it deeply. She let the time keep clicking down, watching it get closer to the end, :23, :22, :21, the warning about everything being sent to her contacts popped up. Her heart pounded as the level of risk grew. She was loving that everything could come crashing down so soon. Never in her life would she have thought she would like this adrenaline, this extremely risk play, but here she was living for it. Finally she moved the marker from her mouth and slide it into her ass quickly and deeply.

Task 2: Fuck Your Ass for 2 Mins

3:00

Her hand started to move in and out dragging the marker with it. Her eyes closed and moans started to escape her limits. "Fuckkkkkkk," she said out loud as she focused on this new feeling that she loved. Olivia couldn't believe in a matter of minutes she went from being an anal virgin to being someone who was thinking about having more in her ass.

Task 3: Fuck Ass and Rub Clit for 2 Mins

3:00

Olivia continued fucking her ass with the marker and her other hand came over and started to rub her clit. Her body was starting to shake and move around, trying to get as much of the marker up her ass as she could. The fingers on her clit moved faster and rougher and her moans continued to grow in volume. She felt amazing.

Task 4: Insert 2 Fingers into Pussy while Fucking Ass

2:00

Two fingers roughly pushed their way into Olivia's drenched hole. She could hear the sloppiness of her cunt as her fingers rammed in harder and harder, deeper and deeper. "Fuck, fuck fuck... yessssss!" she yelled out not caring who heard. This was all so new to her, these feelings, these tasks, doing this so blatantly. Her mind, her heart, everything was beating and working overtime.

Task 5: Continue to Masturbate and Cum

15:00

These were the words that Olivia had been waiting for. She now, finally, was going to be able to cum. Fifteen minutes was ridiculous she thought fleetingly. She needed a minute, maybe two, she was so worked up, so on edge. Her hips started to buck back and forth forcing the marker and her fingers into her two holes faster and harder then she thought possible. Seconds passed that seemed like hours as her orgasm grew within her. Closer and closer she could feel it, any second now... "YYEEEEEEEESSSSSSSSSS!" Olivia screamed as she collapsed on her bed, her fingers falling from her hole, but the marker staying wedged inside. Her whole body felt amazing, like it was on fire, but in a good way. She tingled and melted and her mind switched off. Olivia's eyes closed as she began to fall asleep while The Game updated, "Level 10 Completed!"

Eventually she woke up, her eyes fluttering and trying to make sense of what was going on. It was darker in her room now, except for a single bright light. How many hours did she sleep? As everything in her mind started to come back to life she saw Charlotte at her desk doing something on her computer.

"Well hello there sleepyhead," Charlotte said turning to talk to Olivia.

"Uh... hi," Olivia was still groggy, partially from just waking up, and partially from having her best ever orgasm.

"Well it looks like you had some fun in here," Charlotte chucked while looking down at the floor beside Olivia's bed and eyeing the pile of clothes there, her dress, bra and panties. Olivia's face went bright right. "I was quite surprised when I walked in from the gym to find you laying in bed, tits completely exposed and your clothes all piled up on the floor."

That was the first time Olivia realized her blanket was down closer to her waist then her neck and her tits were out. Her hands quickly grabbed the blanket and pulled it up hiding herself.

"I... uh..." Olivia had no idea what to say and her face felt like it was burning from embarrassment.

"Playing the game again?" Charlotte inquired.

"Uh, ya..." Olivia returned sheepishly.

"You really like it huh?"

"Ya, it's, you know different for me," Olivia paused, "I didn't do anything crazy in highschool, so I guess this is me doing something crazy." As she said it, it made sense. Maybe this was her just trying something new.

"Well as long as you're having fun," Charlotte chuckled again, "want to grab dinner?"

Olivia couldn't believe how long she had slept, how could it be dinner time already.

"Ya, sure, I guess, let me just get ready."

Olivia reached over the edge of her bed to grab her clothes and tried putting them on under her blanket.

"What are you doing?" Charlotte asked laughing now,

"Getting dressed?" Olivia replied confused.

"Jesus, just get up and get dressed. We're roommates, we're going to see each other naked."

Olivia blushed again. She realized she really did miss out on a lot in highschool if Charlotte was any indication. She slowly got up and moved the blanket out of the way showing off her body to Charlotte. Her slightly too large stomach and thighs, her clean shaven pussy and her tits all coming into view. She felt vulnerable, like she was on display, and for some reason that made her pussy sparkle with wetness. Her hands quickly pulled her panties on to hide it. "Why is this happening?" she asked herself silently. Her clothes came on and she was ready to leave with Charlotte. Before stepping out the door she checked the app.

Level 10 Completed!

Level 11?

She didn't click "Yes", she needed a break, but she did check the leaderboard. Finally she found her name, farfromhome, number 46. Olivia smiled to herself.