Chapter 2: Once a loser

"What?" he yells in confusion.

A second chance system? What the hell is that? But before he gets the chance to fully descend into panic, the elevator door opens and he sees another hot busty girl coming out of the elevator.

"Parker, hey! I’ve been looking all over for you," Jessie says with a loud voice and happy look on her face.

[SYSTEM INITIALIZING:

You have been given one opportunity to correct the greatest failures of your previous life.

Main Objective: Become the person you were supposed to become.

Failure Condition: Repeat your previous life.]

No. No. No.

[Mission one: make Jessie Halls fall asleep with an orgasm]

"No way" Parker mutters. He remembers exactly how he used to feel about Jessie from when he was in college. He could barely look in her eyes, how the hell was he supposed to pleasure her into an orgasm?

Jessie has been his crush for a long time and she is also one of his biggest regrets.

Parker looks at his old plastic watch and sure enough, the time reads eight fifteen p.m. It’s the exact same time she complained about her sleep schedule to him. That day, he had stumbled all over his words and ended up running off instead of offering to sleep next to her.

"Holy fuck, I’ve really, really gone back in time," he whispers to himself. He lifts his head to see her coming in his direction and his throat goes dry. He has the chance to fix his mistake, but then, he’s still himself. He’s still the same awkward Parker Ross, so he chickens out and runs in the opposite direction to hide in the corner.

His eyes dart around the hallway as he pants.

"Uh...system, what the hell is happening?" he whispers and the system responds immediately, unfortunately the response is not what he really wants to hear.

[Reward for this mission: have access to the answer of every question set for the tests tomorrow]

[Failure of this mission: Repeat past mistake of failing the test and missing out on the future trip]

Shit.

He remembers this part of his life.

He failed the test and it turned out that the school prepared a special trip for the few students who passed. Most of his college colleagues who became successful in his future kept talking about that trip. That trip holds one of the keys to success. He has to get it.

"Wait, but why do I need to go through Jessie to get it? She’s my crush and I’m too shy to talk to her" Parker says.

[System: fail and find out]

Uh?

"I’ve got to get this..." he whispers and just in time, Jessie pokes her head from the corner to look at him. The action is surprising and Parker lets out a startled yell.

"Woah!" he places a hand over his chest in shock and backs up against the wall.

"Uh...what are you doing?" the beautiful brunette asks, full tits swinging in Parker’s face as she squats to talk to him. His eyes zero in on the plump breast and his throat goes even more dry.

"Huh..." he opens his mouth to say something, but nothing comes out, and his cock is suddenly twitching in his pants.

’No. No. Bad, Junior, bad’ he yells in his head.

Damn it.

"Parker?" Jessie asks, leaning even lower and he forces himself to tear his eyes off her mouthwatering cleavage.

"Uh, I was just...uh...tying my shoelaces" he lies and Jessie’s eyes drop to his shoes. "Oh don’t be silly, your shoes don’t have laces" she says with a small laugh and his shoulders drop.

[System: was a loser. Still a loser. Good going Parker. You have one hour before you’re classed as a failure. Again.]

"What?!" Parker yells and Jessie startles. The small act causes her full tits to bounce, and Parker’s dick responds with a throb.

"Are you okay? You seem to be having a really bad day" she says softly, sliding her fingers through his hair, and making him soften to her touch.

"I was just...stressed" Parker says and clears his throat.

"Since when do you have glasses on? It makes you look so handsome" Jessie says with a huge grin and straighten her back. She puts her hands on her waist and looks down at him with shining eyes.

"I’m having trouble sleeping and I wanted to see if anyone will help me" she says and Parker swallows the log of wood sitting in his throat all of a sudden.

This is his chance. His first mission is to give her an orgasm and make her sleep. He can either say yes and fulfill his mission or end up missing this opportunity.

"I can join you in your room if you’d like" Parker says and Jessie’s eyes sparkle with interest and happiness. "Of course, I’d like that. Why else do you think I came looking for you?" she asks with a giggle.

She takes his hand and pulls him down the hall.

"By the way, do you know my dad is the professor of the course whose test we’re having tomorrow? I can totally show you all the answers" Jessie giggles as she drags him to the elevator.

Woah, really?

Parker never knew Jessie was related to the professor, well now he knows, and he’ll do his best not to fail or miss it. This is truly his chance to have a successful life.

"Thank you, second chance system" he says under his breath.

[System: thank me after she has squirted on your cock and you’re not on your way to being kicked out by your former classmate, Ben.]

Parker grins to himself. He likes this. He will do anything not to disappoint himself.