The First

Bill looked back and forth between Ms. Carter and the man behind the wall. She was still a little dazed by the whirlwind of information and the sudden predicament. “When would I get it back?” she asked looking down at her dress.

Ms. Carter moved between Bill and the hole in the wall. “You wouldn’t. But you don’t have to do it. You don’t have to do anything.” Bill looked down at her dress again, she couldn’t sell it, she would be nude for the concert. Ms. Carter leaned in and whispered so the guy couldn’t hear, “You can have my cardigan and underwear after to cover up with, just don’t say anything in front of this guy.” It wouldn’t be perfect, Bill glanced at the cardigan it would still show a lot of skin through the large holes and she’d be running around in just panties. But she could maybe buy something at a vendor after, perhaps Regina merch.

Bill slowly nodded. Ms. Carter stepped out of the way as Bill slid one strap then the other off her shoulders. She blushed as the guy leering through the hole licked his lips. She took a deep breath before sliding her panties down her legs as well. The guy grunted, “Let me feel.”

Bill glanced to her teacher once again looking for guidance. Ms. Carter stepped behind her, touching her shoulders. Ms. Carter whispered again, “Say the word and it can all stop.” Part of Bill wanted that so much, to stop all the madness. To have not followed the directions given by the strange man with the skull ring. But the other part of her, the part that wished to succeed, wanted to help Ms. Carter, wanted to complete the challenge set before her.

She stepped forward as her teacher guided her. The man’s face pulled away to be replaced by his arm snaking through the hole. She shivered as his calloused fingers brushed over her pussy. “Tight little thing,” he said as he slipped a finger inside her.

He pumped his finger in and out, eventually adding a second. Bill moaned as his palm applied pressure to her clit, the fluttering of his fingers felt amazing within her. Her forearms rested against the wall as the stranger fingered her to an orgasm. Her legs quivered as her fluids ran over his knuckles.

She cooed as his fingers withdrew, her body shivered in post-orgasm bliss. The man said something but she didn’t quite hear him. She leaned over to listen through the hole, to find herself looking face to face with him. “You taste so good,” he said pulling his middle finger from his mouth. “You ever been fingered that good?” he teased.

Bill blushed, “Well that’s only the second time, and the first time we were really drunk and she didn’t know what she was doing so,” she paused, “I would say no, I’ve never been fingered that good.” She maybe over shared, the truth just kind of poured out of her. Maybe it was due to feeling a little dizzy from her recent climax.

“She? That’s hot,” he growled. Yep, she definitely over shared. “You ever given a blowjob then?” he asked pushing his finger into her mouth, her fluids still coating it. She was no stranger to the taste of herself, she had grown curious long ago and wound up quite liking it.

“No,” her tongue flicked over his finger. She slowly lowered to her knees, as she wrapped her lips around his knuckle.

“Fucking hell, I’m going to pop your bj cherry,” he played with her mouth running his finger over her tongue.

Her arm shivered with goosebumps as Ms. Carter gently touched her shoulder. She leaned in close, whispered into her ear. The warmth of her breath sent a shutter down Bill’s spine, “Are you sure you’re okay?” Bill just nodded, she was nervous but something inside of her stirred at the thought of finally experiencing more. She wasn’t a prude, she was just unpopular and shy enough that it hadn’t really happened. It was only 4 months ago at Simon’s New Year’s party that she’d given half a handjob and then lost her virginity, and nothing but her hand since. Ms. Carter hummed, “Okay, I’m going to trust that you’ll tell me if it becomes too much. Just say ‘stop’ and I’ll stop it. If you can’t or don’t want to speak up, just hold your fist out and clasp your fingers twice.” Ms. Carter guided Bill’s fist open then closed, open then closed.

“Misty, pleasure to see you,” the man smiled, “Have you had a taste?” He removed his finger, still coated in her sexual fluids and now her spit as well, and proffered it to Ms. Carter. Bill watched as her lips wrapped around his digit. She seemed to like it, was it genuine or was she merely acting for the stranger? Either way, Bill blushed while enjoying the show. “Mmm, Misty your mouth is heavenly as always, but I think the line is interested in seeing what the new girl has to offer.”

His finger pulled from Ms. Carter’s mouth with a pop. “Are you sure?” Ms. Carter purred, pushing her face into the hole. She ran her tongue over her lips, teasing the man. “You know how good I can make you feel.”

“Fucking hell, Misty. You’re incorrigible. Why don’t you be a good girl and fetch the girl’s clothes I bought?”

Ms. Carter leaned back, her body arching back as she grabbed Bill’s dress and panties from the floor. “Here you go,” she said as the man pulled the fabric through the hole. Bill followed Ms. Carter’s eyeline to the clock. 23:54:29. A few seconds ticked down and then the numbers whirred, 23:24:25.

The dopamine drop of watching the clock whir was slightly intoxicating. The whole gamified scenario playing into Bill’s instinct to perform, her drive to succeed. She turned her gaze back to the hole, where she saw the man on the other side dropping his pants, his cock springing free before he shoved it through the wall and inches from Bill’s face.