Simon leaned into the bar and tried to keep his eyes focused on the TV above the bar. Shy and 18, he had gone out with his roommates to supposedly celebrate his birthday, but by the third bar they had all scattered. Simon wasn't even sure where they were - but he had promised himself that college was going to be different. College was going to be when he stepped out. He was going to make friends, maybe even a girlfriend!
Simon didn't consider himself a bad looking man. He exercised, he ate well, and he took good care of himself. Where he struggled was his crippling anxiety. Something about meeting new people terrified him. He did alright if someone introduced themselves, but he had a hard time in social settings.
Like at a bar.
He knew he was probably not acting right. He kept glancing around, people watching or people creeping depending on who you asked. Located on a row of bars, the Green Door - where he was - acted as an anchor. A well established bar for a more mature crowd. Normally his roommates would have gone to a few dive bars but his birthday meant "something special", which was how they eventually ended up here. And where he was eventually lost by his friends.
He took a second to look around again, and his attention was immediately caught by an older woman at the end of the bar. Easily in her late 30s or early 40s, she had a dazzling smile. She was dressed casually, but professionally, with her long, dark hair, draped over her shoulder emphasizing her large breasts. Simon couldn't help himself, he was transfixed. She was talking earnestly with another woman, laughing, holding her glass as she talked to her friend. He blushed and started to turn away, but her eyes darted over and she saw him. He swallowed hard and looked away, before looking back with a half hearted smile and wave. She went back to her conversation.
Simon frowned at himself. Even before she looked excuses for why she would say no had started to flow into his brain: "She's older" "She's to hot for you" "You're not her type". Why couldn't he walk up to her? Why couldn't he say something? Frustrated he decided he needed to get away from the press and noise of people, and looked to find the bathroom - to which the sign indicated the stairs down were right behind where that lady was standing. Frazzled, Simon stepped back from the bar, straightened his shirt and bee lined to the door, his eyes focused.
He got past without being to obvious he felt, and started down the steps. A few seconds later he heard heels behind him. As he reached the bottom of the stairs, he felt a hand tap his shoulder. "Excuse me" a woman's voice spoke. He turned and it was her, the lady he had been staring at. She didn't seem particularly upset, more curious, her eyes were watching him carefully.
"Yes?" he stuttered.
She smiled, "I saw you checking me out at the bar." She gestured with her hands to indicate her chest. His eyes went their automatically. "Yes, like that." She laughed. "Do you like them?" He nodded. "It's okay to look I like to know when I'm appreciated." She grinned. "I like looking at you too."
He blushed a bit but smiled. "Do you?"
"Yes! Very much so. You saw upstairs right? Assuming you were looking at all the patrons and not just the ones with breasts, did you notice how most of the men here have let themselves go?" He nodded, though he hadn't noticed. "But you! You are something else!" She reached out and felt his upper arm, he was startled but she smiled and shushed at him. "Nice" she murmured as she squeezed his arms.
A tiny part of his brain was telling him he should be uncomfortable, but a much larger part of his brain - and other body parts was thrilled. He flexed his arm a bit and her smile broadened, though he barely noticed as his eyes kept marveling at her breasts. She grinned, "Want to touch them?" He nodded and reached his hand out, hesitantly touching the side of her left breast. She grabbed his hand and moved it more forcefully and fully into her chest. "There, like that!"
