Summer at last! High school was over, and Matthew had graduated last month with a respectable grade point average and would be off to college in September. He hoped the next four years would be better than the last. High school had not been kind. He had been a true geek. Being a member of the drama club, debate team, and an after-school ballet dancer had left him a social outcast. He had skipped the prom and had never been to a school dance. His few awkward attempts at engaging with girls had been universally rejected, some with more kindness than others. And so here he was: eighteen years old, a high school graduate, and an unwilling virgin. He had never even seen a naked girl in real life, and with his current social schedule, that was unlikely to change any time soon.
But for now, he had other things to do. College was expensive, and in order to start raising some spending money, he had taken to yard work. Most of the houses in this area were large with big yards and fancy gardens, and more often than not, a hedge enclosing the whole property and providing some privacy. Most had pools. His parents had made some arrangements, and so he arrived at the home of Mrs. Phillips, ready to work.
“She’s expecting you, so just go through the gate and around back,” he had been told. And that’s what he did, only to stop in surprise as he reached the backyard. Mrs. Phillips was sunbathing by the pool in a sheer white bikini. Her feet were towards him, and her legs parted, giving him a nice view of the mound highlighted by the thin bikini bottom.
He gasped softly, which she apparently heard, because she sat up and smiled when she saw him. His eyes were involuntarily drawn to her chest, her ample boobs almost bursting out, her large nipples prominent under the thin fabric.
“Hi, Matthew,” she said as she adjusted her top. She was friends with his mother, but he didn’t know her very well. He knew she was divorced and in her early forties but had never said much more to her than hello. He had certainly never seen her in a bathing suit or realized how sexy she was. Her breasts were large, and her hips wide, and he couldn’t help imagining the sheer white top melting away. His cock twitched slightly in his shorts.
“You know what to do,” she said. There’s lemonade there; help yourself. Let me know if you need anything.”
“Y-yes, ma’am,” he said as he made his way to the hedges and began clipping. Half an hour later, he was overheated and removed his shirt, revealing his toned dancer’s body. Something made him look around, and he saw Mrs. Phillips peering at him over the top of her sunglasses. She stared just a little too long, and he blushed slightly as he realized she was checking him out. She gave him half a smile before she picked up her cell phone and began pushing buttons.
A few minutes later she called him over, making no effort to hide her lascivious gaze.
“I need to do the other side. Do you mind?” she asked, handing him a bottle of sunscreen before laying on her stomach and undoing the straps of her top. Matthew caught his breath and froze. He hadn't seen anything, but just knowing that a topless woman was lying down in front of him was enough to send his heart racing.
"Well, go on then," she said, looking over her shoulder and grinned. "It's no different than with one of your girlfriends."
"I've n-never had a girlfriend, ma'am." It had slipped out and he immediately regretted it. He had been so entranced by the view of the white bikini stretched thin over her big ass that he had spoken without thinking.
"Really?" She rose and half turned. He couldn't quite see her nipple. "A good-looking boy like you? I would think the girls would be lining up to go out with you." Her eyes travelled up and down the length of his young body.
"No, ma'am." He felt weak in the knees.
She turned a little further, resting her chin on her palm, her elbow shielding her ample breasts from his sight. She pulled a knee up towards her head, spreading her legs and stretching the thin cloth tight over her ass and the mound of her pussy, all on full display.
"Ever been laid? Even at a drunken party with a girl you don't quite remember?"
"No, m-ma'am." His face was hot and flush with embarrassment and not just because of the pointed questions. His cock was now harder than it had ever been in his life, something Mrs. Phillips could not have failed to notice as his thin athletic shorts did little to conceal his modesty.
"So, have you ever even seen a naked woman? In real life, not on a screen?"
He shook his head, his mouth too dry to speak.
"Then let me be your first." She rolled over on her back and put her hands behind her head, exposing her enormous boobs to the summer sun. Matthew gasped, and it was several seconds before he remembered to breathe again. Mrs. Phillips had great boobs. They were large and full, creamy white against the tanned skin surrounding them, and topped with pale pink nipples that stiffened under his gaze. After a moment, she chuckled softly.
"Well, what do you think?" He jumped slightly at the sound of her voice but made no real effort to shift his gaze from her chest.
"They're wonderful." His voice was shaky and little more than a whisper. He continued to gaze at her, nearly speechless with awe, watching as her tits rose and fell with her breathing.