A polished and tweaked version of an older story I wrote. Enjoy!

XXX

Connor stood awkwardly on the tennis court, his racquet clutched in pale, sweating palms. Twenty years young, the college student was a slightly out of shape virgin, but he hoped to eventually change both those things with the expensive lessons he was taking at a private club close to campus. He hoped the exercise would condition his body, make him look more like the kind of man that women desired.

His white polo shirt was just a little too small, or he was a few pounds too heavy for it. Either way he looked slightly ridiculous. Worse still were his shorts, higher on the thigh than was fashionable, and too tight in the crotch. His moose knuckle was hilariously obvious, his virgin bollocks swelling against the thin, white fabric like a couple of soft boiled eggs.

The small, soft outline of his cock was just as obvious, pulsing ever so slightly as he stared openly at the pretty girls playing on the adjacent court, his virgin mind hypnotized by their bouncing breasts and tight asses as they grunted with the efforts of continuing their rally.

Across the net from Connor stood Riley, a former pro tennis player. Her brunette hair cascaded over her shoulders, perky breasts pressed tightly beneath a sports bra. Her ass, the perfect mix of muscle and fat was barely hidden by a short, pleated skirt that clung to her tan, shapely thighs.

Riley had a sharp pair of eyes, set within a cute, almond shaped face. Those eyes missed nothing, and noticed Connor's wandering eyes and decided to teach him a lesson. It was obvious he was a virgin, from his weak, stammering voice when he talked to her, to the way he couldn't help but stare at any hot piece of ass that crosses his path.

"Pay attention, Connor," she said sternly, losing patience with him.

“Huh?” Connor grunted, failing to tear his gaze away from the girls on the next court.

Riley's eyes narrowed, it didn't matter that she'd conned this pathetic virgin into paying double her normal hourly fee, she still expected his eyes to be nowhere except on her. Within a sly grin, she fixed her gaze on his bulge, even from here she could see his dick twitch in excitement as he watched the girls play nearby.

She bounced her tennis ball once, twice before springing up from the court, her muscular calves flexing. She tossed the ball with her left hand before delivering a thunderous serve with her right, her racquet propelling the ball over the net with a loud twang.

As she landed she smiled, her aim was true and the bright green Slazenger ball sailed perfectly between his legs, smashing into the comical bulge in Connor’s tight, white shorts.

Connor collapsed to his knees in agony and surprise, falling to his knees, his mouth open in a wide O. His racquet clattered to the ground, completely forgotten as his trembling hands cupped the throbbing bulge between his thighs. The pain was unlike anything he had ever experienced before. It was a uniquely male pain, a humiliation that only a man could understand.

Riley jogged over, circling around the net. She wanted a closer look at the sight of the groaning virgin. She knew he'd deserved it, and it had unfolded exactly as she'd planned. Still… she felt slightly bad knowing how easily and completely she’d emasculated him.

As he writhed on the court, his hands gently cupping his throbbing manhood, he felt a shadow fall over him. His blinking, tear-filled eyes made their way up Riley’s tanned legs, widening as he got a good look up her skirt. Despite the agony between his legs he couldn't help but notice she wasn't wearing any panties!

As his balls churned in his shaking hands, every detail burned its way into his virginal mind. Her pussy was smooth and flawless, a stark contrast to his aching balls and bruised cock. His mind fought to separate excitement from agony as he felt a surge of desire, a longing to touch her, to feel the soft, smooth sex between her thighs.

Riley noticed his gaze and smiled. "That's what happens when you don't listen," she said, kneeling down beside him. “But don’t worry, I'm a trained first aider. I'm going to have to check if you're okay down there.”

“Wait… what?” Connor protested meekly, unable to stop her as she pushed his hands away and tugged on his shorts. Riley unclothed him roughly, eager to add to his embarrassment and complete his lesson in male vulnerability and female superiority.

Connor's heart beat like a bass drum as Riley roughly probed at his aching balls. Her fingers were soft and warm, and he couldn't help but feel aroused by her touch. Despite the pain, he felt a stirring in his groin, a desire that his body couldn't ignore as his cock sprang eagerly to attention.

Riley gave his nuts a rough squeeze, grinding them together like a pair of plums at the fruit market. Her eyes widened as she watched his dick twitch and throb, she realized the chubby little virgin was actually enjoying this. She barely had time to move her hand away before he ejaculated. Thick ropes of jizz splattering across the warm clay.

They heard laughter nearby, both looked over to see the girls on the next court giggling and pointing as they stared at Connor's humiliating treatment.

“New balls please!” Riley shouted to them, her face breaking into a wide grin as all three women laughed.

Connor looked up at Riley, his little dick twitching against his thighs as his aching balls throbbed below. He was embarrassed and ashamed, but tried to smile up at his sexy coach.

"That's what you get for not paying attention," Riley admonished, standing up and dusting herself off. "Now, go clean yourself up Connor. And make sure you Venmo me double this week for the happy ending.”