Classy Erotic short Stories:
Pickup Alley

Alley sat at the bar, her back to the crowd. It was noisy, and hot, and as she sipped her gin and tonic, she thought she’d head home after this last drink. In the stuffy bar, she was glad she chose her favourite white cotton dress for the night, the one with no back and tied  together by a thin string of fabric.

The mirrors above the bar reflected images, shapes of the patrons milling about behind her. She felt the man approach before she found him in the mirror, his body radiating heat as he stood next to her. She sipped her drink, pretended not to notice him standing uncomfortably close in the crowded room.

His fingertips touched the nap of her neck, travelling down her spine with the lightest touch that made the hair on her arms stand rigidly alert. “Your dress is about to come undone,” he said, fingering the loosened knot that held her dress in place. “Would you like me to tie it for you?”

Alley arched her back, slowly turning to look at him, her large, blue eyes wide under thick black lashes. He peered back, eyes heavy lidded and his lips pouty, his lower lip wet. She could’ve babysat for him in high school.

She smiled, giggling slightly that this young man was hitting on her. He smiled, too, but for different reasons. His hand still lingered on her bare, lower back. “If you would, please,” she said, and he obliged.

He motioned to the bartender to refill her drink, and before she could protest, another sat in front of her. “I’m older than you think I am,” she said to him.

He smiled, revealing perfect, even teeth. He brushed a stray hair out of her eyes, and she stiffened at the intimacy. “Why does age matter?” he asked.

The crowd around them surged, pushing him into Alley and trapping her against the bar. Her body pressed against his hard, wiry frame. “I don’t usually like the feeling of being a cougar,” she said.

His hand, which was still placed gently on her lower back, slipped under the seam of her dress and playfully tugged on her g-string. “What do you think of that feeling now?” he asked.

“I could get over it,” she said.

They squeezed through the crowd and into the cooler, humid air. He took her hand. “My hotel’s just over there,” he said, motioning up the block. Her heels clicked on the cobblestones.

“You’re not from here?”

He shook his head. “I’m in town on business.”

“What’s your name?” she asked.


The curtains in the room were thrown wide open, offering a high-rise view of the city below and beyond. The full moon lit the room in long, grey shadows. Alley placed her fingertips on the glass, peering out. He handed her a short glass of scotch and with a deep breath, she threw it back, feeling the liquor’s fire heat her core.

His hands slipped around her waist, and she firmly grabbed his tie, pulling his face to hers. His mouth was soft, and tasted of liquor. One hand tangled in her hair, pulling it free of its pins, while the other pulled at the knot in her dress, untying the string he so recently tied. Another at her neck, and the dress fell to the floor, the white cotton fabric pooling at her feet on the soft, thick carpet.

She loosened his tie, unfastening it, and pulling it like a snake through the grass from his collar. Her sinewy arms wrapped around his shoulders for another kiss as his fingertips travelled up and down her sides. He pulled his button-down shirt over his head, tossing it to the side.

Alley pressed her hands onto the hard, defined muscles of his chest and shoulders. She watched them bulge as his hands cupped her high, round ass, finding purchase as he lifted her up, Alley wrapping her long legs around his waist. A few steps across the room and he dropped her on the bed, where she bounced into the soft pillowy mattress, giggling. He stood at the end of the bed, looking down at her, silouetted in the moonlight with the night skyline in the window behind him. He unhooked his belt, his pants hanging on his hips, where the lines of his defined stomach disappeared. He stepped out of his pants and underwear, his eyes fixed on Alley the whole time.

Her heart began to race as he slowly climbed onto the bed, his body bent low, the muscles in his shoulders and arms rippling as he crawled forward in a prowl toward her. His lips traced a line up her leg from her toes, stopping at her hip as he pulled her underwear off, sneaking a peek at her face, a grin on his before his tongue plunged in, licking the length of her slick pussy.

Her arms stretching overhead, Alley arched her back, a deep moan of satisfaction escaping her lips before she relaxed on to the bed. Eyes closed, she drifted as his tongue and lips massaged and tickled the soft folds of her shaved cunt. His fingers slid inside, his palm facing skyward, and he stroked deeply.

As he pinned her lower body to the bed with his free hand, Alley’s chest arched forward, her breath coming in short moans. One hand gripped the sheets above her head, the other caressed her own breast, massaging it and pinching her erect nipple. Her pleasure built, like shaken champagne in a bottle, until the cork popped and the fizzy tickle of the bubbles spread from her core, emanating in pulses throughout her body.

Alley laid on the bed, breathing heavily, only vaguely aware of him moving amid the fogginess enveloping her. He grabbed her legs, behind the knees, and slid her toward him. Positioned between her still quivering legs, he bent over her, placing a deep kiss on her lips, her own salty taste still on his. 

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