Parking Lot Assignment by Jeffery

The Parking Lot Dilemma

The rain pounded down on the windshield, seemingly with no intention of letting up. He sat in the parking lot, gripping the steering wheel so tight little specks of the rubbery material came off in his hands.
How had it come to this? What was he really doing here in the parking lot of this bagel shop? And was he really going to go through with this?
His pulse thudded in his neck like a mountain stream does when the snow melts. He fought to control his breath and rested his head on the wheel for just a moment. Then he lifted his head and let out a long, slow sigh.
He knew he was going to go through with this. He had no choice.

For weeks, it had been that way. She brought him to his knees quickly and he knew almost immediately he would do anything for her. She knew it too, and used it to her full advantage. From the moment they met, he bought the drinks, held the car door for her, pulled out her chair. That first night she told him “You’re so well-behaved. I like that” and something in the way she said it made his cock stir.
He blushed and she saw it and smiled.
When he drove her home she turned to him and simply said “Come inside” and before he really knew what was happening she had forced him down on his knees and ordered him to pull her panties off and lick.
He found himself doing it willingly and she barked orders at him and yanked his hair hard to put his mouth in the right places at the right time. She came over and over and over until he lost track of how long he had been kneeling there and all his could smell was the smell of her juices as they flowed all over his face.
She pulled his head out of her crotch and dragged him to the couch. She undressed him and took his swollen cock inside of her, cumming again and removing herself before he could. Then she took him into her hands and jerked him off. Whispering gently and shushing him until he came. She took a salty puddle of his cum onto her fingers and shoved it into his mouth. He sucked her fingers dry.

For weeks it continued and he yielded more each day. She told him to crawl across the floor to her. He did. He felt her press the dildo against his ass and somehow he knew he must let her. She ordered him to kneel next to her while she ate. She called him boy. And one night she smacked him and called him a little slut and the mix of shame and desire he felt welled up in him and made him so hard that he almost burst and single tear slid down his cheek.

Now he sat in this parking lot, wearing pink lace panties underneath his light-tan khakis, with a butt plug shoved in his ass. Every time he shifted in the seat he felt the plug dig in a little more. He noticed he was sweating.
Someone would notice. They would have too. His pants would get wet on the way in and someone would notice. They would laugh and he’d be humiliated.  And of course that was what she wanted. But…it was just coffee and a bagel she ordered him to get. Five minutes in and out…he could handle that, right? His cock was hard and the fabric of the underwear caressing his balls only made it harder to think. If there was one thing he was sure of, it was his overwhelming desire to make her happy. He had to do it. He craved her approval like nothing else he had craved before.
She even toyed with him this morning as she set the trap, right after she got done straddling his face and enjoying another orgasm.
“You’ll do this for me like a good boy, won’t you?” It was a mixture of and order and a coo, said in way that made him want to drive through a brick wall if she told him to do so. She pressed a long leg into his cock as she asked. “You want to please me, don’t you?”
He moaned out loud and she brought the plug and the panties to bed and ordered him to roll over. She rubbed the cool lube on his hole and shoved the plug inside quickly, making him grunt.
Stepping into the panties he got dressed and she rubbed up against him, kissed him and grabbed his crotch before he left. “No umbrellas allowed,” she hissed.

He couldn’t waste anymore time. He opened the door, hiked his pants up and made a break for it, stepping awkwardly between the raindrops to keep the plug in place.

He was breathing heavily and drenched when the door to the shop closed behind him. As he glanced up at the menu, a familiar voice made him jump.

“Hey sexy,” she said in a voice loud enough for everyone in the shop to hear. “Nice panties.”

He froze in fear as he felt his cock go rigid.

To be continued?

By Jeffrey Wordsmith