A Surprising Date

Jake took a swig of his Corona while surveying the bar. All the regulars were there, he thought, but no one new and interesting. But he changed his mind after a second sweep, when his gaze lighted on a cute redhead in a short black dress, sitting alone and sipping what appeared to be a beer of her own.

He stared, unashamedly, and she caught his eyes and smiled. To his surprise, she stood up and sauntered over.

"Hey, handsome," she said. "What's your name?" Her voice was surprisingly deep and rich, like an exotic melody. He held out his hand and she shook it.

"I'm Jake," he replied with a smile. "What may I call a lady as lovely as yourself?"

"Well," she chuckled, "I don't know what you can call any ladies. But you can call me Amy."

"Well then, Amy, to new friendships!" Jake raised his bottle, and she touched her own against it, watching him through long lashes as they both sipped.

She moved closer, a mischievous look on her fine-featured face. "Want to blow this joint? I know a jazz club the other side of town you might like, if you're not afraid to get a little hot and heavy."

He grinned, and leaned even closer, breathing in the smell of her perfume. "Afraid of a cute little thing like yourself? Bring it on, Amy." He winked.

She held his gaze and breathed in, enjoying his manly smell. "I'll even treat you," she whispered. "But fair warning – I'll expect you to put out later, if I do." And with that, she grabbed his crotch, eyes twinkling as she moved her body against his to hide what she was doing from the rest of the bar.

Jake went instantly hard, and ground his crotch against her grip. "I don't think I'll have a problem with that," he quickly replied.

A few more drinks and several dances later, and Jake found himself disrobing in Amy's tiny but tidy apartment. She grinned tipsily, pressing herself against him. "Time for my reward, stud-muffin! Pay up!" Jake pulled her close and kissed her hard, then leaned back to unbuckle his belt and slide his pants off.

She whistled appreciatively as his cock came into view, already standing to attention despite the beer he had consumed. "That's a nice piece of hardware, it sure is," she whispered lustfully. "But tell me what you think of mine."

Jake was confused, until she opened a drawer and pulled out a big, black strap-on, her grin growing bigger as she watched his face. He paused, uncertain how to proceed. He didn't want to ruin his shot with this hottie, but he also wasn't sure he wanted anything to do with that strap-on.

Before he could decide what to say, she was on him, kissing him passionately and running her fingers through his dark hair. His uncertainty faded into the background as his body took over, and her skilled hands soon brought his cock to full readiness. He moaned into a particularly messy kiss, and she suddenly spun him around. Before he could protest, she pushed him from behind and bent him over her bed.

"Now, stud, I can't stop you from leaving," she said from behind him. "But I can promise that if you stay, you're going to have the time of your life." He glanced back at her, thinking tipsily that he should stand, because he was in a particularly vulnerable position. But for some reason he couldn't quite put into words, he stayed bent over while she put on the strap-on.

Her green eyes twinkled as she slathered lube on the black plastic, her hand moving lewdly as if she were jerking off a cock. Then she pressed the tip between his buttocks, and started rubbing his shoulders with her free hand.

"Ever take anything in your ass, stud-muffin?" She pushed the dildo against his asshole to make a point, and he nervously shook his head no. She grinned. "Then I get to deflower you. You'll love it, I promise!"

Without warning, she thrust into his ass, breaking the muscle resistance in one smooth move. Jake cried out in pain, but she thrust deeper, ignoring his discomfort.

"Amy, take it out," he grunted, looking back at her, pinned between her body and the bed. But she looked him deep in the eyes, and pushed harder, causing him to cry out again. He groaned and tried to relax his sphincter, being too tired from drinking and dancing to fight her off. As she continued thrusting, she started to massage his cock, and against all odds, he felt himself growing hard again.

She tickled his balls lightly with her fingertips, and leaned to his ear to whisper. "Reach back and spread those ass cheeks for me, hot stuff." Jake groaned, and did as she ordered.

She squeezed his cock in approval. "How does it feel, spreading your ass for me while I fuck it wide?" She punctuated her dominance by thrusting into him harder, causing him to grunt and moan.

"Now, we can do this one of two ways," she whispered, sliding her tongue into his ear and causing him to shiver. "I can ream your butt until you can't sit down, or I can take it nice and slow, and make you cum with my cock in your ass. Which do you think we should do?"

Jake shivered again. He had never met a woman who could make him feel this way before. "Please," he moaned. "Be gentle."

She smiled. "Okay, stud-muffin. But the ball is in your court. If you want a gentle butt-fucking, you have to do everything I say. Okay?" He nodded.

She slowed her pace, fucking him in long, measured strokes. "Tell me how my cock feels in your butt," she said.

Jake paused to think, and she smacked his ass hard. "Tell me, now!" He winced, and she spanked him again. "It hurts," he told her. "But it feels good, too. I feel like I can't take anymore, but I still want you to make me take it."

She massaged his butt gently, picking up the pace a bit, but still fucking him gently like she promised. "That's my good boy," she cooed. "Now, push that tight little ass up for me, and show me how a good boy offers himself for cock."

Jake didn't even hesitate. He pushed his ass in the air and arched his back like he had seen girls do when he fucked them doggy style. He even spread his ass cheeks again with his hands, offering her a view of his asshole spread around her giant strap-on.

Amy growled, deep in her throat, like a big cat ready to pounce on its prey. "Oh, baby, I love seeing my dick in your ass." Her eyes took on a slightly crazed look, and she began to move faster, unable to control herself as she pounded his butt. "Take it for me," she moaned, as she began to ream his asshole.

Jake grunted and squirmed, but by this time, he wanted it too. He pushed back hard on her, not caring that he was going to be sore for a week after this kind of butt-fucking.

"Fuck me, Amy!" he encouraged. "Push that big dick up my ass, and spank me hard!" They came together, his cum spurting out white against her bed sheets, and her pussy juices flowing down her legs as she fucked him.

She continued fucking him as she shuddered through multiple orgasms, and he held his ass cheeks open for her until she was finished. When she finally calmed down and slipped out of his ass, she smacked his butt.

"Stand up, stud-muffin, and come give me a kiss." Jake obeyed, and she kissed him long and softly. "Let's get some rest," she whispered, "and maybe we can go again in the morning."