Trivia Night

Tentatively at first, Craig's tongue teased at her back door. She could tell she was pushing his limits and it excited her. "Good boy, lick that little rose" she cooed.

Craig's enthusiasm began to return, and Amanda slipped a finger down to her clit, teasing herself too. The feelings of pushing him, of her power and control, of the naughtiness, brought her second orgasm. She fell forward, her clit now solidly on his mouth, and clenched her knees around his chest. "Oh fuck yes," she cried.

Her orgasm swept over her in a moment. Catching her breath, she lifted off his face, "you OK?"

"Green!" his answer enthusiastic. "Did you like it, Milady?"

She smiled, "Yes, but we'll talk later. I want you to resume your bent over position at the end of the bed." Amanda swung her leg over and then slid off the bed. She crossed the room again to her special drawer. As Craig positioned himself, she added, "And close your eyes."

From the drawer she retrieved her most prized toy. A harness with a cute little pink dildo and built in vibrator. She'd never used it before -- except in self-play -- and her excitement at this opportunity was making her slightly giddy. She slowly and carefully stepped into the harness. The feeling of power as she pulled it up over her bare wet pussy was arousing and heady. As she tightened the straps, she looked at Craig, bent over, legs spread, waiting for her. She wondered if he knew or guessed.

She crossed the room, the feeling of her pink little cock bouncing against the harness almost made her giggle. She wondered how men dealt with it.

As she reached Craig's bare ass she started caressing it with her hands. Craig sighed with pleasure. Amanda reached over to where she had left the lube, glad it hadn't been kicked off the bed. She squeezed just a little onto Craig's hole. He gasped in reaction to the cold.

"Sorry, I'll remember to warm it better next time." She apologized. "I'm going to remove this now," she gently pulled on the base of the plug. As she increased the pressure, she saw Craig relax and his ass spread out over the toy. Once the thickest part passed through it came out effortlessly. Reaching around Craig, she grabbed the towel she'd left on the bed earlier, and wrapped the toy inside it, setting it aside.

"Now turn around and open your eyes." Her voice more a request than an order. She saw Craig's eyes widen, and a slight smile spread on his face as her lady cock came into view. The bright pink cock contrasted nicely with her black lingerie and harness. She grabbed the base of it and looking right into his eyes she hissed "I want to fuck you with this."

Craig's cock throbbed, "Yes, Milady." His voice shaking with arousal.

"Climb back on the bed and position your sexy ass at the edge, on your back, facing me." Her excitement led her voice to rise higher than she intended. As Craig positioned himself, she grabbed another towel. Craig had propped his head up on a pillow, and was holding is legs up and spread out, his ass at the edge. She slipped the towel under his ass and picked up the lube. Squirting a little onto her two fingers she warmed it before slowly massaging it into his ass. Her two fingers slipped in easily.

Amanda added more lube to the silicone dildo and wiped her fingers on the towel. Stepping forward between his legs, she lined her lovely little pink cock up with his ass and slowly pushed into him. Her head spun with the excitement of taking him like this, especially his willingness to give himself to her. Her eyes darted back and forth between his face and her dick sinking into his ass. Craig's slight moan, and the twitching of his cock just added to the excitement.

As Craig's ass took the toy, she stopped and took a breath. Looking into his eyes she could see that he was enjoying the view. Amanda leaned against him slightly, balancing against him on her hips. She then unclasped her bra and let it drop, exposing her breasts to him. She saw him smile slightly. It turned her on to know that he enjoyed seeing her tits. She then reached down to the little pocket on the front and pushed the button to turn on the vibrator.

As the sound and vibration hit Craig he gasped, his head tilting back. Amanda gasped herself. She knew the toy was strong, but she had never been this excited when she first turned it on. She reached out and took his cock in her hand again. Setting her feet one slightly in front of the other, she began to slowly fuck his ass. They looked straight into each other's eyes holding their gaze as she fucked and stroked him. "Remember not to cum" she gasped.

"Yes," gasp, "Milady." He was struggling with control and was overwhelmed himself.

Amanda's pace picked up slightly as the vibrator worked it's magic against her clit, but she knew the real excitement was from the vision of this man spread out in front of her, taking her pink dildo in his ass. As her orgasm neared Craig moaned and then practically begged, "please don't let me cum." She let go of his cock and grabbed his thighs for leverage.

Thrusting faster and harder than she had yet, she moaned, "I love fucking your ass, but don't you dare cum."

And then Amanda came. Her hips bucked into him and she mewled, "Oh fu-u-uck." Her body convulsed and she cried, "oh god" over and over. She saw Craig through her haze desperately trying to fight off his own orgasm. His cock oozed pre-cum.

Slowly she gained control of herself and shut off the vibrator. She let go of his thighs, backed up and slid the pink cock back out of Craig's ass. For a few minutes they each caught their breath and Craig fought down his excitement. Finally, he begged almost whining, "Please, Amanda, I need to cum." He quickly added, "Milady."

She smiled broadly, "Oh yes, my good boy, slide yourself up because I'm going to ride you so hard."

Amanda unstrapped herself and wrapped the toy in the second towel. She quickly grabbed a condom from her drawer and brought it over. She climbed onto the bed, and kneeling next to him unrolled the condom onto his throbbing cock. Even that attention had Craig straining to control himself. She loved the sight of him struggling for her.

Straddling him she lined up his cock and sat down, taking him deep inside her. She started riding him, grinding her hips as she leaned forward, supporting herself with her hands on his shoulders. Even with the condom to reduce the sensitivity, it only took a few strokes. She felt Craig buck against her as he gasped, "Oh fuck yes."

As she felt his climax wane she slowed her movements, holding him inside her still. His eyes opened and looked up at her, "Thank you, Milady" the relief evident in his voice.

Amanda smiled broadly, "You've been a good boy." She slowly lifted off him and lay down next to him. And then she kissed him. Gently, their lips brushing and slowly melting into each other. The excitement waning, she felt a deep satisfaction and now a little worry that he would leave her after the bet was over.

As they broke their kiss, Craig took his hand and gently caressed her arm, "That was spectacular."

Amanda's heart soared. "Really?" She asked, both surprised and almost desperately wanting it to have been just as good for him.

"Oh God yes," Craig gushed, "It was great. Was it as good for you too?" There was a kind earnestness to his question that touched Amanda deeply. She could only smile and nod.

They showered together, too spent to do much other than kiss and caress. They slid into bed together and Amanda set an alarm for seven the next morning.

"Why set an alarm?" Craig asked.

"I want my last two hours" Amanda said as she snuggled up to him and he wrapped her in his arms.

When the alarm sounded they both groggily got out of bed. "So, what do wish for these next two hours, Milady?"

Amanda smiled, "Breakfast! There's a lovely little bistro around the corner; you're buying."

Craig laughed, "Anything you wish, Milady." His smile was somehow happier than she imagined. It made her hope that perhaps they wouldn't simply part ways at nine.

They sat in the bistro, chatting over breakfast. "Where are you from?" Amanda asked.

"Oh I grew up in Detroit and then kind of all over for a couple years, until I landed here about a year ago."

Amanda looked at him in shock. "How did you not know that Windsor was South of Detroit?"

Craig laughed, "Well, perhaps I threw that one. I didn't want to waste time. I wanted the twelve hours to start as soon as possible. And I kind of was hoping you'd win."

Amanda smacked him on the arm, "Don't ever throw a game again!" She laughed. And then she cocked her head. "So, what happens at nine then?"

"Whatever you wish, Milady. But I'd like us to see if there's more than just a bet at play here." And then he looked at her with such hope, "because there surely is for me."