Trivia Night

Amanda saw Craig the first evening she walked into 'Salute.' He was clearly a regular at the neighborhood bar, and his group of friends were a little loud at times, but mostly fun-loving. She noticed him right away because he had a bit of a nerdy look. He wore glasses, and he clearly wasn't a narcissistic gym rat. But he wasn't a shy retiring kind either. He frequently cracked the group up with his jokes and life observations. She knew her type and wasn't ashamed of it.

Amanda had moved to the city a few months back, to a new job, a new start. Some of her colleagues at work were also regulars at 'Salute' and had invited her out at the end of her first week. While they didn't know Craig well, Megan had chatted with him some, "he's actually pretty smart, and down to earth" she shrugged, "kind of a decent guy, I think." Amanda and Craig had chatted some over the last couple months and she concurred. As she got to know him, her interest in him grew.

He seemed interested in her too, and they flirted a bit some nights. She kept hoping he would make the first move, although if he didn't soon, she was confident enough to take matters into her own hands. She liked being the one in charge, but many men weren't receptive to that. She had learned to bring that into the relationship gradually, and even then, few men could really accept it.

The bar often held some kind of trivia game. She and Craig were frequently in the top few scorers for individual events and typically one of them was a winner on the team events. They both clearly enjoyed it, and while competitive, they didn't let it get too heated. Tonight's game was billed as the Ultimate Trivia Tournament Challenge. Set up as a double elimination tournament, her and Craig quickly knocked most of the competition out. In the quarterfinal round of the winners bracket they were paired against each other.

"What is the largest grossing film with only women directing it and who directed it?" the MC asked them. Amanda thought and quickly wrote her answer, Craig took a little longer but easily beat the 30 second buzzer.

"The answer is, 'Wonder Woman' directed by Patty Jenkins." The MC called out.

"YES!" gloated Craig as he waved his correct answer.

"Wait," Amanda cried, "I thought it was Frozen II and Jennifer Lee?"

"No, I'm sorry, she co-directed with Chris Buck" came the MC's reply.

Amanda was thrust into the 'loser' bracket. She dominated the next few rounds of the loser bracket and her and Craig emerged as the top two. She had to beat him in two questions, he only needed one.

"What is the name of the first hospital to successfully perform a human heart transplant and where is it located?" The MC asked.

Amanda smiled and wrote her answer. Craig had a bit of deer in the headlights look but he wrote something down and shrugged.

"Groote Schuur Hospital in Cape Town, South Africa is the answer." The MC read.

Craig had guessed Mayo Clinic, Rochester, MN. But Amanda had known this one for sure and all the women cheered.

"Care to make a little wager to keep it interesting?" Craig offered with a wry smile.

Amanda laughed, "what'd you have in mind?"

"How about this, loser has to do anything and everything the winner wants for the next 12 hours." There were some gasps at the obvious implications.

Amanda furrowed her brow and thought for a minute. She knew she was good. But so was Craig. On the other hand, she'd been interested in him for a bit, and it almost seemed like a win-win. She was no prudish virgin for sure.

"OK," she smiled and nodded, "you're on."

Craig laughed, "Shit, I didn't think you'd go for it!"

"If you travel due South from the Renaissance Center in Detroit, Michigan, what is the first foreign country you will cross into?" The MC moved the game forward.

Amanda almost laughed. She loved geography and this was one piece of trivia she knew. Craig furrowed his brow and finally wrote an answer.

"Canada" was the MC's announcement to many puzzled looks. Amanda waved her card with Canada under a drawing of a maple leaf and smiled. Amanda knew it wasn't over yet, if Craig knew this too, it would keep going.

Craig smiled, shrugged his shoulders and showed his card: Cuba.

"Well, I guess I'm all yours tonight, Milady." He said with a flourish.

Amanda's smile was so bright it could have lit a city. "I like that idea. And that's the first thing, for the next 12 hours you call me 'Milady.' You can pay my tab and buy me another beer on yours."

"As you wish, Milady" Craig said with surprising happiness.

They each got another beer and Amanda led him over to a little corner table while they drank them.

Amanda looked at her watch, "So you're all mine until 9am ish?"

Craig smiled and nodded, "That was indeed the bet, Milady. Whatever you wish."

They sat and chatted about their week and their lives. Around 9:30, their beers finished Amanda stood up. "Let's go," she announced, taking his hand. Craig followed along as they left the bar and walked the couple blocks to her apartment.

As her door closed behind them, Amanda turned and began to kiss Craig. She wrapped her right arm around his waist, while the fingers of her left hand slipped up the back of his neck. Craig's arms wrapped around her and pulled her close against him, his lips accepting hers and his tongue teasing and swirling.

Amanda paused the kiss and looked into his eyes. "I have some," she paused, "shall we say 'unconventional' preferences in the bedroom." Surprisingly Craig just kind of smiled, so she continued, "I'm big on consent, and while you lost the bet, I want to know that you're OK with what's going on. I don't want you waking up tomorrow and feeling, shall we say, abused?" She cocked her head and raised one eyebrow.

"I'm OK with it, Milady." He responded with a bit of a wry smile.

"For a minute, forget the bet, we can fulfill that in other ways." Her voice serious. "And drop the Milady for just a minute too. Are you really OK with me using you as I wish sexually?"

Craig nodded and took a deep breath, "I think so, I suppose it depends on exactly what..."

Before he could finish, she jumped in, "So there's a thing called a safe word. It allows you to stop things, no issues or recrimination. For me what works is a stop-light system, 'green' is OK, 'yellow' is I'm feeling uncomfortable with this, 'red' is a hard stop. I'll ask 'OK?' just to check at times, but you can call yellow or red anytime. Will that work for you?"

Craig smiled and nodded, "perfect." And then he continued, "Milady" with a wink.

Taking his hand, she led him back to her bedroom. The waist high four-post king-sized bed against the wall anchored the room, but the spacious room allowed for a large bureau, an armoire, a small vanity table, and a large wing back chair. She positioned him at the foot of the bed. "Close your eyes."

Craig dutifully obeyed and Amanda retreated into the adjoining bathroom after retrieving some lingerie from a bottom drawer. "You can open your eyes now, and I want you completely naked, with your clothes neatly folded and stacked on the chair in front of the vanity. You will stand at the foot of the bed again."

"Yes Milady," Craig dutifully replied.

Amanda donned the outfit she had bought a few weeks earlier. The silky black thigh high stockings were supported by a classic lacy black garter belt. The straight lines of the suspenders accentuated Amanda's generously curvy hips. The black lacy matching bra with a deep scoop highlighted her full breasts. She opted to leave the lacy bikini panties off for tonight, although she wished she didn't have to. It's too difficult to take them off with the garters on, and she knew she wanted them off.

"I'm ready, Milady." Craig called out.

She took one last look in the mirror and decided it would do. She made her entrance to the room as grand as possible by walking with a cat like slink. Both Craig and his cock stood at attention at the foot of her bed. She saw his eyes look over at her and he let loose an audible gasp.

"Do you like what you see?" She said as she took up a position right in front of him, his rigid pole only a couple inches from her abdomen. His excitement and anticipation were evident on his face.

"Yes Milady, you are beautiful and as sexy as I imagined you might be."

"Oh, you've imagined me?" Amanda was quite surprised.

Craig gulped, "Yes Milady." His answer terse, she could see the color rising slightly in his cheeks.

Amanda smiled, "Have you masturbated while imagining me?" His reaction was both immediate and exactly what she hoped for. His face flushed red. "Don't lie to me." She said with some force.

"Yes, Milady." He stuttered.

"Yes to what? Say it." She demanded.

Craig blushed a deeper red. "I have masturbated while imagining you, Milady."

Amanda heard the arousal in his voice and saw his cock twitching slightly. She gently put two fingers on the underside of his rod at the base and began to stroke upward, "And how long do you usually last?"

She could see Craig shuddering and feel his cock throbbing at her touch, his voice stuttering, "a minute...or...two" he gasped out between breaths. Then adding, "Milady."

Amanda's fingers reached the edge of his helmet. "How long is your cock?" She left her fingers there, just barely touching him.

"About..." he gasped, "about six inches, not quite, milady."

"Good boy." She cooed. "I don't like braggards who can't measure."

Amanda turned and crossed the room to the wing back chair. From a basket next to the bureau, she grabbed a towel and spread it on the chair and then sat down and leaned back. One leg crossed over the other, one hand on her knee, and the other on the armrest.

"Come take your position on your knees at my feet." She invited.

Craig quickly crossed the room and knelt at her feet. She liked the way his cock bobbed when he walked and stifled a little giggle at it.

"I assume you've eaten a pussy before, right?"

Craig nodded, "Yes, Milady."

Slowly Amanda uncrossed her legs and spread them out, sliding her ass to the edge of the chair, "Then get to it boy."

Craig didn't hesitate. As he crawled between her legs, his hands came up and gently caressed her thighs. Amanda love the touch and moaned just slightly. He slid his hands up under her ass holding her to his mouth like precious fruit. Amanda let herself just sit back and enjoy the sensation as he placed little teasing kisses and nibbles on the inside of her thighs and the sensitive area just outside of her lips. She could feel herself swelling with arousal and then his tongue slid slowly up her slit. Again, he started at the base and his tongue slid, deeper, spreading her lips. As he reached her clit, he swirled and teased her for just a moment. She gasped.

She let him tease and taste her, feeling her excitement grow. She was grateful he was at least decent at it. He had settled into a slow rhythm, sliding up and down and swirling at her clit, but she needed to control it. Reaching down she slid her fingers into his hair and gripping it forcefully, pushed him against her pussy and began to guide him.

Craig quickly acquiesced to her lead, his hands helping to pull her against him harder. As she began to gasp, he growled into her. The combination of his tongue, her control and the guttural growl sent her over the edge. She came hard. Bucking her hips against him as she mashed his face into herself even harder. She could feel, more than hear his affirming growls and moans.

When it became too sensitive, she pushed him away and laid back against the chair, "Good job boy, kneel there for just a minute." Her breaths coming quickly, she added, "You OK?"

Craig smiled and gave two thumbs ups as he knelt on his haunches, "Green as Green can be."

Amanda smiled as her heart rate began to return to normal. The tension of her desire slaked some, she smiled back, "Then go stand by the bed again."

She enjoyed just watching his naked body as he walked back and resumed his position. His cock, firm and erect, pointed up at an angle that was quite pleasing. She rose from the chair and crossed the room, this time standing just to his side. Taking his cock in her hand, Amanda wrapped her fingers around it. Craig moaned in delight. Amanda loved that sound. She leaned forward and whispered in his ear, "I love it when you moan for me."

Craig moaned again in response, and then whispered, "Thank you Milady."

Slightly louder, "If you get close, you are to say 'please don't let me cum'."

Craig gasped, "Yes, Milady."

Slowly Amanda began to stroke his cock. Her fingers gently caressing and teasing his shaft as she slowly teased and explored it. While he was average in length, his girth was nice. A good handful. She let her fingers glide down his shaft, then uncurling her hand she began to caress his balls. This elicited a sharp intake of breath.

"You OK?" she asked as she stopped teasing his balls.

"Y..yes...erm...green..." he stammered.

Her fingers returned to teasing him and he moaned again. She stood a little closer and wrapped one hand around the shaft, while her other hand cupped his balls. His groans and moans and whimpers excited her. The power to take a man and make him jelly thrilled her. Especially when he let her take charge.

His voice almost a whine it came out in a rush, "please don't make me cum."

Amanda immediately let go of him and took a step back. He looked over at her, his faced flushed with excitement, his eyes desperate, his cock pulsing with his arousal.

"You are not going to cum until I give you permission. You will keep begging me not to cum until I decide you're ready. Do you understand?" Her voice soft, sultry, and leaving no room for discussion.

"Yes, Milady" his words breathy as he fought for control.

Amanda stepped in front of him, and gently touched the bottom of his scrotum with her index finger. His cock throbbed at the sensations, and he moaned again. Slowly Amanda let her fingertip slide up the underside of his cock. She loved how it twitched at her touch. As her finger reached the head of his cock, she could feel the slick precum. She circled his head slowly, her finger smearing the pre-cum and teasing the sensitive tip.

He was now whimpering, fighting to keep from cumming, "please don't make me cum," he finally gasped.

Again, Amanda withdrew her finger. Leaning forward, she kissed him, gently at first and then with increasing ardor. She carefully stayed away from even brushing his cock. After a moment, she stepped back. His eyes locked on hers. His face radiated his desperate desire for her and for release. She smiled.

"Turn around and face the bed." she commanded. As he turned, she walked backwards toward the bureau. "Spread your legs, a little wider than shoulder width." She added when he faced the bed.

She opened her dresser drawer again and withdrew a small butt plug and lubricant. "Close your eyes, bend at the waist, resting only your head and shoulders on the bed."

Craig dutifully obeyed, his ass now on full display for her. She took the few steps back to him and standing next his torso, she squirted a generous amount of lube on the toy.

"This may be a little cold," she warned as she also squirted some into the crack of his ass. He gasped slightly. Amanda set the lube down on the corner of the bed.

"Keep your eyes closed. I'm going to insert a butt plug into you, are you OK with that?"

"Yes, Milady." He replied.

"Green?" she asked for clarification.

"Yes, Milady, green."

"Have you ever had a butt plug in your ass?" she asked as she used one finger to gently massage the lube around his tight little hole.

"No Milady." She could hear the blush in his voice.

"Have you ever put anything in your ass?" She asked, now just barely slipping a single finger into his ass.

His voice wavered with slight embarrassment and excitement, "Yes. Milady." His rapid breathing as her finger slid deeper into his ass.

"Tell me what." Amanda encouraged Craig with a tone of slightly exasperated expectation.

She could hear the embarrassment in his voice, "The handle of a spatula."

"Did you enjoy it? Did you masturbate?" Amanda's finger slowly relaxing his ass as it slid in and out.

"I did masturbate," he paused, "more than once. Yes, I enjoyed it. Milady." His voice betrayed embarrassment and yet a tinge of arousal seemed evident too.

Amanda positioned the butt plug at his entrance and slowly pushed, "Push out a little like you're trying to poop." She felt his sphincter relax and the plug entered him. Craig gasped again. She loved the view as the plug first stretched his ass and slipped from sight, except the handle.

"Crawl up onto the bed and lie on your back, your knees spread and your feet together." Amanda grabbed a towel from the dresser again as Craig positioned himself, wiping the lube from her fingers. Setting the towel on the foot of the bed, she climbed onto the bed and lay down next to him on her side. She propped her head up on her arm and looked into Craig's eyes. "You look so amazing all spread out for me." His smile made her beam in response.

She noted that his cock was less stiff than before. She knew it was often the case that men would go soft when something was inserted in their ass. Returning her eyes to hold his gaze, she wrapped her fingers around his semi-rigid cock and began to tease and stroke him.

"Do you like having something in your ass then?" She cooed.

His face blushed again as he whispered, "Yes Milady."

She could feel his cock hardening in her hand. She loved the feeling of control. It excited her to have the power to make his cock do what she wanted. She loved taking his ass. She almost wished he'd never tried it before. She let her fingers slide down, cupping his balls and then gently rubbing his cock with her palm.

Her eyes wandered up and down his body. She would hold his gaze for a moment and slowly look down at his cock. Out of the corner of her eye she could see him watching her. His breathing increased and she could see the flush of excitement on his skin.

"Please don't make me cum, Milady." Craig repeated. This time Amanda didn't stop. She continued to stroke and tease him.

"Don't you dare cum!"

Her gaze now focused on his face, she saw him begin to close his eyes, "Look at me!" Her voice commanded. "Don't you dare cum!" She ordered again as her hand continued.

"Oh please don't make me cum" his voice now desperate.

Amanda let go of his cock. "Good boy, but don't ask for it unless you really need it."

She sat up, kneeling next to him. She put one hand on his knee and slowly drew her nails up his leg, just barely scratching the soft sensitive skin of his inner thigh. He let out a low moan. As she reached the top of his thigh, she gently grabbed the base of the plug and pushed it in just a little deeper. Releasing the pressure, she then pulled it, watching as his skin started to stretch. Then releasing it again. Craig's whimpering moan induced her to tease his ass with the toy for another moment.

She moved a little closer to him and then twisting, she straddled his chest facing his feet. She slid back a little further, raising her hips just enough to allow his face under her. "If you need me to stop, tap me three times," her voice thick with arousal. She let herself down until she could feel his face against her ass and pussy. "Eat me," her desire so strong, "eat me until I cum."

Craig's tongue began licking her. She could feel his nose pressed into her ass and almost wished it would enter her there. His tongue lapped at her pussy. He wasn't as adept in this position, but the feelings of power and control excited her more. She ground her face on him and he responded with vigor as his tongue darted and pushed at her.

Amanda closed her eyes and focused on the sensation of Craig's face buried in her pussy. She twisted and angled her pussy, forcing his tongue to the spots she wanted. She sat up slightly, forcing his tongue to her little rose. His tongue stopped for a moment and she hissed, "lick my ass."