Field Trip

"Wine, miss?"

The young woman at his elbow smiled obsequiously at his dining companion, displaying a bottle of the vineyard's special reserve Malbec. Ava quirked an eyebrow in question, and he gave a slight nod.

"Yes, thank you." She lifted the glass, breathing in the subtle undertones of black cherry, and took a small sip. Her eyes briefly closed in enjoyment, and she gave a soft sigh of pleasure -- the only one she'd be allowed during dinner. The sommelier filled the headmaster's glass and returned to the kitchen, bowing slightly as she backed away from the table.

"You must have dinner here often if they didn't even ask for my ID," said Ava, noting the deferential attitudes of the wait staff.

"They don't let anyone in who's under 25 - I cleared you ahead of time with the school's copy of your license. Besides, I'm the owner."

Her eyes widened in surprise, and the corner of his mouth quirked up in amusement. The young women at the academy revered Joshua Mason, their headmaster and guide, but he had a sneaking suspicion most of them didn't think much about what he did when he wasn't running things or taking a direct hand in their training. She recovered quickly, smoothing the hem of her short skirt.

"It's a lovely place -- I'm so honored that you chose me for the field trip."

"You deserve it. I know I don't get to work with you directly often, but it doesn't mean your efforts go unnoticed." He began ticking off points on his fingers; "top of nearly all of your classes, perfect attendance, and glowing recommendations from all of your teachers, especially when it comes to oral exams."

She blushed, though he wasn't telling her anything she didn't know. She slid slightly closer to him as she shifted in the booth, and he thought perhaps it wasn't his words reddening her cheeks. He leaned in to test this suspicion, sliding his hand up her thigh, grazing the bare skin above. She was soaked. He pulled back his hand and ran a finger over her lips, smiling in approval as her tongue briefly flicked at the tip, tasting herself demurely.

"You know this evening is a reward, but you should know it is also an evaluation of some of the skills you've acquired in your time at the academy."

"Oh -- what skills?"

He shook his head. "The point is to see how well you think and react in uncertain circumstances -- you'll have to determine what I want from you and do your best to accommodate. Fail, and you'll be spending time in the nine-inch heels in the draftiest classroom I can find. Pass, and you'll be getting a very special treat after dinner." Gratified to note both the anticipation and determination in her answering gaze, he leaned closer. "The test begins now."

As the head waiter approached the table to take their order, his hand returned to her dripping center, rubbing his thumb in circles over her clit. Her breath quickened; her jaw briefly clenched against whatever moan of pleasure was threatening.

"I'll have the chicken marsala, and the roasted potatoes," she said. Aside from the fact that the last word was a bit breathier than her normal voice, she gave no indication of what was happening beneath the table. He slid a finger inside of her, curling it toward his thumb as she gave her drink order. He continued to stroke as he gave his own order, feeling her tighten around him, and watching her lower lip gently quiver. As the waiter walked away, he pulled back, denying her the climax she had nearly reached. He knew she was disappointed, if not surprised, but she simply slipped a roll from the basket on the table and began to butter it. He was impressed -- and he didn't impress easily. It was time to move to the more advanced portion of the test. While she was focused on her food, he unbuttoned his pants and slipped his cock free, the head grazing against the underside of the table cloth.

As though she could sense it, she suddenly abandoned the bread, staring intently at him, trying to determine what was coming next. He was curious to see how she would proceed. In years past, many a student had attempted the "oops, I dropped my napkin" oral technique, and while he enjoyed their efforts immensely, he hoped she would be a bit less pedestrian in her response.

He was not disappointed. Her hand slid around him in a soft, yet firm grip, and he realized she had first fingered herself, using her own wetness and the drop of precum on the head of his cock to ensure the expert friction of her hand would be fully pleasurable. She moved up and down the shaft, occasionally stroking the back of her fingers against his balls as she reached the base. He had never been so grateful for the longer wait time required for the dishes they'd ordered. When the waiter came back with their food, she increased her speed, and he felt himself nearing completion. She clearly noticed, and as she leaned forward to grab the salt, maintaining eye contact with the waiter, she turned so that the back of her skirt draped over his cock in her hand, lowering to rub against it as his cum shot onto the curve of her ass.

She sat back down, deftly adjusting her skirt, a self-satisfied smile on her face. He knew she must be dying to know how well she'd met his expectations, but she ate quietly, waiting for him to initiate the discussion. As their plates were cleared, he finally satisfied her curiosity.

"Exquisite."

"The meal? Yes, everything was delicious." Her eyes sparkled in amusement, matching the coy smile on her face.

"What was delicious was your perfect innocent act while I was coating your ass in my cum. I'm clearly not the only one at this table with impeccable self-control."

"Thank you, headmaster. I credit my thorough instruction from you and from all of my professors."

"That's admirable of you, but I'm willing to bet that your natural gifts when you enrolled were more ample than you're letting on. I intend to explore that theory now."

"Sir?"

"Come with me -- I promised a reward." He stood and offered his hand, pulling her up and placing his hand on the small of her back. He guided her toward the back of the restaurant, nodding to the bartender and maître d as they passed. They came to a heavy oak door, and he slid a key from his pocket. The door opened silently onto a staircase that curved down to the next floor. She moved forward unquestioningly, her heels clacking gently on the polished wood, hand sliding along the bannister.

"Oh!" she gasped as she reached the bottom, gazing out over the vast expanse of the softly lit wine cellar. Wooden casks and shelves were arranged artfully around the walls, interspersed with candle-lit alcoves. At the far end, a supple leather couch on a plush rug gleamed in the light of a marble fireplace. A carved cherry-wood bar stood to the side, a small box sitting on one of the stools.

"Welcome to my other office," he said, gently applying more pressure with his hand and steering her toward the couch. He motioned for her to sit, gazing admiringly as the combination of her high heels and the low couch tilted her hips up to gift him with a better view.

"This couch is absolute heaven," she breathed, sliding one perfectly manicured hand over the arm. "If my reward were just to sit on it, I think I'd be perfectly happy." Though as she said it, she slid forward toward him, ensuring that her skirt pulled even higher, the satin straps of her garter belt now fully visible.

"You might be. But I want only the best for my star student -- and the couch isn't the most pleasurable thing in this room. Stand up facing the couch and close your eyes."

Her composure slipped slightly, and she licked her lips as her eyelids reluctantly shuttered her view of the enticing bulge under his zipper. He could guess what she was thinking -- she'd been rewarded with the opportunity to suck his cock at last month's assembly, and she was eager to do so again. But that wasn't her reward either. He moved to the bar, lifting the lid of the box and pulling out a small velvet pouch.

"Strip." Without opening her eyes, she stepped out of her skirt and unbuttoned her blouse, revealing an open-cup bustier embroidered with intricate patterns between the mesh panels that barely concealed the tantalizing flesh beneath. The chain in his hand winked in the firelight as he placed the clamps on her pert nipples, and she bit her lip to stifle a moan.

Once they were in place, he undressed, moving behind her and sliding his hands down the thin fabric while she stood, unmoving. The model of the academy's standards -- full composure at all times. He leaned in closer, brushing his lips against her ear as he tugged lightly on the chain.

"Your reward is twofold. And the first part is this -- the wine cellar is soundproof. I want you to forget your training for now so I can enjoy your screams for the second part."

With that, he bent her forward over the couch and thrust into her, reveling in her dripping, warm pussy as her muscles tightened around his cock and she pressed her hips back toward him. He slowed, pulling back until just the head was inside of her, then thrust again at full force. She cried out, gasping as he increased his pace, gripping a handful of her hair and pulling her back against him. She stiffened, legs twitching as she came in a gush that covered him.

He took advantage of her weakened limbs to turn her and push her to her knees, where she eagerly sucked herself off of him, moaning with pleasure. He picked her up and laid her on her back on the warm leather, placing her heels on his shoulders. She looked into his eyes adoringly as he slowly pressed into her ass, slick with their cum. She closed her eyes and groaned, arching her back and futilely grasping for purchase on the couch cushion.

He grabbed one flailing hand and pressed it between her legs. She needed no convincing, and began stroking her clit as he slammed into her, faster, harder. She came again, and he pulled back, gripping himself and covering her face as she opened her mouth to catch as many of the cascading droplets as she could.

"Get dressed," he said, pulling on his own clothes. "But don't clean up -- I want everyone back at the academy to know exactly what a good girl you were."