Education of a Jezebel Pt. 05: Upper Classman

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* Education of a Jezebel

* Part 5 - Upper Classman

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This is part of a novel. Previous parts should be read first.

Chapter 14

After the requisite debrief of their private lives on Monday morning - Samantha had entertained the crowd in a pile of women, then been the filling in a threeway - they got down to business. The weekend of tours was only five days away, and although by the standards of previous years they seemed on top of it, they both knew there would be a crisis or two, unexpected details to handle. They both worked late into the evening on Monday and Tuesday, then suddenly, the calm at the eye of the storm overtook them, there was nothing to do. They couldn't leave the office, just in case, so the three girls sat and gossiped.

Relaxed and smiling, Kelley was home by 5:45, she made a salad, warmed some artichoke dip. She was flipping through her romance novel after the sun set when her phone screen lit. "Hey, I wondered where you went to," she said to Kurt.

"It's only been four days," he laughed, "and you told me you'd be really busy this week. Other guys?"

"You know I'm swamped with work. But it slowed down today, I'm just relaxing tonight."

"Well, maybe I should help you relax," he offered.

For a second, the remnants of Kelley's conscious peaked over the wall, she pushed it firmly back. "Yeah, sure. I usually relax by cleaning my kitchen, you can help by scrubbing the pots."

Kurt's chuckle was lovely. "Okay, half an hour."

Hurriedly, she picked up the magazines on the floor, didn't worry about the film of dust she hadn't gotten to in a couple of weeks, ran to the bathroom and swabbed her dirty spots, then found a babydoll that had been one of Luciano's favorites; she didn't think she'd ever worn it for Andrew, that made it a little special.

After she'd let him in, Kurt gave her the once over. "You clean your kitchen in that?" he grinned. Her lingerie cupped her breasts and tied at the front, the hipsters had a lace panel at the waist, the transparent costume hid nothing, promised everything.

"What else would a girl wear? Want a drink?"

"Got any bourbon?"

"I think so. Whiskey for sure." He followed her into the kitchen, watched her pour three fingers of Jack, a snifter of Chambord for herself. In the living room they shared their first kiss standing up, he led her into the bedroom where five or six candles burned. "Again, nice," he complimented, "I didn't see much of it the other night."

"Oh," she teased, "what were you looking at then?"

"Nothing, it was dark. But I was feeling this." He turned her around until she was facing away from him, reached around and untied the lingerie, grabbed a melon.

She twisted away from him playfully, moved to the other side of the bed. "I stripped for you the last time, it's your turn," she demanded.

He clumsily complied, although the song on the speaker had a medium tempo and he had no sense of rhythm. But he toyed with his shirt, his pants. She could see he was already hard for her, even inside the briefs. "All of it," she required.

Soon they were on the bed, the boob was kissed, the cock sucked. Kurt manipulated to a spot below her, she raised her knees and spread her thighs. She was anticipating this, had been wanting it ever since she answered the phone. She willed herself to relax, her arms went limp, her neck rested, her breaths were deep and easy. She felt the first brush of his tongue on her lower lips, the clit. Kurt was good at this particular ploy, he toyed with the outside of her sex first, when he heard her respiration deepen he probed inside the channel with his tongue and finger. By now, he knew where her g-spot waited, he used a knuckle to anger it, he felt the shifts of her body in preparation for explosion.

He backed off a little, he wanted to make her wait for it. "This is okay, isn't it?"

She laughed heartily, "Come on, I'm close," she begged.

"Okay." He stuck his left index finger in his mouth, spread spittle over it. With his mouth and right hand he returned to his work, her gasps quickened, he played with the rectum with the wet finger, penetrated it softly. Of course this set her over the edge, he worked her with his mouth and two fingers as she screamed her orgasm. Eventually she let herself down, clamped her legs against his ears, he retreated.

"That was good," she praised. "What do you want?" She expected him to name a position, screw her.

Instead, he said, "Nothing. Not right now, I'm fine." He took a long sip of his drink, so did she. "Do you have any massage oil?"

"Umm-hmm. In the drawer." He poked around in the side table, inventoried her arsenal. It had everything a girl needed for bringing herself off, no whips or blindfolds or anything particularly strange though. He found a box of five different oils. "Luciano got it for me one Valentine's day, then he got drunk and just went to sleep. It's got to be a few years old, I've never used it."

He read the various descriptions, chose the one that had fragrances of 'rose, jasmine, and sandalwood.' "On your stomach," he ordered, she complied. He climbed over her, a knee on both sides, squirted the fluid in his hand, warmed it. He started at her shoulders, used deep, hard strokes, worked his way down her back.

"Oh, that feels so good. It's been so stressful..."

"Shhh. Just relax."

He continued to work his way down, the small of her back, the gluteus muscles, and, slowly, waiting for any sign of disapproval, into the crack of her ass.

Kelley sensed what was happening, wondered if she should halt it. But she was feeling so good, and it seemed Kurt wanted this. Samantha had given her a few pointers about anal, it was something every guy wanted to do she'd explained. Okay, might as well let him at least feel me, it wouldn't hurt...

When she didn't object, Kurt poured the liquid directly on spot O, used two fingers to spread it. Gently, leisurely, he prodded a finger past the taut hole, he was inside, one knuckle, then a full thirty seconds later, another knuckle, until finally the whole digit was inside her.

"You okay?" he asked.

"Yeah... it's nice."

Kurt stretched, reached into the drawer for a tube of lube. When Kelley saw him withdraw the smallest dildo, she knew what was coming. Should she object? But why, the finger felt nice, how would the selfie stick feel? She said nothing.

She waited a few seconds, heard the slurp of the lube bottle, then the plastic rod was touching her anus. She tensed, of course, not sure what it would feel like.

"Relax," he suggested, "spread your legs."

Almost as if a dentist had asked her to open wider, she gave in. The pressure increased, she felt it enter, and then it was inside. How deep was it, she wondered, and when Kurt began the in and out movement, she found it was actually pleasant, even good.

Kurt kept an eye on her, he was pretty sure this was the first time she'd ever had anything up her ass, and he enjoyed the sighs of her contentment. A few moments later when he felt her twitch, he slowly withdrew the plastic.

When they were side by side, kissing, she revealed, "That was nice. If you want to do it to me again, sometime, let me know." She really did think it was lovely, not particularly gross. And she wondered, perhaps, if another cudgel had been added to her arsenal to be used when Kurt or another of his cohorts weren't at hand.

A flick of her wrist alerted her that his little boy needed to be resuscitated, she wriggled down the bed, her legs out to the side, her head over his prick, she slurped and kissed at it, reviving it back to a useful state.

As she blew him, he held one of her gorgeous puppies, twitched a nipple, pulled a leg and as it came closer to his ear, used a finger to tickle the clit, prod into her crevice. Wondering if she was still in the mood for it, he let his hand wander up past it, approach the rectum again. He wasn't really surprised when she lowered her belly slightly, she was obviously encouraging his finger to play with the sphincter.

Kelley's art had encouraged the prick sufficiently, it was ready for action. He was at least two knuckles inside the back hole, she understood what he might like, and she was surprised she was in the mood for it, too. She released the tool from her mouth, softly asked, "Would you like to... back there...?"

"If you want me to," he assented.

"How should we do this?" she asked. "You know I've never done that, right?"

He'd thought so, of course, he didn't think Andrew ever would have asked for it, and Luciano seemed like a real dick. He was honored by her offer, took charge.

He laid her on her stomach, put two pillows under her belly. He kneeled between her knees, lubed himself well, and spread it liberally over her brown rosette. It had been a couple of years since he'd had anal sex with anyone, not since Amanda had stopped letting him come around; that girl would do anything, a total slut! He tried to remember the tricks.

He rubbed his dick up and down her ass crack, from the small of her back all the way down until it was almost at her pussy, then back up, pointed it at the back hole, pressed lightly. Of course she tensed up, of course he told her to relax. Through the first few pushes the breach refused to yield. "If I'm hurting you, let me know."

"No, I'm fine," she bewailed, "go ahead."

Another long push, the barrier yielded. He tried his best not to push in too quickly, but considering how slippery the piston and cylinder was he may have been a little quick. He heard her grunt loudly. "I'm okay," she whimpered, he began his thrusts.

She was surprised it didn't hurt, exactly, she just felt extreme pressure as he screwed her ass. In fact, once the initial shock wore off, it was almost pleasant. Not as much as in the other hole, but not bad at all. She relaxed, let him work at the chore. Yes, she could see how you might, conceivably, have an orgasm this way, it would take practice.

Kurt was over the moon, watching his sword disappear within the virgin ass, it was as tight a hole as he'd ever been in. "I can't hold it much longer," he warned.

"Go ahead, I'm ready." And the white cream flowed like a shot into the alternate channel. Kelley understood what was going down but had no control over it, it was something that just happened to her.

When it was over he pulled out, looked at the brown ring covered with his buttermilk. For years afterwards he regretted that he hadn't got his cell phone to take a picture, the only virgin canal he ever had, ever would have.

Kelley rose, headed for the bathroom, he heard splashing, when she returned she had a wet cloth, she cleaned and dried him. "Well, that tears it," Kelley sadly said. "Now I'm only a virgin in one spot."

"Where's that?"

"My left ear."

"We'll take care of that next time!"

Kelley sipped at her drink, Kurt drained his. "Can I get another one?"

"Sure, you know where the bottle is. I'm your whore, not your maid."

As he strode into the kitchen, he wondered about the word. Returning, he said, "You know, I don't think you're a whore."

"It was only a joke." They cuddled.

"So, tell me," Kelley sighed. "How'd you get so good?"

"You really want to know? When I was nineteen, I was working a summer job as a landscaper. The boss sent me over to this one place by myself, the wife invited me into the house for a drink, yeah, she seduced me, not that I resisted very hard. She told me I was pretty good, gave me her phone number.

"I was over there a few times a week, mainly in the evenings. Her old man knew all about it, he even watched us a few times. She liked that my cock was so hard, but she wanted me to do other things, she kept telling me she wanted this, she wanted that. Nicely. It was almost like a seminar with a lab, I learned a lot.

"So," he finished, "you're learning the ropes. Do you believe that six months ago you were still pretty much a virgin?"

"Sometimes I wonder how it happened so fast."

"And you're gonna get better, I know. So when you're forty, it's gonna be your duty to train a nineteen year old boy."

"I'll remember that," she laughed.

It was just a little after ten, but she said, "I'm kicking you out. I've got a big day coming up, need my sleep."

"Okay." He began dressing. "So, want to get together this weekend?"

"I won't have any time. I've got to be downtown by seven o'clock Saturday and Sunday, Saturday we've got a dinner for the donors, Sunday it's the volunteer party. I'll be tired, I'll be grouchy as all get out. You don't want any of that."

He kissed her goodbye on the way out, she was still naked. "Hey, this was my first booty call, too!" she chuckled.

"What a night," they both laughed.

"Call me next week," she requested, "let's have some more booty!"

Chapter 15

Thursday and Friday went by, periods of calm, periods of chaos, she and Sam were constantly waiting for a bomb to drop, none did. Luckily, the weekend forecast was for sunny skies and warm temps, great weather.

At 6:50 Saturday morning she was in Central Square, Jonesy was actually waiting for her. He was an older, retired guy, a longtime volunteer for the organization. He seemed to live for this weekend, last year he'd been volunteer of the year. They chatted over coffee and doughnuts until the truck arrived, ten minutes late of course. The vendor erected the tent, furnished it with folding tables and chairs. Kelley and Jonesy pulled the brochures and tickets from the truck of her car, spread the banner, 'OpenedDoors', over the tent. By 8:30 all was well,

At nine, volunteers started showing up, she and Jonesy and Sam dispatched them to the buildings they were assigned to, a couple of hiccups such as volunteers who couldn't make it popped up, they were corrected easily. For a pretty big task, it went relatively smoothly.

And at ten, the rush started. People approached the tent, bought tickets, needed information, this was the purview of Jonesy and his crew of four. Kelley and Sam started out on an inspection tour of the twenty nine buildings, needed to make sure everyone was at their post, no problems cropped up.

For the rest of the day, Kelley flitted from here to there, making judgement calls, yakking with volunteers and visitors. Samantha's job was to court the donors, the property clients, keep them complacent, this was her biggest talent.

When Kelley returned to Central Square after three, Jonesy gave her a message. "There was this guy here looking for you. He wanted your phone number, of course I wouldn't give it to him. But he left his number."

'Hmmm,' Kelley thought, reading the note, seeing the name 'Clark.' "Thanks, Jonesy." She pushed the message into her purse, had no time to call him.

The thing started wrapping up around four, from 4:30 to 5:00 the building volunteers had returned their kits to Central Square, by 5:30, the tent was all locked up. "See you tomorrow, Jonesy! Thanks for being here, we couldn't do it without you."

She drove home, rested for just forty minutes, then poured herself into the shower then her gown, headed back downtown for the Donor's Ball. It started at eight, both she and Sam were in the ballroom by 7:30, supervising the caterer and the barkeeps, making a change here, a tweak there.

The event was a typical society ball, supposedly dignified men in suits or tuxedos, their wives in luxurious garments, jewels dripping, auras of egos displayed for their peers. Kelley, looking young and fresh for this crowd, was fawned over. More than once her ass was 'accidentally' fondled, her bosom was bumped into. It was what she expected, only once was she seriously offended when a sixty eight year old lawyer whispered a very indecent proposal into her ear.

The buffets and pasta stations were busy until around nine-thirty, the barman said they were running out of the preferred whiskey of the season, there was nothing to do about that, of course. "Try to keep them happy," Sam advised.

In a quiet moment after ten, when the thing was starting to wind down, Kelley was approached by a man. A little over six feet, suit of navy silk, the tie should have been called a cravat. This was his first year at the ball, she thought, she didn't remember him from previous events.

"Hi, I'm Thomas Ainsley."

"How are you, Mr. Ainsley? I'm Kelley Nestico."

"Oh, call me Tom. You put on a nice event."

"Well, thank you."

"You're the executive director of OpenedDoors?"

"No, that would be Samantha, over there." She pointed. "I'm Director of Event Planning."

"Ah..."

She found he was a Director of a division at USPG, one of the largest companies in the city, the reason she hadn't bumped into him before was that he'd been a manager at the London office until the previous autumn. Ah, that explained the suit. He was certainly flirting. She didn't flirt back, of course, this was not a place or time to do so. Well, at least she didn't flirt much.

"I don't suppose you have a business card, do you?" Tom asked.

"Of course." She produced one from her clasp.

"And I don't suppose you'd write your cell phone number on the back, would you?"

She smiled. So it was an attempt at a pickup! "I couldn't do that, Mr. Ainsley, as I'm sure you understand. But, if you invited me to lunch, maybe you could talk me out of it then."

He grinned. He was good looking, a full head of light amber hair, intelligent eyes, great teeth. "Well, I'll just hope I can be persuasive enough then. Good night, Ms. Nestico."

"Good night, Mr. Ainsley." She watched his cute ass stride away, wondered if anything would ever come of it.

By eleven, Kelley and Samantha were having their second drink of the night at a table in the deserted ballroom. Kelley had nursed glasses of champagne all evening, Sam was sober as a judge. They compared notes, who had promised donations for next year, who had indicated there was a small problem. "Okay, see you in the morning," Sam said, after they'd walked each other to their cars.

Sunday was much the same, except the after tour party was at 5:00 in a hotel lobby, each volunteer had two drink coupons, the buffet was quesadillas and dogs in blankets rather than lobster and sushi. By the end at seven o'clock, Kelley was sick of smiling, saying thank you, and being hit on by men who were either married, too old, or just plain geeky. At home she poured herself into a hot bath, stopped thinking, stopped everything.

Monday was a madhouse, they knew it would be. The tent vendor reported a missing table, it was turned over to the insurance company. The ball caterer's bill was analyzed, Kelley found where it had been padded, let just a bit of it go, complained about the rest. Telephone calls poured in, compliments, complaints, some with no purpose whatsoever. Kelley and Sam knew, pretty well, that was the last of it, planning for the winter gala and next year's massive event would start next week.

On Tuesday afternoon, Kelley was cleaning her personal effects, found the slip of paper with Clark's number on it, forgotten in the maze of weekend details. She plugged the number into her phone, ignored it for the present.

She stopped by a restaurant on her way home, got them to make her take out while she sipped a glass of wine. Of course she was approached by a guy, a little sloppy in his dress, in his manner. "So, what's a girl like you doing in a place like this," he asked.

"I don't know. Just having a glass of wine."

"Can I buy you another?"

"No, thanks," Kelley refused, "Just one's enough for me." She let him make small talk, even practiced her flirting a bit. By his eyes she could see he was getting the idea he stood a chance, she actually put a hand on his arm when he told a bad joke, teased him along. But when the bartender delivered her Shrimp Mex Bowl, she left the dregs of her wine, said, "See you!"