Chapter 5

Allison was sittingin the library Tuesday night, working on her paper about The Monk. Not surprisingly, she was more and more entranced by the book, although at first, she'd thought it was boring. Once the gothic tale had begun to ensnare its characters into deeper and deeper sins, she'd was caught up in the action of the book, despite the sometimes stilted language. It was fascinating and depraved, and she found herself to be rather shocked it was considered a classic.

"My, my," a familiar voice said behind her.

A tremble went down her back, and she instinctively squeezed her legs together. Of course, she was wearing a skirt today. Since Friday, she'd worn nothing but skirts, knee-length or mid-thigh but always skirts. The weather had been beautiful, so it made sense. Of course, she hadn't been hoping Todd would somehow find her on campus.

"What are you working on there, Princess?"

Denying the hopeful feeling that rose in her chest, Allison made her expression blank and calm as she turned her head to look at Todd. The unruly hair that framed his face was right next to hers as he leaned down to see what she was working on. Before she could answer, he slid into the chair next to hers and moved it closed, putting on hand on her thigh where the hem of her skirt laid. Because he was facing her, no one would be able to see what his right hand was doing under the table. His left resting on the back of her chair, so she was halfway encircled by his arms.

She cleared her throat.

"It's an essay on Matthew Lewis' The Monk. I'm arguing that Ambrosio's lack of experience with actual moral issues and real-life situations is what causes his eventual descent into depravity. Because he has no firsthand experience to draw strength from, he makes the first step. His moral strength, which is so impressive to his congregation, is actually weak because he's never been tested."

Todd raised his eyebrows, one finger making a little circle on the bare skin of her thigh. Keeping her expression bland was becoming more and more difficult as the soft touch moved from the top to the center of her inner thigh.

"Interesting," he said, but the flavor of his voice told her he found her body much more interesting than what she was writing about. The touch on her thigh became firmer and slid upwards, under her skirt.

"What are you doing?" she asked, her voice dropping to a whisper.

"Testing your depravity," he whispered back. Allison bit her lip as he found her pussy lips, pushing the crotch of her panties to the side. Her legs spread, and she found herself sinking down in the chair, giving him more access. What was she doing? She almost sat back up, but then his finger penetrated her, sinking into her moist sheath, and his thumb rubbed over her clit. It was all she could do not to moan loudly enough to disturb the entire library.

Todd's gaze was steady on her face. She snuck little glances at him, cheeks flushed with heat, feeling much too embarrassed to look him in the eye. He was fingering her in the library… and she was letting him. A second finger pushed in beside the first, and a whimper escaped from her throat.

"How deeply do you want to descend into depravity?" Todd's voice held heat and seduction, the hot breath moving across the skin of her neck and her collarbone as he leaned in close to her ear. To a casual observer, it would look like he was murmuring sweet nothings to her or perhaps sharing a secret. Pressure grazed over her clit, and Allison quivered, her hands gripping the table to keep from moving too much.

"You told me one of your fantasies. You wanted to be free to do what you really want. I'm going to make that happen for you." His low, steady tone was almost hypnotic. Reality became fuzzy around the edges as he moved his fingers back and forth inside her, slowly increasing the friction against her clit. Allison's insides clenched around him, the fear of getting caught, increasing her arousal.

"Had you ever thought about anal sex before?" Allison shook her head, and he chuckled. "Well, you seemed to enjoy it."

She closed her eyes, not wanting to see the triumph on his face. Yes, she had enjoyed it, but that didn't make it okay. It was dirty and wrong. She squirmed as she felt a finger brush against her asshole. The two inside of her curved up into her body and pressed against her g-spot. The jerk of her body allowed Todd to get his arm around her waist and pull her closer to him, holding her in place as he finger fucked her.

"Spread your legs more for me, Princess."

Hearing him call her by the mocking nickname should have infuriated her, as it usually did, but it just turned her on more. Beneath her shirt, her hard nipples rubbed against the lacy material of her bra, aching for attention as she leaned back against his strong arm. The slow movements inside of her aroused the desires Todd had awakened.

"Have you thought about being with more than one man?"

Allison moaned again, unwilling to shake her head yes or no. What if the waiter on their first date had joined in instead of just looking at her bare breasts? Thinking about it made her pussy clench again as he circled her insides.

"Does the idea of getting caught get you off, Princess?" Her eyes popped open, and the shaking of her head had him catching her shoulder with his free hand, easing her back. "Too scared of Daddy. Relax, Princess, none of this is going to get back to him as long as you're a good girl and do as you're told."

She shivered as he added a third finger, his thumb rocking against her clit as her eyelids fluttered down again. The tone of his voice had sent her back into that almost dreamlike state, the pleasure building in her body, and she knew she was going to cum soon.

"How about being watched?"

Allison moaned, which had become her way of saying yes. She'd enjoyed having the waiter looking at her, she couldn't deny it. She'd always enjoyed the lust in men's eyes when they'd looked at what they couldn't have.

"What about being with a woman? Have you ever thought about that?"

Once or twice, when she was drunk, she and Chrissy had kissed and rubbed against each other, especially if there were guys around to watch. The idea Todd might push her farther than that… Her grip on the desk tightened, and she shuddered against the firm hold of his arm as she came, her mind flashing with images provoked by his questions, imagining herself engaging in the forbidden activities.

The sound of Todd's chuckling brought her back to earth. "Well, I guess we have the answer to that." Allison sighed as he pulled his fingers from her and put them in front of her lips. "Suck, sweetheart."

Obediently, she licked him clean of juices, squirming a little at her own brazenness. Her hands pushed at her skirt, settling it back into place over her lap. When he pulled his fingers from her, she made a face at him. Todd just smiled.

"I'll send you an email tomorrow. See you Friday."

Unsurprisingly, Allison couldn't concentrate at all after he left.

* * *

Hello Princess,

I've decided Friday night is our night together. For the next five Fridays, you're mine beautiful. Meet me at my work at 4. My office building is 555 Trump Street, Suite 380. I'll be the only one there. I'm in the back office on the right, and I'll be expecting you. Don't drive.

I think I'd like to see you in a sundress. Keep it low cut and short. No underwear. Put your hair in pigtails. I'll be waiting.

Your Knight in Shining Armor.

* * *

"So how are your classes, sweetheart?"Daddy asked over Thursday's dinner.

"Good," she said, smiling brightly. "I'm writing a paper for my junior English class right now and reading The Taming of the Shrew for my Shakespeare class." She hesitated. "Actually, there's a study group that's going to start meeting on Friday evenings to discuss Shakespeare's plays and language. If it's okay with you and Mom, I'll be joining them."

"Of course," her Dad said, smiling indulgently. Mom nodded her head, seconding his permission, not that she ever disagreed with him. "What time?"

"Oh, ah… usually a little before dinner time," she said, thinking quickly. "They order in food for dinner, and the study session run kind of late sometimes, I've been told. People get into the discussion, but it's supposed to be very helpful."

"That sounds wonderful," her mother said in a tone that sounded like she meant anything but. "I hope this won't interfere with your dating life, dear."

"Nonsense," Daddy said. "She'll still have her Saturday nights, and it's better not to be distracted during the school year, anyway. You're setting a good example, Allison. It's appalling how many young men and women spend their Friday nights partying, getting drunk, and indulging in all sorts of irresponsible and amoral behavior. We're so proud of you."

Allison smiled weakly.

* * *

As she walkedinto Todd's office building, her pigtails bobbed. The short pink sundress rode up her shapely legs, and she had to constantly pull the straps back onto her shoulders. She looked gorgeous, even if the pigtails did make her look five years younger. At twenty-one, that five-year reduction made quite a difference. Why did men have this obsession with wanting girls to look younger, anyway? Shave her pubic hair, wear pigtails—it shouldn't give her an illicit thrill.

Her pussy was already wet and leaking in anticipation, and she worried people would be able to smell it on her or someone she knew would see her. For the first time in her life, she'd taken public transpiration to get somewhere. Her large purse carried the light sweater and underwear she'd been wearing until five minutes ago when she'd snuck into the bushes next to his building to take it all off. Being without a bra in this dress was particularly perilous.

Todd smiled as she scurried into his office, clutching her purse in front of her and her slim legs flashing.

"You can put the purse there," he said, nodding to the chair next to his door. As soon as she put it down, he could see her nipples poking through the thin material of her sundress. Standing, he gestured to her. "Come here, I want to show you something."

Curiosity aroused, she walked around his desk. Putting an arm around her shoulder, he propelled her to the floor-to-ceiling window.

"See out there?" Her nod made her pigtails bob. "My friend works in that building. I told him he should look up here at about this time today. Don't worry, he won't recognize you."

Smiling at her, he watched the embarrassment slowly creep up her face as his full meaning sunk in. No wonder he'd wanted to know about her other fantasies. And just like the previous one, now that it was here, she wasn't sure what she'd gotten herself into.

"He won't tell anyone, and he knows better than to take pictures. This is just for our pleasure. His. Mine. Yours."

She felt grateful for the reassurance, but at the same time, she was nervous knowing that someone would be watching their interaction. Though her pussy was flooding, she still felt an impulse to show more reluctance, to put up a bit of a fight. Otherwise, what would their witness think of her?

Fighting wasn't going to do her any good. She needed the rest of the tapes, so there was no choice. The blackmail made everything easier, opening up entirely new possibilities she would have never considered under other circumstances. Now, she had no choice but to give in, and by doing so, she would experience everything she'd always wondered about.

Submissively, she lowered her head as he slipped the straps of her sundress off her shoulders. He turned her, so her front was facing the building across the way. Standing behind her, he cupped the undersides of her breasts, stroking her nipples. She sighed as the familiar pleasure rose.

Opening her eyes, she looked across the way and saw a guy standing at the window Todd had pointed out. His face was too far away and obscured by binoculars for her to make out features, but she could see he was stroking his dick as he watched the show. Allison tensed, but there was nothing she could do, and slowly her body relaxed.

Todd handled her breasts more roughly, pinching and squeezing, pulling her nipples as far as they would go before releasing them. The top of her dress was bunched around her waist, the skirt gently swaying as she moved her hips back and forth, grinding her ass onto his hard dick—although he was fairly sure she wasn't aware of the fact. One of the great things about playing with her breasts first was she tended to lose control of her body if he did things correctly. Slowly, he used one hand to lift the skirt of the dress above her hips, exposing her bare pussy to his friend.

Allison ignored the distant watcher as Todd's fingers slipped through her wetness, enticing more heat between her thighs, spreading her legs to allow him better access. She wondered at her wantonness—the exhibitionist streak she had in her which had never been allowed out to play. The slickness of her pussy stated her definite arousal. Todd turned them both, so they were sideways to the big window as he lowered his head to her nipples, sucking them in his mouth and teasing them with his tongue. He noticed the pale skin of her breasts still held the faint traces of the hickeys he'd given her last Friday. He added only one to each breast on the inner curves of her cleavage.

Lowering himself to his knees, he pushed his face between her thighs, his mouth aimed for her wet silkiness. Allison moaned as she tried to keep herself upright, spreading her legs a little more to allow Todd more access and give herself better balance. Clutching at his head with her hands, she let her own head fall back as she whimpered. He gave her pussy a tongue-lashing, using his hands on her ass to push her into his mouth. Once Allison was balanced, she let one hand drift up to her own nipples, pinching and twisting them… until she remembered their watcher and quickly pulled her hand away as if her fingers had been burned. That was too embarrassing.

Panting, she tried to keep control as Todd pushed his tongue into her hole and wiggled it. She had to bite her lip to keep from screaming with pleasure when he sucked her clit into his mouth, rolling the little bud with his tongue. When he bit down gently as he sucked, she came, moaning and shaking. Her pussy juices slicked her upper thighs, and the smell of her cream filled the room. Her boobs jiggled as she came, bouncing while she struggled to stay standing. It wasn't until her grip on his hair loosened, Todd finally released her clit.

Legs shaking, Allison allowed him to bend her over his desk with her ass facing the window. Her inner thighs were glistening with her juices. Todd ran his finger up her thigh, then stuck it in his mouth, sucking it clean. He waved to his friend across the way, then used his fingers to spread her pussy lips, displaying their deep pink and engorged state. Carefully inserting one finger into her hole, he swirled it around. She moaned and moved her hips slightly. Pulling the finger out, he positioned it at her asshole, pressing lightly on the little hole. Shocked, Allison stood, her hands coming around to cover her bottom.

"Don't do that!"

"You liked it well enough when I stuck my dick up there."

"It's dirty." Her voice shook as she tried to forget the pleasure of when she came while he was in her ass. "It's dirty, and it's wrong. Things aren't supposed to go in there."

Todd didn't say anything, just used his hands to spin her around and push her down onto the desk, one hand splayed heavily across her lower back.

SLAP!

Allison squealed as his hand smacked her ass, leaving a bright pink handprint on her creamy cheek. SLAP! SLAP! SLAP! Crying out and squirming, her ass cheeks jiggled as his hand impacted them, and her body bounced, trying to escape the punishment.

"Stop! Stop it hurts!"

SMACK! CRACK! SLAP!

It hurt, but worse, it made her pussy weep again. The fire in her buttocks from the sharp pain was somehow transforming into something that made her want to be fucked and fucked hard. Todd was rather surprised, he had only meant to give her a couple, but there was a sensual plea in her voice as she begged him to stop. She was obviously enjoying her spanking, her bottom pushing up to meet his hand despite her pleas. In fact, the moment he stopped, her butt went back up again as if begging for more. Well, if a little punishment and force were what she wanted, he could certainly give her that.

"You are mine to do with as I please on these dates." His stern voice brooked no argument. "If I want to put something in your tight little asshole, you will spread your cheeks and let me. As far as I'm concerned, I'd be happy to see plenty of things filling that tight little hole."

Allison nodded. She didn't trust her voice. It would surely give away how much he'd turned her on, then she'd lose even more control. It never occurred to her he'd already realized how much she'd liked it.

He pushed two fingers roughly into her pussy, making her wiggle and moan, and without ceremony, forced the soaking digits into her ass. Allison yelped as her sphincter was stretched open, a slight burning from the sensation as his fingers dug deep. He began moving them in and out of her body, making her even more uncomfortable and horny. The deliciously full feeling was back, just as forbiddingly pleasurable as before.

There seemed to be no lower debasement with her ass impaled on his fingers while she was bent over his desk, and his friend watched through binoculars across the street. Incongruently, she wondered what it looked like to see his fingers fucking her hole, then wanted to slap herself for thinking something so disgusting. She gasped and moaned as the sensations changed. He was twisting his fingers right, then left inside of her, trying to spread them apart in her tight channel.

Finally, he pulled his fingers out, and her entire body relaxed in relief. Pulling her off the desk, he pushed her face-first against the glass. Nipples hardened at the cold encounter, her boobs smashed flat against the window. When she tried to move back, she encountered his unyielding body. The sound of a zipper, a few adjustments, and he was pushing his dick into her pussy from behind. He held her arms at her wrists, pressed high above her head against the window. One cheek and her breasts were flattened against the cold glass as he began to thrust in and out of her quickly, her reactions quite visible to their audience.

Just as she felt her own orgasm start to build again, Todd moaned and thrust hard into her, sending spurt after spurt of cum into her unfulfilled pussy. He pulled out quickly, leaving her gasping and wanting, braced against the glass. She straightened and pulled her dress down and the straps back over her shoulders, covering herself. Glancing out the window, it was obvious their audience had shot his own load all over his window and was now cleaning up the residue.

Todd didn't give her a chance to grab a tissue to clean up. Taking her hand, he pulled her out the door with him as she felt his cum beginning to drip down her thigh. Well, hopefully, they'd be able to get to his car without seeing anyone.

"Quick stop," he said, grinning at her, before coming to a halt in front of a door just next to the main entrance. He knocked on it. Allison grimaced and squeezed her legs together, trying to halt the flow of his cum down her leg. The door opened, and Todd leaned in.

"Hey guys," he said as he pulled her up next to him. "This is Allison. Allison, these are our security guards."

Allison's eyes flickered quickly over to the monitors in front of the man and woman sitting there and realized, to her horror, one screen showed the office she and Todd had just vacated.

"Great show," said the man, grinning at her. He was a good-looking black man, maybe an inch taller than her with an average but muscular build. The woman sitting next to him was a stunning blonde, and her chest nicely filling out her uniform. She was also grinning at the couple in the doorway.

"Don't worry, Princess, they aren't going to tell anyone. They've even agreed to delete that part of the tape as long as you make sure it's worth their while."

"That's right," said the man; apparently, he was the talkative one. "You've got my girl, Laney here, all riled up."

"Mmmm, it's a good thing you've got a fantasy about being with another woman," Todd whispered in her ear before pushing her forward. Allison opened her mouth to protest, but when Todd pushed her, she'd stumbled, and Laney stood and caught her. Before Allison could do more than stutter, the woman kissed her full on the mouth. Allison parted her lips, and a soft probing tongue slipped into her mouth. It was like kissing Chrissy as Laney's huge breasts pressed into her own. Then she pulled Allison over to the chair she had been sitting in and pushed the frozen brunette into it.

Allison slumped in the chair, unresisting and unbelieving as the blonde's strong hands pulled her hips to the edge of the seat and lifted the hem of her dress.

"Oh, my." The blonde turned back to look at Todd. "Looks like someone left me a treat."

Todd grinned at her as she turned back to Allison and began licking her open thighs. The blonde head worked her way farther and farther up Allison's smooth thighs, cleaning Allison's juices and Todd's cum from her legs. Her touch was much softer, gentler than any man's Allison had ever experienced. Big hazel eyes watched the process in complete shock. Could this really be happening?

When Laney reached her pussy, Allison gasped, and her head flew up. The men were staring at the lesbian show. Her face turned bright red with humiliation, even as she whimpered with need. Todd's stern eyes caught hers, and she stared straight at him as the blonde made sighing noises into her sloppy pussy. Moving her hips in time to Laney's expert licking, Allison couldn't tear her gaze from Todd's, even though she could see the black security guard stroking his dick out of the corner of her eye.

It was the best and worst kind of exhibitionism as the men watched her breasts heave and her face contort with passion while another woman feasted on her pussy. All of it just turned her on more and more. She'd never realized she had such an exhibitionist streak in her, but something about being watched flat out did it for her. Seeing the men's facial expression as they watched her moan and hump the blonde's face, witnessing their obvious desire, turned her on more and more turned.

The blonde head moved lower, and she began licking around Allison's crinkled asshole, sucking on it, and pushing her tongue against the sensitive entrance. Allison almost screeched and jumped up, but there was an obvious warning in Todd's gaze, so she slowly forced herself to relax. The anal rimming felt amazing, little nerve endings humming with pleasure as the blonde's soft tongue teased her asshole. Biting her lip to keep from moaning with pleasure, Allison's body jerked as the blonde managed to force just the tip of her tongue into Allison's ass. It felt incredible, but so wrong and dirty—compounded by the men watching.

Laney unexpectedly pinched Allison's clit, and she came, the shame and humiliation buoying her up on a wave of ecstasy as her tender nub was twisted and pinched. The tongue in her ass wriggled, heightening Allison's passionate cries along with her humiliation. Finally, red with embarrassment, Allison slowly relaxed. Laney pulled her tongue from Allison's asshole and began licking the juices that had flowed from her pussy.

Was she going to be expected to return the favor? Allison wasn't sure she could handle that today. There had been so much already. How many boundaries could someone push in one night?

Fortunately, when Laney pulled away, she just winked at Todd, not seeming interested in receiving a similar favor.

"You kids, get on out of here and have a good night. It looks like me and Carl have some business to take care of."

Big boobs bouncing, the blonde got to her feet as Carl moved toward her. Todd said goodbye and pulled Allison out the door as the two in the room began to kiss passionately. It occurred to Allison, Carl would know what her pussy tasted like.

It was a little overwhelming.

Thankfully, Todd didn't want to do anything more but run by a Checkers and eat. On the way home, she gave road head for the first time, which did double duty of keeping anyone from seeing her in his car and pleasuring him. His dick was still faintly flavored from their sex. Around the corner and two blocks away from her parents' house, Todd pulled over and turned off the lights, so she could finish his blowjob while he played with her nipples, pinching, and tugging on the sensitive buds.

She was becoming quite adept at swallowing his cum, sucking the warm froth down and not losing a single drop. Afterward, he let her break the DVD and promised to throw away the pieces when he got home. Even broken, she didn't want it anywhere near her parents.

Allison got out of the car incredibly worked up, her nipples sore and her pussy unfulfilled. Todd drove away with a cheerful wave.

Fortunately, her parents were out. As was becoming a habit, as soon as Allison got inside and was in the privacy of her own room, she masturbated. Closing her eyes, she could see the two men watching her as the blonde licked her pussy, remembering the guy who watched as Todd fucked her up against the window. Picturing their faces, she came hard on her fingers, one of which had somehow slipped in her asshole, making her feel even fuller as her holes clenched and shuddered.

She laid there, completely exhausted, and pulled her fingers free. Only three more dates. Could she last three more dates without becoming completely sexually depraved? And what would she do when they were over?