Teaching Nancy

Teaching Nancy by missadele

Nancy sighed as she closed the car door behind her. She had been delivering dry cleaning for nearly four months now, a fairly easy job, but still dreaded her last delivery. Most of her customers were fairly wealthy, snobbish, and made a point of being quick and polite with her, if not a little brash. No customer had ever really made her feel uncomfortable; not like Gregory Burgess.

Nancy tucked her dark hair behind her ear before starting the car and glancing in the rear-view mirror. She didn’t exactly try to make herself look ugly when she made the delivery to Mr. Burgess, but she avoided makeup. It wouldn’t have really been possible anyway. She had never really felt like she was beautiful, but she knew she wasn’t ugly. Her dark hair had a hint of red in it, and came down to the small of her back. It swept decidedly across her forehead and curved around her ears. Her eyes were a startling green, surrounded by thick eyelashes that batted in a careless, bored sort of way. Away from Mr. Burgess, she tended to be a very relaxed, mellow young girl; her eyes and body language showed it. However, as soon as she pulled up in front of his expensive complex, her narrow shoulders tensed, her collarbones protruded and her throat contracted as she swallowed. She wrung her hands and looked down at her bare legs. She didn’t have to wear shorts, but it was dead in the middle of August; the hottest month of the year. She rubbed her hands over her thighs, and bit her lip. She glanced one more time in the mirror, letting go of her thick bottom lip before stepping reluctantly out of the car. She felt exposed before she had even reached his door, noticing for the first time that day the way her shorts rubbed against the soft flesh of her inner thighs and inched up with each step.

Mr. Burgess had never actually harassed her, exactly. If he had, she certainly would have reported him. The last thing Nancy was capable of was letting someone walk on her. She felt a little shallow for a moment when she wondered if she would feel different were he attractive. Mr. Burgess was an older man; she guess him to be in his late forties. He wasn’t obese, but had a big gut that hung over his trousers, and stretched out the buttons of his shirts. He had large hands and forearms, covered in dark hair. She shuddered slightly at the thought of him, as she stepped up to his door. She rearranged the dry cleaning in her arm, to knock on the door. She stood quietly for a few moments, and used her free arm to wipe the small amount of sweat collecting above her lip. She had begun to notice something that was beginning to disturb her the most about the whole situation. Although her instinct was to run away at that moment, despite her being generally repulsed by Mr. Burgess, something began to happen as it had the past few weeks standing there waiting for him to open the door. She began to feel aroused, and could feel her pussy dampening at the thought of him. Her heart leaped when his door swung open then, and he smiled at her.
“Come inside, dear. It’s hot out.” He turned and walked away, leaving the front door open.

“Well…I can’t stay. I’ll just drop these off somewhere and be on my way.”

“Isn’t this usually your last stop for the day?” Mr. Burgess called out from the kitchen, where a cabinet door was open and then shut.

“It is, but…where should I put these?”

“Oh, just a moment and I’ll take them. “ She stood nervously, and shifted the weight of the dry cleaning in her arms, before Mr. Burgess came out from behind the kitchen. He held a glass of ice water.

“Here. One for the road,” he said, handing her the glass and extending another to take the dry cleaning.

“Oh,” she said, awkwardly handing the bundle to him, and taking the glass of water. Normally, she would not have taken any beverage from a strange man, least of all Mr. Burgess. But just as the thought of him had begun to arouse her, other strange things had been happening. As the months had gone by, each time she visited him she felt more and more compliant with his offers of inviting her in, chatting, taking glasses of water and walking her out to the car. She had declined nearly all advances at first, but she found herself agreeing, nodding and passively complying with most things he suggested.

“Take a seat,” he said, at that moment before sitting down in a chair himself. Well, maybe that’s a good sign. At least he’s not asking me to sit next to him. She turned and shut the front door, before crossing the room to sit on the couch opposite him. She crossed her legs, and her foot began pedaling nervously, bobbing up and down.
“Stop that,” he said casually, giving her a smile and glancing at her foot.
“Oh. Yes, sorry. Nervous habit.”
“Of course, dear. So how was your day?”

“It was fine. And yours?” She responded before taking a sip of the ice water. It felt wonderful sliding down her throat. It really was too hot. His apartment was cool, and she felt her nipples stiffen and the flesh of her thighs rose into goose bumps.
“It was great.” He ran his eyes from her lips down to her breasts, pausing there for a moment, before continuing down her legs. She felt a moment of clarity at that moment, and she looked about her nervously, and then stood.

‘I really need to be going. This is my last stop, but I am awfully worn out. I’m ready to get home.”

“Oh, I insist you stay for just a little while longer. Just finish the water, cool off for a few minutes, and then I’ll send you on your way.”

“Oh, I don’t mind. I’d like to actually get home and take a shower, I feel sticky from walking around outside all day,” she responded with a smile and began walking toward the door. He continued behind her all the way out to the car, politely arguing. She shook her head and smiled as she came to stand in front of the car. As she fumbled with her keys, still arguing, she accidentally dropped them. She quickly bent to pick them up, and as she did, Mr. Burgess leaned down to the momentarily exposed flesh that formed her soft cleavage, and ran his tongue from the bottom of the crevice to the top. She flinched and yelped slightly, bolting upward. She was shocked at the touch, at his audacity. She stood unmoving before the large, older man, who stood calmly and smiled at her.

“Relax,” Mr. Burgess said, and Nancy felt a wave of endorphins run through her body, and her shoulders visibly dropped down.

“Give me your keys,” he said, extending his hand. She gave them to him, knowing that it was not what she wanted, but did it anyways.

“Now,” he said, stepping closer, and putting his large hands on her warm shoulders.
“There’s no need to be afraid. Just relax,” he said again, and she felt another wave of serenity run up and down her spine. He dropped his eyes to her breasts, and his hands fell to caress her throat, and then his fingers began playing with the top button of her blouse. She stiffened a bit when he did this.

“Ssh,” he said, and gave her a reassuring look.

What the hell is this? Why am I doing this? Why am I letting him do this? Oh, my God. Although the complex was quiet, and neither of them made a sound except for their breathing, Nancy’s head was racing. She was still, as he began unbuttoning her blouse- out in broad daylight where anyone could come out and witness it. The part of her that screamed at her to push his hands away, get in the car, drive straight to the office and report this bastard was numb, and she stood passively, as his fingers reached the middle of her blouse. He stopped there, and ran his hands up the part of her chest that was exposed.

“Bra,” he mumbled, clearly displeased.

‘We’re going to have to address that eventually.” He ran his hands back down and she shivered at the soft touch. He continued unbuttoning Nancy’s shirt until he reached bottom, and then he walked to stand behind her. He breathed in her neck as he put his hands on her shoulders.

“Relax,” he said once more, and then he put his fingers on the edges of her blouse and pulled it away from her, and then slid it down her shoulders and let it drape over one hairy forearm. He ran his hand over the back of her bra, seeing that the clasp was in the front. He replaced his hands around her chest, and stood closer to her, pressing his gut and the erection that was now poking through his trousers against her backside. He carefully unclasped her bra, and she stiffened only slightly this time, as he pulled the cups off of her, and letting the straps fall down her arms that dangled motionless at her sides, exposing her breasts to anyone who may pull up in the parking lot or come out of their apartment. He draped the bra over the blouse that lay over his arm, before lightly putting his hands on her arms.

“You’re going to come back inside now, and be polite. Understood?”

‘Yes. Yes, of course,” she said, and began following him back to the apartment. Once back inside the cool apartment, her nipples stiffened again. This time though, they were fully exposed, and Mr. Burgess came to stand in front of her after closing and locking the front door. Her tits bounced gently as her arms came up to cover her breasts, but she stopped when she made eye contact with Mr. Burgess. He shook his head.
‘No, dear. Arms over your head.” She reluctantly put her arms behind her head, pushing out her chest, and making her nipples stand as though unashamed of the attention they were now getting. He came to stand in front of her and began cupping and caressing her breasts.

“I have been wanting to play with these for a while. It’s taken quite a bit of patience. I knew you had a fantastic rack. I think you have the perkiest tits I’ve ever seen,” he said, smiling, as he casually began tweaking her nipples. She held her breath, and a hot wave of pleasure shot straight down to her pussy, that she realized was now drenched.

This is not happening, this is not happening, this is not happening.

These thoughts dominated her mind, but she only stood there and let the repulsive man play with her breasts to his heart’s content. He stopped after several minutes, and she sighed in relief and also regret.

“You know, you have been very rude to me on several occasions. It’s taken a lot of restraint to not put you in your place right off the bat. But I think today is that day,” he said, almost seeming to be talking to himself more than directly to her. He turned and motioned for her to follow. He walked over to the dining room table, and motioned her to stand in front of it. She did as she was told, and was still for a moment waiting for the next command.
“Well? Bend over it.” Her eyes widened with horror, and she turned to look at him. He sternly pointed to the table, and she slowly faced straight ahead again, and slowly bent over the table, her ass slightly higher than her back.

She felt him move behind her, and then put his hands in front of her waist and begin to unbutton her shorts. He slid them over her ass and down her legs and left them there crumpled at her ankles. He slid his thumbs under the waist band of her panties before sliding them off, exposing her tight, muscular ass. He only pulled them just below her upper thighs, before standing back to take in the view. She breathed quickly in anticipation. He removed his belt and then placed his hand on her warm bottom, caressing her. Her ass clenched for a moment, and he slapped one cheek, and she whimpered.

“No clenching, no moving, no screaming. Got it?“ She nodded, but he slapped her again and watched in pleasure as the globe of her bottom wiggled in discomfort, making her whimper again as the skin of her ass began to glow red.

“No, what?”

She swallowed in confusion, but then understood. Oh, God this is so demeaning.

“No, sir.” He patted her bottom, then.

“Good girl.”

He held the belt in his hand, wound up, and sent it cracking down on her helpless ass. She whimpered more loudly this time.

“I will let that one go, but just this once. I don’t want to hear it again. Next time you protest in any way, the spanking doesn’t count and I’ll start over. Got it?”
‘Yes, sir,” she said, holding back tears. He sent his belt down again over her bare ass, and she fought desperately to not move or whimper. He paused to see if she would, and when she did not, he sent the belt down six more times without pause. Afterward, they both were breathing heavily, both in arousal, but Nancy panted in paint as well.

He bent down and removed the shorts that had laid crumpled at her feet, and then straightened up for a moment to pull her panties the rest of the way down, and then off. He left her bent over the table for a moment, her stinging red cheeks waiting in anticipation. He had put her clothes away, she realized when he came back without them. She was completely naked now, and she didn’t even know where her clothes were.
He then used his foot to push at the insides of her feet.

“Open up, dear.” She opened her feet shoulder width apart, but he tisked her.
“Wider, dear.” Once her thighs were wide open, he wrapped the belt around his hand again, and cracked down, sending a jolt of pain over Nancy’s inner thighs. It was even more painful, and she held her breath, and waited for the next one. Five more followed, cracking down over each ass cheek, inside her now exposed asshole and inner thighs. The last one even caught her pussy, making her eyes water and simultaneously sending yet another hot jolt into her groin. Her ass and thighs were bright red when he was done, and then he left her standing there for a moment and came back with some sort of oil. He put a small amount into his hand, and then began gently rubbing it over her hot ass and thighs.

“This will prevent bruising, sweetheart. Just be still.” There was something undeniably soothing about his voice and touch, and she relaxed again, and her breathing had returned to normal by the time he was through. His hands withdrew, and she began to sit up on her elbows.

“Have I told you to stand?” She bent back down in fear he would take out the belt again.

“No, sir. I’m sorry.” Her voice cracked when she said it, and he placed a hand on her back, and began rubbing it.

‘It’s alright sweetheart. Don’t be so jumpy. I don’t expect you to understand my rules already. Once I’ve taught you my rules, I expect you to obey them. If you don’t, there will be consequences. But right now, we’re going to take things slow. Just relax,” he said, still rubbing her back.

That word again, made her feel a wave of calm. She began to wonder if he had somehow hypnotized her. There was clearly something amiss here. He had done something to her, somehow, over the months. He had been planning this. He withdrew his hand after awhile, and then poured another small amount of oil in his hand, and then placed two fingers on the entrance of her asshole. Her thighs clenched at this new touch.
Oh, please no, she thought. She had never even let her boyfriends touch her asshole. It was off-limits territory and always had been. Of all people to be touching me like this for the first time! He just rubbed in soft circles, though; occasionally pressing a little at the entrance.

“This calms you. This makes you feel comfortable and safe. The feeling of my fingers near, on or inside your ass makes you feel happy, relaxed and submissive.” He is hypnotizing me somehow! she thought, and wondered for the first time what Mr. Burgess did for a living.

“Okay, let’s get you in a more comfortable position,” he said after a few minutes of rubbing her asshole. He put his hands underneath her stomach and guided her to a standing position. He turned her around and gave her a smile, before taking her hand and guiding her to the couch. He sat down and motioned for her to lay across his lap. She slowly climbed onto the couch, feeling more naked than ever, and laid down, her naked pussy pressing against the erection just beneath his pants. Her ass rose straight below him now, as she bent her elbows and rested her hands by her head.
‘Good, girl. Now, just relax,” he said yet again, as he began pushing at her asshole again with two fingers.

“Now, take a deep breath,” he said pausing, as he continued making small circles over her anus. She did so, and when it peaked, he continued.

“And let it out slowly.” When she did he slowly pushed one thick finger into her asshole. He began pumping it in and out slowly, and continued telling her that it made her feel happy, submissive and relaxed. And somehow, it began to. She began to enjoy the feeling, even when a second large finger joined, stretching her ass slightly. He continued pumping two finger in and out of her ass, and her breathing became more slow, and she realized she didn’t want him to stop. However, he did after several minutes. Then he slid his fingers down her bare slit, and traced his fingers around her wet pussy.

“Oh, that’s better than I expected. You’re extremely turned on,” he said, and began using the wetness from her pussy to stroke up and down her clitoris. It felt so good, her ass began to rise and fall with his rhythm, and she continued to when he didn’t stop her.

“Good girl. You’re doing great,” he said, continued to finger fuck her until she felt as though she could no longer stand the pleasure. As he continued, fucking her pussy more and more intensely, he began to speak to her.

“When you try to touch yourself, it will feel wrong. It will make you feel dirty, and you will long for my touch. The thought of anyone, including yourself, touching you this way makes you feel unsafe and turned off. If you try to touch yourself, you will be unable to achieve an orgasm.“ He continued saying things like this, and all the while Nancy did not really notice. She had become so lost in the pleasure of his touch, she could barely hear his words. He was pumping two fingers in and out of her pussy when he pulled his fingers away, and she moaned quietly in complaint.

“It’s time to calm down, sweetheart. You can have an orgasm when you’re ready for my cock. Okay?” She breathed out in frustration.

‘Yes, sir,” she said meekly.

He picked her up, turned her over in his lap, and then held her up before putting his fingers to her mouth.

“Suck them clean, now.” She took his fingers in her mouth, and tasted the juice from her pussy for the first time. Ordinarily, the idea would have disgusted her, but now, it aroused her even more. She sucked on his fingers until he was satisfied, and then he slid them out from between her soft lips.

“Stand up.” She did so without hesitation, the inner voice that had been telling her how much she did not want this becoming more and more distant. He unzipped his pants and let the huge erection spring out. He pointed to the ground, and Nancy fell to her knees, obediently.

“Suck.” Nancy tucked her hair behind her ears and bent forward, getting an eyeful of the enormous cock in front of her. She took it in her mouth, the head alone stretching her full lips. She began sucks gently, and pumping up and down. He held her head and began guiding it up and down more vigorously.

“Good baby, keep sucking.” Nancy looked up at Mr. Burgess, the man who was now beginning to possess her body and mind, and continued sucking. After several minutes, he pulled her back, and pushed her hair away from her face.

“Now suck my balls.” He held them in one hand, and guided her head down to them with the other. She took them into her mouth and began sucking them carefully, running her tongue around them over and over. He moaned in pleasure, letting his head fall back. She let go of them after a moment and began sucking up and down on his long shaft. Nancy’s inner voice was almost completely gone now, the longer she mouth fucked Mr. Burgess. His hands closed around her head, pumping her mouth harder and harder against his cock. He held a handful of her hair as he began tensing up.
“Good girl, almost there. “ Nancy was lost in the moment entirely, as Mr. Burgess moaned and let out a hot stream of cum into Nancy’s mouth. She choked slightly, but swallowed his entire load. Nancy finally let his cock fall from her mouth, and she put her hand to her mouth to wipe off the residue of cum on her chin.
“No, Nancy. Clean yourself off with your tongue, and then clean my cock.” She used her fingers to wipe the cum from her lips and chin and put them in her mouth and sucked. She then bent down and ran her tongue along his cock and sucked the rest of his cum into her mouth.

“That’s it. I want it completely clean. That’s good.” He finally pulled her head away from his cock, and lifted her chin with his hand.
“You did good, Nancy.” Nancy nodded, and leaned back on her heels. Mr. Burgess patted his knees, and Nancy stood and sat down in his lap.

“You did well today, considering it was our first day. But we have a long way to go.” Nancy looked down after he said it, feeling a slight pang of trepidation at the thought. He lifted her chin, though.

“Look at me, Nancy. Now the first thing I want you to do is promise me that you will not pleasure yourself. Not unless I give you permission. Not tonight when you get home, and not all day tomorrow or the next day. You will wait for instructions until the next time you make a delivery to my home. Do you understand?” Nancy nodded.

“And Nancy…from now on, you will not wear a bra when you come here. If I discover you are wearing one, and I will check before you even enter my home, there will be consequences. Unless you want me to bend you over the table again, you will no longer come here wearing a bra. Understood?” Nancy nodded.

“Yes, sir.”

“Good.” Mr. Burgess smiled at her, but the smile was more from the thoughts of the lessons soon to come for Nancy.