Friday lunchtime had come and gone, and Chloe was getting worried. She was already getting 15 lashes this evening, and she had completely failed to get Tim to take another look and watch her masturbate. God knows how many I will get for that, she thought. He had sat in the same desk Thursday and today but hadn't looked, which she found strange, as he had never sat there until Monday. He must want to look.
Worst of all, was that at about 12:30 he had disappeared for a quick beer with some mates from the 12th floor, and he was not back. Nobody was supposed to take a 3-hour lunch break, and he had to come back; his keys and jacket were still on the desk. And now she would be leaving in 35 minutes. She had had her phone set up to record him since first thing yesterday, and it was going to be for nothing. She started to compose a text to Andy. 'Master, I have not been able to get Tim to watch. It has not been through lack of trying. Please show mercy.' Her finger hovered over send, and was moving toward the screen when she heard Tim's voice. She looked around and he was heading back to his desk, looking more than slightly drunk.
She watched as he slumped in his chair and spun around, then stopped himself and looked at his screen. It took all of three attempts for him to get his password right, but he appeared to be doing nothing once he did, just staring at the screen.
With her heart pounding in her chest, and her teeth trying to chatter, she coughed loudly. Her legs were wide open, her skirt was as far up as she could pull it, and his view would be as good as if she was naked, but he did not react. Chloe thought her heart would burst out of her chest, with how nervous she felt as she sucked in the breath to cough again. But as she was about to cough, he turned, slowly. She watched as he turned until he was facing her, and she hit record on her phone. As he leaned forward, almost falling from his chair, Chloe looked around the office. Nobody else seemed to have noticed, and there were no eyes facing this way. His gaze moved from her face, down to under her desk, and he stared for a good few moments. She was in the process of moving her hand, heart still pounding, when he looked back to her face. He seemed to take a moment to focus; he was clearly drunker than she thought. And then he said, "You are teasing me?" She was not sure if it was a statement or a question, but she replied as if it was a question. "No, I am giving you a little show is all," she said, her voice close to shaking.
There was a pause, his brain clearly needing the time to process. Then he asked, "Why?"
Chloe was starting to feel more confident. He was in a state, and he probably would not recall this clearly in the morning. If he shouted or made a scene, nobody would believe a word he said in this condition. So, she said, "Because I have been instructed to. I believe it is to build my confidence in my body, and make me more open to being seen."
That clearly was too much for his brain to process, he looked confused, before he said, "Why would you need to get more confident about your body? You are seriously hot; I have thought about you since the day we were introduced. You intim..." He cleared his throat, and tried again, "...intim...dite," he paused.
"Intimidate," Chloe put in.
"Yes, that's it. You in...what you said...men. Girls like you don't give guys like me the time of day." His voice gained slightly more composure towards the end of the sentence.
Chloe had never felt intimidating in her life. She was lost with how to respond to that, so she tried to pull this to a close. "You might feel like that, but I am terrified of my body being looked at, especially by strangers. So, you want to watch or not?" Her voice had more force than she felt.
"Yes," he said, and his eyes moved very visibly to under her desk. She moved her hand down, it was going to take a bit of work, as she had lost any arousal that she had. She watched his face as her fingers brushed against her exposed pussy lips. They were very soft and flat as she did, but she knew they would engorge and pop out soon. She was obviously a little colder than she thought, as she felt goose bumps when she slipped two fingers down, tracing her lips all the way to the bottom, parting them slightly there, pulling her lips apart just enough to show the wet hole inside. She knew when she had opened them just enough, because of the look of excitement that appeared on Tim's face.
She watched as his expression turned eager, while her fingers moved back up across her milky white lips--which she was sure were getting a pink flush now--to her clit. She circled it, pushing gently down, copying how Andy aroused her, waiting for the now-familiar feeling of her clit popping up through her lips, and exposing itself. She had a quick look around to ensure nobody was watching before she started to tease her clit, brushing across it, pushing around it to make it move and dance for Tim's eyes; they were wide open, and his jaw was slowly falling open too. From Chloe's point of view, Tim was making this all too obvious. She was considering stopping, when he dropped to his knees and disappeared from view. Chloe again scanned the office for anybody noticing, but nothing. She carried on for a moment then realised Tim had crawled under her desk. His head was between her legs, not touching anything, just...there. She could feel his hot drunk breath on her legs, his head no more than 6 inches from her pussy.
Chloe was not sure at all about this now; he was way too close, and as he rocked in his drunken state he was getting close enough to her pussy that his breathing could be felt against her lips. She continued, more nervous now. With her spare hand reaching for the phone and bringing it down to film under the desk, she now rubbed her clit, her hand in a better position to defend against Tim getting any ideas. Chloe did feel aroused--she had become very skilled at playing with herself to a point and stopping--but she didn't think she could cum even if she wanted to. There was something very erotic about Tim being that close that his breath was on her, knowing she would never allow him to touch her, but a climax was a whole different thing.
She moved her hand, slowly running it down her lips to the wet hole at the bottom, pulling the lips apart again, showing Tim, in close up, her inner lips and her inviting wet hole. She plunged her middle finger into it, forcing it up as far as it would go, enjoying her own wet pussy for a moment. For almost 5 minutes, she rubbed her clit and pushed her fingers into her pussy, feeling Tim's excited breath on her legs, and in moments that he really seemed to get into it, on her pussy. But as she was getting very little out of it, with no chance of bringing herself even slightly close to orgasm, she stopped, got up, and started to walk to the toilet. It took Tim almost 30 seconds to climb out from under her desk, and he looked totally lost.
Chloe walked back to be close enough to not draw any attention and said, "Go back to your desk and sleep it off. You are getting nothing else from me today."
Tim looked crestfallen, but seemed to want to comply, even in his drunken state. He turned, walked to his desk, and sat down. Chloe was surprised that did not take more effort. She turned again and headed to the toilet. Once there she washed her hands and straightened herself up; it was only 10 minutes until she left for the day, and she was off to see Andy, which made her smile. She had a quick look at the video: it wasn't great, but you could see his stupid drunk face, inches from her pussy. That was good enough, she hoped. Chloe put the video in a WhatsApp message and sent it to Andy. When she got back to her desk and started tidying to go home, Tim was actually asleep in his chair. She walked over, took his keys and left a note that said, "Your car key is at reception. You can collect it when you are sober."
She then picked up her stuff, and walked out to her car, stopping at reception to hand in the key and explain. The security manager took the key and assured her Tim would only get it back when he was fit to drive. As she drove home, she could feel the excitement build; she had no idea what to expect tonight, except at least 15 spanks, but she didn't care. She knew she would love every minutes of it.
Chloe pulled into Andy's drive, her normal parking spot, and hurried to the door. The delay with the key had meant she'd caught more traffic than normal and she was now 10 minutes late. She knocked and waited, listening for the footsteps of Andy coming to open the door, and felt her heart leap when she heard them.
Andy opened the door and swung it open to let her in. She stepped through, but before she could walk down the hallway, he said, "Stop!" Chloe stopped dead, and felt the door close, missing her by millimetres, heard the solid clunk as it closed.
"Remove all your clothes, and join me in the living room, please," Andy said, as he walked off past her, and turned into the living room.
Chloe started to remove her blouse and then bra. His voice seemed a little cross, but not excessively so. She placed her top and bra on her bag on the floor, and removed her shoes and socks. She smiled to herself, now standing in Andy's hallway, in just her skirt. If you had told her even two weeks ago that she would do this without hesitation or concern she never would have believed you. As she fumbled with buttons on her skirt she thought to herself that she had never been happier, and also how much she wanted Andy to fuck her. Her skirt dropped to the floor, and she was completely naked. She almost skipped to the living room.
When she got there, Andy was sitting on the sofa. As she entered, he said, "Come over here, and bend over."
Chloe complied, bending at the waist, and supporting her weight with her hands on her knees, her big pert breasts hanging down. Andy moved his hand and took hold of the breast nearest to him, stroking it, and gently caressing it, fingers subtly grazing across the nipple that was growing to a bullet quickly. She leant into the caress, enjoying his warm hand on her skin.
"You are due 15 from last time, and you were 11 minutes late today. You will receive one spank for every minute you were late." His voice was commanding, and she was slightly lost in it, only realising once he had stopped that she would be getting 26 spanks today.
As she was stroked and caressed, she looked around; there was no rope that she could see, nor was there a cane, paddle or strap. She wondered what today was going to be like, just as Andy took his other hand and stroked seductively up the back of her thigh nearest him. His fingers seemed to dance; as he moved from just above her knee up the back of her leg to her arse, she felt him caress the fold of skin that defined the boundary between her leg and butt. Then his hand took hold of her cheek, the strong grip making her feel wanted and desired. Chloe moaned, as he massaged her bottom and played, almost tickling as his fingers moved.
Andy stood, releasing her. He then guided her to the coffee table and, instead of leaning on her knees, which was getting uncomfortable, she placed her hands on the table. She stood there like an upside-down U. Andy stroked her soft, smooth arse again, then in a swift movement his hand withdrew and a slap landed across her cheek. Chloe squeaked, but did not even have time to suck in a breath as a second landed on the other cheek. The force of those two had pushed her forward, and she was unstable now, leaning over the table rather than on it. She pushed herself back into place, and her movement backwards collided with the next spank, which resulted in that one being far harder. She yelped, but stood more firmly as several more crashed into her cheeks. She felt the ripple of skin as Andy's hand spanked; she was sure it would be fabulous to watch. But she was also aware that her bottom was starting to sting quite a bit as Andy paused. Ten spanks having landed, he stroked across the red areas of her arse.
Chloe pushed into Andy's hand, as it slipped across her cheeks, moving down between her thighs, and she moaned. The warm touch of his hand made her tingle where, not an hour before, Tim's hot, drunk breath had fallen. She shuddered as his fingers moved back up and grazed across her lips; she felt her clit pop out, the arousal building quickly, his fingers dancing around it. There was a moment she was not sure what he was going to do, then his fingers gripped her clit and, with a delicate force, pulled it out and twisted it. The moan that Chloe felt escape was quite a surprise to her. Electricity fired through her body, as Andy massaged her clit towards an orgasm faster than she would have thought possible. She twitched, and moved, as Andy increased the pressure, her breathing shortening fast, and she found herself almost cumming on the spot. But Andy released her, just at the right point.
Chloe was still calming herself when the next slap crashed into her cheeks, the sting intense, and she yelped, a yelp which still filled the air as the next spank landed. However, she was more ready for the second and she grunted. For ten hits there was a rhythm of a slap with a grunt. By the time Andy stopped on twenty, her arse was glowing with an intense sting that she felt across her whole body. She was steeling herself for the last six, as Andy's hand again started to caress her arse.
Andy's hand moved slowly and gently around her red, and actually quite painful, arse. His fingers slipped onto her inner thigh, causing her to twitch as the sensual feel of his manly hands so delicately played with her soft, warm skin. The tips of his fingers flicked up to catch her clit, making her feel wetter and wetter, as she moaned at each flick. She wanted him inside her, but she didn't think he would do that today. Then he moved his hand and it was covering her pussy, the soft skin, freshly shaven that morning, quivering under the excitement of his firm touch. Chloe was in heaven as she felt the movement from his hand indicating she needed to spread her legs a little more. When she did, one of his fingers twisted and moved to part her lips, the wet redness contained within succumbing to his touch, and she groaned with pleasure.
A finger subtly worked its way to her inner lips, then pushed them open and into her dark wet pussy. It was all she could do not to cum on the spot as he probed into her. his finger slipping in past the knuckle and then back out so slowly, teasing her, as two other fingers moved to either side of her clit and squeezed it between them. The carnal moan was loud, and he had to stop soon; she was starting to fail to stop the orgasm. Her whole body twitched quite violently as the first part of an overwhelming orgasm started, she moaned, "Please stop. I can't hold it."
There was no sound from Andy, but in a swift movement he'd withdrawn his hand from her, moving away. Then, as Chloe started to suck in a deep breath, steadying herself, forcing down the orgasm that was so close, his hand slapped harder than she recalled ever being slapped across her pussy. The scream she let out was full of pain and discomfort; she loved it, wanted another, but she also noticed it had suppressed the orgasm as well.
She almost sobbed the words, "More, please, Master."
It was almost humiliating how quickly he could take her to the brink of an almost uncontrollable orgasm and then remove it, but the complete lack of control over her state was one of the biggest turn-ons she had ever experienced. Chloe wanted him, she wanted him to fuck her, she had waited so long now, been a good student, well...loved being a student. She had never cum the way she had with Andy, and the feelings he created drove her wild, not just while she was with her, but when doing the things he asked.
Chloe's train of thought was broken abruptly as a second slap landed hard across her pussy, causing her to gasp as hard fingers crashed into her soft, pink skin again. Her clit bounced about as the tips of fingers just caught it.
"More, Master. That feels so good,' she moaned, as soon as she could suck in a breath again.
She has not relaxed as a third slap landed; a fizz of pain shot through her pussy. She wanted more, but as she stood, her legs just a little too far apart, Andy moved away slightly. She went to move to see what he was doing, but a command blasted across her from Andy.
"Do not move, slave; your punishment is not finished."
Chloe froze. His voice was a command; not annoyed or aggressive, but a very clear command. She could hear him doing something, then without warning, a cold very hard point pressed into her exposed butthole. There was immediate pressure that made her gasp again, the plug was really well-lubricated, however it was the biggest she had taken. She tried to relax as much as she could; she knew she could take it, certain Andy would not be trying if she couldn't. There was discomfort as her sphincter started to stretch, then the pressure reduced. There was twisting and back and forth motion for a moment. It actually felt quite good, but it was far too short a time before there was more pressure. The plug popped in, her sphincter closing around the thin stem. It felt huge within her, and the jewel end felt like it was holding her cheeks apart.
She calmed her breathing, as Andy stroked and caressed her arse and inner thigh again, brushing across her lips as he moved between her legs. Slaps four and five landed in quick succession, the feeling was different, harder, and more internal, with a sting on the lips. She never dreamed that the butt plug would change the feeling so much; if anything, it was better.
Andy landed the last slap, his hand staying on her pussy, the sting spreading from his hand, but she was done taking her punishment. Her pussy and cheeks were almost on fire; the pain was warming and pleasant. She liked being punished.
Andy's hand moved, playing with her lips and swirling around her clit, her soft skin yielding to his hand. She was completely his to do with as he wanted. His fingers danced across her clit, and the other hand pushed the plug, ensuring it was secure. She moaned, her mind awash with desire for more, for pleasure, for pain, for Andy to take her and use her. As her mind returned slowly to the moment, she felt the pressure on her clit, her desire to cum rising again, her frustration from not cumming for several days, bubbling to the surface.
"Make me cum, Master. I want you; I want to cum. Please let me, Master." Chloe's voice had a very sensual tone; she sounded like a mature woman that knew what she wanted. She had lost that hint of innocence that she had started this process with. She might have struck out to make this happen and knew exactly what she desired, but it was always tempered with that light innocence of an 18-year-old girl who had not really experienced the things she desired. That was gone; while she had much still to learn and experience, she knew what she wanted in a way she never had before, and it showed.
There was more than a graze across her clit. The fingers moved it, the sensations folding into her body, her arousal building, as more fingers disappeared into her, wet and inviting. She thought, I am a slut, as she pushed hard into them, wanting them deeper, but the hand moved with her, stopping her from controlling, and as she re-straightened her legs a slap landed across her arse.
"I haven't tied you, so you can exhibit some control, young lady," Andy's voice was firm, but intoxicating. She swam in his words, wanting to obey his commands, but wanting to cum. She closed her eyes and focused on remaining still, enjoying the pleasure, not rushing into it. He was really dragging this out, though.r"