Hots for the Boss Pt. 04

Lisa moved again on the sofa. It was hard to find a comfortable position; her bottom was stinging, and it was several hours since Pete had punished her, but the welts were there and she was feeling it. Every time it hurt, she smiled. She was loving the pain and discomfort and it was making her pussy wet, it also wasn't lost on her that Pete was smirking when she fidgeted. Her phone buzzed, and when she looked, it was from Al. She read the text: "I have a task for you."

Lisa read it several times, and there was an excitement in her mind as she showed Pete, then replied, "Yes, Master. Pete punished me for what happened today, so I am sore."

"Let me see," came back from Al.

She showed Pete, who immediately said, "Send him the photo."

Lisa pasted the photo that Pete had taken of her red raw bottom and pussy, with cum dripping from it, into the message to Al, and sent it. There was a pause and she watched the three dots animation for what felt far too long. Then a response popped up. She read at the same time as Pete, "Looks like he did a good job. It will not affect the task."

"That's pleasing to hear," Pete said. She thought he sounded smug.

She replied, "Yes, Master, I will carry out whatever you want."

"I know you will," the first part of the response read. Lisa blushed, as she read the rest, "Pete needs to pleasure you for 30 minutes. He can even fuck you if he wants, but you have to hold back and not cum. You may not climax until you see me tomorrow. I expect Pete to try and make you cum though."

While she was still digesting that Pete said, "Fucking Ace!" He grabbed the phone and replied, "Pete, here. She is in for the battle of her life."

Lisa grabbed her phone back and replied, "Yes, Master, as you desire."

She gave Pete a look, one that needed no words for him to know she was annoyed at him. However, she stood up and headed for the door.

"Come on, let's get this done," she said. As she walked away and up the stairs, she was aware that her words had made it sound like a chore but, in reality, she was looking forward to it. Although she was not sure about not cumming. That was not something she had ever tried.

Lisa was naked and laying on the bed on her back by the time Pete walked in. She watched as he paused and looked at her, enjoying the view, she thought. It was not like she would lay naked in the middle of the bed waiting for him normally; it felt a little weird. But even before he had stopped looking, she had formulated a little plan for another day of doing something naughty downstairs, and then being naked on the bed on all fours, waiting to be punished when he got to her.

Pete, stood in the doorway, moving just his eyes. He had focused on her face and boobs, which had cooperated today, and not fallen down the sides, but stayed looking pert and firm on her chest. He was now moving across her belly, which gave her a twinge of self-doubt. She was not fat as such, but she knew she could do with losing about 10 pounds from her belly and thighs. But the moment passed as Pete's view stopped on her pussy. With her legs together as they were, all that was really visible was her silky waxed triangle and her clit, which was excited.

Pete spoke from the door, "Open your legs, and try to touch the corners of the bed."

Lisa complied, her pink and engorging pussy lips now exposed. Her bottom complained with some soft pain as she moved her legs. She waited as Pete watched her, then slowly approached her. He stopped, played with his phone for a moment, then placed it on the side facing Lisa. She looked as he moved away from it; it was on a countdown, from 31 minutes.

As the clock ticked down, he removed his trousers, and his top. Then Pete perched on the end of the bed. He had only his boxers on at that point, and as the clock ticked to 30 minutes his fingers reached out and, with a delicate touch, stroked up either side of her pussy lips. She shuddered with delight.

Pete swirled his fingers on her mons. This had the effect of gently pulling her clit this way, then that, almost dancing under his touch, and Lisa started to feel excitement rise within her—an excitement she wanted to keep at a subdued level, as Pete moved closer and closer to her clit. The swirling circles that he was making with his fingers were just catching the very slightest edge of her clit each time. He had done this once before and it had driven her wild; the anticipation, matched with just enough stimulation, had her arousal climbing far too quickly.

Lisa laid her head back onto the pillow behind her, taking very deep breaths trying to calm herself while Pete applied progressively more stimulation to her clit. To distract herself, she started to think about the shopping list for groceries this week, but she could not stop the whispered moan that escaped her lips as Pete's finger glided across the top of her clit. She was listing out the vegetables she needed to add to the list, trying to avoid phallic objects like banana, cucumber and carrots when Pete's fingers slipped away from her clit. Then, as they plunged into her soaking pussy, his tongue pressed directly onto her clit. With a groan of pleasure, Lisa's hands shot to Pete's head, pushing him away, but he pulled her in, fighting her struggle to get away. With his fingers now pressing quite hard on the outside wall of her pussy, she could feel the uncontrollable feeling of an orgasm rise within her.

She looked at the countdown, it read, "22.13". As she softly said into the air with all the will she could muster, "No, Pete. Stop! I can't hold it." Even as she said it, she was tensing her body trying to push down the feeling.

Pete ignored her, pushing his tongue harder and harder into her clit, squashing it against her pubic bone, and pushing up hard with his fingers inside her. She thrashed from side to side, and tried to bounce him away from her, but with the spare arm he had a grip on her that she could not shake. Lisa felt her muscles spasm; she was charging at the orgasm that she was not allowed to reach. Her body was betraying her as her mind fought for control, to quell the physical reaction, but it appeared to be in vain as she felt her arousal jump up again, a moan escaping her lips.

Pete slipped his tongue into that fold of skin between her clit and the lips that covered it normally, then traced the outside of her clit. She shook; as much as she fought, an orgasm was coming. Pete was pushing her over the edge. But he stopped, let her body settle. She gulped down large swallows of air, calming herself, fighting back the waves of pleasure that were all but about to overwhelm her. As she thought her breathing was back under control, Pete pushed his tongue back into her clit, making her scream out with desire and lust, wanting to cum, but simultaneously not wanting to cum. She was moving about a lot, fighting Pete's grip on her as much as the orgasm that was just under the surface. She saw the clock again out of the corner of her eye: it read, "16.47".

Her mind focused, she was almost halfway there, but she was also on the edge of failing. Pete was in a rhythm, bouncing her clit like a ball, but to a regular pace that slowly increased and then slowly decreased. On the increase, she felt more flustered, more like she would fail, her body slowly becoming more tense. Then, as it decreased, she felt the tension subside—just a little, but enough. Pete continued this pattern, and while the general trend was getting her closer and closer to an orgasm, she was able to control it. Lisa tried not to think about his tongue as it tracked across her clit, bouncing it from side to side, or the fingers that were gently tracing her lips from her arsehole up to her clit and then back again, flooding her body with gentle tingling sensations throughout.

Lisa's general sense of arousal was increasing by the minute. She was starting to feel frustrated at not cumming; she wanted to release the tension that had built within her sexual organs, and even her tits seemed to want to be touched to send her over the edge. She realised that Pete wasn't trying to make her cum any longer, but to hold her as close to cumming as humanly possible without her actually climaxing. It was starting to drive her mad. She looked at the clock, "07.02." Lisa started to believe she could do this, although Pete was not really holding up his end of the bargain.

Fingers slipped back inside her. She wanted cock now, but Pete was in control, and really cock would have had her fighting herself not to rub to an orgasm. Pete had his lips around her clit and was twisting it, ever so gently, but enough to make her tense. He quickly took her back to the point where he had stopped before, where she was convinced that an orgasm was inevitable. However, this time, she was more certain she could avoid it, and Pete didn't stop. With the fingers insider her, pushing her G spot, she convulsed as she fought the climax, and was convinced she could win. As she shook again, Pete stopped, and let go. The only sound in the room for a moment was Lisa's quick laboured breathing. There was a moment when she thought it was over, but Pete moved, then his cock was in her, thrust in hard and fast like earlier, and as she screamed out her desire to cum, she grabbed the pillow and pulled it with both arms over her face, and screamed in frustration into it, instead.

She heard the timer on the clock start beeping; she had made it and wanted Pete to stop, but he didn't. He pounded on her driving the desire to cum higher and higher, her level of frustration with it. From under the pillow, she shouted, "Stop, I can't take it."

There was no letup and she pulled the pillow away to glare at Pete, but he kept pounding. She wanted this to end. She had been successful and needed him to stop, but as her hands came toward him, he grabbed them, holding her tight, as he thrust into her. "Almost there," he said, as she fought. Her frustration with Pete was actually reducing the desire to cum, and her arousal too. He stiffened and pushed hard into her, his seed hit her, but it was much reduced, this being the second load in only two hours.

Pete let go and walked away to the bathroom. She was furious with him, but as she lay there she was also pleased. She had managed it, albeit Pete had helped her a little. She considered for a moment, then decided that she better tell master about that, and as she calmed down, she realised that there was a much-heightened desire to cum in the background.

Before Pete had returned from the bathroom she said, "Right, now we need to talk." She paused, then in a more forceful tone said, "And if you ever do that to me again there will be trouble." Pete reappeared looking a little sheepish.

The conversation that followed that moment was replaying in Lisa's head as she walked back into the office the following day. Lisa admitted that she was getting more and more turned on by the idea of being punished, but actually wanted more punishment when she was being punished. She had yet to experience the level of pain that made her want it to stop. She also admitted that she liked not being in control, which created a little argument about Pete not stopping, but she made clear there was a difference. What she didn't really admit fully to Pete was the fact, she kind of liked the humiliation of it, too.

Pete, for his part, had been very upbeat. He said he had not really thought that much about S&M, but that he was really enjoying the spanking, and wanted to try lots of other punishments for her, too. Hot wax and ice were mentioned; then he said he would have to do 'research'. Right at the end he blurted out that he wanted to watch her with other men, that he loved the idea of being made, forced even, to watch her pleasured by a man or men. He was bright red when he said it, and it did not completely sit right with everything else he had said, and Lisa thought there was something more to be explored there, but Pete would need to open up more first.

She sat at her desk, in a skirt that she would normally only wear on a night out, with no knickers on—something she would never normally do. She started work, and cracked on for a good hour before Al appeared and took a desk. He sat two desks along from Lisa, with nobody else in the little section they were in. Friday in the office was so quiet. They were in a corner of the office, not concealed, but not in a place anybody would walk to unless they were coming to speak to one of them. It was perfect for a private chat, or something more intimate, if she was very careful.

About 10 minutes after Al arrived, when he was just doing a report and not on a call, Lisa stood and moved to a position next to him. She was careful to select the spot. Desks and monitors would hide her from everybody else she could see in the office, unless one of them stood, or walked their way. She made sure Al was watching, then as she had before in the lift, touched her toes, giving him a full view of her naked bottom and pussy. She was aware of the redness in her cheeks from the previous night, and she felt very exposed at that moment. She held completely still, waiting for Al's instruction, praying that nobody walked in their direction as she would not see them in her current position.

As she stood there, Al's hand came across and stroked her red cheeks, then down and around her pussy. He played for a moment, then his fingers slowly parted her lips and worked their way inside, as she moaned quietly.

As he fingered and probed deeper, Al asked, "So, tell me about the task last night."

With her head by her knees, she replied, "We completed it; I didn't cum." Her words were clear, but she knew her voice was betraying that she was not telling the whole story.

As his thumb pressed into her clit, she shuddered. He said, "Go on."

Lisa composed herself, beginning to feel very aroused, "I got very close to cumming, and Pete had to back off, or I would have failed. He held me right on the edge for a good 15 minutes."

"So you failed," he said, as he pressed hard on her clit.

"Yes, Master," she replied. As the words left her lips, Al bounced her clit under his thumb making her shake.

He withdrew his hand, leaving her body wanting more, much more.

"Stand up," Al said, and she complied and turned to face him. Once she was, he continued, "I knew you would; I have a punishment for you."

Lisa watched as Al reached into his bag and pulled out a butt plug. Lisa knew it was not that big as they went, but it was far too big for her delicate little bottom, that had never had anything up it. Al passed it to her, then a small tube of KY jelly. She looked at them in her hands for a moment, then back at Al.

"Go and put that in now, and then come and show me. You will have to keep it in until lunch." As he spoke Lisa's eyes darted to the clock, it was 9:50, which meant it would be in there over 2 hours!

"Yes, Master," Lisa said, although what she wanted to say was, "No fucking way!" But she kept those words inside, and started to walk towards the toilet, hiding the items in her hands as she went. She sat inside the toilet for a moment; the idea of this did not appeal at all, but she was determined to do it. She squeezed some gel onto two fingers and reached for her butthole. The gel was cold and made her flinch as she made contact. For a good thirty seconds, she rubbed around her brown star, then tried to relax. She slipped a finger inside. It went in easier than she expected, and she moved it about for a few moments. It was not comfortable, but it did not hurt either. After ten seconds or so, she pushed the second finger in with it; that was uncomfortable, but she kept moving them and spreading the lube. When she had been playing for about a minute, she removed her fingers and wiped them on toilet paper. She looked at the butt plug, turning it over and over in her hand. It was metal—stainless steel she thought—clearly an item of quality, and a little heavier than she thought it would be. The end was deep-red coloured glass.

Lisa took a deep breath and let it out slowly, trying not to tense. Then she placed the point against her arse—no pressure, just in the right place. She took a breath and let it out slowly again, and as she did, she pushed. The plug slipped in; it felt like a long way, but when she moved her finger to see, it was about 2 cm at most. She held it where it was, breathing carefully for a moment, then as she relaxed, pushed it hard. The discomfort was intense, but it moved a lot. She held it still again; it was about three-quarters in. It was not a nice feeling, and she let it out just a bit. For another minute she sat, relaxing and breathing steadily. When she felt ready, she pushed, and felt it slide up. It kept moving at a slow rate. She was breathing through it, then it popped. The pressure on her sphincter was gone. No, not quite gone, but reduced. She felt around; it was in place, just the end sticking out. She let out a sigh of relief.

Lisa stood up. The feeling was strange; she really didn't know how to describe it. Then, when she walked out the cubicle and into the main toilet it was uncomfortable. She took a moment to compose herself, then exited and walked back to her desk. She was sure she was walking normally, but had a fear that it was obvious she was walking with a plug in her butt. This was punishment; she did not like the feeling at all, and thought the next 2 hours or so would be hell.

There was another senior manager with Al when she got to her desk. She hid the lube and got on with a report, waiting for him to leave. They were talking quietly and she could not overhear, but felt like they kept looking over at her. Then, on the third time of feeling it, she looking over and locked eyes with the lady talking to Al. Lisa looked away quite quickly, but she felt like the eyes were boring into her.

"Lisa, can you please come over here," Al said.

Lisa stood and walked over. As she got there, Al said, "This is Sophie. She heads up our internal customer service. I was just telling her all about you."

Lisa blushed heavily, but managed to say, "Nice to meet you, Sophie," before looking away.

"Sophie and I have known each other for years; for a long while she followed my instruction." Al had an air of amusement in his voice as he said it, and Sophie outright laughed when he said that. Lisa was not getting a good feeling about this at all.

"You mean she worked for you?" Lisa said, hoping the answer would be yes, and that would be that.

"I did, but I also followed his precise instruction and was punished when I didn't," Sophie said. Lisa's heart sank, as Sophie continued, "As you are doing now."

"Turn around and touch your toes Lisa," Al said.

Reluctantly Lisa said, "Yes, Master," and turned and bent over. She had to pause halfway down as she thought she may push the plug out. She got control and completed the action.

"Oh, fabulous! Your arse is a lovely pink," Sophie said.

"Wasn't me, unfortunately," Al chipped in.

"Do tell," Sophie purred, as her fingers came across and wiggled the butt plug a little; it was not at all what Lisa needed.

"My husband punished me last night for taking my knickers off for Al," Lisa said.

"Oh, so you are juggling two Masters," Sophie said. "That must be a challenge."

Before Lisa could say anything, Al responded, "It will not be. She will be fully compliant."

Despite everything, Lisa was starting to get turned on. This whole situation was surreal, but also sexy. A woman only about 10 years older than her was looking at her pert arse and wet pussy, and had played with the butt plug in her arse. She was not sure this should be a turn on, but it was.

"You can stand and return to your desk now," Al said, then added, "If she wants to, at some point in the future, Sophie will spank you."