Monica's Affair

"Yes Sir, I got it. It's all done. We're looking forward to it as well. I'm just working out the final numbers and allocations of rooms for the retreat. Yes Sir, almost done, within the hour, yes sir," he said into the phone. He quickly said goodbye and sighed and looked at his young subordinate.

"I assume you gathered the sense of urgency from them hearing that?" he asked her.

"Yes, I did," she replied. "They want everything finalized within the hour?"

He nodded, "Yes," and looked at his Rolex. "Which gives us about 45 minutes to get this done. Please tell me you talked to your husband. One way or another, I need to get this done, like now."

She shook her head. "No, I'm sorry Jake, I didn't get a chance. I tried several times last night and today but Sarah is sick and Rick's at the hospital with her, so it's been kind of chaotic."

"Oh God, I hope she's ok? Anything serious?" he asked, and looked genuinely concerned.

"I don't think so, probably a bad fever or something, but hopefully he'll let me know soon. Thank you for your concern," she answered.

"Of course, family comes first around here, you know that. Well if you have to leave or anything, feel free," he reassured her.

"Thanks, I'm ok for now. Um, but uh, I think you may as well go ahead and put us together, and just be done with it," she said, and shifted nervously in her chair. She couldn't believe she suggested it, it just came out. She didn't want to make this decision without Rick, but honestly felt it was for the best, for everyone.

Jake looked at her surprised. "Really? You're ok with that? I don't want to cause any turmoil with your husband. Are you sure?"

She nodded slowly, "Yes, just get it over with and do it. I tried to talk to him a few times, and I'm so stressed out about it I just want it over. I think he wouldn't like it, but he doesn't know you like I know you and I know you only proposed this for the sake of making things easy with senior management, and not for any bad reasons. The more I think about it, the more I think it's fine to do."

He smiled slightly. "Ok, if you're sure. I don't want this to be a problem at all, but it would make things much easier. You sure?"

"Yes," she stood up and tried to sound convicted, though inside she felt very apprehensive about the whole thing. "I'm sure, it'll all be fine."

"Ok, great then, thank you," he stretched out his hand to shake hers. She took his hand and he shook hers and said, "Roommates for 5 days, I'm glad honestly it's with you and not someone I don't know."

"Me too," she said shaking his hand from across his desk. He thanked her again and she said goodbye and went back to her office.

Sitting at her desk, she immediately second guessed her decision and wrestled internally with what she should've said. But it was done, she wasn't going to go back. Now she had to decide what to tell Rick. The thought came into her head to not tell him at all, but she felt sick to her stomach entertaining that thought. She felt like she was being deceptive, trying to hide something. She made up her mind that she would tell him tonight, and it was done, couldn't be changed now without significant trouble, and hopefully that would make him a little more open to the idea.

The same thing happened as earlier, one thing led to another and she just didn't have a good chance to talk to Rick about it. Maybe part of her was terrified and she was subconsciously avoiding it. 24 hours passed, and she still hadn't done it. The more time that passed the more she felt like it wasn't even worth telling him now. It was done, there was nothing that could be done to change it now without significant difficulty. And besides, she had no intention of doing anything inappropriate with her boss, it was only sleeping in the same bed and purposely avoiding each other as they did so.

Time passed, she kept making excuses to avoid telling him, and eventually decided not to. The more she thought about it the more she convinced herself it was no big deal. And she knew it would be a very stressful and awkward conversation with him, but she also felt he had absolutely nothing to worry about, so it seemed unnecessary to raise it anymore.

The trip was only a few days away and the last couple of weeks had kept her incredibly busy with life stuff. She had no time to go shopping for new pyjamas but decided she would just wear a pair of shorts and a long t-shirt over her bra and panties and that would suffice and be appropriate. They had a lot to do with helping out and taking care of Grandma, and the kids more so than normal, and she was just run ragged for several days in a row. She was actually looking forward to this trip to get some relaxing time.

So Monday morning came, and off she went, saying goodbye to her family for a week, kissing the kids, and kissing her husband deeply, and committing that she would call every night to say good night.

Her drive was uneventful, the roads were good and she made excellent time. As she finally pulled into the remote resort in the woods, she saw the cabins, all exactly alike, lined up along a beautiful lake, with a main building much bigger off to the side. She proceeded to cabin 17, which she knew was hers and Jake's for the week. It happened to be situated right on the side of the main building, and as she pulled up out front she saw her boss's car nearby. He actually came out of a side door of the building just as she was pulling up.

"Oh Hi, how was your drive?" he asked as he walked up and hugged her.

"Oh fine, no troubles. Actually crazy stress with the family lately so I'm looking forward to some relaxation here," she replied.

"Good, that's great, I'm sure you'll get it. Hey I'm glad I ran into you now. I just got here a few minutes ago and haven't even been in the room yet. I have to head to a senior manager meeting right now inside. Here's the keys, why don't you go settle in and I'll catch up with you later," he said.

"Ok sure," she nodded, taking the keys. And they said goodbye and he went back inside and headed to his meeting. She grabbed her bags and headed to the cabin. She opened the door, smiling, happy to have some down time to herself. She walked in the front hall, put her bag down, and walked in to check out the room. As she rounded the corner into the main room, she suddenly gasped, dropped her bags on the floor and clasped her hands over her mouth.

She couldn't believe her eyes! The bed was what she was staring at, but it was not a king sized bed, it was a twin bed, a double, and way too small to share with her boss! She thought a mistake must have been made, and she felt incredibly anxiety as she thought about the possibility of having to share this with Jake for a week. She thought about the nights in the bed and then it suddenly hit her.

"What the hell am I going to do?" she thought. She knew with this bed, even if they stayed on their own sides, if either of them rolled over in the night or stretched out a limb, they would be touching each other. She wondered what Jake wore to bed. For a moment she found herself thinking of his penis. She had never seen another man's since she met Rick, and the thought of it touching her at night, on any part of her body made her shudder. It was so wrong. In this bed, it would be very easy for them to end up in any number of compromising and inappropriate positions in the morning when they woke up. She was so nervous and scared and upset that she didn't realize in there as well was a hint of excitement at this situation. She didn't realize at the time that those thoughts made her a little wet, a little turned on.

She sat there crying for several minutes. She intended to go to the front desk and sort this out, but she was more upset at herself for not telling Rick. She was regretting it now. Eventually, she collected herself and knew she had to sort this out, and headed to the front desk in the main building. Once there, she asked immediately for the manager, who was summoned and came shortly out of an office to greet her. She explained the situation briefly, without going into a lot of detail, and told him that her and her boss were sharing a room for the week, and it is completely platonic, she is married, and only for company business reasons. There was supposed to be a king sized bed and it's only a double and won't do.

The manager was very empathetic and checked the computer and realized a mistake had indeed be made, and their room was instead given to one of the top brass from the parent company. After a long talk and pleading and grovelling, she was left with the reality that the place was packed full, there was nothing that could be done without significant professional embarrassment to her and Jake, and she didn't want that.

She sat down into the chair and felt like she was in a bad dream. She glanced at her watch and realized she had to put this on hold for now, as there was a meeting she had to be at shortly. She changed, got ready and headed out to the meeting, trying to put this out of her mind for now.

A few hours later she was finished her meetings and saw Jake in the hallway.

"Jake, Hi, do you have a few minutes? We NEED to talk," she sounded desperate. He glanced at his watch and replied,

"Yah, I have a few, sure, what's up?"

"Our room," she replied, "have you been there yet?"

"NO, not yet, I've been in back to backs all day. Is something wrong with it?" he said.

"Yes," she replied emphatically, "Very wrong. It's not king sized bed Jake, it's a twin only. A twin! "

He looked surprised. "What? Really? How? Did you talk to the manager? That can't be!"

"Yes," she nodded, "I had a long conversation with him. It's a mistake, and Kyle Jenkins has our room. They switched them by accident. I didn't think we could very easily ask him to switch with us."

"No," he said, "We can't. He's kind of an asshole on a good day, he would be quite pissed if we did ask him. I'm so sorry Monica. It will be a very, um, awkward situation I guess, for us, right? But I can make the best of it if you can?" He looked sincere.

"I don't think we have any other choice," she said, but looked very upset.

"I agreed with you," he said. "But Monica, we are both professionals, and have great respect for each other, and I think we can make it work, don't you?"

"Um, yah, I uh, guess so. I guess it's all we can do," she replied.

He saw how upset she was with the whole thing and hugged her. She shuddered slightly which she had never done from one of his hugs but this time she felt vulnerable. He thanked her for her flexibility and said he had to go to another meeting and they said their goodbyes.

She had some time free now and made her way back to her room. She tried to keep busy and keep her mind off of this crazy inappropriate situation and she hung her clothes up in the closet. She left all of her night time and skimpy clothes in her suitcase, as she did not want them in a drawer that he might access and see.

When she was done she had a bite to eat and another meeting so she headed back to the main cabin. It was a beautiful evening, and she felt a little better about the bed situation, and was confident they would make the best of it.

Her meeting was a couple of hours, and then she headed back to the cabin, and upon entering saw Jake there, sitting at the desk, on the phone and on his computer. He waved to her and went back to his call. She knew she had to be relatively quiet with him on the phone, and as she took off her shoes she noticed a man's tank top laid out on the bed and assumed it was his. It was quite ratty and had some holes in it and looked very old and thin. Beside the shirt was a note. She walked over and read the note.

"Monica, one thing I forgot to mention earlier, is that seeing as how I'm your boss, I'm in charge in this room. And I have rules in this room that you must follow, that are non-negotiable. The first rule is sleeping attire. This shirt is your sleeping attire. You may wear it and only it to bed. Nothing underneath it is permitted. If you break this rule, you will be punished. This call I'm on will last quite some time, so you are to shower and put on this shirt and go to bed shortly. Again, this is not open for discussion." Jake.

She stood there staring at the note and re-reading it several times. 'This has to be a joke,' she thought and looked over at her boss a few feet away. He was ignoring her and looking at his laptop screen and talking into his headset. She walked over into his sight line and waved to get his attention. He glanced at her quickly, and she held the note up and silently mouthed, "What is this?" to him and pointed at the note. He smiled devilishly and went back to his meeting, leaving her without an answer. She stared at him for a long time but he ignored her, and finally she walked back and sat on the bed.

At first, she thought it was funny, convinced it was a joke. But now seeing his reaction, she was beginning to think he was serious. She looked at the tank top and it was low cut, and pretty short too, she didn't think it would even fit him properly. Either way, there was no way she was wearing just that to bed. Not after all of their talks about respect and dignity and sharing a bed. Now she was beginning to think he arranged this bed on purpose. She was questioning everything she knew about him and if he could be trusted after all. And the fact that he expected her to obey with no discussion was the worst of all. She was not some toy, or his property. Now she felt angry. Several times she glared at him and wanted to go over and hang up the call, but she knew that would be very bad. He was still her boss after all. She wondered what he meant by being punished if she broke the rule. Was he going to fire her? She was worried now and felt anxious again. She sat for a long time and didn't move, determined to wait him out so she could talk to him.

After an hour she got very tired. She was stewing and worried about what to do. And he didn't seem any closer to ending his conversation. She decided she would wear his stupid shirt, but she was going to wear her panties and bra under for sure. She went into the bathroom, texted Rick, made up some excuse about not being able to talk, said good night and hopped into the shower. She had a long shower, on purpose trying to wait him out, came out eventually in her towel, and he was still talking away. She sighed and grabbed the shirt off the bed forcefully, and went back into the bathroom and put back on her bra and panties and the shirt over top. She looked in the mirror and was glad for her panties because it was short, and only covered a few inches below her thighs, not even her entire butt was covered, and she was barely covered in the front, and movement at all exposed her panties.

She came out of the bathroom and shut all the lights off except the one on his desk, and climbed into bed and hugged the edge and turned her back towards the other side. She cuddled up under the covers and wanted to forget this whole stupid thing and in the morning she would have a few choice words for him, boss or not. She was very tired and fell asleep shortly.

She woke up slowly, and felt Jake spooning her, pressed up against her hard. His right arm was around her waist, his left arm he had managed to get under her and was wrapped around cupping her breast through his shirt, and his penis was pressed hard up against her butt. For a moment, out of instinct, she squirmed, and pressed back up against his manhood. It felt good, but she wouldn't admit it to herself. Then she realized how inappropriate this was and tried to move his arm so she could get out of bed. As soon as she did he spoke.

"Oh, hi, you're awake finally, good, get up," he said, and released his hold of her and got up himself quickly. As she got out of bed she saw he was only wearing his boxers, and even flaccid, his penis was very large in his boxers. She glanced at it a few times by accident. He was very fit and toned for a man of his age, much more so than she thought. He walked to the desk and pulled the chair out and held his hand to her.

"Come," he said calmly. She walked over slowly, not sure what this was about, and apprehensive to trust him after the whole shirt and being naked under note.

"Jake, I want to talk to you about your note. It's highly inappropriate..." as she said that last word she was in front of him and quick as a cat he grabbed her arm, sat down in the chair and pulled her hard over his knee. She fell forward and had to use her hands to brace herself on the floor.

"Ohhh, stop, what are you doing Jake? Let me up!" she exclaimed and struggled to get up off of his knee. He held her down with one strong hand and lifted his shirt slightly to expose her entire ass. "SMACK!" went his hand down on her butt.

"Owww!" she cried out and put her hand back to block him.

"Monica, leave your hands on the floor or I'll tie them behind your back!" he instructed sternly and spanked her butt again.

"Owww! That hurts! Stop it . Jake what are you doing? Why are you doing this?" she reluctantly kept her hands on the floor.

"Monica, I gave you very clear written instructions with regards to your bed attire. What did I tell you to wear?" he said, and spanked her ass again.

"OowWWWW!" she cried out.. "Oh my God stop.. you, you said to only wear this shirt and nothing else!" she said back sarcastically.

"That's right, and I said if you did not do it you would be punished. You defied me, so now you are being punished," and he spanked her ass again hard. She squirmed and shook on his lap and she felt his cock growing hard against her thigh as she did, and she could tell it was very large.

"Jake please, stop... it hurts. I couldn't go to bed like that, I would be practically naked. We talked about that, and how in...owwwww! owwwww!" she was cut off by him spanking her hard twice and crying out in pain. She had tears in her eyes now and felt so humiliated. She had not been spanked since she was a little girl. She felt helpless as she squirmed on his lap.

"Do not protest or try to justify your defiance Monica. You may only apologize," and he grabbed her panties and yanked them down to her knees, exposing her bare ass. He put his hand on it and rubbed the cheeks softly, which were turning red. She put one hand back quickly and tried to grab her panties to hold them up. He grabbed her wrist and held it firmly behind her back.

"Jake please, don't do this, let me up!" She could not move her other hand that was supporting her weight on the floor or she would fall forward. She felt helpless and vulnerable with her panties down to her knees and being exposed to her boss like this.

"Smack!" came his hand across her bare cheek. She cried out and shuddered again.

"Apologize!" he said and smacked her ass again..

"Oww! Oww!! Ok , ok, I'm sorry. I'm sorry I didn't do what you told me to. Please stop!" She felt his cock pressing hard against her thigh now and it was very erect in his boxers. She shuddered a little and was embarrassed and disgusted with herself to feel that her pussy was slightly wet. She felt so humiliated and helpless and her ass was on fire with pain from his hard spankings. She didn't understand why this was making her wet.

"You've been a bad girl in defying me Monica, and you deserved to be punished!" And he spanked her again twice, once on each cheek. "Say it!"

She cried out and bit her lip from the pain, and felt she would say anything he wanted right now to make him stop spanking her. She said softly, "I was a bad girl and I deserve to be punished." She felt so humiliated and wished she had told Rick and he had forbid her from sharing a room with Jake.

Another two smacks on her perfect, round, smooth ass and it was red and throbbing. She was crying now and begging Jake to stop.