Reluctant Proposition : Ch3

Sitting back into my chair, I kicked my feet up on the desk and relaxed a little. Work was usually quiet after lunch, so I could take a moment to myself. Sipping on my coffee and looking over the apartment, I realised just how good I had it.

Sure my job wasn't paying great money now, and the workload could be oppressive, but I had a career. I had the opportunity to learn and grow, a path to follow that would shape my life for the better.

But more important than career or financial success, was my family. Supportive parents who looked out for me, the most beautiful loving caring woman on the planet for a girlfriend, and an amazing mentor who was the reason I had all of these good things in my life.

Maybe not directly, but Mr. Thompson was the reason I was the man I was today. It was weird to think back on now, but he overshadowed my own dad when it came to father figures in my life. My own dad was a nervous, passive man. Not a confident and sharp figure like Mr. Thompson.

Maybe that was why I wanted him and Jamie to get along so much? I never once worried about introducing her to my parents, I knew they'd love whoever I chose as my partner. But Mr. Thompson's approval didn't come so easily, especially in a professional setting. Sure he was fond of a good joke or even a light-hearted prank, but when it came to business? The man was all business.

“I'll make sure to have a more suitable pair for you tomorrow.” Mr.Thompson scoffed as he walked out of my room. He saw me staring and raised his eyebrows. “Working hard, are we Michael?”

“Uhh… Just thinking through a problem, sir!” I put my legs down, but before I turned back to get stuck into work again, I noticed something.

“Are those Jamie's panties?” I stared at the object in his hands. The lacy black panties that Jamie had been wearing moments ago, wrapped around his fingers.

“Evidently they weren't the right pair.” Mr. Thompson scoffed. Walking out of the apartment in a huff.

Jamie stepped out when he was gone, rubbing her butt cheeks like they were sore.

“What happened?!” I asked her.

“I don't know, I… I thought I was polite.” Jamie's eyes were wide, she held her arms to her chest and was rubbing her shoulder.

“I've never seen Mr. Thompson look that upset. What did you say to him?” Anger, disappointment, regret. I'd seen Mr. Thompson experience all of those emotions, but never once had he visibly shown signs of being hurt.

“I was just honest!” Jamie sat down on the couch, signs of stress clear on her face.

“About the panties?”

“Yeah.” Jamie shook her head in disbelief. “He was touching them, asking me how they felt.”

“Wait, was this before or after they came off?” I asked.

“Before.” Jamie blushed. “He was spreading my… my butt cheeks open with one hand. Then with the other he ran his finger over the panties.”

He ran his fingers over them? Spread her ass open? She must have just meant touching around the band of her panties, and I doubted he was actually spreading open her cheeks. Mr. Thompson wasn't the type of guy to touch a girl inappropriately, I knew him well enough to know that. Jamie wasn't used to the special way he measured people, so she must have just misinterpreted some of his actions.

“I could feel him over both… well, you know.” Jamie kept blushing, too shy to say the words ‘both butt cheeks’. Something that tame didn't normally leave her so flustered, but today was a stressful day.

“It didn't feel bad, but it didn't feel… right?” Jamie continued. Gathering her thoughts as she spoke. “But I remembered what you said, about his methods, so I let him do it.”

“That's good.” I nodded. “So what went wrong?”

“Well he was asking how they felt right? So I told him.” Jamie bit her lips. “I told him they were too small, that they barely covered up my… my you know what's”

She was right about that. The tiny pair of panties weren't quite a thong, but they didn't offer full coverage of her ass cheeks.

“And he didn't like that?” I guessed.

“He got real quiet for a moment, and then umm…” Jamie looked at me for a moment and then broke that eye contact. “He told me he needed me to bounce up and down so he could see if they fit right.”

“I would never have even thought of trying that. He can be so clever.” I could be his student for another twenty years and I still wouldn't be able to think outside of the box like Mr. Thompson does. “So did it work?”

“I wasn't doing it right at first. I thought jumping on the spot would be good, but he showed me a better way.” Jamie stood up and faced away from me. She got into a squat position and arched her back forward, sticking her skirt covered ass out.

“This still isn't right. Ughh.” Jamie groaned in frustration. “He had to move my thighs into the correct position, and helped me place my butt in the right spot, but you get the idea?”

Jamie started wiggling her ass up and down. Shaking it hard enough to make her cheeks slap together in a clapping sound, her skirt flapping like it was in a hurricane. The frantic motion keeping me from getting a clear view under it.

“I see what he was doing.” I nodded as Jamie finished performing her test and sat back down. “Having you stick your ass out and shake it to maximise the amount of force exerted onto your panties.”

“Yeah… that's what he said it was for…” Jamie looked a little nervous, or unsure. That was the problem with being a creative thinker. People like Jamie who were conditioned to listen to instructions and do things by the book were usually slower to accept a more eccentric solution to their problems.

“So I take it you failed the test?” I asked her.

“No, I ‘passed’.” Jamie put the word in air quotes. “Although he said we'd have to work on my technique… But I told him that the panties being too loose wasn't the issue! They were too tight!”

“And that's what made him mad?”

“Yeah, I guess. He uhh…” Jamie's eyes fluttered away from mine. Her cheeks turning redder with every word she spoke. “He told me that if I still didn't like them then I should just take them off.”

Huh. That wasn't so bad. Seemed like a practical solution to the problem.

“Did you take them off?” I asked, before catching myself. “Sorry, of course you did.”

“I didn't actually.” Jamie's eyes were locked onto the floor. Her hand covered her mouth while she spoke. “He did.”

“Mr. Thompson took your panties off?” I asked. Almost in disbelief.

“He just started pulling them down while his hands were on me.” Jamie admitted. “He took it really slowly until he was past my thighs. Then he took them and rubbed them on his nose…”

“He was checking to see if they needed to be washed.” I told her.

“That's… that's exactly what he said…” Jamie said. Almost sounding shocked.

“Another one of his skills. He can always smell if a woman's panties are ‘fresh or used’, as he would say.”

“Isn't that like… something anyone could do?” Jamie questioned.

“No, it's.. It's different.” I tried to explain it, but I didn't quite know how to. “He and mom played that game all the time, and he never once lost. That's a skill!”

“Okay, umm… well…” Jamie looked a little lost but kept going. “He was sniffing them for a while, and I don't know if I mentioned it but he made me lift my skirt up for him earlier.”

She hadn't mentioned it earlier and I wasn't sure why she was mentioning it now. Mr. Thompson would have been busy determining if he needed to get the panties cleaned or not before returning them. He wasn't going to be staring at her exposed body.

“But what upset him? Surely it wasn't just that?” I interrupted Jamie, just a little, to ask the question. I didn't want her getting off track with pointless information. Mr. Thompson would be expecting her to go back to work soon.

“There's more…” Jamie said, as though she was admitting to some mistake or betrayal. “He, umm….he spanked me.”

“He spanked you?!” I gasped.

“He said that because I wasn't wearing my full uniform I needed to be punished.” Jamie gulped. “He was just going to dock my pay, but he said he knows how much we need the money, so he had a different solution in mind.”

“So to be kind he spanked you instead?” I nodded. “That makes sense.”

“It does?!” Jamie exclaimed.

“As much as anything about him does.” I explained. “Clearly he took the uniform thing personally. I think he hand picked your clothes, and was mad they weren't perfect. Probably more mad at himself for getting it wrong than at you for mentioning it.”

“I think I can understand that.” Jamie's forehead creased as she thought. “But the spanking?”

“He's a very rigid, hard man. In his mind, even if it was his mistake, you were the one breaking the rules by being out of uniform. Therefore you needed to be punished.”

“But-”

“I know I know. That isn't fair.” I reassured her. “But that's just how he sees it. As for why he chose spanking? Well, he's old. It was a normal, everyday occurrence when he was growing up. He doesn't get that it's different now.”

“I suppose…” I could see the gears turning in her head. How she was beginning to understand how he worked.

“He didn't spank you hard? Did he?”

“No. He was gentle.” Jamie nodded, her body finally starting to relax. “He sat on our bed and had me bend over his lap with my skirt still pulled up. He spanked me five times on each cheek, but it wasn't five times in a row.”

“See? It was more symbolic than punitive.”

“He gave me one spank and then kept his hand on me. Rubbing my body, to sooth me I guess…” Jamie was picking up confidence. Speaking more normally. “Then when he was done with all ten, he got up and left.”

“I think there's nothing to worry about then.” I told her. “I think if you apologise for what you said, and thank him for the spanks, then this will be something you two laugh about years from now!”

“I have to thank him for spanking me?” Jamie asked. Confused.

“It was kinder than docking your pay like most bosses would. And he didn't have to be gentle with you, that was nice of him.”

“Yeah, I guess you're right.” Jamie was feeling confident enough to look at me again. Her innocent, pure smile infectiously spreading to me.

“You should also let him know you're happy for him to spank you whenever he wants to!”

“Whenever?” Jamie clarified.

I knew how clumsy Jamie could be. I knew she'd get herself into trouble again. We really, really needed the money from this job. I was worried Mr. Thompson would think she wasn't comfortable with the spanking. That he might dock her pay next time. But if he knew she was happy to receive discipline in an alternative way, then I knew he'd pick that instead!

“I know his way is old fashioned, but you've got to play by his rules while working under his roof!” I explained. “So why don't you go back now and tell him you're sorry. I think it'll really make him respect you!”

“Okay!” Jamie stood up. Looking energised after my pep talk. “Let me just put some new-”

“There's no time for that! He's waiting for you right now.” I gestured for her to hurry. Whatever new bit of make-up or whatever she wanted to put on wouldn't be worth the time.

“Are you sure?” She asked. Hesitantly looking at me. “You're okay with me going as is?”

I looked her over. Wondering if there was something I might be forgetting.

Nope. She looked fine to me. Her clothes and make-up all looked good. I wasn't sure what the problem was. Just nerves I guess?

“You're fine baby.” I blew her a kiss. “Now go have a great rest of your day!”

“Okay! Love you! See you when I get home!”

“Love you too!” I said as she left. Leaving me alone in the apartment once again.

I leaned back in my chair again, cracking my knuckles. A wave of relief rushing over me.

Another crisis averted. Man was I good.

***
Work calmed down even more into the afternoon. Nearing the end of the day I found myself with nothing to do. Normally I would message Jamie in a moment like this, but I didn’t want to distract her on her first day. I knew Mr. Thompson would be keeping her busy, working her hard. It almost made me nostalgic to think about. Remembering the times when he would come over to our place after work to mentor me. Letting me try my hand at writing his reports, or doing some of his basic data entry work. It could be a long monotonous slog at times, but I learned a lot from it!

I was hoping the experience would bring us even closer together. Two disciples of the same master business man. Maybe that was a little dramatic, but I liked the imagery of it, and I knew from experience that training under Mr. Thompson changed you. The Jamie from before starting this job would be a whole different woman from the Jamie that was experienced in it!

Feeling good, I decided to relax on the balcony. It was a beautiful day, and a little fresh air would be the perfect afternoon pick-me-up!

Stepping out into the fresh air, I soaked in the atmosphere. Sitting down I basked in the remaining light of the day, letting the stresses of the day wash away. It was so peaceful and quiet up here. The sounds of the city a distant, calming noise. The gentle breeze lazily brushing past me. A perfect, tranquil paradise.

“Robert!” A faint voice drifted into my ear. “I don’t think that’s very appropriate sir.”

“Why not?” The reply came. “You wouldn’t say that to a professional masseuse now would you?”

It was Jamie and Mr. Thompson. Our balcony was right next to theirs, blocked from sight by a privacy wall. Although from how faint their voices were, it didn’t sound like they were outside. They must have just had the door open, they probably weren’t even aware I could hear them.

“Well… No…” Jamie told him. “But given the current circumstances-”

“You worry far too much girl.” He said. “I can feel all that stress you carry in your glutes. Just let me rub you down until your body melts in my experienced hands!”

Was he giving her a massage? How thoughtful of him! Maybe this was him apologising for overreacting earlier? Showing his newest employee that things were still good between them.

“I just wonder if I shouldn’t cover up a little more…” I could hear Jamie’s nervousness in her soft voice. Come to think of it, this was probably her first ever massage? She must have felt odd lying there in nothing but a towel. I wished I could have reassured her, told her that it was perfectly normal, but I didn’t want to interject from out of nowhere. I had to trust that she could handle this herself.

“Pish posh.” Mr. Thompson replied. “This is how it should be done. Now just lie back and enjoy.”

“But-”

“There’s only one but here I want to see!” I heard a laugh mixed with a clapping sound? I didn’t really understand what he was saying, so I figured it must have been some reference to something I couldn’t see. Or maybe an inside joke? “Really though, you do need to relax. You're doing me a favour here by letting me practice, you know?”

“I… I guess it’s okay if it’ll help you practice. If you're sure this is alright…”

“Of course my dear, now let me just move these legs apart a little…” I could barely hear a soft moan from Jamie. Whatever technique Mr. Thompson was using must have been a good one. “These thighs are truly magnificent you know?”

“You’re… you’re a little close to-” Jamie stammered out.

“Don’t mind a little touch here and there. It’s a natural part of the process.” He explained to her. Jamie must have been really out of it if she was surprised he was touching her in a massage, that was kind of the whole point of it. “Now let's get back to those glutes! They must be sore after everything they’ve been through today…”

Everything they’ve been through? He must have meant the spanking from earlier, although that was hardly a rough ordeal. I couldn't see anything that was going on, but I expected Mr. Thompson had a grin on his face. The line nothing but a bit of his dry wit.

“That’s! Ohhhh… that's a little too close sir.” A moan escaped Jamie’s lips as Mr. Thompson began working on her. He’d never massaged me before, so I didn’t know how good he really was from first hand experience, but he always seem to satisfy my Mom! I would hear similar moans like Jamie was making now coming from her room some nights when Mr. Thompson put me to work, and she always came out of those sessions saying how her legs felt like jelly.

“I can’t believe how soft and shapely these are.” He told her. “How often do you work out?”

“I try- Mhmmm I try to exercise every day. With squats or Yoga stretches.” Jamie told him, making me think about her perfect round butt squeezed into her tight shorts. Jamie’s exercise routine was one of my favourite parts of the day. She would always get flustered or confused about why I loved watching her so much. I tried to explain how amazing she looks, but Jamie didn’t fully understand. No matter how hard I tried, I couldn’t get her to see just how sexy she really was.

“I’ll have to get you to show me how you do it.” Mr. Thompson chuckled. “If you wouldn’t mind demonstrating for me later?”

“I… I suppose I could show you my form.” Jaime moaned.

“It would be a big help.” He told her. “It’s been too long since my last personal trainer.”

I was starting to get hard again, the image of Jamie’s plump ass bending and shaking spinning in my mind. I knew just how soft her ass was, how it felt as I ran my hands over it. I could almost perfectly imagine myself in Mr. Thompson's shoes, rubbing oil all over Jamie's flawless tanned skin.

But my massage would be a lot more sensual, my hands teasing her most sensitive parts.

“That's…” Jamie half gasped half moaned. “That's enough of that spot. Isn't it sir?”

“I've nearly worked that knot our dear.” Mr. Thompson replied. “Be a doll and arch your back for me.”

Mr. Thompson seemed to be giving it to her pretty rough. Not like how I would do it. Jamie was a gentle girl who loved a soft touch.

My hands would caress her thighs. Gentle moving their way upwards, teasing her with what would be to come until I could feel the heat burning inside her.

“These things are as big as pillows girl!” I could hear Mr. Thompson laugh. “I could just bury my head in here and fall asleep.”

A harsh slapping noise caused Jamie to yelp. He was probably working her thighs now, just like I was in my head. Only Mr. Thompson wasn't touching her like I was in my fantasy.

Seeing her thick, juicy sex goddess body splayed out over our bed would get me hard in an instant. Her slick shiny skin practically begging for my touch. I wouldn't be able to resist pulling her far cheeks to the side and running my tongue down the length of her crack.

“C-could you go a little higher?” Jamie's soft voice asked. She let out a squeeze before saying. “I said higher!”

“Oops… sorry doll, I must have misheard you.” Mr. Thompson chuckled back. He didn't usually laugh off a mistake, no matter how small they were. Having Jamie around must have put him in high spirits.

I couldn't stop myself from rubbing the hard on I had that pressed into my pants. I had half a mind to go rush next door and drag Jamie back to our bed right now. The other, more sensible half, knew I had to wait. I doubted Mr. Thompson would keep any employee on if they took a break in the middle of a work day to have sex of all things…

At least I had my fantasies, and tonight I could have the real thing. For such a shy and sheltered girl, Jamie had a sex drive that could rival any man I knew. I knew she'd be feeling just as pent up as I was after getting interrupted this morning, and I couldn't not wait to spend all night with her. Making sweet love to my amazing girlfriend until the sun comes up!

“What soap do you use dear?” Mr. Thompson made small talk while he worked on Jamie's massage.

“I use a coconut scruUUBB!” Jamie yelped again. “That's a bit too close now…”

Mr. Thompson's hands must have really been rough to make her scream this much. Or maybe she just wasn't used to how a real massage feels. Not the soft, erotic kinds I liked to give her. But a real massage, with real pressure to work out her knotts.

“Apologies, my nose doesn't work like it used to.” He replied. “Just let me get one more good sniff, would you?”

“Does it have to be right between my-” Another gasp escaped Jamie's lips. Or maybe that was the sound of Mr. Thompson smelling her? I couldn't hear them perfectly.

“Just wonderful!” Mr. Thompson exclaimed after a moment. “Do be sure to lather it all the way in next time.”

“I'll keep it in mind.” Jamie said. Doing a bad job of keeping her annoyance out of her voice. I don't think she liked getting skincare tips from a wrinkled old man, but at least she was holding her tongue.

“Excellent! I do love when my girls know how to follow instructions.” Mr. Thompson said. “Makes training them that much easier.”

Taking my hand off my pants, I stood up. Stretching my arms while letting the cool air wake me up. I wouldn't get anything else done today if I just sat out here with my hand on my cock, and I didn't want to keep eavesdropping on them. I already felt kind of bad for doing it as long as I had.

“Alright, why don't you flip over now?” Mr. Thompson said as I opened the balcony door.

“Flip over! But… but I'm not-” The door shut with a thud. Keeping out all the outdoor noises.

I debated whether or not to tell Jamie that I heard her, eventually deciding not to. Telling her would just embarrass her, and I didn't want her to think I was listening in to everything she was saying. I know I would feel awkward if she was sitting over my shoulder while I worked.

Back at my desk now, I toiled away with pointless tasks to pass the time. Just waiting for the clock to hit five so I could take Jamie home and ravage her.

We had both been waiting all day for it, and nothing would get in our way now.

***

“What do you mean we have to leave now?!”

“I'm sorry baby.” Jamie sighed. “He sprung it on me last minute. It's not like I could say no anyways.”

Jamie had come home at five on the dot. Dashing my hopes of a romantic right together the moment I saw her face. She had the same nervous look she always had when she was about to tell me bad news.

“Ughhh I know, you're right. I just wish he would have picked a different night for it.” I told her.

“Yeah, but it is a welcome dinner. What other day would it be?” Jamie reasoned.

“I know. I know… I just really wanted to spend some time with you tonight.” I said. Stepping towards her.

She was staring into the bathroom mirror, fixing and applying her make-up. Without getting in her way I hugged her from behind. Feeling her plump ass cheeks pressing into my semi-hard cock, I couldn't resist giving it a playful squeeze.

“Ouch! Careful, it's pretty sensitive today”

“Sorry! My bad.” I apologised, stepping back from her. “I forgot you got spanked today.”

“It's been the worst!” Jamie groaned as she applied her mascara. “I told him I was happy for him to spank me whenever he wanted, just like you said to, and since then he hasn't been able to stop touching it!”

“Oh… so he spanked more than just at lunch?” I hadn't expected Mr. Thompson to do it this frequently. Did Jamie need the hands on guidance that much?

“Constantly.” She said. The word dripping with her annoyance. “Not like the first time though. He's just taken to giving me a slap whenever I walk by, or he'll ask me to pick something up off of the floor and give me a couple of slaps while I'm bending over.”

Huh… That didn't sound very productive… but he must have had some reasoning for it? I couldn't understand what she could possibly be learning if she was constantly getting spanked, but I knew that if I asked Mr. Thompson about it, he would have a good answer.

“Maybe you should let him know you're not comfortable with it happening that much?” I offered. Mr Thompson surely had a plan, but if Jamie wasn't happy with it then she needed to tell him. Even if he wouldn't like it.

“No, it's fine.” Jamie said. Sounding decidedly not fine. “I can't say anything about it anyways. I told him I was happy for him to do it, I can't say I don't like it now without looking like a huge dummy.”

“Alright, if you're sure it's fine then.” I trusted her to know her limits. Maybe this was proof I needed to trust Mr. Thompson more? He seemed to know how far he could push Jamie better than I did. That must have been a part of his plan.

“They don't hurt, not really.” Jamie puckered her lips together as she applied her lipstick. A deep seductive red that would draw any man's eyes “The worst part is when he makes me thank him though. I try to sound genuine, but when he's dropped the same pen three times I'm a row, just so he can spank me more, it's hard to sound positive.”

“Well I think you're doing an amazing job! Not just anybody could take that kind of pressure without cracking.” I said, thinking more on Mr. Thompson's plan.

He must have known she was getting pissed off. Jamie tended to wear her emotions on her sleeves, it just wasn't in her nature to hide things. So he had to be doing this intentionally. He was testing her, learning her strengths, her weaknesses, her limits.

The emotional part of me didn't like that he was making her uncomfortable, but business wasn't about emotions. It was about logic. Mr. Thompson knew what he was doing, and I knew he only had Jamie's interests in mind. Adversity breeds strength after all.

“I just hope he gives me a break from it tonight.” Jamie stared into the mirror, checking her work. “The last thing I want to feel is his hand reaching up my skirt in public.”

“People would think he's some old creep feeling you up!” I laughed. The idea was just ridiculous. As if Mr. Thompson would ever reach up a woman's skirt! Especially in public!

“Well… he did kind of-”

More knocking on the door interrupted Jaime. The frustration flairling in her eyes.

“Is that him?” I guessed.

“Yeah.” Jamie groaned. “He said he'd give me more time to get ready.”

“I'll let him in, you just focus on staying beautiful.” I gave her a quick peck on the cheek before heading to the front door.

“Coming.” I shouted over the sound of Mr. Thompson banging on the door. He could be so impatient, but at least he wasn't just barging in with his key.

“Michael my boy!” Mr. Thompson said as I opened the door. Sounding a lot cheerier than the last time he was here. “Ready for our night out on the town?”

“Yes sir.” I replied. Stepping out of his way.

“Fetch me a drink, would you?” Mr. Thompson sat himself down on the couch. Kicking his feet up onto the coffee table.

“Of course sir.” I told him. Moving to the kitchen to pour him a glass of whisky. The bottle was basically untouched. Whisky wasn't my drink of choice, and Jamie was such a lightweight she never drank at all. The only reason we had it really was for a moment just like this.

“So how did Jamie go today?” I asked as I handed him the glass. Neat, just how he liked it.

“Better than I could have dreamed, boy.” He licked his lips as he took a sip of his drink. “But she still has a long way to go.”

“I know she'll prove her worth to you!” I exclaimed.

“Oh I know that.” Mr. Thompson smirked. “I'll be squeezing every drop of worth out of my newest investment.”

Jamie had really made an impression on him today! She just had to stick with it now, and we'd be set for life! It wouldn't be easy, Mr. Thompson would only get harder on her, but I knew she had it in her to make it through! And when he had finally molded her into the person she was destined to be she'd see that all the suffering and sacrifices she made were worth it!

“Ready boys?” Jamie stepped out of our room dressed to kill. Wearing her sexiest, most expensive dress.

A black strapless cocktail gown, with a split down the side that exposed her soft thighs. She’d had the dress for a while now, but it still mostly fit her. Although you could tell she had to squeeze her chest into it, with her cleavage almost burning out of the top.

“Ready indeed.” Mr. Thompson stood up and offered her his hand. She took it and he pulled her into his arms, dropping her down low like a professional dancer.

Before Jamie could do anything he pulled her back up onto her feet. Letting her stumble forward, slapping her ass over her dress as she went.

“Robert! Please…” Jamie kept her distance from him. Crossing her arms around her body.

“Oh come now, we're just having a little fun. Isn't that right Michael?” Mr. Thompson asked me.

“It's alright Jamie.” I reassured her. “We're just having some fun.”

Jamie didn't seem quite convinced, but she took my word for it. She didn't see things like I did. See the underlying plan behind Mr. Thompson's behaviour.

I braced myself for what could be a rough night, but one that I hoped we could all look back on and laugh.

“Exactly.” Mr. Thompson finished his glass while staring at Jamie. Studying her body language to see how much more she could take no doubt.

“Enough wasting time then! The limo is waiting, and this night has only begun.”