Reluctant Proposition : Ch2

“Morning sunshine.” I ran my hand down Jaime's back. Gently trying to wake her up.

It was already seven am and she was still snoring away. She slept on her side, allowing me to get a perfect view of her juice thick ass. Her tan olive skin was perfectly rounded and completely bare. Jamie never wore anything when she slept, a fact I'd always been fond of. I'd taken to squeezing and groping her perfect ass so much that she barely even reacted to it anymore. She knew how much I loved doing it and just accepted it.

She was so kind. So continually selfless. Today needed to go well. If anyone deserved a job as easy and stable as this one would be, it was Jamie.

Finally waking up, Jamie rolled over and snuggled next to me. She rested her thighs on top of me, squeezing me into her soft plump chest. Smothering me in bliss.

“Morning baby.” She yawned. Stretching her body while still clinging onto me. “What time is it?”

I ran my hand down her side, reaching down to get a handful of her asscheeks. I'd never get over how amazing it felt just to touch them. To squeeze them and stretch her cheeks apart and listen to them clap as they crashed back into each other.

“It's about seven… we've got a little time…” I planted a kiss onto her neck. Teasing her body with my touch. “Maybe we could…”

“You want me to take care of you before work baby?” Jamie smiled. Her hands reaching down to run my cock over my shorts.

Fuck I was so hard. Even before she started teasing me my cock had been begging for some attention. Every time I saw Jamie's ass I couldn't help but get hard. My cock knew well just how good that ass was, and it wasted no time in getting ready to claim its prize.

But today wasn't about me. It was about her.

“I was thinking I'd take care of you today.” I pushed her down onto the bed. Holding her in place while I slowly began kissing my way down her body.

“Oh Michael…” Jamie was blushing. She nervously bit a finger as she watched me slowly go down on her. “You don't… you don't have to if you don't want to…”

For a woman as sexy as Jamie was, she could be so naive. Her body was literally crafted by the sex gods to be the perfect object of any man's desire, yet she just couldn't see herself that way. She had no concept of how good she looked, of how much I loved touching her. Tasting her. Even just seeing her, unclothed or clothed, was a blessing.

It wasn't that I wanted her to feel objectified, just desired. Even when I told her how bad I wanted her, how good she looked or how much I loved her perfect ass, she never quite believed me. She didn't think I was lying, but some insecurity inside her just couldn't accept it.

Hell, she was so bad with that stuff that even when a guy cat called her in the streets she took it positively. Some old greasy dude would whistle and tell her how badly he wanted to plough her back-door, and she'd just smile. Waving back while trying to explain that she lived in an apartment, and didn't really have a back-door the man could plough.

She always tried to see the best in people. Tried to help them however she could. It was why I loved her, and it was why I would do anything to make sure this job worked out for her.

“I want nothing more than to make my beautiful girlfriend cum before she goes to work.” I said. Trying to sound smooth.

Before she had any more chances to protest, I flicked my tongue over her clit. Feeling her things press into my head from the gentle touch. She'd always been so sensitive, so easily pleased. The flipside being that she was insatiable. I could make her cum three times in a row and she'd still be begging for more.

“Mhmmm, oh God.” Jamie moaned as my tongue caressed her. Slowly building up her pleasure to its breaking point. “I needed this so bad…”

I lapped up her dripping juices as desperately as I could. Savouring every drop of her taste that I got. The harder my tongue worked her wet needy pussy, the harder her thighs wrapped around my head, and the harder I got.

“OhhHh fuuck Michael!” Jamie's high pitched voice moaned out. “Please God don't stop!”

I rolled my tongue up her slender tight lips, moving up to suck on her clit directly. Rubbing my face over her big juicy pussy mound. Losing myself in her intoxicating essence.

As my tongue focused on working her clit and bringing her to orgasm, my hands wondered. I dug my fingers into her plump cheeks and spread them open. Circling a finger around her tight wrinkled asshole, but not daring to put my finger inside.

I was obsessed with anal, and desperately wanted to try it with her. I just hadn't built up the courage to ask her for it yet, even knowing she was likely to say yes. I'd been introducing her to everything sex related since we first got together, and jumping right to anal seemed like a bad idea.

It wasn't like I was in any hurry to experience it. I planned to spend the rest of my life with Jamie, so we'd have plenty of time to enjoy every inch of our bodies together. In the meantime, I liked to tease her sexy rosebud asshole whenever I was making her cum. My secret way of conditioning her to like it I suppose.

“Fuuck fuuck FUUCK.” Jamie's voice got louder and louder as she came closer to cuming. She'd always been a bit of a screamer. “I'M, I'M, FUUCK IM CU-”

THUD THUD THUD

A pounding on our door broke both of our concentration. Shocking me into throwing my head up.

“No no no!” Jamie whimpered. “I was so close!”

The pounding on the door continued. Whoever was there was determined to see us.

“Sorry, let me get rid of them.” I apologised. Leaving Jamie alone on the bed as I rushed to the door.

“Hello?” I asked as I opened the door. Expecting to see some door to door salesman, or maybe a neighbour asking us to keep it down.

Instead I was met with the wrinkled old face of Mr. Thompson. His stern blue eyes and cold expression warmed up as he saw me standing there.

“Is that how I taught you to greet your elders?” He joked dryly. Somebody who didn't know the man as well as I did probably would have thought he was actually scolding me, but I knew it was just his way of having fun.

“No sir. Sorry sir.” I said back. Straightening my posture. “Good morning to you too sir, what brought you here so early?”

“I wanted to give my newest employee her uniform in person!” He showed me the brown paper bag he held. “Where is she?”

“She's, uhh… she's getting ready right now! But I'd be happy to give her the uniform for you!”

“Hmmm” Mr. Thompson pondered for a moment, until he noticed something on my face. “Is… is that lip gloss you're wearing son?”

Lip gloss? I wasn't wearing anything like…

Oh god. My lips… Jamie's wetness must still be coating them. Giving my lips a wet shine to them.

“Uhh, yeah. Thought I'd try something new.” I lied. Too embarrassed to tell him the truth.

“Interesting choice.” He said. Dryly. “Back in my day, a man would have been beaten up if we found out he was wearing makeup. But I guess you young bucks are a different breed.”

“I was just trying it out!” I rubbed her slickness off of my lips. Desperately trying to recover Thompson's image of me. “I don't think it's for me…”

“Well just let Jamie know to put this on and come over right away.” He handed me the bag. Still looking at me strangely. “We have a busy schedule for today, and I won't broker any tardiness!”

“Of course sir! I'll send her over right away!”

I closed the door behind Mr. Thompson and rushed back to Jamie. Finding her still splayed out in our bed, her neatly trimmed pussy leaking all over the sheets.

“Who was it baby?” She asked. Eyeing up the bag I held.

“Your new boss.” I put the bag down and sat next to her. “He's got a uniform for you to wear, and he wants you over ASAP.”

“Ughh… don't say that! Can't we just quickly finish up first?” Jamie rubbed her hand on my chest. Staring at me with big puppy dog eyes.

“We should really get ready now.” Those were hard words to say when a perfect sex goddess was begging you to take her. But I’d already fucked up and put Mr. Thompson into a bad mood. Making him wait any longer would ruin this one chance we'd been given. “But I promise, right after we finish work I'll make you cum as many times as you want!”

“Ughhhh.” Jamie groaned. I knew I was letting her down, but we really needed this job to go well. “I can't believe I have to work for that old man.”

“Jamie! Don't be so rude. Mr. Thompson is the only reason we're not out in the streets right now!”

“I know I know.” Jamie sighed. “I didn't mean it. I'm just frustrated. He's always been good to us.”

Jamie sighed again and pulled the bag over. Perusing its contents.

“Wow, he even included underwear. “Jamie said. Pulling out the black lacy panties he'd given her. “Haven't had a uniform that included anything like these before.”

“He's not a man that takes half measures!” I chuckled. “He likes having everything accounted for. He probably just wants to make sure your entire outfit matches. Even the parts he doesn't get to see.”

“I just wish he'd chosen a more comfortable pair.” Jamie looked over the panties. They weren't the type she would normally wear. More like lingerie than office wear. I couldn't blame Robert for that though, he was an older guy. Not someone who'd know what kind of panties a woman would want to work in.

“He's trying to make a good impression.” I told her. “Trying to show you what an organised boss he'll be. The least you could do is wear it all and let him know to get a more comfortable pair next time!”

“You’re right.” Jamie nodded her head. “Well, I better go shower quickly.”

“Let me make breakfast for you!” I kissed her on her cheek. Springing up into action. “You just focus on looking good, I'll handle the rest!”

I stepped into the kitchen as Jamie began running her shower. Throwing together some bacon and eggs. I knew she wouldn't have the time to eat much, but I wanted everything about today to be perfect for her.

By the time she was walking out of our room, breakfast was served and some freshly squeezed juice was poured. A delicious delectable meal, but the only thing I was hungry for was walking into the room.

“What do you think?” Jamie asked. Striking a pose for me.

She looked stunning. Her plain white blouse clung tightly to her chest, the buttons straining to keep her fully covered. She wore black heels and stockings that failed to keep her thick thighs in check. Emphasising her lovely voluptuous curves. I caught a hint of her garter belts that drew my eyes up to her skirt. A smart pencil skirt that would have worked on any woman.

Any woman except Jamie.

Robert had obviously bought the clothes a few sizes too small, as most of her employers seemed to do, and Jamie's body only made the difference more noticeable. What was supposed to be a simple basic office outfit ended up looking more like a strippers costume. The tight pencil skirt clung to her body like a second skin. Displaying her lusciously thick hips and every curve of her ass.

“What do you think?” Jamie smiled. Twirling around so I could see every angle of her body. “It feels a little tight. Do you think I can wear it out?”

I was mesmerised staring at her. The hem of the skirt only just covered her asscheeks completely, but it was so tight she might as well have been naked. The plump fullness of her ass squeezing against that thin fabric. Pulling it down between her cheeks, showing off the crack of her ass to anyone who looked.

This was by far the sexiest uniform I'd seen her wear. Under normal circumstances there was no way I'd tell her it was okay to wear out.

“I.. I… I think it looks amazing!” I told her. “But it is a little small on you. I'm sure if you ask Mr. Thompson for a new one he'd be happy to get you one that fits a little better.”

“You really think so?” Jamie turned around. Putting her hands on her thighs she bent over, pointing her ass towards me. “You can't see anything. Can you?”

Jamie wiggled back and forth. Hypnotising me with the swaying of her ass. She wasn't fully bent over, but her skirt definitely was riding up. The underside of her round bubble butt flashing me, with just a hint of those tight lacy panties showing. The panties being almost entirely swallowed by her perfect thick ass.

“N-no… can't see anything.” I lied.

These weren't normal circumstances. This wasn't a customer facing job, or even a normal office job. The only person she'd be around all day was Mr. Thompson, and I knew he wasn't the type to take advantage of her outfit.

So even though the outfit was very much not safe for work, I knew it would be alright. Robert was a very rational man, and when he found out her uniform didn't fit I knew he'd get her a better one! Unlike every other boss she'd had who couldn't help her due to ‘budgetary reasons’.

“You're sure?” Jamie asked again. Shaking her ass up and down just hard enough to make her plump cheeks jiggle. “It's not riding up at all?”

“Not one bit.” I gulped. Sitting down at the breakfast table before Jamie noticed the tent in my pants.

Placated by my words but still a little unsure, Jamie came and sat down with me. Picking at the food on her plate.

“You should probably head over now if you're not hungry.” I told her. “You'll only be next door, so you can come have a bite if you get hungry later.”

“You're right. I should get going.” Jamie stood up and walked over. Bending over to kiss me before starting her first day. Jamie was a very passionate girl, and normally when she kissed me the only thing on my mind was her lips.

But today I couldn't help but think about her ass. How it would look right now as she was bending over. How much I wanted to bury my face between her cheeks and stay there all day. How much I wanted to fuck her from behind and listen to her moan over the sound of her asscheeks slapping against me.

“Have a good day sweetie!” Jamie beamed. “Love you!”

“Love you too.” I said. My eyes locked onto her bouncing juicy ass as she walked out the door. All her bending over and shaking had pulled her skirt up. Leaving the bottom of her cheeks exposed even when she stood straight. I should have said something, but I didn't want to throw her off. She'd be worrying about her outfit all day if I said something now, and she needed to focus on her work. When she gets distracted, she gets clumsy, and when she gets clumsy, she gets fired.

But, if I was being completely honest. The real reason I didn't say anything was a selfish one. My balls still ached from our earlier fun, and they wouldn't let me ruin the beautiful sight of her ass by telling her to fix her skirt.

I let a deep sigh out, slapping my face to wake up. Jamie was gone, work was about to start, I still had a raging hard on, with ten or so hours until Jamie and I could finish what we started…

Fuck. I needed a cold shower.

****

The first half of the day was a blur. Back to back meetings and endless reports that needed to be distributed. I didnt even realise it was lunchtime until I heard Jamie clicking the lock of our door open.

“Hey baby, how's working with Mr. Thompson going?”

“It's… umm…” Jamie stumbled over to me. She'd switched out her simple flats for a more extravagant pair of heels, and hadn't quite adjusted to them. “It's good…”

Our apartment was the smallest one on this level, squeezed in next to the bigger, fancier rooms. Single bedroom and bathroom, with a combined kitchen and living space. That left me without any real office space, but I was fine with that. A desk against the wall by our balcony windows might as well have been my own personal corner office.

“Good?” I asked. She didn't sound very convincing. “Just good?”

“No, it's… it's been really good.” Jamie kept stumbling over to the fridge, looking for leftovers to reheat. “Mr. Thompson is great, and he's being really patient with me.”

“But?”

“But he's a little… hands on…” Jamie stressed the words. Making them sound like a bad thing.

“What's wrong with being a little hands on?” I asked. Mr. Thompson could be a little overbearing sometimes, but I knew that was only because he was trying to get the best out of you.

“It just doesn't feel completely appropriate.” Jamie eked out each word, and seemed to regret saying it the moment she had. “I don't think he's intentionally doing it though! He's just…”

“I know exactly what you mean. I've been there too, you know.”

“You have?” She asked. Sounding confused despite knowing that Mr. Thompson mentored me.

“Oh yeah! Back when I first got into business school he was really hands on. Every time I wrote a paper I had to endure his ‘little touches’.” I remembered it all too well. Even the practice papers I wrote needed his little touches. Pages and pages of notes and rewording suggestions. He always said those little details were the most important thing to get right, that they needed his experienced touch the most. “I know they can be a little annoying or frustrating, but if you just do as he says you'll see the benefits! Everything the man does has a reason, trust me.”

“Everything? Are you sure?” Jamie microwaved her food and sat down at the table. I wanted to join her, but I was still midway through some work. Nothing I couldn't do while also talking to her, but it needed to get done.

“Why don't you tell me what's happened today so far?” I said. Glancing back and smiling at her to show her I was listening, before turning back to the screen and typing away.

“Well… when he opened the door, he pulled me into a hug.” Jamie began.

“Uh huh.” I hummed attentively. I hadn't expected Jamie to recap literally everything, only the relevant bits.

“He held me like that for a while… a couple minutes maybe… did he hug you like that?”

“On occasion he's hugged me, but you're a girl so it's different.” Jamie's sheltered upbringing was showing its head again. Guys greeted girls they knew with a hug, that was just how things went. To someone that didn't understand social norms, like Jamie didn't, a quick greeting hug might have seemed like it lasted longer than it did. “He was just being friendly. Maybe it's not what a typical boss would do, but you're closer than that.”

“Am I close to him?” Jamie asked. “I feel like I'm learning a lot of stuff I didn't know about him…”

“Jamie.” I stopped working and turned to look at her. Giving her my best ‘big dumb smile’. “He's like family to me. And you're a part of that family! If I'm just like a son to him, then you're basically his daughter.”

“I'm not so sure…” Jamie took a bite of her food. Thinking while she chewed. “He showed me how to file invoices away, and answered every question I had without any judgement… That was nice, but there were other times. Times where he felt a little… distracted.”

“Uh huh. Like what?” I asked as an email notification popped up.

“Well, he gave me this big stack of papers and told me to file them away. One by one. I asked if it wouldn't be faster to do them all together, and he just said that this wasn't about that …”

“That sounds like him. Always with some hidden lesson.” Oh man, this was really fucked up. This order had been keyed in completely incorrectly. The customer was going to be so pissed if I didn't sort this out right now.

“That's what I assumed.” Jamie continued her story while I frantically typed up emails. “So there I was, taking a page from his desk. Bending over to file it away in the bottom of his cabinet, just like he taught me. All while Mr. Thompson just sat there. Not at his desk, but on those leather sofas he has. Watching me from behind as I worked. He would scold me if I did it incorrectly, bending with my knees instead of leaning down with my hips. That's when he would come over and show me how to do it properly again. He put his hand on my back and my thigh, pushing down while rubbing my legs. He said it was for support, but I don't know…”

“That's nice. Sounds like he's teaching you a lot.” I wasn't really paying attention, but everything seemed fine. I did want to listen more attentively, but work needed to come first right now, and Jamie was adding in a lot of unnecessary details into this story. Clearly she had a lot to learn about summarising pertinent details efficiently. No wonder Mr. Thompson was teaching her so actively.

“I… I guess he is, yeah…” Jamie nodded. “I think you're right, he's probably just trying to do what's best for me.”

“Be happy he's showing you this much attention.” I sent the last email I needed to for now and spun around to face her. “A lot of people would kill to get the kind of hands on training you're getting. Especially with someone so experienced.”

“I guess you're right.” Jamie ran a finger through her hair, idley twirling it. “I do know how lucky we are to have this opportunity, and I am having more fun than any of my other jobs.”

“You'll get used to working with him. Trust me. I know how smart and capable you are. You can take anything he throws at you.”

“You think I'm smart?” Jamie's nerves had been thoroughly calmed. Now her eyes had a different, more enticing energy.

“Smart and beautiful. The full package.” I stared back into her eyes. A sly smile forming on my face. “Hey… how long do you have for lunch?”

Jamie smiled right back at me. Putting a finger in her mouth over her full glossy lips.

But the moment she opened her mouth to reply, she was interrupted by the door clicking open.

“Mr. Thompson?” She said instead.

“Sorry to interrupt you two lovebirds.” Mr. Thompson stood by the doorway.

“It's no interruption at all sir!” I sat up straighter. Fixing my hair. “I didn't realise you had a key to our room though.”

“Hmm? Of course I do son, I've got the master key to this entire apartment block.” He stepped inside. Showing off his master key. “Or did you forget who owns this place?”

God that was a stupid thing to say. He was right, obviously our landlord would have a key to the room.

“I suppose you want me knocking before stepping into my own apartment to speak to my own employee.”

“Oh no sir! You're welcome here any time! Our door is always open to you!” I said, a little too quickly.

“Good stuff my boy.” Mr. Thompson nodded his approval at me, and then turned to Jamie. “I only wanted to ask if you'd like a coffee before finishing up your lunch break.”

“I'll get them for both of you!” I burst out before Jamie could reply. “It's the least I could do, and you and Jamie should be getting to know each other better today! Stay here and talk, I'll be right back!”

“That's why you're my star pupil Michael.” Mr. Thompson smiled at me as he made his way to the table. Sitting next to Jamie and putting his arm around her. “Although Miss Jamie here is giving you a run for your money!”

“That's kind of you to say Mr. Thompson.” Jamie kept switching between looking at me and at Mr. Thompson. As if she was checking for my approval of his behaviour.

“Please, call me Robert. Or Rob.” Mr. Thompson kept his arm around her waist. It was nice to see how quickly he'd taken to her. It took months of hard work to get to that level of rapport with him when I first started taking his mentorship seriously. Maybe he'd gotten softer with age, he certainly had around the belly! Or maybe he just saw something special in Jamie…

“I won't be a moment!” I told the two of them as I left the apartment. Taking the elevator down to the coffee shop in the lobby.

Unsurprisingly there was a big line for the lunch rush. I wasn't in any hurry though, and frankly enjoyed the excuse to stretch my legs.

“Hi Mike, you're out early today.” The blonde woman behind the counter smiled as I approached. “So what will it be today?”

“My usual and an extra today.” I smiled back. Ordering for Jamie and Mr. Thompson as well as myself. “I got Jamie a job working for Mr. Thompson, so I guess I'll be ordering for three from now on.”

Back when I was first learning from Mr. Thompson, he always had me bring him a coffee in the mid afternoon. He said that nothing made a good first impression like bringing someone coffee did. That was years ago now but I still tried to keep up with it, bringing him a coffee most working days. A little pick-me-up that strengthened our relationship, just like he'd taught me.

“I thought she just started a new job last week?” Amy worked as she talked. Gracefully moving with a practiced efficiency.

Amy was the shining star of this grey, sterile lobby. Flowing blonde hair and stunning green eyes, with a body that captured the eye. Her barista uniform consisted of a tight branded crop top with even tighter booty shorts. The thick curves of her legs tightly compressed against the stretching fabric. I tried my best not to stare as she worked, but the machine was opposite from the counter. Her quick precise movements while working led to her constantly shaking her ass. The full, plump butt not as big as Jamie's, but still hypnotically jiggled with every step she took.

“This job pays better. And she's closer to home.” I explained to Amy. Leaving out the part about Jamie being fired. “And now, two of my favourite people are working next to me! What's not to like about that?”

“She's so lucky to have you.” Amy sighed. “If I had a boyfriend that got me out of this job I'd… I'd…”

Amy put the tray of drinks on the counter. Blushing red and avoiding eye contact with me.

“Well… it wouldn't be appropriate to say what I'd do to him.”

For as bright and eye catching as her physical looks were, her personality was the opposite. She was shy and quiet, never saying more than a polite hello to her customers. She took a shine to me pretty quickly though, maybe because I was her only customer that wasn't making ten times what she was.

She was a bit of a gloomy, nerdy girl. Working this job to pay for an engineering degree. The more we talked, the more shared interests it turned out we had. Slowly, over the course of our daily chats, she'd become one of the closest friends I had.

“You're a beautiful and smart girl Amy, you just need to put yourself out there!” I tried to sound as encouraging as I could. Poor Amy hadn't had a boyfriend the entire time I'd known her. She was a perfect catch, so it must have been her shy personality that was holding her back from finding a good man.

“I don't have any issues putting out.” Jamie stared at me with her sparkling green eyes. Putting her hand on my hand as I took the tray of drinks.

“Oh, okay.” Amy had a habit of phrasing things strangely. Just one of those quirks that made her who she was.. “Well there must be a cute guy who comes here? Just ask him if he wants to get dinner when you finish work! There's nothing more to it than that!”

“Doyouwanttogetdinner?!” The sentence came out as all one word. Amy jolted up straight, unintentionally bouncing her perky full breasts.

“Just like that! But a little more casual. You sound a little desperate if you say it like that…”

I paid for the coffee and waved goodbye, giving her a generous tip. Normally we could chat for a little longer, but Jamie and Mr. Thompson were waiting for me!

“Knock knock.” I jokingly said as I pushed the apartment door open.

The room was empty, with no sign of Jamie or Mr. Thompson anywhere. I was about to turn back and check Mr. Thompson's apartment, when I heard muffled sounds coming from our room.

“...accurate, then you really should take these off…” I heard the low rumble of Mr. Thompson's voice.

“Hey guys, I got the coffee.” I shouted out to let them know I was back. Putting the tray down on the kitchen table and walking into our room. “You two getting along?”

Jamie was standing in the middle of the room. Facing away from me but looking back over her shoulder. I couldn't see much of Mr. Thompson, but I could see enough to know where he was. Standing right in front of Jamie, arms around her hips and pulling her into a tight hug.

“Michael?!” Jamie gasped. “This isn't-”

“It's alright Jamie, I know what he's doing.” Sometimes it felt like Jamie thought she was living some cheap, sweet RomCom. That I would walk in on her doing something and get the wrong idea, and storm out without letting her explain.

I guess it would be sweet if she thought that way. It would mean that she thought I was the perfect man for her. The one destiny brought her to.

“You do?” Jamie said.

“I told you my skills were legendary.” Mr. Thompson chuckled. “Doesn't matter the woman, if I get my hands on her I'll learn her sizes faster than any measuring tape will tell you!”

“I used to catch him trying out this trick on my mom when I got home from school.” I told Jamie. “She always made the funniest faces when you guessed correctly.”

“There's no guess work in it at all my boy.” Mr. Thompson lowered his hands down to Jamie's ass. He was on his knees now, his face pressing into Jamie's crotch as his arms stretched around her. “This is all skill and smarts.”

“He did this with your mother?” Jamie asked. Sounding a little confused and adding, under her breath. “He wasn't lying…”

“He's a stuffy old man now, but he used to be quite charming.” I laughed at my joke. Looking to see Mr. Thompson's reaction.

He wasn't paying attention to us. Instead focusing on Jamie's body. His hands reaching around and shaking her ass while he muttered to himself. I guess that was a part of how it worked, he'd never actually let me see his process all the way through.

“So… you're okay with him taking my measurements this way?” Jamie asked.

“Of course baby.” I leaned in to give her a quick peck on the lips. Bending over to avoid interrupting Mr. Thompson's exploration of her body. “It's important to have your sizes checked regularly. Right Mr. Thompson?”

“Yes indeed.” Mr. Thompson cupped his hands around the bottom of Jamie's ass cheeks. Bouncing them continuously.

James must have been feeling extra nervous today. She kept asking me if I was okay with things that I obviously would be. Maybe it was because of how sheltered she was? Seeing things as ‘wrong’ when they were perfectly normal. Or maybe it was just first day jitters. Mr. Thompson wasn't an easy man to work with, and I really appreciated how hard she was trying.

I made a mental note to make sure I properly showed her that appreciation tonight. A tonight that I was getting more and more desperate to get to. Mr. Thompson might not have been shaking her ass for any sexual reason, but I couldn't help but get turned on watching her jiggle in that super tight skirt.

“I'll let you two get back to it then.” No sense standing around watching Mr. Thompson when there was work to be done.

“Do close the door on your way out.” Mr. Thompson commanded. His wrinkled hands now sliding between her ass and thighs. Unintentionally pulling the hem of her skirt up higher.

Jamie's face was bright red. Silently pleading with me not to go. She wasn't used to having a man that wasn't me be this close to her, the discomfort was clear in her eyes. But she would never get over that shyness if she never confronted it!

Jamie had been through a few different bosses over the years. Most of them had good intentions, but none of them had been the right fit so far. But now she was with Mr. Thompson, and there was nobody I trusted her with more!

“You got it boss!” I slowly pulled the door shut. Mouthing the words ‘You'll be fine’ to Jamie as the door closed.

She smiled nervously back at me. Clearly still terribly embarrassed, but enduring it for me. For us. My heart tugged as I left her, but I knew it was for the best. Not for me. But for her.

A few more days working for Mr. Thompson, and something as silly as this will never embarrass her again!