Never Have an Affair with Your Boss

A self indulgent fantasy with the characters lacking any self control and enjoying the pleasures of the flesh.

Leaning on coincidence, I've found that strange coincidences do happen in life.

Again the decision or indecision of which genre to put this in. Readers will always disagree.

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When you're only twenty three and in your first 'proper job' you have to be quick thinking in making judgements about those around you.

Rosemary Morgan was one of those. I'd met her at my interview along with the senior partner, but that situation was very formal, and very structured. When I got the job and knew that I'd be in her team it didn't faze me, she was an attractive woman, if not a little curt.

To explain. I was fresh out of university and this job was in a medium sized accountancy firm in a large city in the UK. I still lived with my parents just a twenty minute train ride from where the job was. I considered that a pretty good situation, at least to begin with.

The others in the office, about a dozen in Rosemary Morgan's team, were a complete mixture of ages, of sexes, of backgrounds, pretty diverse all in all.

I realised quickly that they weren't a bad lot, however they were all slightly wary of the 'boss.'

I could see that completely, which is why it threw me when after a week I began to be aware of the way she spoke to me. It was never in the open office, it seemed it was just on the few occasions when I was in her personal office discussing some account or other.

There were little innuendos, holding eye contact with me, playing with her hair while talking to me.

Now I wasn't completely naive, but I hadn't a long history of relationships with women. I'd probably had a bit more than most young men of my age, however it consisted of essentially three women.

The first was Linda, the girl at college that took my virginity in the most embarrassing way. The way that all young guys dread. The fumbling promise of your first sex and then when it happens the dismal failure of lasting only a couple of minutes. We did get better at it, but it was never earth shattering.

Then there was Vanessa, the third year student who I met as a first year at uni. She made it clear from the start what she wanted. Me! And she taught me a lot. Of course it finished when she graduated and then went abroad to work, but we still keep in touch every now and again on social media.

Finally there was Mrs Phillips, a fifty two year old divorcee, who I did some gardening for between terms. Not so much gardening, more helping with the state of her libido. She was insatiable and never was any part time holiday wage earned so much.

So I wasn't totally unaware of the body language and little signals that women sometimes emitted. However this was my superior, my boss, the one who decided if I was competent, and like Mrs Phillips, a woman of mature years.

I decided that I wouldn't react in any specific way, just in case I was mistaken, and my mind was playing tricks. After all this was my first taste of a real career.

When three weeks had past Alison, who'd been with the company for just over a year, said to me, "When's your first appraisal?"

"I think it's after about a month," I replied, "why?"

"Oh no reason, my first one was a bit longer than that because she was on holiday."

"It must have been okay, you're still here!" I chuckled.

Alison smiled, "Yes it was okay, but she tells it like it is, warts and all. I was in there for an hour after work, I think she was pretty pleased with me. I've got my yearly one in a couple of weeks."

"You've made me nervous now," I said.

"You'll be okay," she replied, "I think she's taken a shine to you."

I must have pulled a face.

Alison went on, "I've seen the way she acts around you, remember I can see through the glass of her office from my desk."

"Stop it, you're teasing."

"Maybe," she said with a little giggle.

It made me think again, if someone else had noticed then I hadn't been completely wrong.

Coincidentally a couple of hours later I got the summons.

"Tom, we need to get your appraisal done this week, can you stop behind on Thursday evening, it shouldn't take too long?"

Rosemary was speaking towards me from the doorway of her office as I sat at my desk.

"Yes, certainly, that's fine," I replied.

"Good," was her reply before going back inside.

"See!" Alison whispered, "the moment of truth."

I was tempted to give a rude sign, but I didn't know Alison that well at that stage.

Sandeep, an older Asian guy, muttered, "You'll do okay mate, it's no big deal."

Despite all the reassurances I was distinctly nervous as Thursday approached. I made sure that all the files I was working on were up to date and as the office emptied out the moment arrived when Rosemary beckoned me in.

She could tell straightaway I was a little apprehensive.

"There's no need to worry Tom, come on in, take a seat."

Rather than sit behind her desk she'd brought her office chair to one side and pulled my chair into a position facing her. As she sat down I couldn't help glancing at the way she crossed her legs and the rounded curve of her thighs in her pencil skirt. I randomly wondered if she wore stockings and mentally told myself to 'get a grip.'

"Good night Geraldine," she shouted through the office door as the last person left for home.

Turning to me she began, "Now young Tom, I hope you don't mind me calling you 'young,' I'm very pleased with you so far."

I smiled and relaxed a little.

"You've shown good initiative and when you've needed help you've either asked one of the others or come to me, that's good."

"Thank you," I muttered, waiting for her to continue.

"What do you think of everything so far?"

I wasn't expecting to be asked a question so early into the appraisal, and I stuttered a bit.

"Yes... yes, it's been good, it's all new of course, but yes I'm enjoying it."

"Good, and how do you find your work colleagues, are they being supportive?"

"They're brilliant, everyone's made me very welcome."

'And what do you think of me?"

It was a moment when I wanted to disappear into a hole in the floor, I must have gone red looking downwards, and quickly said, "You're lovely," and realised straightaway I'd probably chosen the wrong word, I corrected myself, "I mean you're great, someone who I look up to."

It all sounded very odd and Rosemary burst out laughing.

"Well I've rarely been called 'lovely' in an appraisal, but I'll take it Tom," she replied, still giggling, uncrossing and crossing her legs again. This time she didn't tug at the hem of her skirt, but allowed it to ride up a couple of inches.

"All in all you've made a good start, and so you've no need to worry," she went on, and just for a moment twirled her fingers through her auburn hair.

"So anyway it's all good, no more interrogation," she smiled and stood up, tugging her skirt down over her hips, "just one other question Tom, do you have a girlfriend?"

It was another totally unexpected one.

"Er no, not at the moment," I must have looked a bit puzzled.

"Okay, sorry perhaps I shouldn't have asked that, I'd seen you chatting with Alison quite a bit."

Rosemary had a sort of mischievous smirk on her face.

I blushed and replied, "No we're just friends, she's not my type."

"Apologies, I won't ask what your type is."

It was the flirting again, or at least that's the way I read it.

She changed the subject, "What time's your train home?"

"They're fourteen minutes past the hour," I replied.

"You live in Roughton don't you?"

"Yes," I replied.

"Well I live in Little Broxby so I go past there, would you like a lift tonight, seeing as I've made you late?"

She gave me no chance to reply, "Come on, it's no problem, let me lock up and set the alarm, just wait outside by the lift."

I felt really awkward standing so close to Rosemary in the lift, my nostrils were taking in her perfume, and I felt quite relieved as we stepped out to take the short walk into the underground car park.

The click clacking of her stilettos echoed around the concrete interior and I drew a deep breath when I saw her Porsche.

"Excuse me while I change my shoes, I can't drive in these," she said as she opened the passenger door and took some flat shoes off the seat. I watched as she slipped out of her heels, holding onto the car and standing on one leg to put her driving shoes on. I couldn't help but see her skirt ride up and it confirmed my suspicion about the stockings.

I wasn't sure if she caught me looking, she just said, "In you get," and threw her heels over the back of the seat.

I did get in and waited for her to put her briefcase in the boot. Again I enjoyed the view of her legs as she got behind the wheel.

The journey home felt a bit awkward at first, and then became a series of questions about my family, my uni days, and generally this and that.

"You'll have to direct me this last bit," she added until we drew up outside my house.

"See you in the morning Tom, I hope we know a bit more about each other now."

We both smiled and I went indoors to the inevitable barrage of questions about who the woman in the Porsche was.

"It's my boss!" I replied, and was met with even more questions.

Everything was fine at work for the next few weeks. Rosemary still continued to be quite familiar with me when we were out of earshot of the rest of the office. It was one weekend when it all began to change.

Jed, my best friend from uni came to stay for the weekend. He'd got a job in London so we didn't have much opportunity to meet up. Mum and dad knew him well and the Friday evening was spent at home with all of us enjoying a take away Indian meal and lots of lager.

Jed and I decided that on Saturday evening we'd go into town and visit a couple of pubs that played live music, and maybe go to a club afterwards. Mum said that she wasn't expecting us back anytime early and would let us sleep in on Sunday morning.

Needless to say we drank quite a bit in both pubs before we moved onto a club that I'd been to a couple of times before. It was heaving and the dance floor was crazy. We hung about in a lounge area at the side of the venue and tried to hold a conversation with a great deal of difficulty. We made our first drink last as the prices were obscene. A couple of girls who looked about our age, but could well have been much younger, made a giggly play for us. They gave up when Jed playfully starting talking to them with a twitch in his face and a stammer in his voice.

We'd been there for an hour before we tried to decide whether to move on to another club or go home. I was casually leaning on a chrome barrier with my back to the dance floor when someone tapped me on the shoulder.

"Fancy seeing you here young man!"

I saw Jed's face light up and I turned around to see Rosemary standing there. It was Rosemary yes, but not as I knew her. My mouth dropped open as I stared at her face, with its eye shadow, eyeliner, bright red lipstick and her hair in plaits carefully positioned either side of her head. I couldn't avoid looking down at the dress she wore, skin tight and low cut, showing the swell of her breasts.

"Errrr... Rosemary, I wasn't expecting to see you here."

"Obviously not. I'm with Maddy here, we're celebrating, would you believe, it's her divorce, and I wasn't expecting to see you here either!"

Maddy stood there in an equally tight dress. She was probably slightly younger than Rosemary and had black hair down to her shoulders along with slightly more subtle make up and a smile that would make men go weak at the knees.

I wasn't sure what to say next except, "Can I get you two a drink?"

"Okay Tom, yes, we'll just have a beer, thanks, it's expensive here."

I left Jed with the two of them and went to get the beers. By the time I'd returned they'd found three stools against a narrow bar at the side of the lounge. To my amazement he was engrossed in deep face to face conversation with Maddy, and from what I could hear it wasn't about politics or religion.

"Thanks Tom, your friend seems to have made a bit of a hit with Maddy. I'm not sure he's in the same age bracket, but she seems quite taken with him."

"I'm not surprised," I said above the noise, "he could chat up anyone, I can't leave him alone for five minutes."

"So you've been out on the town, where have you been?"

"Just to a couple of pubs then we came here, we were actually thinking of heading home when you arrived."

"We were too, like I said Maddy's divorce came through and we decided to celebrate. She lives in town not far from here so it's convenient if we want a night out..."

I saw her expression change and she added, " Oh my word, I think we'd better leave now!"

I glanced behind me and Jed seemed to be playing tongue tennis with Maddy.

Rosemary shouted above the music, "Hey you two, we're going. Can you manage to get back to the flat?"

Maddy must have realised that the drink had got to her when she stood up. Smoothing her dress down she took half a step back from Jed.

"Are we inviting these two back? For coffee?" she asked Rosemary.

Perhaps, a bit surprised, Rosemary replied, "If you want to, I'm okay with Tom coming back," then with heavy sarcasm she added, "I'm not sure about you with his friend?"

Jed was clearly very keen, Maddy had a momentary second thought.

"Okay, but just for coffee."

"C'mon then,' Rosemary had now taken charge and she led us out onto the street where there were the usual drunks staggering around. It was probably a good thing we were escorting them back.

In front of us Maddy was wobbling a bit on her heels and eventually she took Jed's arm to avoid falling over. Rosemary saw the wisdom in that and grabbed mine.

"I hope to god no one from the office sees us, this isn't a good look!" She was giggling and apparently had had just as much to drink as Maddy.

"You're not dressed in your business stuff, so you're not immediately recognisable," I joked, looking down at her cleavage.

She appeared not to notice under the street lights, but added, "No, I think I've overdone it a bit tonight."

"I wouldn't say that." The remark felt again like a flirt.

Maddy's flat was literally five minutes away. By the time all four of us got into the lift Jed had got an arm around Maddy's waist. She didn't seem to object and allowed him to escort her like that along the corridor to her front door.

Rosemary and I followed separately behind, she was now walking without needing to hang onto anyone.

"Coffee everyone?" Maddy shouted as we entered a very comfortable flat.

"I'll do it," Rosemary interrupted, "you put the music on."

I followed her into the kitchen area of the open plan lounge, while Jed and Maddy were at the far side, poring over the small hi fi unit. I was expecting nineties stuff, but some modern jazz began to play. I got the mugs out of a cupboard while Rosemary percolated the coffee.

By the time she'd made it we could both see Jed and Maddy kissing yet again.

"Oh dear, I'm afraid this might not end well," Rosemary spoke quietly.

Even as she spoke the two of them disappeared into one of the bedrooms.

"Shall I take their coffee into them?" I said with a jokey smile.

Rosemary half frowned. "Let's just sit down and drink ours, I'm not sure what you think, but I'm inclined to leave them to it and get off home. Is Jed meant to be staying with you?"

I was just explaining how he was here for the weekend when the first sounds came from the bedroom.

"Oh no!" Rosemary groaned.

I saw her face blush as we both heard Maddy cry out, "Yes, oh yes, Jed!"

When the sounds of the bed creaking began to make a steady rhythm, Rosemary couldn't look at me.

"This is so embarrassing," she whispered.

I chuckled, "It's not how I imagined the night turning out, I must say."

"Oh god... oh god... OH GOD!... DON'T STOP... JED!" Maddy seemed close to orgasm.

"Let's get a taxi shall we, we can share it, I'm going your way." Rosemary was fidgeting with embarrassment.

"FUCKKKKKKK!" Maddy yelled as we shut the flat door and made our way to the lift, this time Rosemary clutching my arm.

"I'm sorry my friend has stolen your friend, I can only say it's probably because she's got her divorce and it's some kind of release or revenge."

"Possibly," I replied, "I guess Jed wasn't going to refuse. Now are you going to be warm enough, I reckon there'll be a taxi back around the corner?"

Without thinking I put my arm around her shoulder as she shivered slightly. She said nothing and as luck would have it there was a black cab approaching.

Once inside we told the cabbie 'Roughton' and Rosemary soon began to feel a bit warmer.

"Has it spoiled your evening Tom?"

"No," I chuckled, "has it yours?"

"Not really, I guess I'm sort of jealous of Maddy in a way."

Realising what she'd said she hastened to correct it.

"I mean... not like that... I mean..."

I pressed a finger to her lips and said, "Shush... I know what you mean and I feel a bit like that too."

The slight intimacy of touching her lips felt quite daring, the alcohol had got to me too. It must have triggered something in her as well.

She looked at me in the dim light of the cab and grabbed my wrist, lowering it down and resting my hand on her thigh.

"Kiss me Tom."

I stared in disbelief, hesitating. It felt like my heart had stopped, it was thumping out of my chest when our lips met. We kissed softly for a few seconds.

In what seemed like some fantasy she went on, "This is crazy Tom, I hope I won't regret it."

I could hardly hear her at first, then more loudly she called out, "Can you go onto to Little Broxby cabbie?"

The cabbie grunted in reply before Rosemary reached up to kiss me again, this time with a hunger and a passion. It felt quite bizarre. Apart from kissing a much older woman this was my boss.

Caution had been thrown to the wind by both of us, a hurried address was given to the cabbie before more kissing and finally the fare was being paid.

"You're gonna have to be damned quiet about this," Rosemary was saying as she fumbled with the key. The alarm was buzzing and again in a rush she missed the first pin entry.

"Fuck!... you get upstairs."

I went first not knowing where I was going at the top.

She caught up with me and said, "Here this way." She grabbed my hand and pulled me into her bedroom.

Throwing her arms around my neck she was pressing the whole of her body up against me and searching with her tongue and mouth.

"Unzip me Tom," adding, "get undressed, before I come to my senses!"

I struggled out of my clothes as quickly as possible. Rosemary peeled off her dress and in the dim light of the bedroom I could see her in just a bra and thong.

I was standing naked when she reached up to kiss me again. I was hard and it was unavoidable that my erect cock pressed up against her. She seemed to rock her body from side to side, rubbing herself against it.

I reached behind her to unclasp her bra letting it drop from her shoulders onto the floor, followed by a rather clumsy struggle to slide her thong down. Now I was able to press my chest up against her breasts as they hung free.

I pushed her away slightly lowering my head, but before I could kiss her nipples she said, "Let's get on the bed Tom."

Half shuffling and with little steps she fell backwards, pulling me on top of her. Her thighs spread wide and my lower body went between them. She pulled my head towards her to kiss me again.

"Tom, I haven't been with a man for over a year."

I smiled and mumbled, "I've never been with a woman quite like you, ever," and kissed her again.

I was about to take things quite slowly, wanting to please her with patience, but Rosemary didn't want that at all. She was already incredibly aroused.