Never Have an Affair with Your Boss Pt. 02

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Sex with both your boss and her daughter is not a good idea.
10k words
4.72
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Part 2 of the 2 part series

Updated 08/11/2023
Created 08/01/2023
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Cleevedreams
Cleevedreams
2,237 Followers

This is the second part of a self indulgent story of pure fantasy.

If you haven't read Part One ('Never Have An Affair With Your Boss') then here's a synopsis.

Tom's first job after university is in an accountancy firm where Rosemary, his immediate boss, hits on him and they begin a clandestine affair. One weekend, when Rosemary is visiting a friend, Tom goes to a party with his parents and is introduced to Vicky the work colleague of Nancy, a girl he grew up with. There is chemistry straightaway between him and Vicky and they have sex. However Tom finds out that Vicky is actually Rosemary's daughter and he knows it's something that probably can't be kept from his boss.

*********************

I was physically shaking and I could tell that Rosemary was genuinely concerned.

"Whatever it is I need to know Tom, I can tell it's something serious."

I stumbled over my words and Rosemary came to hold me while I tried to explain.

"Rosemary, you're gonna go ballistic, you'll hate me, I really didn't know."

She had her arms on mine, her hands were resting on my shoulders and her face was inches from mine, looking deep into my eyes.

"Please... tell, it can't be so terrible."

I swallowed hard and took a deep breath. "I slept with Vicky... I slept with your daughter."

Rosemary's expression froze for a split second in disbelief. She suddenly held me at arm's length, taking in what I'd said.

Her first words were," How?.. Where?.. What the hell do you mean?"

Then the realisation hit her.

"Fuck Tom, are you sure?"

It was as if she thought it was some sort of mistaken identity. She stepped away, turning her back on me and began combing her fingers through her hair.

"How the heck did that happen, she's up in Manchester?"

I began stuttering again.

"She was visiting a friend of mine, I didn't know who she was, until it was too late."

"Huh!" Rosemary snorted, "you should have kept your cock in your trousers," knowing full well how her hypocrisy sounded.

"Does she know you work with me?" she added.

"Yes, that's how I found out, but she doesn't know about us!"

"I bloody well hope not," Rosemary snapped back, "and she'd better not find out either. Are you seeing her again?"

She knew instantly that I was.

"Yes, next weekend," I mumbled.

Rosemary turned back to face me, her green eyes piercing mine.

"This is the end of us you know Tom, if you want to fuck my daughter then it becomes impossible. FUCK!..." she yelled out loud, "OH FUCK TOM!"

When she burst into tears I was at a loss as to what to do. Sobbing, she stepped towards me, clutching onto me, muttering into my neck.

"Tom... oh Tom, we were so good together, you made me feel so... Jesus Christ Tom!"

"I'm so sorry Rosemary, really I am."

We clung together, knowing this was indeed the end. Gradually she calmed and held her face up in front of me, makeup smeared across her cheeks. Bizarrely we kissed, gently, softly, and then we stepped apart.

"I'll call you a taxi," she said picking up her phone, "I can't drive like this," adding, "I'm going to talk to Vicky, just to make sure she knows our relationship is purely professional. I expect she told you we don't really get on."

"She did... sort of," I replied quietly.

"I won't ask you what else she told you, just don't believe everything you've heard."

Rosemary ordered the taxi and said it would be fifteen minutes, before she switched back into her business persona.

"Can we get one thing clear Tom, I'm not going to show any clue about this at work, and I don't expect you to either."

I nodded in agreement.

"If Vicky chooses to tell me anything about you two that's down to her. I don't want you to tell me anything."

It was clear that Rosemary was shutting down any emotion she had for me. It actually saddened me, but the time and place to express it wasn't then.

"The taxi's here Tom."

I heard the toot of the horn and guiltily went towards the door.

"Wait Tom," Rosemary said, looking sad, and I think she tried to smile, "I wanted you so much."

I could hardly speak either, and whispered, "Thank you Rosemary, I wanted you too."

That evening there were various texts from Vicky, saying how much she was looking forward to seeing me at the weekend. I tried to reply enthusiastically, but found it difficult. I went to bed early and I think mum realised there was something up.

Next morning I arrived at the office at my normal time and Alison was there already. Alison shared the next desk to me and we exchanged banter constantly, mostly about Rosemary.

"She looks as though she's been up all night, I reckon she's been shagging," was Alison's opening gambit.

"Is she in already?" I asked.

"She was here when I arrived, but she's been in her office all the time."

"I'll stay out of her way then," I muttered, logging onto my computer and checking a file.

"I bet she calls you in soon, she'll want you to feed her ego."

"Stop it Alison, you can be an utter bitch sometimes." I was tired of her sarcasm.

Thankfully the day passed without any event. I wasn't summoned in and I needed no advice on anything, in fact the rest of the week went by without any upset, at least in the office.

However, I spoke each evening to Vicky and I wasn't surprised to hear that Rosemary had contacted her. Of course in their first conversation Vicky had revealed that she was 'seeing' me. I guess Rosemary must have feigned surprise and made all the correct noises, even though she and Vicky had quite a strained relationship.

I mention the first conversation because Vicky was very much surprised when she phoned a second time within a week. It was then that Vicky told her mum I was spending the weekend in Manchester.

On the Friday Rosemary arrived in the office just after me.

"A weekend away?"

She commented for the whole office to hear, because my small suitcase was beside my desk. She knew already where I was going, but wanted Alison to register it and turn her attention on me.

"Manchester," I replied, "visiting a friend." My tone was as deadpan as I could make it.

"Enjoy then Tom," she said as she made her way into her office.

"Male or female... friend?" began Alison's interrogation, as soon as Rosemary was out of earshot.

"Female," I answered, licking my lips in a suggestive a manner as I could.

"Oh god, some slapper on Tinder I bet."

I couldn't very well say it's Rosemary's daughter, so I ignored the jibe, and simply said, "Jealous."

Work ended and after the walk to the station the train journey took two hours, arriving in Manchester around seven thirty. Vicky met me and it felt great to hug her and feel her kiss.

Her flat was a fifteen minute tram ride away and it was on the ninth floor of a newly built tower block, one of three looking out towards the city.

She couldn't wait to get inside and my suitcase was abandoned as she dragged me into the bedroom.

"Oh god, I've waited all week for this, get undressed, I want to touch you all over."

She only had to pull her dress up and over her head with just her bra and panties to follow. She spread herself on the bed and watched me undress. One leg was bent at an angle revealing her freshly shaved pussy with its beautifully shaped lips awaiting my attention.

"Fuck Vicky, you look so good, I've had to resist masturbating this week and all I could see every night was you like this."

She giggled at my reference to something so personal and her smile got broader once I was naked with my cock rapidly growing.

"Come here, I want you," she sighed and I climbed on the bed beside her.

We kissed, and feeling her body up against mine only served to increase my desire. This wasn't a slow sensual session of making love, this was pure lust on both our parts.

We kissed, our tongues probing, fighting and in between Vicky was pleading, "Fuck me, I need you inside me."

Both of us seemed to wrestle the other in an effort to satisfy our lust. We rolled from one side of the bed to the other, and back again. When Vicky came her pussy seemed to pulsate and it took me over the edge. In a long, sustained groan, I flooded her with spunk.

"Oh fuck, I thought about this every night too," she whispered, kissing my neck as we lay side by side. We cuddled for a while, kissing, caressing and coming down from our high.

"We'll go out for something to eat shall we," she asked.

"Yes, of course," I replied, "you've got to show me Manchester."

Vicky showered first while I unpacked what little I'd brought in the way of clothes. After my shower we got back on the tram and found a favourite Italian cafe that she loved. The owner obviously knew her and I think we got special treatment.

We got back to the flat around midnight and this time we made love properly, taking our time and relishing the fact that the weekend was ours.

In the morning I awoke to Vicky sitting beside me with two mugs of freshly made coffee.

"Mum seems very pleased with you at work."

"She said that?" I woke up pretty quickly.

"Yes, and then she asked if I'd slept with you, I had to say I had."

"I won't ask what she said about that," I felt it was ironic.

"She actually asked if you pleased me!" Vicky laughed. "I told her 'very much."

"Oh god, do you have to discuss stuff like that, I thought you and your mum weren't that close?"

"That's the odd thing, not only did she phone me twice this week, but she seemed a lot friendlier."

I pondered for a moment, sipping my coffee and asked, "Well, do I please you?"

Vicky playfully grabbed my cock.

"Careful, I'll spill my coffee!" I yelled.

I put the mug down and reached forward, grabbing her around the waist to tickle her.

"Stop it," she screeched, "noooo, stop it!"

I wrestled her and in sitting up I pulled her over my lap and gave her a sound slap across one of her buttocks.

"Ouch!"... fuck Tom... that hurt!"

"That's what you get for being naughty."

I haven't been naughty, let me go you sod."

"I think you have, discussing what I'm like in bed with your mother is extremely naughty."

I landed another thwack across the other buttock.

"FUCK... you sod... stop it!"

I chuckled and smoothed my hand over the slightly reddened area of her rear.

"I'm sorry, I was tempted by that perfect ass and you're such a tease!"

As I said it my fingers playfully smoothed their way along the crease of her buttocks and probed down between her thighs.

"And you're such a devil... and shit... my ass is stinging," she responded.

Vicky parted her thighs just a little and I found her pussy sumptuously wet.

"That couple of spanks seems to have had an effect?"

"Mmmmmm... I've sometimes wondered if I deserve a good spanking like that."

"You mean it's a fantasy of yours?" I was interested now.

"Sort of."

The discussion was making me hard and my cock had risen up underneath her, where her breasts were flattened against my thighs.

I let her slide off onto the floor onto her knees whereupon she manoeuvred herself between my legs. I watched as she looked up, gathering her breasts in both hands and enveloping my cock between them. With a mischievous smile she raised and lowered herself up and down on her knees, using her breasts to massage me.

"Mmmmm... you're so... fuck it, I don't know what you are!" I hissed through my teeth.

I watched in disbelief when she screwed up her lips and dribbled a long strand of saliva down onto the head of my cock which was peeping up from between her breasts. The slippery ooze lubricated it wonderfully and I groaned as if it were being massaged by her pussy.

"My god Vicky! Fuck... that feels so good."

"Then let me finish it... don't stop me."

I was in total heaven as she raised and lowered herself up and down, holding her breasts together with my cock held captive. Twice more she parted her lips and let yet more saliva add to the delicious sensitivity. This was a new experience and I had given up on any self control.

She understood clearly how close I was and could dictate how good the stimulation was by squeezing harder, or by moving in a different way.

"You're gonna make me cum," I warned her.

She gave a little chuckle and the stray remnants of saliva on her chin added more to the eroticism.

"Oh fuck!" I sort of whispered it before I groaned, and a jet of spunk shot upwards from my cock and hit Vicky under the chin before it began running down her neck. The second and third spurt followed with the remainder pumping it's way out between her breasts adding to the whole slippery mess.

A giggle of triumph came from her as she released my cock and took it between her fingers to squeeze the last of the spunk from me. Her breasts were glistening with a mixture of saliva and semen as it all ran down towards her waist. With her other hand she gathered some of it up and seductively put it up to her mouth where she looked me straight in the eyes and licked it up.

"Jesus, you're showing me another side of you, that was awesome. You'll definitely need a shower now!"

Laughing aloud she leapt up and disappeared into the bathroom and I grabbed some tissues to clean myself up.

Taking our time afterwards we were both getting dressed when Vicky got a phone call that I think she was half expecting. I could only just hear one side of the conversation.

"I thought you might phone, you really are nosey!"

"No we've not got anything planned."

"If we do, please don't embarrass me, I'll hate you for evermore if you do!"

"And tell Rachel to be on her best behaviour too!"

"Okay... see you there at one, and remember what I said."

It was the name Rachel that gave me the clue. Rachel was Vicky's dad's new partner. From listening in I understood that we'd probably been invited out to lunch, and so it transpired.

"Do you mind Tom, you heard what I said, I warned him. The trouble is he 'has' to look after his little daughter and I made the mistake of telling him you were coming up this weekend."

"So he wants to make sure I'm not leading you astray. My god, if he'd seen you just now!"

Vicky chuckled, "He's bringing Rachel. Take no notice of her, she's a real flirt."

At the back of my mind was the fact that I'd not only fucked his daughter but I'd fucked his ex wife too. It seemed that at every turn in my life there was the twist of fate regarding them both.

Vicky was clinging to my arm when we entered the cafe/bar in the middle of Manchester. I knew straightaway that her dad was the guy with the blonde, sitting near the window. Rachel was like a younger clone of Rosemary except for her hair colour. Vicky's dad, Gary, was all I expected him to be. Tall, imposing, confident and going slightly grey.

"So this is Tom," he said as Vicky threw her arms around his neck and hugged him for quite a few seconds.

I tried to look confident and held out my hand.

"Hello," I looked at him and then at Rachel.

She stepped forward and kissed me on the cheek, clutching my arm briefly before saying to Vicky, "Good choice, I already fancy him!"

Immediately Gary scolded her.

"I told you Rachel, behave!" then turning to me he added, "sorry Tom, she's a bit of a pain sometimes."

With Vicky looking daggers at her step mum we all settled down to choose from the menu. I'd prepared myself for small talk and being cross questioned. It wasn't delayed in coming.

"I can't imagine how you're feeling Tom?" Rachel began, as soon as the waitress had taken our orders.

I waited to hear what was coming next.

"You having lunch with your boss's ex and his new woman. My god she hates my guts after the divorce."

"Rachel please! Don't get into that," Gary sounded angry whispering, "for fuck's sake!"

Vicky giggled, slightly embarrassed, but attempted to smooth things over.

"Tom gets on with her quite well, in fact since she found out I was seeing him she's phoned me twice which is unheard of."

I sat quietly while all this family catch up was going on.

"She spoke to me as well," Gary added, "although I must explain Tom, we are still relatively friendly."

"Only because you've still got to settle the holiday home thing," Rachel butted in.

My attempt at peace keeping seemed to work.

"I guess I've been the centre of discussion this week, I hope you think I'm suitable for your daughter?"

Everyone laughed just as the drinks arrived, and the talk was more about Manchester and the places to go.

Gary had originally moved to Manchester with Vicky because of a business move. He was in PR but had made some money through property dealings, investing in some city centre commercial property. He'd also gone into partnership with Rachel's brother which was how they'd met.

"My brother has a lot to answer for Tom," remarked Rachel, "you might not have had your job if Rosemary hadn't have got promotion after the divorce."

My mind turned over again and Vicky grabbed me and squeezed my thigh.

Rachel saw it and commented, "Awwww look Gary... young love!" She flashed her eyes at me and I knew exactly why Vicky's dad had got involved with her.

By the end of the meal I was a whole lot more relaxed. Gary was very easy to get along with and insisted on paying for everything. He also asked me to swap phone numbers because to quote, 'It never hurts to network.'

There were the usual hugs as we left, handshakes with Gary and a bit of a clinch with Rachel. When we were walking to the tram Vicky remarked again how she would always flirt with anyone in trousers. I suggested how physically similar she was to her mum and Vicky agreed.

We spent the evening in front of the tv watching a Netflix movie and drinking wine before going to bed and making gentle love. We both slept like logs and woke up to pouring rain outside, typical Manchester weather.

It was about ten thirty in the morning when Vicky got a phone call from her mum.

"I told you not to call this weekend." I heard her say.

"Yes, of course he's here!"

Yes, we're doing fine and we had a meal with dad yesterday."

"Yes she was there."

I could fill in all the gaps and Rosemary knew very well what she was doing. I also knew that she was getting screwed up about the whole situation. The phone conversation ended abruptly and Vicky put the mobile down shouting, "Go fuck yourself!"

I waited for the explanation.

"That was mum."

"I realised that," I replied and waited for more.

"I think she's jealous! Me with you for the weekend, dad with Rachel, and her back home twiddling her thumbs. Well she can fuck herself!"

"You did mention that," I added inappropriately.

"And you can fuck yourself too! Bastard!"

I hadn't known how touchy Vicky could be about her mum, so I apologised.

"I'm sorry," I put on a suitable face, "me being insensitive, now come here and give us a hug."

I gathered her up into a cuddle and held her tight. Buried in my neck her voice was muffled.

"I don't want you to go home," she sounded like a sad little child.

"I've got to, you know that, I'll come and see you again soon, or you can come and stay at mine."

"It's not the same." There was a pause. "I'm sorry Tom, I've fallen for you big time."

Vicky began to cry and my heart was throbbing a bit too.

"Oh my baby," I whispered, "please don't cry, you're such a sweetie. I've loved every minute of this weekend, meeting your dad, meeting Rachel, being with you."

My train was at one thirty so we had a late breakfast and Vicky accompanied me to the train station. Like those farewells on films we clung to each other until I had to rush onto the platform. With a wave I relaxed back into the seat and wondered about Monday morning, fearing the worst.

"You looked all fucked out!" Alison was up for the fight as I walked in.

"Don't you wish you were," was my retort.

She smiled, and remarked, "I think she was wishing that too, judging by the look on her face."

Cleevedreams
Cleevedreams
2,237 Followers