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Sophie , Simon’s Christmas Night In

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This can be read as a standalone story, but you will get more enjoyment if you read the “Weekend Working” three part story previously posted.


It had been several months since ‘that’ Saturday, when my boss, Simon, had rumbled my weekend shenanigans and punished me suitably.

The shenanigans I refer to are the two weekends, when I’d been fucked by the plumbers, when they’d come into our office to fix our toilets and kitchen tap. Prior to that, despite being fairly experienced sexually, I’d never been particularly adventurous. I’d never had a threesome, had anal sex or experienced domination. Over three successive weekends, my sexual barriers had been broken down and I realised how much I enjoyed feeling like a slut and being sexually submissive. As a self-confessed feminist, and having quite a strong personality, I never thought I would.

After that first time with Simon, he’d told me that he would be my boss, both in my job as an office manager for his very successful architect’s practice, Thompson and Partners, and sexually. I’d been a little reluctant the first time, but found myself masturbating every morning before work at the thought that he might want to fuck me again.

In the end, he’d teased me for two weeks, before he actually invited me in to his private bathroom and dominated me, one day after work. He’d made me get into the shower in my suit, and then sit at his desk taking notes in wet clothes and messy hair. He then asked me to read out my summary of the task in hand, whilst he undressed me and touched me, roughly tweaking my nipples and clit.

Each time I stuttered, he would hardly slap my clit. After that, he bent me over the side of the sofa in his office, and left me in that position whilst he went out for client drinks. After two hours, he came back and roughly fucked my ass. Walking home in my still damp suit, I felt sore, satisfied and eager for more.

For several months now, Simon found new ways to dominate me. Occasionally, it would just be bending me over his desk for a quick fuck, in whichever hole he pleased. Other times, it would be midnight before he would let me leave the office. Some weeks, he’d want me every day and others, he would tease me, but not actually touch me. He’d started to turn up unannounced at my flat some evenings.

On the last Friday before Christmas, which was the last day that we were open until the new year, I was in his office, on legitimate company business. When we were discussing work, he’d leave the door slightly ajar, and he’d not usually mix business with pleasure on work time. Sometimes, that would be how he teased me, he would say things that would not be suggestive to anyone else, but to me, made me think of the times he would dominate me. This time, he got up, checked nobody was outside, and shut the door.

“Sophie, I’m going to miss our evenings together over Christmas. With my lads’ ski-ing holiday, it’ll be three weeks before we’re both here. I don’t like it but I can’t do anything about it,” Simon said. Timing of the Christmas holidays, and the long-time booked holiday, was out of his control, and this frustrated him.

“Is that why you’ve closed the door?” I asked, feeling nervous. As much as we both enjoyed what we were doing, if we were caught, I’d most certainly be out of a job.

“No, no. I just wanted to ask, are you free tomorrow evening?” he asked.

“I’m out for a friend’s birthday,” I told him.

“Well, now you’re not. I’m having a little get together with the lads, kind of a pre-ski party, and I want you there,’ he told me. I could tell by the tone of his voice that saying no was not an option.

“But, my friends?!” I protested. Over the last few months, I’d seen them a lot less, and I think they were getting pretty pissed off with me for the amount of times I let them down last minute. As much as I felt guilty, I was enjoying this…whatever you want to call it…with Simon too much to stop it.

“Sophie, are you my slut or not?” he said in a hushed voice, by now having come round and perched on the desk in front of me.

“Yes, boss,” I responded. That was how he liked me to answer him.

“Good. Well, be there for 8. I want you to look perfect.”

“OK, boss,” I said, getting up to leave his office.

“I’m looking forward to it, and you should too,” he told me.

“What have you got planned?” I asked.

“I told you, the boys are coming round. Now, you’d best get on with your work, the office is shutting in an hour,” he told me sternly, before shutting the door behind me.

For the following 24 hours or so, I was tingling with excitement. I hoped that he wouldn’t humiliate me in front of his friends too much; though I had enjoyed the threesomes with the plumbers, I really did prefer one dominant partner.

On the day itself, I took time to get ready: a long bath, ensuring my pussy was smooth as that is how my boss likes it; I made sure my hair was shiny and wore it down; and my nails were painted Side Escort red, with matching red lips and a classy amount of eye make up to complete the look. That morning, I had bought some new underwear, being pink lacy crotchless knickers with matching suspenders and strapless bra. I then paired this with a black knee length pencil skirt with a long slit up the left leg, which would show the top of my stockings, and a pink halterneck top. I wore diamond stud earrings, but no other jewellery, as my boss doesn’t like it. Finally, I put on the patent Louboutin court shoes that Simon had sent to me two weeks ago, with instructions that he would tell me when I could wear them. A text received at lunchtime confirmed that this was that time.

Someone buzzed my door, just as I was about to leave to grab a cab from my city centre apartment to Simon’s Cheshire mansion.

“Miss Moore?” the voice asked.

“Yes,” I said.

“Mr Thompson has asked me to take you to his residence,” said the plum-toned voice.

“I’ll be right down,” I said. I shouldn’t have been surprised that Simon wanted to control everything, right down to ensuring I arrived and left he wanted, and not a minute earlier or later. As soon as I sat in the back seat of the car, my heart started racing and the butterflies in my stomach danced like never before.

I’d never been to Simon’s house, so when the driver pulled in to a long driveway, just outside of a well to-do Cheshire town just outside of Manchester, I looked out of the window in awe. It was a big house, with a big white door and three windows on either side of the door. There was a large garage at the side of the building, and a path at the other side of the house, which I guessed led to the back garden. I’d never seen such a big house.

The driver, who I’d named Jeeves in my head, pulled up outside the house, opened my door and then rang the door bell. “Mr Thompson, Miss Moore for you,” Jeeves said, when Simon answered the door.

“Thank you, good work,” Simon responded. Jeeves then got back in the car and drove back up the driveway.

“Come in,” he said, kissing my cheek. I hadn’t expected a warm welcome, but he was a gentleman, in that he took my coat and gave me a tour of the house. No funny business, just the same way that a friend or boyfriend would show you round their house. Maybe he could tell that I was a little tense and wanted to put me at ease, but I appreciated this, uncharacteristic for our relationship, show of consideration.

When we reached the swimming pool at the back of the house, he started to shed the gentleman mask to show his dominant self. “Nice outfit, the boys will like this,” he said into my left ear. He ran his hand up the slit in the skirt and flicked the suspender.

“Thanks for the shoes, boss,” I said. I knew he’d be pleased at my show of gratitude.

“You look sexy, sluttish even,” he said, running his hand over my ass. He then turned me round so we faced each other and we kissed, at first tenderly and then more and more roughly, holding the back of my head so as to stop me from pulling away.

After a few moments, he pulled away himself. “Not yet,” he whispered, running his hands up and down my sides.

“So, tonight, you will serve the drinks. Champagne at first but then anything they want,” he told me, emphasis on the word anything.

“I’ve never been a cocktail waitress or anything,” I confessed.

“These are blokes, I don’t think you’ll have much. But trust me when I say, if they ask for anything and you can’t do it, I will remember and punish you appropriately later,” he told me, smirking.

It wasn’t long before his friends arrived, 4 in total. Mike and Adam, who I had met once before a few years ago in a pub after work, and five minutes after a pair I’d never met, John and Paul. All five men in the room were attractive, early 40 something, men with varying degrees of ‘salt and pepper’ hair. All were single – though John and Paul both divorced – and so seemed to act like teenagers when together. They were all dressed in nice, bespoke suits, wearing their shirts slightly too tight and collar unbuttoned, with the exception of Simon who had his tie on. The smell of testosterone and after shave was intoxicating.

I did as I was told; serving champagne on arrival, and then when that ran out, whatever they asked for. Mike and Adam asked for bourbon on the rocks. When I first made Adam’s, he asked for more ice. I glanced at Simon, who gestured that he’d noticed this error for later. John wanted beer and I noticed the look on Simon’s face when he praised me for the head on the beer. Paul asked for gin and tonic, though I didn’t put enough tonic in for his liking, a point which Simon again noticed. My pussy moistened knowing that I had at least two punishments coming my way.

Once they all had their second drinks, they moved from the kitchen to the large sitting room which overlooked the back garden. “When you bring us drinks, I want you to Side Escort bayan make sure that you give the boys a good eyeful,” Simon instructed, before he sat down. Simon sat on the sofa facing the door, so he could watch me whilst I was stood just in the doorway, whilst the others spread on the other two large sofas.

So, I did as I was told. I stood at the edge of the room, only going to the kitchen to get more drinks, and ensuring I did as the boss told me. I could tell they appreciated the view both of my suspenders and my bra underneath the top.

One thing I noticed was that whilst the others were having several drinks, Simon nursed his one single malt Scotch whiskey for most of the night. After I topped this up, which wasn’t until 11pm, he then invited to sit me down next to him. The smell of the whiskey plus what was left of his aftershave made my nipples instantly stiffen. Simon held the glass to my lips and instructed me to drink it – I’d never had a guy feed me a drink before, but then I’d never been a submissive before.

“What do you think of our waitress tonight then, boys?” Simon asked his friends.

“Pretty hot,” John said, looking at the slit in my skirt, which Simon had emphasised.

“Yeah mate, need her all the time, I reckon,” Mike said.

The others two agreed, and all four briefly just looked at me, lustfully. “Well, she’s off duty now, so you’ve got to look after yourselves,” he told them. After initial protests, they accepted it and started talking amongst each other.

“You’ve been good tonight, slut, not the most natural waitress but…” he whispered.

Before he could continue, Adam suggested they make their way to the games room for a friendly pool competition, and after the men agreed, all got up and made their way. I stayed where I was until Simon took my hand and led me to the games room.

“You lads play each other, we’ll watch and play the winners,” Simon said, sitting down on the leather sofa in the corner. He immediately instructed me to sit on the left arm of the chair and stretch my legs over him, with my left leg crossed over my right leg so as to show the boys my suspenders. I didn’t feel comfortable like this, but I didn’t have a choice.

Simon kept his hand still on my left thigh, fingers underneath the suspender and tops of my stockings. Occasionally he’d drum his fingers against my skin, as though to tease me. All four men kept glancing over in between shots, every now and again making comments between themselves. I could tell this pleased Simon.

Eventually, Mike and Adam won. Meaning it was our turn to play. Pool is not my strong point but I guessed that Simon didn’t want me to play for my abilities with a pool cue. As I stood up, I flashed further up my leg, exposing part of my butt cheek. This did not go unnoticed by anyone, least of all Simon, who whispered ‘Slut!’ in my ear.

We won the toss and got to break. “Ladies first,” Simon said, gesturing for me to take the first shot. As I bent over to take the shot, I wiggled my bum a little – this is something I do automatically when I’m concentrating on a shot – and it amused the boys no end. Mike, in particular, was stood behind me, and told me that if he had an ass like that, he’d wiggle it for the boys too. Just as I took the shot, he reached out and groped it, which took me by surprise. I looked to Simon, and he just winked, before saying what a good shot I had taken.

This continued throughout the game, each time I took a shot, one of the guys would grope my ass. Firstly over my skirt, but then as they drank more, they became braver, and would run their hands up the slit of my skirt and rub my ass over or under my knickers. Simon didn’t once join in, preferring to watch his friends touch me. As much as I wasn’t particularly comfortable with this, I felt myself becoming moist every time I saw Simon being more and more turned on.

Our game eventually came down to the black ball, and I had first shot at it. When one of the boys went to grope my ass, Simon stopped him. I wasn’t sure why, but it did mean that I could actually concentrate on my shot. And, by some fluke, I actually potted it, meaning we won.

“Wow, I can’t believe we have been beaten by a woman,” Mike said.

“Believe it!” I said back. I rested by bum against the side of the table, though still standing.

“That was a good shot on the black,” John said, shuffling along so he was stood next to me on my right side, “You’re pretty good with a cue aren’t you?”

“Pretty lame line, mate,” Paul said.

“True, but she didn’t mind” John protested.

“I don’t think this one minds anything,” Adam said, as he stood on my left side and ran his hand up my leg, firstly following the slit and then under my skirt. When he reached the top, instead of going for my ass, he went to my front and immediately noticed the crotchless knickers I had put on earlier, for Simon. “Guys, she’s wearing crotchless panties!” he announced.

Simon’s Escort Side body language changed. From being relaxed at watching his friends touch me, he now had a look in his eye that I, by now, had seen countless times. He mouthed ‘slut’ to me from across the room.

“Simon, you didn’t tell us she was a such a slut,” Mike said. Adam’s hand was cupping my pussy.

“She’s the dirtiest slut you will ever meet,” he told Mike, and the others.

“Well in that case, I think we should take advantage,” Adam said. He then started rubbing my smooth labia, before rubbing my clit, and then he forced two fingers inside my pussy. I instinctively moved my legs slightly further apart, when clearly pleased Adam as he then added a third finger.

“Adam, mate, this isn’t any fun for us, we can’t see,” Paul protested. He then took my skirt and pulled it forcefully, so it ripped and was hanging off me. If Adam hadn’t been continuing to roughly finger me, I might have had more time to think about that, but as it was, the pleasure was all consuming. The other guys, Simon included, were enjoying the show, all rubbing their cocks over their trousers. I groaned loudly as I came, and afterwards, Adam made me lick his fingers.

“I think you should get down on your knees for my friends here,” Simon said, “starting with Adam, to thank him for what he has just done to you.”

I hesitated for a moment, but after Simon told me again, with much more aggression in his voice, I did as I was told. I unbuckled Adam’s belt, unzipped his trousers, and pulled them down to his ankles together with underpants. He’s the shortest of the group, but his cock was (as I would find out) the largest. I started by licking the tip, then running my tongue up and down the length, before taking his cock in my mouth. Adam put his hand on the back of my head and forced his cock so deep into my mouth that I felt it on the back of my throat. It wasn’t long before I felt his warm liquid fill my mouth and, as instructed by Simon, I swallowed it all.

I then moved on to Mike. He was the tallest of the group, but his cock was smaller than Adam’s, meaning that when I deep throated him, I had his whole length in my mouth. Whilst I was on my knees , I felt someone kneel behind me and undo the tie on my halterneck top and pull it to my waist. I felt hands roughly fondle my tits over my bra, and I felt my nipples harden with the rough play. Whoever this was, then stood back up as he heard Mike come close to orgasm.

After swallowing my second load, Simon ordered me to stand up. He then pulled off what was left of my skirt, pulled my top down over my hips and unfastened the strapless bra. He also pulled down knickers, so I was stood there in the stockings, suspenders and heels. He pressed himself close behind me, reached his hands round and pinched my nipples really hardly so I yelped out in pain, much to his friends’ delight. He then ordered me to continue with pleasuring his friends’ cocks.

Paul was next. He was the stockiest of all of them, and his cock had the widest girth. Because of this, it was harder to fit in my mouth, though Paul was most forceful of all when he pushed me onto his length. He kept tight hold of my hair as he face fucked me until he reached his orgasm.

John was last, similar in build to Mike, though a larger cock than Mike. He was quite gentle, letting me take my own time, only grabbing my hair as his orgasm overtook him.

“Sophie, I want you to sit on the edge of the pool table,” Simon ordered, undoing his tie as I did so. I did as I was told. Simon then stood on front of me, took my hands and tied them behind my back with his tie. I realised this was the same tie the plumbers had tied my hands with all those months ago. He then ordered me to spread my legs wide so I was on full display.

“Enjoy my slut as you wish – tits and cunt only though, boys, no asshole,” he told them. He then looked round at me. I returned his wicked look with pleading eyes, but he ignored me, and proceeded to sit on the leather armchair in the corner.

Adam, being the first to recover from the blow job, approached first. I’d already experienced his fingers inside my pussy, but now, I experienced his mouth around my tits, licking and biting, building an orgasm inside of me. He then slapped my clit hardly, before standing aside to give his friends a go on this slut before them.

Next, I had John and Paul, stood either side of me. John attended to my tits, biting my nipples harder than Adam had. Paul, firstly massaged my clit, and then pushed his fingers into my wet sex, first two, then three, then four and then, to my surprise, appeared to be fitting his whole hand into my cunt, forcing me to spread my legs wider. I’d never been fisted before, but it hurt as Paul’s hands weren’t exactly small. I could hear his grunts as he fisted harder and harder, my body started to get used to it and despite myself, I actually began to enjoy it. I could see Simon’s cock straining against his trousers as he watched this perverted scene in front of him.

John, meanwhile, was continuing to pleasure my tits and as his bites got harder, and Paul’s fisting because more and more frenzied, the combination caused me to squirt, much to John and Paul’s delight.

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