You're the Boss

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What happens when a hot couple play games with the Boss.
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© Bad Hobbit 2019

Author's note: I had two (unfortunately anonymous) complaints about one scene in this story, so I've changed it around a bit. Hopefully this will read a little better.

"Jenny, come round to this side of the table, please."

The way that Chris said it, it didn't sound like a big deal. He'd just cleared away after dinner while I finished my glass of wine and was about to pour another, so I got up and carefully, because of the heels, made my way around the table to stand between Chris and Andy. Chris smiled at me.

"You look gorgeous, baby. Now, pull your skirt up so Andy can see your pussy."

I must have looked at him blankly for a moment, as if I hadn't understood what he'd said.

"I -- I -- what?"

"Well, you do want him to fuck you, don't you?"

I really wasn't sure how to respond. See, Chris and me, we've been married nearly four years, and to try to keep sex exciting, we play games. He likes me to put on short, tight dresses with no underwear, and then for us to go out for a drink or a meal. We both normally come home horny as hell and fuck straight away. Sometimes we don't even wait to get home; we've done it in the car and even in the park, like a couple of randy teenagers.

Tonight, when he'd told me Andy was coming round for dinner, I had wondered why he'd asked me 'dress down,' as we call it. I guessed it would be a turn on; for me, sitting there opposite a handsome man who might suspect that I was naked under my dress, might admire my bum and legs, wiggling as I tottered about on those insane heels, but who wouldn't know that my pussy was already wet from subtly -- or not so subtly -- flaunting myself. And for Chris, the knowledge that I would be getting turned on by the situation, knowing that his cock would be hard inside his trousers, just waiting for Andy to leave so he could fuck me insensible.

For some months we'd been talking about fantasies quite a lot, and about who else we might like to fuck. It started with celebrities -- you know, him fantasising about me being Taylor Swift, me imagining him as Alexander Skarsgard. More recently it's got a bit more 'edgy,' with each of us suggesting friends or other people we actually know. One night, a week or two earlier, I'd suggested he imagine me as my friend Chloe. She's very sexy and likes to behave raunchily most of the time, and guys think she must be a total slut. Actually she's bi and she's propositioned me in the past. I even dressed provocatively, the way that she does, and wore a push-up bra to make my tits look bigger. (Mine aren't small, but Chloe's are big, false and impressive). Chris had reacted as expected, and we'd both come pretty spectacularly. Then a few nights later, Chris had suggested his boss, Andy, which had appealed, and he'd blindfolded me and made me imagine Andy fucking me over a desk in the office. I admit it had been pretty hot, and Chris had made me come quickly and powerfully.

Andy's divorced, and about ten years older than us; somewhere in his late thirties, I guess. He and Chris have been good mates since Chris started working for him, a bit over two years ago. They're members of the same gym and sometimes go running together. Andy has been to our house for meals and drinks a few times, and I do find him attractive. He's a little taller than Chris, very fit, has a handsome face with high cheekbones, curly dark-brown hair, and big dark eyes. He has a very confident and almost commanding air about him; Chris says that if Andy asks for something to be done, you do it without question. Andy also seems to have a permanent suntan, possibly from all the business trips he takes, and he knows how to talk to women -- well, to me at least. It's not all sport, cars, work and similar shit. And he listens and takes an interest in what I have to say, which I've found a rare trait in men.

So yes, it had been fun and quite exciting, sitting opposite Andy in just a figure-hugging, short, strapless Lycra dress, no bra or panties, wearing rather ludicrous heels, as we both smiled and made small talk and -- I guess -- flirted. I'd had quite a lot of Prosecco -- I'd drunk two glasses while Chris was preparing dinner, before Andy even arrived -- and I'd imagined that, as soon as Andy had left, my skirt would be around my waist and Chris would have his fingers, tongue and cock in my slit -- and deeper. I'd got very wet, just fantasising about it. Well, and I guess also reliving the fantasy about Andy fucking me over his desk, while I was actually looking at the man in question.

But now -- what? I mean, yes, we'd talked about me fucking Andy, as a fantasy, but not like this, in real life. Apparently, Chris had decided to pimp me to his boss.

"Hey Jenny?" I turned to face Andy, who was smiling up at me from where he was sitting.

"You're amazingly sexy, you know? Chris has a photo on his desk of the two of you on the beach last year, and you look so horny in your bikini." He looked me straight in the eye, reached up and put his hand behind my head. I bent forward and kissed him. It was a really nice, soft, sexy kiss. I enjoyed it. And then he slipped his hand between my legs and rested it on the inside of my thigh.

"If you think she looks horny in her bikini, just wait until you see her naked," Chris said from behind me. As we continued the kiss, and Andy's palm stroked up and down my thigh, Chris took hold of the hem of my dress and pulled it up. It didn't need to go far to expose my pussy. It seemed as though I wasn't going to have any choice in this. At that moment, I wasn't sure whether I wanted any choice -- or if I'd have chosen differently if I had.

"That's a gorgeous pussy, Jenny" Andy said, softly. "It's so smooth, and I really love the way the slit comes up so high at the front." His hand slid higher, until he was brushing the outer lips. I think I gasped. We broke the kiss and I stood up straight, looking down at him, smiling back at me.

He moved his hand around, gently stroking my pussy lips, while watching my face for a reaction. I guess he must have seen what he was hoping for; by then I'd already decided to just go with it and see what would happen. I opened my legs a little wider to give his fingers better access -- something he immediately exploited, to my considerable pleasure.

"Jenny also has great tits. Look," Chris said from behind me, before peeling the top of the dress down to reveal my breasts.

"Wow, Jenny, you really are special. Chris is a very lucky guy," Andy smiled back.

I should have felt insulted, degraded. Instead I was fizzing, enjoying the sheer raunchiness of the situation and the sensations coming up from between my legs. I just smiled back.

"Just to be sure, Jenny; do you really want this?" He gave me a quizzical look. I guess I must have thought for all of three seconds before I smiled and nodded.

"Fantastic. I've had a great meal, Jenny, but I feel like I'd like to eat again. Can I help you up onto the table?" He stood up -- as I say, he's tall, so even though I'm not small, and I had the insane heels on, he suddenly looked quite dominant, looking down on me. He moved his hands to my hips and -- apparently effortlessly -- lifted me so I was sat on the table edge. Chris had moved round behind me and lowered me so I was lying across the table, with a cushion under my head. I opened my legs, and Andy got to work.

It's not something I regularly discussed with my friends -- I guess the last time was probably with my best buddy Abi just after college -- but I assume almost every woman must like to have her pussy licked. Chris does it pretty well -- I come almost every time -- but it felt even better when Andy did it. Maybe it was just because of the sheer raunchiness of the situation -- my husband encouraging another man to do sexy things to me -- or maybe Andy was even better with his mouth. Whatever, I was soon writhing around and moaning loudly.

Chris soon quietened me down, by the simple act of tilting my head back and slipping his cock into my mouth. I quite like sucking cock, especially if the guy has given me, is about to give me, or is in the process of giving me, a good pussy-licking. In this current scenario, it was definitely a turn-on to suck Chris's cock while Andy licked my pussy.

For a while, I was just floating, totally lost in the sensations Andy was stirring up in my pussy, and the feel of Chris's cock in my mouth. I can usually take him quite deep, but as I'd recently enjoyed dinner and didn't want to experience it going the other way, I kept him quite shallow. Still, he seemed to be enjoying it, judging by the noises he was making. My own noises would have been even louder if it wasn't for the cock in my mouth. Andy's tongue had started with a steady sweep around my outer pussy lips, probed my bum -- ticklish at first, then seriously horny -- and then moved into my slit, dipping in and out of the other hole in between delicious excursions to my clit and back. Then he stuck first one and then two fingers up inside me and started teasing my G-spot like he was a virtuoso musician, playing a Stradivarius. I was bubbling over.

I was seconds away from orgasm when he stopped licking, lifted his head and said "Jenny. Do you prefer to be fucked before or after you come?"

His fingers inside me were keeping me bubbling, but I didn't want him to stop with his mouth. Sure, normally my first come in a session is my strongest, and it's great to feel my pussy throbbing around a thrusting cock, but, but...

I pushed Chris away and let his cock slide out of my mouth. "Please -- please make me come now, Andy. Then -- then you can fuck me if you want."

"Oh Jenny -- how could I not want to fuck you. That's such a beautiful tight, wet pussy. My cock is just aching to slide in there -- assuming Chris will let me?"

"If Jenny wants you to fuck her, I won't stop you," he replied.

Before I could answer, Andy's tongue returned to my clit, and for about the next two or three minutes, nothing coherent came out of my mouth. Sure, Chris's cock went back into my mouth for a while, and all I could do was make muffled moans as those two fingers in my drooling vagina were scratching an urgent itch, while Andy's tongue was dancing the light fan-fucking-tastic on my clit. After about a minute more of this treatment, my moans went up about an octave and my legs started thrashing around, as most of the area below my waist began to jump around involuntarily and every nerve ending in the vicinity started to register overload. Some short time later, I was finding it hard to breathe as a load of sticky fluid got squirted into my mouth. Clearly Chris was enjoying this as much as I was.

"No -- please! Stop! I -- I can't take any more! Please, please...!" I was gasping when Chris's cock fell messily from between my lips. Andy lifted his head and looked up at me, and slowly the spasms began to subside. I could still feel his fingers inside me, moving slowly now but still stirring up some aftershocks.

I struggled to sit up. Andy stood up again, looking down at me and smiling, his face glistening with my juices. "Christ, Jenny, you're even hotter than Chris told me. You look so horny with your gorgeous tits out and cum dribbling from your mouth. Wow!" Then, in a smooth movement, he pulled his polo shirt off over his head and flipped it onto a spare chair. He looked pretty damn good, naked to the waist; smooth, nicely sculpted, broad shoulders, well-defined muscles. Not classically 'ripped,' but just 'well-formed.'

"Andy -- Andy," I gasped. "Please -- oh fuck!" Having removed his top, he'd undone his belt, peeled his trousers down and, as I watched, slid his tight boxers off. His cock was hard, long and thick. He was bigger than Chris. He was bigger than other boyfriends I'd had before Chris. And he was going to fuck me.

He finished stepping out of his clothes, and stood up tall. He looked amazing. My legs were spread wide after my recent pussy-licking, and he just moved up between them and placed his hands on my inner thighs.

"Hey Jenny. You're gorgeous. You don't need to do anything. Just lie back, open wide -- and say 'Ah.'"

What I said as he pressed the head of his cock into my open vagina and then slowly drove it into me in one slow, firm, unstoppable movement wasn't exactly coherent. I think there were a few 'Oh my God!'s, a couple of high-pitched 'ohfuckohfuckohfuck's and a fair number of gasps and squeals. Andy's cock isn't in the Mandingo league, but he's certainly quite a bit longer and thicker than I'd become used to. Consequently, he was pressing on places that either hadn't ever been stimulated so insistently or maybe had never been reached before, so the experience was new, exciting -- and not entirely comfortable. But with Andy, he has this air of command that means you just do as you're told and take what's coming to you.

Talking of coming, having recently done so rather strongly and exuberantly, I was expecting this to be all about his pleasure. Yes, I was getting fucked by a very good-looking man who wasn't my husband, and that was obviously very exciting, but I rarely get to come more than once in a session, especially if the first time has been really strong. So I expected this to be about Andy using my pussy as his reward for some of the most thrilling oral sex I'd ever had.

Wrong! Andy clearly wanted this to be a mutual thing. As well as pushing that rather intimidating cock to depths previously unexplored -- something I soon found surprisingly pleasurable -- he seemed intent on finding and stimulating all of the pleasure zones along the way. He sort of swirled his cock inside me to stimulate any sensitive areas there, while rubbing his thumb over my clit -- something that should have had me squirming in discomfort after my earlier massive orgasm, but which now felt -- fantastic.

Meanwhile, Chris decided to get in on the act, leaning in to kiss and suck my nipples. And then -- then he reached under me and stuck a finger up my bum. Sometimes I like that -- it's naughty and sexy just before I come, and if it's there when I hit orgasm, it feels very hot with my arse gripping his finger. Right now it was the trigger for something explosive.

I'd already had a big orgasm, so this one was a real surprise. Everything went into contractions -- my pussy, my bum; in fact, just about everything below the waist. I was moaning like crazy and my head was thrashing from side to side when I felt Andy come inside me. It never occurred to me to ask whether unprotected sex with my husband's boss was a good idea. Feeling his extraordinary cock throbbing deep inside me was just the icing on the cake of a sex session I wouldn't forget in a very long time.

"That was amazing, Jenny," Andy panted, after he'd kissed me for a long time. His cock slipped out of me and a dribble of his cum followed. He picked up a serviette and pressed it between my legs. "You're so hot -- hotter than even I'd imagined. Hotter than Chris let on. That was such a mind-blowing fuck." He kissed me again, gently cupping my breast. I just felt this delicious, post-orgasmic glow.

Then Chris was next to us. "Wow, baby. That was such a turn-on, watching Andy fuck you like that. I'm already hard again. Why don't you have a quick shower? Andy and I will clear away, and then maybe we can have another drink."

Chris and Andy helped me take off the ridiculous heels and peel off my dress, which had been bunched-up around my waist, and then, as Chris had suggested, I headed for the shower. As I rinsed my pussy again, trying to remove some more of the copious amount of cum Andy had deposited inside me, I couldn't help remembering how good it had felt having him deposit it -- every deep, pussy-rippling thrust of it. I was getting wetter on the inside than I was on the outside.

I stepped out of the shower, dried myself and, with the towel wrapped around me, stepped out into the bedroom. The sight that greeted me was strange and unbelievably erotic. Lying on top of our king-sized bed were two naked men -- my husband and his boss -- both naked, both with fully-erect cocks. Chris was holding a glass of Prosecco out for me. If I hadn't known better, I might have thought it was a scene from some gay porn movie, but knowing that those two erections were for me, not each other, almost made me come on the spot.

"Hey baby. Have another glass of Prosecco. Then maybe we can decide who does what to you next."

Andy patted the space between him and Chris, so I just dropped the towel and climbed onto the bed, nestling between Chris and Andy, as each put a strong arm behind me. I took the glass from my husband, took a sip, and then mischievously dribbled a little on my tits. Without a word, both of the guys bent down to lick my nipples, which felt amazing. And then hands were on my thighs, and then fingers started teasing my pussy again.

"I guess you've never been spit-roasted?" Andy asked. I didn't need to clarify the term. Chris and I had watched enough porn together for me to know what that meant. And no, I hadn't, though I had sucked Chris off whilst fucking myself on a dildo that was stuck to the wall with a suction pad. But, apart from my very recent experience of being simultaneously penetrated by two cocks, that was an experience that had eluded me.

Andy looked into my eyes, saw my smile and asked "So, would you like us to spit-roast you?"

"Yes -- yes, please. Sir." I don't know why I added that last word. Maybe I felt that I liked the idea of being dominated a bit. Or maybe it was just to tease Andy a little more. Whatever -- it seemed to work.

"Good girl, Jenny. I think Chris and I should reverse positions. I've felt that delicious pussy already, but I haven't had the pleasure of that greedy little mouth. I know Chris has given you a protein shake. I think it's my turn." And then they were taking up positions on the bed, me on all-fours, facing Andy who was kneeling in front of me, while Chris knelt behind. My head went down and look the tip of Andy's cock between my lips. Chris pulled my legs wider apart, and I felt his cock press at my wet entrance.

And then I was being fucked at both ends. Andy's hands came down on either side of my head, and he proceeded to fuck my mouth, slowly and with shallow strokes at first, gradually speeding up and pushing a little deeper. Chris wasn't being so gentle. Maybe concerned that, having experienced Andy's bigger cock, my pussy would now crave something more forceful, he went in with one long, deep thrust, and started fucking me quite hard.

Normally I would have objected. I usually like to start gently, until my pussy has stretched a little, before the final, joyous pounding that generally gets me off. This time I'd already been stretched and prepared by Andy's amazing fucking, and my pussy was ready to take whatever it was given.

Fortunately, thanks to the time that had elapsed since dinner, so was my mouth. Sometimes I can take Chris really deep, though I try to leave it a while after I've eaten -- for obvious reasons, even though I don't have a particularly strong gag reaction. So when Andy's rather large cock hit the back of my mouth, I did gag a little, but fortunately nothing came out except a little throat-goo. I can take about four inches of Chris's cock in my mouth without it going through my throat. Andy was bigger, so the stretch was harder, and there still seemed to be more cock outside my mouth than in it. But although I know it doesn't sound like it, the situation was unbelievably erotic. Sure, I now had less than half of a thick cock that I guessed may have been between eight and nine inches long shoving at my oesophagus. However, I had a very fit, very sexy, very powerful man using my mouth as a fuck-hole, while my cute, sexy husband was pounding the fuck-hole that nature intended in a way that would probably make me come quite soon.