All Work and No Play – 01 Playtime

Another thing that Jake and have in common is that despite his boy scout veneer he is actually quite the sex hound. He doesn't necessarily look innocent like I do (his chiseled handsome features are much too manly to convey that), but he is just so sweet, charming and polite that no one would ever suspect how raunchy he can be. I also know my man, and I know he is secretly getting off on caressing Susan and given my approval he would be happy to fuck her.

Almost as if he is trying to prove my point I notice his semi-hard and growing cock start to push against the soft cotton of his shorts. The outline of his impressive dick becoming more visible and noticeable by the second.

I wonder if Susan is aware of his erection yet? Would she dare to mention it if she did?

Sensing that the time is right, I lean against her slightly and in a loud whisper say, "Doesn't he have incredible hands? I love the feel of his strong warm hands all over my naked body. He certainly does know how to touch a woman, don't you agree Susan?"

Jake is working his way up her right calf now. Her leg is slightly raised causing the bottom of her robe to fall open and slide to the side exposing the bottom edge of her nightie which is lying across her upper thigh.

"Ummmm," she moans softly, eyes all but closed, "Yes he does."

"You know what Jake told me? Back in the day, he used to have a number of housewives as clients and they would specifically ask for him to massage their tense naked bodies. He told me you'd be shocked at how many of them would beg him for a "happy ending". Can you imagine these middle aged soccer moms pleading with Jake to get them off?"

"Really? What did he do?" Susan says in a horse whisper, her voice catching in her throat.

"Well art supplies are expensive and those ladies were great tippers, so...you can imagine the rest," I tell her with a devilish chuckle.

Susan is clearly very turned on and almost seems to be in a trance as she softly responds, "Oh my!"

Leaning in closer I whisper, "Wouldn't you like to feel Jake's hands all over your tense naked body, Susan?"

I'm so close to her ear now that my lips are almost touching her.

She turns to face me and stares into my eyes. Her expression is puzzled as her mind tries to process if I'm really offering what she thinks I am. Our faces are now only an inch apart. Her cheeks are already flushed with her arousal, and her breathing is short and quick with excitement. I can feel her breath caress my lips and its sweet smell of chamomile tickles my nose.

"I would love that," she says softly, almost as if she is afraid that the sound of her words will spoil the moment and her chances.

Meanwhile Jake, who has been watching this scene intently, now has one of his large powerful hands on each of Susan's thighs and is massaging her legs just under the edge of her nightie.

"I'm sure Jake would be more than happy to give you a very deep, very penetrating massage. Working himself all the way into your tight, tense muscles, allowing you to fully release all that pent up energy and frustration you have," I say, trying my best to speak as seductively as I can. "Does that sound good to you?"

I doubt if she is aware of it but she is softly panting as she hangs on to my every word, mesmerized by the possibility of having Jake caress every inch of her naked body.

"Yes, that sounds wonderful!"

"The thing is, Susan, Jake is my man, so I can't just leave him with you unattended. I'm sure you can understand that, right?"

She looks a little confused but nods yes.

"If you want him to do all those things to you then I'm afraid I'm going to have to supervise everything. In fact, for the rest of this evening I will be in control, be the boss, sorta speak, and you will have to do everything I say. Do you agree to that?"

"Yes, whatever you say!" she agrees eagerly.

"Yes...what?" I have no experience at all in being domineering but I'm imaginative so let's see how this plays out.

"Yes Sir, you're the boss!" she looks so aroused I'm almost afraid she may orgasm before we even start.

"Untie your robe." I command her.

She doesn't hesitate to follow my orders and eagerly unties her robe, opening it up to give us a nice view of her fit body lying just under the silky nightie. Her stomach is flat and tight and her breasts are amazingly firm and full and perhaps a little larger than I originally thought. Her nipples are clearly hard and protrude easily against the thin material of the garment. In fact I can even trace the outline of her slightly puffy areolas.

I find myself thoroughly enjoying the idea of controlling what is about to happen. Finally Susan will have to do what I want and I'll control the narrative.

What I need to decide is how much do I want to physically interact with Susan. I'm fine with kissing and titty play but do I want to go any further than that? Honestly I'm not sure I'm ready to explore anything deeper with Jake watching. I think back to how much I enjoyed Emma eating my pussy and I wonder if I would have the courage to let Susan go down on me if she was open to it. I doubt it, but there is something incredibly thrilling about the thought of her doing whatever I tell her to do to pleasure me. Well let's see how things go.

Staring down at Susan's amazing body and incredibly sexy looking boobs I feel the intense tingling of arousal flaring up again in the pit of my stomach and between my legs. I need to see more of her.

"Susan, lift up your nightie. Let Jake see if you even measure up to his high standards or not. Perhaps you aren't even worthy of his attention," I say, hoping this kind of talk turns her on and doesn't dredge up bad memories of her ex instead. She gives me a sexy little grin letting me know that I'm on target.

Moving her hands to the hem of her night gown she slowly slides it up while simultaneously spreading her legs a little wider. There is still a part of my mind that is in shock that my boss is about to expose her body to us like this.

Jake grins broadly as Susan's beautiful pantyless crotch comes into view. Her vagina is fully shaved, and the delicate light pink folds of her labia pout cutely down the center of her hairless mound. Despite her legs being spread, the slender canoe shape of her sex is still mostly closed but there is a visibly glint of moisture at its lower end.

I'm pleasantly surprised to see that she is completely hairless down there. It's funny, I didn't give it any forethought but if I had to guess I would have expected a perfectly manicured and trimmed bush. Personally I'm fully shaved as well, and have been since my sophomore year of college.

Mmmm, what a pretty pussy. I want to see more.

"Spread your lips for him," I order.

She pulls the lips of her vagina open and the deeper pink core of her sex is now exposed and it's obvious just how aroused she truly is. Pre-cum glistens along her pussy's interior and clear fluid is flowing freely, dribbling now from her vagina down her taint to the crack of her sexy ass and starts to moisten the bottom layer of her nightie. At the top of her pussy her clit protrudes proudly.

I glance up and see that Jake's full erection is now eagerly pushing up the center of his shorts and I can tell he is dying to dive face forward into Susan's gorgeous sex.

"What do you think Jake? Does she pass inspection?" I say, surprised by a subtle tremble in my voice, betraying my own arousal.

"She looks very promising! But I should really take a closer look, do you mind boss?" he says looking at me for approval.

It takes me a beat to realize that by boss he means me. He's never called me boss before but often calls Susan that. It's really hot that he is playing along with this little scenario we're putting on.

"Yes, thoroughly examine her," I tell him.

Jake slides his hands under Susan's thighs and grabs her legs up near her ass and pulls her to him. Her butt slides forward but her nightgown stays where it is so she ends up bare assed at the front edge of the couch.

His face hovers an inch away from her splayed crotch and he enhails the sexy musk of her open pussy as he stares at her glistening hole. Instead of pressing his mouth straight against her sex he prolongs Susan's wait by gently kissing the inside of her milky thigh. Susan gasps softly, then unable to stand the suspense any longer grabs Jake's thick dark hair with both hands and pulls his head hard onto her long neglected sex.

Bending over Susan, I move closer to get a better look of Jake eating her pussy. It's kind of remarkable that I don't feel jealous. In fact, if anything it actually looks incredibly hot to see my handsome lover's face between her gorgeous legs. It's so sexy to see his tongue swirling around her pussy. He alternates between lapping the length of her pussy with light, rapid flicks of his tongue that flash teasingly across her erect clit.

Mmmmm, he drives me crazy when he does that.

Susan moans arching her back in ecstasy. I pull the thin strap of her nightie off her shoulder exposing her beautiful left breast. Her nipple is fully erect and pointing up at the ceiling. Slipping my hand under the bottom edge of my tee shirt and up between my naked legs, I slide a finger into the slick velvety folds of my pussy as I lean over and stroke Susan's nipple with the tip of my tongue.

Susan moves one of her hands to the back of my head and grabs a fistful of my hair, much harder than Jake would ever do, and forces my face firmly to her boob. Sucking Susan's entire areola into my mouth, I run my tongue around the whole area. The skin of her breast is so amazingly soft and so very different from Jake's hard muscular body.

"Harder Alice, please boss, suck my tit harder! Bite it!" she moans.

When I'm very horny I like my nipples pinched and nibbled so I get where she is coming from. I take the hardened flesh of her nipple between my teeth and I compress it trying to judge the proper amount of pressure to apply. Instantly Susan gasps and moans with approval as I chew on her tit.

Glancing back down along her flat belly and between her thighs, I watch Jake slurp and suck on Susan's leaky pussy. Its amazingly erotic to witness him pleasure her this way.

I know first hand Jake's oral artistry and watch with knowledgeable envy as he paints the full length of Susan's pussy with the broad flat surface of his tongue. Every so often he buries it deep into her hole, then drags it up the cleft of her pussy before circling her clit with its tip. Just to change things up he sucks on her clit or gently tugs and stretches her labia with his lips.

Susan is moaning and groaning loudly now and I'm concerned that Jake's skill combined with Susan's long neglected desires is going to lead to her cumming any minute now. I realize I need to pause the action here because I really want to prolong her arousal as long as possible. It's such a turn on to see her so incredibly horny and vulnerable that it would be a shame for that to end so quickly.

"Okay that's enough of that!" I command them.

I can tell Jake is trying to obey but Susan is so close to a climax that her clutching hands won't release his head.

"Stop, Susan!" I snap, grabbing her firmly by the hair forcing her to look at me.

Reluctantly she relents, letting Jake remove his head from between her trembling thighs and leans back panting heavily onto the couch, her whole body shaking. Even though I was able to stop her before she had a chance to orgasm, she looks like the slightest touch will push her over the edge.

Panting hard, Susan finally manages to look at me sheepishly and says, "I'm so sorry, sir! It just felt so good, I...I couldn't stop." Then, giving me a wicked grin adds, "but I was disobedient and naughty and I definitely need to be punished, don't I boss."

What, punished? How can I punish her? Damn I'm out of my depth here.

"Ahhh...yes, of course, you must be punished," My uncertainty is obvious.

"Will Jake administer the spanking or will you, sir?" Susan says, guiding me.

Wow! I was not expecting that. Oh my God there is no way I'm going to pass up an opportunity to spank my boss! I laugh to myself.

"You were so very naughty we will both have to punish you!" I playfully scold her. "Turn and bend over. Jake, teach her a lesson."

Susan gets down in front of the sofa and bends over with her top half of her body resting on the couch's seat, and raises her nightie exposing her sexy round ass to us. I marvel at how Susan's tiny waist transitions into the soft larger curves of her beautiful round butt, and how her ass cheeks perfectly frame her hot little pussy as she awaits her spanking.

The area around her sex is glisten with wetness and looks so inviting. Staring at her sexy ass I can't wait to get my hands on her again and I wait impatiently for my turn to chastise her.

Jake moves in behind her; his hard-on so obvious through his shorts that it's almost comical that he still has them on. He glances over at me, not so much asking my permission to proceed, but more questioning if he should really do this.

"Do it Jake, punish her! She's been a very bad girl!" I say.

Even though the words sound so melodramatic, there is something very erotic about this whole thing and it's definitely turning me on. Jake relents and swats her ass with his large hand but not very hard and waits to see her reaction.

"Oh I was much more naughty than that!" Susan says, wiggling her ass with a sexy grin, eager for harder justice.

Jake tries again with a much firmer swat but it's still more playful than forceful. Even I can tell she wants him to spank her harder.

"Harder, Jake! Discipline her properly or I won't let you fuck her," I bark.

They both look at me and I can see the lust bubbling to the surface in both their eyes. He strikes her ass again but this time sharply. A loud slapping sound fills the room along with Susan's moans of pleasure. Jake doesn't hesitate and applies three additional swift smacks of equal force to each butt cheek. She is so aroused when he finishes that her body is trembling and she looks to be once again on the verge of an orgasm.

"Well done Jake. Strip your clothes off and stroke your cock while I take my turn," I command.

Watching Susan being spanked sparks a memory from back in my childhood.

For years my brother Alan and I spent one month of each summer vacation at my grandmother's farm. We helped her with chores and learned how to care for the chickens, goats and cows and how to ride horseback. We had tons of fun and a lifetime of awesome memories.

Alan is a year and four months older than me and as a child he was wild and unruly and often got into trouble. Nana was fair and loving but could be quite stern when it came to discipline. She was big on dishing out punishments and Alan seemed to have a serving or two per day. While Nana's sanctions varied to fit her mood and the crime, one of her favorites was the paddle.

Rarely did a day go by that Alan wasn't bent bare bottomed across Nana's lap receiving an "ass whoopin','' as she called it. I can still picture his rosy cheeked butt after a round with the paddle.

As we got older and had more diverse interests and a wider circle of friends, we spent less and less time at the farm, even missing a few summers during our high school years. The last time we went as "kids" was when I was a senior in high school and Alan had just finished freshman year of college. Alan had matured into a respectable young man by then, but he seemed to regress back into a rambunctious little kid as soon as we stepped foot onto the farm.

One day he was horsing around and knocked over Nana's favorite vase (a wedding gift from her mother) destroying it beyond repair. He apologized profusely but Nana was incensed all day. That evening he told me he wished she would just give him an "ass whoopin'" like when he was younger so they could just get past this.

I remember laughing, teasing him that I loved to see that. I was shocked when he went to where the paddle hung on the living room wall and brought it to Nana saying even though he was sorry, he understood that he deserved to be disciplined.

I was too stunned to even laugh as he unbuckled his pants; pulling them down to his knees along with his underwear. He must have felt deeply embarrassed standing there bare assed for what seemed like an eternity waiting for Nana to pull him across her lap and mete out his punishment. The sound of the paddle against his skin as Nana beat out 19 strokes, one for each year of his age, still rings out in my memory.

That image will forever be burned into my brain along with the sight of Alan's full erection when he finally stood to pull up his underwear and pants. Alan went straight to his bedroom and locked the door without muttering a word. I never understood what happened on that day back then, but watching Susan blissfully smile with each thump of Jake's hand on her butt cheek, I feel I now have a whole new insight into "punishment".

I bet Susan would have loved to feel the sting of nana's paddle. Hummm...I don't have that but....

"Susan get naked, I'll be right back."

Inspired by my Nana I hurry to my bedroom and retrieve my paddle style hair brush. When I return Jake and spa Susan are both naked and Susan is hungrily watching him stroke his dick just inches from her face. It's funny how they both look at me at the same time but with totally different expressions. Jake's face clearly saying, "Are you seriously planning to spank our boss with a hairbrush!?" While Susan's says, "God yes, give me some of that!".

I kneel behind Susan's splotchy pink cheeked bottom and press the back of my brush to the right side of her ass.

"You disobeyed me, Susan. Are you ready to receive your punishment?" I say sternly.

"Yes boss! I've been such a naughty girl! Please don't hold back!"

She's so excited to be spanked that I have to admit her enthusiasm is making me very horny. My wet pussy and throbbing clit are also screaming for some attention. I slip my hand back under the bottom of my tee shirt and slide two fingers into the slit of my vagina and rub myself as I slap the brush smartly against her ass.

The sound is louder and higher pitched than the sound Jake's hand made when he spanked her, and it startles me a bit. Susan yelps in pain and pleasure and arches her back in bliss. It's odd how pain and pleasure tend to be so closely connected. It's all stimulation so it really just boils down to one's perception, I guess.

Sliding the brush from her ass cheek over to the mound of her pussy I rub the hard plastic surface along her wet slit. Moaning with delight she grinds back against it. The back of the brush is instantly coated with her pussy juice. Striking down hard on her other ass cheek, droplets of wetness splash up from the impact of my blow. Susan yelps again and her moans turn into joyous whimpers and heavy panting.

Looking at me over her shoulder Susan gives me one of the sexyist smirks I've ever seen. She seems like a woman once again on the edge of an orgasm and I really wonder if she could actually cum from being spanked. A twinge of lust sparks my clit and I bring the paddle down again and again, each time with a little more vigor than the time before, striking it across the center of both ass cheeks just below her asshole and just above her pussy.

Susan yelps and gasps with each blow and her legs tremble as I bring the paddle back for the next swat. After the seventh or eighth strike she suddenly arches her back and groans loudly and I'm startled when a large amount of liquid squirts out of her pussy onto the carpet. She suddenly then collapses onto the seat of the sofa, convulsing in pleasure as liquid continues to spurt out of her.