[MF] Eating Out Tom’s Assistant

I watched her hips sway slightly side to side as she walked into the kitchen. I couldn’t tell if she was put off by (or if she had even noticed) me staring at her, but my heart started to race at the idea that she was walking away perhaps a bit more lustily and purposefully than she had before. Undoubtedly, I was imagining things.are looking for, but I wanted to be upfront from the start. If you are just looking for plain ol’ meat-and-potatoe’s heterosexual sex, this might not be for you. Also, being part of a bigger whole, there is probably more background here than spicy sex. I know its not exactly this subs wheelhouse and i don’t except a flood of upvotes, but always love feedback from those who like this kind of writing!

….. …..

I sat out on the back porch of Tom’s house, sipping coffee and watching the morning mist evaporate as the sun rose higher over the horizon and baked off the moisture in the surrounding grass. It had rained the night before. Tom and I had curled up on a couch watching the late summer rain batter against the picture window in the study while basking in the warmth of the fire. We didn’t talk much, but just reveled in the moment; individually lost in our own thoughts, while fully aware of the other’s comfort and presence.

Between the warmth and solace of Tom’s arms and the rhythmic rain outside, I had eventually drifted off to sleep.

I woke up the next morning wrapped in a blanket on the couch. Tom must’ve moved off to bed in the night and not wanted to disturb my sleep. Feeling like I had earned my run of the house, I went into the kitchen to make coffee and then out to the porch to enjoy the sunrise on one of the padded loungers.

As I sipped and enjoyed the nature surrounding me, I reflected back on the summer I had been having so far. As a 20 year old living in a small remote mountain town I had never previously visited, staying in the guest house on the expansive grounds of a wealthy family friend; it had started out lonely. Not able to find a group of people my age, I had retreated into self-improvement, foregoing the pursuit of relationships in favor of physical and mental exercise, reading and climbing and doing yoga more than I ever had before in my life.

And then Tom had flipped the world on its head. The sex we had had the past couple days had filled me with passions and pleasures that I had never dreamed myself capable of. I could sense the change going on within me. Everything would be different from here forward.

I felt a hand on my shoulder and looked up to see Tom’s smiling face.

“Jack.” He said, a hint of disappointment in his voice. “I am extremely sorry I have to do this, but I just got word that a meeting was pushed up and I have to leave town for a couple of days.”

“That’s okay.” I said, trying to hide my dismay. “I’ll be here when you get back.”

“You’re welcome to anything in the house.” He said, apologetically. “Seriously, make yourself at home. Whatever you need.”

….

A few hours after Tom had left, I was standing at the granite-topped island in the middle of a kitchen that was bigger than the entire ground floor of my house growing up. In spite of the somewhat uncomfortably grand surroundings, I had taken very quickly to “making myself at home” in these luxurious accommodations. After admittedly spending a good half hour running around the ground floor hallways in just my socks and sweatpants, seeing how far I could slide on the hardwood floors, I eventually had wandered into the kitchen to make myself another coffee.

In the search for some cream liquor and a stirring spoon to spice up my brew, I stumbled across a drawer full of jars – all containing a variety of strains of weed. My jaw dropped. Tom had been holding out. Here I was, rationing the powdered remains of my once healthy summer stash, and all along Tom had this treasure trove in a kitchen drawer, right between the utensils and the dish rags.

Well, he had said that I was welcome to anything, I thought as I picked up a jar labeled “Mellow Sativa” with the words “for day use” scribbled underneath, and a pack of Zig Zags and headed out to the porch, excited for a very relaxed afternoon.

A couple of ripped papers and searches for spilled bud later (was always more of a bowl smoker), I was finally contentedly puffing on a loose canoe-laden joint, my bare chest soaking in the midday sun. As I was rolling my sweat-pants up to my knees – squinting from the smoke rising into my eyes from the doobie perched between my lips – I heard a car pulling up on the gravel driveway.

Paranoia and panic kicking in instantly, I fumbled the Scooby snack in a botched mouth-to-fingers transfer and yelped as the ember fell on my bare skin, quickly swatting it aside and exploding the remainder of the poorly rolled fatty – paper, ash, greenery and all – over the recently-swept patio.

I scrambled out of the chair and started trying to blow the reminisce down the cracks between the slats and planks of the porch. Just as I was pocketing the last of the still-good bud, I heard the back door open and close.

“Ummmmm, what are you doing?” Asked an amused female voice behind me.

I turned around. It was a woman who I had seen coming and going from the house all summer, but who I had never officially met. I had been a bit curious about her relationship with Tom, especially in light of recent events. She was older than me but younger than Tom, in her mid-thirties, with brown hair that usually fell about half-way down her neck but was currently pulled into a low bun.

Every time I had seen her around the property before, she was either coming and going in stylish business-formal pants suits, or lounging on the deck in thin summer dresses. Now, however, she looked dressed to do laundry at her parent’s house, flip-flops, a loose university-branded T-shirt and cotton boy shorts. I had spent a good deal of mental energy wondering if she was Tom’s girlfriend, relative, business partner or some combination of the bunch. And to be honest, I had found her slightly intimidating. It had only been a of couple years since I had gotten good at talking to girls my own age, but I had zero idea of how to approach or find common ground with a mature, self-realized adult woman. But her change in attire was disarming. With her looking more like an dorm RA than a board member, I found myself more comfortable in her presence than I had originally anticipated.

However, the cannabis-fueled dullness and paranoia had not yet abated.

“Uh…I..” I stumbled, struggling through the dry mouth. “I was just… um, sweeping?”

Laughter spread across her face as she brought a hand up to contain herself, her eyes full of amusement – peppered with a healthy amount of pity – as she looked down at my squinty, blood-shot eyes and dull happy slightly-bemused expression.

“Oh, Honey.” She managed. “How much did you smoke?”

I collapsed back on the lounger, closing my eyes.

“Just, like, half a joint.” I replied, adding: “The jar said Sativa”

I was a bit shocked at how hard and heady the weed had hit me, I wasn’t usually such a light-weight.

“Yeah…” She said, guiltily. “Sometimes I switch them just to fuck with Tom. He never knows the difference until he’s already smoked, and unexpectedly-high Tom is my favorite Tom. So…”

I heard her footsteps walking across the porch and opened my eyes, she was looking down at me, her shadow blocking the sunlight, looking very angelic in my pot-addled eyes as she reached her hand out. I couldn’t help but notice that she smelled amazing.

“I’m Sarah.” She said, reaching out a hand. “Tom’s PA.” Continuing when I still looked confused; “Personal assistant.”

“Jack.” I replied, taking her hand. “Tom’s, um… guest.”

Sarah laughed… perhaps a bit too knowingly, I thought. And as I looked up into her eyes and felt her hand in mine, I felt the familiar warmth in my groin and a sudden slight twitch in my cock. I was suddenly very aware of my lack of clothing.

Well, I am certainly not gay. I thought, dropping the handshake and sneaking a glance at her ass as she walked back to the house, leaving my stoner-brain to wonder whether or not I had actually said that out loud.

***

Sarah, it seemed, had also earned carte blanche status with Tom’s house and in a few minutes returned and fell into the seat next to me dressed in a bikini with a sarong wrapped around her waist holding joint (much better rolled than mine) in one hand and a rose colored cocktail in the other.

“So, he’s told me…” She started. Pausing to light the J. “But refresh my memory. How do you know Tom?”

There was no accusation to her tone, just the kind of ice-breaking friendliness I had come to associate with my host.

I explained how Tom and my Uncle knew each-other through work and started on the explanation of how my uncle had lent Tom his apartment and how Tom was repaying the favor by having me stay for the summer when Sarah cut me off.

“Oh, you’re Dan’s nephew!” She said, the realization dawning on her. “That’s right, he wanted you to get a taste of some non-city life, right?”

“Something like that.” I laughed. “But now I think he just wanted to give me a taste of the rich-life, tempt me into finance like him.”

“And what do you want to do?” She asked, looking at me kindly while shielding the sun from her eyes.

“I’m not sure.” I said, truthfully. “Always thought I’d maybe like to be a writer thought

“Hey.” She said, turning back and closing her eyes. “Some writers have houses like this, not many, but…”

We talked easily for the next couple of hours. I could see why she and Tom must work well together, she carried herself with the some effortless, contagious confidence that he did; picking up lulls in conversation with ease. As we talked, my eyes found themselves drifting over and taking in her body, basking in the sunlight, noting the tiny colorless hairs on the smooth skin surrounding her belly button, imagining her muscles reacting to my hands as my fingers drew themselves across her soft velvety…

“Jack?” She cut in. She must’ve caught me day-dreaming.

“What?” I blinked

“I asked if you wanted anything. I’m going in the house.”

“Oh, um, I’m good.” I said without thinking, but as she turned to go: “actually, some water would be nice. Thanks.”

I watched her hips sway slightly side to side as she walked into the kitchen. I couldn’t tell if she was put off by (or if she had even noticed) me staring at her, but my heart started to race at the idea that she was walking away perhaps a bit more lustily and purposefully than she had before. Undoubtably, I was imagining things.

Just as I was contemplating how it might effect things with Tom if I wound up fucking his assistant, I heard the door open behind me.

“Hey Jack. Come here.” Sarah called. “I think you should see something.”

I followed her into the house and through to the media room on the second floor. Tom had a small indoor theater with a plush leather couch set between two reclining chairs with an additional row of four chairs set above and behind the first, all pointed at a large projection screen. Just as I was wondering what Sarah wanted to show me in here, I turned to see her push on a panel on the dark black felt wall and open into what must be the theater’s equipment room.

Sure enough a stack of DVD players and cable box receivers that must’ve controlled every TV in the house stood to the left of the open door. But the room also contained a standard office chair and dual-monitor computer on a shelf build into the wall.

As Sarah shook the mouse and the screen saver disappeared, my heart dropped. Across the two screen were dispersed twenty or so panels each containing a camera feed of various rooms and outdoor locations around the house. My stomach turned as I noted both the drawing room and second floor deck among them.

She minimized the windows and revealed a couple of video file icons on the desktop.

“Thought you might be interested in seeing this.” She said and double clicked the one titled “[Jack1.mov](https://Jack1.mov)”

Up sprung a quicktime video of the drawing room’s camera feed, cut from the moment that Tom and I first kissed. I stood transfixed, feelings of confusion and betrayal mixed with blood pumping arousal flooded my body. I watched myself submit to Tom, him sucking my cock as I writhed with pleasure, bending me over the arm of the chair, working my ass expertly with his fingers as I came spectacularly, shuddering in his grasp.

I had not even noticed the cameras around the house. This was well before the days of Nest and Ring where such things were commonplace. The thought that Tom had sought these recordings and spliced them out to be enjoyed later made the arousal swell even deeper with in me.

I felt a hand on my shoulder and almost jumped. I had nearly forgotten Sarah was there and suddenly felt a bit shy and fearful. But that feeling melted away nearly instantaneously when I saw her expression. She was smiling playfully. There no judgement, no jealousy, in fact there was a searching quality to her gaze that suggested she was curious about MY reaction.

“So?” She asked, a new tone in her voice. “What do you think?

“I….” I stammered slightly. “I don’t know what I… does Tom -?”

She cut me off. “I am the only other person Tom would show this to, don’t worry about that.” She took a step closer, I was very aware of my shirtless-ness and hard cock struggling against my sweatpants. “You see, one reason we work so well together is we, um… share certain interests.”

I couldn’t help but noticed her emphasis on “share.”

My first thought was: these kinky fucking old people, what the hell are they into? But Sarah was not old, the thought continued; older than me, sure, but no one in their right mind staring at those youthful eyes would ever conjure the description “old”. And then I realized I was staring into her eyes, and she into mine, her expression growing hunger and more lustful in the computer-screen lit room.

And suddenly we were kissing. Her soft lips pressed against mine; my arms finding their way around her waist and shoulders; my left had lightly gripping the back of her head as we pushed into one another; my bare chest against her breasts, feeling the material of her bikini against my skin. I could feel her hips grinding into me, her crotch against mine, rubbing her increasingly warming loins against the hardness of my cock through the fabrics of our clothes.

Thoughts of the past few days flew out the window as Sarah and I locked in our embrace. What room we were in, what house we were in, what was playing on the screen, none of it mattered as all my passion focused on Sarah.

All my dating life I had been the pursuer, the aggressor, the one initiating, but now found myself perpetually the prey; falling to the pursuit of two individuals who knew what they wanted and knew how to make you give it to them, willingly, but on their terms, at their whim. It stoked a wild desire within me, a desire to rise to their expectations, to prove myself up to the challenge of quenching their insatiable thirst. I wanted to pleasure Sarah, not in an effort to kindle her yearning for me, but rather to prove myself worthy of it.

I reached around her back and pulled on the bow tying her bikini top and let the fabric fall, pulling it over her head and taking in her amazing breasts. I held her left breast in my hand gentling squeezing and massaging the base as my lips and tongue slowly played with her nipples, feeling them stiffen slightly in my mouth and giving them a playful nibble, feeling her body react to the brief pain and moan and relax as my teeth loosened. I could feel her hands on my shoulders, urging me down. I gladly complied running my hands down her sides to her hips as I softly kissed her abdomen, her hands digging into my hair massaging my scalp.

I ran my nose lightly around her belly-button, letting her feel the heat of my breath on her stomach just above her waist. I pulled her bikini and sarong down to her ankles and studied the magnificent vagina before me. A trim but not hairless V leading to the soft pale outer lips, an ever-swelling clit poking out, begging to be pleasured.

She lifted her right leg onto the desk chair and pulled my head towards her crotch, pulling my mouth to her pussy tightly – my nose breathing in the sent of her skin as my tongue lapped hungrily at her clit; revealing in the taste of her wetness as her pussy twitched and pulsed in pleasure against my tongue and lips, her hips bucking involuntarily as she gasped and moaned – all the while firmly holding my face against her.

I felt her reach over me and her swaying lessen as some task distracted her. I heard a mouse click and the video start up again. She wanted to watch.

As the video of me being taken by her boss played on the screen before her, Sarah’s pace and enthusiasm peaked, my hands on her strong firm thighs could feel the shuddering waves of pleasure coursing through.

My tongue made its way around the entrance to her vagina, teasing her hole as she gasped: “Oh Fuck, yes Jack, keep going, just like that.”

I looked up her stomach, past her bouncing breasts and saw that she was alternating between looking down at me, up to the video and every now and then closing her eyes, her neck flexed in repressed pleasure.

Suddenly her knees gave a massive shake and I could feel the orgasm coursing through her body. That same primal urge was guiding her body as it had guided mine with Tom. Her hips bucked wildly, fucking my face independently of any conscious intention, just instinctively riding the wave of pleasure to completion.

When her body had calmed, she looked down at me, admiringly.

“Honey, that was incredible. Tom was right about you.”

She pulled me up to my feat and reached her hands down the front of my sweats over my underwear slowly but firmly running her hand along the shaft of my cock, breathing warmly in my ear, sending shivers down my spine.

I closed my eyes and raised my head, hips submitting rhythmically to her touch, lust and confusion battling in my brain. What in the hell was going on? As a rather sheltered college kid who had thus far walked a pretty run-of-the-mill sexual path -awkward romances with the intoxication of young love fueling passionate, but inexperienced sex- this kind of attachment-free hedonistic indulgence was entirely foreign ground. I had yet to realize just how fucking kinky “regular”-seeming adults can be.

As she rubbed my cock- which was now aching a bit uncomfortably against the restraint of my underwear -Sarah reached around and grabbed my ass firmly. Whispering lustily in my ear: “Come with me.”

Source: reddit.com/r/gonewildstories/comments/g6vc34/mf_eating_out_toms_assistant