M 5

In the year between college and grad school, I'd taken up running, lost a lot of weight, got in terrific shape, and felt like an all-around badass at the game of life. So it's not surprising, these long, fatter, lazier years later I'd want that feeling again.

As I drove the long hill up to the client's house, it brought to mind one of the hills I'd run back in Colorado. Strange as it may seem, hill days were my favorite. The greater effort brought a greater feeling of accomplishment. I glanced at the odometer about a 1/4 mile into the climb, then again when I pulled into M's driveway. About a mile. A good loop, I thought, with a steady incline. Hard to find around LA. I could park on PCH and jog up here...down up down up. New Year's was coming and I wanted to beat the rush of people turning over new leaves.

M is a regular client. She usually has a list of small handyman stuff that I can tick off in a few hours. A divorcee with two kids, she got the house in the split. It is a sprawling number, with one wing for the master suite and the other for kids' bedrooms. They're grown now, her son off in college, her step-daughter a grad student at Pepperdine. So M mostly has the place to herself. It is always immaculate and smells like a spa.

I take off my shoes in the foyer.

After some friendly catching up, she explains what she needs. Sure enough, it's a short list of items I burn through in two hours. As I gather my tools, I mention my running plan and ask if it would be okay to use the hose on Sunday if my hydration skills are as rusty as my running skills. M is more than supportive.

--Text me when you're coming and if I'm home I'll come out and cheer!

I assent, thank her, and head off to my next job.

Sunday comes and goes without the first run. On Tuesday, M texts me:

"Did I miss you Sunday?"

"Nah. Mr Lazybones didn't make it :("

"There's always next Sunday! Come on, you can do it! :)"

"Thanks! I'll let you know. Could always use that cheering!"

"I might be able to remember some from high school. But they'll be in Ukrainian if I do lol!"

Oh right. M is Ukrainian. Well, she's from the Ukraine, but she's been in the US for like 30 years, so it's only the occasional long "a" sound turned to short "a" that hints at an accent. I don't know much else about her; she mostly keeps to herself. Very short, small build, medium sandy blond straight hair most always pulled taut. The wiry bundle of energy type. I'm not particularly strong nor am I bragging when I say I could likely lift her with one arm, she's that tiny.

When Sunday arrives I will myself into some running shorts and lace up my sneaks.

"Lazybones got his act together. :) Prolly reach yr place by 9 if yr around"

The surfer traffic is light as I wend up PCH. When I reach the parking lot, I check my phone one last time: M hasn't responded to my text. Oh well.

As I expected, the opening strides of the run are horrible. Only two hundred yards in and I'm thinking: head back, sofa, six pack. But then a little voice chimes in, perhaps that badass inside me, and I press on.

Needless to say, by the time I reach the top of the hill, I'm in pain. Sweaty, salty, old man pain. And desperate for that hose! Rounding the corner, M's car comes into view, and I'm happy I'll see her. Stumbling closer on my shaky legs, I see a note on the front door.

[Hey R____, come in!]

Great, I think, some cold water, some air conditioning, and maybe even some Ukrainian cheers!

The cool air hits me in the most pleasant way. I carefully push the door closed and lean my head against it, pausing to enjoy the temperature change. I breathe deeply. A zen fountain bubbles reasonably in the foyer. The air is sandalwood. Hot, sweaty, concerted effort has given way to calm, reassuring comfort.

I turn and am about to call hello when I see another note. It sits next to a glass of water on a small table that's been placed in the center of the foyer.

"R_____ Congratulations on your first trip up the hill! Please enjoy the water--"

I sloppily chug it all down. So good.

She continues: "I am offering you a Blue Pill/Red Pill choice :). If you "take" the Blue Pill, you will leave now, and you can use the hose any time you like. If you "take" the Red Pill, you will come up to my bedroom and do everything I tell you to do."

Allow me to share the understatement of the year: I did not see this coming. Nor did I have to contemplate a response, because my cock was halfway to the stairs in anticipation. The only thing I did need to contemplate was how to hold myself back from sprinting to the bedroom.

As I round the corner on the first landing, I see another note a few steps up.

"Take off all your clothes."

Absolutely zero hesitation...though I felt badly to be leaving sweaty running clothes on her immaculate hardwood.

The double doors to her massive bedroom are open.

--Hello?

M rounds the corner. I'm disappointed to see I'm the only one naked. Even worse, she's wearing a long, slightly baggy dress. I'd almost call it frumpy. It's like I came to fuck and she came to teach in a one-room schoolhouse.

She skips the greeting and small talk, barely takes me in with her eyes, and beckons me to follow her into the bathroom. It's one of those marble jobs, double-vanity, soaking tub, frameless glass shower...quiet classy except for the gold fixtures. I fucking hate gold fixtures.

--Your running routine will be this: after each loop, you enter the house and strip naked. You come up here and take a shower. When you get out there will be a clean towel on this bench, along with an item of my choosing. It will be obvious what to do with the item. When you're done, go into the bedroom and kneel at the foot of the bed. Understood?

--Yes.

Without another word she exits.

Even worse than gold fixtures are showers with 14 different spray heads and 5 control knobs. It's a fucking catastrophe of water everywhere until I can figure out which knobs to use and how to turn up the heat. Ridiculous.

By the time I push open the steamed-over shower door, the towel is on the bench next to a pair of heels.

Now, I've never worn heels in my life, but I'm game to try. (Note to self: remember to ask M why she has heels in my size).

Clean, naked, dry...I click awkwardly into the room. M watches me come into view from a reclined position against some pillows on the bed. I can see myself in the large mirrored closet doors and I look silly. I mean, the fantasy is to be thin and hairless and girlish in heels. I'm the opposite. I chuckle at the reflection.

As I kneel at the foot of the bed:

--I look ridiculous.

--You look obedient to me. That's all I care about.

It was a good point and gave me something to focus on.

--Now, she says, working her way down the Cal King, Each time you come in here and kneel, you're going to eat my pussy until I come. As soon as I do, you take off whatever I've given you, go downstairs, put on your running clothes, and do another loop. Got it?

--Yes

She slides her legs off the bed on either side of me, then lifts the hem of her dress over my head. So it's in total darkness I first experience her sex. Already wet, a gentle musk, a small tuft of hair above...in short, heavenly. I waste no time piercing her lips with my tongue.

--Not so fast.

She pulls my head from beneath her dress and holds it.

--Today is all about the burn, remember?

A small smirk forms at the corners of her mouth.

--Get up to a squatting position and put your hands behind your back.

Once I obediently achieve the position, she pulls my head into her crotch.

--Now make me come.

It isn't long before my quads are screaming in agony. The first trip up the hill was enough to wreck them, but the added torment of holding this position for her is a real test of will. Add to that not getting to see her body...cruel and unusual indeed.

The more my thighs cry out, the more frantically my tongue attacks her slit. I'm licking, sucking, swirling, nibbling... I'm on her clit, sliding in and out, making circles around her lips...any- and everything I can think of to make her come and stop the pain.

It takes a good 10 minutes, then finally a moan. Like the Grinch hearing the Whos singing on Christmas morning: it started in low, then it started to grow. So I go at her for all I'm worth until at last she bucks and twists and thrusts herself into oblivion.

Wow.

--Wow, she manages.

I need to use my hands to steady myself as I stand, and the inrush of blood to my quads is searing. Lucky, I can step out of the heels, because walking in them would have sent me tumbling for sure.

Minutes later, the heat is a blanket thrown over me. I have trouble finding a rhythm...the pounding brings the runner's adage to mind: Uphill works the heart; downhill works the legs.

The surfing population has thinned considerably when I make the turn. The Pacific rolls peacefully beneath them as they bob in the tide.

Sadly, there's no concomitant peace on the hill. After much struggle, I'm at her door again. Slipping off my clothes in the foyer, I'm delightfully chilled by the conditioned air. The water glass, replenished, stands tall and fresh newly paired with a lit candle. My body is pulsing and aware from all the exertion. It allows me to trace the path of the cool drink down my throat and around the inside of my stomach. A few full, relaxing breaths and I'm off to the shower.

When I emerge from the shower, the heels are on the bench again, paired with a small butt plug and a bottle of lube.

Frankly, my dear, I like where this headed.

Plug in, heels on, my second journey into the bedroom is even more unstable than my first. I check myself in the mirror again and still look ridiculous. M is waiting, legs pulled up and back a bit, her frumpy dress in contrast to her tightly groomed pussy.

--How does the plug feel?

--I like it.

--So you've had some experience?

--Not my first rodeo.

I smile and assume the squatting position between her legs.

She smiles back, and with one hand draws my face into her sex -- our eyes locked together.

"Giddyup."

M is soaking wet from the start and comes in 2 minutes. Sweet relief for me, and with luck a sign of things to come.

I pull the plug in the bathroom and clean it, which seems like the gentlemanly thing to do. And the plug's on my mind down the hill -- I'm curious what the next step in the progression will be!

By the time I reach M's front door for the third time, I'm seriously considering telling her this is the last loop. I mean, my untrained legs are jelly now. Even stripping nude in the cool air doesn't hold the joy it had last time. I'm sloppy with the water again, and practically have to pull myself upstairs along the handrails.

But shower time is pep talk time. Not only do I confront the runner inside me, who, if he's going to re-emerge from his long hibernation needs to step up his game, I also confront the sexual explorer: dude, this beautiful woman has given you a gift and you're letting your mind get in the way. Don't make that mistake again! Seize the opportunity. See it through to the end!

I step out of the shower with a new attitude. Waiting for me: the heels, the plug & lube, and a g-string. Silvery-white. A negligible triangle of fabric that's no match for my erection, which shoves it aside. I've got to admit, panties do something to me. I mean, every time I've worked for an attractive female client I've thought about pulling out the top drawer of her dresser, maybe secreting off with a non-descript pair of her panties and rubbing them over my cock, coming on them, wearing them under my work clothes...and now I'm getting the chance to wear M's panties in front of her. Wow.

I'm a bit more stable walking out, actually anxious to see myself strutting in the heels and panties.

Well, I still look ridiculous, but I FEEL sexier, so there's that. :)

M takes a bit more interest as well.

--Looks like you're getting comfortable in those.

--I'm enjoying the challenge.

--And I'm enjoying putting you through it.

With that, she lies back and kicks up her legs, this time pulling them up close to her head. The motion moves the dress out of the way and exposes her belly. The shot of extra skin hits me hard, and I eagerly assume the position and start feasting.

But this time around I decide to throw a quick rimming in to see if she says anything, one way or the other. It's one of my favorite pastimes, so I'm curious if we're simpatico.

My first trip over her asshole is brief, and I prime for it with an ever-widening circle that began at her lips. That way if she wasn't down I could claim it was simply a by-product of geometry. But there is no protest, and I find my way back for a slightly longer stay, which is also accepted.

Then I just fucking go for it. I mean, it's all locking into crisp relief: a woman I'd known professionally for 15 years decided to share herself with me, and now I'm lucky enough to have every exposed inch of her a tongue's length away from my face...gotta try it all!

I stab at her tight little hole with my tongue, pushing, probing then swirling and licking. At first, she doesn't make a sound. Does that mean no? But then I flick my tongue rapidly, but barely touching, and she responds, still soundless, by reaching both hands around her hips and pulling apart her cheeks. A resounding yes!

The stay at her butthole is brief, however, as my quads complain they've had enough of the squat. So I dutifully return to her clit and get M off in under a minute.

Pushing off the bed to stand, I reconsider the reconsidering I did in the shower. The pain is burning through my sexual resolve.

--I don't think I can make another trip. I'm sorry. Please don't think I'm not loving every fucking second of this experience. I just...my legs are killing me.

M slides to the end of the bed.

--You don't think you can make it just once more?

She brings her right hand up under my balls and caresses them gently. It's the first time she's touched me.

--Just once more, for me?

Her fingers move so delicately, they send mini charges up into my center.

She slides off the bed onto her knees and looks up at me. Her left hand encircles my cock, and the pair begin a delightfully well-synchronized routine.

I'm floating on the sensations M is creating between my legs. My neck loosens and tension leaks out of every part of me. As I drift, I catch sight of a koa wood box on her dresser. Likely for jewelry, as it has a lock, key sticking out. Inside, my languid brain imagines, are all the turn-ons this moment is hinged upon. Memories of my interactions with M through the years, that first surge of sexual energy brought on by the note on the table, being naked before her for the first time...and all my naughty luggage unclasped, unzipped: my panty fetish, my love of femdom, rimming, plugging myself, seeing myself in heels...all that swirling around in the box, mixing with the taste of her sex and the view of her spread legs bent up and back, the shape of her ass, still only half-seen, and the strange power of what I imagine her full ass looks like, everything rising to converge in a grand crescendo...yes yes yes the real and imagined in equal measure, equally capable of stirring...actions, feelings, memories, and hopes all pent up in a single box, with M holding the key.

And now she's on her knees, turning it with her hands, her eyes, about to release the concoction our weird and wonderful bodies and brains have merged to create.

She's moving faster now, though not increasing her pressure, nor taking her eyes off mine.

--You want to spurt your hot load?

--Yes.

Faster.

--You want to feel that surge of sperm into your balls, the tingling as I rub them...

--Yes

Faster.

--Do you want to know what I would look like with your come on my face?

--Yes god yes

--Have you thought about it before?

--...

--Have you thought about coming on my face before?!

--Yes!

Faster.

--All these years of knowing me just as a client. Just a regular person. And now you've seen and tasted my pussy...

--Yes

--You've even licked my asshole, my naughtiest little spot.

--Yes, yes

I'm at the doorstep of perhaps the largest orgasm of my life. The box of my desires is rattling, bouncing along the top of the dresser, the lid straining to burst the lock as M ever-so-slowly turns the key.

She takes her hand from my cock and reaches around behind me. I feel the plug push in slightly and clip my prostate. That in turn sends a buzz to the underside of the tip of my cock.

--I bet that feels nice.

--Yes!

In concert, her hands move the plug and caress my balls. I'm slightly relieved, because, while this combination doesn't feel as good as the previous one, I'm a step back from the frustrating edge M seemed intent on keeping me at.

--You feel that on your prostate?

She pushes the plug in and wiggles it slightly.

--Yes

--And the tip of your dick?

Still looking up at me, she extends her tongue until it presses warmly against the underside of my tip, and the direct wiring between there and my prostate crackles with electricity.

--Uhhhhhnnn...

M smiles and continues bathing me with her tongue. Information passes back and forth between our eyes, intensifying our connection with each wave of pleasure.

--Do me a favor?

--Yes?

--Tell me when you're going to come.

And with that, ladies and gentleman, Presto!...she disappears my cock into her mouth. An orgy of physical and mental pleasure ensues. It's the final turn of the key.

--I'm coming!

And with that...M simultaneously spits out my dick, stops caressing my balls, and unceremoniously yanks the plug from my ass.

It take me several seconds to collect myself as I spiral into letdown. M rises and smirks at me. I'm not amused.

--If you want that orgasm, which I would really love to give you...one more loop.

Goddamn it. With a mix of anger, disappointment, frustration, and a raging hard-on, I kick off the heels, pull off the panties (M grinning the whole time), and head down to my cold, sweaty running clothes.

But you know what? With all the emotional distraction, the loop was over in no time. Sure, my legs were feeling it, but my mind had another place to focus. I open the front door feeling triumphant for pushing through, and very much deserving of an orgasm of a lifetime.

When I step out of the shower, there is only a towel on the bench. But when I step into the bedroom...

M is standing proudly, naked except for a pink strap-on and a big smile. She points to the floor in front of her, beckoning me to kneel. I take my time crossing the room, eager to take in the sight of her body, now fully revealed. It is a wonder of compact efficiency, muscular and tight, pale and smooth. She's even freed her hair from the strict ponytail, and just that small gesture has transformed her.

Looking up from my kneeling position, the view of her face is obscured by the pink dildo, which she is defiantly waving over me. M pushes it downward in what I imagine is a universal gesture for "Hey, slut, stick it in your mouth". I oblige.

The experience, which I've had once before, is not unpleasant under the circumstances. And I can tell from the gleam in her eye she's enjoying the sight of the pink shaft obeying the sway of her hips and disappearing past my lips.

Soon she wants more, though. She orders me to get the small bench at her makeup table and set it in front of the mirror. Lying on it face down, my hands and feet can still touch the floor, and, with my head turned to the side, I can see us both in reflection. The bench is short though, and allows my cock and balls to hang free beyond the end.