Quid Pro Quo [MF 20s-30s / CD, Workplace, Gentle Femdom, Vanilla] - Chapter 6

(This is the next chapter in this story. The previous set of chapters is available here.)

6. Served to Satisfaction

My body felt electrified when I entered Macy's. I zig-zagged between the usual mob of weekend shoppers through the main floor like a woman on a mission; though, I didn’t know exactly what my game plan was exactly. I was counting on some unseen hand to guide my way to the right look for “my Adonis of a boss is my pretty maid for the evening.” I needed something sharp and respectable that wouldn’t look out of place on somewhere on their knees or wearing rubber gloves.

Believe me, I know just how that sounds! But our arrangement was very clear. My boss, the law firm partner, master litigator, and rising star in his field, was coming over to clean my apartment. And that was that … give or take a pair of patent leather heels, that is ...

That was it! Once I found a way out of the crowd with enough room to breathe and scan the shelves, I found myself in the women’s shoe department. And there they were, right within arm’s reach. A perfect pair of black Michael Kors kitten heel pumps in size 10--the exact right look in the exact right size.

(You may be wondering how I knew that. I have to confess that I had taken the opportunity, once or twice, to poke around inside Tanner’s gym bag while he was out for lunch. I know how pervy that sounds, but in my defense, I'm in Tanner's office a lot, his bag was wide open, his shoes were right on top, and ... okay, beyond all of that, I have no defense. I was curious!)

After I grabbed the heels, the rest of the outfit manifested itself in my mind. Something presentable and professional but undeniably feminine. From that point forward, I moved like a cheetah around the store. I could spot what I needed from two departments away. Sheer but durable beige pantyhose, lacy black briefs and matching bra with light padding, an emerald knife-pleated skirt, a black and gold belt, and a tight, long-sleeved black blouse with a v neck. I also picked up some makeup basics, enough to give him a foundation and some simple contours.

At check out, I could see the clerk glancing at the clothing sizes and sizing me up with her eyes. She must have reached the conclusion that I wasn’t shopping for myself (which is understandable, I’m not a supermodel but I’m smaller than my boss), because she asked me if I needed a gift receipt “for the lucky recipient of this lovely outfit.”

I couldn’t help myself. I figured I’d never see this woman again, so I replied in perfect deadpan, “Oh, no need, I’m sure this is going to fit him perfectly.”

She was enough of a professional not to react, but I could still see her pupils expand and her cheeks get red. Just a few weeks ago I would’ve done anything to avoid making someone feel awkward or uncomfortable in any way. Something was changing for me, though. Something that gave me a little power trip in that moment seeing the subtle mix of curiosity and shock in her eyes.

I rushed home with the energy of a kid on Christmas Eve. As soon as I got to my apartment, I carefully opened everything I had just purchased and it laid out onto my bed like the cutouts of a paper doll.

The ensemble was exactly what I had envisioned when I was in the shoe department. I have to admit I squealed out loud and did a little hop! I wishes Tanner was coming over right that moment, but I knew I had to put everything away before it wrinkled. I hung up the skirt and blouse, placed the underthings in a bag and returned the shoes to their box. All together in my closet, it felt like a presence had entered my apartment—something at rest that was just waiting to burst out.

It took me hours to fall asleep that night. My mind swirled over everything that had happened that day. I oscillated back and forth from giddy anticipation to panic over the thought of my boss walking into my apartment for our little … whatever this was. I even have a word for it, which only kept me up for another hour. I tried to calm myself down by picturing him as my little housemaid, which just riled me up in a way I can’t really describe.

Eventually I decided there was only one way I was going to sleep that night, and so I dove into the back of the bedside table drawer for something battery powered. After a few clicks, I had the settings just right for a slow, variable vibration that usually did the trick. I rotated the wand in a steady circle while I gently pinched one nipple then the other. I conjured up old boyfriends stopping by for a quickie. When that didn’t do the trick, I dove back further into my head to more experimental times of my life and that one night with Sally Jenkins at summer camp. My body kept teasing me with an orgasm, but it just wasn’t happening.

Things picked up a little bit as I imagined Tanner rolling up the nylons I bought him up his perfectly toned calves until they covered the black panties cupping his tight round ass. I was teetering on the edge for a while until the dread started to creep up on me that it just wasn’t going to happen.

But then something happened. Something new for me.

A vision flashed in my mind of a strong pair of hands reaching around my waist. One hand grabbed my side while the other gripped the vibrator from me. The hand brought an end to my aimless spiraling around my lips and jammed the vibrator directly onto my clit. I looked down and saw that the hand extended from a freshly pressed business shirt and jacket. The fingernails were finely manicured and painted a deep shiny red. The skin was perfectly soft and smooth. Then I heard a voice whispering right in my ear.

She was compassionate and caring but firm, like (oh my God, I can’t believe I’m saying this) a parent:

“You’re going to cum for me, right now young lady.”

And, well ... fuck.

That was that. And as it turns out, as much as it shocked me in the moment, I really needed that.

I woke up on my own that morning. Despite the fact that I’d only gotten a few hours of actual sleep, I sprung to attention ready to start the day. I don’t know if it was the body-shaking orgasm I’d gotten or my excitement for what was to come that day, but I was at full steam all the way from my bed to my shower to my desk. Tanner was there already, of course. Half of me wanted to jump into his office to yell, “Tonight’s the night!” From the way he nodded gently in my direction when I arrived, though, I could tell that he was in “work mode” and that ;;I needed to tone it down for the office.

I dedicated myself to putting in a full day’s work, both to help pass the time before our little adventure and also to pay Tanner back for the work he was going to do for me. I’m his secretary by day, he’s my maid by night. A simple quid pro quo. That made sense to me, even if it wasn’t a rationale I would ever say out loud to anyone else.

As focused as I was, I kept my feelers up all day for some sign that Tanner was as giddy-slash-nervous as I was. I’d glance at him sideways and give him a little smirk, just to see if he’d nod or wink back at me. I got nothing. He was cool as a cucumber. Part of me had to admire his stoic nature. Another part of me worried that he had snapped himself out of this little thing of ours. Then I saw that he had an extra duffle bag in his office, something in addition to the gym bag he often brought with him. And I knew that he was all in.

It made my heart glow.

Around 5 pm, he stopped by my desk and asked if he could walk me out. I suppressed a stupid smile and gathered my things. As we exited the front entrance, I suggested that we could either take the subway or grab a cab before he cut me off.

“I think I’ll take my own way,” he said with a nod of his head, and I understood right away that I had overlooked the optics of what we were about to do.

“Right,” I replied as I mentally slapped myself in the forehead. I mean, what could possibly be more innocent looking than a boss following his secretary to her apartment on a Sunday evening? Surely any coworkers who spotted us would naturally assume that he was going to throw on a skirt and some heels to scrub down all my surfaces in the most non-euphemistically way possible. “I’ll see you in a bit.”

“I’m … off to grab a sandwich,” he added, in the very loud and deliberate tone one uses when they surely aren’t declaring their intentions for any passersby who might be overhearing us.

Finally getting the clue, I shut my mouth and simply nodded as we parted ways.

As things went, I took the subway and he grabbed a cab.

When I got home, I was reminded of how much I actually and un-ironically needed a maid. I fought back the instinct to tidy the place up before Tanner arrived, insofar as that would defeat the entire purpose of his visit (well … for the most part, that is). I made a compromise with myself that I’d empty the garbage, hide away the hygiene products, clear out the expired food from the fridge, and stash away all of my underwear. Luckily, that still left plenty of dust and clutter for Tanner to handle.

I sat on my couch and waited, feeling every passing second and every beat in my chest. Then, just as I convinced myself that he must have changed his mind, the doorbell rang, and I nearly tripped over my own coffee table leaping from my couch. I managed not to crash face-first into the door and took a moment to steady myself before turning the knob.

For a split second, I thought that a very posh Doordash driver had the wrong address. Then I realized that Tanner had donned sunglasses and a hat, which it turns out work just as well as the movies say they do to conceal someone’s identity.

After a solid ten seconds of silence, he cleared his throat and looked around nervously.

“Oh, my god,” I spit out, breaking myself out of the spell this entire bizarre scene had cast over me. “Come in. Welcome. Make yourself comfortable. Mi casa es su casa.” My mouth just kept talking, as if all the different flavors of awkward I had in me might cancel each other out if spoken at once.

When I finally shut the hell up, he cleared his throat and muttered a polite “Thank you” under his breath. His nervousness had the dual effect of making me even more nervous yet somehow also nurturing. I had the distinct urge to pull him inside and assure him that everything was going to be alright, I wouldn’t hurt him one bit.

With the door closed and a chance to size up the place, he started to say, “So, where should I—“ before I cut him off.

“There’s a bag,” I said, my words spring-loaded in my throat, “there, by the door. I, well, I guessed about ... for the most part, that is ... about, you know, your sizes.”

He nodded and smiled as he lifted up the two duffle bags he had brought with him from the office. I understood immediately. He had come prepared with his own stash, just in case. Goddamn it, I so very much wanted to hug him and tussle his hair. But at the same time, I also didn’t want to slow him down. I needed my maid and I needed her now!

I giggled like an idiot in response and waved my hand towards the room. He nodded again, made his way into my bedroom, and turned to say to me before he closed the door, “You mind just making sure the windows? And the door?”

“All window shades are down and I’m locking the door now!”

He nodded and closed the bedroom door behind him. I had to sit down and take a breath. I could feel my heart beating in my throat. As I sat and waited, a wave of anxiety crashed over me. What if this was all a terrible mistake? Something we’d never come back from? Something that got me fired?!? And then another terrible thought hit me. What if he just looked ridiculous?

The voices of doubt battled in my head over which fear to focus on until I heard the click of the knob.

I stood to attention, I saw him standing on the other side of the doorway, and I gasped.

“Greater than the sum of its parts” doesn’t begin to do it justice. The heels gave his calves the perfect accent. The nylons encases his legs perfectly, and from the smoothness of his skin under the sheer fabric, I could tell he had given his legs the attention they deserved. There wasn’t a single nick or sign of razor burn. The skirt and blouse were just the right degree of snug to show off his fit without looking undersized on his muscular body. And I should’ve known it, but he had brought his own accompaniments in the way of bracelets and earrings that brought everything together.

He’d obviously had practice with makeup before that night. I had actually noticed before that he wore light foundation in the office. Always just enough so that, to the naked eye, he didn’t appear to have anything but flawless skin. His makeup wasn’t quite so conservative this time but it was still just right. He nailed a look that was somewhere between 70s Bowie and 80s Lennox. Somehow, he had even had time to spike up his hair just a touch with gel for androgynous effect.

His stance was also slightly different. Nothing exaggerated, more like an enhanced version of the same soft tilt of his hips that I had spotted in the first place. That little suggestion that there was more to Tanner than met the eyes. The difference was that his posture harmonized perfectly with his current attire.

He was the embodiment of masculine and feminine merged into one. He was magnificent.

I was obviously gawking a bit too long. It took Tanner actually clearing his throat like we were in a cartoon to snap me out of it.

“Um, so,” I stammered like an idiot. “You can start in the kitchen!” I waved my hands in that direction like I was on a game show. I wasn’t sure I was going to make it through the night without losing all my dignity.

Tanner nodded with a polite smile and picked up one of his duffle bags. “Off I go then,” he said. I had wondered before he spoke whether I would feel the incongruity of a masculine voice coming out of a feminized form. But like everything else, it somehow worked. He didn’t pitch his voice in any obvious way, but there was still a softness that he didn’t use in the office.

It was subservient without being submissive, if that makes sense. The voice of someone there to serve, not to surrender.

His heels made delightful little clicks on the hard wood floor. I tried not to stare too obviously as he bent over to open his bag in the kitchen. He nearly caught me as he turned his head toward me. Or maybe he did catch me—he was far too tactful to let it show if he did.

In my defense, to be completely honest, I was not thinking dirty thoughts about his stunning ass. At least, not exactly. Not entirely. The sensation in me was a mix of excitement, admiration, and something like pride. The thing about Tanner was that the workmanship was always on display. He was a living and breathing epitome of competency porn. Something about him could just make a person feel good about the human species can accomplish.

Alright, now even I feel like I’m going over the top.

As I reflected on my feelings, I started to realize that I needed to be doing something while he applied fifteen different specialized cleaning products to the various surfaces of my neglected kitchen. If you’ll agree with me that it was not appropriate—even under those exceptional circumstances—to sit there and ogle my boss as he scrubbed my dishes, gathered up my clutter, and dusted my surfaces, what the hell was I supposed to do for the next two or three hours?

I tried thumbing through a stack of chronically unread New York Magazine issues teetering on collapse next to my couch. That was futile. After a few minutes and a dozen stolen glances at my maid, I knew I just had to leave. If I didn’t get some fresh air, I knew my imagination would start to get the better of me.

“Okay, so,” I said as I grabbed my jacket, “I’ll head out for a bit and let you do your thing.”

Then I paused at the door, and I heard him pause at the sink.

“No problem, I’ll be here.”

He sounded so sure of himself. I wondered what it must feel like to be that confident in yourself no matter what you’re doing.

I didn’t want to wander too far, so I settled on the nearest drinking establishment a couple blocks down the street from my place. It was a perfectly tolerable dive bar that was usually just crowded enough that I could go unnoticed when I needed some low-effort inebriation. On most days, I knew better than to either stick around too long or to let my guard down. I was never really that worried about being in the place, but it attracted enough guys who were just drunk and down on their luck enough to think I came there to hear their dumbass lines that I knew to stay alert.

That day, however, I had trouble keeping my focus. My mind kept drifting back to my apartment and how unmoored everything felt. I knew how to navigate adult relationships by that point of my life. I hadn’t felt this far off the map in a while. All I had to go for reference were websites that ranged from “crossdressers are just like you and me!” to hardcore “sissy” porn with next to nothing in between. Tanner wasn’t bowering my panties for comfort, and I wasn’t about to buy a strap-on for him to suck off. Whatever this was exactly between us, I couldn’t pin it down. All I could do was admire how exquisitely he mixed his masculine and feminine sides, and how lucky I was to get to see that side of him.

Anyways, if I hadn’t been off my game, I would’ve clocked the tipsy dirtbag heading towards me a mile away. But I was off my game, and before I could react, I was engulfed in his godawful beer breath.

“Hey little lady, haven’t I seen your pretty ass here before?”, he slurred my way.

He wore an off-the-shelf Target t-shit, torn jeans, and a never-treated leather jacket he must have thought got more attractive with every water stain. He had the Fred Durst hair-cut and facial hair of someone who never stopped listening to 90s rap metal. I can’t believe this look ever worked for this guy, let alone thirty years after it went out of fashion.

“Yeah, aren’t you the unhinged asshole I called the police about the other night?” Again, if my mind wasn’t elsewhere, I would’ve known better than to say anything back. I would’ve just moved placed and tried my best to ignore him.

But something else was happening in me. I felt a different kind of outrage but also a different kind fo power in that moment.

Fuck this guy.

“What?!”, he spit back at me, almost stumbling backwards into someone behind him. “I’ve never seen you before in my life. Fuckin’ cunt.”

I saw his eyes turn red, and for a moment I thought he might actually punch me. You know, to prove that he wasn’t an unhinged asshole.

The crowd went silent at his outburst for a moment until the bartender came over to set the asshole straight.

“Hey, that’s enough!”

I had seen her before but didn’t know who she was. Still, her voice was unmistakable. It was the same voice I heard in my head the other night! That’s where I must have gotten it! Remembering just how hard she made me cum gave me a little shiver.

“That’s strike three. Beat it, pal.” She crossed her arms as she spoke, showing off the musculature of her bare arms revealed by the black tank-top she wore. Fred Durst furrowed his brow in response, but he quickly withered. He made a show of straightening his garbage leather jacket as he skulked out of the place. A woman (one or two of his previously strikes, I assume) shouted “Fuck off, loser!” as the door closed on his dumbass.

The crowd went back to their drinking, and I mouthed a “Thank you!” to my dirty blonde savior across the bar. She returned a smirk and an upward nod of her head that made me swoon a little. I knew better than to hit on the bartender, but I gave her a soft smile and a seductive wink as I gathered myself together to leave. I probably looked like a doofus, but she was kind enough not to roll her eyes.

I felt electric as I left. The adrenaline and dopamine were firing on all cylinders. Meeting the subconscious origin of a masturbation fantasy was not on my checklist for that night. It almost made me forget about the gorgeous work of art I had waiting for me back at my apartment!

When I returned home, I almost didn’t recognize the place. The wood floor shined in a way it hadn’t since I toured the place before moving in, and the walls were spotless from the baseboards to the ceiling. This wasn’t an apartment anymore. It was a model unit.

I was afraid I had stayed out too long to have caught Tanner on his way out until I heard the bathroom sink running. I caught my breath and patted down my top and pants in a knee-jerk reaction of anticipation of seeing my beautiful maid again. When Travis entered the room, though, he had already returned to his normal “peak male” self.

I was a little disappointed. All the same, seeing him still managed to wipe away every last bit of that goateed asshole at the bar from my mind.

“I don’t know how to thank you! This place has never looked this clean.”

He flashed me a grin that wasn't humility or vanity, just the confidence of someone who knew exactly what they were worth.

“Anytime. See you tomorrow. Oh, and by the way, impressive job on your part getting the sizes right. I know it's not easy to convert women's sizes to the male body.”

The way he said "male body," I can't really explain what it did to me. All I could do was smile and nod.

"Anyways, let's work out something in the way of compensation."

I knew he didn't mean anything more than money. And he knew that I knew it. There was a comfort in having that kind of understanding with a man that is better than romance.

And then he was gone.

For a minute, I couldn’t move. I just basked in the glow of a pristine apartment. Every object was in the right place. Every surface was immaculate. I was in a state of pure Zen. I moved like a cloud floating through the air. Nothing felt entirely real but everything felt perfect.

I got myself ready for bed, knowing I’d have the best sleep I’d had in a long time.

Somewhere in my head, a thought crystalized in perfect clarity. There was one more thing I knew I had to do.

I grabbed my laptop, flipped it open, logged onto my dating profile, and switched the “Looking for…” options from “Men” to “Women.”

To be continued in Part 7...