Foot Tease Personal Assistant Ch. 02

Note: I recommend you read the preceding story for important context. It will help you understand how I got myself so thoroughly under the thumb of my new boss, Stephen.

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I showed up right on time the following Monday, a brand new "personal assistant." I was deliberately wearing a relatively modest blouse and skirt. I mean, I knew it wouldn't matter one way or the other what I wore - I was obviously in over my head. I guess the modest clothing just reflected my fear.

Stephen was perfectly nice when he greeted me, as if I hadn't the week prior agreed to be his...his what? Personal 'foot girl?'

Even though he had the upper hand in our new little arrangement, I still marveled at how the situation was so easy for him. Here I am, projecting fear-based tension into the air and he's no more wound-up than he'd be if he were looking at his lunch menu.

But it wasn't only fear that I felt. I felt sexual anticipation too. The two together represent a powerful mix of emotions. You should try it sometime.

Anyways, he greeted me, we chatted briefly about something or other - can't recall and it doesn't matter - then he asked me to check in with Tina, his secretary - she'd have some tasking for me to work on.

Tina was cool. A little older than me, attractive. I had to wonder if Stephen had ever crossed the line with her too. She gave no hint - I couldn't pick up anything anyway.

The tasking was trivial spreadsheet stuff, for which I was overqualified. Looks like I'm going to have to prove myself all over again. Or maybe, I've just been hired but there's really no job for me to do. The prospect of busywork for any extended period of time was depressing. I'm an intelligent bitch dammit and I need at least some level of challenge!

Tina called me at my new desk mid-morning and told me that Stephen asked that I swing by at some point.

I went immediately.

He was there at his desk. Again, here he was with a perfectly nice, if perfunctory, greeting.

Then, "Victoria, close and lock the door."

My heart felt like it was about to bounce out of my chest! Already?!?

I did as I was told.

He reached for his mobile phone, began recording.

I interjected, "Stephen, is this going to happen every time? You recording video?"

He looked me in the eyes matter-of-factly and said - flatly - "Yes."

Well, over to me, just like that! I shut up, said nothing.

He went on, "My personal request for this week won't actually happen until after the work day wraps up - I think I mentioned that last week, right?"

"Yes, I remember."

"I called you in here now just to do a little prep work."

"Ok."

"You good with that? Look, since I'm recording I think we can assume you're ok if you choose to comply. If you're not, simply say so - no repercussions, just like I promised. All right?"

"All right."

He reached into his desk drawer and pulled out some KY jelly in a squeeze tube. Set if off to the side and looked at me.

I was probably looking stunned standing there, cuz I was.

He then reached into the same drawer and pulled out a butt plug. A pretty big one. Like an inch at its maximum diameter.

Holy...shit...

"Remove your skirt Victoria."

Trembling, weak at the knees, I unzipped it and let it fall to the floor.

"Remove those panties."

Complying, I lowered them, noticing the wet spot in the narrow cotton lining that had soaked up my juices.

"I'll take those. You won't be getting them back. By the way, start wearing sexier, thong-style panties from now on."

I said, "Yes, sir" as I handed my panties to him across his desk. He inspected the wet spot, smelled it, then put my panties in his desk drawer.

"You know what this is, don't you Victoria?" he said, glancing at the plug.

"I do. But I've never actually seen one in person."

"Ok, since you know it is, I want you turn around...show me where it's about to go."

I obeyed, pulling the tails of my blouse up so he could examine my naked butt.

"Mmm. So nice. Bend over at the waist and spread your ass cheeks. Show me your butthole Victoria."

I obeyed. Pussy juice was honest-to-God beginning to work its way down one of my thighs.

"Flex your butthole for me Victoria."

I did. His totally smooth demeanor began to slip a bit. While he kept control of his voice, excitement crept in. I could hear it.

"Victoria, here, take the KY and lube up that pretty, pretty asshole. Put on a show."

I didn't know what a butthole-lubing-show is supposed to look like but I did my best. I had the KY all up and down my deep ass crack. It's deep. I have a full, round, nicely-shaped ass. I massaged my hole and it felt nice.

The circumstances probably contributed. Knowing this man's eyes were drinking in the sight of my round ass, my crack, my butthole, my pussy and its dripping juices - all while I was bent over in front of his desk - it was just out-of-control, insanely hot.

I was absolutely ready to suck dick, to spread my strong legs as wide as they go, to receive his cock.

But that wasn't what he wanted just now. He wanted this show, this show of abject submission.

"Finger fuck your ass Victoria. Fuck it deep."

I obeyed, one finger at first, eventually working in the tips of three. Slowly pushing them in as far as I could. Which wasn't really all that deep but it probably looked good.

Then he said, "Stand up." Once I had, he directed me to sit in the chair centered before his desk. As I sat down, feeling the fabric of the chair on my ass, he moved the butt plug toward me, to the edge of the desk.

"Before you put that in your ass Victoria, it should be warmed up - it'll go in easier if it's warm."

"So hold it there where I've placed it and suck it."

"Show me how you suck dick Victoria."

The thing was only maybe four inches long but I sucked. And licked. I pumped my head up and down. He kept recording. The metal did, in fact, get warmer in my mouth, absorbing heat from my full lips, my tongue swirling over it as I emulated cocksucking for him.

After a time, "That should be good. Take off your shoes and climb up here on my desk. I want you on all fours with your ass in my face as you insert it."

I obeyed, climbing up, a little awkwardly, but in position. As commanded.

The feeling of vulnerability was overpowering and intoxicating. It's a good thing I work out and my heart can take that kind of pounding.

"Lube up your new toy Victoria." He really, really liked saying my name.

I did so, squeezing a generous dollop of the thick (counterproductively cold!) jelly onto the plug. I positioned the tip of the plug, readying it to penetrate me.

And I pushed firmly.

It actually slipped in without too much pain. A bit, but not nearly as bad as I'd expected.

I could feel his breath on my ass and my pussy. I wasn't looking back at him but I was ready to feel his hands, his tongue, his dick.

But no. Didn't happen.

After a few more moments of drinking in the sight he'd created, through his commandments and my submission, he said, "Good. That's good Victoria. Keep that in place. It'll prep you nicely for this evening. Go back to your work and I'll see you at six."

Well, he'd said this was all prelude, but for fuck's sake, really?!?

I climbed down. Before I slipped my skirt back on, I helped myself to a couple of tissues from a Kleenex box on his desk and wiped my thighs dry. Both of my inner upper thighs were shiny wet. I grabbed a couple more for my pussy, a couple more for my ass crack. I threw them in the trash can beside his desk, pulled on my skirt, slipped my pretty little feet into my shoes and walked out. I doubt I'd been there more than fifteen minutes.

My pretty little feet... If I had normal or ugly feet, I wouldn't be in this position. It wasn't the first time my looks had gotten me into trouble...

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It's been a few years since all this happened so I'm a bit hazy on the rest of my day leading up to what was looking like my first ass fucking. More busywork, me kinda dazed, nervous, excited - I'm struggling just now, trying to capture the emotional stew.

The pressure of the buttplug, that feeling of spread-ness, fullness. The reminder of its presence anytime I moved.

It was all such an outrageous sort of thing to be doing in the office surrounded by people. I loved the feeling and the thrill of going about my day without underwear - my pussy and ass - naked. Even better - the buttplug - up my ass - right here in the office!!

And there couldn't be any doubt as to what was looming. Stephen was going to fuck my ass. I had no idea what his dick looked like. Hell, he hadn't even touched me. But I couldn't get the image out of my mind - that of some generic cockhead pushing into my virginal butthole and pushing deep into my poor tight, tight, tight ass.

At one point I went into the restroom mid-afternoon, and used the buttplug to buttfuck myself. I wanted to be ready and, more importantly, I wanted to feel it - I couldn't wait until six o'clock that night to feel it. Too much anticipation. I barely, just barely, avoided cumming in that restroom stall as I savored the slow in and out of the plug in my ass - as I imagined what it would look like from Stephen's point of view. That view, as I willingly accepted cock up my butt for the first time.

I calmed myself...steadied myself...and went back to the busywork, killing time. I focused on trying to avoid thinking about it. Not because I dreaded what was coming, not because of fear or the possible pain, not because of the risk of getting caught and embarrassed. No, I tried not to think about it because the anticipation was killing me.

In a few short hours, I'd gone from being someone who'd simply never seriously given anal sex any thought, to being barely able to contain an overwhelming desire to take cock up my ass. I said it to myself over and over, like some mantra, "I'm going to take cock up my ass" - the words, so dirty and delicious, evoking little twinges of pleasure from my clit and my ass. I wanted it and I wanted it as soon as humanly possible.

The place was pretty empty at a quarter past five, so I went by Stephen's office and gave him an inquiring look. Thinking to myself, now is good. Why not now?

Stephen asked, "Do you have something for me?" He meant, like, work stuff.

I stammered, "No, just checking in."

"Ah, well, appreciate that Victoria. But I'm a little busy with a few things" he said, glancing at the paperwork on his desk.

I lamely said, "Yeah, of course...if you need anything, holler." And lamely went back to my desk, subtly, but firmly, put in my place.

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Finally, six o'clock. I waited until exactly that moment, determined not to show up in his office even five seconds early. He'd made an impression with that last little exchange. I was to do precisely - precisely - what he said. Precisely what he demanded of his "personal assistant."

So I walked into his office at six on the dot and shut and locked the door without being told.

I strode over to the chair in front of his desk and sat down.

"How was your day Victoria?" Small talk. He's starting with small talk!! Fine...

"It was good. I like working with Tina."

"Good. So are you ready to begin?" Oh, so that was the small talk? What a relief...

"Yes, sir." Yessir comes from my military background. And it felt like I was addressing a senior officer. A superior.

Out comes his cellphone. Starts recording. No objection from me.

"First, let me ask...Victoria, do you consent to what we are about to do?"

"Stephen, I, Victoria [last name], do consent. In fact, I cannot wait."

"Good. Great, actually," he said with a warm smile....

"Ok...so, what do you think is going to happen here this evening Victoria?"

"I think you're going to fuck my ass Stephen" I said boldly.

"Excellent. That's exactly how I want you to talk to me. And that's also exactly what I'm going to do. I'm going to fuck your ass Victoria."

Confirmation, and with it, a heart-quickening shot of adrenaline, flushing through my whole body. All of me. So all-consuming that it almost drowned out the electric pulse from my clit - but not quite. It was delicious.

"However, Victoria, I've thought about this and I think that the first contact between us - the first actual touch between you and I - will be the tip of my tongue on your asshole."

Caught me a little off guard there but ok!

"So stand up and take everything off."

Thinking, "Here we go, oh my God, for fuck's sake this is incredible and I looooooove it."

I stripped everything off inside of fifteen seconds. He then took his time savoring his first look at my body. My big tits, hard little nipples, my bush, my naked shoulders and strong legs. He spent an extra little moment soaking up the look of my feet - he hadn't forgotten those.

"Get back on my desk on all fours - just like this morning."

I complied. Less awkwardly this time.

"Remove the plug and put it in your mouth."

I did so. Took my time, savoring the act of slowly extracting it from its new home. And then...ah, the shiny polished stainless steel was so warm in my mouth.

Stephen was taking his time too but eventually I felt his breath within my ass crack. Then his tongue touched...touched my sensitive little butthole.

It was heaven. I pushed back on his face a bit as he ate my asshole. God, this man is soooo into this and the new sensations were so, so nice. His chin occasionally grazed my pussy and I damn near exploded but blessedly didn't. His light stubble on my butt cheeks and within my ass crack gave me chills.

He gave me his phone and told me to "narrate." Without having any warning or practice, I hoped that I would be able to adequately comply. My job is to comply. And take dick in my ass.

"Stephen is eating my ass" I huskily breathed at his phone as I recorded my face.

"His tongue is entering my butthole. He's tongue-fucking my butthole. Uuunnnnngggggg."

"Stephen said he's going to fuck my ass...fuck my ass with his hard dick."

From behind me, "Is that what you want Victoria?"

"Oh yes! You have no idea! I've been thinking about it all day. My very first ass fucking...did you know that Stephen? You didn't even ask!"

He just grunted something incomprehensible as he stepped-up his asshole eating. Felt fucking, fucking amazing.

"Please do it now Stephen. I'll beg if you want. I'll do whatever, just put it in there please."

He stood up. He gently (nice!) helped me lower my feet to the floor, now on his side of the desk, my stance wide. Wide for dick. A familiar position, a different hole.

I heard his zipper. Some shuffling. Then, finally the heat of his cockhead moving up and down my ass crack.

"I can feel my boss's dickhead all deep in my crack." Trying my best to "narrate" into the lens of his phone.

"Oh, there! Push it there! Right there!!"

He entered me a little and the pain was pretty sharp. I still hadn't laid eyes on his dick. Maybe he was huge. Or maybe I'm just too new to this.

My gasp caused him to ease up on the pressure.

"It's ok, Stephen, just go slow ok?"

"I want it. I do want it. But go slow."

Into the camera on his phone, "Stephen has his cock head in his personal assistant's butthole. And she's ok with that."

"Go ahead Stephen, just fuck me." I was ready for it. Let's gooooooo!

I pushed backward firmly as he thrusted forward - and finally - there! Oh, fuck!!! The fullness!!! This is haaappeniiiinnnngggg!!

He slowly pumped, ever deeper. By the third stroke I could feel his balls tap my clit. Ohhhh myyyyy god!!

Maybe by his tenth plunge into my ass I could sense he was going to cum. He held it all the way in, balls-deep. I reached back underneath myself and grabbed those balls (which hung remarkably low!) and pushed them onto my clit, squeezing hard, grinding his big balls left and right, back and forth, across my pussy lips and my clit.

It was my first orgasm with a dick up my ass and it was different than any before. I absolutely lost all control. Squirt and my pussy juice just everywhere beneath me. I almost couldn't discern that he was - in those seconds - filling my ass with hot, hot cum.

When he could speak, he said, "Back on the desk." His hands were on my ass, pushing forward, repositioning me back onto all fours on his desk.

"Squeeze it out. Right here Victoria. On my desk."

I squeezed and pushed repeatedly. A nice puddle of cum pooled on his desk.

"Now climb on down and clean that up."

Moving forward, I got off his desk and went to reach for his box of tissues.

He caught my wrist and shook his head.

"No. Eat it."

I didn't even bat an eyelash, much less object.

He'd retrieved his phone which I couldn't recall dropping or setting aside.

I looked right into the phone's lens as I lapped up every last molecule of his creamy white, warm cum.

"What are you doing Victoria?"

"I'm eating my boss's cum...his cum that he just pumped in my ass."

"Good, Victoria."

He'd tucked his dick away before I got to see it. I didn't learn just what had been so deep within me. But what came out of the boss's dick tasted divine, tinged with my own juices.

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It had been an amazing day. Amazing. I loved how he "prepped" me, a masterful manipulation. And I loved how he used me. What a day!

I felt good as I got dressed, recovering. Hell, I felt great!

But then he said, "I'll see you next Monday. Take the rest of the week off."

Again? A week off? So that's the deal? This isn't a real job with a once-weekly fucking. It's not a job at all - I'm just his whore, and only on Mondays!

I started looking for a new job the next day. But I didn't find one for another two weeks...