Seducing Kevin Ch. 01

(This story is a follow up to my story 'Pizza Delivery')

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Dear Internet,

It had been a few weeks since my encounter with, as I like to call him, Pizza Daddy and I was looking for a new adventure. I briefly thought about cruising the local parks at night or finding a glory hole somewhere (giving, not receiving, of course) but Pizza Daddy's warning about random strangers kept rattling around my sissy head. The "gals" down at the gay bar I frequented also gave me hell when I regaled them about my experience. Sure, they thought it was hot as shit, and I am certain a couple of them had to fix the tape keeping their clitties tucked back. However, they also tore me a new one for being so stupid as to trust a stranger and reminded me that I was lucky the pounding I took was from a dick and not fists. Thus, I ruled out picking up complete strangers, and besides, cruising the park is the kind of thing skeevy guys on the downlow do.

So, what was a horned up little sissy slut like me going to do to get the thrill I needed? I had no idea until one day at work, the elevator dinged, the doors opened and out walked my answer... I was going to seduce Kevin Hunter. Who is Kevin Hunter you may be asking, and I will forgive you for not knowing, since he is lower middle executive at the company where I work, and that reminds me, I have yet to tell you anything about myself, really. I mean, you know about what is likely the most insane thing I have ever done, but, beyond that, you know precious little. So, ok, before I get into how I was going to seduce Kevin Hunter, I feel I should reveal more about me first.

I am almost 27 years old and my name is Jack but almost everyone calls me Jackie (sometimes Jacquelyn when I am dressed up fancy) and if you could see me, you would know why. I am not even close to what you could call a "manly" man. I am all of five foot seven and 120 pounds soaking wet. A generous person would call my looks and figure androgynous and a rude one would just call them girly. I care deeply about my appearance and kind of sashay though the world, so most people just assume I am the swishy sort of gay man you see stereotyped in so many movies and TV shows, but they would be wrong. That is right Dear Reader, your adventurous, slutty little sissy is bisexual, or as friend once said, try-sexual, as in, I will try anything sexual, at least twice, maybe thrice.

Ready for another shocker? Your super horny, does not give a fat frog's ass what you have between your legs if you are hot, thrill-seeking sissy was a virgin until my sophomore year of college. That was when I meet my first girlfriend (well only girlfriend so far) and she opened me up to so many wonderful sexual and sensual experiences that I became the slutty, sissy tramp you have before you today. I would love to expound upon her but that would take an entire story series unto itself (maybe someday?). Ok, so more about me...

I work for a medium sized international corporation that does business stuff as an IT professional and live in a nice suburb of one of the country's smaller large cities. I graduated with a computer science degree from a popular university that has a decent sports program, so most people are familiar enough with my alma mater to make small talk at the various social and professional events I attend.

I grew up in a smallish town somewhere in New England and, maybe surprisingly, had a pretty normal childhood, despite my less than boyish looks, largely because I did not let the other kids get the upper hand. When they teased me about my looks, I clapped back and eventually, around fifth grade, most of the other kids realized I was not an easy target and was actually pretty tough inside, and either accepted me for me or at least just left me alone. Of course, there were a few assholes who would not let it rest but, hey, that life right?

Anyway, by the time I finished high school, I was part of a middle ring of the popular crowd, but my sexual experiences were pretty limited. I had kissed some girls (and two boys), gotten a blow job and awkwardly fumbled my hands into a few bras, two pussies and around one cock. Well, I think that is enough about me and I know you may be wondering why I have been so vague about my personal details and I will just say I am not giving specifics to a bunch of perverts on the internet, however lovely you all are (see above re: complete strangers).

And now back to our regularly scheduled programing... my plan to seduce Kevin Hunter. Let me start by telling you about Kevin Hunter and you will see why I would want to seduce him and why it would be an adventure. Kevin is, to be blunt, a stone-cold Hottie McHotterson New Zealander in his early thirties. He is six foot one and a very fit 175-180 pounds. I saw him with his shirt off a couple of months ago in the company fitness center and, if my clitty had not been locked up in her cage, I probably would have been compelled to rub one out at work that day.

As it is, the thought of that day still makes me squirm in my chair a little. His face looks like someone took all best of the fresh-faced Hollywood leading men from all time and melded them into one and then topped it off with a real panty dropper of a smile. Finally, a mop of dirty blonde hair that was not too long, not too short but just the right length for me to wind my fingers in as I would... sorry, lost my track for a moment... Anyway, he is gorgeous. Now I know what you must be thinking, 'Anyone that good looking has to be so full of himself, his ego needs its own seat when travels,' but here is the thing, he is not stuck on himself at all. In fact, if anything, he is a bit self-deprecating, not to the point of no confidence, just more in a shy quiet way. Thus, the need to seduce him.

I first met Kevin when I was tasked with helping set up his local network access after he transferred to our little slice of corporate "heaven" from the Auckland office about six months ago. To say I was unprepared for the Adonis that greeted me at the reception desk on his floor would be the understatement of the year. Unlike many of my IT colleagues, I am usually quite glib and easily chat with the end users as I help solve whatever computer problem they may have created, more often than not. I do not remember exactly what I said as I stumbled over my response to his greeting, but I am sure it was along the lines of, "Uh, I'm Jackie from IT and I'm, uh, here to, well, here to get your computer set-up."

I do remember his sexy Kiwi accent making it hard to concentrate on activating his profile and installing the necessary security patches on the new PC and laptop the company provided him as we exchanged small talk in his office. Luckily, I have done that task so many times it is second nature by now and I was able to let my mind wander to fantasies such as kneeling before him as he pulls his cock from his pants, or running my hands through his hair as he kisses my neck and nibbles my ear lobes. There I go with the hair again, but my god the man has nice hair.

Since that day, I have seen him around the building on occasion, and sometimes we exchange pleasantries but nothing more. At this point, you may be asking, "But Jackie, how do you even know he'd be into you? What if he's straight?" While it is true that I have not gotten to him much better since that day in his office, I have my reasons. To start, I have a well-developed gaydar and he does ping, not super hard but rather in a, 'This guy is probably okay with a dick on his sex partner.'

Next, I routinely have lunch with and chat with the secretaries and receptionists in the building and, while nearly every one of the female ones (and few of the male ones) lust after him, they all report he is a perfect gentleman with the ladies and seems to be just genuinely friendly. And last, I know he is not married and does not appear to have a girlfriend. I looked at his employee record (I know, bad Jackie, but I had to find out.), and his emergency contacts are his sister and an aunt who also live in the States. Plus, his parents are listed as the beneficiaries for the company sponsored life insurance. So, put together, I figured I had a decent shot at seducing Kevin Hunter. The next question though, is how?

I knew I could not use my standard sexy moves, otherwise I would put on a school girl uniform and walk up to him, grab his tie and lead him to a supply closet or slip on a cute sundress and hop on his lap, wrap my arms arm his neck and ask him to be my Daddy. No, HR would have a stroke if I tried those moves, as successful as I think they would be. I had to be more creative with this one, hence, an adventure. I would push the behavior envelope as far I felt I could without getting fired.

Now that I had a direction, I needed to bait the hook and entice him to come over for a nibble before I set that hook and reeled him in. (I like fishing, what can I say. It is a "manly" activity I am good at and I have a lot of good memories around fishing with my dad in the Green Mountains.) I was obviously the bait, but it was the enticing part that took some thought. In the end, I decided to manufacture a simple problem on the computer in his office that needed an admin password to fix. The next question was how to dress the bait to make it as attractive as possible to my intended quarry.

In the end, I chose a casual Friday to enact my plan. That day I wore a royal purple lace thong, a pair of women's jeans that looked fairly unisex unless you were up very close and a plain green t-shirt under a grey hoodie. I intended for him to see the "whale tail" of my thong when I was in his office, so I picked purple to make sure it stood out on my pale skin. That morning I logged on to my workstation, broke his computer remotely and waited for the call from his floor that IT was needed. About 20 minutes later, my boss poked her head in my office and told me I was a lucky fellow since Kevin Hunter needed his PC fixed. (She knows some of my sexual proclivities and is ok with them). I slipped off the hoodie (It might cover the thong and ruin the plan) and nearly skipped toward the elevator.

When I got to the right floor, the receptionist just waved me through and casually as I could, went to Kevin's office. I knocked on the slightly open door to announce my presence as I pushed it open a tad more while saying, "Hello, Mr. Hunter, I'm here from IT to fix your computer."

"Come in," he replied and started to explain the problem as I entered his office, "I have no idea what happened. Yesterday it was fine, but this morning, when I came in and turned it on, this black screen came up with words I'll admit I don't even remotely understand scrolling across it."

"Let take a look," I said, doing my best to keep calm, his accent making my clitty jump and leak a little in her cage, "Oh, I see, for some reason, your computer doesn't think it has a hard drive with Windows installed on it. That is odd."

"Can you fix it?" he asked, sounding a bit worried, "Or at least get the files off of it? I have an important presentation in a few days and most of the work for it is on that computer."

"I can't guarantee anything, but I think I have an idea of where to start," I fibbed, of course I knew how to fix it since I broke it, "First, let me check the cables to make sure everything is plugged in correctly."

I got down on my hands and knees and crawled under his desk knowing full well that this was not an issue of unplugged cables. However, it did give my thong an opportunity to expose itself as my shirt rode up a bit and my jeans sagged down ever so slightly. I heard a soft gasp and figured my plan was working, so I wiggled my ass a bit for good measure before I crawled back out, not bothering to adjust my shirt or my jeans.

"Well, not a cable issue", I said as I turned to face him, "Now to check the next thing on the list." As I turned back to face the desk, I smiled a little because he looked a wee bit flushed. Figuring I would turn up the heat, I leaned forward at the waist to reach down and depress the on/off switch on the computer. I felt my shirt slide up my back a good bit, so I knew he got a nice view of my smooth back and an even better view of my purple thong. I straighten up a bit and grabbed the keyboard, still bent over at the waist and pulled up the BIOS. I had disabled the main hard drive earlier and now it was a simple fix of re-enabling it and then rebooting the computer. When the log on screen popped up, I turned around and smiled at the obvious blush in his cheeks.

"There you go Mr. Hunter, should be good as new," I smiled at him, "Seems the main hard drive got turned off somehow, but I've fixed so you should be ok."

"Thank you so much," he replied, "Can you stick around a few more minutes while I make sure my presentation is ok?"

"Of course," I said and moved to the side where I knew my butt would be in his peripheral vision. He sat down and logged on, opened a few files and sighed with relief (and also snuck a few peeks at my ass).

"Again, thank you," he beamed, "You really are a life saver. If I had lost this work, I don't think I would have been able to replicate it in time."

"No problem, Mr. Hunter," I said as nonchalantly as possible, given my clitty's current state of excitement, "If there is nothing else, I'll be going."

As I started to walk toward the door, he stopped me, "There is one thing?"

"Yes?" I turned hopefully, thinking this might have been too easy.

"You helped me set up my computers when I transferred here, right?" he asked, "But for the life of me, I can't remember your name. I do apologize, but I can be horrible with names."

"No worries, Mr. Hunter" I chuckled, "It's Jackie, and if you ever have IT issues again, feel free to ask for me directly."

"Thanks Jackie, I will," he said, offering a handshake that I held just a beat too long, getting another slight blush from him, "And please, call me Kevin."

"Ok, Kevin," I replied, thinking this went well, "And, now, I'd better get back. The computers don't just fix themselves."

With that, I left his office and headed back to the IT department where I did have several actual computer outages to resolve. During the elevator ride, I went over the encounter in my head and was rather pleased with the seed I had definitely planted in Kevin's libido. The rest of the morning was spent doing my real work. Over lunch, I had a brilliant idea for the next step in my plan to get Kevin on my proverbial hook. If it went well, I might be ready to set that hook and start to reel him in.

(To be continued...)