A Compromising Position - Ch. 01

"Oh my god! I'm so sorry, I'll give you a moment!"

Those were the words the office secretary blurted out, red-faced, as she quickly shielded her eyes with the printed PowerPoint slides she'd attempted to bring for my review. She slammed the door and I was left in deafening silence, partially crouched behind my desk, several orders of magnitude redder and more embarrassed than her, wearing only a bra and panties.

There was absolutely no doubt she had seen me. I'd been standing behind my desk, teasing my nipple through the thin fabric of the vintage, strapless bra with one hand, furiously tugging my small cock, poking out the leg of my full-cut nylon panties, with the other.

I don't think anyone else was aware of what had happened, despite her sudden reaction; no one was with her, and my office is down a side hallway. The only reason anyone is ever nearby is if they're coming to see me. I crouched, frozen, as my mind attempted to wrangle and comprehend the fact I'd just been caught by a female coworker, masturbating, in women's underwear.

Silvia was a beautiful woman, pretty much fit the hot secretary stereotype to a tee, and one of the friendliest people you'd ever meet. She was thirty-six, blond hair and blue eyes, probably somewhere around 5'5" to 5'7" with a slim build. Her body was amazing, perfectly curvy, and she always dressed to impress. Her breasts were, to my eye, perfect, despite never having seen more than cleavage. If I had to go out on a limb and guess her bra size, I'd say probably somewhere around a 32B. Although, to be honest, I don't think men, even those who crossdress, can realistically guess that with much accuracy.

That's all to say, I would never creep on her, at work or otherwise. It makes me feel extremely guilty to even think of her in a sexual or romantic way. I'm technically her supervisor, really just the middleman between her and the big boss, but she treats me as if I'm the boss. She is probably the politest person I know, and a people pleaser to a fault, often staying late or taking projects home to help ensure they get done on time and to the standard required, despite my protests. She's just an all-around great colleague, and an amazing person.

So, what would I tell her? Was I filming a kink video for a girlfriend? Maybe a guy friend would be more believable, given the circumstances... Did I tell her someone had blackmailed me to do it? No, that might raise more questions. Did I just ignore it and hope she pretended it never happened, and go on with our lives forever awkwardly interacting with each other at work, knowing the other knew, for the rest of our careers here? I didn't have much time to come up with a game plan, because a soft knock sounded on the door.

"Sam? Are you okay in there? Can I come in?" Silvia's voice sounded soft and concerned through the wood. I tried, and failed, to stutter out a response as I fumbled with the bra's clasp behind my back. Fuck, I should've started changing as soon as she'd first slammed the door! My heart jumped from in my throat, to practically falling out of my mouth as I heard the doorknob turn, and saw the door slowly crack open.

Silvia poked her head in through the crack and peaked around the door. She had a look on her face equal parts concerned, shocked, and curious.

"You don't need to change, and you don't need to be embarrassed about any of this or apologize for it," she tried to reassure me, "I'm so sorry I barged in like I did. This is your space, and you should have an expectation of privacy."

"There's nothing wrong with what you were doing. I know men have needs too, and it's just clothes, and I'm sure there are plenty of other men who have similar fantasies," she was bordering on 'verbal diarrhea' territory as she tried to diffuse what was likely the most awkward tension either of us had experienced in our lives.

I stood there, a thirty-three-year-old businessman wearing nothing but a bra and a pair of panties that looked like they'd been pulled straight out of the wardrobe of a middle-aged woman from the 1980s. I stood there; mind blank, unable to piece together a real-time picture of the events transpiring in my office that Friday afternoon in June. Silvia approached me slowly, her clipboard and papers clutched tightly in front of her chest. She silently set them on the corner of my desk and motioned for me to turn around. It took me a panicked moment, but I reluctantly obeyed.

As I slowly turned my back to her, I looked down, and was acutely aware of my predicament. The bra was black, the shiny fabric some sort of nylon and spandex blend. It was strapless and the thin cups, if you could even call them that, were unlined, clinging almost fully to my chest. I'd always had large nipples for a man, at least that's how the other kids made me feel in my childhood, 'you have girl nipples!' they'd tease. The thin fabric of the bra I was wearing seemed to accentuate them even more somehow. My gaze drifted further down, to the off-white pair of nylon Vanity Fair full briefs, a sharp contrast. They were just as shimmery as the bra, and had two little lacy window-like panels down by the leg holes.

My penis had gone completely flaccid, retreating almost entirely into my smoothly shaven abdomen, with only the head poking out above my little grape-sized balls. I was not a well-endowed man, not even remotely close to average in size. Because of this, I'd never had sex. There was one embarrassing moment in high school, when a girl who liked me had wanted to give me a blowjob under the bleachers during a football game. That ended exactly as you'd expect, and before it even began. Despite my tall, slim build, I was not a very sexually appealing specimen of a man, especially not when I was wearing women's lingerie, I'd imagine.

I'd gotten two of the three hook-and-eye closures undone, so the bra probably looked like it was about to rip in two as the last clasp held on and kept the undergarment secured to my chest. I felt her warm hands on my back, fiddling with the fastenings of the delicate bra. It was an uncomfortable sensation, not physically, the feeling itself was electric, but mentally that a coworker was helping me with a bra. I guess at least she wasn't freaking out and going to HR or, God forbid, telling the entire office about my secret.

Despite her, at least temporary, discretion you can imagine my surprise when I felt her not undoing the hooks, but refastening the ones I'd undone. I could feel my member inflating, both from the touch, and the knowledge she'd essentially put me, her boss, in a bra by securing the back.

"There, all better. I know this is uncomfortable for both of us, but I don't want you to change yourself or feel any shame on my account," she put a gentle hand on my shoulder and slowly turned me around.

"Oh!" she gasped, flustered, as my mostly erect, three-inch penis came into view, "I'm so sorry, let me just help you with that real quick."

My mind was on the verge of bursting into flames. What was happening? This was like the script of a porno, where the secretary offers to help the boss with his erection by jerking or sucking him off, or even having full on sex. Was I really about to get my first handjob, or maybe more, from my secretary?

The fantasy was not to be fulfilled, as she took my now-rigid little cock in her soft, warm hand, pulled back the elastic leg band of the nylon briefs, and tucked me back into my panties. The outline of its little head was visible against the smooth, ivory fabric, gently stretching it in small pulses in time with the rapid beat of my heart. Adrenaline was coursing through me, more than I'd ever felt, and my legs felt weak. She must have been able to see me shaking.

"Do you feel okay, do you need to sit down?" she asked, "we don't have to talk about this now, or even at all if you don't want to. I understand and don't want to make things weird between us. I can just leave you to your business."

Weird? She just caught me jerking off wearing a bra and panties, came in, redid my bra clasp, and then grabbed my dick in her bare hand to tuck it back in my panties, and she's worried talking about it would make it weird, of all things?

She leaned to the right, and in the process pushed her materials off the corner of my desk where they were precariously perched. With a surprised gasp, she quickly turned and bent down to lunge for them in a bid to keep her papers and pens from scattering. She failed but, in the process, her ass dragged across the front of my panties. The sensation of the smooth fabric of her tight skirt, clinging to her firm ass, sliding over my nylon-covered cock was too much for me.

I may have a penis well below average size, but I've always been an exceptionally heavy cummer. I watched in a concert of ecstasy and horror as rope after sticky rope of hot ejaculate shot through the thin fabric of my panties, and arced through the air to spatter in beautiful contrast on the dark fabric of her skirt. I groaned as the most intense orgasm I'd ever experienced tore its way through my entire body as I accidentally painted her ass with my cum, and she spun around on her knees to see what the matter was.

Our eyes locked, and went wide as the last few shots continued to blast through my panties, now bound directly for her face. Two splashed across her glasses, the next landed on her cheek and nose, and the final two went directly into her shocked, agape mouth, leaving a whitish film on her lips and tongue.

"Oh my god, oh my god, oh my god..." she whispered, hands held in disbelief as she realized she'd just unintentionally made her boss cum not only on her clothed ass, but on her face, and in her mouth. I took one last look at the scene: her covered in my sperm, my cock weakly pulsing in my now-soaked panties, and collapsed into darkness.

To be continued...