Gender Bending Investigations Pt. 05

It was the morning light filtering in through the window that finally stirred me. Something felt different. That wasn't saying much, the last few weeks had been a whirlwind of change. I'd been turned into a woman and sent on an undercover assignment. I lived in a new apartment, wore new clothes, and that was just the little things. For all of that though, I'd gotten used to the changes, even the new body for the most part. It was still plenty weird sometimes, but at least a familiar strangeness at this point.

No, something else was different this morning. I wasn't much of a morning person and it took my barely roused brain time to collect together my thoughts and the sensations. First it was too bright. My bedroom windows faced to the west and the morning sun was wonderfully subdued in the morning. I was also naked, and I never slept naked. Just as I was figuring this out, I heard a groan and a big arm flew up and over me, and I realized I wasn't sleeping alone!

That was enough to jolt my brain. I fought down the urge to let out a surprised squeal. I was in Patrick Oswald's bed. It had been surprisingly easy. Sure, the Agency had done their level best to remake me into the his ideal woman physically, and I'd managed to impress him with my data analyst skills, but it had barely taken a few days from meeting him to end up in this position.

It didn't help any that I'd actually started to like him. I guess this was always a problem with undercover assignments, especially ones that required this kind of close contact. I'd needed to get into Oswald's inner circle. He was the playboy that ran most of the world's technology industry and a fair bit of everything else. We'd been investigating him for years, with me as the man digging deep into everything I could find. Something big was happening in Oswald's world and I'd always felt it was somehow nefarious.

At least that was until yesterday. Oswald had brought me in deep. No doubt he'd probed my agency provided background to make sure I was safe and he let me in on his biggest secret. He had built much of his empire as a vehicle to create a Mars colony. The whole notion was outlandish and yet I believed him, at least for the most part. He had a problem though, his analysts projected that all of his colony plans would fail, and he recruited me to help figure out the cause. As an outside observer, he was hoping I'd see something that his more involved teams had missed.

I still felt like I was missing something, and I knew it was important. I'd played along well so far, and Oswald had warmed up to me. It didn't hurt that he was amazing in bed, and I had been happy to spend the evening under the covers with him. My pussy was still tingling from the way he'd ravished me. Before this assignment, I'd never thought that having sex as a woman would feel so good. Now, it was hard to imagine doing it any other way.

That left me with Oswald's arm draped over me as he breathed deeply behind me. He was still asleep and I enjoyed the warm closeness for a moment. I was used to sleeping alone. It was certainly nicer waking up right next to someone though. My drowsy mind wandered for a bit as I snuggled back against him until I noticed his dick getting hard against my soft bottom.

That sparked an idea. I was all too familiar with waking up aroused in the morning as a guy. There was also a little something that came to mind, a desire usually unfulfilled. The worst part about an idea like that is that once I think of it, I can't stop thinking about it. I squirmed a bit as my pussy started to warm up. Now, there was simply no question about doing it.

Getting into position was not that hard. The trick was getting there without waking him up. First, I had to lift up his arm and slowly slink out from under him. I managed that without him reacting. Then I moved up beside him and gently pushed him onto his back and had to fight down the giggle that came from seeing his cock tenting the covers. It just seemed so absurd to do this, and yet I had to. Now that he was on his back, I slipped back under the covers head first. I was careful to crawl up beside him instead of climbing over him. Finally, I was in place, looking over at his shrouded manhood and feeling a bit giddy at the perverted playfulness of it.

I hovered as I considered what I was doing. I'd sucked on cocks several times over the last couple weeks, but this was different. It had always happened before in the midst of a wild orgy or when I was already deep in the throes of passion. While I was certainly getting a bit turned on, I was far from overcome with lust, and this felt far more significant in that sense. I had been a guy after all, and now I was about to go down on a guy without even the slightest prompting. What surprised me, was how little the notion bothered me, it was almost funny to my newly minted feminine psyche. After all that I'd done, that I'd even get a bit concerned about my masculine identity now was amusing.

He grunted and started to wriggle under the covers and that broke me out of my deliberations. There was simply no more time to waste. I pushed a bit closer and then tipped my head over. My hair cascaded over his stomach as I lined up my mouth with the tip of his morning hard on. I paused to take a deep breath and then dove in, opening my mouth for his hardness as my lips slid around the bulging head. He let out a sudden huff as I took his full length into my mouth and then gave him a nice wet suck.

I slid my tongue along his throbbing shaft and savored the masculine taste. It was so different than the tangy sweetness of a warm pussy, and yet so arousing in the same way. His breaths had become deeper and more ragged as I stroked and licked him with my mouth. I kept the pace slow and steady, I didn't want to wake him up too early. The very notion of it was making my pussy even hotter, and I couldn't resist slipping a hand between my legs so that I could rub my hot folds. It was a bit of gymnastics to manage, holding myself up with one hand while I bobbed my head on his cock and stroked my clit.

Any lingering softness in his manhood was gone now, and I could feel him throbbing hard in my mouth as he started to squirm under me. He was trying to fuck my mouth and I backed off every time he seemed to be getting too excited. I wondered just how much more it would take to wake him up, but I imagined that he must be having the best dream right about now.

"Oh... oh yeah..." He whimpered as I gave him a couple of long sucks. I was just about to go down again, when I felt his hands slide over my thigh and hair. That was enough for me to give him another devotional and dove down until my lips were wrapped around the base of his cock and my tongue was busy sliding up and down his veined shaft.

He started to shift under me, and I knew he was awake. I was ready for the next surprise. I pulled off of his cock and jumped on top of him, straddling him before his fuzzy morning brain could react. I reached down between my legs and quickly guided his throbbing hardness towards my dripping pussy and impaled myself with a swift shift of my hips. Our moans filled the air as I pushed down and his manhood stretched me open again. I reveled in the feeling of fullness as I felt the base of his cock pressing against my tender folds.

"Good morning, sleepy head!" I giggled as I started to bounce on top of him. My hair flew around me as I felt my breasts jiggling with each rise and fall of my hips. I was sitting back on my haunches, so I could nearly sit up straight as I rode him. He was hard enough to make it easy without the risk of him slipping out, and the look of half awake arousal on his face was enough to make it all worth it.

"Oh, fuck..." He gasped as I managed to work a wicked little twist into my downward motion. I could see that he was fighting to keep control as I bucked my hips. It wasn't every morning that a hot little vixen woke you up this way after all. I could almost watch as his neurons started to fire up and catch on with what was happening.

When his hands grabbed onto my thighs again and I felt him starting to thrust into me from below, I knew he'd finally woken up. I squealed as he took control and I was greeted by a series of hard thrusts of his huge cock. The shift was visceral, and I found myself reacting instead of acting as he ravished me from below.

"Yes! Harder... just like that!" I gasped as he pounded into me. It felt so much better like this, firmly in his hands as he claimed my soft flesh. All semblance of my recent command of the situation had melted away and I was putty in his hands. He didn't waste the opportunity either. He was a master and I succumbed to his skills. His pace grew rapid, demanding, and I knew that neither of us would last long as the frantic passion engulfed us.

Then he drove deep and held me there as he exploded inside me. The feeling of his cock shooting off inside me was enough to send me over the edge. I screamed out as my pussy squeezed down. My whole body quaked from the rush of pleasure. Everything was tingling, and I sank down on top of him as I milked his cock dry. His warm flesh felt so good against mine as we savored our mutual orgasms.

We stayed like that, panting and pressed together for a while, savoring the closeness and the sweet afterglow of a little morning fun. We rested, looking into each others eyes and smiling. I may have even giggled a bit. Suddenly, I felt silly, but not in an embarrassed kind of way.

"Thank you, I don't wake up that way often enough." He smiled as he finally started to stir. It was still a work day after all. I managed a quick glance at the clock and saw that we were in luck. There was still plenty of time to get ready. I smiled back at him.

"So how big is your shower?" I asked. He gave me a knowing grin and the sheets were flying through the air a moment later. There was still an odd thrill that came with being walking around stark naked, especially now that I was a girl. Thankfully, we didn't waste much time getting to the show, and his bed was more than big enough to comfortably accommodate two people.

As the water flowed down, I looked up. The moment just hit me. I was staring up at him, at this man who had managed to dominate me so wonderfully. His cock was still hard and it was now rubbing against my stomach, just as my nipples were pushing into him. He was so tall, and I couldn't ignore that when he was so close and I had to pull my head back to look up at him. Everything felt more real than it had since I'd begun this mission. Somehow, I felt like in this instant I understood so much more about being a woman.

The intensity of the feeling took me before I was able to snap back. I was untethered, and my hand reached for the soap. "We should make sure to get nice and clean, we have a long day ahead."

I didn't wait for him to reply before I started to soap him up. He joined me a moment later, starting at my shoulders and working down. I was busy enjoying the feeling of his firm flesh sliding beneath my delicate fingers as his strong hands ran over my softness.

"Have I told you just how much I love your breasts?" He asked as he gave them some loving attention. His fingers caressed them gently in smooth strokes, slowly following the curves as he moved towards the center where my hard nipples poked out at him.

"Not often enough." I blushed. I enjoyed the complements and yet it felt rather embarrassing to be so open about those feelings. I had to say I liked them as well, especially when they were being handled so expertly. There was no real male comparison, to the feeling of a man's hands on your breasts. It wasn't that they were so directly sensitive, but rather the way desirous attention could stoke further passion.

I had worked my way down to his cock and was not about to waste that opportunity as I soaped him up. "And you know I love this big hard cock."

He just laughed and we kept up our work until we were both lathered up, front and back. I'd never explored the male body so thoroughly before. Even when I'd been a guy, it had just been the simple mechanics of survival. Now, I was paying attention with the lustful eyes of a young woman. I never imagined just how sexy it was to trace my fingers along the lines of a muscular back. The firmness and strength were alluring in ways that titillated me.

We made quick work of that lathered soap as we slid our bodies against each other until we were free of the little bubbles, and almost squeaky clean. Still, there was one more need yet unmet, and I gave him a lustful glance and turned around so that I could grab onto a conveniently placed handlebar and leaned down so that I could thrust out my ass and spread my legs.

"There's just one more spot that needs a good scrubbing." I looked over my shoulder and wiggled my ass. He laughed and slid up behind me. I felt him reach for something and then felt his hand slide up my pussy a moment later as he covered me in a some kind of cool gel. I squirmed, surprised at the strange feeling for a moment before I felt his cock slide over my slit and I moaned in anticipation.

"My pleasure." He grunted and I moaned as he slid into me with an easy thrust. I cooed at the luxurious feeling of hard cock stretching me open and warm water flowing all around me. He didn't waste time teasing me. He quickly built up a rhythm that had me panting as I bounced from his firm thrusts.

"Yeah, make sure to get in there nice and deep..." I taunted as he drove in harder. He laughed and grabbed me tight so he could grind his cock in nice and deep. I gasped in thanks and squeezed down on him, hoping to keep him nice and excited.

The playfulness of it quickly dissolved into more base passion. I just let myself enjoy every moment. It was another benefit of being a woman. I didn't have anything like the same kind of performance issues, I didn't have to worry about shooting off early, or not staying hard, I could just ride the feelings and savor the wild pleasure.

Oswald made sure I enjoyed it as well. His thrusts were magnificent, but his wandering hands made their way to my breasts and down to my clit as well, rubbing and stroking and squeezing until I was squealing from the pleasure of it all. By the time he filled me with another load of cum, I was riding a wave of sweet orgasms that I knew would have me glowing all day long.

We rinsed off and finished cleaning up. Thankfully, he had a separate sink for me and I did my best to finish prepping as fast as I could. I didn't want him to see me in my disheveled state for too long. It was one thing when you were in the middle of a wild bit of fucking, but now that we were past that for the moment, I didn't want him to see me as Karen of the wild hair.

As I was finally finished drying up and gotten somewhat primped, I realized I didn't have anything to wear beyond the little black dress I'd worn to dinner last night. Even if I wore that back to the office I only had yesterday's clothes waiting for me.

"Oh, what am I going to wear?" I lamented as I tugged at the towel I'd wrapped around me. Oswald had already left to get dressed himself, but he popped back in when he heard me.

"Don't worry, I've got a little service around here. We can order you up a quick outfit. Just request it from my terminal." He said before jetting off again.

I wandered out and found his terminal already pulled up to the page for ordering clothes. He'd certainly picked out the outfit that was on screen. It wasn't bad either, a very modest skirt and blouse combination with just enough lace to be feminine without being girly. I knew it was a veiled hint, but that I could choose anything else if I wished. I thought about it for a moment and then ordered the clothes he'd picked out. It certainly didn't hurt anything to humor him. I did want him to stay happy after all.

Oswald swung through again as I ordered. He came up behind me and gave me a quick hug and a peck on the cheek. I felt an odd quiver at the casual intimacy of it. I'd never managed much in terms of relationships before, and I found myself struggling with a sudden rush of affection for this man.

"Sorry, but I've got an early meeting across town. I'll have a car waiting for you downstairs when you're ready to go to the office. I'll see you later." He gave me another squeeze and then I gave him a wave as he left.

As the door closed I stood there, collecting my thoughts. It took me a moment to realize that I was really alone in his apartment. That reminded me of why I was here in the first place. I slapped my forehead as I considered my position. The worst part was that I wasn't ready for this. I'd left the office wearing little more than a black dress, my glasses and a pair of shoes. I had even left my purse back in a company locker, not that it would have done me much good.

I had access to his computer systems, but I couldn't exploit it. I might be able to poke around a bit, but there was every chance that I'd trigger an intruder alert, or at least have my actions logged. I needed my agency infiltration tools to get anywhere without being detected, but I didn't have them on hand. I realized that this was just an example of why they didn't like sending amateurs on missions like this.

I consoled myself with the probability that I had just as good of access back at the office. Oswald was meticulous with his data, and after getting direct access of one of his big projects, I knew he took that tidiness much further than I would have guessed otherwise. That meant I was unlikely to find anything here in the first place and even if I did, I could be sure he'd know instantly that I had been into those files. It was better for me to exploit my access back at work where I could more easily mask my activities with plausible deniability.

That helped my conscious, but not for the those reasons. The fact was, I was starting to really like him. I even felt a bit guilty about spying on him, and felt a lot better once I decided not to try anything here. It didn't hurt that my investigation had only turned up a clandestine program that he was trying to hide from his investors, but one that was far from illegal. The trouble was I still had a nagging feeling that I was missing something and that I wouldn't like it when I figured it out.

Thankfully the clothes arrived and I could finally get dressed. I didn't have any need to stick around his place so I headed back to the office. I watched the world zoom past and simply enjoyed the sights of people going about their day. It was warm and sunny this morning and that helped perk up my mood as well. I still had a lot to do.

I didn't waste any time diving back into my research when I got to the office. It wasn't long before I was surfing through a pile of tablets, shifting between data sets and lost to the work of figuring out Oswald's problem. It was an easy distraction from the guilt that was starting to drift into my thoughts. Whatever the reason was, his colonies weren't slated to fail for something superficial, it was going to be something buried deep or else he would have found it by now.

So I dug into the base of the models they were using. It was clear he'd solved so many problems. The dysfunction wasn't related to something as easy as lacking food or water. Even radiation had been accounted for and the habitats had been designed to shield everyone. The more I looked, the less likely it seemed that he was going to have an issue with any of the physical aspects of the colony. That left me with one remaining area to consider.

People, the true linchpin of any operation was the people. It was an easy thing to overlook for me. I had never been particularly good with people. Data and information systems had always been so much easier to understand. Sure, I studied people, but I'd done it by breaking them down into bits of information that I could process. It was only the raw process of elimination that brought me to considering that it might be the people that were causing the colony to fail.