Gender Bending Investigations Pt. 04

That just ruined the look, and I struggled for a moment. I wanted to look hot, but going without panties was another level of risque I wasn't sure I wanted to jump on. I had to admit that the notion was kind of thrilling as well, though. I'd be going out, exposed and open and while some may guess, no one would really know that for certain. If my ultimate goal for the evening was to get him in bed, then it certainly wouldn't hurt that cause either. He might even find it titillating.

So the panties came off as well and joined the stack of clothes I'd built up. I took a moment to primp in the mirror again and straighten out my dress a bit. It felt kind of strange going out wearing only a dress and a pair of dress shoes. I'd certainly never done anything like this when I'd been a guy, and it wouldn't have felt the same way even if I had. Being a woman in a slinky dress was an entirely unique experience.

"I hope I didn't keep you waiting too long." I flashed him a smile when I bounced back to where Oswald was waiting. He turned to look at me and for a moment I could see the surprise and satisfaction on his face when he saw me. His eyes tried to be respectful, but clearly did a full appraisal as slowly as he thought he could get away with. I didn't mind, really, in fact, I felt rather smug from grabbing his attention so well.

"Oh, well, any wait would be worth seeing you like this. You look stunning." He smiled and held out his arm. He looked so strange with his arm hooking out like that and looking at me expectantly. It took a moment to realize what he was offering and I swung around and took his arm. Just another strangeness of being a woman, but it felt good to snuggle up against his side while we waited for the elevator.

"Thank you." I blushed a bit from his compliment. It seemed like men liked to throw a lot of flattery at lovely women. I'd never realized how much, and it still made me feel kind of weird when I was the target.

"I'm glad to see that you've thrown yourself at the project. I already heard back from several departments about your inquiries and they were all impressed. I knew I chose the right woman for the job." He smiled as rode the elevator.

"I'm just amazed to be involved with this at all." I beamed. It had been a crazy day and even for the short time I'd worked on the project, I was almost overwhelmed by the depth and complexity of it. There was no doubt that he was serious about making a colony work. "I just hope I'm not the only one doing this kind of review."

"Naturally. But I felt it would be better at this stage to keep you all separate."

"So we don't contaminate each other." I nodded. It made sense. He was trying to keep as many fresh eyes on the project. He didn't want us to infect each other with our own notions of what was happening. The best plan was to keep everything isolated, at least for now.

"Exactly. But enough about business. I know you'll be chewing on that all night, but I was hoping to get to know you a bit better." He gave me a warm glance. As intimate as we'd already been, we still didn't know each other on a personal level. I had to admit, even after years of studying him as an analyst in the Agency, I knew very little about him personally.

"So long as it's mutual." I gave him an impish grin.

"I wouldn't have it any other way." He stepped out when the elevator opened. There was a cab waiting for us and it set off as soon as we'd stepped inside.

"So where are we going?" I asked as I settled into my seat.

"Just a little place I own." He sat smugly for a moment. Then he laughed. "Ok, no humility here, it's Tops, over on second."

"Wow." I let my jaw drop a little. I knew how far his empire extended, but there was still something special about going to the fanciest restaurant in town. It also occupied the top two floors of one of the tallest buildings in town. The wait list for an evening there was almost three months. For new years eve it was up to five years now. I'd never even considered going there. It really wasn't my style, but for Karen Borden, it was something she should be excited about.

"I don't usually like half measures. If I want a nice meal, we go to the best place in town. I hope you don't mind." He relaxed as the buildings flew by. It still surprised me how fast cabs could go around town now that everything was self driving. There were just a few dedicated streets that allowed generic traffic, but the traffic control systems allowed us to speed across town at almost a hundred miles an hour.

"How could I?' I laughed. Turn down a date at the fanciest place in town, with the richest man in the world? For a single young woman, there was almost no question about objecting, even if all you took away was bragging rights.

"Well, then we're here." The door popped open and we made our way out. Tops had its own elevator complete with a red carpet entrance, a doorman and maitre d. Oswald did all the talking and I did all the gawking. The place was swanky in a way that defied my vocabulary. I had no words for it. I just followed along, feeling oddly like a lost puppy.

Almost everyone was dressed to kill, and nearly every table was filled with local celebrities and people of influence from all walks of life. The waiters and waitresses were dressed in impeccable black suits and dresses. A live band provided the ambiance, though they kept to classical choices and at a volume that didn't challenge conversation. The mood was entirely calm, and refined.

The dining room was enormous, filling almost the entire top floor of the building. Only a couple of elevators and a small hub for the staff sat at the center of the room. The floor was broken up into sections, some raised and some lowered to give each area a more intimate feeling. Lower sections were ringed with booths with tables filling the central areas while the raised section were only filled with tables.

As Oswald navigated through the room, I noticed that there wasn't an empty table to be found. A couple were being cleared in a frantically graceful manner by the staff, and I guessed they wouldn't be vacant for more than a few moments. We headed up to one of the raised sections that overlooked the center of the city and the waterfront. There was a clear table here, right against the glass, with a small division of plants, offering a bit of privacy from the other tables.

"There are some perks to being the owner." He smiled as he pulled out a chair. I stood there wondering just what he was doing and why he wasn't sitting down. Then it hit me and I blushed a bit, embarrassed to have forgotten my role for a moment.

"Thank you." I flashed a smile at him as I sat down and let him help push my chair in. Naturally, as a guy the whole exercise felt a bit strange, but as a girl, I rather appreciated the gesture.

"So you really own this?" I looked around. The notion would be crazy if it was anyone but Oswald.

"Why not? They've got a great chef, excellent staff and the view can't be beat." He waved his hand out towards the sparkling lights of the city. It was like a sea of stars down there, twinkling as millions of people went about their business. The movement of the streets was like raceways with the cars zipping along the main streets and slower streams on the side streets.

"Honestly, though, I'm still not used to having the kind of money I do. Buying a restaurant on a whim feels as crazy as it sounds. Still, I didn't do it all for fun, I've got their kitchen staff helping to design the foods for my auto-chef units for the initial stages of the project." Oswald winked at me. I laughed a bit. He had a way of tying all of his projects together. He needed help with the food for his initial colony team, before they'd be raising crops on Mars. So he picked out his favorite restaurant and bought it. In one stroke he gets to look like the dashing playboy and gets another piece for his bigger goal.

A waiter swung by and handed us the menus and went over the specials. For an Agency analyst, the menu was almost like a foreign language. I rarely ate at any place that was more than fast food, and certainly not somewhere that the name of the chef was a serious selling point.

"See anything you like?" Oswald asked as I pondered just what kind of meat came in half the dishes. I wasn't even sure if there was meat on the menu.

I gave him a distressed look and he nodded.

"Well then, I'd recommend the Verici Riodani. It's amazing. I'm not sure what it is, but I'm guessing it started out as a fish sometime before it got here." He put down his menu. "I may own the place, but I'm not in charge of the menu. People seem to like the flair of exotic names, so who am I to argue?"

The conversation drifted from there. Food and drinks came by and I indulged in a bit of wine while I enjoyed the succulent dishes that appeared in front of me. Oswald was still every bit the mismatched character. He was far from the arrogant rouge capitalist of his media persona. His modest beginnings had been played as part of his rags to riches story, but I could see that he hadn't really left them behind. We swapped stories about how it was growing up smart in a small town. In the end, I found his company far more enjoyable than I would have ever guessed after having watched his public persona for so long.

As we finished up our dessert, I felt a new mood starting to build between us. He was playing it casual, but there was little doubt where the subject was going to go next.

"So, can I pick a place?" He sipped on his drink as I ate the last of my cake.

"Oh, yes, that was amazing. Thank you." I said. I'd never eaten so well. That he was treating me only made it that much more enjoyable. I didn't even want to think about what the bill must have been. The menu had been devoid of prices.

"My pleasure." He sat back. "So, I've had a pretty good time and I was just wondering..."

"If I wouldn't mind going for coffee, at your place, maybe?" I finished his awkward sentence for him. I was getting used to the fact that he wasn't the suave operator he pretended to be sometimes. He liked things direct and clear. I felt an affinity to that, it was something in the way that software and data people thought. Of course that need for clarity only hurt at awkward moments like this.

This time I got a chance to see him redden a bit. He squared his shoulders a bit and gave me a big smile. "Something like that."

"Sure." I gave him my best lascivious grin. I was really beginning to enjoy playing the impish vixen. I'd never felt so playful as a man, but as a woman it just seemed to come naturally to me, especially with my rather elfish figure. I knew he didn't mind either.

"Shall we?" He stood up and offered me his arm again. It wasn't like he had to wait for his bill. He did own the place. I slid onto his arm and pulled up tight. If I was anywhere but here, I might have ended up on the front page of the news, but this was not the kind of place to allow paparazzi.

His car was waiting, and it wasn't long before we were zipping across the city again. His apartment wasn't far. He preferred living close to work, and while he did own several larger homes around the country, he rarely seemed to really live anywhere other than the apartment he had here.

"I never could abide by those huge mansions." He explained as he walked me into his place. It was still a large suite, with a nice open kitchen and spacious living room. Still, it was a stark contrast from the raw wealth available to him. "They're always so big and empty feeling. You know."

"It's nice to have the option though." I smiled. I'd never been able to afford much more than a single bedroom place, and it was far more compact than this.

"I suppose so. I just keep the big places to entertain. When you're one of the richest men in the world, there are certain expectations when you throw a party." He went into the kitchen and came out with a couple of drinks. "It's not coffee, but I hope you enjoy it."

I took a sip. I rarely drank much, but it was smooth and I knew it was going to go right to my head. I had learned that I didn't have much of a tolerance for alcohol in my new body. It wasn't that such a feature couldn't be added, it's just that it was such an obvious alteration that it would be instantly noticed in a medical exam. All it meant now was that I had to be careful to nurse my drinks.

"Very nice." I smiled as we moved over to the couch with the best view of the city. As we settled in, he waved his hand and the lights dimmed to that perfect level where you could still see, but everything felt more cozy.

"I'm glad you like it. Apparently, I bought the winery that made it last week. I got a couple of cases sent up from my finance guys." He laughed.

"I can't imagine what it's like to have so much money that you don't even know that you bought a winery." I giggled and snuggled in closer. For Karen, it would be something of a turn on or at least exciting that she was going to be hopping into bed with someone so rich and so smart. It didn't hurt that he wasn't bad looking at all. Of course, we'd rather gotten past the first impression stages of a relationship, and I had to admit I was looking forward to what was about to happen next.

"I'm not sure I really feel it either. It's just something that kind of happened. Throw in the work done to support the plan and sometimes I don't know what half my companies are doing. Sometimes it's almost too much just to keep up with what I'm doing." He draped his arm around me. His hand slid down my side, but he kept himself tame. We were both warming up, but were taking the time to savor the moment.

"Well, I hope you're paying full attention now." I rubbed his thigh softly. It didn't take much for two people who liked each other to get excited. I could even feel him start to squirm a bit. My ardor was rising as well. I was still getting used to the warm squishiness that grew between my legs when I got horny. The sensation was so strange, but it also heralded so much pleasure to come.

"There is nothing else on my mind." He pulled me in and gave me a hearty squeeze. I melted into him, then pushed up so I could give him a quick kiss. This was the perfect way to end a day like this. I had to admit that I was growing torn. The seduction had been a gambit at first, a simple way to get close to him, but I was beginning to really like him. I remembered my briefings and prep work, but I was starting to feel like there was something wrong with our assessments.

That flash of concern was quickly dismissed when he slid a hand around and cupped my breast. I squirmed at the intimate caress. His hand was tender, and he massaged my softness gently until I started to coo. He might have his awkward moments, but he always knew how to treat a woman when the mood turned steamy.

I relaxed and let him take charge. Maybe it was something to do with his confidence, but it was clear he liked to lead the way in bed. Almost as strangely, I enjoyed it as well. I'd never really considered the submissive role as a guy, or how hot it was to be dominated. There was a freedom that came with being told what to do. I didn't have to worry about my choices, all I had to do was enjoy the sensations of being ravished.

Oswald's touch was quickly exciting me. He started to rub his hand up my thigh, higher and higher, until he gave me a knowing smile. I blushed a bit, knowing that he'd found that I wasn't wearing any panties, and he slid his hand over my bare ass. I felt rather naughty at that moment. I'd skipped them for rather practical reasons, but I knew it was partly to entice him at this moment as well.

He didn't say a word. His other hand simply moved under my dress as well, and then in one wild fluid motion, he had the whole thing up over my head and floating over the back of the couch and I was completely naked. I felt a sudden chill, but it wasn't enough to cool the heat growing between my legs.

He started to take off his shirt, and I didn't hesitate to go after his pants. I'd gotten good at unbuckling a man's belt from the other side, and quickly had him stripped bare as well. His cock throbbed eagerly between us as I pulled off his pants and underwear while he tossed away his shirt. I had to admit I'd come to appreciate the sight of a man all hard and ready to pounce.

For a moment we sat there, each breathing deeply and gazing at each other. It was a visceral pause, I could feel my pussy quivering, eager to feel his throbbing hardness press into me. My whole body was tense with anticipation. I could barely wait for what was about to happen, and he let me linger on that fine edge long enough for me to almost growl with need.

Then he made his move. He grabbed me again, wrapping his hands around my waist and then he threw me over his shoulder. I squealed in surprise as he stood up and carried me to his bedroom. I thrashed a bit, pretending to be the outraged woman I felt I should be, but in truth I found the whole notion wickedly arousing.

"Let me down you brute!" I shouted while doing my best to keep from laughing. Somehow it felt ridiculous being handled like this. I hammer at his back with my fists, but nothing loosened his grip as he stopped in front of his bed.

"Wah!" I squealed again as he lifted me off his shoulder and tossed me onto his bed. I landed on my back, my hair exploding around me. It felt so wild to be handled like some kind of toy, but I tried to regain some bit of dignity before he jumped onto the bed and pulled open my legs.

His lips curved up lasciviously as his eyes sparkled with untamed passion. I only got a glimpse as he pounced upon me, pressing his hard naked flesh against my soft curves. I braced myself when I felt his manhood probing between my legs and then cried out when he seized my waist and thrust deep inside me with one hard push of his hips.

"Oh, god!" I screamed as his cock drilled into me. I was suddenly full of cock, and he began thrusting into me with a hammering fury that shook his bed. His forceful rhythm had my whole body bouncing, especially my breasts. The savage pounding drove out every other thought, and I opened my legs wider for him and tried to meet his thrusts as his hands began to work their way over my body.

His touch was as demanding as his pace. He squeezed and stroked up to my breasts and then he took them both in his hands and molded my tender orbs with delight. His fingers sank deep into my softness, my nipples were pinched and twisted and all the while a mixture of pleasure and pain had me reeling beneath him. Even when it hurt, it felt so good, I couldn't even articulate my pleasure any longer. All I could do was gasp and moan in unrestrained ecstasy as he ravaged me.

With his cock plunging into my pussy and his hands squeezing my breasts, he pressed down and kissed me. His lips were forceful, demanding, and his tongue dove into my mouth. I was consumed by this final act, my whole consciousness descending into nothing more than a world of savage sensations and raw lust.

We melted together like that, thrusting and writhing, moaning and gasping. It was intense, and I was fully at his mercy. It felt amazing, purely animalistic in a way that I could not deny. I just let myself go completely. My feminine instincts took over, stroking and squeezing him as I wrapped my arms around him.

The power of our shared embrace quickly overwhelmed us. It was all I could do to hold myself together, and every motion only intensified the loss of control. My lust was all that drove me as our flesh became one. I was gasping and moaning as his grunts rose to a crescendo of passion. He squeezed my breasts tighter, forcing me to cry out as his hips slammed harder between my legs.

Then he dove in for another demanding kiss and just as my lips met his, he gave me one last hard thrust. My body quaked as he ground into the depths of my pussy, and I could feel his cock pulsing inside me. Pleasure exploded inside me as my orgasm followed his release. My pussy clamped down on him while he filled me with his seed. My whole body shook as warmth spread through me.