Gender Bending Investigations - Cover

Gender Bending Investigations

Copyright© 2021 by Farleven

Chapter 3

Erotica Sex Story: Chapter 3 - I'd been investigating Patrick Oswald for years, trying to find out what was at the core of his success. After other agents disappeared, they decided to send me in undercover to use my special knowledge of his case to find out what was happening. Now I was going to become a woman and seduce him to get access to his personal records. I wasn't prepared for what came next.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   BiSexual   Heterosexual   TransGender   Fiction   Crime   Workplace   Science Fiction   Transformation  

“Well, it certainly sounds like you had fun last night.” The android gave me an awkward smile. It didn’t quite mimic Agent Raikins expressions right, but I knew him well enough to know what he was trying to do. I wasn’t used to working with his robotic stand in yet, even if I knew that Raikins was puppeteering the android from a virtual reality suite back at the Agency.

I blushed a bit at that. Naturally, I had to tell my handler why I’d been out all last night. I was rather embarrassed to tell him that my co-workers had taken me out for a full on orgy to welcome me to the team. Thankfully, he didn’t ask for too many details, since I wasn’t sure I would have been comfortable sharing.

“Yeah, it was kind of amazing.” I squirmed in my seat just thinking about it. At least I was at home where I could allow myself to just embrace the discomfort. The truth was, the whole experience had really rattled me in a way that even rolling around in bed with Raikins hadn’t done.

I was a woman now, and certainly after last night, I’d pretty much been taken on an explicit tour of my full femininity. The deep cover mental conditioning that had been done when they’d turned me from a middle aged guy into an early twenties girl had held through everything. I had ached in ways I’d never imagined and begged for more again and again. I couldn’t even tell you how many men had filled my mouth or my pussy with cum. I’d been ravished for hours, wonderful endless orgasm filled hours.

I didn’t really want to think about it too much, or what the whole experience implied about me. No matter how real it had felt, this was all artificial. I wasn’t really a woman, it was just a way to get into this organization and work my way into the company of one of the world’s most powerful men.

“I’m glad, and it sounds like your cover held very well. So, for the rest of this week, I want you to keep cozying up to the new team you’re on, especially your team lead.” Raikins kept up with business. He was my handler for this mission after all.

“Phillip? Why?” I asked. I headed over to the fridge and grabbed a glass of orange juice. I noticed that I didn’t get nearly as hungry in my newly petite form, but I still liked a little something in the morning.

“Our sources say that he has connections that go further up into management. If you can get on friendly terms with him, he will hopefully help get your name circulating up with the department heads. You’ve already done well when you fixed their little software issue yesterday. If the department heads are talking about you when the party comes around, Oswald is almost certain to give you some personal time.” Raikins explained. It made sense. I’d already made a big splash when I helped them on my first day. If I could get more energy moving around me, that could only help.

“Sure. He’s nice enough.” I nodded and sipped at my juice.

“Just be sure not to lead him on. Keep it casual. The last thing we want is for him to get territorial about you. It can be complicated being a woman.” Raikins gave me another artificial grin. I couldn’t forget that he’d been a woman on an undercover assignment as well. He’d made it through all the weirdness, and that helped give me a lot of confidence.

“Relationships.” I laughed. I’d honestly not had much luck with them. As a hapless guy I rarely even dated, and the nature of my work helped to sabotage what girlfriends I’d managed to get. Now, my goals relied upon striking up at least a somewhat serious connection with Oswald. The whole idea seemed crazy, but I had to do it.

“Right, be careful. It’s easy to get things going too fast. At least there shouldn’t be much damage that you can do in a couple of days. Still, try to get in good with your coworkers. We want them to be happy to introduce you around.” Raikins pushed and I simply agreed. It was going to be a crazy few days, but if I was lucky it would position me right where I needed to be.

Raikins left me to get ready the rest of the way for work. The whole process certainly took longer now. All I used to do was take a quick shower and toss on some clothes. Now, I had to primp my hair and put on makeup. It still felt weird looking at a cute brunette in the mirror and knowing that it was really how people saw me now. Still, I wanted to look good, and I took the time to do it all right.

I did dress down a bit today. It was clear that this office wasn’t very much for formality, so I went with a simple T-shirt and slacks combo. I laughed a bit when I looked in the mirror. Even in something that should be so plain, I still looked stunning. I knew it was a woman thing, the cute ones could stun you no matter what they wore, and it seemed like I fell into that category.

The morning was uneventful. Jack, Susan and I dove back into the data system I had helped with yesterday. Because of my brilliant idea, we now had to rewrite a rather large amount of our test code. It wasn’t thrilling work, and was very detail oriented. In the end, we mostly sat around my desk and they helped me through the process of learning their system as we updated the code.

“So how is my newest little team doing?” Phillip asked as we all huddled over my desk. We were so focused that his interruption came as something of a shock. We all turned to look at him and he laughed at our rather blank expressions.

It was Susan who recovered first. “Just hammering through the rewrites, boss.”

“Wonderful, but it’s about time for lunch. You don’t mind if I grab Karen, do you?” He asked.

“No, we could all use a break. So, be back here in an hour?” Jack asked. We all nodded and I soon found myself with Phillip on the way to the cafeteria.

“You haven’t tried out the in-house chefs yet, have you?” Phillip smiled.

“No, I guess not.” I followed him. It felt a lot more like we were walking into a restaurant, then any employee cafeteria I’d ever seen. About the only thing it had in common was that you had to line up for your food. The rest of the room was filled with very nice tables or booths that could sit from two to ten people. There was even an upper level that gave you a good look at the city. It was pretty much all the way classy. The tables and chairs were solid wood, well carved and polished. The room was filled with plants, sculptures and paintings that all added to the atmosphere.

“Then you’re in luck. We may go out sometimes, but the quality of the food here is top notch, and all complimentary as well.” Philip picked up a tray. The smell was certainly enticing. It was a wild combination, the kind of thing that only a place like this could generate, but the pure quality of the scents all complimented each other. The strongest sense was from the stir fry currently flipping into the air as the chef worked it in his wok. The tantalizing smell of steaks on a hickory grill teased at my nose. By the time we’d made it up to where they took orders, I was fighting off the urge to drool.

The menu wasn’t as extensive as I would have expected, but it was nice to see a very nice variety. There was basically an option for every taste and diet, but generally only one. I was torn, there were simply too many choices. Phillip ordered the chicken stir fry while I debated my choices. Finally, I knew I had to make my decision.

“I’ll go with the steak and potatoes. Medium rare.” I ordered and followed on after Phillip. We grabbed drinks and swiped our badges and walked into the seating area.

“They’ll have the food out in a few minutes. Why don’t we sit upstairs?” Phillip escorted me to a small table with a view of the city. We were just early enough to have missed the busiest point of the lunch rush, and I saw people starting to scramble in behind us.

“Nice view.” I took a look out. The city was bustling along. We were high enough here to get a view past, most of the rather staid business district and could see all the way down to the water.

“So, how do you like it here so far.” Phillip asked. I quickly realized just why he’d taken me aside. I was a new employee after all. It was important to judge just how I was handling the new job. It was only my second day, but I knew how important it was to get people off on the right foot.

“Oh, it’s been great. Jack and Susan are really helpful, and everyone is so friendly.” I gave him a warm smile. It helped that it was all true. If I had been looking for a new job, I would have been very happy to be here.

“I’m glad to hear it. I’m sorry I couldn’t make it out last night with everyone.” He added with perfect nonchalance. My heart skipped a beat. I guess it was a pretty casual thing. Still, it wasn’t quite what I was used to talking about with my boss.

“That’s okay, everyone else did a good job of filling in for you.” I blushed a bit. Then I giggled when I realized what I’d just said. Before I could stop myself, the giggle turned into the maniacal laughs of a mad man, or well woman. The absurdity of everything had just overflowed.

Phillip gave me a slightly worried smile as I regained control of myself. “Sorry, I just ... well, I’m not used to that kind of attention, even if it was kind of fun.”

“Oh, I understand. I guess it’s an adjustment for you, coming from the Midwest and all.”

“Yeah, but to be honest, I was always a bit curious.” I tossed him a wicked look. Somehow it seemed the right tact to take. I was certainly not going to pass for a chaste small town girl at this point. Playing the naive but eager type seemed a much better angle. It was certainly a more friendly way to go.

“Glad to hear it. I know some people have a way of coming on strong, and the baths are a rather intense place.” I could see the worry drain out of his eyes. I could understand how fine of a line he was walking. The very fact that people were more open about their sexuality meant that you had to be careful not to go over the line.

“Yeah, it sure was.” I felt myself growing a bit wet just thinking about it. The endless pleasure of that little orgy had been rather unreal. Now it almost felt dream like, especially while I was sitting here about to enjoy my meal.

Thankfully, a server came by and dropped off our food. The very notion of having a waitress here seemed crazy. They really did care about treating their employees well.

Our conversation drifted back to work. Phillip’s team was always busy. Even if my assistance yesterday helped put them ahead for their current project, all that really meant was that the next round of tasks got started sooner. I tried to fill in the right mix of knowledge with naivete in my questions. It wasn’t always easy, since I knew I lot of things that someone recently out of college wouldn’t know I had to constantly filter myself.

The food was amazing, and that helped. Every time I felt like I was about to take the conversation in the wrong direction, I’d take another bite of my steak. It was delicious and perfectly cooked, that hard found ideal where steak sauce was unnecessary. It was so good that I had a hard time not just focusing on my meal, but as we drifted away from talking about work I had another opportunity.

“So, I heard that there’s going to be a big party this week, at the company.” I prompted.

“Yeah, we like to have a regular thing to help welcome our new employees and help them mingle outside of their own departments. It’s a pretty big deal. You are invited of course.” He said between bites.

“So, it’s just like a networking thing?” I tried to sound a bit disinterested. After all, that wasn’t the kind of party that twenty-somethings got excited about. Networking might be important, but rarely was it much fun.

“Of course, you can do that, but the entertainment is always top notch, as is the open bar. We don’t do things half way around here. And, if that wasn’t enough for you, Patrick usually shows up.” Phillip smiled as he dropped that name. I perked up accordingly, no one in tech would skip the chance to meet the man behind the largest tech empire in history. Of course, my reasons were a bit more nefarious, but I was no less pleased to hear that our sources had been right.

“Really? That’s cool, but it’s not like I’d get to meet him or anything.” I wasn’t sure if I was really pulling off the act right, but hopefully that puppy dog look of disappointment would have its effect on Phillip.

“Oh, well, he usually mingles with everyone, but I can pull a few strings and make sure you get a chance to talk with him.” Phillip reassured me. I let the cloud of worry lift and then smiled up at him.

“Really? That would be amazing! I’ve so wanted to meet him.” I did my best to act like the eager young woman I was supposed to be. Karen was going to meet her hero, that was certainly a cause for excitement. I did, however, want to help seal the deal. We were about to finish our meal, and we still had some time before everyone else would be back from work.

“Sure, no problem. I hadn’t realized you had such an interest in him.” Phillip nodded. A server came by to take away our plates and we got up to leave.

“Are you kidding?” I giggled. “How could I not want to meet the man who almost single handedly runs the tech economy?”

He laughed at that. I knew I wasn’t the first to be a fan of Oswald. After all, his technology ran the world. He was rich and powerful, and somehow managed to avoid the arrogant flair that earlier generations of tech titans had all exuded. If it wasn’t for my rather intimate knowledge of his companies, I would probably have been a fan as well.

This did give me another chance though. Phillip did seem to have the connections we hoped, and that meant that I could get his help to get close to Oswald. I wasn’t going to let that chance slip away. So as we left the cafeteria, I slid up close to him and got onto the tips of my toes so I could whisper into his ear.

“I really appreciate offering to help me meet him, Phillip. I’m also kind of sorry you couldn’t join us last night. We’ve got a little time now, if you want to see what you missed.”

He turned and shot me a look of surprise that quickly started to melt to eagerness as he saw the wanton grin that had grown on my face. Honestly, our earlier discussion about last night had kind of turned me on, and this was an excellent way to kill two birds with one stone.

We didn’t need to say anything else. The break room wasn’t too far away and we were lucky enough to find one of the rooms empty for us. I still had a hard time believing that a company had rooms set aside for office flings like this, but I was more than happy to indulge. As I closed the door, I giggled a bit at the lock. It actually had three settings, empty, occupied and please join in. My mind boggled for a moment and then I set it to occupied. Maybe I’d try the third option some day, but that wasn’t going to be today.

I felt a bit wild. I wasn’t just along for the ride here, I was pushing for it. I was at work, or what was supposed to be work, about to have sex with my supervisor. A million sexual harassment videos must have been crying out in horror, but I was here willingly and so was he. The new world was a strange place, but one I was happy to dive into.

I turned back around and before he could do or say anything else, I reached up around his neck and pulled him down for a nice wet kiss. He flailed for a moment and then his hands slid around me and pulled me tight. My whole body ground against his. My super charged libido hadn’t mellowed a bit, and I felt that depraved need welling up inside me. I don’t think I’d ever been so aggressively sexual as I was now. It all just felt so good, and as a woman, even in this very libertine culture, it was a lot easier to get sex. Men still had to be cautious not to push when they weren’t welcome, but for a woman finding an eager male was pretty much as easy as finding an unmarried guy.

We didn’t waste any time being shy. As our tongues started to dance in my mouth, our hands went to work on our clothes. Shirts, blouses and pants were quickly unbuttoned, pulled open and taken off. We had to pause a few times to pull off an undershirt or in my case a T-shirt. Our underwear followed quickly thereafter, until he was naked and I was down to my glasses and a pair of striped socks.

My body pressed into his as we kept kissing. I quivered as my naked flesh pressed into his. There was a bit of a chill in the air, just enough to make me eager to share his warmth. He was fit and I enjoyed the feeling of my soft breasts pressing into his firm body. It was a strange feeling to be so malleable against something so hard. It was another aspect of being a girl that I found wantonly intoxicating. I’d always enjoyed the softness of a woman, but I’d never imagined the tantalizing feeling that came with enjoying the hardness of a man.

Philip broke away, just for a moment, and he looked down at me. My chest heaved from my ragged breaths as lust flamed in my eyes. I needed to be taken, to be ravished. The memories of last night were taunting me, mocking me with the remembrance of pleasure. I couldn’t deny the power that held over me, the raw demands that lust had driven into my flesh.

“You are stunning.” He gasped as he took in the full sight of my lust wracked body. His eyes traced every soft curve before they came back to meet mine. I remembered how I’d felt when we’d met yesterday, that attraction that seemed to spark between us. Now, it had grown to bolts of lightning crashing into me. His compliment only made it stronger. Even if I knew intellectually that this was not really me, not my real body, that made no difference to the lustful need that was overwhelming me.

Then, before I could react, he reached down and picked me up by my thighs. I wrapped myself around him so that I could hold on as he swung around towards the small bed that had been placed in the room. It was just big enough for its job, and I found my ass bouncing on top of it a moment later. I sat on the edge, with him standing in front of me. Most of all, his cock was hovering right between my legs, all hard and poised to strike.

“Take me...” I ordered him with as husky of a tone as my girlish voice could make. I spread my legs wide for him, exposing myself completely. I felt a bit crazed, the throbbing ache between my legs was driving me wild. I wasn’t sure how long I could keep any semblance of control, and that’s when I felt him rubbing against me.

I gasped from the pleasure of his hardness running over my slit, parting my tender folds and teasing my sensitive clit. The nuances of sex from the woman’s side had a way of tearing through my defenses. It all felt so good, and so wickedly strange. I couldn’t get enough of it. The strangest part was the feeling of submission, it was the man who took charge, who filled my flesh and drove me to my peak. I had influence to be sure, but where he could force himself upon me, I could only beg for him to take me.

Now, I didn’t need to beg. He was as hard as I was wet and his cock was soon coated with my juices. Neither of us wanted to take this slow. I pulled my legs wide and gripped my thighs to keep them open as I struggled to keep control as his hardness teased me. I moaned and gasped as he rubbed and slid between my legs, preparing me, drawing me towards a cliff of raw desire. Then just as I couldn’t take any more, I felt him slide down and press against my wet gates.

“Oh yes!” I cried out as he thrust. My tender pussy opened for him, parting as he pushed deep. I reveled in the sensation, that perfectly feminine feeling of impalement. He was inside me, deep inside me, throbbing and hard. It was depraved, a raw pleasure that cut through everything. At this moment, there was nothing I wouldn’t have done to feel this way.

His hands started to slide over seething flesh. First, he stroked my thighs and teased my hands until I let go and then wrapped my legs around him. He moved higher now, over my soft belly and then up to my round breasts. As he rested inside me, his hands caressed my chest, squeezing and molding my flesh until I was a little more than a melted pool of pleasure.

As I writhed beneath him, he finally took mercy on me, and began to thrust. He was slow at first, drawing back and leaving me to quake and howl from the joy of feeling my tender passage split open again and again. He let me savor each moment as he slowly built his rhythm. I was completely open to him, and he continued to drive me wild.

“Please ... harder!” I begged as he worked. It felt so good, but I’d gone from enjoying the simple wonder of being stuffed with cock. Now, I needed more, I needed to be pounded, to be fucked and fucked hard.

Phillip grunted as I squeezed down on him with my pussy. It made him feel so much bigger inside me, and I could see how much he enjoyed feeling my tightness as well. He started to lose control and I braced myself for it. His thrusts grew stronger and his rhythm more fierce. I shook each time he drove deep. I grabbed at the edge of the bed, in part to hold me in place, but also as an outlet for the tension building inside me. I needed it, needed it so much.

“Yes! Harder! Make me cum! Oh yes!” I wailed. I feared that I sounded like some cheap porno actress, but at the moment I couldn’t think of anything else to say, or any other way to say it. I needed him to ravish me, to push me over the top. It was almost too much, but I couldn’t let go. I had to have more.

He was panting now from the force of his assault. He was tense as well, his hands sinking deep into my flesh as he grew even more frantic. I cried out, thrashing from the needs wracking my body. The sounds of our passion echoed around us, and I seethed, the force inside me was tearing apart and when I finally couldn’t take any more I felt him ramming deep into my depths and we cried out together.

As his cock exploded, I felt my body rush with raw pleasure. The power of it left me gasping. My pussy milked him dry as my orgasm coursed through me, hammering through my flesh. I still couldn’t believe that sex as a woman could feel so good, and I simply savored the warm glow that came over me.

“Thanks.” I panted and stroked his hand as he braced himself against the bed. I could see that he had to recover as well. He smiled down at me, no doubt appreciating the gentle swells of my chest as I enjoyed the moment.

“No, that was amazing, you were amazing.” He stammered. I know it must have hit him hard and I was glad. I knew just how much a good fucking could take out of a guy, it was just kind of funny seeing it from the other side.

“Well, maybe next time you won’t skip a little evening outing.” I laughed. I felt him slowly slide out and I was left empty but satisfied. I wished I had some time to cuddle, but the truth was that we were probably well overdue for getting back to work. I hated to admit that we couldn’t just hang out in here forever.

“There’s a shower in the back. If you want to go first.” He motioned towards a door next to the bed. I slowly got up and considered my options for a moment.

“Well, you could join me, it would be faster.” I tugged at him at the same moment I slid the door open. Before he had a chance to object I’d pulled us into the shower and let him take that first blast of cold water.

“Ah! You just wanted me to take the hit!” He laughed and shivered in unison. Thankfully, the hot water started a moment later and he warmed right back up.

“What? You thought I wanted to get frisky?” I giggled. I filled my hands with body wash and started to soap him up. I ran my fingers all over his hard body, teasing and taunting as I cleaned. The woman in me was enthralled at having such a sculpted man to work over. Still, it was strange to slide my hands over another guy’s body when I wasn’t overwhelmed with lust. In some ways the two sexes really weren’t so different.

Just as I thought that, he started in on me by soaping up my breasts, naturally. I gasped as he scooped, squeezed and soaped them both up. He kept working from there, covering every bit of my body, front and back, with a little extra attention between the legs. There was certainly something electric about washing up like this, but we both knew better than to linger. If we wanted to have more fun later, there would be plenty of time to do so.

We splashed through a quick rinse and then he hopped out while I gave my hair a quick wash. Thankfully, I kept my hair style simple to hard to work with, but long hair did take longer to clean. By the time I was out of the shower, he was already dressed, but he lingered long enough to give me a quick kiss on the cheek.

“Don’t take too long. Susan isn’t the patient type.” He smiled as he worked the door. “And thanks again, for a wonderful time. If you’re ever interested again, you know where to find me.”

“Right back at you.” I winked. I certainly wouldn’t turn him away. Even if I was doing this to help improve my chances of a personal meeting with Oswald, Phillip knew just how to make a woman squeal. I would be more than happy to get another round with him.

He gave me a wave and was off. I quickly dressed and primped myself before heading out. I had been worried about having to miss out on sex when I finally got into the field and under cover. I almost laughed at myself now, I’d had more sex since I started the assignment than when I’d been in training. It didn’t look like I’d have to work hard for more either. I hated to admit that I was almost starting to dread the coming party since I’d have to give up all the fun I was having here if I completed my mission.

Still, there was work to do, and a lot more preparation to be done so that Oswald wouldn’t be able to get out of meeting the up and coming developer that was rocking his data department. I was going to have a busy week.


“You look stunning.” The android gave me its best impression of a smile as I did a little twirl to show off my outfit. After a crazy week of sex and software, we’d finally reached the company welcome party for new employees.

I flushed at the compliment. Even as I was getting fully used to being a woman, getting compliments on my looks still filled me with an odd mix of angst and pride. I tried not to let it show, especially since I agreed with him. I’d managed to find just the right dress with a little help from Linda. It hugged my curves, but left just the right amount to the imagination. The skirt slid past my knees, but the neckline plunged far enough to show off my cleavage. It was a cool baby blue, just nice enough to be almost formal, but still something you could almost go out for a night on the town. All in all, it showed off my little body perfectly, and matched well against the clothes that Oswald’s love interests usually wore.

“Thanks. Is there anything else I should know?” I had spent as much of my free time as I could reviewing Oswald’s personal tastes. I almost felt like a stalker for a moment, even if it was my job. I’d never really felt that way before in an investigation, but then I normally wasn’t researching what kind of wine a man liked after dinner, either.

“We’ve been watching him as best we could this week, but he’s mostly been off the radar. We’re pretty sure he hasn’t found a new woman, thankfully, but keep yourself prepared. If he does have a date, don’t go fishing deep, just try and establish a professional relationship so you can get another chance later. From what I’ve heard, you’ve been making a few waves with your work so you may get another bite at the apple.” Raikins explained. There was always risk in this kind of operation. We didn’t have a lot of time to spare, but it was better not to risk burning bridges.

“I’ll keep that in mind.” I took one more stop by the mirror. “I guess I should be going then. I wouldn’t want to be more than fashionably late.”

“Good luck.” Raikins waved as I headed out. He was going to hold back and change into another face. After that he’d go wander around for a while and end up hanging out near the party. If something went terribly wrong, he’d be able to back me up within a minute or two. Hopefully, I wouldn’t need the help, but it was good to know that it was there just in case.

I didn’t want to admit it to him, but I was a bit giddy. After a crazy week, I was ready to push for the next stage of the mission. I felt charged up. All the sex, and hell, even the work was having an uplifting effect on me. It was a new challenge, one that I could throw myself into in a way I haven’t done in years. Best of all, it helped improve my reputation in advance of the party.

I just couldn’t resist skipping at least for about a block. I felt absolutely ridiculous, and yet it felt so right. I finally managed to pull myself together and resume a more dignified walk before I got within a few blocks of the office. The party was being held there. Apparently, they had a whole floor that was dedicated to events like this as well as for other conferences and meetings. Tonight it would be decked out for us.

By the time I made it within a block of the office, I started to spot other employees. These kind of parties were not the thing that you would skip. It was also something people clearly were dressing up for. I was used to a pretty casual dress code around the office, but tonight, everyone was clearly coming in at least slacks and button shirts or dresses. I don’t think I’d been to such an event in years.

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