Losing Myself One Drop at a Time

"I feel really good," I grinned and continued, "I love leaking for Rubina. She is so amazing and beautiful."

"Yes, she most definitely is," she smiled back and walked over to me.

She traced a finger down my jawline and said, "Soon you'll be just as pretty as her. Would you like that?"

I wanted to say no... But over the last few weeks Rubina had been telling me those things every time she fingered me; "You'll be so pretty, dear," "You'll love the way you feel as a woman," "We can be girlfriends and I'll help you become just like me."

She continuously told me things like that, and I wanted it, so I blushed and responded to Emma, "Yes, I would like to be pretty like Rubina."

She held her hands up to her mouth and giggled excitedly, then said, "Oh my gosh, yay! I'm so glad! We figured that might be the case."

"What do you mean?" I asked and squinted at her.

"Well, who wouldn't? Of course," she answered back quickly.

"O-oh, yes of course," I responded. As silly as it was, I was concerned that they knew my past, my secrets, my fantasies.

I mentioned earlier that I had experimented in college. Well, at the time I was using online chatting and forums to play around with the idea of being a woman... I called myself Joselyn.

I felt so free and real. I can't even describe it. I couldn't pursue it though, not if I wanted to be in the FBI. So I buried it, and hid it all away. There's no way anyone could find it though, so I relaxed a little as Emma continued.

"We are going to be moving you to a more suitable room now. We are giving you more liberties and freedoms while you are in it, please do not abuse our trust in you," she said as my bonds loosened.

I pulled my arms out and looked at them and back to her. A hundred possibilities ran through my head of what I should do. I could attack her, try to get out, try to escape. "She isn't built like Rubina, she is a ciswoman. I could take her," I thought to myself.

However I truly knew nothing about my situation. If I tried to make a move now, while I had no tools and no knowledge I would surely fail.

So I simply stood there and said, "Thank you, that sounds nice."

"Follow me," she said as she walked out of the room into what seems like an old hallway hospital that had been renovated.

"I'm naked though," I say as I hesitate to follow and gesture to my naked body.

"No one cares about that here. Come!" she demanded as she continued on.

I slowly followed her out. Noticing that no one was in the hallway but us. As we walked I tried to take in as much information as I can. There were many cameras and security doors and rooms between my last room and the new one I was headed to.

She finally led me to a different section and opened door 213A and motioned me to go inside. I made sure to note details like the door number as much as I could. You never know what will make a difference later.

Emma shut the door behind me and I was alone in the room with Rubina. She smiled at me and said, "Hello dear, let me give you a tour of your new room!"

"So over here is your vanity. Very important; I'll be teaching you many things over here," she started as she motioned toward it.

"Here is your shower, and there is your bed," she said as she walked by them.

"And last of all is the most important part of your new room. This!" she exclaimed as she motioned toward a machine in the corner.

The machine almost looked like an exercise bike, a long seat that had some lower back support, what looked like maybe handles, and a place to put your feet. Though it seemed small for me.

"Come try it out, please sit down," Rubina said as she patted the seat.

I walked over and sat down in the seat then she pushed me forward until my upper arms and shoulders rested on what I thought were the handles.

"Ah, perfect, now for the seat adjustment," she said as I felt the seat being curved to fit around my lower back, ass, and the skinniest part of the seat up over my crotch.

She then grabbed my legs and placed them up on the machine close to my ass. I felt so scrunched, my knees almost touched my chest and my legs were bent so much.

"There we go. I set this up just for you, and it's a perfect fit," Rubina said proudly.

I pondered it all for a minute then asked curiously, "What is this even for?"

"For milking, my dear," she said tightening a couple knobs on the machine.

"Um, how? You can't reach my um... well anything," I responded.

She giggled and stood in front of me with a tablet of some kind. Then looked up at me and said, "You are too smart sometimes, too much overthinking. Reach down and spread your cheeks."

I did as she asked even though I was confused. Then she tapped the tablet and I felt a cool metal lump pressing against my hole.

My eyes went wide realizing what was happening and I tensed up and stopped pulling my cheeks apart.

"Calm down, dear," Rubina said as she walked over and started caressing my back and sides. Her touch was always so relaxing.

She rubbed down to my ass, then gently grabbed my cheeks and pulled apart. She whispered in my ear, "Just think of it as an extension of me."

As she said that I felt the metal rod slide up into me. It was only slightly larger than her two fingers that I was so accustomed to, so I could easily handle the size.

"I calibrated the machine myself, so in a way it is me. It knows exactly how to rub you," she said as she let go of me and tapped the tablet again. The probe in me started gently pressing against my p-spot.

Rubina began rubbing my back again and I relaxed completely. "Are you going to be a good girl for me?" she asked softly.

For the first time in weeks I felt my member jump slightly. I don't know why but that question sent a chill down my spine. I tried thinking about how to answer not wanting to come across as desperate as I felt, but only one thing came out, "Yes."

"Keep those cheeks pulled apart for me then, and I'll give you a reward," she said commandingly.

I immediately responded, grabbing my ass and spreading it to please Rubina. I was excited and unsure what my reward might be. Then I felt her remove her hand and I heard the tap on the tablet.

I felt the rod in me squirt my prostate with the cream I was addicted to. I moaned and arched my back. I blushed a bit after thinking about my reaction. I had truly become such a butt slut for Rubina.

She giggled and walked back around in front of me and said, "We have so much work to do, but we'll get you there, dear."

She tapped the tablet again and the tip of the seat started vibrating slowly but intensely. Sending waves of pleasure throughout my body like I've never felt before. They were so... Deep. That's the onky way I can describe it.

She rubbed her finger along my hairy chin and said, "I'll help you shed the manly form to be a beautiful woman. Would you like that?"

"Yes, Rubina, I'd love that," I responded trembling all over from the pleasure.

"Beg me to make you a woman, dear," she commanded as she moved her face inches from mine.

I didn't really want to beg her, I just wanted this feeling to last forever. I did want to make her happy though, seeing her smile made me feel so good.

So I did as she asked, "Please, please make me woman. I want it so badly. It feels so good. Please."

She tapped the screen once more and leaned in and kissed me. The rod inside me started pulsing in and out very quickly in time with the deep vibrations from the seat. Each time it pressed against my p-spot I could feel it get wetter inside.

I moaned uncontrollably and shook all over. I was in total ecstacy, nothing else even mattered at that moment, not even who I was or how I arrived here.

She kept kissing me and rubbing my side as the machine kept at it. Eventually I couldn't handle how good it felt any more and I could feel the wetness all over my crotch as my cum leaked out of me, along with more of my manhood.

Once she felt like I had enough Rubina stopped the machine and the rod rectracted back into the seat. Then she helped me up and guided me to the bed.

"You're gonna be perfect once we're finished," she said as I curled up and drifted off to sleep.

The next month and a half consisted of lessons from Rubina on how to do my makeup and hair, laser treatments for my unwanted body hair, daily yoga and exercising, and more milking everyday that I loved and looked forward to.

By that time I had a small set of breasts on my chest and I looked very feminine overall. I really was leaking away my manhood like they told me at first, but I was enjoying it so much I couldn't stop anymore.

Sometime about a month ago Emma showed up in my room. She hugged me and said, "You look so beautiful! You're coming along very nicely."

I blushed at the compliments. Rubina and I had been working very hard and it was nice for it to be noticed.

"So! Rubina tells me you are ready to start the process of being allowed to leave?" Emma asked.

"I guess? I didn't know it was a process. I just think I should be allowed to leave my room now," I responded calmly.

"Yes, it is a process I think you'll enjoy. Please sit on your milking machine and I'll explain," Emma gestured then walked over to it, pulling the tablet out of her bag.

I was nervous following her, because I've only ever been pleasured with it by Rubina. I sat down on the machine and nestled myself in.

Emma tapped tablet a few times, but the machine didn't stir. She looked up at me and smiled, then asked, "Agent Zeiss, has that always been your identity?"

I was unsure of what the question meant, but answered anyway, "Yeah, who else would I be?"

"Well, I was thinking you may have at one time been her," Emma said as she tipped the tablet toward me slowly. On it was a picture from a time I mentioned earlier. When I was dressed as Jocelyn a few years ago.

I instantly started trembling and asked, "Where did you get that?!"

"You've been here for quite some time. More than enough for us to learn all about you and go through your whole computer and history and well, everything," Emma said coolly.

"We probably know more about you than you do," she finished then giggled as she flipped through more pictures. I looked terrible then compared to how I look now.

She continued, "That's how I knew you'd love to be Jocelyn, but just being a woman isn't enough to warrant your freedom from this place."

This was the first mention of freedom I've heard since I arrived at this place. I had essentially resigned myself to being stuck here forever. I never thought about what would happen if I was free.

Emma must have noticed my response, because she laughed and asked, "Did you think we'd keep you here forever?"

"No no, silly girl. I told you at the beginning, we need your talents. Your knowledge and training will be so appreciated by us," she said as she rubbed my cheek softly.

"What could I possibly do?" I asked.

"We, of course, need helping turning the marvelous cream that made you the girl you are today into a worldwide phenomenon. We want men everywhere to cum their masculinity away, and weaponizing drugs is exactly what you're good at, right?" she said sweetly.

I'll admit, it felt really good to be acknowledged for my skills, and be desired for it. On the other hand, using my training for that purpose is the opposite of what I wanted to do with my life. I wanted to keep people safe not turn men into women.

"I-I don't think I can do that," I told her timidly.

Emma looked me right in the eye and asked, "You can't do what? Bring men the pleasure you've been feeling these last few weeks? Help them connect with the softer things in life? And gain your freedom back into the world at the same time?"

"That's silly Jocelyn, of course you can. I'll give you a couple days to think about it," she said as she walked out.

For the first time since I've been here I was sitting on the machine feeling no pleasure at all, in fact feeling quite bad, like I had disappointed her.

Why was I feeling bad about that though? She was my captor. "This place is messing with my head. I need to get out," I thought to myself.

A few days of the usual went by, Rubina and I talked about Emma's offer and she of course encouraged me to take it. That alone almost made me say yes.

Then I realized I could say yes, but not follow through, and once I was free I could expose this place. So I decided that now was my chance for deception. I've been so honest this whole time they won't expect it at all.

When Emma came back Rubina was with me and I was being milked gently. So little came out each time now. Just to get a tiny drop to leak out took such long sessions,l; about an hour each time. We were about halfway through when she arrived.

"Hello, Rubina. I'll take over, please," she said as Rubina handed Emma the tablet.

She stopped the machine leaving me very needing. Then she asked, "Well Jocelyn, have you made a decision?"

It took me a second to put the thoughts together, my head swimming in bliss still. I finally said to her, "I have, Emma. I will help you, as long as I get my freedom in return."

Rubina jumped up and down for joy beside me and Emma smiled and walked closer and said, "Of course! That is the arrangement, that's why you're even here to begin with."

"Please sign these documents," Emma said as she held up a packet of papers. I tried to read them as much as I could. One was my resignation from the Bureau. One was something about consent being here. Another was liability or something... All kinds of things.

I didn't really want to sign them, but I knew I could later state that it was signed under duress, so I went ahead with my ruse and signed them all.

"This begins a new phase of your transformation," Emma said as she tapped the pad many times then continued, "from this moment on Rubina will no longer control your milking, you will."

"Me? But, I would rather she do it," I said looking over at the radiant woman that's been training me.

Emma held the tablet in front of me and said, "Say this out loud."

"My name is Jocelyn," I read what was written. When I did the machine vibrated and stimulated my p-spot for a few seconds.

I moaned softly and blushed a little; still shy about enjoying it so much in front of my captor.

"Please, continue," Emma commanded.

"My name is Jocelyn. I'm a good girl. I love being milked," I continued. As I did the machine continued and I felt so good again. I couldn't help but keep reading.

I repeated those same lines for a couple minutes then it changed and said, "I want to make men into women like me." I hesitated and looked up from the tablet.

Emma motioned for me to continue as the machine stopped pleasuring me. My hole felt so needy, then I heard a whisper in my ear, "Continue, butt slut." Rubina said as she started caressing my back.

"I want to make men into women like me," I said cautiously, but the tablet heard me and the machine re-engaged and squirted the cream deep in me again. I shook in sheet bliss.

"Of course you do," Emma said with a giggle then she kissed my cheek and walked out.

I continued to repeat the lines on the tablet as Rubina caressed and kissed me. My session continued like this until I leaked, same as it had been.

I knew what was happening. One of our courses in training was about mental conditioning. I was taught a few methods to combat it; detach emotionally, read it as if it's someone else speaking, imagine yourself at the academy in class relearning this training.

I also knew that it would only take time before I broke. It was little things at first; in my conversations with Rubina I now often call myself a good girl, and she asks if I am and I always say yes.

With Rubina having a little more free time I also got more freedom. I was allowed to leave my room and go to the kitchen area for my wing.

I was glad to learn that I was the only one in this area currently captured. I was slightly disappointed too; some allies to plot escape with and maybe just some other women to chat with would have been nice.

That's how I discovered this security room. Being allowed to roam freely I found ways in. Not before things got more difficult though. A new phrase was recently added to my conditioning and it's already got me.

"The buzzer means it's milking time." As I write this I'm afraid the buzzer will go off any minute, and I'll run to my milking machine.

I'm losing myself completely to the programming. I won't be able to resist much longer. I'm not sure what will happen when I do.

I truly desire to make men into women like me now. I've been coming up with ways to do it in my head. Once I have a proper lab, it won't take me long.

That's what scares me now; not Emma, not the machine, not the cream, but who I've become.

I'm so close to being lost in it all, swept out to sea by the waves of pleasure. Yesterday I did something I've never done before; with no one else around I got on the machine and milked myself.

Neither Rubina or Emma were there. It felt incredible. I got on at about nine pm and off just after midnight. That's the longest I've ever gone. Just repeating the mantras over and over.

That's what drove me to risk it all and break in here and write this. I can't risk oh my god I hear the buzzer! The buzzer means it's milking time

My my, it appears Jocelyn had a very busy night. Hello, this is Emma Taft. The one she wrote about. All that she has written here is true, of course, but it doesn't matter much, no one will believe this. Soon she will fulfill her duty to our cause and shape the future. A more feminine friendly future.

Goodbye friends of Agent Joshua Zeiss. He is no more.

Epilogue:

Hello friends and family! It's Josh... Kinda. Sorry I've been away for a few months, I was finding myself. My name is Jocelyn now! She/her pronouns, please.

I met an awesome lady that has helped me immensely. My love and queen; Rubina is my partner. She helped me transition and has been with me to support me the whole time. I'm her good girl.

I no longer work at the FBI, as my talents were underappreciated there. Now I work at a company that develops lotions and soaps. Exciting new things in that field, as crazy as that sounds.

I just wanted to let everyone know that I am happy and healthy. I'm living my dream life now. Something I wish happens for everyone.

Please ignore that other letter "I" sent a few weeks ago. Rubina was being playful and sent it out as some kind of prank. April fools!

Anyways gotta go, the bees are buzzing and it's time to do some milking. My company works heavily with natural ingredients. It's almost like working on a farm.

Girls rule! Peace out! - Jocelyn Zeiss