Undercovers Pt. 01

I would like to thank Sublocked for the editing assistance.

*****

The Big Day

Today was the proudest day of my life, my graduation from the NYPD academy. It had been a dream of mine for as long as I could remember. My Mom and two sisters had come to see me graduate. I was happy; ecstatic would be a better description. There were quite a few moments when I didn't think I would make it through. It was a mentally, and physically taxing six month journey. I had had a lot to prove as I wasn't physically imposing at five foot six, and a hundred and fifty pounds. Growing up in the Bronx I was called soft a lot. I got bullied, beaten up, and pushed around for being the pretty boy. I was always good looking but never a bad boy, which is what the girls liked in my neighborhood. To hear the word "Officer" before my name, Carlos Ortiz, was so satisfying.

After graduation the other rookies and I partied hard the entire weekend. When Monday morning rolled around I reported to duty not exactly my sharpest. I was still feeling the results of way too many shots of tequila. While everyone had received their assignments, I hadn't. So while my classmates were embarking on writing tickets, traffic duty, guarding hospitalized prisoners, and other rookie duties, I was told to report to the administrative office. I walked into the intimidating building wondering if they had made a mistake in giving me my badge. I knew I had scored low on some of the physical endurance tests. With these thoughts clouding my mind I walked up to the reception desk.

"Officer Carlos Ortiz here to see..."

The receptionist cut me off quickly.

"The Chief of Ds is expecting you. Take the elevator to the third floor and follow the signs" she said dismissively.

I pushed the call button for the elevator and waited. What the hell would the Chief of Detectives want to see a brand new rookie for? The elevator arrived; I got in and pressed three. I was feeling squeamish from the nervousness and the weekend of drinking. My stomach was turning and I began to sweat a little. On the third floor, I exited the elevator and followed the posted signs to the Chief's office. There was a woman at the reception desk outside his office.

"Go right in Officer Ortiz, the Chief is waiting," the woman said promptly without making eye contact.

I opened the door and stepped in; besides the Chief, there were two other high ranking officers and a man in a suit sitting at a table.

"Officer Ortiz welcome I am Chief of Detectives John Fieri. This is Deputy Inspector James Gall, of the Major Case Squad, Major Tom Nevin of the New York State Police, and Calvin Daniels with the New York Prison Bureau," the Chief said while firmly shaking my hand.

I was hoping the men in the room couldn't see the intimidated look on my face.

"Please have a seat Officer and hold your questions until the end" the Chief asked.

I sat at the end of the table facing the Chief directly at the head of it. It made me feel like a little kid being summoned to the principal's office.

"Officer Ortiz everything you hear today is completely classified, jobs and lives depend on it. The gentlemen here today are part of a joint task force investigating a corruption ring based out of Marsh Correctional Facility. As you may or may not know Marsh is a minimum security prison in Monroe County. Though it is far from NYPD'S jurisdiction, it houses mostly New York City's high level white collar criminals. We will be providing intel, as well as any other support we can to the State Police and the prison system. Going over your file with my colleagues here we feel you fit what is needed perfectly. We need a fresh face that no one knows to infiltrate this ring and gather evidence. You will be going undercover as a prisoner to garner the intel we need to bring this criminal enterprise down. You may ask any questions you have now," the Chief instructed.

"I have no experience sir. I don't know what I could offer this investigation," I said plainly.

"Officer we combed though your history, family background, psychological test results. Your mental composition and growing up with just women makes you perfect for this assignment," Deputy Inspector Gall said.

I couldn't even imagine what he meant by growing up with just women. I was more scared of what my psychological profile showed.

"Officer these criminals comprise Wall Street businessmen, former Judges, politicians, and such. These people prey on the weak. No disrespect but, you are the weak. Part of their enterprise is selling young men like yourself to the highest bidder. These young men are then feminized and used for personal use," the Deputy Inspector said bluntly.

"'Personal use', you mean sexually?" I asked. I was terrified, what did my psychological evaluation say about me? I'm sure I mentioned that I was bullied but what else was there. The sound of Mr. Daniels deep voice brought me out of my head and back to the conversation.

"Yes sexually. We need to shut down this racket and arrest the guards who are part of the operation," said Mr. Daniels.

"Let's face it Officer Ortiz you don't exactly cut the mustard here. We passed you through with this mission in mind. If you can't do this then you're out of the department. If you decide to help out, then I will make sure you land in a department of your choosing. Are we clear on this?" Chief Fieri asked.

"Yes sir," I said weakly. I had the hugest pit in my stomach and a feeling of nausea.

"You will be leaving now with Daniels and Nevin. Also you are to have no contact with anyone not currently in this room. They will escort you to the State Police headquarters, where you will be prepped for the assignment. You're dismissed," Chief Fieri said firmly.

I waited outside his office with an uneasy feeling. I was scared beyond belief, I was going to prison. As I looked through the windows of the office I could see the men exchanging handshakes.

Over the next few weeks I worked with Nevin and Daniels learning my back story. They grilled me over and over until I knew every detail of my new identity. I felt relatively confident I could pull this off; I really didn't have a choice.

The big day finally came. I was being transported to Marsh Correctional as a new inmate. It was surreal putting on an orange jump suit and being handcuffed. I was loaded into a prison van and driven away. We pulled into the intake area of the prison where guards came out to meet the awaiting van. My driver signed forms as well as the guards from the prison. I was then taken inside for processing, strip searched and seen by medical. A guard came in and escorted me to another room.

"Wait here," the guard told me.

I had a seat on one of the steel benches that lined the walls. I heard the door slam and lock behind me. Forty-five minutes passed before I heard an adjoining door unlock, someone finally returned.

"Inmate Cruz, I am Captain Donnelly, head of the guards here. The paperwork says you're here serving a three to five for illegal accounting practices and fraud," he said in a monotone voice.

"Yes sir," I said remembering my training to keep my answers as minimal as possible.

Captain Donnelly proceeded to summarize the do's and don'ts, while staring me directly in the eye.

"If you do what your told when you're told, you shouldn't have any problems here,"

"Yes sir," I echoed again.

"Good I like your demeanor, I am going to assign you to Block A. You will fit in perfectly," he said and turned to walk away.

I heard him tell someone outside the door to take me to Block A. This was it, not knowing what to expect was horrible. I had to do this and do it well, if I wanted a future. Daniels told me that he had a contact on the inside and they would approach me when the time was right. I was hoping it would be sooner than later, I needed all the support I could get. They told me that they would inform my family I was on assignment and not to worry. I knew my mother would worry anyway, she always worried about me. I was worried about me.

I was led down the hall by a big, bald, burly guard to Block A. Inside the entrance to Block A was another room similar to the one I had just left, but this one had windows with blinds. I was told to have a seat and wait once more. I could see figures looking in at me through the blinds and talking. After an hour the door finally opened and two well dressed women walked in. The white woman dressed in a black pinstripe skirt suit spoke first.

"Welcome honey, you have been selected to undergo special training for your stay on Block A. My name is Adrienne and I will be one of your trainers," she told me.

Once she started talking I knew she was a man. I couldn't believe it, even though I had been informed of the situation.

"This is my colleague Elise and she will be assisting in your training," Adrienne told me.

"Hello Doll, as Miss Adrienne said we will be your trainers for the next few weeks," Elise said.

"I don't understand, what type of training?" I asked.

"You will become one of us girls," Adrienne said slyly. The words just seemed to slide off her neatly red painted lips.

"I am not sure what's going on here, but I just want to serve my time and that's it," I said as I stood up.

"Umm this is a feisty Latina," Elise said as she walked around me looking me up and down.

"Look honey, these are your options. Option one, submit to our training here and become one of us girls. Being one of us will entail a certain amount of freedoms which you will enjoy. Option two; you will be transferred to a maximum security facility. Your transfer entails being someone's bitch with no freedoms at all, your choice," Adrienne said plainly.

"Do I have to decide this now?" I asked.

"Right now Doll, 'cause that transport will take your pretty Puerto Rican ass right back up out of here," Elise said sharply.

I stammered, "I guess I will take option one."

"Good choice. Follow us," Elise told me.

"I'm Dominican," I said.

"Ok, just bring your pretty Latina ass," Elise said as they both turned to lead me away.

I followed them out of the room as the sound of their stilettos echoed off the concrete floors. I was in, but was I prepared for all of this.

The other (Big Day)

In hindsight the men in that office six weeks ago looked like prophets. They must have seen something in my psychological profile to make them think I was perfect for this job. I was upset that they had hit the nail on the head. I had been locked in this one room for three weeks. I had been trained and drilled by Elise and Adrienne for twelve hours a day. I sat in front of the mirror touching up my foundation and lipstick. The flowing curls of my long, black, human hair wig framed my face. I was hoping at some point my contact would have reached out to me. But, I knew that was impossible being that I hadn't left this room, and apart from Elise and Adrienne, no one was allowed in. Elise and Adrienne told me that I had been sequestered per the Judge's instructions. I had asked about the Judge a few times and gotten the same answer each time. They would say "He runs this entire place and that's all you need to know."

I heard the door unlock and Elise and Adrienne stepped in. They were dressed in evening gowns and beaming with excitement.

"It's Graduation Day, honey. You are finally leaving this room and moving into the Block," Elise said, as she smiled.

"So what now? " I asked.

"Now you are going to go out here, look pretty, and see who wins," Adrienne said.

"Wins? Wins what?" I asked worriedly.

"Wins that pretty Dominican ass at auction," Elise told me.

I was terrified, I'd been here three weeks had learned nothing of the operation and was now heading to auction. I sat and stewed in fear that I had not thought this through. That day in the Chief's office I should have just quit. But, my family was so proud of me, and I didn't want to let them down. Sitting here in this tight, little black dress I was past second thoughts. A loud knock brought me out of my thoughts. A raspy voice said "It's time."

"Let's go honey that's our cue," Adrienne said, as she took my hand. I was mortified as I stood up with an empty feeling. I felt like I was in a trance, or mystical daze. Elise had tugged down the hem of my ridden up dress that I had neglected. They led me to the door. The last time I was led to a door there were two pairs of heels clicking; now there were three. The door opened and I was led out onto the block. The block was a large rectangular space with doors to cells lining the walls. It had more of a feel of a college dormitory. There were twelve cells on the first level and stairs at either end leading to a second level with fourteen more cells. Tables and chairs were in the middle of the room with people standing and watching. I could see that none of the prisoners wore prison clothing. Some of them were dressed in shirts and ties, some in sweaters with dress slacks or khakis. The "girls" were wearing the preferred look their men wanted them in, I was guessing.

I stood just outside the door that I had come through, with Adrienne and Elise on either side of me. They seemed like proud mother hens. I felt as if all eyes were on me. The same raspy voice that had accompanied the rap on the door, and told us to enter, spoke once again.

"Please remain standing, the Honorable Judge Raymond Fells now entering," the man said.

The judge entered out of the corner cell and took a seat at a huge mahogany desk. After he sat, everyone else in the room followed suit. He cleared his throat and began to speak in a deep, commanding voice.

"We all know why we are gathered this evening. I'm told we have a fine Dominican beauty for sale this evening. Please let us have a look, shall we?" the Judge said.

Adrienne and Elise walked me over to a table. They motioned for me to step up on to the chair and then onto the table. I had to hike the dress up a little before stepping onto the chair, then the table. As I stood up there, pulling my dress back down, I felt like a piece of meat. All of the men were talking to each other in hushed voices. The girls were either smiling, or cutting their eyes jealously. The men slowly made their way up and circled me some rubbing my sheer black pantyhosed legs. Some of the others were obviously trying to take looks up the short dress. This went on for what seemed like an eternity, but was more like twenty minutes.

"Okay now, let's get to it," the Judge said.

Everyone returned to their seats and waited eagerly.

"All interested parties can now submit their sealed bids to my assistant, Carl. I will have a brief recess and return with the results of the highest bidder."

One by one men walked up to the raspy voiced Carl, and gave him sealed envelopes. When no one else appeared to step forward Carl then announced, "Bidding has now been concluded and bids will be submitted for review."

Everyone once again stood up as the Judge adjourned to his cell, with Carl following him. Adrienne and Elise helped me down off of the table top.

"You're doing good Chica, just keep it together," Elise told me.

"It will all be over soon, and you can begin your life with your new husband for the next three to five years," Adrienne laughed.

We sat at the table that I was just standing on top of in nervous silence. I could still feel so many eyes on me as I tried not to notice. Carl entered the room and we all stood as the Judge followed.

"After reviewing all of the submitted bids I am pleased to announce the winner is, David Garner," the Judge said. He then quickly stood and left the room. Mr. Garner approached and Elise took my hand and gave it to him.

"Here you are Mr. Garner she's all yours," Elise told him.

I hated myself for having such conflicted feelings. In my mind I was thinking I had lucked out from the looks of the other men who had bid on me. I didn't want to think that David was a good looking guy, but I did. Perhaps it was because I was standing here dressed as a woman. Maybe it was the psych evaluation, which made my superiors think I was perfect for the job. David led me slowly to the other end of the Block where our cell was located. What seemed like a sea of people parted as we walked. I could hear whistles and cat calls. I felt slightly guilty for feeling like the belle of the ball. Concentrating on my walk, I placed one five inch heel in front of the other. It almost felt like I was mentally prepared for this.

Physically I wasn't prepared at all. I stepped inside the well decorated room just long enough to have a quick look around. It looked like a very small but expensive hotel room. My face hit the cold egg shell painted concrete wall with a dull thud. My face burned from the pain as my eyes instantly filled with water. I could not muster any sound as shock had taken over my body. I could feel him grab the hem of my dress with both hands and pull straight up. My heart filled with fear of the impending Rubicon I was crossing, after which I knew I would never be the same. David squeezed and rubbed my padded ass for a few minutes before dispatching my body shaper up around my waist. Layer by layer he exposed me, slowly lowering my pantyhose and panties down around my hips. I had lost hope that my contact on the inside would come to my aid. Now I could hear David lube himself before pressing the head of his hardness against my virgin opening. I felt pressure and pain as he pushed forward slowly. I didn't hear it but I could feel a whimper escape my lips. David covered my mouth with his left hand as he pushed in further. I had finally gathered enough of my wits to remember Adrienne and Elise telling me I would have to relax at this moment.

When they had told me I had thought I would never get to this point. Now up on the balls of these black patent five inch stilettos I finally relaxed. I brought my heels back down to the floor and slightly arched my back. I relaxed slowly, relaxing my anal muscles as I could feel his entire length slide inside me. David put one hand on each of my hips taking a firm grip. He started pounding me hard; I was hoping this would quicken the process. He was now breathing heavily as he thrust in and out of me. I placed both hands on the cold wall and pushed my ass back to meet each thrust. I could feel his hot fluids start to leak inside of me. Finally after a few more minutes with both hands now with a tight grip of each of my breastforms, he erupted inside of me. His once hard erection was now subsiding and convulsing the last of his spew inside me. He pulled out of me and backed up to sit on the chair behind him. I could feel his molten solution running out of me. It was now running down me and settling into my waiting lowered panties and pantyhose. I peeled my face off of the wall and stumbled back a few steps. I felt a mixture of tears and foundation stream down my face. I turned and faced him as he sat there with quite a content look on his face.

"So, Daniels sent you huh?" David said.

My mind was blown; I had just been taken by my contact. My mind was racing as I scrambled to pull my panties and pantyhose back up. His sticky juices were slowly adhering the satin panties, and nylons to my body. I lowered my dress, slowly walked over, and sat on the bed facing David.

With a stoic face he just looked at me.

"This had to be believable; I assure you there were ears outside our door. If not spies there was probably a pervert or two. So, just silence was not an option. Don't get your panties in a bunch," David told me.

Unfortunately my panties were literally bunched. I sat there wrestling with the conflicts of being taken and enjoying it.

David continued, "Listen we have work to do and you're going to have to buckle down. You've got to really immerse yourself in this role. If not, it could end up deadly for the both of us. These guys don't play we will both end up looking like accidents," David explained.