Undercover Female

I was one of the early "modern" female FBI agents. I graduated from college in the 1970's, with an unusual combination of a both accounting and computer science degrees and a CPA. I also ran track in college and was in pretty good shape. I applied to the FBI and was accepted, and after my training and probationary work I found myself assigned to a white collar crime unit.

It was boring and routine for many months, as we downloaded transaction records and used time sharing computer terminals (this was before PC's and spreadsheets) to compare and match bank transactions with potential criminal activities. Much of stuff we found was handed off to other agencies – potential counterfeiting or money laundering to the Treasury pukes, some foreign transactions were deemed "espionage related" and handed over to the FBI units specializing in counter intelligence, and a lot of potentially exciting stuff went to the OC weenies.

I spent all my time in a cubicle tracing transactions and trying to get bank MIS managers to volunteer data without a warrant and to output tapes in a format we could read. Except for my trips to the firing range, and the occasional special training, my glamorous FBI career seemed no different than those of my accounting classmates who took jobs at the Big 8 accounting firms (there were eight then, but not anymore!).

My sex life was not much more exciting – I had a few college boyfriends but none that really lit my fire, so during college and especially after I started at the Bureau there was lots of fantasy and masturbation. I had two older brothers and an older sister, so when I was growing up I not only got to read Playboy and Penthouse Forum, but I also discovered porn magazines hidden in drawers, and snuck in to watch 16mm porn films projected on my brother's wall when they thought I was asleep. But I got most of my sex information from my sister's Cosmo and Redbook magazines, and eavesdropping on her stories and those told by her friends when they slept over at our house, plus another more advanced course of study by listening to the other girls at college.

Then there was finally some excitement at the FBI field office when our boss announced that several special agents, including me, were to be temporarily assigned to a task force to work with the ATF and the DIA on a weapons smuggling case. Things began to move fast when we were told that there was considerable attention to our case from not only the FBI directors' office, but the White House. There are often great budget implications in the outcome of something like this, and careers can be made or broken in the rush to show quick results.

At first I was given a huge file of records from an expensive escort service that had been "turned" by the local cops, and then handed over to the FBI when it was discovered that it operated in several states. This operation provided super high end ($5K per night in the 1970's!) call girls who were in real life sorority girls good looking enough to be models and willing do just about anything the client wanted!

I took the files to my office and then recruited two secretaries to do rapid data entry all night and then my months of boring experience paid off. I was rapidly able to identify most of the clients, their credit cards, their schedules, and I even found some amateurishly 13 letter code encrypted journals with notes on their sexual preferences. These were easy to decipher and I typed them up too.

When I turned this information over to my boss, he scanned it, got visibly excited, and then went into the SAC's office and they called the Bureau HQ in DC, even though it was already late evening there. He didn't let me listen to the call, since this operation was officially compartmented, but by what I could hear through the door and from the tone of the voices on the speaker phone, I could tell there was great urgency to get more information.

The next morning the SAC called me into his office alone, which in itself was unusual. He was bypassing my direct superior and several members of my team. He first gave me a brief "attaboy" for working through the data so quickly, but he soon grew thoughtful and spoke in hushed tones.

As I later learned this usually means they are about to try get you to do something that will either earn you a big promotion if it works or get you in trouble with OPR if it doesn't. Your boss will get most of the credit if it works, but will have to act really sad when they fire you for coloring outside the lines if you don't get results.

"Connie," he said, "You are the only agent with a chance to break this case and to perhaps advance your career in a very short time. But you will have to tread carefully. I want to make sure that you understand I am not asking you to do anything that puts you at risk or makes you uncomfortable. Is that perfectly understood?"

I paused for a minute and asked "What exactly are you asking me to do, sir?"

He adopted a conspiratorial tone like he was reading me in to secret stuff I really shouldn't know: "One of the escort clients you identified is a major player in the arms smuggling operation we are trying to track. He has been seeing the same girl for almost a year, but she has paid off her student loans and will not go on any more dates with him or anyone else. The madam is so worried about getting us to reduce her sentence that she will do or say anything we want. There is a big party planned and the escort service is sending 4 girls to the hotel suite. We want to put you undercover as the new replacement date for the top arms dealer."

It took me a minute to process the possibilities here. "What information do you think I can get, and what do you want me to do to get it?" He paused, and chose his words carefully: "We want to know who he is selling to and when. It may be that one or more of the other guys at the hotel are the buyers, and we can actually make an arrest before the party really gets started. But you are going to have to make a judgment call on that. You will be the one to signal when we should make the raid."

Being lucky enough to have it all go down that night seemed unlikely to me, and I asked "What if it's just a party and no transactions take place for a long time?" He considered this, and replied "If you don't feel you can continue the operation, try to get out without signaling for a raid. If we don't alert him, maybe we can just keep a team following them after the party breaks up, and that will get us what we want. These guys are freaks for counter surveillance, and have a team following them and snooping all the time, so we won't be able to wire you and listen in."

The walls started to close in on me a little bit, and I asked "If you are not listening in, how can you tell when I want a raid?" He pulled out a pager on a clip like all the doctors wore in the 70's. "Take this with you. All the escort girls have them. The service pages them to call for their messages and also the madam pages them and they have to call her from each date to tell her they are okay. All of the girls do this and your target knows all about it from his times with the previous girl. We have modified this pager receiver by adding a low power transmitter so that if you press the squelch button three times quickly it will send an alert signal to our surveillance team. It only transmits when you are ready for the raid, and if we tried to send any other signals they would sniff them out and the deal would be blown."

"Why are you giving me this thing now?" I asked. "Because the party is tonight, and it will take some time to get you ready, so you have to decide right now". He looked at me expectantly. I needed some more information. "What do we know about the client? Who is he?" He looked troubled. "You are supposed to be meeting him for the first time. If you know too much about him it may jeopardize your cover story." He did not put me off. "I still need to know more about this guy to gauge the risk – to decide whether or not to try this at all."

He made a grimace. "We don't know that much anyway. He's supposed to be in his early thirties, former Army Green Beret with combat duty in Vietnam, then a mercenary and now an arms dealer. Calls himself Danny Colangelo, but that's probably an alias. Six two, two hundred pounds, blue eyes, brown hair. Nothing else I can tell you. Are you in?"

What was being left unsaid was that all these arrangements were tailor made to make me the cutout and the bearer of all the risk. If I didn't send the signal, my boss and the rest of the team would blithely assume there was no problem. If I sent the signal too soon without getting any evidence on the arms transactions, I would have been the one to "chicken out" and ruin the operation. And if I stayed undercover until I got good information, who knows what I would have to do with "Danny" for how long while my bosses stayed blissfully ignorant?

"Why me" I asked. He spoke immediately: "Because you are about the same age and background as the recent college graduates the madam recruits. You will be completely believable if you tell them you are doing it to pay off your college loans. And although you don't normally dress like a hooker, our consultant says that he can tell from the pictures we sent him that you are in good shape and have a nice figure. He says he can "tart you up" and make you look like a hot call girl! And no one else who could pull off that look knows enough about the case to be useful given our short time line."

I realized this was my chance to move up in the bureau faster than I ever dreamed. And then I realized something else. The prospect of having "Danny" think I was a super sexy high end whore and tell me exactly what he wanted me to do to him did not disgust me. In fact, it made me a little hot. Some of my recurring fantasies involved daydreams about going to a fancy hotel room with a great looking date that I knew was going to expect me to go all the way. And during my daydreams I would see myself doing just about everything I had ever seen in the porno films or read about in the magazines, and finger myself to several fine orgasms in the process.

"Okay, boss. I'll give it a try. But who the hell is this consultant?" One of things that continues to amaze me about the Bureau is the people they bring in to help them prepare for cases. I have no idea how they find them, or how much they pay them, but they often have amazing skill sets I never even dreamed of.

"We have him and the madam in a conference room downstairs. She is going to give you a short course in the world of play for pay while he does your hair and makeup over so you look like a whole new woman", he laughed.

The guy in the conference room looked and sounded a lot like the Michael Caine character in "Miss Congeniality." For all I know he may have been the actual inspiration for that role. I learned that he was a former Hollywood makeup artist and special effects man, who was a master of making disguises that completely changed someone's looks and were still quick and easy to apply. He immediately began pawing me like I was a horse for sale, first grabbing my face like my grandmother used to and said "good cheekbones – we can use that." The he pulled down my top and said "Look at those nipples! Those are two in a million, you know that don't you dear? We can work with those babies." I have always been proud of my nipples. They are the color and shape of a brand new jumbo pencil eraser and about the size of a .44 magnum bullet. Every boyfriend I have ever had has been fascinated with them, and I never tire of having them touched and kissed. Mr. Makeup said "I could almost get interested in them myself. They look like nice little pink cocks!"

I pulled back to punch him and the SAC grabbed my arm and said "Let him work, Connie. He's a pro." Mr. Makeup pulled up my skirt and whistled. "Wow, great legs, you must be a runner. I could almost get into girls if they all had gams like yours." He stepped behind me and cupped my ass cheeks with his hand. "Wow again. Your workouts are paying off. We'll put you in very high heels with a very short skirt, and with those legs and that ass most guys won't even notice what color your eyes are until the third date. I need to see your pubic hair, sweetheart. Take off those hideous cotton panties. We are going to replace them anyway!"

Again the SAC warned me not to hit Mr. Makeup, and then left the room smirking. "I'll leave this to the pros."

Mr. Makeup motioned for the cosmetologist to come forward to work on me. They boosted me up unto a large towel on the conference room table and she proceeded to shave my bush and trim the pubic hair that was left. Back then I kept my red brown hair long and usually wore it up in a bun for work. Mr. Makeup removed the simple leather tie I normally used, and the madam handed him a Chinese lacquered hair thing. He twisted my hair up into tightly wrapped tower and the Chinese thing clamped onto it like a clamshell from the left and right side, and had a series of indentations on the back side. It almost looked like a pair of upside down pearl handle pistol grips, and I wondered about the shape.

"You'll see what that is for later, dear." Said the madam, who looked to be about 65 years old and must have been a real looker in her day. "Let me give you a few tips. This is basically what I tell all the new girls. Hookers don't get paid for sex – they get paid to reliably and discreetly to go away afterwards. High end call girls get paid for that and for creating an illusion of warmth and willingness. Sexual skill doesn't matter nearly as much as acting skill. Nothing is sexier for a man than a nice looking woman that is willing to listen to him and look at him like she finds him interesting. Everything else is extra. If the guy actually turns you on, then you just go with it. We don't have to worry about him – the way you will look after we get through with you will turn him into a monkey in heat. If you are into the guy, don't be afraid to tell him what you would like. Guys love it if you ask them to do things to you."

Mr. Makeup finished with my hair and began holding some color sample cards up to my face. He said he was checking my skin tones to find complementary and contrasting colors. He then started to apply makeup to my face, narrating as he went along so I could duplicate it later. He showed me where to put some darker coloring to make my high cheekbones stand out and make my eyes look bigger. Combined with the hair up high, it made my face look long and elegant, and the new tones in the makeup also made my eyes and hair color "pop" and look very bold. The guy really did know what he was doing.

He handed me a bright green bra and told me to put it on. The bra was a very aggressive push up type with cut out holes for my nipples. The green color contrasted perfectly with them and made them seem even longer and pinker. It pushed them up and popped them out like a retail display. They immediately swelled up and got all "crinkly" like they did when I was excited. The cosmetologist leaned over a little too closely and licked her lips. I was afraid she wanted to kiss my nipples. I was afraid I might like it.

Then he handed me some tiny panties of the same fluorescent green color. I put them on and realized they were crotchless! The cosmetologist reached out to adjust them. I saw that she had trimmed my pubic hair to match the shape of the cut out in the panties. She held up a mirror so I could see myself. With the bright green color, the contrasting pink lips and reddish brown triangle of short hair, my crotch looked like a green and red neon sign pointing to the pussy in the middle of it! Even I wanted to kiss it! I had to force myself to focus on what the madam was saying. I started to think about how to keep myself from getting wet.

"Here are the notes the other girl made about this client" she began. "Up tight – never wants to do orgy. He always wants one on one in private. Acts very different when the other guys in his crew are around. Makes sure the door is double locked and then even puts the chair under the door knob. Keeps a big gun under the pillow and another smaller one in his shoe. Lots of foreplay and kissing – it's almost like he wants to drag things out and delay, not come fast like most do. Very oral. Spends lots of time on my legs and ass. He knows when I am excited and you can never fake on orgasm – he knows if you come and he usually makes it happen. Never calls me whore or slaps me. I asked him to spank me once and he sort of liked it, but I think he was embarrassed that he did. He is gentle but when he finally gets going is a very strong finisher. Does not like it when I talk dirty, but he does like it when I sweet talk him. Once I put his hands on my head and encouraged him to face fuck me. He really got into it, but he seemed sheepish and embarrassed afterword."

I was getting more comfortable with the risk, and also getting hornier!

Mr. Makeup handed me a little purse. It was expensive Italian leather, and had a driver's license in it that looked completely authentic with my undercover name and the picture from my most recent actual license. It also had about $300 in cash, some makeup and lipstick, an expired student ID for the undercover name with the picture from my last college ID (nice touch), the pager, some breath mints, and some chic looking dark glasses in a hard case.

He slipped a very expensive looking basic black dress over my head and I shook it down into place. It fit me like a glove. It covered my chest, but the fabric was so sheer it was easy to tell that the bra had openings for my nipples. They promptly stood up like bullets under leather!

The dress was very short. It seemed like it only went down about an inch below the crotchless panties. I could feel the draft in the room on my pussy lips! He handed me a pair of expensive Italian shoes – very high heels and multiple straps that climbed up my ankles. Today they would call them "Fuck Me Pumps" and even back then the message they sent was pretty clear. They also were so high and tilted that they emphasized my legs and ass even more than the dress alone.

I tried a few steps in them and the cosmetologist loudly sighed. "Oh honey!" she said. "You look like a million bucks!" Mr. Makeup beamed. "I am a fucking genius, am I not!" I had to admit, I looked like a different woman. A very hot and very fuckable woman!

The SAC opened the conference room door and froze in place. He scanned me up and down and then his eyes fixed on my nipples. He ground his teeth together so hard we could hear the muscles pop in his jaw! Mr. Makeup almost protectively put a nice Burberry rain coat around me, with a hood and a snuggly warm lining. It was cold and snowing outside. "The car service is here" the madam said. "He is picking you up first so the other girls won't know where you came from." The driver was from the madam's regular car service – he did not know I was undercover. I went downstairs and left the building via the restaurant and bar, located the black Lincoln Town Car, and got in. The driver acknowledged me and said he had three more pickups to make.

Soon the car had all four girls, and we drove on to the hotel. We got out and I followed the other girls. One of them slipped the concierge a fifty and he used a key to let us into the elevator to the top floor. They were all about my age and very pretty. The tallest one with jet black hair asked "is this your first time with these guys?" I decided I couldn't fool these girls about my inexperience. "Yes" I said. "It's also my first escort date with anybody!"

She looked at me incredulously. "HOLY SHIT!" she exclaimed. "The three young guys are pretty wild. They are into gang bangs!" I thought quickly, and said "the madam said I was for the older guy only. I am replacing the girl that he used to go with". Another girl said "Didn't she tell you about those Chinese hair handles?"