Undercover
written by:
Legally Blonde

It's pretty much universally accepted that legal interns will be doing more and different kinds of jobs than the standard job description includes. Getting coffee, rushing out of the courtroom to retrieve files, and picking up dry-cleaning were only a few of the multitude of tasks I had been asked to perform during my internship so far. None of these compared, however, to the task I was about to receive. I was helping out in misdemeanor court, sifting through all the public intox and minor possession cases, when I overheard a conversation between one of the prosecutors and a police officer. "Well," said the officer, "we've really seen a huge increase in prostitution over by the college campus. It's a huge problem because, while we try to pick up as many prostitutes as we can and process them, there's no way to really make an impact until we can catch some of the Johns too. " The prosecutor nodded his head, "Yeah, I agree. With prostitution, all we can usually do is give community service, and that's if they even show up to court. If we can get some of the Johns in, especially if they're young and in college, being arrested and getting a court date might just be embarrassment enough to be a diversion. Have you tried some vice investigations in the area yet?" The officer rolled his eyes and shook his head, "No, unfortunately we only have a few female officers, and really none of them are willing to do it. It's kind of a crappy assignment, and nobody really wants to spend a shift picking up these guys on such a minor charge. They have bigger fish to fry." The prosecutor thought for a moment, then asked, "Would you guys be willing to use someone that isn't on the force? We have some extra help in our offices. I bet one of the interns wouldn't mind helping out." Just then, the prosecutor looked up at me, noticed me eavesdropping on the conversation, and smiled...

"HOLY SHIT, YOU LOOK LIKE A WHORE!" I could always count on my friend Sam to be completely honest. She was one of the other interns at the office and was quickly becoming my favorite person to hang out with. She was a loud, redheaded siren who always said exactly what was on her mind. "Yes, Sam, that would be the point," I replied, smiling and trying hard to keep my hands from shaking. I had to admit, the outfit I was wearing was a far cry from my usual tailored business suit, heels, and pearls. I even shocked myself when I looked in the mirror. The red strapless dress started low, ended high, and hugged everything in between. Matching stilettos and a little red lipstick completed the ensemble. The only thing that had stayed the same was my shoulder length blonde hair, which I had refused to put any hairspray in. A girl has limits, ya know? "Oh, Sam, why on earth did I agree to do this?" I whined. She just smiled and shook her head. "Because you're an overachiever, honey. That's what you get for sucking up." Again, brutal honesty. She had a point. It was my fault I always got stuck with the crazy assignments. I vaguely remembered saying in my interview for the internship, "I'm your go-to girl. If you need a job done and done right, I'm the one to hire." It served me right. "Okay, I guess it's go time" I said before taking a deep breath, a quick look in the mirror and stepping out of the bathroom at the police station.

The chief did a decent job of quickly covering his shocked look with a cough. He started blushing and began stuttering through a description of the operation. I listened intently to his description, and waited patiently for him to get comfortable enough to look at me while speaking. "We've got um, a tow truck on call to take the guys' cars off when they're arrested and...um, the wagon will making runs back and forth a few times during the night to take the guys downtown..." He finally looked directly into my eyes, carefully avoiding looking anywhere else, and began giving instructions. "All you have to do is stand on the corner and make sure to smile at the guys driving by. I'm sure the Johns will initiate things with you, as bad as the area is getting now. When you're negotiating, we ask that you stay on the street and speak through the driver's side window instead of getting into the car. We'd hate for the driver to take off with you in the car and us not be able to get to you quickly enough. All you need to do is ask if he's ‘looking for a date.' If he says yes, make sure to ask him what he wants and how much he's willing to pay. This has to be clear. He has to explicitly say on record what the deal is so there's no question in court later. I'm sure you understand how that goes." I just nodded my head and tugged the hem of my dress down. I quickly decided never to do so again, realizing that as I tugged the hem down, the top of the dress shifted down as well. I gave myself a silent lecture to quit fidgeting and pretended I felt composed and self-confident, even though I didn't. "If you'll follow me," the chief said as he walked toward the door, "I'll give you a ride out to the location we've got set up. You'll be wearing a wire and there will be two officers working with you. The one who'll be listening to the wire is a rookie, but don't worry. The officer who'll be doing the arresting has been with us for a while and he'll be supervising." I nodded again, assuring him that I understood. I waved goodbye to Sam and followed him out to his cruiser.

Once on campus, the chief showed me to a small room that the officers had set up in. It was the break room of a maintenance building located near the street corner that was known to be a hot spot for prostitution. The room had a refrigerator and an old couch along one wall. Against the other wall were a rectangular table and a few chairs. "Hey guys," the chief began, "this is the intern that's helping us out today. " He turned to me, "Ma'am, this is Officer Keegan and Officer Warner." I was surprised to see that Keegan was a distinguished-looking older gentleman with salt-and-pepper hair, a strong jaw line, and a fit, trim body. His bright blue eyes had small lines at the corners, but were very alert. He stood, smiled and reached to shake my hand. I immediately noticed the calluses on his hand, but was also surprised by how gentle his touch was. I was relieved when I noticed that he didn't react to the way I was dressed. He just smiled warmly and nodded, saying "Don't worry ma'am, we'll take good care of you." I believed him and was comforted by his calm professionalism. I noticed the ring on his left hand and thought to myself that his wife was a lucky woman. Keegan moved to the side and Officer Warner moved forward to shake my hand. Warner was young, probably very close to my age, and absolutely massive. He towered over me and I noticed that his uniform was pulled tight across his chest, shoulders, and arms. His muscles weren't bulging, but he was still nicely defined and looked like he exercised daily, whether in the gym or on the job. He had dark, almost olive skin and big brown eyes framed by long lashes. His dark hair was buzzed short. He avoided my eyes as he weakly shook my hand, and simply nodded his head in reply when I said it was nice to meet him. I couldn't tell if he was extremely shy or extremely rude. Either way, I was a little irritated that he didn't even look at me when we were introduced.

The chief headed out to go back to the station and Keegan and Warner went back to setting up some of the equipment that was sitting on the table. "Hey Rookie, how ‘bout you start helping her with her wire? She'll need to be ready to go pretty soon." Keegan said over his shoulder. Warner gave Keegan a deer-in-headlights look. It was refreshing to see him actually react to something. However, while his nervous look made him seem more human and likable, it did worry me. I began to wonder what helping me with my wire entailed. Keegan smirked, but turned back to his work before Warner could see his amusement. I began to get skeptical. Warner picked up the wire and, muttering under his breath, motioned for me to come over to him. I walked over and he sighed heavily. I looked up at him quizzically and he looked down at me, into my eyes for the first time. The giant of a man actually looked scared. "Um...this wire needs to be taped...uh...under your ....clothes." I realized at that moment just how little of my body was covered by clothes, which meant an awkward situation was about to arise. I nodded and tried to think of a tactful way to get the wire taped under my skimpy dress without giving the officer a show. No ideas immediately came to mind. Blushing, I asked "Okay...well...how do I go about doing this?" Warner avoided my eyes and shrugged. Wow, you're a lot of help I thought. I rolled my eyes and started to unzip my dress in the back. Warner swallowed hard and glanced down, then to the side, then back down again. He handed me the wire without looking and turned his back to me. I took the wire and began taping it onto my stomach and chest with one hand while trying to hold my dress up with the other. I'm a patient person, but after struggling with the wire and my dress for a while, I eventually got fed up. "Okay, you're gonna have to help me a little. I can't seem to get the last part to stay in one place" I told Warner. Keegan spoke over his shoulder, without turning around "Yeah, it can get tricky. Why don't you help her out, Rookie?" I heard a slight hint of sarcasm in his voice. The situation was too ridiculous to get annoyed over. I just started to laugh, shrugged, and dropped the top of my dress, letting it fall to my waist. I figured that my red strapless bra covered as much as a bathing suit would anyway. Warner, still avoiding my eyes, turned around and reached to finish putting the wire in place. I noticed his hands visibly shaking, and he hurried through the process, jerking his hand back as soon as the wire was secured. "Thanks," I said, and pulled my dress back up, zipping it again and tugging it up, then down, then both up and down at the same time. I gave up, dropping my hands to my sides.

"Okay, all ready?" Keegan turned around to ask. "As ready as I'll ever get" I replied. Keegan glanced at Warner, who had retreated to the table and put on headphones to listen in on the wire. Warner nodded and gave Keegan a quick thumbs up. "Okay, hun, we'll be right here waiting. Just take your time and if you get nervous, don't be afraid to come back in." I took a deep breath, nodded, and walked out the door. Panic hit as soon as I reached the street corner. Oh shit, oh shit, oh shit...what am I doing?! I thought over and over in my head. Okay, just calm down. Just close your eyes and pretend you're out walking to work, just like normal. Of course, I would never usually wear something like this in public, but whatever...Now breath, just breath . I calmed myself down with the thought that this was just another job, just another rung on the ladder to success. I knew it was time to get to work, so I opened my eyes, pulled back my shoulders and stood with confidence. If I was going to stand on a street corner in a skimpy red dress, I sure as hell was going to look hot doing it. I started scoping out the cars that went by, and eventually mustered the courage to start smiling at some of the male drivers. It took a while, but sure enough one of the drivers slowed down and made eye contact with me. He pulled up to the curb. Okay, here we go... I plastered a huge smile on my face and walked up to the car. I was thankful I had put on the heels, as they naturally made my hips sway as I walked. As I approached, the driver rolled down his window. He was a younger guy, most likely a college freshman by my estimation. He smiled and raised his eyebrows at me, trying to be smooth and failing miserably. I almost felt sorry for the guy. "Well hey honey, are you lookin' for a date tonight?" I asked. "Yeah, I was hoping to have some fun tonight" he replied in a small, squeaky voice. "Oh really? Well what kind of fun?" I prompted. I placed my hands on the edge of the window and leaned toward him. Not only did this put my breasts in his direct line of sight, it effectively blocked his view out his window. He stared at my breasts, then his eyes moved up to my mouth. "I was thinking a blow job" he almost whispered. "A blow job huh? And how much are you gonna pay me for giving you head, baby?" I licked my lips after this statement and watched as his dick hardened, tenting his shorts. "50 bucks?" he said in a rush, obviously excited. I smiled, raised my eyebrow and nodded. "It's a deal" I said. Just then I heard officer Keegan walk up behind me. I quickly stepped out of the way. "Ohhhh shit!!" I heard the young man curse. I headed back toward the maintenance building without looking back and heard Miranda Rights being recited as I walked.

I stepped into the building, excited and a little relieved that I had actually pulled it off. Officer Warner looked up at me as I strutted in. He stared for a second, then nodded. "Good job" was all he could bring himself to say before looking back down at the newspaper in front of him. "Uh...thanks," I replied, and we waited in silence for Keegan to return so we could start the process again.

It got progressively easier as time went by. A football player, a fraternity boy being egged on by a few of his pledge brothers, and even a professor were all taken downtown to be booked. The pattern was simple: saunter up and ask what he wanted, move out of the way so he could be arrested. It was easy, and a little fun, really. Toward the end of the night, I could tell everyone was getting tired and was ready to go home. Keegan, while still talkative and amiable, had lost a little of the twinkle from his eye and Warner continued to be silent. I felt exhausted, between the high heels and all the smiling, I ached from my head to my toes. It also didn't help that every time I made a guy get hard just by talking to him, every time I heard one tell me what he wanted to do to me, I got a little wetter. I kept telling myself that these guys were creeps...that they were going to a prostitute for heaven's sakes, and that they shouldn't have an effect on me, except for maybe repulsion. But sure enough, I got a little thrill each time I walked up to a car, and felt disappointment when I had to stop talking to a guy so that he could be arrested. By the time the last half hour of the shift came around, I was completely exhausted, achy, and very , very horny. I couldn't wait to go home and slip between my sheets; I was so ready for a release. Last one I told myself. One last time, then I can go home, take off this dress and these heels, and slide my hand into my panties.... I stood up, stretched a little, and got ready to go out to the street one last time. Keegan had left the room, I had assumed to use the restroom, and it was just me and Warner. "Ya know," his deep voice startled me, as I hadn't heard it much before, "you are doing really well tonight. " I stared at him in silence. I think it was the combination of the aching feet and the sexual frustration I had felt all night, but I snapped. "Ya think?! I've worked my ass off tonight and you haven't said two words to me. This isn't exactly in my job description, but I'm still helping you guys out. Keegan was at least nice to me, and has actually been doing work. You've just sat on your ass all night. And even though you've got the easy job, you've still been in a shitty mood. You can't even look at me for more than a second without sticking your headphones back on and burying yourself in a newspaper or magazine!" I stopped ranting. I felt a little embarrassed about going off, but was too tired to care.

"Well what the hell do you expect?!" he returned loudly. He stood and took a few steps toward me. I realized then just how intimidating he really could be. "I've already seen you half naked because of that stupid wire. I can't look at your face because all I see is your red lipstick, and that makes me think about feeding you my cock. As soon as I look down from your face, all I see are your tits pushed up and almost out of your dress, so that makes me wanna bury my face between them. Then I look down from your tits and see your thighs and wonder what it would feel like if they were pressed against the sides of my head....and don't even get me started on what I think about when you turn around and I see your ass! Even when you're not in the room I can hear your voice, talking about blow jobs and fucking. Do you know how painful it is to have a hard on consistently for hours?! I have to distract myself or I'd explode!"

I was speechless. I had half expected some smart ass remark in return, or more likely still a shrug and some muttering under his breath. His vehement reply had shocked me, and I stood, trying to wrap my head around what he had said. Just as I had opened my mouth to respond, to apologize, Officer Keegan burst back in the room, cheerful and ready to send me back onto the street. He ushered me out the door, saying the sooner we got this done, the sooner we could all go home.

I stood on the street corner trying to process what had just happened. I should‘ve been concentrating on the cars driving by, but all I could think about was the officer who was listening to the wire taped between my breasts. Oh yeah...the wire... I looked down, peering down the front of my dress at the little black microphone. Should I really respond to him now? Or should I try to wait until we're alone together? I wondered. The thought occurred to me that we might not get the chance to be alone again. I decided to talk to him, but what should I say? I thought for a moment. I don't know if it was the fact that I didn't have to face him just then, or that I was dressed like a whore, walking the streets, but whatever it was, I felt a little bolder than usual. "Soooo, Warner," I began talking in a low, soft voice "I know you can hear me. I just wanted to say that all those things you talked about earlier...well, I've thought about them too." I stopped and smiled to myself, "In fact, I'm thinking about them right now." I began pacing again; looking around to make sure no one was watching me. "I'm thinking about your huge, broad shoulders, and how good it would feel to have my thighs resting on them, with your face in my crotch. I'm thinking about licking and biting down your chest, and taking your dick into my mouth and throat. But most of all, Warner, I'm thinking about you bending me over that table you're sitting at right now. Can you imagine that? Can you see me bent over right there in front of you, my ass out, ready for you to fuck me? I bet you can...and I bet your dick is hard right now, thinking about me." I stopped talking then, satisfied that I had made an impact. I was so wet thinking about him sitting there, trying to hide his hard-on from his colleague. I hiked up the bottom of my dress so it was just barely covering me, strutted to the street corner and began staring down male drivers. I wanted to get a guy as fast as I could, so I could return to the room where Warner sat, waiting. It didn't take long before a young, fairly attractive guy pulled over. I walked to his window, and he asked, "Are you dating tonight?" In two minutes flat Keegan was behind me ready to make the arrest. I hurried back up to the building and shoved the door open.

As soon as I walked in the door, Officer Warner crushed my body against his. His mouth engulfed mine and his tongue immediately pushed between my lips. His hand went up my dress and squeezed my ass so hard, it almost hurt. I moaned loudly into his mouth and spread my legs just enough for him to force his knee and thigh in between them. My prediction about him being hard turned out to be true...I could feel his hot, rigid tool pressed firmly against me. Warner's mouth moved down to the side of my neck and he sucked hard. I knew I would have a hickey tomorrow, but I didn't care. Just as he started to kiss lower down my collarbone and toward my breasts, I felt him shove me away from him and he moved quickly to sit at the table, pulling his chair forward to hide his excitement. I was about to scream in frustration when I heard the door knob turn. I had completely forgotten that Keegan would be returning to the room. He walked in to the silent room, glanced from Warner's back to my face, gave me a quizzical look, then shrugged and started gathering his things. "Hey Rookie, can you pack this stuff up for me? I'm gonna head out, the wife's wanting me back soon" and with a smile and a nod in my direction, he left without waiting for an answer.

Immediately, Warner stood. He didn't rush toward me as I thought he would, but stood in front of me, wide-eyed with his dick straining the pants of his uniform. He slowly undid his belt and laid it on the table beside him. Then he looked into my eyes and, with a crooked smile, began to very slowly look down the length of my body, reveling in his new freedom to stare as much as he wanted. His breath became ragged as his dark eyes traveled over my mouth, neck, and breasts. Finally, he dropped his intense gaze to the place where my dress ended, licking his lips. His hand reflexively went to his crotch, rubbing himself firmly through his pants. After a while, he tore his eyes away from my slightly parted thighs and looked me square in the eye. He walked over very purposefully, picked me up, strode over to where he had been standing and practically dumped me onto the table in front of him. He quickly stepped between my thighs and began kissing me with same intensity he had before. I could feel his large, strong hands unzip the back of my dress and push it down. He unhooked my strapless bra effortlessly, pulling it completely off and tore the wire from my body, dropping it carelessly on the table beside us. He groped my tits and began to squeeze my nipples, rolling them lightly between his thumb and forefinger as he broke our kiss to sink his teeth into the side of my neck. He slid his hands from my tits down my sides to my hips, which he roughly jerked forward so that my panty covered pussy was grinding hard against his tool.

He brought his mouth up from my neck and began whispering in my ear, "I'm gonna fuck you. I'm gonna bend you over this table and fuck you hard till you cum on my cock. But I wanna taste you first. Would you like that? Do you wanna feel my tongue on your clit, you little whore?" All I could manage to do was moan loudly and wriggle my hips, grinding harder against him. I had never been this wet before, and I knew it wouldn't take much to make me cum. He pulled away slightly, grabbed the chair he had been confined to all night, and sat down, his face even with my pussy as I sat on the table in front of him. He pushed my thighs wide apart; my dress was already gathered up at my hips. He leaned forward and pressed his face against my panties, breathing in my scent. He groaned loudly and began to kiss and gently bite through the material of my underwear. I felt his tongue slide just under the lacy edge of my panties. "Oh god, oh god, oh god" I chanted, completely lost in the heat of his mouth on my pussy. My whole body was shaking and my knuckles were white as I gripped the edge of the table beneath me. "Please, Warner!" I begged, "Please, take them off, I wanna feel your mouth." He looked up and smiled, a wild look in his eyes. He pulled my panties down and off, tossing them aside. I put my hand on the back of his head and pulled him toward me. He leaned forward and put my legs over his shoulders and soon I felt his wide, soft tongue as he slipped it between my pussy lips. I tipped my head back and moaned loudly and I felt his tongue move slowly up and down my crease, finally settling on my swollen clit. He began to lap his tongue lightly over my clit, occasionally sucking gently. He shifted and I felt his finger start to enter my body. I was so wet that it slid in up to his knuckle easily. He rhythmically pushed his finger in and out of my body, keeping the same slow pace with his tongue. I knew it wouldn't take long, and soon I was screaming each time his tongue flicked over my clit. He picked up the pace, sucking hard on my clit and finger-fucking me hard and fast. Soon, I came, convulsing and bucking my hips as my muscles squeezed and released his finger over and over.

Finally, I felt myself come down from my orgasm. "Oh my god! " I panted, "That was amazing!" I reached down, took his face between my hands and pulled him up to kiss him full on the mouth. I could taste myself while I kissed him, which only served to turn me on more. He stood up and began to unbutton his shirt, pulling it off and letting it drop. He quickly pulled his undershirt over his head and I moaned and stared at his massive chest and defined abs as he unbuttoned and unzipped his pants, pushing them and his boxers drown to his ankles. Without ceremony, he picked me up off the table, put me on my feet, spun me around and pushed my shoulders down so I was bent in half over the table in front of him. He yanked down my dress and I stepped out of it, spreading my legs for him. For the second time that night, I was thankful I had worn my highest heels. It felt so wonderful, being bent forward with my ass and pussy so exposed. I felt Warner's hand squeeze, then lightly slap my ass. "Mmm, baby, are you ready for this big dick? Do you think you can handle it?" he groaned as he allowed the tip of his dick to slip in between my pussy lips, sliding it up and down, but not pushing in. "You're so fucking wet...I can't wait to feel your tight little pussy squeeze my dick like it did my finger." He began to push forward, and I felt his dick start to sink into me and fill me up. I couldn't help but moan as I felt him enter and stretch me. "Fuck me, fuck me, fuck me...." I murmured, and I began to move my hips back and forth, willing him, begging him to give me his entire length. Finally, I felt him hit bottom and his hands gripped my hips tightly, forcing me to keep still. He stood still for a few moments, just enjoying the feeling of his cock surrounded by the wet warmth of my body. Then, without warning, he pulled back until only the head of his dick was inside me and slammed forward, making my entire body jerk forward with the force of his thrust. He grunted and started to slam into me again and again, pulling far out each time before thrusting in to the hilt. He wasn't going fast, but was fucking me so hard that the table in front of us crashed against the wall with each of his thrusts. I felt his left hand move to my breast, groping and massaging it as his right hand moved down. He starting fucking me faster and I felt his fingers move to rub light circles over my clit. He groaned loudly and continued his assault on my pussy and clit. I felt his cock get harder and bigger and he started panting heavily, "Oh shit, I'm gonna cum soon...are you ready? Are you ready for my cum?" He grunted and rubbed my clit faster and harder. I felt myself getting close, and soon I was convulsing again, completely lost in the best orgasm I'd ever had. "Oh fuck, baby, that's it...cum on me.....oh fuck, oh fuck, I'm gonna cum!" he yelled as he slammed into me one more time and stayed buried deep inside me. I felt his cock pulse and his cum start to fill my pussy. There was so much that it overflowed and began to run down the back of my legs and inside of my thighs. He stayed deep inside me for what seemed like forever.

Finally, after several moments, I felt his softening cock slip from my body. He was panting heavily and I could tell he was exhausted. He moved back a little and collapsed into the chair behind him. I turned around, leaned down and kissed him lightly on the lips in thanks. Just as I was about to ask him back to my place, I heard the door knob turn. We had been so lost in each other that we hadn't heard the car pull up. I heard the door open and Officer Keegan say "Ya know, I got all the way downtown before I realized I forgot my..." He stood in stunned silence as he took in the scene before him. Warner was sitting in his chair with his pants at his ankles, panting heavily with sweat on his forehead. I was standing with nothing on but my high heels, my hair disheveled, red lipstick smeared, and Officer Warner's cum dripping down the inside of my thigh. "Damn, Rookie...." was all he could say.