Undercover Undone (Closed)

[AnnieD]

*** Out of character ***

Spoiler alert; this thread will involve some drug/alcohol abuse and some really rough, depraved sex. If this isn't something that interests you, please don't read further. If it does, well enjoy the show!

Of course, everybody in this story is fake, not real, part of my twisted imagination, etc. Everybody that matters is over 18 and adult.

***

My character:

http://i.imgur.com/3Wm2O8s.jpg

Name: Amy Rodriguez
Age: 24
Height: 5'10"
Cup size: 38DD

...​

Some background:

Amy Rodriguez is a twenty-four year old with a bit of a fierce personality. While this has helped her over the years, she quickly finds herself biting off more than she can chew. Desperate to infiltrate the notorious Tommy Milroy; a lewd, disgusting pervert who preys on college girls, she's willing to put herself in the cross-hairs of this man.

Tommy, however is expecting this and wouldn't have it any other way.

Story/IC:


Student Union: 1 PM:

"Are you fucking serious?!"​

Okay, maybe I was being a little harsh but truth be told, I was a little offended. Steve, the student union leader for the School of Journalism here at the University of Columbia was a little shaken up from my little outburst. I hated to be so hot-headed, but the fact of the matter was that I was mad over the fact that he didn't think that I was capable of doing a story. Still, seeing him so nervous because of my actions made me feel a little ashamed.

"I told you, it's not that simple. Women are his targ-"

"You don't think I can handle myself?" I asked, walking up to him. "I come from the Bronx!"

"It's not that, I - "

So, the story? Well, there was a scummy man who owns a few shady nightclubs and bars across Brooklyn and Manhattan. The issue doesn't come from these businesses, but for the fact that this man, Tommy Milroy, was a fucking pig. There was no easy way around it; the man was a lewd, disgusting mess that preyed on college girls. The story would be for one of us to infiltrate this circle and find something illegal that he might be doing. From there, we could bring his seedy life into the light and possibly get him charged for something.

"It's just that he already has his eye on you, Amy."

...

Home: 4 PM:

I was angry. Sure, this man had his eye on me already but so what? I mean, I was already used to lewd, disgusting people commenting on me and 'having their eye on me'. What a joke.

I mean, most of it had to do with my social media accounts (which like many young women, puts me out there) and my body. Okay, not to sound like I'm completely full of it, but I do have a sexy body. I'm tall (5'10") and I have that hourglass body shape, complete with 'child bearing hips'. I'm a bit on the busty side, having 38DD cup breasts and what really gets guys going is my big round ass. Yep, it was big; not obscenely fat or anything, but more than a handful.

http://i.imgur.com/A74RU1t.jpg
"Just posted this. Yes, this is the type of picture I put up. What? I liked to have a wild personality..*******."​

I eventually gave up and drove back home to see my boyfriend - who I lived with.

First thing that I did when I got back home was take a nice warm shower. I had to take my time, taking off my fake piercings, peel off my tattoos and staying in the shower long enough to calm down...Oh, right.

Remember how I said that I was from the Bronx? Yep, I never got too specific from that - I was from Riverdale. It was technically part of the Bronx...just one of the most upper-middle class neighborhoods in New York and one of the lowest crime rates in the city. I just left it at the 'Bronx' because that gave me some authenticity than anyone else studying Journalism at Columbia. These fake tattoos and piercings? Same deal. Honestly, I started this appearance for my Instagram account and it sort of got out of hand.

Eventually, my boyfriend came home and I greeted him with a soft kiss. His hands, greedy as they were, slowly reached behind my back and attempted to grab my towel covered ass.

I slapped his hand.

Did he ever grab my ass? No. Did we have ever sex? No.

Okay, another confession. I was, believe it or not, a virgin. Yep, that's right. Sure, I lived with my boyfriend but this wasn't a life of sin. Simon and I just happened to be together since high school and we went to the same school (well, except he studied law and I studied journalism). We were engaged, sure, but I wasn't about to have sex with him until we were officially married. Hell, we haven't even seen each other naked. We didn't even sleep in the same bedroom.

"How was your day babe?" he said with a smile, going towards the kitchen.

"Ugh...let me tell you all about it."

So, I went on to tell him what happened earlier at the Student Union room and how much injustice was caused by Steve. He nodded and listened but...he didn't agree with my point of view.

"Babe, if he thinks you're in danger, why do it?"

...

Home: 9 PM:

So, this brings me to my current predicament. I was so fired up from Steve and Simon that I actually put my make up, piercings and tattoos on and contemplated going over to one of Tommy's nightclubs. I knew where he was going to be tonight, hell I knew that I'd be able to get in with no problem. But as I put on the tiny, small fake camera on my blouse, came a bit of anxiety.

What if they were right?

With some minutes to stop and think, I quickly found myself putting on my jeans and heels. I was going to go. I needed to put an end to Tommy Milroy, whether my boyfriend or boss liked it or not.

 

[The_J0k3R]

Another night surveying my clubs, another night watching the money roll in.

Such was the life of a gangster these days. You had to have a front, you had to have security, you had to pay off the right cops to make sure everything kept moving smoothly. I had mastered this fine art, and that was how I had built my empire.

My bouncers knew every cop in town, by face. Only the ones on my payroll were allowed inside my clubs, and they were given all-access passes to enjoy the “extras” that were offered behind closed doors.

I also knew every hot piece of instagram trash in town. That was a recent phenomenon. Hot chicks liked to show off their bods on the interwebs, and there were plenty in New York. I had a fucking database going, always scouring instagram, twitter, tumblr, facebook for the hottest new piece of ass that could be seen in my clubs, dancing her hot little butt off, high as a kite on… Well, whatever.

So when that hot little tattoo’d alt-girl, Amy Rodriguez, showed up, I was there, ready for her. She was an interesting case. Wanted to be a journalist or some such bullshit. With a body like that, there was only one thing she really needed to do: lay back and spread them legs fucking wide.

Me and my huge fucking cock would be teaching her that lesson soon enough. There she was now. I had instructed my bouncers to let her in as soon as she walked up.

I couldn’t wait to meet her.

 

[AnnieD]

I wasn't sure what to expect when I stood outside the club.

The line was huge, but the building itself well...it looked like garbage. You know of those buildings that were a factory back in the day? That brutalist, plain colored exterior? Well, the nightclub looked like one of those buildings from the outside, but seeing as it was getting dark out, I guess that didn't matter to much of these people. I took a breath breath as I walked in front of them, putting on my glasses on to look 'professional.'

"Name?"

"Amy Rodriguez. I think Tommy is expecting me?" I bluffed.

Truth be told, I knew that Tommy was a pervert with his eyes set on me, but I wasn't so sure that he planned so far ahead to have me in his list. Thankfully (or unfortunately) I was right and the bouncer wordlessly moved aside and let me in. I guess that I was dressed pretty damn well, because I could feel the bouncer's glance go my way, probably fixated on my denim covered behind, as I walked in and admired the lights and loud music. There was even a huge LCD screen hanging above, with all sorts of clips playing.

And there I spotted him. Tommy Milroy.

The man was in his mid 40s and had that sleazy look. He was probably an inch or two taller than me, rough stubble across his face and a shabby physique. By that I mean that he obviously used to be in shape...but maybe not as much anymore (I think I saw hints of some belly, but I wasn't too sure from this distance).

Well...I guess that I should say hi. I sure hoped that this small camera (hidden on the button from my blouse) worked.

"Hi." I said with a fake smile, moving on to him. "Tommy Milroy, right?"

 

[The_J0k3R]

The radio piece in my ear kept me informed of everything going down in my club, and Amy’s arrival was no different. The bouncer always informed me when one of my targets had arrived. I made sure I was close to the entrance.

The tattoo’d, redheaded vixen was hard to miss, even if she was trying to appear “professional”. She immediately approached me, and I had my eye on her the whole time, greedily taking in her luscious curves. She was a beauty, that was for damn sure. She’d make a fine addition. She came up to me and asked if I was Tommy Milroy.

“That’s right,” I replied, holding my hand out to shake hers. “And you are… Amy Rodriguez, right? Local Instagram fitness hottie, as I recall. Your pictures online don’t do you justice.”

I looked her up and down again. “Neither does that outfit. Next time you come to my club, wear some proper clubwear.”

 

[AnnieD]

Arrogant as I've heard, Tommy gave me that look. A look that basically said 'I'm in charge here. What of it?". I watched him as his eyes scanned my body; going from my high heels to my face. I felt a bit disgusted over how quick he was to objectifying me, even before we've had a proper conversation.

“That’s right,” he replied, reaching his hand out to me. “And you are… Amy Rodriguez, right? Local Instagram fitness hottie, as I recall. Your pictures online don’t do you justice.”

So, he really did know about me? God, that was worrying and...just a little bit flattering, I guess.

“Neither does that outfit. Next time you come to my club, wear some proper clubwear."

"Oh?" I asked, trying to be as oblivious as possible. Maybe this would be great for my evidence for the news piece. "And what's wrong with what I'm wearing?"

 

[The_J0k3R]

“Look around,” I replied. “Everyone here looks good. Sharp. For example,” I said, reeling in two passing young ladies in tiny tight dresses. “Now, this is appropriate club wear,” I said, placing an arm around each of the girls. “Lookin good ladies,” I continued, and they giggled, kissed my cheeks, and I gave them each a little swat to the butt to send them on their way.

I looked at Amy. “So what brings you here tonight, Miss Rodriguez? It’s clear you didn’t come for the party.”

 

[AnnieD]

I watched as those two young women, maybe a year younger than I was, pass by and get hassled by this pig. I was almost in horror, seeing how he objectified them so easily; as if it was a normal occurrence for him. Why were they okay with this? I couldn't imagine any reason why a girl would put herself in this situation where they're fine with getting pulled in like that and giving a swat on their butt like it's a common way to say good-bye.

“So what brings you here tonight, Miss Rodriguez? It’s clear you didn’t come for the party.”

"Well, I'm just here to give the club a review." I said with a smile. It's obvious, with my glasses and my attitude, that I wasn't here to have fun. But I didn't want to make it too obvious that I'm looking for some dirt on him. "Apparently your clubs are pretty big on campus."

 

[The_J0k3R]

“A review, huh?” I said. “Well, let me show you around a bit. First, though, let’s get you a drink. The least you could do is try and fit in,” I told her, eyeing her outfit again.

“Please understand, I’m not trying to be rude, but we have standards. You walked right past a lot of girls who were in line, who spent a lot of time and money on their appearance and outfit, and then they see you waltz in wearing jeans? Doesn’t exactly send the right message.”

I guided her over to the bar, and a signal to the bartender was all it took to have two drinks delivered very quickly to us. A beer for myself, of course, and something fruity and bright red for her; a very potent beverage, but the alcohol content was very well masked. It was with a deft, quick slight-of-hand move that I poured a small vial of a special drug into her drink.

I handed her the drink as I took a swig of mine. “You’re right, though. The college students do seem to enjoy all we offer here.”

 

[AnnieD]

“A review, huh? Well, let me show you around a bit. First, though, let’s get you a drink. The least you could do is try and fit in,”

"Yeah, sure." I replied a bit unenthusiastically.

Oh great, he was planning on getting me drunk. Well, that wasn't going to work - I have a strict three drinks policy whenever I go to a place like this and I never loose sight of my glass. You might think that I'm being a little paranoid, but it pays to be when you're dealing with someone like Tommy Milroy.

“Please understand, I’m not trying to be rude, but we have standards. You walked right past a lot of girls who were in line, who spent a lot of time and money on their appearance and outfit, and then they see you waltz in wearing jeans? Doesn’t exactly send the right message.”

"What message is that?" I asked curiously, trying not to pry too much but enough to get something. "My boyfriend thought that I looked great tonight." I then added, trying to get the message across that I'm taken.

He led me to the bar, a bit away from the crowd (although there were still quite a few people around) and two drinks were delivered to us. I saw that he got himself the beer and me this...fruity drink? Well, if I wasn't paying...

“You’re right, though. The college students do seem to enjoy all we offer here.”

I took a sip from my drink. It actually tasted pretty good; you know, a bit like fruit punch with just a hint of bitterness to it. I placed the glass down as I answered "I can see that. This place is packed."

 

[The_J0k3R]

I watched her take a drink from the doctored beverage, and smirked. “Yes, the place is packed. It usually is. See the girls dancing in the cages?” I asked, directing her attention to the scantily clad girls performing several feet above the crowd. “You’d be perfect for that job, with your body.” The cages were just high enough that people could reach up and leave cash tips on the bottom.

“They are all college girls, and they make some very good money,” I explained. “Perhaps we could arrange a private audition? I’d love to see how you grind that big butt, in person. Your videos on instagram are proof enough you know how to move. Those girls cover all the costs of books and room and board just working a couple nights a week. And the benefits package is… extensive.”

 

[AnnieD]

“Yes, the place is packed. It usually is. See the girls dancing in the cages?”

I glanced over to the direction of some barely covered women dancing, on a cage right above the crowd. I was horrified of the thought of women having to do something so...disgusting for the enjoyment of a bunch of perverts. I was shocked as he added “You’d be perfect for that job, with your body.”, thinking for a moment that I'd even go along with that.

"Yeah....no." I replied, looking away from the lewd display.

“They are all college girls, and they make some very good money,” he continued “Perhaps we could arrange a private audition? I’d love to see how you grind that big butt, in person. Your videos on instagram are proof enough you know how to move. Those girls cover all the costs of books and room and board just working a couple nights a week. And the benefits package is… extensive.”

Grind that big butt? Who gave him the right to talk about my body like that? Still, I tried to entertain that thought...being dressed in barely anything, showing off my body to a bunch of men...well, while it might be fun for some people, it wasn't for me. "No thanks, but thanks for the offer I guess." I said with a bit of a chuckle, taking another albeit larger sip from my glass of alcohol. "...But you'll never see me grind my big butt." I added with just a hint of playfulness.

Why was I being playful? Well...

Uh...

That's a good question.

 

[The_J0k3R]

“Well, that’s a shame,” I replied. I nodded towards the entrance to the VIP area. It wouldn’t take long before Amy recognized a number of celebrities on the other side of the glass wall, raised up above the common club area.

“That’s the best way for a girl like you to get invited back to where the real party happens,” I explained with a little smirk, taking a drink off my beer.

“Now, if you’ll excuse me, I have some other guests to attend to.” I nodded towards a nearby bouncer. “And since you’ve failed to meet the club’s dress code, Brutus here will be escorting you out now.”

Brutus certainly lived up to his name, a hulk of a big black man, easily six foot eight and pure muscle. “Miss?” he said, his hand motioning towards the door.

 

[AnnieD]

“Now, if you’ll excuse me, I have some other guests to attend to. And since you’ve failed to meet the club’s dress code, Brutus here will be escorting you out now.”

"What? Are you serious?" I asked with anger, my body all shaken up over how he was going to kick me out. Seriously? Me? And supposedly he had his eye on me. The bouncer then came to me and with a simple "Miss?" he escorted me out of the club. Just like that, my investigation was ruined and I was forced to take a walk of shame past the line of people waiting.

Unbelievable.

I showed up home at about 10:00 PM. Simon was off at the library, cramming for another exam so I had the house to myself at the moment. But, with all the excitement (and lack thereof), I felt like hitting the hay. Maybe I could figure out something tomorrow to ruin Tommy. That arrogant...cocky...

...

"Tommy? What are you..." I said, in just a thong and a bra. Tommy, the sleazy pig of a man, came up to me and kissed me full on in the mouth. I squirmed against his grasp, his hands moving down my back and to my ass. His hands, squeezed hard on both cheeks to the point where it hurt. But it wasn't the painful kind of hurt. No, I barely even recognized the pain. It was...pleasurable.

"Mmmph" I groaned as his tongue forced its way down my throat and he pulled me in closer.

"Amy?!" Simon shouted from the other side of the club "What are you doing?!"

All I could do for a reply was pant as Tommy sucked on my tongue, in front of people...

...

I jumped out of my bed in an almost cold sweat. Jesus Christ.

I looked around my room, almost in complete disbelief of my dream. I know, it sounds absolutely ridiculous that I'd look around my room, as if someone would be able to see my dream, but I was in that half-asleep state that people are normally in after a messed up dream. God...

...

I should probably go on my computer.

I put on my glasses, which I set aside the bed when I passed out. Opening my laptop, I searched my emails in hopes that I'd get something from Tommy. Maybe about a club invitation or what have you.

...Nothing. Damn it.

I leaned back on my office chair and I wondered what I could do in order to get invited to the club again. It'd be great to see him again...for investigation purposes, obviously. Then I realized that this creep added me on Facebook not too long ago and I could use this.

So, I messaged him:

"Hey Tommy. Sucks getting kicked out of your club lol"

Stupid? Sure. But it was my best show at getting in again.

 

[The_J0k3R]

The chat notification popped up on my screen as I was busy getting a blowjob from one of those lovely dancing girls. She was high as fuck on a serious dose of the same stuff I had slipped Amy; albeit, Amy’s was just a taste of the stuff.

I checked the message. It was from Amy. Social media was a beautiful thing. She was whining about me having her kicked out of the club.

I typed a message back as the blonde bobbed her head up and down in my lap.

Can’t wait to see you back in there, now that you know how to dress properly. A tight little dress to show off all that ink and those curves would get you a spot at the front of the club web site

If those instagram whores loved one thing, it was attention, and being featured on the front page would probably double her following…

 

[AnnieD]

"Can’t wait to see you back in there, now that you know how to dress properly. A tight little dress to show off all that ink and those curves would get you a spot at the front of the club web site "

That was his reply and I sat there for a moment, reading it over and over again.

Obviously he wanted me over at his club again...but only if I dressed the way that he wanted. A tight little dress? Well, that wouldn't really do - mainly because I only wore dresses for special occasions and going to this club definitely wasn't a special occasion for me.

I thought about it and against my better judgement I added:

"What about shorts? Would that work for you? "

 

[The_J0k3R]

Shorts? She wanted to wear shorts? I shook my head. This girl was something else. What was she up to? Why was she so interested in the club, but didn’t like clubwear?

Frankly, something wasn’t adding up. I’d figure it out in due time. In the mean time, I was going to keep her close… and have a little fun with her.

The blonde was starting to suck my dick with quite a bit of enthusiasm. I sent a message with a gif back to Amy.

Something like this?
http://67.media.tumblr.com/9bd7035ffb6f42b11728730aec981f72/tumblr_o4odv3Eisi1tfmwtwo1_400.gif

 

[AnnieD]

Okay, maybe I needed to get a little more flirty. I didn't want to be be too stiff with him, because hey - I needed to get in that club. So when he showed that .gif image, I took a while to respond. I wanted to tell him that there was no way in hell that I'd wear something like that but...I needed to. Still, I didn't have anything too revealing like that except for a pair of booty shorts that I sometimes wore to bed.

Oh. Great.

"How does a pair of booty shorts sound? " I typed in "I figured that it may be nicer for the club rather than a stiff dress."

 

[The_J0k3R]

I smirked a bit as I looked at her message eventually come across my phone. The blonde was still lustfully sucking away on my dick, licking my full length from balls to tip and jerking it. “That’s it, slut, work up a nice big load to swallow down,” I encouraged her.

I sent a message back to Amy. “I’ll consider it. Would certainly make it easier for you to shake that fat ass on the dance floor!”

I had no intention of making it easy on her, of course. My plans for her were growing in my head…

 

[AnnieD]

“I’ll consider it. Would certainly make it easier for you to shake that fat ass on the dance floor!”

I chuckled a bit at this comment. Did he really just comment on my ass? I leaned back and looked down, admiring the own curvature that my cheeks made as I sat down. I turned back to the computer screen and I thought a response, deciding to have a little fun with this.

"Shake that fat ass? I don't have a fat ass! " I replied back and waited a response.

 

[The_J0k3R]

I chuckled at her feigned indignation at my comment about her ass. I was typing with one hand now on my phone, as I had the other wrapped in the blonde’s hair, using her mouth as my own personal jerk-off sleeve.

I’d have to get my hands on that ass to determine just how much is fat and how much is muscle I wrote back.

 

[AnnieD]

"I’d have to get my hands on that ass to determine just how much is fat and how much is muscle "

Did he really think I'd give him a chance to feel me up? As if. I thought about my next comment; wanting to sound playful but not as if I was easy or anything. So, I went on as to tease him "What? My butt is tiny. ". Obviously, I knew better but I figured that a little flirting and playfulness wasn't going to bring about the end of the world.

 

[The_J0k3R]

I grew a bit frustrated at her teasing response, and took it out on the blonde, forcing her face down firmly on my cock, which was more than long and thick enough to completely fill her throat. She smacked me in the thighs a few times, but I had grown bored with her and so held her down on my cock until she passed out from lack of oxygen, and then pulled myself out of her face and let her collapse in a heap on the floor as I began sending a message back to Amy.

“Tiny? Compared to what? An elephant?” I shot back, fully aware that it was kind of a mean statement, but let’s face it: I wasn’t exactly known to be a nice guy. I continued my message: if you want to get into the club in booty shorts, you better have a lot of cleavage on display. And you’re gonna have to be my girlfriend for the night.