The Intentional Cuckquean Ch. 02

I sat in my office chair thinking about Madison, probably too much. I knew she was clearly after Taylor and her parents. I couldn't make out whether she was just mad at me invading her personal life or jealous of how I had dressed in front of her husband. All things I intended to figure out with her as my obsession was growing.

"Chrissy, Madison will be here soon and I want you to greet her. Let's get you prepared, come over here." I told her. Chrissy came over from her desk wearing her normal skirt and blouse, swaying her tiny hips.

I lifted her skirt to reveal her beautifully bald pussy. I skimmed the surface of her stomach, downward along her lips and up the center of her slit. Her lips parted slightly as I did this. I pulled out a remote control vibrator that I used to edge her and rubbed it against her opening. It got a little slick, but I didn't have that much time until Madison was here so I told her, "Open your mouth, we need this wet enough to get into your fuck hole."

Chrissy opened her mouth immediately and I probed the vibrator around her mouth, making sure she slobbered all over it. I then took it out and put it back into her cunt, which accepted it readily given how slick it was. I pushed it up until the small red remote cord poked out slightly and pulled her skirt back down. On my phone I started the vibrations on a low setting, which I could see Chrissy visibly move to upon initiation.

Chrissy returned to her desk and blankly stared forward as I increased the vibrations a notch. "Tell me Chrissy, do you like when I put things in your cunt?" I asked her. "I like it if you like it ma'am." she obediently replied. She had learned how to respond well. I increased the setting to intermediate and saw her arch her back up and open her mouth again.

"Rub your clit too, but no cumming." I commanded her. Chrissy put her hand down to her skirt and lifted it to allow access to her clit. She rubbed it slowly in circles, closing her eyes and cocking her head back.

I saw in the parking lot Madison pull up and got up from my chair. "I'm going to the back for a few minutes, I want you to greet Madison and have some small talk while I prepare a few things." As I got up I increased Chrissy's vibrator to high, which made her eyes bulge and elicited an audible gasp.

I went to the back room and could see slightly through the door. I wanted to set the power dynamic with Madison to make it clear I wasn't her highest priority and that she had to go through my assistant. For Chrissy, I just loved messing with the poor slut.

"Is Brooke here?" Madison blurted out as she opened the door.

Chrissy was starting to sweat from the vibrator humming away inside her cunt. She stayed seated and struggled to form a response, "Sh...she's getting a few things organized...how...how are you doing?"

Madison didn't respond, so I increased the setting to the maximum. Chrissy let out another gasp.

"Are you okay? Are you sick?" Madison said looking down at Chrissy, who was sweating and trembling.

"Ohhh, I'm fine. How is your dayyyy?" Chrissy said dumbly.

"Can you fucking get Brooke!" Madison stammered.

At this point I decided to come out, but left Chrissy's setting on high.

"Oh, hi Madison! Great to see you. I hope Chrissy received you well!" I said effusively.

"She's weird. There's something off with her." Madison said bluntly.

"She just gets intimidated by beautiful women." I said, trying to build up Madison's ego. Come with me to my desk, I have a bit of info to share. I softly touched Madison's shoulder, which she noticed and looked at me.

Guiding her to my desk I bent over it showing off my cleavage, which I caught Madison eyeing. "I think her and the family are on a boat, that left from Florida." I told her.

There was some silence and then Madison said, "That's it? I came all the way down here for that? What boat, where did they go?"

"I have an idea which one. I'm confirming it with a broker that I know. However, I don't just give out information to strangers. I want to get to know you better. I want to learn why you are searching for these people and if it's all legit, then I'll help. I suggest I come over to your house for dinner this week and you tell me all about it."

Madison paused, clearly thinking of her options. This women was extremely calculating I could tell. She reasoned that it wouldn't be too bad to have me over and responded, "Okay, Friday evening, I'll text you the address for 7pm."

Chrissy at this point was visibly shaking, which Madison looked at she turned to leave. "What the fuck?" Madison mumbled as she left.

"Chrissy, dear, before I let you cum I want you to write a few things down. We're going to dinner Friday night and you are to look like a bundle of sex. Make sure you wear that micro black dress we bought for you for the Butterfly Cage."

"Yyyessss, ma'am, butttt...you want me there? I thought you were into her." Chrissy stuttered ready to cum.

"So cute, trying to think by yourself now are you? You see, Madison is definitely hiding something and I need time with her separate from her husband that she clearly doesn't care about. You are going to entertain him and also let me know if there's something I'm missing here. Okay, rub your clit now and get that little pussy off!" I commanded.

"Ffffuccckkk! Yessss!" Chrissy squealed as she came instantly.

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The week went by uneventfully and it was Friday faster than I could have wanted. I was at my home getting dressed in nothing special, save for a little cleavage that I showed during Madison's earlier visit. She would definitely be confused by this as my original intent was to go through her husband, but after feeling that out I got the sense it wasn't the right move.

Chrissy on the other hand was oozing sex. I looked over her petite little body. She wore a skin tight black one piece dress that wrapped right up to her butt cheeks. Any slight bend and it would inch up to reveal her pantiless crotch. Her tits, while not very big, were almost bursting out of the top that cut straight down, nearly to her navel. I had her curl her long blonde hair that skimmed against her ass.

"Put the 5-inch stilettos on," I told her. "God you look like a whore. Well, I guess you basically are tonight, but no taking any cash!" I said as I laughed.

We arrived at Madison's house and rang the bell. I wasn't sure what to expect, but wasn't too surprised to see Madison answer the door in a drab, ankle length skirt with an apron.

"Hi...wait, what is she doing here and god, what the hell is she wearing?!" Madison exclaimed.

As I responded, "Oh, I didn't realize you thought it was just me coming?", Richard emerged and added, "the more the merrier, welcome!" He looked me over, but couldn't stop staring at Chrissy.

We walked in the all too familiar house that I was peering into the other day. Very neat, modern, and nothing remarkable. However, the dynamic between Richard and Madison was...tense. We headed to the living room where Richard directed me to a chair and Chrissy to a small sofa. He then gave a soft, but stern command to Madison in Russian, which she didn't look pleased by, but accepted.

"What would you ladies like to drink?" Madison asked in an awkwardly non-sincere way.

Both Chrissy and I asked for champagne, but Richard interjected when Chrissy ordered, "My dear, you would love the martini Madison's makes. Have that instead." He then proceeded to sit right next to her on the sofa, virtually leg touching leg.

"So, Madison tells me you've been helping her with one of her little side projects?" Richard asked.

I really didn't know what to say as I wasn't sure what Madison was up to, so I improvised, "Yes, she's been coming by my travel agency recently and we really connected well."

The chit chat continued for some time, Madison brought the drinks and sat in a chair on the far side of the room. We migrated eventually to the dinner table, where once again Madison was ordered around in Russian by Richard.

While she was in the kitchen I asked him, "So, you both speak Russian, what's your connection?" As Richard ogled Chrissy, who was now looking tipsy finishing her second martini.

"Hah, "connection"? I grew up there when I was young. My family has a number of businesses, mainly in import and export, but I wanted to get out of the country at a young age and there was a dental school exchange that led me here. I met Madison here who had few connections, particularly with her parents dying at an early age." Richard stated.

This began to fascinate me so I probed, probably too directly. "So, "import and export", sounds like the mafia to me!" I chuckled. Richard looked at me very directly and said, "My family does what it takes to be successful." He paused, looked at Chrissy and then said, "Dear, your cheek seems puffy. When was the last time you had an oral exam?" Chrissy not understanding how ridiculous the statement was, touched her cheek and responded, "Oh, it's been a bit." Richard got up and put his hand out saying, "Come with me to my office, I can help you." Chrissy took the much larger man's hand, which moved swiftly to her far lower back as they went away.

Madison returned, "Where did they go?" "To the office." I responded dryly. "Oh...figures," she said, somewhat expecting that. "Well, now that they are gone let's go to my "office"" Madison said. I followed her to the other side of the house where there was a cubby area with a computer.

She went into a full story about Taylor being a close friend that she thinks something bad happened to and that her disappearance wasn't being taken seriously by the police. I could tell she was lying and let her go on and on. I had my own agenda, taking out one of my promotional travel agency "pens" to write things down. These pens were special as they had a small microphone that connected to my phone. While Madison was going on and on I slipped one in her purse and left another on her desk. At some point I would be able to get the real story.

"So...?" Madison asked me. I hadn't been listening and looked blankly at her. "Which boat are they on?" I pushed her off by stating, "I'm getting confirmation from one of my brokers, who should have something later this next week."

"Fuck, I need to know!" she said as she got upset. This seemed like a good time to ask some deeper questions, "You seem really tense, we'll get the info, don't worry."

Madison seemed to break from her anxiety and said, "I'm sorry, sometimes my life seems unbearable and Taylor was...she was a good outlet for me."

"How can your life be unbearable? You have a beautiful home, good job, your husband is attractive and successful..." I coyly replied.

"You're not a fucking idiot. You can see there's no love between us. I'm basically his fuck toy, baby maker, house manager, and free dental assistant." Madison plainly stated.

"So leave him, why deal with this?" I asked with genuine interest.

"You don't leave someone like Richard. You don't leave his family." she responded. At that point a clearer picture was being painted.

"We should get going. I'll ping you when I hear something" I told her. We walked back to the dining room and I called out, "Chrissy! Time to go!"

Chrissy stumbled out of hallway pulling her dress down by the sides. Before she came into Madison's view I wiped what must have been cum off the side of her cheek. "Someone's been naughty" I whispered.

"So perhaps we meet up next Thursday, Madison" I said as we headed to the door. "Oh, no, Thursday's aren't good. Richard has a standing poker night out with his guy friends and I take the evening to get a facial. Rituals, you know." Madison replied.

"Okay, we'll figure it out." I told her.

In the car on the way home I turned to Chrissy who was fading in and out. "Well, what the fuck did you get up to with Richard."

Chrissy then explained how she went into the office, where Richard proceeded to give her a glass of vodka and had her sit in his practice dental chair. After she finished her drink he had reclined her and became very provocative. Chrissy detailed how is hands trailed up her legs, to the hem of her skirt, over her breasts and eventually he opened her mouth. With one hand he probed his finger over her tongue, which she instinctively started sucking on. His other hand had slipped between her legs and quickly met her shaved cunt. He proceeded to finger her pussy and mouth at the same time, making her squirm.

Eventually he reclined the chair so her head was slightly below his crotch level. He was still fingering her pussy, which Chrissy said made her moan, but then took his pants down. Chrissy recounted how large his cock looked as she stared up from below his balls. He positioned the tip right at her lips and used his other hand to cock her throat back. She then told me he was rough, really rough. He thrust forward as hard as he could, gagging her and bulging her throat. He wrapped both hands around her throat as he felt his cock impaling her.

Chrissy told me that she couldn't see much except a sliver of light between his ass cheeks as he then pounded her throat in and out with his cock. He had tightened the grip on her throat and was almost feeling his cock through it.

Chrissy had been trained well with deepthroating, so I'm sure she took it well. She said that Richard was very excited and within minutes drained his balls down her throat, wiping the tip of his dick on her cheek. Chrissy thanked him for the cum as I had trained her and he had beamed smiling. He told her that her throat was fantastic and that they would really get to know each other.

"He wants to meet me in our office on Thursday...alone," Chrissy finished. "Good job slut. I'll keep an eye on you with the security camera. I will be following Madison that day anyway." I told her.

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On Thursday I eagerly staked out the dental office, watching Richard and Madison depart in the early evening. I knew exactly where Richard was going and wanted to see how authentic Madison was about her "facials".

I turned on my phone to see if I could pick up the surveillance pen signal I had slipped in Madison's purse and it worked well. Her radio came on in the car, but she quickly turned it down as she dialed a number.

"Hi babe, it's me, I'm heading over." Madison said cheerily.

I knew this bitch was scheming. I followed her car for about twenty minutes until it pulled up to a small house on the other side of town. Madison got out of her car and seemed to have a key to the place and let herself in.

I parked far enough away not to be seen and went through the rear of the house nearby, where there were no fences and a large hedge. I had a good view of the rear of the house where it looked like a romantic dinner was set up for two. Listening on my surveillance pen I heard Madison, "Oh, it's beautiful honey. You are so good to me, god I love you Trent." An average looking guy appeared in the window, who must have been Trent, and received a huge hug from her.

At this point I started recording both of them on my phone as I thought it would be useful to have later.

The two embraced in a passionate kiss, which I could hear clearly through the bug. "Let's have a little pre-dinner fun," Madison said naughtily and led Trent to an arm chair. She pushed him down into it and straddled him, diving in for a long kiss. Quickly she pulled her shirt over her head and Trent buried his face in her chest. He didn't waste time removing her bra and I could see he was mauling her tits as his excitement grew.

Madison got up and sexily turned around showing him her ass as she pulled down her pants. I smiled as this vaguely reminded me of her performance at the Butterfly Cage. She was wearing a sexy white thong that she slowly peeled down, bending over as she did it. Trent's hands were all over her ass, feeling deeply between her crack, through to her pussy.

He also wasted no time pulling down his pants and boxers all at once to reveal an average sized cock that was hard as a rock. Madison turned back around and straddled him, directing his cock right to her pussy.

"Fuck me baby...I've been waiting for you all week," Madison told Trent.

"God, so have I. I love you." Trent responded as he pushed her hips down and the full length of his dick was inside her.

Madison was truly into him as she kept kissing him as she gyrated her hips on his crotch. I zoomed the camera lens to her ass and between her legs saw she was soaking wet as she sloppily rammed her pussy on his cock.

"Mmmm, so good. God I'm turned on by you." Madison huffed as she wrapped her arms around Trent's neck. "I want you to cum in my pussy. I want to feel it hit me deeply."

Trent accelerated thrusting into her as she rode him and I could see both of them tensing up. He didn't say much, but then grabbed her hips hard and thrust up, depositing his seed deep in her.

"Fuckkk!" he cried out as he unloaded his balls. Madison collapsed onto his chest and said, "God I wish we could do this every night."

Trent responded, "Well, I want you too, but you seem to think your husband is dangerous."

"Think? I know. He's an extremely possessive man that if he doesn't get his way he gets violent. And I know the same network he knows, which are definitely no good. But I can't have a loveless life and need you." Madison told him.

Trent paused, "I love you too, but I really want us to be more at some point. Let's take our mind off this with dinner."

I went back to the car and saved down the videos and sound recordings. It reminded me that I should check in on Chrissy, who must have had Richard over at the office by now. I flipped apps to check my surveillance cameras and nearly gasped out loud as the video went online.

Both were completely naked with Chrissy on all fours on her desk, Richard banging away at her cunt from behind with one hand on her hip and the other grabbing her hair, pulling her head back up. I had a perfect view of her face with the angle her head was bent and she was somewhere in between pleasure and pain. Pleasure in the sense that I know she loved cock in her pussy and pain as Richard was massive compared to her and his cock large.

"Unngggh...fffuck...Richard...unngggh!!!" Chrissy cried out.

"You filthy little cock whore. Coming into my house like a total slut and letting me fuck your throat while my wife is there!" Richard yelled out as he slapped her left ass cheek hard.

"Owwww, fuck!" Chrissy screamed.

"No crying about it, you want this." Richard barked as he slapped her ass red multiple times.

Richard flipped her around on the desk, laying her back on it and spreading her legs wide. I had a good view of his veiny cock that was wet from fucking Chrissy. He paused as he lined it up with her pussy and grabbed her throat with both hands. Chrissy's hands went up to it automatically as he was applying pressure to her throat and at that moment he used the leverage from his hands to thrust into her pussy fully.

"Ungggh!! God, it's too big, please!" Chrissy bucked her head back as she cried out.

Richard resumed a frenetic pace, pounding into her pussy hard.

"This cunt is mine now. You'll give it to me whenever I want, understood!" Richard told Chrissy as he sawed into her.

"Yes...yes...of course!" Chrissy meekly replied as she struggled with the fucking and Richards massive hands around her neck.

Her submittal must have thrown him over the edge as he came hard into her right then. He pulled out though and said, "Clean it bitch."

Chrissy got off the desk and dropped to her knees taking his sticky, shrinking cock into her mouth. She licked all around including his balls. "Good girl, I've got to get going now," Richard said as he started putting his clothes on.