The Long Weekend: Thursday Pt. 01

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Brother is asked to find out if his sister is cheating.
4.2k words
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Part 1 of the 2 part series

Updated 08/30/2017
Created 11/26/2008
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One: The Favor

I never expected the phone call from Chuck, my brother-in-law. See Chuck and I have never gotten along, probably starting from the fact that I called him "Chuck" instead of Charles.

Chuck was an accountant with a pretty big firm and ran his own branch in a fairly large Southern City (not going to say which). He made a monthly trip to New York for the monthly meeting and every quarter he had to go there for a week. It seemed pretty micromanaged to me.

Chuck was in his 48 years old and that was pretty much my big problem with him, that and the fact that he was dull and conversationally useless.

I was going to turn thirty in about six months, and in college. How does a thirty year old end up an undergrad in college (not going to say which one). When I graduated high school I was almost nineteen, I had one of those late summer birthdays and didn't start kindergarten till I was six. My parents wanted me to start off to college straight away, but I wasn't having it. After graduation I ran off and joined the Merchant Marine, I basically traveled the world where ever I could get a ship to take me. Then when I was twenty one 9-11 happened I opted out of the contract I was in at the time and joined the army. The six years I spent in the army I had four combat tours, two in Iraq, and two in Afghanistan. When I got out I figured I had the GI Bill, might as well use it. So here I am.

"Dirk?" Chuck asked as I answered. Don't know why he asked it as a question because it's my cell phone, who else would be answering it? And I don't know why my parents named me Dirk.

"Hey Chuck, how are you doing?" It was one of the rare times I wasn't sitting in my studio apartment studying. I was sitting in my studio apartment playing Halo 3. I didn't really want to listen to my brother-in-law's shit.

"Dirk thank you for your time, I have an issue I need to discuss with you regarding Tricia." Tricia is my sister, aka Chuck's wife. And who talks like that anyway?

"Everything ok?"

"Actually at this time I'm not sure, but I would like to ask that you keep this conversation in confidence."

"Uh, sure Chuck, between you and me, now what's up?"

"Dirk I'm afraid I need your help, I believe Tricia if she is not already, she is about to begin an affair."

I was so stunned I didn't see the Grunt stick a plasma grenade to me and I was brought back to my senses as Master Chief exploded on my TV screen. "Why do you think so?"

"One of the men in my employ, his name is Chapman, Curtis Chapman, is soon to be throwing a party per se. If I understand correctly woman will come and put their keys in a bowl, then go to a private room, men will then come, pay for Entrance to the floor and be allowed to go room to room and sample the wares so to speak. Afterwards there will be a silent auction to bid on the order of choosing a key from the bowl. At which point the woman will be expected to service him the rest of the weekend. Curtis has arranged this party, from his work computer and I monitored a confirmation e-vite from Tricia's email. I believe she is going to be one of the women at the party."

It sounded like a rich man's version of a version of a key party/bordello. "Ok, what do you need my help with?"

Chuck sounded visibly shaken. "Well, I know that some of the party per se is to be an equal ration of men and women. There is a buy in of $1000. The party will be the weekend of my quarterly meeting, so I will be gone Wednesday to Wednesday. It is the Veterans Day weekend, so most people have the weekend off, but we are continuing with our Quarterly meeting as per usual."

"Chuck," I interrupted, "What do you want me to do?"

"Dirk I know you have your winter holiday that week. "I have purchased a ticket in your name, arranged a limo to pick you up at the airport. And I have paid the $1000 buy in. I want you to go to the party and find out if Tricia is cheating on me."

I thought about it for a long moment. "Chuck, if they know your brother-in-law is going to be there they are going to hide Tricia."

"No, I've told Curtis that I've never actually met you but that you are the younger sibling of my old college roommate."

"So you want me to go to a sex party and find out if Tricia is cheating on you?"

"That would be the first part."

"Ok, what's the second part?" This was getting more and more complicated.

"I have arranged a brief case of $10,000 to be in the Limo. If she is there you are to use this money to try to win the silent auction. I want you to get her keys so that someone does not," it sounded like his voice cracked and I could hear the sniff that accompanies tears through the phone, "use my Tricia."

"Chuck you know your spending over eleven grand to FIND OUT if your wife is going to cheat on you? Something about this doesn't seem right man."

"Please Dirk. I will also forward $2000 to your account for your, inconvenience."

Now don't get me wrong, I don't like Chuck, but I'm not a total bastard. "All right Chuck, I'll do it."

"Thank you Dirk, I trust I can be assured of your confidence in this matter?"

"Absolutely man."

I had three days before I was to go to the airport. The next day I was received an email on one of my accounts (won't say which provider). It gave me the address to the hotel, a password to be allowed on the floor, and a dress code. That's right a Dress Code for a sex party.

As I packed my bag, I figured I had a win/win situation. If my sister was cheating, I made two grand to find out, then I'd spend a weekend with her, and at the end of it if I decided I should tell Chuck, I would. If I didn't, I made two grand, got a free weekend with Tricia, and she could do what she would do and I'd tell Chuck everything was fine. If she wasn't cheating, I was getting paid to go to a sex party, where I wouldn't have to worry about a guy trying to poke at me, and getting paid to take the pick of the litter. It seemed like win-win.

I then started to wonder if Tricia was actually cheating on Chuck. Chuck was a chunky 48 year old who was balding. Tricia was only thirty six, with flowing golden blonde hair, grayish blue eyes, and a very shapely figure. She modeled when she was younger and still during the holiday sale papers she appeared in ads. She didn't have an agent anymore but she did fine with freelance.

Thursday afternoon I drove to the nearest airport (stop trying to find out where all of us live) and boarded my flight. Chuck had sprung for first class. The offered me champagne, but I ended up having three Jack Daniels in the hour and a half flight. I figured I didn't have to drive when I got there so I didn't worry.

I was wearing a plain white t-shirt and khaki trousers, as per the Dress Code. I exited the plane and skipped the baggage claim since I only had a carry on. I won't lie, I was getting excited.

The Limo ride was fun, and there was an open bar, where I helped myself to another Jack Daniels. My leg started shaking from the excitement. I put on my plain ball cap, and my sunglasses (a plain black ball cap and a nice pair of wire frame Ray Bans) that completed the Dress Code, then opened the brief case that had awaited me and counted the ten packets of $20's each valuing at $1000.

The Door Man of the hotel opened the door of the Limo and I walked inside straight to the elevator bank. They actually had a guy working the elevator and he asked my floor.

"Twenty-fifth, the Chapman party."

"I'm sorry sir that is a private party."

I smiled, "I understand Sir, but I am Mr. Chapman's friend from Alberta." Alberta being the code word I was given in the e-mail.

The gentleman smiled, punched a code into pad and then the button for the 25th floor lit up. The elevator ride seemed to take forever and I almost jumped out of my skin when the Operator said "Your floor sir."

Two: The Tasting

I stepped out into the open way by the bank of elevators. I was met by a man with a clip board. "Your name sir?"

"Bond." I was going to kill Chuck for picking my fake name.

The man looked down the clip board. "Yes sir, I see everything is in order. May I?" He gestured at the brief case. I held it up and he sealed the seam with a red tape. "So that you may insure that it has not been tampered with during the evening." At that point he gestured to chair that held a place card bearing the name Bond. I placed my bag and my brief case there.

"Very well sir, a review of the rules." I stood and waited as he read off of his clip board. "You are not to remove your hat or glasses. The ladies are blind folded; the blind folds are not to be removed."

"Check."

"The women are in separate rooms. You are to go from room to room, tasting the wares so to speak."

"Ok." I was anxious.

"You may touch the women however you wish. But you must stay above whatever clothing they are wearing. None of their clothing may be removed or circumvented. You are not to ejaculate on the ladies, you are being monitored and both offenses will mean your immediate expulsion. Those rights are for who chooses them after the bidding. You are allowed to have them touch you however you wish."

That was a bummer about not getting off or going under their garments, but I nodded my agreement. "When your time in each room is up you will receive a phone call telling you which room to proceed to next. When you have completed the circuit you will be sent to a room to make your bid for the silent auction."

"Ok."

"All the ladies are on birth control, thus protection will not be required for the weekend."

"Good." FUCKING AWESOME!

"The winner of the silent auction will have first pick of ladies, to have for their pleasure until 5 pm Monday. The ladies homes and vehicles are open to you for your use."

The home and car bit was interesting. "So it's like a key party where you don't quite choose at random?"

"That is a fair assessment. The last point is a point of safety. There is a camera and all activities are being recorded. At the end of the weekend the ladies will call and her DVD will be mailed to her. If she does not check in at the end of the weekend we will take the DVD and all information we have on you to the authorities. Any suspicious activity in the rooms will lead to your immediate ejection. Do you agree and understand?"

"Yes." I had to force myself not to bounce.

"Very good Mr. Bond, please proceed to room 2507 and enjoy."

I walked down the hall and didn't even hesitate as I entered room 2507. Sitting on the edge of the bed, in pair of red fishnet stockings, red thong, and a red bikini top with a black blind fold over her eyes was a woman in her late forties, with a deep spa made tan, bright red toe and fingernails and matching lipstick. Her hair was cropped short and was black but peppered with grey along the sides.

I didn't hesitate. I crossed the room pulled her off the bed, eliciting a squeal from her, and into my arms. My right hand clamped onto her firm runners ass, and my left closed around her left breast feeling the nipple under the C cup go instantly hard and poke against the fabric. I pressed my mouth against hers and she gladly opened it allowing my tongue inside to massage her tongue.

She pressed her tongue into my mouth hand her hand sought out the front of my pants running her hand along my rock hard cock.

I slowly backed her up to the bed and laid her back upon it. I took her left leg and placed it up on my shoulder, bent down and began to trace overlarge sucking kisses along her thong to the point where I was sure her clit was. I then kissed up along her slightly pouched stomach and ran my tongue under the bottom of the swell of her breasts which while she was lying down could tell sagged a touch. All in all she was in wonderful shape for her age.

I lie fully atop her and ground my khaki covered cock against her thong covered pussy.

I am fairly sure she reached an orgasm before our time was up, and running my hand over her thong showed exactly how wet she was.

When the phone rang she held onto my hand as I answered. The man with the clipboard was on the other end telling me to proceed to room 2509.

She grabbed my hand and held it tight to her soaking wet thong, pressed her chest against me and tried to cram her tongue down my mouth even as she walked me to the door.

In 2509 I found a young, had to be 18, Asian girl in a white button up shirt tied in the front, a short skirt made to be a school girl skirt but so short I could see her white g-string beneath and a blind fold made of the same material as the skirt. She shyly stuck her finger in her mouth and sucked on it while her two pig tails bobbed side to side.

I closed the distance between me and her and not forcefully, but with authority turned her around and made her brace her hands on the bed then I reached between her legs with my left hand and began to massage her pussy through the tiny front of the g-string and massage her ass with my right.

After a few minutes I sat down and pulled her into my lap, she straddled and faced me. We made out as she gently ground her pussy into the cock under my khaki's. I did get the feeling that in a lot of ways this seemed routine. Like this was something she did often.

"Love you long time." She whispered with a heavy accent, probably fake, while she ground away against me.

When the phone call came telling me to go to 2511, she waited on the bed for her next patron.

In 2511 I found a girl with a long red pony tail that fell to her ass. She was in a cheerleader outfit and her blind fold was in her school colors, yellow and white. She was standing by the window, while blindfolded she did a back handspring, turned, jumped in the air doing the splits in the air pom-poms held high.

I walked to her and again grabbed her ass with my left hand and fondled her breast through her cheerleading top we kissed for a moment then I lay her back on the bed, rubbing my hand between her legs.

"We have a hot tub, and a steam shower." She almost moaned breathlessly as I kissed her neck. "My parents are in Europe." She grabbed my face in her hands and pulled my mouth to hers, she using almost too much tongue. "I'm a virgin," she moaned as she put her hand atop mine and ground it into her crotch, "you can have it. You can have it all. I want you, I want you so bad."

The phone call seemed to come too early and she lay on the bed still rubbing herself between her legs moaning "I want it inside me." Over and over.

I stepped into the hall and poured me a double of whiskey that was in a decanter in the hall and downed it, and then I reached my hand into the front of my pants and squeezed the base of my cock painfully until my erection died. I stood in that hall hoping to hell that Tricia wasn't in this hotel, that she was faithful to that loser bastard Chuck. Because I wanted to take that cheerleader to her home and fuck her face, fuck her tight ass, pop that goddamned cherry and rail her until she couldn't walk anymore. If she wanted it inside of her I'd fucking oblige.

I wanted to fuck the shit out of the little teasing virgin cheerleading bitch, until I walked into room 2513

Three: Room 2513

I entered room 2513 and there she was, leaning against the windows, back to the city. Her wavy golden blonde hair fell to her naked shoulders. Her skin was flawless, her breasts were concealed in a strapless black bra, a black pair of almost sheer panties hugged nicely to her hips and a pair of black silk gloves covered her hands and forearm up to her elbows. Her stomach was flat and her belly button was deep. The black of the underware offset the color of her skin and hair beautifully. The black blindfold covered what I knew were beautiful blue eyes. Five inch black stiletto pumps showed off the amazing arch of her legs. I stood staring at the thin nose, high cheek bones and full not quite smiling lips, and perfect body of my 36 year old sister Tricia.

It was in that moment I remembered the rules. They were watching and if I were suspicious they'd kick me out and then I'd lose the chance to win her in the auction for Chuck. I had been a horn dog so far so I had to act one now.

I hoped it looked natural as I crossed the room and pressed her between me and the window pulling her lips to mine. I had forgotten that she was about an inch and a half taller than me. I made myself open my mouth and she did the same dutifully. She had the taste of mint, and I realized that she had been brushing her teeth between visits to the room and that was actually quite comforting.

Then to my embarrassment I found I was grinding my erection against her panties. I knew I'd have to find a way to explain everything later, but in that moment I had to keep it up or I'd lose the chance to bid in the auction.

I slid my tongue into her mouth and found it dutifully caressed by her tongue. I reached up and grabbed both of her bra covered breasts in my hands and felt the fullness of them. I kissed her neck behind her ear and traced my tongue down to her right shoulder.

Then without thinking I took her gloved hand and took her to the bed. I lay her down and bent her knees with her feet on the bed. I lust had taken me and I dove between her legs and kissed and sucked the front of her panties. I could feel her trimmed pubic hairs underneath and I could feel the head from her pubic mound. I found the place her clit should be and placed my mouth over and around it and began to hum.

She moaned, and it was the most exciting sultry thing I had ever heard. I hummed louder and her gloved hands found my head and held me there, kissing the front of her panties and humming my way along her slit.

She eventually began to pull on my head and I climbed up her body and pressed her beneath me, grinding my erection into her pussy, fencing my tongue with hers in a long passionate unending kiss. My hands roamed her body and her hands roamed mine. We dry humped and how I didn't cum I will never know.

Every other room I got the phone on the second ring. In 2513 they had to call twice.

"Sir, you should know that if we are forced to call you twice again you will be expelled from the floor. Now continue to room 2515.

I walked backwards from the room, and I watched as she stood up and moved back to the window, city lights behind her. I felt horrible and hornier than I had ever felt all at the same time.

I barely remember the other rooms, the details were all lost. I simply kept reliving the moments with Tricia in 2513 over and over in my head.

2515 had a large breasted, large hipped black woman with short hair done into rows. She kept saying she wanted cream in her coffee.

In 2517 there was a woman that probably weighed 187lbs. I fooled around with her and played with her massive breasts but my mind wandered.

In 2519 there was a Mexican girl with a Maid's dress, thigh highs, and a sheer camisole. She said if I took her she would call friends, and I could have a threesome or foursome.

In 2521 there was a woman in her late fifties, with giant breasts that had to be fake. She talked about how she loved to get pearl necklaces and facials.

I had to walk to the end of the hall after that to room 2503. I wanted to go back into 2513 more than anything. In 2503 there was a girl who kept calling me Daddy and Uncle and asked me to "make me yours."

In room 2505 there was a woman with severely short platinum blonde hair, muscular legs, in thigh high boots, a black leather g-string, and a leather top that barely covered her almost non-existent breasts and held her hands tied at her shoulders with a bar behind her neck. She had a red ball gag in her mouth and on the bed next to her was a riding crop. I bent her over a chair and spanked her until the phone call came telling me to go to room 2508 to make my Silent Bid.

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