Steven was in the middle of a business trip with his Father, Jack, which to this point resembled more of a weekend getaway. It started several days earlier when at his Dad’s office, he met Molly, the Operations Manager at J&E, the family business. Steven was immediately concerned about the leggy redheads intentions. And over the past three days he had become more and more confused. At first she acted like a total bitch. Then the next day she was hanging on him and taking him out to buy new clothes for the trip. And she seemed to know everything about Steven. Too much in fact for Steven’s liking.
The biggest surprise was tonight at dinner. To Steven’s surprise, Molly and the blonde girl that he knew as the company chauffeur, Tamara had joined Steven and his Dad for dinner. It was during that dinner that Molly dropped her bombshell, or so Steven thought. In a straightforward manner, she had told Steven that she wanted him to work at the family business. She also told him by the end of the weekend, he would make up his mind and that Molly would abide by that decision. Molly also knew that Steven slut fucked his Mom, but that she would never use that information to harm Steven.
“I’ll meet you back here in say, 30 minutes,” I tell Tamara.
“I’ll be here. Anything special you would like to see me in?” she asks.
“Surprise me,” I reply as the young girl turns and walks towards her room.
So now here I sit, having been teamed up with Tamara to show me the town. I should have told her what I would have liked to see her in was a smile. Well maybe if I get lucky. I decide I better change and move to the closet wondering what to wear since I had never seen any or these clothes before. I shouldn’t have been surprised when I open the door and find another outfit hanging there, just like when I dressed for dinner. More of Molly’s doing I’m sure.
I meet Tamara downstairs and marvel at her appearance. The elegant burgundy evening gown is gone and has been replaced with an electric royal blue mini dress. One that barely covers her thighs and barely covers her tits. Maybe I will get to see this girl in a smile after all.
“Let’s go this way, “ Tamara leads off holding my hand.
I pat my jacket pockets to make sure I remembered the contents of the package I was given before leaving the restaurant. Inside were $1000 cash and a cell phone, along with a note from Molly. “If you need anything or have any problem, any problem, push 1 and send on the cell phone and you will get me.”
Tamara and I hit some of the most famous spots along Bourbon Street. Even though it was chilly, the night was still filled with carnival like sights and sounds. It seemed that every block contained a club with live music bellowing from within. Still others beckoned horny souls in with the likes of dancing girls, the barkers out front making pleas to pedestrians to stop in.
It was about midnight and we were making our way back up the opposite side of the street. I enjoyed being with Tamara and quite honestly had forgotten most of my life to this point. I didn’t think of Stacie, my Mom, my Dad, Molly, J&E, or anything else. We came to an intersection and I started to walk across when Tamara pulled on my arm.
“We need to go this way,” she tells me.
“But we haven’t been down here yet,” I say.
Tamara turns and walks up to me, her head bent up to look me in the eyes. “And I don’t want to go down there. I want to go down here,” she tells me with a squeeze of my crotch.
It is difficult to hurry without looking like you are in a hurry. Nevertheless, I was focused and intent on following through on Tamara’s comment, and hopefully more. We get back to my room and she takes my jacket off for me and hangs it on the closet door. Then she guides me to a chair. She moves to an entertainment center and turns on some music. Moving back in front of me, she slowly strips for me and once naked gives me an exquisite lap dance that leaves me testing the thread strength in my pants.
Once she finishes, she stands me up and removes the rest of my clothes. By now my cock is ready for action. Tamara moves us over to the bed and we climb in. I notice Tamara looking at the clock and wonder if she has some work related duty she needs to attend to in the morning.
“Do you like to watch porn?” she asks me out of nowhere.
“Well, yeah, I guess I do. Why?” I ask.
“Porn gets me really hot. I mean I am really hot right now being with you, but I don’t know, to me it’s hot watching others fuck,” she explains.
“I know exactly what you mean, it is fun to watch,” knowing how I felt watching first hand last week when I whored my Mom out to my friends.
“I probably normally wouldn’t mention it, but they have some excellent porn channels piped into the suites here.”
“Really? That seems rather odd,” I say thinking about how straightforward and business like my father is to allow something like that to go on.
“Odd or not, it’s here. Wanna watch with me? Figure we can just kinda play with each other until we can’t take it anymore, then I will more than take care of you,” she promises me taking the remote into one hand and my hard cock in the other.
She flips through some channels and then stops on one. “This is my favorite. If I’m not mistaken there is a really hot program coming on next,” she informs me still gently stroking my cock as I fondle her breasts and tweak her nipples slightly.
The scene that is on at the moment has two women and one guy. One girl is on her back with her legs spread and the other girl is on her hands and knees licking her pussy. The guy moves behind the one kneeling and feeds his cock into her. It reminds me terribly of the exploits of my girlfriend and mother the past weekend and my cock gives an involuntary twitch.
“You like that, huh? Two girls and one guy?”
“It’s a lot of fun,” I tell her.
“So, you’ve done that?” she asks.
“Yeah. It’s better when the one girl is licking your cum out of the other girls pussy and then you move in behind her and ass fuck her while she does it,” I explain from the benefit of my experience.
“That does sound hot,” she tells me as the screen finally fades to black. “I think this is the show you need to see here.”
I almost jump out of my skin when the picture comes on. It’s Molly, the Operations Manager.
“Hi, Steven,” the audio feed calls to me. “Don’t worry, I can’t see you, but I know you can see me. I have something I need to show you. It is part of what we talked about at the restaurant earlier. I have a feeling when we are done, you will have a better understanding of many things. And with that understanding, you will be able to make your decision.”
The screen fades to black again and then comes back up in a few minutes. Tamara is still stroking my cock, which surprisingly stays hard. She has rested her head on my stomach and will occasionally slip her tongue out and lick the head.
The screen lights up and it appears to be some sort of medieval dungeon with racks on the walls as well as stocks and other various forms of torture. I hear chains rattle in the background of the audio. It has a tinny echo since there is no music that normally is played while these types of movies play. A figure moves in front of the camera. As it moves away I recognize who it is. It’s Molly dressed in some sort of dominatrix outfit. She calls out.
“Bring him in.” The chains rattle again and another figure moves in front of the camera. It’s another woman that I seem to know. Oh, yes. Charmane, the hostess from the restaurant. She is holding a lead and following her is a man on his hands and knees. He has a leather hood over his head and a leather pouch over his cock and balls. His arms and legs are secured to a St Andrew’s cross. Molly takes the riding crop in her hands and begins to manipulate the man’s groin area, still covered by the pouch.
Charmane takes a small flogger from the wall and begins to whip the man’s hairless chest at the same time. Then Molly speaks again.
“You worthless piece of crap. You better get that tiny dick of yours hard if you know what is good for you. I don’t have all night to try to teach you a lesson. What I ought to do is put you in a pretty pink dress and take you down to the gay bar and let them have their way with you,” Molly screams at him. The humiliation and mention of being used does the trick and the pouch fills out.
“I also understand you failed to perform your earlier task in a satisfactory manner. You probably thought I wouldn’t find out. Well you are wrong, and you will be punished for it.”
With that the two women release the mans ankles and turn him so his arms cross over his head. He is reattached to the cross facing away from the camera and the two women. Charmane moves off camera for a moment and then returns with two leather straps. She hands one to Molly and each takes a position on each side of the man.
They begin to alternate spanking the man’s ass with the leather straps. Oddly enough, I hear no sounds from the man. The whipping continues for about five minutes and then Charmane lets a hand glide over the man’s bright red ass as Molly moves off screen.
Charmane releases the man and leads him to a pair of stocks where his arms and head are secured. The camera moves in as Charmane unzips the front of the hood. “Out,” she orders and what looks like a four inch penis gag emerges from the mans mouth. No wonder he has been so quite. The camera moves back slightly as Charmane moves off screen. Replacing Charmane is Molly, now sporting a 10” strap on dildo. She moves in front of the restrained man and grabs two loops on each side of the hood. She brings the dildo to the mouth opening and pushes it in, forcing it into the man’s mouth.
Molly fucks the man’s mouth for several minutes and the camera zooms out. Molly moves behind the man and grabs the dildo with one hand and spreads his ass cheeks with the other. The camera zooms in to capture the moment of penetration, opening the man’s anus as it slides in wet with his own spit. Molly works until she is able to get all of the dildo in and then starts pulling it out and pushing it back in, very slowly.
“You like being ass fucked don’t you slave,” she asks.
