My Despicable Family Pt. 02

I chuckle, "Oh, I think she might have changed her mind on me. Maybe a little bit."

Alice has a straight face, "She will do anything to get her way. Right now, a motivated you is the thing she needs. She wants those four MEN dead."

I have no smile anymore, "That is exactly what I want as well. Today is my workday. I got the new woman tonight. Tomorrow, I'm using the airplane again."

Laura is fuming, "I have sent people down there before. I'm not losing you now when I need you so bad. I forbid it!"

My anger is upfront and roaring right now, my voice is far meaner than I intend, "I don't give a fuck. Hey! I have been a good boy this week. I shared my body with these women. I shared my knowledge with your friends. Hell, I even shared my body with your daughter. I fucking DON'T like to share. I don't give a rats ass what you think about me going to New York."

Laura looks confused, "I thought you were going to Texas."

I am still yelling, "I don't give a fuck about you! You're a conniving, manipulative bitch. I need to get some things for my meeting with those bad men. The best place is Al's in New York."

What I won't tell her is that I will stop by Texas on my way back. I don't like people hurting my family. Hell, I will even use his runway.

With happiness in my voice, "I have a 5:00 appointment with Heather tonight. I am going to take a nap, and then I will need two suggestions for dinner. I want the '59 Corvette convertible dug out for tonight. Good night my lovely family."

Laura is right behind me as I walk back to my bedroom. She adjusts the alarm clock, takes off her blouse and skirt. She is left with panties and a bra. She is first to get in bed.

Laura says to me, "Men sleep better with a woman in bed. I want you at your best if this is the night they attack. Shut up, get in bed, and get some sleep."

Alice would have done just as well. Why did my man-hating sister volunteer? Did she volunteer? I am tired, I fall asleep.

Chapter 9 - Heather Stapleton

I pull up to Heather's colossal mansion in my '59 convertible (top-down) Corvette. It's manly fire engine red, with white trim on the indentations. It purrs like a Cheetah, waiting to take off in a blink of an eye.

I ask, "Have you had dinner yet?"

Heather gives me a nervous, "No."

I am out of the car and opening the passenger side door for her. She clearly is not expecting this. She smoothly gets in, and I close the car door. I return to my seat.

Before we leave, I ask, "La Pita Brule or Nick's Steak House?"

She is lost in thought, "That's a hard one, both are awesome. I'm hungry, let's do Nick's."

I press the gas pedal, and we both sink back into the fine leather crafted bucket seats.

Fifteen minutes later, I pull up to the steak house. Valet takes the car, and we share a terrific meal. She is easy to talk to, and all the nervousness is long gone. We have a few things in common. For her, at age sixteen, she took over as owner for her mother, who died of a heart attack in bed. She is worth over a billion dollars, and men are knocking on the door to fuck her all the time.

She can't have any of them know she is a virgin. Wow, twenty-six and still a virgin. She has been the owner for eight years, impressive. I can't tell her what I really am, but I do tell her I have a sizeable bank account, although much smaller. I order an excellent wine that will go well with dinner. We drink wine and talk more like we are old friends than in a paid situation.

Heather changes to a shy voice in the blink of an eye, "Is this how you are with all women, or are you this nice of a guy. How much of this is the agency, and how much is you?"

I laugh hard, "Heather, my dear, I am doing my family a favor. They don't approve of almost everything I do. 5:00 date, it's natural to assume you haven't had dinner. From there, I'll wing it. Every-women gets my system the first time. For you, it will be slightly different. It will blow your mind."

Heather is curious, "You seem older than me, self-confident. Are you old enough to be my father?"

I laugh at the child, "Oh no, I'm thirty-two, about six years older than you. Am I too old?"

She is quick to respond with a light laugh, "Oh no. You're fine. I just wanted to make sure you weren't much older. Your body looks young, but your maturity says you are much older. I read people; I handle them differently based on their life experiences. If they earned or were given their money is a factor as well. I knew you earned your own money. You never did say what you do?"

I giggle, "No, I didn't tell you. I'm not proud of my past or what I did so well for a living."

Heather is shy, "My dad is about two levels above your former boss. He knew you by name, called you the best they ever had. I get all prospective dates checked out with dad. I don't want to date a criminal. That's bad for business.

"Naturally, I was intrigued when my dad knew you by name. He doesn't talk about his work often. I know you won't talk about it, but he told me he will help with your pest issue. That's the only reason I brought it up, it sounded important."

He will be recording my phone calls and monitoring my email. I am feeling much better now.

After dinner, we go back to her place. All the lights are out. I inquire, and she sent the staff home. She didn't want them to know what we are going to do. Am I being set up?

She unlocks the door and walks in first. Nobody shows themselves. She takes my hand and seems to be in control now. She drags me upstairs and to a white room. White walls, white carpeting, white pillows, white bedspread, and white sheets.

I don't see any towels, I ask, "We're going to need extra towels. There will be some blood." She jerks to a stop. "Not much, with everything white here, the bit of blood really stands out."

Heather comes back with a large stack of blue towels. This will work perfectly. I lay a few out on the center of the bed. I sit close to her on the bed.

I look Heather straight in the eyes, "If you still have your hymen, I can't stop the pain. I have heard it described as mild up to and including the end of the world. All agree it doesn't last long, and that fucking is so much worth any amount of pain you encounter. I have a system for all my first timers with me. You will get that tonight. Any other time, we do the things you like."

Heather is still dressed. I have her stand up. She wants to remove her clothes, I stop her.

I explain, "Baby, I will do this for you. My touch will burn your skin. Lightning bolts with shoot to your vagina. Your stomach will be alive with butterflies. Close your eyes and take it all in. It's an amazing experience.

Heather takes a good, deep breath and then closes her eyes. I unbutton each of the seven buttons slowly. My fingers touch her breasts often, and she has several small intakes of her breath when I touch her. I move around to her back. I pull the blouse off her body, one arm at a time. While doing this, I exhale a humid breath on her neck, kiss her neck, she flinches, and then take off an arm of a blouse. The garment falls to the floor after both arms are released. She moans.

She has a long skirt on. I unzip the zipper on the side, and then it's easy to pull down the skirt. She is wearing a lovely deep red matching bra and panty set. It's edged with a frilly white lace. Nice quality stuff.

I wrap my arms around her body, pulling her close to me. Her leg runs into my hard cock. She squeaks and tries to move, she can't. She gives in to touching my cock. I use my tongue on her earlobe as my right hand slowly pulls down the right bra strap. She emits an "Ohhhh..."

I move to the opposite earlobe and use my left hand to slide the left strap off her left shoulder. She shudders at my touch. With a practiced move, one hand holds the cups in place, while the other uses a deft flick of the wrist to unlatch all three clasps at one time. My second hand comes around, now I have one hand holding up each breast.

I allow both breasts to fold down unevenly. That means one is revealed shortly before the other. I move around the front to get a good look.

I smile at her, "You are very nice looking. You're still young enough that your skin is perfect, no crow eyes, and your breasts are perky. They feel amazing."

My lips reach down and attach themselves to the light pink nipples that have turned hard since I started.

My voice is raspy, "Feels amazing to almost be naked in front of a stranger, right?" I can see her body swaying, she loves this.

I slowly descend her body. My fingers grasp her ass. I grab it hard, which causes her to moan. Slowly, I pull the drenched garment down her legs. They don't flutter down like light material should. Nope. These fall to the floor with a thud, like dropping a wet washcloth.

Heather turns red from embarrassment, all the way down to the top of her breasts. I lean forward and eat her pussy until she orgasms. It took almost no effort to eat her to orgasm. Her legs give out, I catch her. I pick her up and place her on the edge of the bed.

I take off my shoes and socks, then stand in front of Heather by a foot or so. Heather sits up, and she comes back to her senses. There is a massive smile on her face.

Heather sounds shy when she says, "My older sister suggested an escort. She said your kind, discrete, and tender. You will do what I want. She had no idea that I didn't know what I wanted. I find out all my rich friends are using your company. None of them have ever heard of you before. I didn't want them to find out that I was twenty-five and a virgin still.

"I took over a manufacturing company at age sixteen. Fourteen hundred people rely on me for a paycheck. Everyone took advantage of me until I started firing people. Now they all think I'm a bitch. I am. I had to be. Now here I sit, literally paying a man to fuck me."

She buries her face in her hands as she starts crying. I let her cry. I have a sister; I have seen this before. Oh, woe is me, pity me, look how sad my life is, show me, love. Blah, blah, blah! I am not falling for that shit.

After a few minutes, she looks at me and is furious, "You heartless piece of shit!"

My response is priceless and well-practiced, "You, done yet? I have an older sister that is ten times better than you. It's better when you ease into the tears slowly and then kick your legs on the bed, you know, a proper temper tantrum."

She lunges out at me with a fist. My hand catches and holds it.

"People have died for doing less than that to me," is my standard reply.

Heather pulls her hand back like it is on fire, she eyes me carefully.

My voice is calm, "My sister owns the Escort agency. I'm trying to snuff out some truly heinous individuals that love carving up pretty women like you and the escort. I do bad things to bad people.

"You're my cover for the night. I'm not big enough to be an escort, yet the women that have been with me so far are begging to get me back. How about we continue without the bullshit, have a good time, and maybe, just maybe, I will let you live."

Heather looks like she is holding her breath.

I smile at her, "That last part was a joke." She looks visibly relieved. "I told you, I only hurt bad people. Would you like to remove my clothes?"

She is unsure, "Do I?"

I nod my head, yes. That pleases her.

"This is for you. Enjoy yourself," I feel like a broken record.

For her part, she does break out into a broad grin. She stands very close to me and unbuttons the two on my suit coat. She pushes the jacket off my shoulders, and it slips down my arms. She places the coat on a large chair, folded over the back. Next is my shirt. She looks to be having an internal debate between unbuttoning and ripping the shirt off. I assist.

Using a deep, soft voice, "Anyway you like it."

She looks up at me like, "Do you really mean that?"

I nod my head, "Yes."

She unbuttons one in the center of my chest. One hand goes to the right side, and the other to the left side of my shirt. Like opening a zipper, she pulls hard, and buttons fly off alternating right and left from the center to both ends. She has a magnificent smile on her face. That was fun and exactly what she wanted to do. She leaves my gold watch, gold chain neckless, and my three gold rings on.

She now unbuckles my belt and smoothly pulls the belt through all the loops. The button is next to be undone, and the zipper follows quickly behind. This is her first time touching my hard cock as she unzips me, the head pops out a bit. She looks up at me with a big "O" on her face. I giggle; she is cute.

She pushes my pants down with my assistance in stepping out of them. Her eyes are bulging at seeing the long stick pointing out of my boxers.

I grin as I whisper, "Now, wasn't this much better than me taking off my clothes?"

Not sure she heard me, she is still mesmerized, staring at my cock.

I prompt her, "Go ahead, finish stripping me. Prepare me for pleasuring you."

In a quick move, my boxers are on the floor. She is still staring at my cock and has a huge smile on her face. She looks up at me and then back at my cock. I guide her to the bed and have her lay down on the towels.

I move to the bed and straddle her body, my cock dragging over her body. I start my system with light, gentle kisses. You know the routine, kiss, pamper, play with breasts, kiss breasts, suck on nipples.

When it came to eating pussy, this is a bit different, she has no experience. Her reaction was too explosive previously. This time, I came in softer and slower. I don't want her orgasms running into each other. Not with her experience. I run into a problem. As I slowly and tenderly lick her pussy lips, she explodes in her orgasm. Ooops. It seems that Heather loves the slow and tender. Rather than staving off her orgasm, I induced it quicker.

I stop my ministrations; she needs to catch her breath. Her heartbeat is wild, she is working hard to breathe, and she is perspiring heavily. Her hair is matted, and we are only two minutes into eating pussy. She does indeed love this. I start up again, this time harder and faster. This sure is better, who would have thought?

She gets five good orgasms before she has had enough. Most stop earlier, I am impressed. I walk on my knees up the bed, so I am in position. I stick a finger into her pussy, lubrication is no issue. I run my finger along the side of her clit, and she holds her breath tight. Heather loves that feeling.

I rest back on my ankles, "I will stop as soon as I'm through. It won't stop the pain, but it will stop more pain or from making the pain worse. You tell me when to continue. I'll wait all night for you."

I slowly push forward until I encounter an obstacle. I softly apply an increasing amount of pressure on the hymen. Soon it gives way, and I stop pushing forward. Heather's reaction is to pull her legs back and release a quick scream. She is frozen with fear that it might get worse.

Heather is lucky, the pain isn't that bad, and she wants to feel my cock pressing into her again.

She looks me directly in the eyes, reaches forward, and kisses me right on the lips. The kiss lingers for a few moments before she releases me.

Heather's voice is shallow as she says, "Thank you, it wasn't so bad. Please continue immediately. I want to feel that monster fill me up."

From there, it goes according to the script. The only difference is that Heather feels less like a client and more like a date. Everything is more natural. I don't feel like I am following a list, I am having sex with a woman I like.

By the time I get home, the sun is coming up. Alice is sleeping on the couch, I guess, waiting for me. I tap her shoulder. She looks up at me and smiles big. Her arms reach out to me yet are too short to touch me. I smile at her, bend over, and pick her up. She wraps her arms around my neck and her legs around my waist. Her head is on my chest, and her eyes are closed.

I stop at her door, so I can open it. I hear her say no, by saying "Mmmm - mmmm," and shaking her head no. It's her room. Wait a minute, why was she waiting for me? I walk to my room, nothing from her. I walk into my room, and she reaches out and closes the door as we walk by. I set her down on my bed. She rolls over.

I strip my clothes off and get in bed. Alice rolls back, right into my arms. I smile as she places my hands on her breasts. I quickly fall asleep; Heather wore me out.

Chapter 10 - Mary Kline Again

On my day off, I trace the money to our accounting company. Who processed the payment of each of the people that died? The problem is, it's not the event itself, but any time previously. That exponentially increases the leads to track down. It's a long tiresome day.

The following day is just as dull. I hate tracing payments, invoices, and anything in between. It's odd, it's 3:00 and I don't know where I am going. I go up and start getting ready. I shave, take my shower, wash my hair, and dry myself off thoroughly. I put on my jewelry, my suit, my cologne. I am one hot stud.

Sitting on my bed is Alice with a card. She isn't happy at all. I have a smile on my face up until Alice tells me that I am meeting Mary Kline again. She is fuming.

Alice growls at me like this is my fault, "Mary was a bitch, and mom was all too happy to sign her up again. Be careful with this one. She's super wealthy and likes her fun." She hands me the card.

+++++

I am nervous about this woman. She is an ice queen and not used to losing. My sister did get her to add a zero to get me next, that's worth something. I see Mary coming out of the house as I pull up. She is glaring at me. This woman is ignored by her husband, he is a control freak. I guess she likes to be in charge anywhere she can. Paying our fees, she probably thinks she deserves that. Too bad, I don't play that game.

Mary puts out her arms and greets me with a hug and a smile. On hugging her, I see two large men pop out from behind the door. I also feel a tiny pinprick.

Mary tells me with a strong voice, "I have a needle in you. Don't move, or it might kill you. These men will help you. Good night Ken."

I fall asleep. What the hell!

+++++

I wake up, naked, in a dungeon, on a big table. I am restrained with chains securely. There are two huge men in leather with masks covering their faces. Both men have more muscles than a bodybuilder. These are steroid users, they're too big. Mary is in a glossy leather outfit with a whip in hand. Oh yes, to make this fun fest even better, I have a ball gag in my mouth.

Mary has a mask on, but it's obviously her.

Mary uses a robust commanding voice to explain to me, "My husband calls me dumb. The house staff ignores me, because my husband pays them. Nobody takes me seriously. My one time I get to be in charge is when I hire an escort. Typically, they take a hell of a beating. Then you came along, and you deny me my fun. You're immune to legal drugs, not illegal ones, by the way."

Well, isn't this just fine. Are these the killers? It's not who I expected, maybe a parent?

She snaps the whip with expert precision in front of my face, breaking me from my reverie. Oh shit.

Mary says to me, "I'm going to strike you ten times with a variety of implements. I expect you to count them out and then say, 'Thank You, Mistress. May I have another.' Failure to do so will cause me to start at one again."

The ball gag is removed by an assistant.

Holy fuck! I need to get out of here. I use all my strength to pull on the chains. Nothing. This is just wood, if I pull enough, it will break. The pain will give me extra strength. Then I will kill them all!

I see the whip circle twice, and then it goes across my ass, and I hear a snap.

I cry out with a shout, "One! Thank you, Mistress, may I have another?"