Management Training Program Pt. 01

My family owns a large regional supermarket group, that is very profitable and I live very comfortably. We have offered up and coming employees a training program to transition from the store to the corporate office. Annually I review the applications, conduct the interviews and award the promotions.

This year a younger single mom Jennifer that is an assistant manager in a smaller suburban store signed up. I wasn't sure she had what it took but I scheduled the interview.

She came in dressed in a sexy business suit. We were about mid-way through the interview and she is realizing she isn't meeting the criteria.

She looks at me. "Carl I really need this. My daughter is starting college. My son will be in 2 years, loans and grants still leave a lot to be paid. I can't let my kids down. I will work harder than anyone. I will start at the bottom, and do anything."

I know she means any job, but I hear something else. "Jennifer I just don't think you are qualified."

"Carl, please I am begging."

I can't help it. With the correct words stressed I say. "You are BEGGING me to do ANYTHING to get this job?"

Her face shows the shock as she realizes what I am suggesting. She sits there staring.

"Jen thank you for your time. We will let you know our decision."

"Wait." She says quietly.

I get up and walk to her to shake her hand. "I will be at the Marriott bar at 5pm should you change your mind." I say quietly and I walk out.

Jennifer's face betrays her shock and confusement. I walk out smiling inwardly. She is a pretty woman. She has longer black hair, brown eyes and fair skin. She is a taller woman probably around 5' 10'. She is probably B or C cup tits and just enough ass. Once I leave the room I am imagining doing all sorts of thing to her.

I spend the last hour of my day fantasizing about Jen. I leave the office and head to the Marriott. As I walk through the lobby I notice Jen is walking maybe 30 ft in front of me. She stops just inside the bar doorway looking around. I walk up and slide my hand over her ass as stand beside her. She jumps a bit and lets out a small gasp as I give her a small quick goose.

"Why Jennifer whatever is a pretty woman like you doing in a hotel bar after work hours in the middle of the work week?" I don't give her a chance to respond but I can see the fear and confusion on her face. "I insist you join me for a drink." I take her arm in mine and escort her to a more private table.

The waitress comes right over and before you know it we have two drinks. I take a drink and look at Jen with a smile. "So I am guessing you want to take me up on the 'I am begging and I will do anything' offer."

"I am not sure I can do Anything." Says Jen.

I reach for my wallet. "Well it was nice running into you and having a drink Jen."

"Wait. I can do anything for my kids, but I need some clarification. What exactly are you asking or expecting?"

A stare at her for a minute. She is mine. "Once or twice a month at my discretion, for a few minutes to a few hours each time again at my discretion you will be my plaything. No saying no. I want to do something, you do it. I will promise you I will never put our jobs or reputations at risk. I might have you come to my office at 5p on a Friday but never in the middle of the day. I will promise to watch over your corporate progress. I will take you under my wing if you will. To start it will be about a 50% pay increase."

I take a drink and wait for the gears to turn in her head.

"I need clarification on plaything." She says so very quietly.

I lean over and glare at her. "When I want. Where I want. Oral, anal, pussy, threesome, orgy or Bondage. Does that cover it?"

Her face blanks and goes pale. She just stares for a good 30 seconds. "I need an answer or I am leaving." I tell her.

She is still staring 30 seconds later. "Ok nice to see you and I get up."

"No I will do it." She says.

I sit back down. I glare at her again. "I am not sure I believe you. I need a show of good faith right now. I will get a room and you will go upstairs with me now or the deal is off."

She drops her head and very quietly says "Ok."

I drop money on the table and get up. "Let's go." She takes my offered arm as we walk out. I hand her some cash. Point to the hotel store. "Go get some sex lube. You are going to need it I think." I pull my arm out of hers, goose her ass and I walk to the check in desk.

I am checked in when she returns with a small bag. I walk up to her. I put my hand on her ass rather then take her arm and walk her to the elevator. We ride up in silence.

I open the door and walk in. I take off my suit coat and put it over a chair and sit on the sofa. "Let's see what I am working with here. Strip!"

She stands almost as far away from me as she can and takes off her blazer. I push the coffee table aside, and kick off my shoes. "Come stand right here." As I point to the floor in front of me. "I want an up close and personal look."

She steps forward and you can see the nervousness and fear on her face. She kicks off her shoes and pulls down her pants. I get a brief look at her white panties, but she stands up and her blouse drops down covering her. Her legs look smooth and sexy.

I compliment her. "Those are some sexy legs. I can't wait to feel them wrapped around me."

Her head stays down and she is unbuttoning her blouse. She pulls off the blouse and stands before me in a basic white bra and panties. Again she is not moving and looking down. I stand up in front of her. I have to tilt her chin up to look at me.

She just stares.

I squeeze her chin a bit. "I said strip. Take those off before I rip them off and send you home commando." I stay right in front of her as she pulls off her bra. As she drops it to the floor. I reach down and start pulling on her nipples. They are nice and big and perky when played with. "I am going to have a lot of fun with these."

Jen moans a bit as I squeeze a tad hard. I release her nipples. "Drop the panties."

Jen stands back up after stepping out of her panties. I reach down and feel her pussy. "It's bone dry. See wasn't I nice telling you to get lube?"

Again she says nothing. I grab her by the back of the neck and hold her bent down over the bed. "Jen this can be a system of rewards and punishments." I spank her closest ass cheek with a pretty good swat. She yelps out in surprise. "Next time you don't answer a question, thank me for being nice or giving you a compliment I will punish you."

"I am sorry Carl. Thank you for the compliment earlier." She says.

I reach down and smack the other cheek harder, and she screams out again. "That is for being a slob. Do you want your suit to get wrinkled on the floor. Pick it up and hang it, and never drop my suit on the floor."

"No sir. I am sorry. I wasn't thinking."

"You weren't thinking? Do you do that often? Do you think I want you in the corporate office if you don't think?"

Jen is now flustered. "No I didn't mean that. I am sorry. I will hang it up."

I sit back down and watch her pick up her clothes and hang them. I stand up and look her in the eye. "Remove all my clothes."

She starts unbuttoning my shirt and pushes it off my shoulders. She takes and lays it neatly over my suit coat. "I will hang it in just a moment. I need your pants to put on the hanger first." She unbuttons my pants and pulls them down and holds each leg as I step out of them. She then starts folding them at the pleats and gets a nervous look. I am standing there in my boxers with my hard on growing.

"Is there a problem?" I ask her.

"I am unsure which task to do first. Should I hang up your suit or continue stripping you?" She asks.

"A smart person will always ask a question they don't know the answer to. Hang up the suit."

She carefully hangs it and returns to me. She pulls my boxers off and again helps me step out of them. She then pulls off each sock. The entire time doing her best not to look at my hard on. She stands up. Folds my boxers and socks and puts them on the table.

I sit on the sofa. "Come sit on my lap. Let's talk a little."

She sits on the furthest point of my knees. I grab her around the waist and legs and pull her onto my lap with her legs on the couch while she leans against me and the arm of the couch. I reach between her legs and adjust myself so I am sticking up against her pussy.

"See isn't that more comfortable?"

"Yes thank you."

I rest a hand on her upper thigh with my fingers dropping between her legs. I feel her stiffen. "Now let's continue the interview. When was the last time you spread these sexy legs for a man?"

"What?"

"I know I don't stutter. Do you want more spankings? Don't play games with me. Answer my question." I tell her a bit sternly.

"Quite some time ago." She answers.

I reach up and slap her tit. She screams out in shock. "I can spank more than your ass. I ask a question I want an answer not an estimate."

She reaches up and holds her stinging boob. "Umm 8 years ago at a wedding."

"See that wasn't so hard. "Do you let a guy cum in your mouth and swallow?"

"I have."

"Anal?"

"I never have."

"Nice I get a cherry ass to pop." I put my hand back on her thigh and push it between her thighs. She relents and spreads her legs. I start rubbing her dry pussy. "Ever done a threesome?"

"No."

"Ever had sex with a woman?"

"No."

"Oh I am going to enjoy breaking you in. It's been 8 years. You must use a dildo at home right?"

"I had a vibrator but it died years ago. Now I use my fingers."

"Show me. Play with yourself ."

Jen sighs and reaches down between her legs and starts rubbing her clit. She lets out a small sigh after a bit. I turn her head to mine and kiss her. Again she stiffens but when my tongue licks her lips she opens her mouth, and starts to return to kiss. I reach up and start teasing her nipples. I have had enough coddling.

"Lay across the bed." I tell her as I break the kiss. She stares at me again. "You are going to lay across the bed. You are going to blow me. You are going to fuck me, and I am going to cum in your mouth. Move now or I will spank that ass so hard and so long you won't want to sit for a few days."

A scared look pops up on her face and she gets up and moves to the bed. She lays across it. I walk up and pull her by her armpits so her head is off the bed. She looks up a tad scared. I grab the bottle of lube and squirt some on her pussy and her hand. "Finger fuck yourself while I face fuck you. For your comfort I would think you would want a lot of lube when I start fucking you."

I take my dick and tap her lips. "Open up."

She opens her mouth and I push in. I am not huge. Just under 7" but a tad thick. I push in and tap the back of her throat. She gags a bit. I back off and push back. I give her no respite. I told her I was face fucking her and that's what I do.

She is gurgling and gasping. You can hear the slurping sounds as I face fuck her. She is drooling down her face. I keep this up until I see her doing a pretty good job finger fucking herself.

I pull out and push her head over up onto the bed. I grab her legs and pull them to me. Her ass is on the end of the bed. I pour some lube on my dick. "This is probably going to suck for you at first." I tell her. She gets a worried look on her face. I push her legs back. "Hold your legs. On the count of 3." I line up. "1." And I push in hard.

I make it about ½ way in and she Screams. I pull back and push back in hard again getting maybe ¾ of the way in. She is trying so hard not to cry. I pull out and jam myself in again. Jesus she is like virgin tight. She screams out again and cries.

"Please give me a moment. PLEASE. You are a tad thick and it's been years." And the tears flow.

I stay buried in her. "I guess you should have replaced the dildo."

"Yes I should have." She cries.

I give her three good Hard full strokes. She has a death grip on the bedding. She gasps and screams out again crying. I stay buried deep again.

"Do you need more lube?"

"No I need to get used the having sex. I feel like a virgin again."

"Then let's have sex. I will tell you it feels Great to me." I grab her hips. I fuck her for about 30 seconds. Tears are still flowing. I bury deep in her and stop.

"I will give you a choice. I have my way with you here and now. Fucking this amazingly tight pussy and cumming in you twice and when I fuck your ass I promise to be gentle. Or I fuck your ass now. Hard and fast like I am doing now until I cum. Then fuck you pussy like I am now until I cum a second time."

I start fucking her pussy hard again for about 30 seconds. Grunting and gasping loudly but no answer yet and for that matter no new tears. I stop again. "So what's the answer?"

"Do you promise to be gentle next time with anal?" She asks.

"I promise."

"Anal another time. Please just fuck my vagina."

I fuck her hard again. I am not going easy. She is grunting loudly with every stroke. I stop again. She thinks I am stopping for her but it's for me too. She is so tight. I wouldn't last for 2 straight minutes.

"Vagina? Vagina? No this is you Pussy, Cunt or Muff. We aren't in medical school. We are fucking." I give a small push "and this isn't my Penis. It's my dick, cock, hardon but not Penis. What's stuck inside you right now?"

Jen looks at me "Your dick."

"Where is my dick?"

"In my pussy."

"Good girl." I start fucking her again. "Now this time I am not stopping. I am going to fuck your hot, wet and extremely tight pussy until I cum. I am going to fill your cunt with cum."

"Oh god no please. I am not on birth control. Please no."

I grab her thighs to me and start fucking her hard. The groaning in pain has been replaced with what sounds more like pleasure and there is a wet spot on the bed. "Tell me the truth. You are enjoying this now aren't you?"

She gasps a bit. "Yes I am. It's been so long."

"Are you going to cum?"

"Yes I am close."

"Rub your clit. Make yourself cum. I want to feel your pussy cum as I fuck you." I tell her. She reaches down and starts rubbing.

Jesus she is so tight. I am not making it long. I keep fucking her with hard steady strokes. She starts gasping louder, her whole body locks up and she groans "FFUUUCCKKKK!"

I have never in my life felt a woman grip me so hard. I couldn't help it I came right behind her. Rope after rope of cum shoots inside her pussy as I hold myself deep in her squeezing cunt. I stay against her for a minute to catch my breath and enjoying my orgasm as Jen does the same.

Her head pops up with her eyes wide. "No. No. No. You came in me? I told you I am not on birth control."

"Yes you did, and I don't care. Leave here and get Plan B and tomorrow call your doctor to get on the pill. I will cum in your cunt, ass, mouth or on your face. I will decide where and when."

She just moans. "Can I get up and go to the bathroom?"

"Sure." I pull out and step aside. She half rolls off half falls off the bed and walks into the bathroom. I sit on the edge of the bed and I notice her plain white bra and underwear. I walk over and pick them up to check the sizes. I then sit and go to my favorite lingerie website. I order 10 different styles and colors of lace bras, panties and thongs. Then for good measure a few different sexy baby dolls and lingerie.

Just as I am finishing Jen walks out. "What's your street address?"

She looks up at me and then sighs and tells me. I place the order. I pat the bed for her to come sit. I hand her my phone with the order up.

Her hand covers her mouth. "Why so much." She asks me.

"After they are delivered you are going to throw out all the plain Jane shit. You are to never wear any underwear that isn't like this."

"I have never worn a thong. Wait I can't workout in this stuff." Jen says

I look at her a bit surprised. "You work out?"

Jen giggles. "Yes. I do yoga once or twice a week with my daughter. It helps me at work. I don't feel as stiff at the end of a hard day."

"Good for you. I thought it was the job keeping you in shape."

Jen actually blushes. She drops her head. "Thank you."

I push towards the middle of the bed. "So let's see how flexible you are." I grab her ankles and spread her legs wide. She smiles at me and spreads them wider. I take them and push them back. She takes her legs and pulls them back. She gets her feet to her face.

"My daughter Lisa can put her feet behind her head." Jen says.

"Now there is a thought. Mother and Daughter side by side spread eagle for my pleasure."

"Don't even think about my daughter." she growls at me.

I jump up her body and grab her by the neck pinning her to the bed. I get my face close to hers and growl back. "Don't You Ever Speak To ME Like That! I am trying to be nice and get you a better paying job and you act like This? I could just as easily get you fired from the job you have now. How far would you get on unemployment?"

Her arms are trying to pull my hand away but she can't. She is trying to say something but I am holding her so hard she can't breath. She gets out a choke or two. I release her neck and she gasps in I big gulp of air choking and gasping.

I am off the bed and reaching for her. I grab her by her nipples to pull her to me off the bed as she starts to say "I am sssoooorrrryyyy. Ow ow ow that hurts. I am sorry." As she gets up to prevent me from ripping her nipples off. I pick up her panties and shove them in her mouth. I grab her bra and wrap it around her head to hold the panties in her mouth and tie it.

"I really thought this could be a nice first fuck, but No. You have to be a bitch and speak to me in that tone. This is no longer a show of good faith meeting. This is you being punished for being nasty to me."

She tries to talk but she is muffled.

I look straight at her. "I don't need to hear your whining. The answer is simple. I am going to spank you right now for your tone of voice. You can do one of two things. You can bend over the bed and accept your punishment tonight. And we can reschedule the 'Show of Good Faith' this was supposed to be. Or you can pick up your clothes now and leave. You will not get the corporate job and I will have to have a long talk with your store manager about your future."

"Mmm mm mmm."

If I had to guess it was I am sorry. I grab her chin and hold it in my hand while I glare right into her eyes. "Actions speak louder than words. Choose." I let go of her chin and step back.

She stands staring at me for a minute. Her shoulders slump and she whines something but she turns and bends over the bed.

I stand beside her "You attempt to evade any hit and we are done and I leave. You will stand here and take what I dish out. I will tell you when we are done spanking your ass."

I step back and with no warning I spank her ass hard. I rain down 6 very hard hits alternating left to right, top of the cheek and bottom. She SCREAMS the entire time, and tears are running down her face. "Who the fuck are you yelling at me?" 8 harder swats. The screaming and crying hasn't stopped. Her ass is covered with overlapping cherry red hand prints. Her eyes are squeezed shut, and are soaked with tears. Her nose is running. I end it with 6 more hard hits. I grab my phone and take a picture of her red ass.

I push her against the side of the bed and push myself in and fuck her hard. She screams into the gag still in place. I grab her hips and she screams again as I grip the sore skin. I keep fucking her. I do my best but I last 3 maybe 4 minutes and her pussy has me ready to cum. I push in. Trying my best to rub myself against her sore skin and I cum in her.

I pull out of her and she half slumps to the floor. I use the bedding to wipe my cum and her juices off me and step over to my clothes and get dressed.