Working for Miss Monica

By Mike

During college I worked at a small private convenience store owned by you. Without my knowledge you installed a video camera watching the cash register. You noticed I was selling beer to my friends who are underage and also helping myself to beer when I closed the store. Not wanting to lose your liquor license you confront me about selling beer to minors. I deny everything. You show me the video and fire me on the spot. But I need this job and beg for another chance. You agree to give me one more chance as long as I visit your house tonight for "training".

I arrive at your house that night, you explain to me I am to be punished "until I will never consider selling to minors again."

You tell me,"If you do not follow my orders, you will be fired, now remove all your clothes and follow me into this room."

I take off everything as you inspect me up and down. I'm feeling nervous, exposed, and wondering what I've gotten myself into. You are wearing tight blue jeans with a nice blouse and the normal friendly personality you have is now stern and slightly pissed.

"Follow me," you order. You take me into a den with a large desk that you sit behind. You order me to sit in a chair in front of the desk. In the center of the chair is a large, hollow, dildo.

I pause and you sneer, "I told you to sit down! Here is Vaseline if you think you need it."

I smear Vaseline on the dildo and aim it towards my butt hole. You have a little smile as you watch me force the dido up my ass until I am fully seated in the chair.

Pleased you say, "Good, now I have some questions for you."

That is when I notice the large four quart enema bag hanging behind you. You explain this enema bag is filled to the rim with hot soapy water spiked with lemon juice, and the hose is connected to the dildo I just sat on. Then you show me the clamp on the hose and open it.

I immediately gasp as I feel the rush of water gush inside me. The flow is fast and I get a cramp. You close the clamp.

"We both know you sold beer to minors, anything else you need to confess?"

"No ma'am," I reply.

You open the clamp. "I have been watching you for some time. I guess I'll let the enema flow until I hear all about your transgressions."

I am feeling very full and getting fuller. The cramps are more frequent and the bag is still half full.

"Okay, okay. I also stole beer from you!" I desperately yell.

You close the clamp. "I see. How much beer have you stolen?" You open the clamp. The pressure is intense.

"I'm not sure, maybe ten, twelve packs."

You close the clamp. The bag is close to empty and I am way past full. "OK, after you expel the enema you will be spanked one hundred times for selling to minors and one hundred times for steeling from me. Trust me I SPANK HARD!!! Now get to the bathroom and return as fast as possible."

I slowly stand up, pulling myself off the dildo, my stomach distended and cramping. As I walk to the bathroom I see you pick up a large, oiled, leather strap.

"Hurry up, your real punishment is about to begin..."

I return from the bathroom feeling relieved and empty after expelling the enema. I see you are now wearing a short nightgown.
You tell me,"I made myself more comfortable, now I'm going to make you very uncomfortable." You are standing next to a sturdy spanking bench, made for someone to be bent over and strapped down. Laying on a table are several painful looking implements. I look at your fit bare legs as you stand there holding an old heavy hairbrush.

You look down and notice my cock has become erect. "This will not do!!! You are being punished, this is not for your enjoyment!"

You tell me you know how to take care of me being excited. You sit down in a straight back chair and tell me to rub Vaseline on my cock. I am thinking "all right" as you pull me over your lap and trap my cock between your legs. You explain my enjoyment will be short lived as the hairbrush crashes into my bottom.

You spank hard and fast as I buck up and down, before I know it I climax between your legs. The next 10 hairbrush swats suddenly hurt much much more. You tell me to stand up and clean you up with a towel.

"Now your punishment will begin. That spanking did not count towards the two hundred you have coming. It was just to get you in the correct state of mind. Bend over the bench."

I climb on the bench and find it is actually comfortable. I am on my knees and elbows with my legs spread apart and butt in the air. You start buckling straps around my legs, arms, and around my back. You show me 4 implements, an old sturdy leather belt, the oiled leather strap I saw earlier, a Lexan school paddle, and a wooden school paddle with holes.

"You are getting fifty swats from each of these. Yell all you want, no one will hear you." You then pick up a bottle of baby oil and apply it to my butt, "just so things stay sensitive."

You pick up the leather belt, double it over, and stand behind me. I feel the first swat of the belt land on my well oiled butt. It stings. I don't have to wait long for the next swat as you start whipping hard and fast.

I wiggle my rear and try to stay stoic but the heat and pain builds fast. Then I notice a mirror on the wall that lets me watch you spank me. You are picking the belt up high and swinging hard. I am trying to count to myself but am not sure of the number of strokes so far.

My wiggles get more violent and I start to yell with each stroke. The pain is getting intense as you crash the belt into my rear. Then you stop and say, "Fifty".

I try to catch my breath as you pick up the leather strap, you show it to me and say, "From experience I know this hurts much worse than the belt. I keep it well oiled and ready to use at all times." You rub my rear a little and comment how RED it already is. "Okay, break is over."

The first swat lands. I yell. You spank. By ten swats I am yelling as the first tear rolls down my cheek. I promise to never misbehave again.

You keep swinging away and tell me, "You earned this! Take your punishment!! Cry and yell all you want."

So I do, as the strap sears my butt I start crying like a girl. I can see a grin on your face as you change sides to even out the redness. Never have I felt my butt hurt this bad.

"Fifty." You stop. You scold me awhile while rubbing my rear, reminding me why this is happening. You apply more baby oil to my red swollen cheeks. You laugh at how messy my face looks as you pick up the Lexan paddle. "Half done, this is really going to hurt."
Then it starts again. The Lexan paddle stings BAD, I just let myself go as I watch this beautiful lady paddle me in the mirror. "I'm sorry!" I say over and over.

"Quit squirming! Take it like a man," you tell me, then finally, "Fifty."

I am really blubbering as you pick up the wooden paddle with holes. "Last set" is all you say as the first swat lands.

"OWWWWEEEE," I scream. You slow down the pace and I hear the air whoosh though the holes with every swat. You cover every inch of my rear and the top of my thighs. I am crying more than I ever remember and bucking uncontrollably, but the straps hold me firmly in place.

Then it is over. You lay down the paddle and start removing the straps. I don't move, I just lay there trying to catch my breath. You wipe my face with a towel, pat my head, and tell me to stay still.

Then I feel you rubbing cold lotion on my rear. It feels so good. You tell me it has been awhile since you have seen cheeks that red and laugh. I slowly stand up, rubbing my butt like it is on fire. As I'm getting dressed you warn me if I ever repeat my offence, it will be much worse next time.

"Worse," I gasp. "How could it be worse?"

You smile and say, " It involves sitting in a bathtub of ice water first, trust me you don't want to find out."

I shudder, and vow to be good from now on...but can I?

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