Caught

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Ashleigh is caught in the act.
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This day has been so exciting, I have spent my time anticipating what Harry has planned for me after my shift. I have been worrying that I would expose my pink panties when I bend over or that they could smell the load of cum I had left in them this during my meeting with Harry this morning.

As my shift ends I clean up my work area and close out my register then nervously make my way back up to Harry's office. As I approached the door I pause before knocking, not sure what is to come.

"Come in" I hear through the door.

I open the door and walk through, closing the door behind me.

"Lock the door" Harry says.

I lock the door and turn around, Harry is behind the desk so I start walking towards him.

"Before you come over please get dressed" he commands.

I turn to look in the corner of the office and see the outfit he has chosen for me, it is layed out on the couch by the door. The outfit is different from the one I wore this morning, tonights outfit consists of a fairly short black skirt, a white blouse, a pink bra and a pair of red high heels. I am still wearing the panties from this morning, the cum had dried several hours ago. I strip down and took off my current clothes and sat them on the floor next to my new outfit. When I am down to just panties I put on the new outfit, first the bra which goes on a little quicker than this morning but I still struggle a bit. I then put on the blouse, buttoning it most of the way up leaving the last few buttons undone showing my chest and some of the bra. I then pull on the skirt which is short, it barely covers my ass. Lastly I try on the high heel shoes, I have no experience wearing high heels but give it a go. Fully dressed I again turn and started walking over towards Harry, I am a bit shaky on these high heels so I am sure I look like I have had a drink or two. They are not the tallest heels I have seen, but probably 3 or 3 ½ inches tall.

"Come around to this side of the desk" he says.

So I chang course and walk around to the back side of the desk. Harry is seated in his chair and as I approached he asks me to turn around and pull up my skirt so he can see my panties. As I stand in front of him I turn around and pull up the skirt just a bit to expose my panties, he reaches up and squeezes my cheeks with his hand. His touch feels so good and my little dick begins to spring to life.

"Turn around honey" he commands "and give me a kiss."

I turn around and leaned over him, a hand on each chair arm, to give him a kiss. As our lips meet I can again feel his hand up my skirt, feeling my ass over the panties.

"I need you to pull down my pants" he commands "take them down so that we can proceed with the next step in your punishment."

I look down at his crotch and moved my hands off the chair arms to undo his belt and zipper, then I pull down his pants and boxer shorts exposing his mostly limp but quickly engorging cock. His penis is different from John's in that his balls and crotch area are fully shaved, I have never seen anything like this. With his pants on the floor I begin playing with his cock, rubbing my hands along the shaft and feeling it harden more with each stroke. Before long he is fully erect, I am guessing his cock is a thick 8 inches. As I stroke the shaft with my hand he reaches over to the desk and grabs something, he then reaches over to me and says "you will probably need this, please use it to lubricate my dick for what is to come."

I am not totally sure what he means, or what is going to happen. He has handed me a bottle of lube and a condom. I look at him and then down to his fat cock in my hands, I remove my hands and kneel before him, I open the condom package and place it over the head of his cock, rolling the condom down the length of his shaft. I then open the lube bottle and and hold it over his cock and squeeze. Lube covers his cock and I use my hands to spread it up and down the shaft, after just a few drops his cock is very slick and my hand moves along the shaft without much friction.

I now believe I know where this is heading and am very nervous.

Harry stands up from his chair and stands in front of my, my eyes are a cock level and I am gazing at his erect condom clad member.

"Now" he says "stand up."

I get up off my knees and stand before him, with the heels on I am almost as tall as he is. He takes me by the waist and pulls me towards him, he leans over and kisses me deeply. His tongue interacts with mine as his hands caress up and down my back and down to my butt. I can feel his cock pressing into my stomach.

As we kiss he backs me into the desk and I can feel the table top edge press into the backs of my thighs, he continues to move forward and I sit on the desk and lean back. Before I am on my back he stands up.

"Turn over" he asks.

I turn over on the table top, resting on my arms and elbows with my ass towards Harry. I can feel his hands on my ass as he moves them along my curved buttocks, then he slips them down on to my thighs and back up under the skirt. I can feel the skirt as be moves it up and over my ass, with the skirt up around my waist I can now feel him as he pulls down my panties. As the panties are pulled down I feel my dick as it is now free, the tip presses into the cold metal side of the desk. Harry takes down the panties fully, as they reach my ankles I step out of each leg of the panties.

I look back as best I can to see what is happening, before I can see Harry behind me stroking his cock with one hand making sure it is fully erect.

"Reach back and spread your cheeks for me sweety" he commands "I am going to make you a woman."

"I have never" I start to explain.

"I know" he says "Don't worry I will make this as painless as I can."

With my ass cheeks spread exposing my hole to him I can feel as he places one hand on my ass, then I hear him whisper something. I look back at him and he places the wadded up panties in my mouth.

"You might want these for this next step," he says.

With his hands on my hips he pulls me back and I can feel his cock as he positions it at my ass hole. I can feel the warmth of his cock head as he begins to push it into my ass, I can feel him struggle as my ass will not accept the size of his cock. He pulls me harder by the hips and pushes his cock into my hole, but it will not go. I can begin to feel my hole being stretched by the pressure of his cock against it, it starts to hurt.

"Relax honey" he says "this will be easier if you can relax."

Tears form in my eyes due to the pain I am feeling, he is trying to hammer his cock into me and each time it seems to stretch me wider and hurt a little more. I moan into the panties each time he tries to push into me, the panties muffle the sound of my moans. After what seems to have been forever my hole seems to have stretched to its maximum, the pain is intense and I try and relax but I can feel the tears that are streaming down my face and relaxing is not easy. All of a sudden his cock makes its way into my ass hole, as it does I let out a muffled screech. Harry lets out a big groan.

"There we go" I can hear him say.

With his cock now in my ass he continues thrusting back and forth, slowly allowing his cock to enter further into me until he seems to be fully inside me. I can feel his cock filling me, it is an odd and new sensation - different from anything I could have imagined. Once he reaches full penetration he begins pulling out and then re-entering me, back and forth slowly at first and then picking up the pace as I am able to relax my ass and allow his cock to move more freely.

He settles into a rhythm of thrusting in and pulling out and as he does my cock also settled into a rhythm bouncing back and forth, I can feel his balls swing up and slap into me when his cock reaches full penetration. This fucking goes on for quite a while, I can feel his cock sliding inside me causing feelings I have never had before. My mumbled moans mix with his grunting as he pounds my ass hole, suddenly his thrusts slow and I can hear his breathing change and suddenly he pulls his cock out of my ass and in his heavy breathing he asks "turn over for me."

Without thinking about what I am doing I stand up and and turn around, and Harry moves closer to me and begins to unbutton my blouse, when the buttons are undone he removes the blouse from my shoulders and then each arm, throwing the blouse on the ground next to the desk. He then leans down and begins to kiss my chest, I can feel the excitement as his lips touch my skin. He then takes his time to remove each of the bra straps from my shoulders, allowing them to fall to my sides and I take free my arms from them as he pulls the bra cups down exposing my nipples. He slowly circles each nipple with a finger and then moves his lips down and kisses each one, my cock is so hard and leaking pre cum. He then pushes me back onto the desk, my feet come off the ground as my back lays flat on the desk. Harry then lifts my legs up in the air and spreads them to expose my ass again, he lays my legs up over each of his shoulders and moves his cock closer to my waiting ass. He uses my thighs to pull himself closer and then into me. Slowly at first and the quicker pushing in and pulling out of me for what seems to be an eternity, my eyes closed as I enjoy the deep penetration of his cock.

Without thinking about what I was doing I reach down and begin to play with my own cock, I am so hard and wet so my hand slides up and down the shaft easily. My head is so sensitive and sends shocks through my body as I play with it, circling the head with my fingers feeling the wetness.

"Go ahead honey" I can hear him say "I want you to cum."

I begin to rub my cock in rhythm to his thrusts as he fucks me, it doesn't take long and I explode all over myself. I shoot cum across my abdomen but most is absorbed into the skirt pushed up to my waist. I continue to stroke the shaft as Harry slams my ass, my body moves each time his thighs slam into my ass cheeks and I can feel his ball sack as it sways and hits my ass between my cheeks.

Eventually I can feel his rhythm change, it has been my experience that this means he is close to cuming. He pulls his cock from my ass and steps back, he looks at me and I can tell he wants me off the desk and in front of him. So I sit up and then get off the desk and squat down in front of him, I reach up to take his cock in my hand and as I do I look up at him.

"Pull off the condom" he commands.

I roll the condom down off his cock and it falls to the floor, he takes his dick in his hand and begins stroking it up and down its full length. I lean over and try to take the head into my mouth but his stroking makes this difficult as the head is all over the place, my mouth chasing it tongue slightly out to try and receive it. He uses one hand to push my head back slightly, the other rubbing his cock while keeping it pointed in my direction.

His movements become more erratic as he moans loudly, I look up at him and can see he is nearing completion. I watch as he strokes his cock in front of me, moving my eyes back and forth between glancing into his eyes and watching his hand stroking his hard cock. He eventually lets out a guttural groan of pleasure and he suddenly begins shooting his load all over my face and chest. Squirt after squirt of cum reached me, covering my face with ropes of semen. I don't remember ever seeing so much cum but eventually the cock twitches diminish and the final squirt of cum shoots out, followed by cum that exists his head and runs down the shaft. As he continues to stroke his softening cock I lean over to lick the head and clean up that sperm that has flowed out of his cock.

It all happened so fast that I lost contact with his eyes so I am not sure but I believe he watched as he emptied his load all over my face, after cleaning the cum from his cock I look up at him and he looks to be very pleased with himself. He takes his clean cock and leans over to begin running the head through the cum on my face spreading it around.

I have never taken a full load of cum on my face before, and it feels like quite a lot. I am not sure what to do, so I use my finger to collect the cum and put it into my mouth, eventually filling it. With my mouth full I look up at Harry and swallow his sperm load opening my mouth to show him when it was done. With a big grin on my face I lick my fingers clean of his cum.

"Did you like that honey?" he asks.

"Yes" I reply.

Suddenly there is a knock on the door, I duck down as best I can reaching over to grab his leg and help balance myself. I look up at him surprised thinking we might be caught but he doesn't seem to be concerned.

"Come in!" he yells.

I guess the door wasn't locked as it starts to swing open, I try to keep down behind the desk as not to be seen.

"Good to see you Chuck" Harry says "come on in."

I look up at Harry and mouth to him "what is going on?"

"Don't worry Ashleigh, this is part of your restitutions," Harry says "you are going to please a couple of my friends."

I did not know what to say or do, I felt helpless squatting there with cum on my face and chest and in my hair, skirt pulled up to my waist and bra pulled down exposing my chest.

"Ashleigh, stand up and meet Chuck" Harry says, "he is one of my friends."

"Chuck, where is Andre?" Harry asks Chuck.

"He will be here in a minute" Chuck replies.

I begin to stand up and move around to put Harry between me and Chuck, I pulled down my skirt to cover my cock and ass and then put my arms back through the bra straps and put it back into place.

"Nice to meet you Chuck" I say shyly.

The door then opens again and in walks who I assume is Andre.

"Thank you for joining us" Harry says "this is Ashleigh and she is here to give the two of you anything you want."

Andre closes the door.

"Isn't that right Ashleigh? Harry asks.

I look at Harry and then over to Chuck and Andre, they are both very large men. They appear to each be 6' 5 or 6' 6, both were much taller than Harry and I was a bit scared of what was to come.

Reluctantly I reply "Yes Harry."

"Well Ashleigh, go over and make these gentlemen comfortable" Harry instructs.

I slowly make my way from behind Harry and the desk and walk over towards Chuck and Andre, not sure what is to come.

Ashleigh Swift

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1 Comments
BrendaNWBrendaNWover 4 years ago
lovely

I think Ashleigh is quickly becoming a popular little company vixen :)

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