Role-Play: Caught

reader: as always, appreciate your feedback.

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We ordered our dinner and resumed our conversation as the waiter walked away. Talking about how our day went, what was happening at work, and all the little things we wanted to catch up on. I loved Jenna. No matter what the pressures of my job, I could easily unwind talking with her over a drink and the worries of the world would melt away.

An hour and a half later after a few more drinks, sharing an appetizer and dinner we were getting ready to leave. As I paid the check Jenna handed me a small piece of paper.

Unfolding it I read, "shoplifter caught". That's all I needed to know.

As we walked the two blocks to my apartment, I held her close with my arm around her waist. We had gone to the restaurant directly from work, she met me at my office and we took the train together. She was dressed in a fairly conservative blue business suit, white blouse, sheer stockings, 4 inch blue heels and carrying her purse. While appropriate for the office, the outfit was also quite sexy in that buttoned up businesswoman kind of way. Neither of us mentioned the note on the way home.

Once in the apartment I put my briefcase away, hung up my suit jacket and tie and put on some music. If there was going to be a "scene", that "scene" needed a soundtrack. I always give a lot of thought to the soundtrack. Slow or fast, soft or loud, the music in the background really helps set the tone. Tonight I wanted something that we could get lost in, something that was just instrumental with no vocals to get in our way. I decided on some Miles Davis. Nobody ever went wrong choosing Miles Davis.

She was standing in the living room, still dressed as she was and still holding her purse. I walked over, put my hand on her shoulder and said, "excuse me miss, I'm with store security and you need to please come with me."

"Leave me alone, I'm not going anywhere with you," was her response.

I increased the pressure on her shoulder, guiding her toward the bedroom (uh, I mean the security office) as I told her "we have a matter to discuss in private, or, together with the police."

The look on her face changed from one of confidence to one of apprehension. She offered only token resistance as I took her purse from her with my free hand while leading her to the security office with my other hand.

Miles was just getting warmed up.

Once in the office I explained that the store had recently had a rash of shoplifting and the management had doubled up on security with the intention to deal harshly with any offenders. I emptied the contents of her purse on the desk and started looking through them.

"What do you think you are doing? You have no right to go through my purse".

"Actually I do have the right. And you need to behave as I look for evidence."

I held up some cosmetics: lipstick, mascara and blush. "Now do you want to explain how this product ended up in your purse?" I asked.

She was now starting to realize that she was caught. The confident tone was gone and her body language was definitely that of someone realizing they were in trouble.

"OK, I'm sorry," she said. "I don't usually do this sort of thing but I left my wallet home and I just needed a few things." "Please let me go home and get some cash and I will pay for all of this."

"Well, its not quite that simple," I explained.

I reached into the desk drawer and produced a set of wrist cuffs. Her facial expression again changed, this time it was fear. I explained that I was going to have to restrain her as we waited for the police to come. I further explained that she should save any excuses she had for the police; they would take a statement from her before taking her to the station for booking.

She was mumbling incoherently as I attached the wrist cuffs securing her hands in front of her. She was still mumbling as I walked her over to a wall and attached her cuffed wrists to a hook in the wall about a foot over her head. Her face was up against the wall and she was crying as I told her to stay where she was and I would be back in a few minutes. She was outright sobbing as I left the room.

I stood right outside the office a few minutes, taking in how her crying was melding with the music. "Miles would be proud", I thought.

As I walked back into the office she tried to follow me with her eyes. She could, however, only turn her head so much. I told her how I needed to get my report ready before the police showed up and asked her if this was all she stole or if there was anything else.

"That's it, just those few things, please, can't I just pay for this and apologize?'

"Sorry, that's not how this works. I wish I could take your word for it but I am going to need to do a search to see if you have anything other merchandise."

I walked over to her and put my leg in between her legs and forced them out a bit from the wall and apart. I moved my hands around her neck, teasing as I let my fingers investigate under the collar to her shirt.

"Noooooo." She screamed. "You can't do this to me."

I was getting a bit annoyed now. Here she was, a shoplifter caught red-handed and she was telling me what I could or could not do?

I pulled my hand back and gave her a strong smack on her ass. "You do not tell me what happens now, I will tell you." "You have stolen merchandise and you will pay for it, perhaps this will teach you a lesson."

Her crying was getting louder. I was not in the mood to hear it. I picked up a bright red ball gag and, before she ever realized what was happening, I had it in her mouth and fastened behind her head.

I smiled, she cried, as I resumed my search. I reached around and opened her suit jacket, letting my hands brush against her tits. She was squirming around, trying to utilize whatever limited movement she was allowed. I grabbed both tits roughly, pulled her into me and said, "stay still or you will regret it."

She stopped moving. She looked at me for a second, fear written on her face. She then just looked down and cried into the gag. I continued my search, tracing around her tits, lifting them by the nipples and searching underneath. I knelt down and ran my hands up her legs. Slower and firmer as I got to the inside of her thighs.

The crying was subsiding now but her breathing was getting much faster and heavier. Panting almost.

My hands now were at the top of her stockings, my fingers inspecting the straps to her garter belt. I had the skirt to her suit up around her waist now and I was running my right hand up and down between her ass cheeks while my left hand was finding its way to her pussy.

"Do you know why this is necessary dear?' I asked her.

"Because I stole." She mumbled through the gag.

"And what happens with shoplifters who are caught with the goods?"

"They are punished." She grunted. "To teach them a lesson." She added.

"Very good." I said. "Now if you want to avoid the police I can handle the punishment right here, right now."

"Yes" she blurted, "Please."

"Please what?" I asked as I continued working my hands, front and rear.

"Please punish me." She begged. "Please teach me a lesson, however you wish."

I stood up and reached around her. I ripped her shirt open and lifted both tits out of her bra. Leaning into her, pressing her against the wall, I held both nipples between thumb and forefinger and began pinching. Her nipples were reacting, getting hard and tight. I twisted them roughly as she moaned into the gag and threw her head back.

I played with those nipples for quite awhile as she bucked back, thrusting her ass into my now rock hard crotch.

"Owwww, punish me." She cried over and over again.

I stepped back and looked at her for a moment. She was beautiful in that suit, in that position, in that state. I tucked her skirt in the waistband to keep her ass exposed as I Took off my belt. Before she realized what was happening, my belt connected with her ass leaving a nice stripe on her white ass and eliciting a gag muffled scream from her.

I whipped her with the belt for about 15 minutes. She tried to move around as best she could to avoid getting hit in the same spot twice. She was throwing her head from side to side, her breathing was deep and rapid and her ass was turning a nice shade of red.

I reached up and took the cuffs off the hook. I put her on the desk and, using another pair of cuffs, I attached each wrist to an ankle. She was breathing even harder now, as she realized she was completely open and vulnerable. I let the belt fall gently between her legs. Brushing her pussy letting her know just how vulnerable she was.

I raised the belt and I could see her face contort. Her eyes closed as she anticipated the strike.

There was no strike. As she opened her eyes I was between her legs, my tongue licking up and down her slit. She was so wet and tasted so good. I stole a glance to see her eyes closed again and her head back. Her moaning louder now she was bucking her ass thrusting her pussy up to meet my tongue.

"Ahhhhhhhhh." She screamed. Even the gag couldn't stifle that scream as she came.

I took off the cuffs, and the gag. Lifting her off the table and onto her knees. I had a fist in her hair as I sprung my cock. I guided her to my balls and she licked and sucked them feverishly.

Now my breathing was picking up. My balls were aching for release. The sight of her, half wearing her suit, ass crimson red and servicing my cock was incredible.

She moved up the shaft and licked the head of my cock. Obediently, circling with her tongue. Slowly drawing me into her hot lipstick smeared mouth.

I renewed my grip of her hair as I rammed home. She sucked and sucked as I pulled on her hair and slammed my cock in and out. I held her tight as I rammed in to the hilt and came in her throat. She swallowed gulp after gulp.

As I leaned against the table she licked me clean.

"I've learned my lesson." She said. "Crime pays."