Undercover Assignment                       by: Ray Kitten

 

As I got out of the car and approached the door I was all too aware of the sound of my little hard soled shoes tapping against the sidewalk. I could not believe that I was actually going through with this stupid bet, but I really had no choice.

I had been wanting to propose to my girlfriend for months, but didn’t have enough money to buy her the quality of ring that someone as beautiful as her deserved. I saved for almost six months, and still didn’t have anywhere near what I would need. It would take me at least a year to save up enough money for her ring, but there was no way I wanted to wait that long before proposing to her. One of my co-workers told me about some college friends of his who had a poker game. He sometimes sat in on the games but wasn’t going to that weekend. He offered to phone and let them know to expect me if I wanted to go.

To make a long story short, I not only lost all the money I had saved up for her engagement/wedding ring set but ended up owing several of the guys at the game money before they finally cut me off.

I was devastated, this game had set me back nearly another year’s worth of savings. Two years, It would now be two whole years before I could prove to my lovely Darlene that I wanted to be with her forever. This depression made me an easy target for two of my biggest creditors. They offered to buy my debts off all the others and even give me a way to get all my money back with an added bonus. Depending on how I did, maybe even enough extra to buy my rings.

"How would I earn you back?"

"What would I have to do?" I aksed.

"Nothing much," They assured me, "Just take a simple dare."

When they told me what I had to do, I was very leery at first. If it would get me my money back I decided I’d do anything, even what they wanted.

And so that was how I found myself in this ridiculous predicament. Dressed in a school girl’s outfit, The blouse wasn’t that bad, it was cotton, and not something like silk, except that it was fairly puffy with full length sleeves and imitation pearl buttons at the cuffs. Unfortunately there was a large floppy bow at the neck of the blouse in a green and black plaid to match the skirt that went with the outfit. And a matching ribbon in my past shoulder length blonde wig. Knee high socks and those tapping little shoes graced my feet.

The girls who my creditors had gotten to help out had done a wonderful job of disguising my face. Between the wig, the humiliating outfit, fake eyelashes, blusher and coral pink lipstick no-one who didn’t know me would ever think I was a guy.

Taking a deep breath I finally stepped up to the door of the liquor store. It was a tiny mom and pop operation, so small that the two staff members on duty could see everything that went on in the store. There was one guy behind the counter, he looked like he was probably in his early twenties just like me, just old enough to drink. The other was another guy a few years older but in better shape, he was roaming the floor helping people and keeping an eye out for shoplifters. There were at least a half dozen customers in the store too. At least that would draw attention away from me.

My creditors had quite clearly warned me that one of their friends would be here to see to it that I completed my assignment as they had instructed. I would know him by his tongue ring . As I slowly approached the back of the store where the wine was kept, I could feel all their eyes upon me.

Here it was a Saturday night, and a customer walks into the store wearing a school girl outfit. I could only hope that I appeared convincingly as a girl, I knew I would die of humiliation if they knew I was a guy under this skirt. Reaching the wine racks I bent over to look at some of the wines on the bottom shelf, as I had been instructed, bending at the waist so that my skirt rode up and my lacy white panties where on prominent display to anyone behind me.

I dared not stand up for a minute, having been warned to give everyone a nice long look at my frillies, so I just scanned the wines. Just then, as I was about to grab a bottle, I felt a hand pinching my bum. I gave a startled squeak, barely remembering to keep my voice high and airy. I turned around to see a group of three young kids, none of whom looked old enough to drink.

My face went absolutely red as the one who had pinched my bottom smiled at me, "Nice panties sweetheart,"

I was tempted to ask if he liked them so much maybe he would like to be the one wearing them. But I refrained, merely smiling sweetly at him, and mumbled a high pitched, "Thanks,"

I then moved down to the next rack of wines to get away from them. Unfortunately, when I got there I had to bend over again. Why had they specified that I had to get a wine from the bottom shelf? Once again, as I bent over I felt the young guy’s hand on my butt. I was furious, but at the same time petrified.

I didn’t dare speak to him, every word I said while I was in here risked giving me away.

I was also positively mortified by the vague feeling that his crude gesture was in some way justified by my apparent flirting with him by flashing glimpses of my unmentionables. Fortunately the floor worker came over to ask these boys for ID. They offered some lame excuse why none of them had any.

I just tried to get away from them before he decided to ask for my ID as well. I had been specifically instructed that if anyone asked to see my ID I was to present it immediately with no argument.

I went two racks down and bent over one last time to inspect a new batch of wines. This time I picked one and grabbed it. I allowed myself a small sigh, that part of my assignment was out of the way. Now I just had to get the other two items, neither of which would require bending over, and pay for them.

As I stood up another customer came up to me, "Are you all right miss, I saw those guys giving you a hard time?"

Forcing my voice into the light airy female sound that I had been practicing all day I replied, "Yes, I’m fine, thank you."

He tried to make chit-chat as he looked me up and down, I’m sure trying to puzzle out why I was wearing a schoolgirl uniform at 8 o’clock Saturday evening. I’m also pretty sure he was trying to flirt with me, playing the concerned nice guy routine. I had used that routine before I met my current girlfriend and knew how it went. I tried not to speak, afraid of giving away the fact that I was a guy. My knees were shaking uncontrollably underneath my skirt, I was almost sure that he was going to clue in at any second. Either that or try to kiss me. Believe you me I desperately wanted to avoid either one.

Finally I came up with a ploy to get rid of him. "I really should get going," I made my excuse, praying that my true voice wouldn’t show through this girlish facade. "My boyfriend is waiting for me. We’re going to a costume party thrown by a friend," I’d added that last part as an afterthought, although it wasn’t really very believable. Who threw a costume party except at Halloween?

I scuttled away , skirt swishing as I walked and thinking, "damn it, how did women get used to that?" It tickled my legs something fierce. I went to the back and picked up a 12 pack of Miller from the cooler. Two items down, one to go I told myself.

More customers had come in than had left as I had been conducting my business and fighting off advances from what seemed to be half the men in the store. I wondered if I could be called that anymore? I mean, would any real man be caught dead wearing an outfit like this, let alone in public? Sure they would, if they were in my position, I reasoned. It wasn’t like I wanted this or was enjoying it.

Then I picked up a 26 ounce bottle of vodka and practically ran up to the front. Keeping my eyes downcast so that the cashier wouldn’t see my face I placed all my purchases on the counter. After a moment the cashier still hadn’t rung the order in, so I ventured a glance at his face. He smiled at me and opened his mouth a crack to flash me a glimpse of his tongue ring.

My heart jumped into my throat as I realized this was their man in the store. I pleaded to him with my eyes, begging him not to embarrass me, but he just grinned hideously as he said those dreaded words, "May I see your ID miss?"

I tried to keep from hyperventilating as I reached with shaking hands into the purse they had given me and withdrew my ID. It was MY ID not a fake set made up with a girl’s name and picture on it. My heart raced as he took it from me.

"I’m afraid I can’t serve you unless you give me YOUR ID," he started, then appeared shocked as he looked at my face. Tears were welling up in my eyes, imploring him not to do this to me. "This IS your ID!"

"You’re a guy!" He cried out in shock, clearly louder than was necessary, loud enough that the whole store could hear him and faking shock very well. Then he burst out laughing. His voice was joined by others, the whole store was busting a gut laughing at me. I think at that point I must have looked like a deer caught in the headlights of a truck, scared, lost helpless, and too frightened to move.

Finally I managed to get my legs working, and I panicked, I ran! I flung the money at him and ran from the store, tears streaming down my cheeks, making my mascara run. As I ran for the car that was fortunately still waiting for me, I heard the cashier crying after me about my ID, calling out my real name.

I jumped into the car with the echo of their laughter still ringing in my ears. That was when I realized that I had left the booze lying on the counter. Booze I had paid for, and I knew there was no way I was going back in there.

I couldn’t bear to show my face to any of those people again, especially now that they not only knew what I was but my name as well. One of my creditors fixed his eyes on me and asked the question I feared now "Did you get the stuff?"

 

The End???

Thanks for reading this feel free to send me an e-mail at spottycat44@hotmail.com and tell me what you think, as this is my first attempt. I may even continue this storyline, if there is enough interest.

 

 

 

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© 2001 by Ray Kitten. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.