The Challenge
When people find out that I’ve been a shoplifter, they’re always confused. Why would a girl from a wealthy family ever need to steal anything? After all, I always have my Daddy’s credit card, don’t I?
Well, that’s true. But what they’ll never understand is just how thrilling it can be to steal stuff, especially from the fancier stores. There’s just something really special about paying them back for overpricing their goods in the first place just because some people were born lucky and can afford it. It’s a form of natural justice if you want to think about it that way.
But the truth is that shoplifting is also a sexual thrill for me. Not even my psychologist can really explain why it just gets my pussy so wet whenever I nonchalantly stroll past a security guard with stolen items crammed into my tiny little handbag. All I know is that it started when I was around 12 or 13, and it’s been that way ever since.
I can’t quite remember the very first time that I ever stole something, but I remember picking up some lovely earrings from a shop at the mall when I was in junior high school, slipping them into the tiny pockets of my jeans, my heart racing a mile a minute.
I also remember trying them on in front of the mirror at home, getting so hot and bothered that I ended up touching myself. And yet I have no memory of ever wearing them anywhere. I just liked the fact that they were mine and nobody could ever tell me how to dress.
My shoplifting skills really took off in high school. My mother, as usual, would purchase some rather ugly clothes for me every September, but it wouldn’t be long before I was wearing the coolest brands in school. Everyone just assumed that my parents bought my clothes, but the truth was that I had to steal nearly all of them, especially the overpriced trendy stuff that was the fad at that time.
By the time I graduated high school, I had the art of shoplifting down to a science. Whether it was a cute little diamond tennis bracelet or a bulky item like a box of chocolates, I rarely actually paid for anything, preferring the challenge of figuring out how to shoplift the items without getting caught. Over time, I mastered all of the techniques, including how to distract floor personnel and how to disable security tags. And yet I only wore or used a fraction of the stuff, preferring to give it away to my friends in exchange for their loyalty and friendship.
After a while, though, it all just became too easy. I realized, more than a few times, that I was on the verge of becoming a professional thief. I suppose I could’ve gone to work for the mafia or a crime family or something, but that wasn’t who I was. I had no interest in making money from shoplifting or going about it in some kind of organized way. It was just my way that I preferred to steal something when the mood struck me.
I tried to keep it interesting by setting myself up for more challenging thefts, including swiping expensive make-up products right in front of the counter girl’s eyes, but that just didn’t thrill me as much as I had hoped it would. In fact, the longer that I went without getting caught, the more that shoplifting started to become boring for me. I realized that, in some kind of way, I actually wanted to get caught, at least to see how it was.
But, as I said, I am from a wealthy and prominent family, so I knew that getting arrested for anything, including shoplifting, would bring down their wrath on me. And while I had no intention of going to some boring job for the rest of my life, I did need to keep my options open, and that meant keeping my record clean. So I was stuck. I wanted to get caught, and yet at the same time, I couldn’t afford to get caught.
That’s when I started to come up with my master plan. I would go into some store or boutique at the mall and steal something, but something that wasn’t too valuable, and I would let the security guard catch me. The challenge would then be to talk my way out of getting into trouble. At least, something that got my pulse racing again because just the thought of my Daddy having to come bail me out of jail made me nervous.
I’d just have to do some research to make sure I would only steal enough stuff for it to be a misdemeanor. That way, I could still escape with minimal risk even if I did get caught and couldn’t talk my way out of it. Yet whether it was an item worth a dollar or ten thousand dollars, something about the idea of getting caught and then having to get myself out of trouble got my blood flowing in a way that it hadn’t since I was shoplifting earrings back in junior high school.
As part of my research, I visited several malls and just looked around, not stealing anything this time, only scouting out the security guards. Just about all of them were male, and most of them were older, in their 40s or 50s. A lot of them had pot bellies and walked slowly, which meant that it would be a challenge to get them to actually catch me in the act of stealing. But I figured I could use my girlish charm on them to talk my way out of trouble.
After all that research and preparation and sleepless nights going over my plan, I finally went out and did it. I visited the Highgate Mall where a lingerie boutique named Belinda’s was having a sale on panties. I picked up a lovely pair in red lace and then I clumsily stuffed them into my purse right while the guard was watching from the other side of the store.
When he marched over to me and told me to freeze, my heart was racing, and I found myself getting quite sexually excited for some reason. Just as I had hoped, the guard clamped one meaty hand on my arm and marched me into a back office. But just when I was ready to start pleading my case, he just took one long look at me and said I was too pretty to arrest and so let me go.
Of course, I was grateful that I had managed to shoplift something, get caught, and then escape any consequences, but I was more than a little disappointed that it had all been so easy. What I wanted was a challenge. And so, for the next week, I redoubled my efforts to surveil and analyze the movements and actions of the security guards at all the local malls until, at long last, I discovered a way to make the whole process more challenging and, thus, more exciting.
I played with myself for quite a while the night before I executed my plan, so excited with anticipation that I could barely get to sleep. But, as it all turned out, it went even better than I could have ever expected.
