Locked out, a memorable cross dressing experience

I occasionally use my private small business office as a base for cross-dressing operations. I arrive as a man and leave as a woman, carefully checking both coming and going to make sure the other tenants or customers do not see me. One time in late 2013 nearly ended in disaster, but I now look back on it and smile.

I arrived one winter's day with a large bag of clothing and accessories and took my time dressing and applying makeup. It was one of my better efforts to date – a corseted, hourglass shape shown to good effect with a form-fitting black sweater dress; black tights; silver jewelry; long light brown wig; a form-fitting black leather coat and matching gloves; a small black shoulder purse for ID, keys and phone; and spike-heeled, knee-high black boots, extremely sexy footwear but rare for me since they are difficult to walk in. My makeup application was very convincing, and my newly-learned smoky eye treatment looked fantastic. But then came the most risky part – leaving the office without being spotted. I had it carefully planned: Make sure the coast was clear, and in a quick series of motions lock the business door, pop my car trunk, throw the bag of male clothing into the trunk, hit the door unlock remote on my car key, jump in the car, and drive away. I had done it before, and it had taken literally 15 seconds from start to finish.

Ready, set, go. I made sure no one was around, locked the business door, popped the trunk, threw my male clothing into the trunk and shut it, then high-heel click-clack scurried to the driver's door and realized I had forgotten to unlock it. No sweat, just grab the key and remote. Except the key was not in my purse. Or my coat pocket. Or my hand. I quickly checked the sidewalk, thinking I had dropped the key in the rush. No luck. It took me a few seconds to realize that I had locked my car key and remote in my trunk when I tossed in my male clothing. This was a true “oh shit” moment – no transportation, no male clothes, and I was outside at a public place where at any moment my business partner, another tenant, or a customer could appear, none of whom would know about and probably would not understand why I was dressed as a sexy woman.

Luckily, I had placed my office keys and wallet in my purse after locking the office door. I went back into my business so at least I was out of view from prying eyes. Since my only extra set of car keys was at home an hour's drive away, it became apparent that I would need to call a locksmith to get me into my car. That meant communicating up close with what would likely be a working-class man to prove that this woman standing before him was the same as the man on my driver's license and vehicle registration. Furthermore, that same she-male would have to pay for the locksmith's services with a credit card bearing a man's name. But what could I do? I started calling locksmiths, and finally reached a live voice. I explained my basic predicament, that my keys were locked in my car, but then ended the conversation with, “I'm going to a costume party, so be looking for a man dressed as a woman.” It was the weekend before New Year's Eve, so this excuse was actually somewhat plausible.

Sure enough, it was a working class man who showed up. I waited inside my business until the last possible second and then walked out to greet him in the parking lot. I could see him sizing me up, and only when I spoke did I see a huge grin spread across his face. “Damn, you weren't kidding!” he said. I was anxious to get the ordeal over with so I could get out of there, but with modern anti-theft car protections, plus his desire to discuss my outfit and makeup and how I could make myself look so good, it proved to be a rather lengthy affair. At one point he tripped the car alarm, so there we were, working man and sexy woman, standing in a parking lot in broad daylight with the car alarm going off. Finally, he got the car open, I retrieved my car key, deliberately and carefully put it in my purse, then I invited him inside the office to pay him (it was warmer there, and it also meant less exposure for me). He left smiling with an admonition to enjoy the party.

I wasted no time, as I had pushed my luck to the breaking point, so I locked the office, firmly grasped my car key, got into my car, and drove away. I had done it! I had survived what could have been the most embarrassing day of my life, and had given someone else a day to remember. I decided to celebrate with a Starbuck's coffee (drive-through, of course – didn't want to press my luck). But after ordering my coffee and while waiting in the drive-through lane, who walked out the door of Starbuck's and directly in front of my car? You guessed it – Mr. Locksmith. He smiled, waved, and winked. I returned all three greetings.