My boss was going on vacation and asked me if I would house sit for a couple of weeks. Since there was no work during that time I readily agreed. He had a real nice place in the Hollywood hills and I get a vacation too. Friday was my first day there and it was big 4 bedroom, 2.5 baths, swimming pool, and large deck over-looking Hollywood. Me being a closet crossdresser could`nt wait to dress-up. The first thing I did was to take a nice soothing bubble bath. I even shaved what hair I had off my legs and gave myself a “bikini cut”, that was something I’ve never done before and it made me feel real feminine. Seeing as I brought along my camcorder and camera I decided to dress like a regular Hollywood hooker. and take some personal photos of myself. I put on my black thigh high nylons, black thong, with a black teddy, short silver skirt, silver jacket, and 5inch heels. My makeup looked so good, I started to laugh, I’d pay me for me, I was fucking hot looking. I set my camera with 5 sec. time shots so I could do a little modeling outside and look at Hollywood at the same time. I was having a great time until I thought I heard another camera doing that whir, click noise they make. Before I could even look around I heard a car door slam then footsteps, I wasn’t sure what to do, I only knew I was too late. The back gate opened up and in came the pool man. He must have known he frightened me because He said loud and fast “It`s just the Pool man, I’ll be out of here in no time”. I was glad of that, but I’ve never been this close to another person while dressed like a woman. As exciting as this situation was I just nodded and walked into the house. I sat on the couch and had a small stroke; I did notice the pool guy kept looking at me through his sunglasses. And I don’t think most pool guys stroke their pool pole as sensually as he was doing. Well the strange thing that happened was that we just kept looking at each other and not caring whether we were staring. All the while I was wondering if I could give him a stiff one.
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