I was nearing my thirtieth birthday and times were getting tough financially. I had gotten laid off from my job and was collecting unemployment and doing some part-time work helping out friends with odd jobs. One of them suggested that I look into cleaning houses. I've always been very neat and people often thought I was gay. I had dated many women, but never met anyone who might be Ms. Right. I must say that I sometimes fantasized about being taken by a man, but I never acted on it. I bought some dildos and practiced sucking on them and occasionally worked them into my ass. I thought that was as far as my fantasies would go. I had never really fantasized about cross dressing, though I did love seeing women in stockings and garters and other lingerie and I loved when they wore high heels. I never envisioned me wearing those things, but little did I know what lay in store for me.
I put an ad on Craigslist to offer my services. I would charge $75 or so, depending on the size of the house. There were a few calls, but we couldn't work out a price, then one day I got a call from a man asking me to stop by and give him a price. It turned out to be a very nice house. The man answered the door. He looked to be in his late thirties and in good shape. He was wearing a dress shirt, slacks and dress shoes. He asked me inside and I had a look around and he handed me a list of things he would want done; the list was what I expected: dusting, dishes, laundry, and general cleaning duties. I offered to do it for $80 once a week and we shook hands in agreement.
"So I'll see you on Tuesday at noon?" he said.
"Yes, sir," I replied. He smirked at my response.
I would go over each Tuesday. I figured it would take two to three hours to do and those few hundred bucks per month would really help me out. I bought cleaning supplies and started my new job.
The first few weeks went by without a problem. Once I learned to multi-task it only took me a little more than two hours. Rick, the homeowner, worked out of the house. Even though he was working at home, he always wore a dress shirt, slacks, and dress shoes. He apparently did some video conference calls from his study and wanted to look somewhat professional. We saw each other when I showed up and I usually didn't see him again until I was about to leave so he could pay me.
