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All my life I have been an occasional but committed cross dresser. Iloved my dresses and skirts but above all I loved my humble cleaner'suniform and I already was dressed in it. Nothing fancy, just a plainhousekeeping dress of the type that hotel maids have to wear, a workingapron, pantyhose and comfortable shoes. And of course, the appropriateunderwear, matching panties and bra and my very realistic breast forms,the only expensive item of my cheap outfit.I fixed my thick longish hair into a more feminine manner, I put somelippy on and I was ready.I had no illusions of course as I looked at myself in the mirror. I knewthat I had an androgynous look and I couldn't easily pass in public as afemale but that didn't stop me doing it. The inner satisfaction I felt,sexual and not only, was the strongest possible drive, a drive I couldn'tresist though I have tried to stop it on numerous occasions over theyears. The urge was far too strong.But this Saturday was going to be double special. My cock and balls felt crushed against his desk as I moved my hands to my ass, slowly spreading and giving myself to my new man. He placed a finger against me, teasing the outer ring before beginning to slowly push its way in. I gasped and felt my ass clench on his finger."So tight," he sighed and pushed his finger the rest of the way in. He waited a moment for me to adjust and then began to slowly finger fuck me. By the fourth or fifth stroke, I was pushing my ass back to meet him. He added a second finger, then a third, stretching my ass, preparing my pussy to accept him. Suddenly, he pulled out, leaving me with a feeling of emptiness and a desire to be filled.I tensed as he stood behind me. I felt his cock rubbing along my groove. He leaned over and whispered, "Just relax, you're going to love this." I tried to relax as he lined up with my hole, but the initial pain of penetration caused me to clench on his head. He held still, caressing my back, allowing me to become accustomed.
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