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He felt disconcertedto find out a woman from the local amateur dramatic society was going todo the fitting. She had volunteered to do it so she could begin hiscoaching for the role. It surprised even more to find out she was prettyand only about five or six years older than himself.She introduced herself as Shirley and asked if he had ever played agirl's role before. When he said he hadn't, she cheerfully said that itwouldn't be a problem, with his figure she thought he would do fine.Shirley suggested he should try on the dress first as it would be easierfor him to get used to the role in costume. She had him strip to hisunderpants, and his face burned to be like that in front of her, but shedidn't seem to notice. He remembered the totally unexpected thrill whichflooded through him as she dropped the dress over his head and laced himtightly into it. Shirley made him wear some white tights under the dressand he shivered as he felt his nylon clad legs rubbing against eachother.She sat. Next thing I know he had me on my back and was sucking my dick which felt really good as I held on to the back of his head. I was playing with his cock while he was sucking mine and I asked him for the first time if he wanted to fuck me to which he smiled and said "yes I do"! I opened my legs for him and he grabbed some lube and put it on my ass and his cock. He moved into position (me on my back still) and teased the perimeter of my hole for a few seconds. I couldn't wait for him to penetrate me so I grabbed his ass and pulled him toward me. I could feel the head of his cock start to open me and I felt the initial pain. I relaxed my hole and pushed out a little and my ass loosened some as he pushed in further. The pain subsided quickly and he began to thrust. He found my prostate quickly and was massaging it with his thrusting cock which made me begin to moan and squirm. It felt so good getting my ass powerfully pounded by a man. I grabbed his ass and squeezed as I pulled him into.
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