When I was on vacation in Green Bay Wisconsin, I was reading the local paper. Having nothing planned for that day, I decided to go to a yard sale that was listed in the paper. I figured maybe I could catch a bargain on some older items made in America. I looked up how to get there and it was on an isolated farm, a good distance away from other homes. By the time I arrived, there was no one else there and it had been picked thru. The owner, an older sixtyish man was quite pleasant and said “take a look.” As I looked, the man told me he was going to start putting things away. As I looked, I kinda helped him move some things to the barn. Not that he needed help this older man was built like a tractor. We made some small talk as we continued. A few remaining thigs needed to go in his house. I helped bring them in his house. After we finished, he offered me a beer for my help.

As we had a beer, we talked. He told me that his wife had passed away. He gave me another beer and we continued to talk. I noticed some boxes and asked if he had more items. He told me, no they held some of his wife’s clothes and he was going to donate them. Since I was somewhere that nobody knew me, I took a chance and asked him if he wanted to sell some of them. He looked at me kinda funny and I opened up to him that I had thoughts of dressing like a woman and this was a chance to see if I liked it. He just shrugged, and muttered it takes all kinds I guess. My face was red and I told him I understand that he did not want me to. He said, no he was open to it. Follow me as he led me to the bedroom. The closet on the right has some of her better clothes in it. “You can try some on while I clean up.” I thanked him and he went into the bathroom.

I opened the closet and saw a blue dress that I wanted to try first. I stripped and put on the dress. I was very excited as I looked in the mirror. Wow, this is what crossdressing feels like. His voice woke me from my euphoria. He told me the top drawer in the tall dresser has her undies in it. I raced to the dresser and upon opening the drawer, was met with a variety of undies and my excitement increased. I took off the dress, rehung it and went back to the drawer, not only did it contain some sexy panties, some plain ones too, it held some very sexy negligees. I had to try on this one black teddy (I found out what it was later). I slipped it on and slowly walked over to the mirror. My gosh, this is unreal. It made my chubby body look good. I was stunned, yes I am gonna do this more often. I had to buy some of these from this man. I was brought back to reality as I could see the farmer move behind me in the mirror.

“Not bad”, he said. “From the back you could be mistaken for a woman.” I needed to hear those words, but before I could turn to answer him, he grabbed my shoulders and pulled me back into him. I felt his cock as he pressed against my ass. I was not expecting this. He draped his arms over my shoulders and gave my nipples a good kneading as he kissed my neck and told me he had not had sex since his wife passed. He licked my ear and whispered in it that I was going to make him happy tonight. All the while I could feel his cock hardening against my ass. I tried to tell him that I did not do it with men. He pushed me onto the bed and quickly straddled me rubbing his cock in the crack of my butt. His hands were mauling my hard nipples as he leaned forward letting me feel just how big his cock was. “Please stop” I pleaded. “Too late, you turned me on, now I am going to fuck you.”

“Nooooooo. Please don’t.” He laughed as he continued mauling my nipples. And his cock continued to separate my cheeks. I moaned as he kept working over my nipples. “See,” he said, “you are enjoying this. I am going to give you much more to enjoy.”

He removed one hand from my nipples as he reached to the night table. I took a chance and tried to wriggle free. It was then I found out how much stronger he was than me. He told me “if you do that again, I will restrain you and use you anyway.” I kept struggling and pleading for him to let me go. “Okay”, he said. I started to get up, but he grabbed me and led me to the closet. He grabbed something and it turned out to be ties. He then pushed me back onto the bed and proceeded to tie my hands to the headboard. I cried, “noooooo, please noooo.” But my cries were ignored. He opened the drawer on the night table and took out a big jar of vaseline. He told me “you are going to need this, so relax and let it happen.” He slid a finger coated with the vaseline into my ass. Damn if this was only a finger, I am in trouble. Slowly he worked his finger in and out, telling me what a nice fat ass I had. He had me moaning in a few minutes, when he withdrew his finger. Next I felt two fingers enter my ass. Damn this hurt and did not feel good at all. But he continued, ignoring my begging for him to stop. After a few minutes, he had opened me up some more and the pain had stopped, giving way to pleasure and me moaning a lot. I was close to cumming and he never stroked my cock.