I came back east last September to attend college in Philadelphia. To save money I moved in with my uncle Jim. He lives in a beautiful home in Chestnut Hill. He lives alone since my aunt passed away and his kids are grown and on their own. I have the use of an old Volvo and the run of the place. We play golf and squash regularly at his club. He has a woman come in to clean and cook so it's a pretty good set up. Over the last couple of months our relationship has taken a rather interesting twist.

One evening after dinner we were putting a major dent into a really good bottle of scotch when to my utter surprise he produced a joint, lit it up and passed it over to me. The pot was very potent and I got extremely high. the conversation eventually turned to sex. At one point he remarked how much I resembled my Mother's side of the family. He became a bit sad when he began talking how much he missed his wife Barb, my mother's sister. He remarked how much I looked like her and invited me upstairs to show me some pictures of her. The pictures were quite shocking. There were dozens of shots of her in various stages of undress and several more of her engaging in various sex acts with men other than my uncle. There were shots of her with two guys and even a few of her in a gang bang with several men. As stoned and stunned as I was I had a massive hard on. After looking at the pictures he led me into her walk-in closet. The assortment of clothes, shoes, wigs and lingerie was incredible. He said he could never bring himself to part with her things. I was feeling sorry for him and as shocked as I was when he asked me to try on some of her things, I agreed.

He told me to take my time and make myself as pretty as I could. I had dabbled a little in crossdressing having tried on some of my mother's things and the idea of getting all dressed up was exciting. I have a slight build and fit into her things easily. I put on a black lace matching bra and panties. I stuffed the bra with some panties and put on a pair of sheer thigh-high stockings. I did my best with the makeup and tried on a couple wigs and went with a shoulder length brunette one and a tight black dress. Her shoes were a little tight but I found a pair of open-toed pumps and squeezed into them. I was a little disappointed when I looked in the full length mirror. the outfit looked pretty good but I hadn't done a very good job with the makeup.

When I started down the stairs he appeared at the bottom of the staircase and gave me a big smile. Taking me by the hand he led me into the living room and he became a little rough, forcing to my knees as he dropped his pants and forced his hard cock into my mouth. I was caught off guard and began to gag as he forced himself into my throat. He was holding my head tightly and began to skull fuck me. I was having a difficult time breathing and though I might pass out when he withdrew and pushed me over the end of the couch. He roughly pulled up the dress over my ass and pulled the panties to the side and then savagely penetrated my asshole with his big cock. It hurt like hell and I resisted but he got the better of me. I accepted that he was r****g me, relaxed a bit and he eventually buried his cock in my burning ass. After he came in me he began to whimper softly and apologized for what he had done to me. He slowly withdrew from my ass and gently helped me to my feet. My ass and jaw hurt and my head was spinning. He continued to apologize and helped me upstairs and helped me undress and get into the shower. I was in there a long time.

I slept in late the next morning and it was early afternoon by the time I made it downstairs. I wasn't sure how I was going to face my uncle. As soon as I walked into the kitchen he stood up and walked over to me. He apologized again and said he felt terrible for what he had done. I forgave him and he seemed quite relieved. We were out of milk so he asked me to run to the store. I was looking for my car keys and couldn't find them. When I asked him if he had seen them he said that he had gotten rid of the car I was using. He tossed me what I thought were his keys and I was thrilled when I walked outside to find a brand new BMW convertible! I decided then to work hard on improving my makeup skills.