There was this older couple that lived in the same high rise apt building that I rented a studio apt at. I had learned that the man's wife had left him. I was at the elevator one night that we both were waiting for and we said hello to each other....I had never met him before but I had seen him. He asked me what a young man like me was doing home so early on a Friday night. I told him I had nothing to do except watch some TV. I knew I was bating him. He then asked me if it wasn't much trouble could I help him move a piece of furniture. It was just to heavy and awkward to move by himself. I told him sure, no problem. He was about 6' thin and lean as I was following him down the hall. He introduced himself as George and again thanked me for helping him out. Once inside he showed me his armois (sp?) and it was big and heavy. We moved it over to the opposite corner and after that my muscles were definitely spent from moving that thing.
He asked me if I wanted a lemonade or something and I agreed. While in the kitchen I asked him where his wife was. He told me the truth, that she left him. He said they grew apart after 25 years of marriage and that he missed her but did it allowed him to explore things about himself. So I took the bait and asked him "like what?" He said that I might be freaked out if he told me and I said nothing freaks me out....too much anyway. George started telling me he liked to dress up in womens clothes. This instantly excited me cuz I had fantasies about it and I tended to lean on the feminine side of my sexual encounters.
I said, "wow, really, I'd like to see that some time" His eyes got big and he told me he'd dress me if I liked. Back in his bedroom he opened his closet and he had everything in there...dresses, wigs, you name it. My cock got throbbing hard as he was showing me. It then occurred to me that maybe he wasn't gay which all along I was assuming he was. I started feeling funny about my hard on now. George pulled out a cocktail dress, a blonde wig, and a pair of high heels and asked me to try these on as he pointed to the bathroom. What the heck, right? I closed the door and started undressing. When I had everything off he knocked on the door and slightly opened it and with only his arm he waved tiny pink panties and said don't forget these. I could barely get the panties on because they were thong in the back and hardly anything in fron and my cock was at full attention but I managed my cock downward and kind of trapped my cock in. I slipped the dress and wig on, put the hells on and looked at myself in the mirror.
I was very horny now and very excited to be doing this. George talked through the door and asked me how I was doing. I told him I wasn't sure I could walk in these things. So he came in with a bathrobe on and looked at me and said how good I looked. To tell you the truth I never felt sexier. He then bent over and touched my legs and told me what cute slender legs I had. He said if I shaved my legs and put a little make up on I would look really hot. I then lifted my dress to show him the panties as he could see my cock ready to pop out. I said how do you keep your dick in with these things!
He took his robe off and all he had on was a pair of panties as well and a hard on! He said it is quite a balancing act isn't it? As I still had my dress hiked up he took off my panties, looked at my cock and said next time he'll try to find ones more sturdy. He walked me to the bed and buried his head under my dress and started sucking my balls, taint, and then straight up my cock. I was lying on my back with my legs up and I was looking at these cute shoes on my feet. Then we acted out our sex as if he was a man making love to a woman. WOW! that was fun.
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