Neighbor

One day I was in my patio and I saw my neighbor sitting in his patio. We greeted each other and I asked how he was doing. He wasn't very happy because his wife had left him a few months ago. I told him that I was sorry to hear of the news. Eventually, I came over to his house to talk more. He told me that his wife left all her stuff behind and just up and left with another man.

I felt bad for him, but I was curious about what she had left behind. I was always curious about dressing in women's clothes. I asked him what he was going to do with her clothes and he said that they were in trash bags next to the door leading into the garage. I looked over at the garage door and saw the bags. I told him I could get rid of them for him and he said that that would be great.

He asked if I wanted to go to the movies and I said sure. The movie started in two hours, so I went back to my apartment with the bags. I had a little under two hours, so I decided to try on some of the clothes. I slipped out of clothes and slipped into some nude pantyhose and an ivory skirt suit. I slid my hosed feet into the high heels. I found some of make-up in the bag and put some on. I've had some experience putting on make-up on my sister, so I was able to do a pretty good job on myself. My hair is naturally long so I just curled it a little. I walked around the house and felt very sexy.

Right then I heard someone knocking at the door and I was scared. It was my neighbor. He was early! I told him that I had to get dressed. He said "That's ok. I saw you through the window - I know". I opened the door, very nervous, and he stepped in. He looked at me and said "Wow, you look great - those clothes fit you really good". He asked if I would go out to the movies dressed up like that. I was nervous but I said ok. He first took me to get some dinner, and he kept looking at me and was saying that he was amazed how much I looked like a woman. He would stare at my legs, my butt, and all over. After a glass of wine, he became a little flirty and started to treat me more like a woman, taking me in his arm and walking me out of the restaurant. During the movie, he put his hand on my knee and gently rubbed my nylon leg. I was really excited. We went back home and he asked if he could come in. We shared a few drinks while we sat at the couch. He asked me how long I was dressing and I told him that this was really the first time. He then asked if I was ever with a man, and I told him no. He looked at me and then asked if I ever fantasized about being with a man while dressed up like a woman. I was a bit embarrassed, and I told him that sometimes I did. The conversation went on like this for around twenty more minutes. His eyes most of the time were down at my crossed legs, but strangely I was liking it and feeling excited by it.

He stood up and came over in front of me while I was still sitting. His crotch was in front of me and he just stood there stretching, and said thanked me for being his sexy date for the night. We both laughed a little. There was a bit of an awkward silence, and he was looking down at me. I was looking down at his shoes, and then I looked up at his crotch and noticed a big bulge. I looked up at him and he smiled. Still sitting on the couch, I leaned over and put my hand gently on the bulge and looked up at him again. He smiled and closed his eyes, and then opened them. I could feel his manhood pulsating under his slacks. I was nervous and excited all at once. I thought about how the hardness I was feeling under his slacks could end up sliding in and out of my pantyhose covered bum that was sitting on this couch - the pantyhose covered bum that he was staring at all night.

I unzipped his slacks and reached in. I felt his shaft and it was really hard and really hot with it being all gorged. It was slightly bent in the pants, and I pulled it out of the zipper hole of his slacks. It sprung out straight and I started to stroke it. He said his wife never got that close to his manhood with her mouth. I then put my lips around the head of it, and I could taste him. He put his hands on my head, and then to my surprise he slowly moved forward and slid his shaft into my mouth. We did this for a few minutes, and then leaned me back onto the couch and then lifted my legs over his shoulder. He could see under my skirt now and saw that I was getting hard under my pantyhose. He asked if he could be my first. My red lips were still wet from his leaked juices, and I slightly nodded, scared that it would hurt. He tore a hole into my pantyhose, pushed my legs apart, and I slid down the couch and was now fully on my back, ready to receive him. I felt the strength of his arms grabbing my ankles as he held them with my legs spread. I could feel the cool air blowing against my exposed hole. He rubbed the tip of his wet cock against the hole and then slowly slid it in and out. It hurt at first but then it was heaven. We both moaned as he took me as a woman. I was surprised how easily it slid in and out. He was pretty well endowed, so I could feel him stretching my hole and going deep inside me. Each time he slid his shaft deep into me, I felt the tip of my cock swell, as if each thrust of his cock was pumping incredible pleasure into mine.

We did this all night, and he thanked me for helping him through such a rough time in his life. From then on, we became the best of neighbors!