My first man

It started with me trying on my sister's clothes when I was home alone. I was about 16 the first time I got up enough nerve to take a pair of her panties out of the laundry basket and try them on. Just looking at myself in the full length mirror made my cock go hard as a rock. The next time I tried dressing I got one of my sister's  bras and stuffed it with some socks to make it look like I had tits. It took 2 years before actually got dressed all the way. I had a part time job at a grocery store which gave me money to spend on my own lingerie. I bought a wig, makeup and a lot of black lingerie. One weekend my sister had a soccer tournament out of town, my parents went with her leaving me at home by myself. When they left and I was sure that they were not coming back, I stripped down and began my transformation into Darlene. First of all I did my makeup, I had become quite experienced at applying my makeup. I put on a pair of black stay up stockings, I had a pair of crotchless panties and a nice black bra. I stepped into a pair of my mothers high heels and then topped it off with my long blonde wig. God did I look hot. Suddenly I was surprised by a knock on my door. I looked through the peephole and saw my next door neighbour standing on my front porch. I had always thought he was a handsome man so I decided to open the door and ask him in. He stepped through the door and pulled me to him and kissed me. He said that I looked beautiful. He said that he had seen me through the window and thought I looked beautiful. He asked me if we could go to my bedroom and play.  I took him by the hand and led him upstairs. He said that maybe he should shower and i told him no, I loved the smell of a sweaty crotch.  I layed down on the bed and told him to strip down and join me. He quickly took off his clothes and joined me on the bed. We layed there kissing and playing with each others cocks. We both became very hard, I suggested that we try a 69. We both layed on our sides and took each other's cocks in our mouths. He cock and balls were nusky smelling  which really turned me on. I took all of his cock deep inside my mouth. When he came his cum tasted so good. I swirled it around in my mouth savouring the taste and texture. We both swallowed each others cum. I came up and we started kissing each other again. He was my first man and I was going to make him my lover. When he got hard again he asked me if \i had ever been fucked, I told him he was my first man and I had never been fucked. I din't have any lubricant but I did have some vaseline. I went to the bathroom and got it and he lubed up my ass and his cock. He said it may hurt a bit. Was on my hands and knees when he started pushing his cock against my ass. It did hurt but I told him to keep pushing. When the head of his cock penetrated me I lt out a little whimper. He stopped pushing but I told him to keep pushing. He leaned in and pushed hiscockall the way in. It really hurt but he said it would start to feel good soon. He was right, it did start to feel fantastic. He started slamming his cok ind and out. He made me feel so feminis. When he came I could feel the warmth of his cum deep inside of me. . We ended the afternoon and I told him that I wanted him to become my steady lover. He was single so I started leaving stuff to dress up in at his place. My sister was heavily into soccer so every time my parents took my sister to a soccer tournament we got to play. We started taking photos and videos of each other having sex. I am in my 30's now and  I have moved away and have new partners but I will always remember him as my first lover.