Men Wearing Panties, Pantyhose, And Lingerie
Submitted Stories
Title: Lawn Boy
In the summer of 1983 I was 18 years old and never had sex before. But I always liked to dress in womens clothes since the age of about 13 or so. Anyway, I always cut the grass of this older couple who were in there 60's at the time. So this one particular Sunday afternoon I was cutting the grass and this was the first time since his wife had passed away. After I was done, I went to his door to let him know I was finished and he said that he knew I wore womens lingerie because he would often see me thru my bedroom window. I tried to deny it but he had me dead to rights. Describing everything he saw. He asked if I would be willing to dress for him because it had been along time since he had seen anyone in sexy lingerie. So I obliged as long as he didn't tell anyone. He agreed. So I went home and grabbed most of my girlie things and went back to his house. Once inside I went into the bedroom to change. I put on a purple and black teddy with matching purple and black satin panties, thigh highs and a blonde wig and black pumps. I did my makeup and went into the living room where he was sitting on the couch. He just stared at me and told me to turn around so he could see it all and said that I loked beautiful. I could see that he was getting hard and I wasn't sure what to do since I was still a virgin. And he could sense that I was nervous and motioned for me to sit next to him. Which I did. He unzipped his pants and started to rub my legs and then he turned to me and started kissing me. As he was kissing me he pulled out his cock and put my hand on it and I started to stroke it up and down. He asked if I had ever been with a guy before and I said no and that I hadn't been with a girl either. He then asked if I would give him a blowjob, that was one thing his wife never did. I said I would but I didn't know how good it would be. He said to take my time and just do what comes naturally. So I proceeded to wrap my lips around the shaft of his cock and started to suck, moving my mouth up and down his cock, I could tell by his moaning that I was doing something right. I continued to suck on his cock, licking the shaft, licking his balls, getting better and better as I went along. Trying to do what I had seen the porn stars do. After about 20 minutes of this he said he wanted to make love to me and we went upsatirs to the bedroom. Where he laid me on the bed, told me to put my legs up over his shoulders, he slid my panties to one side and told me to relax. With that I felt him put some kind of ky jelly on my ass and then felt the head of his cock pushing it's way into my virgin ass. After he was all the way in, he just sat there for a minute to let me have time to get used to the feeling. It didn't take long for that to happen. It was the most exciting, intense feeling I ever had. He started to slowly slide his cock in and out of my ass, picking up the pace. The faster he got the louder I was moaning in pure pleasure. This went on for about 30 minutes until I felt the warm rush of cum filling my ass. He pulled out and lay next to me and said thank you and that I was great and asked if we could do it again at another time. I said you bet. Later that night, I told my parents I was going over to check on him to just keep him company and I got dressed in my prettiest pink satin panties and bra, thigh highs and garter, wig and so forth. And we had more great sex that night ending with me swallowing every drop of his cum. I am since married to a wonderful woman but still dress and still attracted to older men and try to please them as often as possible.
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