Written on September 15th, 2009
I've been caught a few times. But this one was at my grandma's house. My grandma knew of my crossdressing. She didn't mind it. She didn't really understand it either. But, if I wasn't out drinking or doing drugs then it was ok with her. As I was saying I was at my grandma's for the weekend. I was around 19 yrs old. My grandma was out with her friends for the day. So I decided to dress up. As I brought some stuff with me from home. And my grandma would get some stuff from time to time. Or she would give some of her old stuff she didn't wear anymore. Let me tell you what my grandma was no elderly looking woman. She always tried to stay with the times fashion wise. Hair, clothes, shoes, ect. You know what mean. And yes like most grandma's she love to wear pantyhose just like my aunt. Thats another story. Well since I had the house to my self I decided to change into something more comfortable. I went into my room which was the guest room and got undressed. I put on some biege pantyhose, a bra. Went and walked into my grandma's room and put on her jean skirt that was above the knee. A jean button up top as well. I brought some black 3 1/2 inch open toed high heels. I slip them on did my make up and put a wig on that was auburn colored. I went into my grandma's room to take a look at myself in the mirror to see how I looked. I thought I looked pretty darn sexy if you asked me. As I come walking out of my grandma's room. There was a guy standing in the living room. It was one of my grandma's friends who came over to drop something off. He turned around and he looked right at me. We both were like holy ****. Not out loud but expressions that day were louder than words. He dropped off my grandma's mail and he turned around and left. As he closed the door I hurried over to the door to lock it. I was a bet freaked but I have been caught before. But, not by one of my grandma's friends. After a bit I decided to change. After I changed I was watching tv wondering about my grandma's friend. Let me clear some thing up. I did know him while I was growing up. He is a real nice guy and a good friend to the family. So, for him to catch me dressed up had me feeling awkward and weird and scared. Anyway as I was sitting there the sliding door to the back yard came open with a knock at the same time. It was him. He asked if he could come in. I said sure. As he came in I got real flush and embarressed. He sat down and asked where my grandma was at I said she was out with some friends. He asked do you know when she will be back I said no I don't. He asked why were you dressed like that. I looked at him paused for a bit. He said well I told him that I like to wear womens clothing. As I like how they make me feel. He asked if my grandma knew I said yeah she knows. He said anybody else. I told him yeah a few people. He asked so you like to dress like that then. I told him yeah I do. He said would you dress like that for me. I looked at him and said if you would like. Thinking god your kind of a creepy old fart. I asked would you like me to now. He smiled and said yes if you would want to. So I nodded and got up and went into my room grabbed my stuff and went into my grandma's room. I opened the door a little while later. Wearing some off black pantyhose, a black skirt, white blouse. A black coat that went with the skirt. A pair of black 4inch pumps I got from my girlfriend. Wearing the same wig. And had my makeup on. I walked out into the living room where he was sitting. I stood in front of him and asked if he liked what he saw. He said yes. I walked over to the couch and sat down. Crossed my legs. Hearing the swish sound from my pantyhosed legs. He kept looking at me and my legs. He got up and sat down next to me. He put his hand on my leg and was rubbing it. That felt so good and then he leaned into me and kissed me on the lips. Even though he was older it felt so good. As he was so gentle and not rough. As we were kissing for a bit on the couch. He started to slide his hand up my hosed leg. Getting closer to my crotch. I was as hard as a rock. He stopped just short of touching my ****. And kept his hand there as we were kissing. I started to glide my hand around his crotch area squeezing his ****. Feeling it get hard. I started to undo his pants and he helped a bit. I started kissing his neck and then went down on him giving him head. Hearing him breath heavy and hard and telling me how good it feels. I could start to taste his pre ***. I felt his hand on my head having me go a little faster. Then blam he came. And boy did he *** alot. I tried to swallow what I could as I liked how *** tasted and it seemed to turn him on. After I was done he just sat there for a bit. I got up and went into the bath room to wipe off any *** that I didn't swallow. After which I went back out into the living room. Where he was sitting. I sat back down next to him. He looked at me with I can't believe that happened look. But, it was a good look. He said I probally better go before your grandma gets home. I agreed. As I didn't want her to catch us doing anything else. I walked him to the screen door and he kissed me one more time and said see you sweety. And left out the back way to his house. I stood there feeling slutty a bit. Which felt realy good actually. I decided I better change before my grandma gets home. So I ended my night with a jack off session in my slutty secretary outfit. Changed before grandma got home and just hoping for another visit from my old friend.
