When I was in high school I wasn't very popular. In fact, I was quite a loner. I had a few friends from the place I worked after school, but I usually chose to be alone when I wasn't working or in school. My escape from the loneliness of high school was to dress up like a woman in the few clothes I was able to buy with the money I saved up from working.
Sometimes, I liked to wear panties and pantyhose under my clothes when I went to school. One time my parents left for two weeks to go on a trip to Europe. So I had the whole house to myself. I decided to dress underneath my regular clothes in panties and pantyhose and go to school. Everything was great until an older class boy was sitting behind me in my math class, Jim, leaned over and asked me in a whisper if I was wearing pantyhose. I was nervous, but finally said "yes". He just said "nice" and didn't say anything else after that. I was scared that he would tell the other boys, since he was a jock and quite popular.
When I went home I put myself together, even putting some subtle curls in my naturally long hair. But when I came out of the bathroom, the doorbell rung. It was Jim. He said that he was curious about why I dressed up and just wanted to talk. I let him in and told him that I'll get dressed. He asked me to dress up for him because he always wondered why some boys dressed as girls.
I got dressed, put on my makeup, and made my naturally long hair. I came down and he looked at me and was really surprised. He said "Wow, you look like a girl". I just smiled. He asked me to walk around in front of him to see if I walked like a girl. He kept looking at my legs and my butt, and asked if I was wearing pantyhose. I told him I was.
I turned on the TV and he said to turn it to the sports channel. He said he wanted to watch the game, but that it would be fun if I pretended I was his girlfriend. He asked me to get him a drink and I did. We were having a lot of fun. I got up to pick up the empty glasses. Not really being aware, I bent over slightly in front of him to pick up the glasses and I heard him say "woah". I asked him what was wrong, and he told me that my skirt hiked up a little when I bent over, and stretched over my ass. He said I had a really nice butt and laughed. I was then surprised to notice that there was a growing bulge under his workout shorts. When I went to the kitchen and put the glasses in the sink, I was surprised to find him behind me.
He asked if I liked dressing like a woman and I said I did. Then he asked if I would ever like to feel like a girl. I didn't know what he meant, so I asked him what he means by feeling like a girl. He came over to me and then started to show what he meant. He kissed me and moved his hands all over my ass, and then under the skirt. He bent me over the counter and continued to kiss me from behind. I bent over some more and he knew that I understood his question, and that the answer was yes. He put his hand under my skirt and rubbed my crotch through the cotton gusset of my pantyhose. "You really look like a girl, and I bet you really feel like one too". He rubbed against me with his crotch and I could feel that he was really hard. "Are you sure you don't have a pussy under here?" he asked. I told him that I have something he could slide his manhood into, but that it's probably really tight since it's never been penetrated before. He tore a hole in my hose and I bent over even more so that I can really receive him. He positioned himself and pressed the head of his throbbing manhood against my hole. He said "Wow, it's really wet" and I told him that I put some lube there while I was getting dressed. The head popped into me and he slid in and out slow. I felt like a girl, and I really liked the way it felt. I felt so femininely vulnerable in the position I was in. It first hurt when he first put it in but it felt really good after that. I could feel him pumping in and out, deep inside my tight hole. He told me it felt better than a real pussy, and smelt better too.
The next two weeks, he came over every day after school and I tried on outfits for him. He continued to make me feel like a real girl, the way he would handle me. It was one of the best two weeks of my life.
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