My Summer As A Girl

by Anonymous

It was the beginning of summer and already I was feeling bored. That was usual and to be expected, of course.

My mom had already left for work and I was trying to think of something to do. Nothing much was coming to mind, though. I had just gotten up and had pulled on a t-shirt and jeans and was still barefoot. I was always a little shy and self-conscious about going barefoot, like a lot of boys, and I wasn’t into wearing sandals –although I did have a pair of flip-flops, even if I never wore them outside, but I liked being barefoot around the house.

I spotted a bottle of my mom’s nail polish sitting there. It was a shade of deep reddish-brown. I looked at the bottle, and I don’t know why exactly, but I was suddenly curious about what it would be like to have painted toenails. So I took the bottle, opened it, and dabbed some on my right big toe. I studied what I saw, and encouraged, I went ahead and began to dab paint on all of my toenails. In a minute more, there I was … with painted toenails. I smiled. It looked kind of wild and neat, I thought. I had to admit that it was sort of a turn on doing that as a boy.

I spent the rest of that day walking around the house enjoying my frivolous indulgence. Then, at four o’clock, and knowing that my mom would be home half after five, I went and took some polish remove and cleaned off my toes. It had been fun, but of course there was no way that I could let my mom know that I had done something like this. Girls, in that way, it seemed, got to have all the fun. For boys it just wasn’t allowed. I looked down at my now plain toes and felt just a bit disappointed.

The next morning, after my mom left for work, I went and painted my toes again. It was great and so much fun. I looked down at my deep reddish-brown nails and thought how sexy that looked, and I felt myself starting to get an erection. That felt good and I didn’t mind that at all. I was in the kitchen sitting at the table. Happily I unzipped my jeans and bared my now quite stiff penis, and bean to stroke it. That felt really good, and exciting as I looked down at my painted toes.

Very quickly I brought my erection to a climax and directed my liquid release down on my bare feet and my painted toes. With the slick floor in the kitchen I didn’t have to worry about where my discharge went. It was good doing that and so thrilling to wet my feet like that and see my white liquid dribbling over my painted toes. I went and got a paper towel and cleaned up my mess. Then, after lunch, still enjoying the thrill of my painted toenails, I jacked off onto my feet again, and shot a large wet load for a second time. Of course, later, and before my mom got home, I removed the polish again, making sure not to leave a trace.

The following morning I indulged my playful fun again and painted my toenails. Enjoying this, somehow I began to wonder just what I would look like ass a girl. I went into the bathroom. My hair was somewhat longish, and I combed it out into kind of a girl style, found some of my mom’s eye stuff and some lipstick, which I carefully applied. Then, looking into the mirror, I was surprised to see this rather cute looking girl gazing back at me. I laughed. This was so neat! I spent the rest of that day going around the house in my girl guise having a blast, and I masturbated thoroughly – twice. It was such a complete turn on pretending to be a girl.

Over the next week I did this every day while my mom was at work and it so terrific. Then the weekend came and my mom was at home, and I couldn’t be so indulgent. I really missed the freedom of doing this girl-guise bit.

When Monday morning came, I was right back at it. I was perfecting my girl-look and now becoming use to getting into the proper mode. It was kind of funny because I started to realize how little difference there was between boys and girls, how much they actually did look alike. Not that I wanted to be a girl. I was perfectly happy being a boy and having a penis and erections. Still, I was fascinated by being able to transform like this just for fun. I started to wonder if I could actually get away posing as being a girl out in public. Bravely I decided to try.

I really didn’t have any girl clothes, but that was not much of a problem. Most girls dressed just like the boys did. So I put on a purple t-shirt – which seemed the most girlish-thing I had, wore my faded jeans, and slipped on my pair of flip flops. Then, summoning my courage, I stepped out the door. It was a little breathtaking. There I was outside, as a girl. I drew in a deep breath and went walking down the sidewalk. There was no one around to see me, so that wasn’t too difficult. It was such a blast pretending to be a girl like this.

Only I saw someone walking toward me. My heart thumped. It was an older couple. Instead of turning around, I tensed and forced myself to walk straight past them. They took no notice of me at all. There were no strange looks or anything like that. And they had clearly seen me. But to them – I was a girl. I was elated!

I spent all of that week venturing out in my girl guise, walking around the neighborhood, hoping that I wouldn’t run into anyone who knew me. I was not at all sure if I could pull that off. While I was out walking I felt so incredible sexy and this gave me a fantastic erection, which was stiff and upright in my jeans. I wandered down to the small park that was nearby and no one paid any attention to me. I was passing for being a girl without question. I remember wondering what they would think if they knew that this girl was having such a hard erection. I was so turned on that just when I was getting back home, I found myself actually ejaculating in my jeans. What a mess! What unbelievably fun!

It was a week after that I became quite seized with a sense of adventure, and I decided to get on the bus and go downtown as a girl. I got on the bus, paid my fare and went back and found a seat. No one gave me a second look. I sat there and rode along enjoying my disguise. In town I got off and walked along the sidewalks, realizing that here I was – being a perfectly ordinary girl. It was a strange feeling of duality, I can tell you, but that I thoroughly enjoyed experiencing.

For the rest of that week I went downtown every morning as a girl, and went back home in the afternoon and changed back to being a boy. When my mom cane home she had no idea of course, and was just pleased that I seemed happy enough and not too bored.

On one of my trips downtown I passed by several boys my age, and they all turned and gave me a look. I was seized with fear. Did they think that I was a boy and just doing something that was totally faggy? Apparently not. One of them called and said something about me being “good looking.” I was a total success! Man, did that every give me an erection after that!

The only problem was, as I discovered, that while it felt so great to have fooled those boys, and to receive a compliment, just how did I feel about boys finding me attractive? In my girl guise that was terrific. But as a boy … that was a little weird, especially getting an erection from it. I really had no desire to be gay with another boy. Uggg! I decided that I liked the girl part, but that underneath it all, I was still very much a boy.

I spent the rest of that summer being happily indulgent, and it was funny, because I really had not realized it before – but here I was being a cross dresser. I had heard about that, of course. But somehow I had always imagined it to be something weird. And now, to me, it wasn’t weird at all, just fun.

The summer came to an end and fall arrived and school was starting.

Oh, so sadly I was forced to give up my role playing and girl guise, and I dreaded the long moths ahead. Although, I was really looking forward to that next summer.