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So, about my experience with my female side-Part 1  

DreamyCD4U 49T
9 posts
9/30/2020 5:28 pm
So, about my experience with my female side-Part 1

No, I am not on that fashionable train that so many have decided to ride, I never bought a ticket. My experience with having a whole part of myself that is female began when I was 5 years old, back when the word crossdresser was not even a term. I never had any idea that it was a thing.

Some background:

Having been born after the end of the Baby Boomer generation, I am considered a Generation X member. Looking at GenX, one of the oft stated characteristics is that many of the spent an undue amount of time at home alone, since in many cases both parents worked and were not home when the went to school and came home from school. Not to mention being at home alone when parents were at some sort of organization meeting, etc... Regardless of how that affected GenX social skills and how it served to develop personality traits ( I mean, it is what it is, or was more correctly) I was in that situation. Both parents worked, grandparents would loosely watch me when I got home, at least till I was in second grade, and I had a lot of time alone. It isn't all bad, in fact there was a lot of good in it. Developing a good sense of independent play, a healthy creative imagination and ending up with a strong sense of direction were just some of the positive side benefits. One other benefit was the development of very strong observational powers, which were critical in noticing things about women, such as the way they dress, mannerisms and other such things. But, there was a lot of unsupervised time, especially in lieu of being an only , which multiplied the solo thing. How did it all start?

The Story:

I was always curious about what it was like being a female. Women always had nice clothing, they had something different than males...no, I meant overall. People looked at them differently. They were pretty. At the age of 5, I would sneak into my mother's closet and try on her things, when no one was in the house. Grandparents, upstairs or outside in the garden. My mother was a petite woman and most of her clothes were within reasonable sizes. I tried on her shoes, put on stockings and dresses, never leaving the closet. Yes, ironic isn't it. This went on through grade school in ups and downs, sometimes more, sometimes less, all depended on my schedule and my parents. It was a very strange feeling when I was dressed as a female, something felt right and also very strange, like a tingling sensation. I don't know, I was too young to analyze it and now I am not sure my memory is accurate with those feelings,.. maybe, but why dwell on it. This went on for some years, all the while I enjoyed the life of a normal athletic young boy, who liked to play sports, play army in the woods, fished, built models and all those other things that young males do in our society. The normal back and forth of parents versus went on in our household, however my mother could be very tyrannical at times. Nothing super unusual I am sure. Sometimes, when I would perform poorly at practice or a game, or failed to stand up to a bully, she would say that they were going to buy me a tutu. Of course, I always objected, but I did inwardly think that wasn't so bad. I would have liked to have a ballet dress, for private of course. What she meant was to ridicule me into being more masculine.

When I was in 6th grade, we moved to the next town over and our house was on the outskirts of town and on a big hill. Needless to say, there weren't any neighbors and once again my parents both worked and now, there were no grandparents to hang around. In 7th grade, my parents were busy one night at a meeting that would see them away for at least several hours. There is only so much homework a can do before there is nothing else. No cable at that time, no computers or anything like that. Yes, I read a lot. While I had been still doing the mom's clothes thing, I was really alone now and finally went all out. It was the first time I actually dressed completely and did makeup. I should say right now, that I had medium length wavy blond hair and was sometimes mistaken for a boyish girl, usually when in winter clothing. Sometimes, not always, actually a few times. Anyway, this was the very first time I dressed fully as I said before and it was a watershed moment for me. At this time, I was about 5' 1", within a inch of my mothers height, slim and fit.

As I was looking through my mom's stuff, I found a pair of white satin nightgown pants, with elastic around the ankles that made them look bloused. I suppose they could've been polyester, but I don't think so, but I digress. I put those on with no panties and yes, they felt wonderful. I then found a pair of multicolored pair of very brief panties which I put on over the top of the nightgown pants. When I looked in the mirror I got an idea, it was from something I had seen either on TV, book or magazine. I continued looking and put on a very sexy bra or<b> bikini </font></b>top, I can not remember, as much as I try. I added to that a somewhat see through short blouse that only came down to the small of my back and only had a button at the top. Finding a nice ring belt, you know, the ones that were popular in the 60s and 70s, I put it around my waist, so that it was just under my belly button. I messed around with some eye shadow, making what I thought were Egyptian type wings at the outside of the eyes, added some lipstick and then put on as many bracelets I could on. I put some of the bracelets on my ankles and another one of the ring type belts around my head, like a headband and a few necklaces around my neck. All the while I had been doing this, I hadn't really looked in the mirror at the whole picture. I had been doing the makeup and lipstick, but didn't step back and look full length until I had completely finished. When I did step back and viewed what I looked like, I was startled, surprised and completely pleased all at the same time. Now, I am biased at how I looked, but when I say that I was looking at a young, very female belly dancer, I am not exaggerating. It was such a moment that I will never forget it. All at once, I knew that my previous feminine feelings were not just a strange little phase or fetish (not sure I knew the word fetish at the time). It was everything I had wanted and everything that I had thought it would be.



Right then and there, I danced in front of the mirror and as I did, I began to feel very strange. It was extremely sexually arousing. I continued to move in motions that were what I had seen on TV and other places, trying to mimic a belly dancer. It went on like this for a while and I stopped for a moment to look at myself again. There was a little spot that was beginning to appear in my panties, which I was unfamiliar with. I paid no attention to it and once again danced. After a little while, I went over to the bed and copied the poses I had seen women in magazines. It was so erotic, I can not begin to explain just how much. I got back up and danced in the mirror again, everything felt so good and not just in the mind. My body was reacting to the change and as I moved, I began to feel something I never had felt before. I stopped and looked at myself and the spot had become bigger, not knowing what was going on, I pulled the panties and night pants down, while looking at the mirror and noticed that I was very, very hard. I barely even touched myself and without warning, I had my first, biggest and best orgasm I have ever experienced to this day. It came out all over the top of the dresser (thank goodness for that, it was easy to clean up), all over my hands and a little bit splashed off my arm and hit my lips. I was able to taste it and it didn't taste bad either. I just stood there, completely dumbfounded. I knew what happened, I wasn't stupid, but it was a feeling I had never had before. After a minute or so, I backed up and laid down on the bed on my back, just contemplating what had happened. I did run my arm along my lips, tasting more and eventually swallowing what little I did get in my mouth.

Looking at the clock, I had to clean up and get things back to where they belong. It was hard to do, since my head was buzzing and moments before, I had experienced what I will always look back on as a seminal moment in my life. I had to clean the panties and nightie pants with a paper towel and was very worried that my mother would notice, but she never did. I haven't really analyzed the episode too much, I think it kind of takes the fun out of it, or not. Either way, it is a story that I hope you find interesting. It wasn't the beginning, I was interested in being a female long before I was sexually mature and way before I even knew what sex was, but it wasn't the end either, it was perhaps the end of the beginning.

Here is a question, who did I just paraphrase in those last two sentences? Anyway, part 2 will be coming soon, I hope.

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