THE JOYS OF BEING A CROSSDRESSER
I have been crossdressing almost all of my life. It all started one day innocently enough by my being curious about what a female would wear, how it would feel and how I would look. I had come home from school a little early and discovered that my mom wasn't home, she had gone shopping with her sister, my aunt. I then went into my moms bedroom and went straight for her large dresser. I opened the top right hand draw and found stockings, all neatly folded. I took out the very last pair and just held them in my hand and felt that wonderful wispy feel that only a full fashioned nylon stocking can feel like. I must have held that pair of stockings for a while and then decided to try to put them on. I took off all my clothes in record time and was standing there totally naked. I sat down on my moms bed and separated the stockings and crossed my legs and started to roll up one of the stockings so I could slid it up my leg. I had caught my older cousin doing this so I had a clue as to what to do. My older cousin was a girl about 4 years older then me and to be honest, she was HOT. So, here I was sliding this stocking up my right leg. The feeling was electric, I then did the same thing on my left leg. I'm standing in front of the full length mirror and thinking how am I going to keep these stockings on. I then reached into the top left hand draw and came out with a garter belt. I had no idea as to how this thing went on but I figured out quickly. As soon as the garter belt was on I started to attach the garters to the tops of the stockings. It took a while but I caught on quickly. I am now looking in the full length mirror again with the erect penis sticking straight out. I figured I had to hid it so I opened another dresser draw and removed a pair of silk panties. I slid them up my nylon legs and fitted them onto my ass and my "boy bits". The feeling was amazing. At this point my mom comes home and calls me. I'm in her room wearing a pair of stockings, a garter belt and panties and no where to run. She now walks into her bedroom and sees me standing there. At first she is totally shocked to see me this way. She sits down on her bed and looks at me and asks me what am I doing. I am now nervous as a cat and really don't know what to say. So I just tell her that I'm soooo sorry for this to happen and it will never happen again, I start to slide the panties down my legs when she says to stop. She motions for me to sit next to her which I do. Mom then asks me why didn't I ask her permission to try on her lingerie first. I just looked at her with this "are you kidding me kinda' look". Mom then asks me if I want to really see what I would look like dressed as a girl. I just nod my head yes, she then gets up and goes to her closet and gets a pencil skirt, a blouse and high heels. She also gets a wig from the back of her closet and she then tells me to finish getting dressed and then she will help me with the wig. I am speechless, I mean totally speechless. I do as she asks and when I am finished getting dressed she puts the wig on my head and adjusts it. I have slipped into the high heels which btw are just a little to big but fit OK for now. Mom then has me sit at her vanity table and does my face. When she has finished she tells me to look in the mirror. I am shocked and I mean shocked to see a pretty girl looking back at me. Mom says that I look like my older cousin Janice and I do.
I don't know if mom had an idea that if she made me into a girl that I would never dress up again. Mom then said to me that for the rest of day I was to stay dressed as a girl. Mom showed me how to walk in high heels which I mastered quickly and impressed her. I helped her put her new items of clothing away and she then told me that everything that I had on was now mine. She also told that she wants to see me dressed as a girl whenever we are alone. She also told me that she was willing to take me shopping for my own wardrobe if and when I wanted to stay dressed all the time.
It didn't take me long to discover that I wanted to be a girl. I actually hated being a boy and I guess mom helped me by putting all sorts of positive thoughts into my head when we spoke as opposed to being a boy. Just the thought of wearing soft, silky things, having a nice chest that gets looked at, wearing nylons, hearing the high heels clicking on the floor, wearing makeup and having your hair done. All the things that make a girl a woman.
When I turned 17, mom asked me a very important question. She wanted to know if I REALLY wanted to become a girl. There was no hesitation in my response and I said YES YES YES. Mom then made some phone calls and I was scheduled for medical exams to become a female. At the end of almost 9 months I had all the surgeries needed to be a real woman. I had nice full C cup breasts, a vagina that could accommodate a 8 inch penis. Mom showed me how to give a man real good "head" and how to receive a lubricated penis into my vagina. I really love it when a man is pumping his cock into me and I feel him cumming. But there have been times when I prefer having that cock in my mouth so I can taste and swallow that massive load of semen.
I thank my mother everyday for helping me go from being a crossdresser to a woman. I have never looked backwards that once I was a boy. I met a guy at work one day and we hit it off right from the beginning. We became an item very shortly thereafter. I guess we were together for almost 3 months when Michael sat me down and looked me in the eye and said that he had a secret that he has to share with me. I reached out and held both his hands and discovered that his hands were as soft as mine and that he had clear nail polish on them. Not that this sort of thing was uncommon, actually it was very common. He looked me in the eye, cleared his throat and then told me that on occasion he likes to dress as a woman. I just looked at him and smiled and told him that it was alright with me and that I wanted to see him dressed. He asked me if today would be ok with me. I smiled and nodded my head yes. We went to his apartment and he asked me to give him about an hour or so. I said sure, take all the time you need. I sat on the couch, crossed my nylon legs and waited. In about 1 hour and a half I heard a pair of heels walking down the hall. I took a deep breath not knowing as to what I was going to see. Michael then walked into the living room, an absolute picture of femininity. I got up and walked over to "her" with this smile on my face and kissed "her" tenderly telling "her" how beautiful she looked. After I did a complete 360 on "her" I just had to kiss "her" and when I did the "animal passion" took control; of both of us. My hands roamed all over her body and settled on the cheeks of her ass. This enabled me to do two things, squeeze her fine looking ass and to pull her as close as I could into me. Michelle as she is now called did the same to me. Looking at us you would swear that we are 2 lesbians and to some extent you would be right. We both sat down on the couch and looked at each other. At this point I told Michelle that I want her dressed this way all the time. She just looked at me with this bewildered look and asked why. I then told her the story of my life. After that, we had a drink or two or three and started loving each other the way 2 women would. I told her I wanted her to become a real girl, like me and she said that she would REALLY consider it. Well it didn't take long for Michelle to make up her mind and now she is an "honest injin girl" like me.
Crossdressing can lead you in so many different directions, but the direction that it lead me was into womanhood. Even with all the disparities between male and female pay scale and other significant things I much prefer to be a woman.