When and why I started to crossdress is unimportant. Read any bio of a crossdresser and that is my story as well. However, my story has a bit of a twist that probably few crossdressers have ever experienced. Perhaps the story you might find sick and revolting, or perhaps you might find it titillating and rather erotic. Well here goes.
I was in my teens and had been dressing for a while. I never really had the opportunity to really come out with makeup and try to look really appealing as a girl. On this particular Friday, I was home from school because of a holiday. I knew my mother was working and often went out with the girls after work on Fridays and would be returning well after midnight. My father too was going to be out with his bowling league after his work ended so I literally had the whole day and a good part of the evening to work on my transformation into the pretty girl I knew I could become.
First, I jumped into the shower and shaved all of my body hair. As I shaved my ass and around my penis, I could feel the blood rushing to my organ making it pulsating. Already I was excited and the change had only just begun.
I stepped out of the shower and powdered myself down with a sweet smelling aroma that kept me hard. I powdered myself all over especially in my private areas. I felt a girl must smell the freshest in those areas. It must be a turn on for a man to have his woman smelling so nice.
I stood nude before the long mirror in my mother's dressing room and admired my shaved body. There were still patches of white powder where I had not completely rubbed in the sweet smelling dust. I then wondered what to do next. I had often caught glimpses of my mother sitting at her dressing table putting on her makeup and figured that this must be the next step.
I sat down where I had seen her often do and searched her makeup table to see what I should start with. I had found a magazine which described, for young teenage girls, the proper way of applying makeup. I felt this would help me.
First, I took a bottle of a tan colored liquid which was referred to as a foundation. I applied this to my face, neck and forehead. I smoothed it and watched in amazement as the liquid dried and changed the tone of my skin. I then found a compact case with blush. I followed the magazine and took the brush from the case and applied the pink powder to my cheeks. When I finally applied the lipstick, I really got an erection. I followed this up with lip gloss.
The next part I felt was probably the most crucial and the part which made you passable or not, the application of the eye makeup. Too much and you look like a clown and not enough, then why bother. First I applied eyeliner to both my upper and lower eyelid. I was very careful not to apply too much. The mascara was next. I applied just enough to give my eyes a little bit of depth. Finally a little eye shadow on the eyelids. I then found a case with false eyelashes. I had some difficulty applying the eyelashes and getting them straight, but when I was finished I saw that it was worth the effort.
The final touch was the wearing of one of my mother's wigs. She was dark haired, almost black, but had a few dark haired wigs of different styles to wear when going out or when she didn't have time to set her hair. I took one which had long flowing hair that would hang over my shoulders and that I could sweep over one side of my face.
I stared at myself in the mirror for quite some time, admiring what I had just done. It was truly a work of art.. I couldn't believe how much I looked like my mother. As I was growing up, relatives would say how much I looked like her but of course I could never see it. She was a female and I was a male. How could there be any resemblance. But now that I had completed my transformation, and we were now both female, we could have passed for sisters. My mother is statuesque at 5'10" and a slim figure of slightly over 120 pounds. Although we are about the same height, I do have a few more pounds although it would probably not show in a dress of hers. We will just have to see.
I went to my mother's lingerie drawer and shuffled through the various undergarments until I found what I wanted to try on first. I thought that since I would be dressing all day long that I would be wearing most of her lingerie anyway.
I pulled out a pair of black panties, a black bra, a black garter belt and black stockings. I put on the undergarments and all went well until I tried to put on the panties. My cock was so hard that the panties didn't fit. I had heard about tucking, but I had never tried it and didn't know how it was done. I pulled my cock as far back toward my asshole as it would go and the took adhesive tape and wrapped it around my cock and taped it to my legs. When I looked at myself in the mirror, all I could see was what looked like a cunt between my legs. The look was very exciting and I could feel the bulge straining at the tape to free itself from the harness. I knew that I would most certainly be in this state the majority of the day so I better get used to it.
I realized as I stood there in my bra, panties, garter belt and stockings that I had made no provision for tits. I thought a bit and looked around and found a pair of surgical gloves. I tied off the fingers. Inverted the gloves and filled each one with water. I then tied off the open end and inserted them into my flattened bra. As I did this, I realized that if I placed the end that I tied off against the inside of the bra, that I could create the appearance of an erect nipple. They also had a slight bounce to them as I walked.
Now, what to wear. I went to my mother's closet and searched for just the right outfit. She had long dresses, gowns, short skirts, slacks, shorts and whatever else you could imagine. I remembered that at a Halloween party a year ago that my mother dressed as a hooker. It was a party where you dressed in the least outfit that conformed to your life style. I searched and found the outfit stuck in the back of the closet. It was a mini skirt and tight white sweater. I couldn't wait to try them on. To my amazement, I looked terrific. Everything fit in just the right places. The only thing remaining were the shoes.
I remembered that they were black patent heels. The heel was much higher than she normally wore. They too were in the back of the closet. I knew that you couldn't stretch the shoes as you could the sweater or skirt, so I was worried that they wouldn't fit. I found the box and they were a size 9. I had no idea how that size related to a men's size. I tried them on and they were very tight. I could hardly get them on my feet. Then I took some of the powder that I used on my body and sprinkled some on my feet to act as a type of lubricant. The shoes slipped on easily and fit like a glove.
I couldn't wait to get to the mirror. Well, you can imagine the surprised look on my face when I saw my mother staring back at me. I thought my cock was going to rip the tape it got so hard. I touched myself and before I knew it I was shooting hot cum up my ass. My stiff cock never went down, but I kept my hands away from it in order to avoid another accident.
Well, I said the story had a twist. I stayed dressed all afternoon and into the evening, prancing around, admiring myself in the mirror, and I guess fatigue set in. Oh by the way, I did jerk off a few more times. Typical I guess. I laid down on the couch for just a couple of minutes and of course fell asleep.
All of a sudden, I was awakened by a door shutting. I looked and it was my father. The room was dim and he was a little high from alcohol. I saw me on the couch and came over to me, thinking it was my mother. He started saying things like, "you must feel like my little whore tonight, well I'm going to pay you and get my money's worth. He started to touch my tits and squeeze them. He had no idea that they weren't real. He then put his hand under my skirt and started to fondle my cunt. I was ready to explode again and scared at the same time. I really didn't know what to do except to try and moan in my most feminine voice.
All of a sudden my father grabbed my hand and put it on his bulging prick. He said "I know what you want, but tonight you're going to suck it first. I really started to panic. Did he really want me to blow him. I never did that before. He unzipped his pants and put his cock against my mouth. I licked it and tasted some pre-cum. I was caught between throwing up or enjoying it. I really had no choice if I were to continue with my charade. I opened my mouth and started to kiss his meat and let him slip it in. I rolled my tongue over it He kept driving it deeper and deeper into my mouth and had to struggle to keep from gagging. The deeper he drove, the harder I sucked. I started to touch his balls and he moved my hand so I could put a finger up his ass. I could feel him pulsating and knew what was about to happen. Suddenly he started to jerk as his hot load shot into my mouth. I kept sucking and swallowing until all his load tricked down my throat. He didn't want me to stop, so I continued to suck until he got hard again. "Monica", he said, "That was the best blow job I ever had. Not I'm going to top it off with something you never allowed me to do. Since you are my whore tonight, whore's do whatever their johns want. I'm going to fuck you up the ass." I almost passed out from the thought.
My father got on his knees and pulled down my panties. I was hoping that the tape wouldn't show or that he wouldn't grab for a pussy and find my cock. He thrust his tongue into my asshole and started to lick and suck. When he felt that I was moist enough, he slowly slid his very hard dick up my ass. I started to move back and forth as he moved getting his cock deeper and deeper inside me. I shot my load and my moans must have excited him more as he worked faster and faster until he could no longer hold back. Again I felt his hot load inside me. I must admit that I enjoyed the experience.. When he was finished, he lay down beside me and started to kiss me on the lips and put his tongue inside my mouth. Slowly he drifted off to sleep. I escaped from his embrace as he slept on the couch. I got up and went into my room and sat down on my bed and started to weep. I guess from excitement, fear, pain and thought of what happens when he tries this on my mother.
I don't know how long I sat there, but I never heard the footsteps coming into my room. I looked up in a start expecting to see my father, but it was my mother. She looked down at me, still fully dressed and said, "You look close enough to be my sister. I will call you Michelle and you will call me Monica." I didn't know what to make of the whole thing. Monica sat down on the bed next to me and cradled me in her arms, assuring me that there was nothing to fear. She slowly unbuttoned her blouse exposing a white brassier. She said, "Michelle, do you like what you see and would you like to see more?" I replied, "Yes, Monica, I want to see more." She took my hand and put it on her breast, then lifted her bra exposing a beautiful set of tits. "Monica, I want you to suck them for me." As I did, she put her hand under my skirt and freed my cock from its harness.
I sucked on her tits as she stroked my cock up and down. As her nipples became harder, so did my cock. She bent down and started to lick my shaft. Then she positioned herself in such a manner that her pussy was in my face. I started to lick it and stuck my tongue inside her. Monica loved this. Her hips start to gyrate as she sucked on me harder and harder. I felt a sensation in my balls as she stuck her fingers up my ass. I was so excited, I could no longer hold back and I shot my hot load into Monica's mouth. She only continued to suck as I felt she was reaching ecstasy herself. She too kissed me on the mouth and put her tongue deep inside me. I was so exhausted that I fell off to sleep.
When I awoke, I was in bed in my pajamas and all the makeup was removed. I don't know where the clothing went to, but I'm sure I could find it again. I don't know what will happen or if these episodes will ever be mentioned again or if they will repeat themselves.. I do know that it was the greatest night of my life.