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Crossdressing True Confessions, Part One

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with. She would drive me crazy when she donned a pair of pantyhose and heels with a short skirt. She didn't know it, but she would not have been able to keep my hands off of her legs and ass in such an outfit. Our sex life was good, but mostly it would be a nice dinner, ending up in the missionary position. She would never go down on me, and I barely went down on her. We were stuck in the same cycle of sexual contact that after a while, sex altogether just stopped. We would have our moments, celebrating a new job or a weekend together when we just had time to ourselves. However, they were few and far between. I learned to service myself more and more to keep from blowing a gasket. I was always curious about dressing as a woman, remembering when I was younger trying on my older sister's clothes and getting so excited wearing pantyhose and heels, but the feeling past as I got older. I would slip on those sexy pantyhose my penis would get so hard and I would cum in the hose with just a few rubs. I found myself fantasizing about it all over again now that Myrtle and I had all but ceased sexual contact. I am about 5'10" and thin at 185 lbs. I always had very feminine features and with a good wig, I could easily pass as a woman (a few eyebrow plucks would help). I was in theater in high school, so I wasn't afraid around make-up and wigs. I had worn my sister's heels so that didn't worry me either, a lap or two around the house and I would get the walk down. I am sad to say to that my cock was not a large and cumbersome thing, although at times I wished it was. Some control top pantyhose would do the trick on hiding my male member. I fantasized about dressing again and again even checking out a few online stores to purchase the right size heels, dresses, and wigs. My fantasies went on for quite a long time. Finally the day arrived when Myrtle told me that she would be going to Chicago for some business. She would be gone for a week. I tried to sound disappointed, but in the back of my head I knew that I was going to order the dresses, wigs and heels and become a woman for the week. She would leave on a Monday and return the next Monday. She had asked if I could take a few days off and come with her. I quickly made some story about one of our biggest clients would be in town that week, and it wouldn't be wise to take off just then. She seemed disappointed, but never raised the question again. I knew she would not understand my little week I was planning so I needed to get what I needed without Myrtle's knowledge. I opened a new credit card under my name only and ordered some size 8 black heel pumps with 4 inch heels. I also got a couple pairs of control top pantyhose, black and white sheer stockings, two black knee length dresses, a brown wig, and some jewelry. I also purchased some breast fillers and corset tops to wear as well. The corset would help with my upper body figure and the breast fillers would come in a size c, a cup size bigger than my wife. I scheduled everything to arrive at the house the Monday Myrtle was leaving. I took some time off from work, telling them that I would be going to Florida for some R&R. I told them to forward all my work calls to my cell phone. Even if Myrtle was going to call my office, she would still get a hold of me and wouldn't arouse much suspicion. It was setting up to be a perfect week being a woman. And when the weekend arrived before Myrtle's trip, I couldn't wait to do some light makeup shopping and settle in to silky, feminine clothes. I had a hard on all day Sunday counting the hours until her plane would be in the air and I would be at home slipping in to some sexy hose. I helped her pack and told her I took a half day to take her to the airport. As I carried her bag through the terminal my mind was fantasizing about my heels and dresses. I kissed Myrtle passionately before she went through security and we promised to call each other when we had the chance. As soon as she had left, I jumped back in the car and went to the drug store and purchased makeup and some hair-removal wax to thin out my eyebrows and soften my beard growth. I spent the rest of the morning shaving my body. I really couldn't believe that I was going all out for this fantasy. After my shower, I couldn't stop touching my smooth legs and underarms as I used what ever my wife left for lotion and perfume. Next were my eyebrows, which I took the wax and began to painfully shape my brow for a more girly look. I stepped back to look at my more girlish face. I almost didn't recognize myself around my eyes, and I smiled broadly as I looked back at a more womanly me, and I had yet to apply any makeup. As I was feeling proud of myself, the door bell rang. I ignored the weird look I got from the delivery man and tore into the package as soon as he left. I could hardly contain my excitement as I pulled out black heels and long black gowns. I slipped out of my robe, my penis was hard and erect. I knew, I wouldn't be able to pass as a woman with my johnson so rock hard, so I went to my wife's dresser and pulled a pair of her silk stockings that she wore at our wedding. I rubbed my cock with it for a few seconds and was surprised how quickly and how much cum I shot out. With that out of the way I took a few minutes to recompose myself and began open the rest of the shipment and begin dressing. First I pulled out the tan control top hose and slipped them on. The feeling of pantyhose sliding up my long smooth hairless legs was exhilarating. I tried my best to keep my hormones under control. Next I fitted the corset and wrapped it around my body. The breast inserts fit perfectly into the cups and I felt womanly as I moved it into place. As I looked down I couldn't believe how my body was being transformed in to something so sexy. Next was the brown wig that was shoulder length, I fitted it on my head and moved it around. I didn't spend much time styling the hair, which was a good thing. I don't think I could spend the time doing it up. I stood back and looked at myself in the mirror. I felt my manhood start to get aroused once more. I was barely able to recognize myself as I looked on. With a little sexy make-up I doubt I could be mistaken at all as a man in drag. I looked that good. I turned and rubbed my hands all over my flat stomach and legs. My cock again began to grow so I thought of anything other than my body in sexy hose and corset. My hands shook a little as I began applying my makeup. A little rogue and some lipstick and eyeliner, I was beginning to become more and more of a woman. When I finished with make-up and tried not to dwell on my face and carefully slipped into one of my black dresses. The dress fit like a glove, even around my bust and hips. My sister's dresses never fit, and wearing Myrtle's things was really out of the question, they would just be too tight and rip at the seams. I just never wore anything that was this womanly that fit me. It was black dress that was tight with spaghetti straps and was about knee length. It had a white lace trim at the top and on the hem. A small skinny belt went around the waist. I pulled out some black sheer stockings I ordered and slipped them on over the tan hose. I sat on the bed and fixed the stockings to the garter straps on the corset. Catching myself in the mirror, I once again could not believe it was really me looking back. I stood in the full length mirror and posed and shot a "come fuck me" look in the mirror. I would lean to show my cleavage, which it was a pleasant surprise with the corset creating a natural looking cleavage. Then I realized something, I was turning myself on. To the passing eye, I was an athletic tall brown haired woman with long beautiful legs and slight hour glass look to my body. I was so excited, I could not longer hide my arousal through the pantyhose, a definite outline of a cock surfaced at my crotch. I thought I was going to cum right in the pantyhose. I didn't want the experience to end after a few moments dressed. I did everything I could to not think about it. I finally had to vacuum the house in heels and a dress to finally get myself used to walking, and for my cock to shrink back to nonexistent. Trying to keep from getting aroused again I practiced on my walk and sitting up and down with a dress on. I was surprised how easily I picked up sitting up straight as a girl and keeping my knees together as I stood up and sat down. I also worked on a feminine voice, which wasn't hard for me in the first place. Many telemarketers would call me ma'am on the phone when I would answer. I practiced in the bathroom where the echo would help out, and then I called a few numbers to friends as a telemarketer to see if I could pass as a woman. It only took the first call as I tricked a friend of my wife's. I even flirted a little with him, surprised how easy it was. I was feeling pretty good about how I looked and how it felt. I finally worked up my courage and slipped out of the house after dark and took Myrtle's car, a little convertible, and took a drive toward downtown. I packed one of my wife's purses, and made sure I had everything a girl would have, even some tampons. I also slipped on a pair of black panties to go over the hose for added security that my little johnson wouldn't make an appearance. I touched up my makeup and gave a final look in the full length mirror. I was surprised how womanly I looked. Finally I tied one of Myrtle's scarves around my neck and adorned jewelry. My heart was in my throat as my heels clicked on the garage floor and I unlocked the red convertible.