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 passed as I got older.
I would slip on those sexy pantyhose, and my penis would get so hard 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 into 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.