A journey to becoming a sissy slut

I can say that I’ve lived a rather ordinary life. Having been married for 22 years, raising a few children, and even retiring from a job after 20 years, my life has been rather full, but ordinary. This wasn’t always the case and looking back I sometimes wonder what my life would have been like if I had been able to follow a different path, one that I lived for almost five years of my life and one that I will never forget. I guess I should start at the beginning.

When I was a teenager, I went through a very tragic moment in my life. My cousin, who was like an older brother to me, passed away and left me in a very dark place in my mind. Seeing as how he was pretty much the only member of my family who I talked to or that paid any attention to me, his loss left a gaping hole in me that I never thought would be filled.

That was until a few weeks after the funeral a family friend, Henry, stopped by my house. Being as he was much older then me and I figured he was there to see my father, who lived with, but was either working late or romancing whatever girlfriend he currently had. When I told him this he shocked me when he said he was there to see me and wanted to see if I wanted to hang out with him. I was in such amazement that I had no idea what to do, but we started hanging out, going to different places, and even just chilling over at his house. Since it was summer I was able to spend more and more time with him, eventually being able to spend the night or the weekend with him. Every time we hung out I would look at him and see his smile, a smile that warmed me to the core, and a smile that would lead to more things. After about a month of spending time with him is when things took a serious twist.

We were hanging out at his house and since it was a hot summer day we were out back and decided to have a water fight. I got him a few times but he had decidedly won since I was soaked from head to toe. We were heading in when a blast from the A/C send a shiver through my body. He told me to go ahead and get a hot shower before I got sick so I made my way to the bathroom trying not to drip water everywhere. When I got there I stripped down and got in, enjoying the hot water compared to the cold wet clothes I had dropped in a pile on the floor. When I went to use the soap and shampoo I was a little confused because all I saw were feminine type products. Shrugging it off I used the soap and shampoo and enjoyed the flowery fragrance they left on me. When I finished I stepped out and dried myself off with the fluffy towel left for me. Looking around I finally noticed that the pile of clothes I had left on the floor were no longer where I had left them. I made my way down the hall to the living room where I saw Henry sitting on the couch, shirtless, watching something on the TV that he quickly paused as soon as he noticed me in the hallway. I asked where my clothes were and he told me they were being dried but he might have something for me to wear in his bedroom.

I followed him and sat on the bed, wrapped in the towel, the cold air starting to put goosebumps on my skin, while he searched through his closet. Finally he produced a large bag and smiled as he showed it to me and then proceeded to dump the contents onto the bed. I was shocked and really confused with what I saw. He told me all he had was his little sisters old Halloween costume that would fit me and what was on the bed started to make sense. There was a pair of black lace panties and matching bra, a plaid mini skirt, a white tie blouse, a pair of thigh high white stockings, and a pair of shiny black flats. I looked at the items and pondered whether to wait for my clothes or just suck it up. Another shiver running up my spine from the cold A/C made the choice rather easier. I bit my lip as I decided to just put the clothes on as opposed to sitting around in the cold in just a towel.