My life as a cum-guzzling-gutter-whore Part 1: The Introduction

The first time I was exposed to feminization and with it sex with another person was around the time I was 14. I had lost my role-model and close friend a couple of years before that and was from a rather broken home that never really communicated. I stayed to myself and in addition my father really didn’t pay much attention to me either. A few months before summer vacation started an old family friend stopped by and started taking me out to hang out every Saturday. I enjoyed my time with him as I finally had someone paying attention to me. After a few weekends like that he asked if I could stay the night since it was getting later and later each time. I saw no problem so I agreed with him. A couple of weeks later it was raining pretty hard and cold and by the time we got to his apartment I was soaked to the bone. He offered that I take a hot shower so I wouldn’t catch a cold. Thinking nothing of it I agreed and readily went to the bathroom to get into the shower. As I finished and stepped out, drying myself off I noticed that my clothes were not hanging up as I had them before getting in the shower. I stepped out looking down the hallway towards the living room and saw him sitting on the couch staring at the TV intently. I called out to him asking where my clothes were and without even looking in my direction he explained that they were in the dryer and wouldn’t be done for a while but that he had set out some clothes on the bed in his room. I quickly made my way across the hall to the bedroom and stopped short with what I saw. On the bed was definately a set of clothes but rather they were girls clothes..right down to the undergarments. Confused I shouted out to him asking if this was a joke and he replied that it wasn’t but those were the only clothes he had that would fit me. After a couple of minutes of standing in nothing but a towel I decided to say to hell with it and amuse him.

I quickly dropped my towel thinking to myself how much of a laugh we would have once this was all done and over. I put on the bra and panties first, followed by the stockings and blouse/skirt. Looking around I saw a pair of platform heels set out and laughing decided to put them on too.