Two years later, I discovered my older sister's panties. The first pair I wore was a pink nylon pair of panties. I would wear then for a couple of days undr my boy pants and then drop them in the laundry. After my Mother would do the laundry, I would sneek in my sister's room and retrive them. When my sister started wearing a training bra, so did I. I even remember trying on her Playtex living girdle and wearing them for a day or two.
I got caught one day and had the "Why boys don't wear womens clothes" talk. I stopped trying on my sisters stuff for several years. I also tried to be as macho as I could.
At 10 years old, I started wearing my sisters bras and panties again. It started when i did my own laundry one day and hadd to empty the dryer. It was filled with my older sisters clothes. I not only tried on her underwear but I also tried on several of her jeans and a skirt. I still to this day remember that poodle skirt.
For almost a year, I was wearing panties and during the cooler weather a bra every day. I even started trying on her slips and dresses when I was home alone. I was found out by a guy I knew and stopped when he threatened to tell everyone about my dressing (he saw the outline of my bra when I took my jacket off).
At 15, I moved to my Father's house with my step family. I discovered that my step Mom and I were the same size. Since they both worked and got home late, I was in charge of most of the household chores. This not only included the cleaning but also taking care of my little step-brothers. I would come home from school before the boys, would change and start dinner.
I even started thinking and acting like I was their Mother. I was in almost heaven. I remember how good it felt when they would snuggle up with me while we would watch TV. And when I would put them to bed and they would kiss me good night. The youngest one, my 6 year old, would sometimes slip up and call me Mommy. It made me cry several times because it made me feel so good to have someone call me Mommy
I stopped wearing boy underwear even at school. I just felt so natural. I always wore a baggy shirt, girls jeans and sometimes girls shoes. A girl at school pointed out that I should be careful because on several occasions she noticed how I was dressed and that several times she noticed that I was wearing a bra. After a long talk we became good friends. We even would go shopping for bras and panties for me. I soon had my own clothes to wear and stopped wearing my step-mothers stuff.
I found out that she was a lesbian and I was still trying to figure myself out. It worked out good for both of us. Her family thought she was dating boys and mine thought that I had a girl friend. Several times when my parents would stay over because of working late (?), Jill and I would try on different types of makeup and hair styles (Loved them 60's hair styles).
I lived there for almost 2 years when my step-Mother caught me. She walked into the bathroom as I was getting dressed for school. After the boys left for school, she and my Father started in on me about if I was gay, etc. etc. I tried to explain but they didn't want to hear it. I was told that they didn't want me around their children and that it was best if I went back with my Mother. They told me that nothing would be said about the matter because it would break my Mother's heart to find out that she had a faggot for a son.
I went back and swore that I would never wear womens clothes ever again. i became the biggest macho man that I could. Started lifting weights and taking protein drinks to build muscle. At 18 I joined the military.
For almost 3 years, I didn't even think about clothes till I was doing my laundry and found that one of the married guys used one of the dryers in the dorm. I found a pair of panties in one and those old feeling came spilling out. I went into town and bought myself a few pair of panties and a couple of bras. I would wear them under my uniform whenever I knew I could get away with it.
I think I should end this bio here since the topic was how it all started and not my whole life
Sorry I got long winded but it all just started spilling out.
