Chapter 1

I have made a choice, not sure if it was the correct one, but here we are day two of my decision to see what happens.

A long time ago when I was seven, I realized that I had a strong attraction to girls’ clothes. My first memory was wearing my sisters’ panties under my pajamas. My act of borrowing her clothes grew as I got older and began to keep clothes that my sister no longer wore and hid them my closet. The clothes that got me excited most were her leotards and swimsuits. More than anything once piece swimsuits were the biggest draw to wearing women’s things.

My cross dressing grew stronger as I approached my teen years, at 12 I was regularly wearing panties to school without getting caught. On a few cold days while wearing a jacket or sweater I wore a bra to school from time to time but my dressing up was always in private.

The year of my 13th birthday was the biggest step in my dressing, I was offered the chance to dress in my sister’s cheerleader outfit for Halloween, I resisted at first, but my mom talked me into it. On Halloween my first time out fully dressed in a white and red skirt, top and bright red underpants. My mom had insisted I wear shorts under the skirt, but more than anything I wanted to wear my red satin panties I had bought just for the occasion. So, once I was dressed and make up was complete, I went to my room and took off my shorts and put the panties on then slid the shorts back on. Nobody expected anything and I left the house to meet up with my friends who all lived on the same street. My first choice made that day was to lose the shorts and stash them behind the trashcan on the side of the house. What a great feeling it was on that cool October night to walk around in a skirt and panties with everyone going along with how I was dressed and how good I looked.

When I returned home after a wonderful night of candy hording, I slipped into the shorts I had stashed and went back into my house without anyone knowing. It was a glorious night to say the least. I was tired and my parents were getting ready for bed and told me to get cleaned up. I entered the bathroom gazing into the mirror of the bathroom and enjoying how I looked, I jumped into the shower after my costume off, making sure to keep “my” panties hidden. Once I took a shower cleaning off all the makeup I went to bed.

I remember this day still 38 years later.

This was the first of many choices I’ve made over the years
To Be Continued...

Part 2

I have made a choice, not sure if it was the correct one, but here we with another of my choices, lets see what happens.

Weeks after my wonderful night on Halloween I soon turned 13, I was lucky to receive cash for my birthday from my parents and grandmother. I had a wallet full of $40 dollars burning a hole in my pocket.

Of course, my mom suggested I put it into my savings account. I had opened one up at a local back and had about $200 saved up. But me being 13, I wanted to spend it. We ended up compromising and I put $20 into my savings account.

So, the Saturday after my birthday I rode my bike to the local mall and went to Montgomery Wards to shop around. Back then they were the cheaper version of a Sears/Kohl's. Any ways they always had sales and it was my favorite place to browse. It being fall their selection was more geared toward cold weather. I browsed around until I found the clearance racks in the junior’s section. To my luck I found some one-piece swimwear on the racks and got excited.

I could not believe my luck and started to run my fingers along the gusset to get a feel of the material. It was luxurious feeling that material, I knew immediately I wanted this suit. It was a pink tank suit made by Speedo. I must have been lost in thought because I was startled when a sales lady tapped my on the shoulder to get my attention. I got scared and my heart was in my throat as I turned to the sales lady behind me.

“It’s OK, if you would like you can try that on in the fitting room.” She said and pointed over to the fitting rooms.

I was frozen in place and suddenly lost the ability to speak and mumbled something incoherent. She just grabbed the swimsuit off the rack and gently guided me to the fitting rooms. She ushered me in and closed the door. “Take all the time you need.” She quietly said.

I just stood there in that small space wondering what the hell just happened. I’ve been giving permission to try on the most beautiful swimsuit I’ve ever encountered. What to do, is all I could think about. I then ever so quietly opened the door to the fitting room and looked around. No one around, the lady must have given me some space or was helping someone else.

Now the choice, my 13-year-old then dropped that swimsuit on the floor and ran out of that store as quickly as I could, unlocked my bike and peddled as fast as I could towards home still with that $20 dollars in my wallet.

Looking back to then 1983 I could have made a different choice but was stuck with it. More choices are to come.