Dear Auntie Helga,
While I was growing up my mother and I had a small remote house in the country. My aunt and her two daughters, a couple years older than me lived in the town nearby. I was entering the 6th grade and had some unusual cravings for a boy, like what was it like to dress as a woman. It was a Saturday morning and mom had been called into work unexpectedly for the day.
We were supposed to go visit my dad who was in a Veterans Mental Hospital due to a mental breakdown. That hospital, the people who worked there and especially the patients gave me the creeps. I was relieved that we weren't going and that I would also have the day to myself.
It was going to be a special day for me indeed. I had recently received a wig that I secretly ordered from a magazine. I decided this would be a great day to get all dressed up as a girl. I started by putting on bright red nail polish. As it was drying, I added some lipstick and then my wig, and I added some barrettes with pink ribbons. I looked at myself in the mirror. I felt really weird but, wondered what it would feel like to totally dress up as a girl.
I went into mom's lingerie drawer and put on one of her lace bras and girdle. I had a couple of balloons filled with water to insert in the bra to give me some boobs. I was starting to feel flush. Then I saw her crinoline petticoat and slipped it on. I marveled at the way it hung on my body. As I was looking thru her closet, I found a beautiful white with blue flowered dress which also had netting on the skirt. It was a silky type material. I slid it on and quivered with how good it felt. It flowed beautifully over my crinoline petticoat. It took a while for me to get it zipped up the back. Finally, I looked at myself in the mirror and twirled around and squealed with delight.
All I needed now were a pair of mom's shoes and of course stockings. This was the first time I had ever worn a girdle with garters attached for the stockings. I sat down in a chair in the living room and slowly put on each stocking and clipped it into the garter.
As I stood up and looked in the mirror, I couldn't believe how I looked like a girl. It was sunny outside and I had all kinds of bundled up nerves so I decided to go outside on the swing behind the house. I loved the way my dress swished when I walked and the way the wind blew up my skirt when I was swinging. This was a wonderful feeling I had never experienced. I felt like I was in heaven...
Then shock... I heard a voice say, "Hello?" I hadn't heard my mom's car come up the driveway. I don't know who was more shocked, me or mom. I jumped out of the swing and turned around to see the startled look on her face.
I immediately asked, "What are you doing here, you aren't supposed to be home?" Mom said, "Why are you all dressed up like a girl? I got off and decided we would go see your dad after all. Let's get going!" I said, "Wait, I have to change." Mom replied, "No, you obviously wanted to be a girl today so you're going like that!' She said, grab your purse and let's go. I said, "I don't have a purse!" She said I'll get you one and you can put the lipstick you used in it."
As I got into the car I was shaking. Mom said, "I can't believe you dressed completely like a girl all by yourself." I was really nervous. Mom asked, "Why did you dress up like a girl today? Is this the first time? I just answered, "Because!" I couldn't think of any excuse or reason why. I wondered what I had gotten myself into and how I could possibly go to the mental hospital to see my dad.
It was about to get worse. She said we had to stop for a couple minutes at my aunt's house. When we pulled up to my aunts, I prayed that I would not have to get out. Mom handed me a package from the back seat and told me to take it into my aunt.
I reluctantly took the package and walked up to the front door. It was locked so I had to ring the doorbell. I hoped my aunt would answer but, instead one of my cousins answered the door. When I told her, I had a package for her mom started laughing. She yelled to her mom, "Billie is here with a package for you and he is dressed like a girl!" Her sister, along with a friend from school came out and they both started giggling when they saw me. My aunt came in to the living room and started to giggle when she saw me and said, "Aren't you a pretty girl and such a pretty dress!"
Mom finally came in the house. My Mom told my aunt she came home and found me dressed this way and decided to have me stay dressed up to go see my dad. My mom then made me describe the process of how I got completely dressed up as a girl for my aunt, her two daughters. My aunt thought it was a great idea to keep me dressed up as a girl especially since I had done this myself. My aunt said that she had some hand me down dresses that would probably fit me and she would round them up if we had a couple of minutes. Mom said, "OK, but hurry." My aunt gathered up a few dresses and gave them to me saying." These should look cute on you; you make a pretty girl!
We went back to the car and as we drove off mom said, "It looks like you have some dresses of your own which you will be wearing!
It was a little over an hour and a half drive to the hospital. We always stopped at the restaurant mom worked at to grab a bite before the trip. Today was no exception despite my protests.
I knew all the waitresses and they all knew me. As we walked in, I could feel my dress swish as I walked and I had the purse mom gave me over my shoulder. It was busy when we got there and a host seated us with a big smile on her face said, "Are you ladies out for the day?" I replied, "Yes!" One by one, each of the waitresses came over to talk to us and take a good look at me with a big smile.
Finally, back in the car and driving to see dad I had gotten used to the idea of being a girl for the day. It was windy out and Mom said, "Be sure and hold down your dress so your panties don't show." Mom said, "You need to touch up your lipstick first before we go in."
The walk up to the main doors of the Mental Hospital seemed like it would never end. I was busy trying to hold down my skirt in the windy weather. As we walked up to the counter to check in a nurse recognized my mom and said, "Hi, who is the girl with you?" Mom said, "Oh that's my son Billie, he decided he wanted to dress up like a girl today?" The nurse giggled and said, "He's so pretty as a girl, you should keep him that way."
My dad was in a large room with a lot of other patients and a couple of nurses who knew my Mom. My Dad was shocked to see me all dressed up like a girl and asked my mom why she dressed me this way. Mom replied that she came home and found me all dressed up and that I did it all on my own. Dad asked me if it was true and I sheepishly said, "Yes, daddy!"
The day seemed to drag by. I was especially embarrassed when Mom, Dad, and I had to go in and meet with his shrink. Mom made me tell the shrink that I had completely dressed myself up on my own because I thought I would be alone at home and then she caught me swinging when she came home unexpectedly. It felt so strange and scary to be telling this to a shrink in a weird mental hospital. The shrink asked me a lot of weird questions and then asked my mom if I would be coming dressed as a girl again and my mom assured him that I would be coming as a girl always from now on.
When it was over on the way home Mom said I had much better manners as a girl. We went to see my dad every two weeks that summer and each time I was completely dressed as a girl in one of the dresses my auntie gave mom for me. Nothing was ever the same after that day. I was always treated like a Sissie by my aunt and cousins.
Thank you for your letter Sheila. A young boy's curiosity, many boys have these feelings, few have the will to try and though you were caught, you still had those special feelings as you dressed. What a wonderful start to I assume a lifetime of being a sissy. We would love to hear more about what happened after you were caught and they treated you like a sissy.