Tina Marie's Special Halloween

Well, it was not the first time I had dressed up as a girl, but it was certainly the first time that my mom and dad "encouraged" me. It was the early sixties, and like many of you, I was a 10 year old catholic boy with an older sister. My mom and dad both worked and I was home quite a bit by myself after school and during the summer break, which is when I began to find my way into my older sister's closet. I had been dressed up as a girl before by my mom when I was very young, and my dad had often told me how they had wanted another girl, when they were surprised with their son being born instead. I had also been dressed as a girl one night by some friends of the family who had 5 daughters. I remember how much my dad had enjoyed seeing me dressed that way..  (I think I was about 5 or 6 when that happened) Now, bored in the summer, I explored my sister's clothes and found her pettipants. They were so soft and so cute and they had a white fringe around the legs; I tried them on and was in heaven. Venturing down into our basement, I found a drawer filled with a couple of full petticoats. I really liked this, and every day I found more clothes of either my sister's (she was a few years older). The pettipants and petticoats were just something I became addicted to, as well as dressing up every chance I had, which was about every day during the summer. I just could not stop myself - I really liked dressing as a girl.

One day, I tied a scarf over my head and went out the back door and down through our alley to the corner. I was so nervous, but so excited at the same time. I did not know that one of my friend's moms saw me from her apartment window (they lived in a three flat), and, later that week, I was at his house playing and she said to me, "I saw your sister the other day walking down the alley - she is certainly a pretty girl." I could not believe my ears!

While I enjoyed this dressing up, I did keep it a secret, thinking that no one knew this was going on; I did  not realize my mother had known about this (and I am sure she had told my dad about it as well).  My father, for his part, had always wanted a second daughter and made no secret of it; he tried to cover it up, but I knew his true feelings. One Halloween, many of the boys in the neighborhood decided to dress as girls for Halloween. They were just going to wear their mom's dresses with their pants pulled up or wearing shorts underneath. One of my friends said he was going to wear his sister's penny loafers with socks.  When I mentioned it to my mom one night, she asked me if I wanted to do this as well. Of course I did, but I pretended to not be interested.. She was a bit surprised I think, and my dad seemed genuinely disappointed. He said, "Well, if your friends are going to do it, don't you think it would be fun to try it too?"  That's when my mom took me aside and told me she knew I had been dressing in my sister's clothes, and in her clothes from the basement as well, and that it would be so nice for my dad if she helped me become the second daughter he had always wanted.  I agreed...much to my dad's delight. 

Mom took me into my room and told me to wait, then came back in a short time from the attic and the basement where many of my sisters clothes were stored, which she had outgrown. I learned later that my mom had many of her clothes stored down there as well -  I just had not yet found them. As I was only 10, there was no facial or leg hair to deal with and the clothes fit very well (which I knew they would). First, there was the nylon panties, followed by a long led panty girdle with garters, as pantyhose were not around at the time. Then there were the stockings (which felt so good), and it felt embarrassing, but nice, to have my mom helping me. Then came a bra which fit well, but my mom still added a couple of foam liners for some extra fullness. Then four frilly petticoats which I had never seen before!  Next came a very full skirted dress which zipped up the back. I could not believe how full the dress was with all of the petticoats, as I had only found one petticoat in my sister's closet to try on.  Of course, with all of the petticoats, the dress came above my knees, and Mom told me to be careful when I was out, as the least little breeze or movement might cause my petticoats to come up and show off my girdle and stockings. (She just giggled and I really did not know why at the time) Mom had a couple of wigs she used for work and she found one that was shoulder length and, with a bit of blush and lipstick, I turned around to see a copy of my sister...but it was me! Of course, my mother was delighted, but not half as much as my dad, who called me his "little girl."  He walked around me and smiled and then gave a a bid hug and told me honestly that he had always wanted another daughter; not that he was disappointed with a son, but he just wanted another girl in the house and now he had that little girl with "his" Tina Marie. I had never seen my dad smile that big - I knew he was really happy about this. Well, this year my dad insisted on taking his new little girl out trick or treating and kept telling me what a cute little girl I was and how much he loved having another daughter.

     As we went down the block, he held my hand and told me not to be scared because I was a cute girl and he was here to protect me. As we continued walking, a gentle gust of wind came and, sure enough, it blew my dress up, revealing all of my petticoats. My dad thought this funny and cute. He said "You will have all the boys following you so they can watch that happen."

We finally got to the corner where I would meet up with my friends but no one recognized me. They said hello to my dad and asked who I was, and I was so shy I could not even speak. My dad said why this is my "other" daughter, Tina Marie, but you probably know her as Tommy. Well, the look of shock on my friends' faces was amazing, and they did not believe him at first. They came over and looked at me closely, and one of them finally said "Yeah, it's him!"

Then, my dad said, "Don't you mean it's her?" Well, they thought this was so funny and said, "Yes, it is her - she really is a cute girl. They did not stop their teasing, and soon some of their older sisters saw me and could not believe this either. My dad was just beaming the whole time, and when one of the older girls raised my skirt she said, "Oh, look at the beautiful petticoats she has on and the cute girdle too."  After she had said that, my friends wanted to see that too.

I was so embarrassed, and my friends came over, lifting my skirt up  but my dad intervened and told them that the wind would do a fine job of blowing up my skirt! I could not believe he had said that. Of course, they all followed me as we went door to door trick or treating for the rest of the evening, and every time the wind would blow my skirt, they would all whistle or shout. Since I was holding on to my trick or treat bag in one hand and my dad's hand with the other, there was little I could do when the wind blew my skirt up.

Everyone talked about Tina Marie's petticoats and girdle the rest of the night (and the next day at school too). My dad kept encouraging me to behave like a girl and to not be afraid to show off my petticoats. By the end of the night my friends asked me if I could just become Tina Marie all of the time. I could not believe what was happening - they actually liked me more as a girl than as a clumsy boy who did not play baseball very well. My dad heard one of them say that and he turned to them and said, "Would you really like to have her in a dress all the time?" They replied Yes! My dad said he would have to think about it and then said, "You know, if she was dressed that way, she could no longer play sports or do boy things and she would have to be looked after as she was a girl."

My friends all promised they would take care of me and watch out for me, and that I was not very good at sports anyway and they would love having me watch them play instead. After that night, my life really changed and during the summer break, they enjoyed having a new friend, Tina Marie, who they took care of and watched over as long as "she" was dressed as a girl and did not try to be one of the guys. In fact, my mom and sister made sure that I had plenty of dresses and petticoats to wear through the summer months, much to the enjoyment of my friends. I also was more accepted by the girls in the neighborhood, but that's another story. There are more stories yet to come, and I will send more if dear Tessy will publish them for me.


Return to Main "First Encounters" Page

Return to Petticoat Pond's Main Page