I consider myself somewhat lucky.  For whatever reason, I've been enamored with the soft, silkiness of girls' underthings, poufy slips and petticoats, and frilly party dresses from the time I was a young boy.  Why was I lucky?  Because I had an accepting mother and a sister (the only sister in a family of five children) who would indulge me in my love of feminine clothing.  Because I was the closest in age to my sister, my father kind of turned a blind eye to our dress-up activities.  He must've thought, "What's the harm?  He'll grow out of it."  He probably thought that I did; however, that wasn't the case. 

We (my sister, younger brothers and I, and even a girl and a boy cousin who were close to us in age) would often play dress-up, then put on fashion shows for the adults whenever my aunt, uncle and their family came to visit or when we went to visit them.  (In the late 60s, our families visited each other a couple of times a month, so it afforded us a lot of opportunities to engage in my favorite activity.)  I was a late bloomer -- I didn't reach my full size until I was a senior in high school.  Until that time, my physique more closely resembled that of a young girl.  The only thing that didn't give me pleasure in my cross-dressing was the bullying and taunting of my older brother.  Larry was ashamed of me because he was big for his age and very athletic.  He excelled in sports in both junior and senior high school.  He wanted me to be just like him, and he had a hard time accepting the fact that I wasn't.  Mind you, I was good at sports and I liked them, it's just that I didn't make the school teams because I wasn't big enough.  But, I digress.
 My father worked two jobs and wasn't around an awful lot in my early youth.  Because of his absence, Larry punched and kicked me more times than I can count, to try to toughen me up and to let me know that he didn't approve of my activities with Linda and Cindy (my sister and girl cousin).  I don't doubt that some of Larry's kidney punches and shots to my ribs contributed to my slow growth rate.  Well, his punishment wasn't too much of a secret -- most of our extended family knew about it.  One summer, my aunt (my mother's sister, whom I love greatly) came to my rescue.  It was the summer of 1970 -- three months before I would turn 11.  All of the stars must've been in alignment for the following scenario to unfold.  I don't know why or how it happened, but I'm glad that it did.
My uncle, Richard, was a college professor, but he had taken a sabbatical to finish up the requirements for his doctorate degree.  The school where he was doing the work was three states away.  They had returned to our state just the year before (after a 2-year separation), and the two kids in the family had wanted to go with their dad for the summer to spend time with a family that they had grown very close to in Oklahoma.  My aunt couldn't join the family because she had to take care of the upkeep on the home, ensure that their monthly bills were being paid, and be available for a niece on the other side of the family who was getting married.  Because she didn't want to be alone all summer, and knowing that my sister wasn't going to be available at the time she needed her, Aunt Meryl had asked if I would be willing to spend a couple of weeks with her, if for no other reason than to get me out of the situation with Larry for awhile.  I readily agreed, not knowing that my cousins weren't going to be around or what she I and would be doing in those few weeks.

The afternoon we arrived at her house; Aunt Meryl said, "Go run around for awhile, Ally, but don't get dirty, okay?"  (I thought it odd that she referred to me using the feminine connotation of my name, but I didn't question her.)  When I asked where Cindy and Jon were, it was then that I found out that they were in Oklahoma and wouldn't be available at all during my stay.  Again, she told me to go play at the neighbor's but not to get dirty.  (She knew that I couldn't not get dirty if I was playing with the next door neighbor boy, Brad Martin.)  I came in an hour and a half later with grass stains on my the knees of my jeans and it looked like I had been in a dust storm -- I was very filthy.

Meryl said, "Oh look at you!!  Let's run you a bath!" She made it a bubble bath and demanded that I disrobe right then so she could treat the stains on my pants.  She told me not to be shy around her because she used to change my diapers and give me baths all the time -- she'd seen me naked dozens of times.  I didn't question her from then on.  As the tub was filling, she said, "Let me rub some of this lotion on you -- it'll get you cleaner and make your skin feel a lot softer."  I didn't know it at the time, but the lotion was actually hair remover.  She had seen Jon and I playing Batman and Robin a few months before, and noticed that we had raided some of Cindy's tights to use with our costumes.  Meryl hadn't said anything, but she didn't like the way the hair on my legs poked out through the tights.  For her plan, she was bound and determined that my body from the neck down would be hair-free.

After waiting nearly 10 minutes before I could get into the bubble bath, Meryl wiped me down with a washcloth then had me soak for a good 45 minutes.  At the end of the bath, she walked in with a large, fluffy, pink towel and dried me off before wrapping it around me.  I was now hairless like she had planned.  She lead me into Cindy's room and said, "Ally, I've got some bad news: Your mother forgot to get your bag of clothes out of the car.  I was going to let you borrow some of Jon's clothes, but they're all too small.  Cindy's will have to do."  I found out later that it was part of the ploy all along -- to "forget" the clothes from the car and to get me dirty right off the bat so I'd be "forced" to bathe.

I was dumbfounded more than anything, not upset at all, and somewhat excited.  After all, as I said at first, I love frilly underwear and dresses.  Aunt Meryl had seen me in various dresses and dance outfits from all of my earlier fashion shows. I just couldn't believe that she was "leading the charge" and actually encouraging me into girls' clothes.  She slipped a pair of white, nylon tricot panties up my legs and into place then said, "Oh, those look so cute on you!"  I couldn't help but notice how heavenly and sensuous they felt -- I was fully erect!  Meryl added, "I know it's only about 6:30, but what if we just get into our jammies right now, enjoy some dessert, and watch some TV 'til bedtime?"  I told her that that would be great.  She pointed to the nightgown on the bed, instructed me to put it and Cindy's bathrobe on, then meet her downstairs.

Aunt Meryl was flipping through the TV Guide when I got down there, and she said, "Would you like milk or juice with your strawberry shortcake?  I answered, "Milk, please," and she said, "There's really nothing on TV tonight - what if we play a few games after I paint my nails?"  I indicated that that would be fine, not really self-conscious at all about the way I was dressed.  She followed that up by asking, "Ally, we need to go get you some clothes tomorrow.  I have a bridal tea to go to on Thursday. followed by the wedding reception of Friday. Jackie, my niece, really wanted Cindy to come with me, but she's obviously not available - would you like to go with me?"  Before I answered her, I wanted to know if there were going to be any other boys there.  When she said, "No, there won't.  I was hoping that you'd be willing to go in Cindy's place, if we can find you a cute dress and some shoes!"

For the second time in just a few minutes, I was so shocked I was speechless.  Meryl felt awkward because of my silence and asked, "Will you please seriously consider it before telling me 'No'?  It would mean a lot to me.  I swear I won't embarrass you, and no one will have to know that you're a boy."  I asked, "What about my hair?!"  She was quick on the draw and immediately, said, "After shopping for dresses and shoes, we'll buy you a nice wig!"  I picked up on what she said and asked, "Dresses?!"  She replied, "You're going to be here for two weeks, Ally, and we can't have you going to both the tea and the reception in the same outfit, can we?"  I take it from your sly grin that you're willing to do it?!"  "Only if you don't embarrass me and if no one finds out I'm a boy." I replied.  Aunt Meryl just beamed at me and was almost as happy as if someone had just told her she had won $10,000.  Before preparing our strawberry shortcake, she added, "No one will know that you don't want knowing, okay?"  "It's a deal", I said.

We enjoyed our dessert, then Aunt Meryl got out her nail polish.  She did her finger and toenails then asked, "Do you want to match me or should I find you a different color?"  I said, "Let's match!" and she complimented me on my choice.  I had always been jealous of my mother and sister being able to wear nail polish; now, here I was, openly wearing some at my aunt's request.  I was really enjoying getting dolled up without being hit or made fun of for doing so.

I had one of the best nights of sleep I ever have that night.  We enjoyed a light breakfast the following morning, then Aunt Meryl found a pretty dress of Cindy's for me which no longer fit her.  The white tights felt great after she helped roll them up my hairless legs.  They were followed by a crisp, white petticoat slip, a lavender party dress, and white patent leather Mary Janes.  She had to dig out an old Easter hat of Cindy's to cover up my short hair though.  After putting on some light blush and some soft, red lipstick, we were ready for our shopping spree!

What an experience that was!  We were both dolled up; walking hand in hand around town.  We must have hit three different clothing stores and a couple of shoe stores and a wig store.  I got some interesting looks and comments because most of the sales ladies knew I wasn't a little girl.  Most were fine with it because they wanted to make the sale, I guess.  I was somewhat embarrassed, but it wasn't as bad as I thought it was going to be.  I trusted my aunt!  In all, I ended up getting three dresses (complete with their own set of petticoats and slips), six pair of tights, two pair of shoes (one in black and one in white leather) and a sandy blonde wig.  Aunt Meryl also got me a couple of training bras, three girls'  tops, six pair of panties (in various colors), some girls' jeans, and a pair of girls' sneakers.

We had an enjoyable few days -- just aunt and niece hanging out together -- then had a great wedding tea for her other niece, Jackie, on Thursday.  I saw and Meryl and Jackie exchange grins and winks after I was formally introduced as "Ally."  Jackie was old and wise enough to know that Meryl didn't have a niece named Ally.  I appreciated her playing along though.  All of the ladies and girls that were there at the tea couldn't have been nicer.  Most were none the wiser, but I learned later that I hadn't been as passable and convincing as I thought.  I guess some of the girls were wondering aloud to their mothers why I wasn't sitting very ladylike at times.  The high school-aged girls figured out that I was a boy, but they didn't make a scene and were actually very complimentary as we were walking out to our cars.  They said things such as, "You look very cute, Ally."  "I love that dress; I wish my brother would be willing to let us do that to him."  "It proves that boys can come to events like this, look nice, and act civilized. -- I'm proud of you!"

I did meet a girl a year older than I (a girl named Natalie who was actually closer to Linda and Cindy's age.)  She had the gall/courage to ask if I was really a boy.  I went beet red, looked at my feet and eek-ed out a small "Yes."  Natalie's mother got the biggest smile, and Natalie just said, "That is so coool!  Will you be at the reception tomorrow?!!"  When I answered, "Yes." again, she asked her mother, "Mom, can we go through the line with Meryl and Ally and, can Ally and I hang out after?!"  Her mother responded, "You bet!"  I was dressed equally as pretty, in one of my new dresses, the next night for the reception.  We had arranged to get to the reception at the same time as Natalie and her mother, and true to her word, we went through the line together.  Jackie and her groom complimented both Natalie and I on how cute we looked and thanked us for getting dresses that coordinated with their wedding colors.

After enjoying refreshments at the reception center with us, Natalie and her mother came over to Meryl's and spent the rest of the evening with us.  It didn't matter to any of them that I was a boy in a dress and they liked the fact that I exhibited no self-consciousness.  I made a great friend in that few weeks and it was two weeks in my life that I will always remember and cherish.  The clothes that were bought for me remained at Aunt Meryl's, hanging in Cindy's closet, but she periodically reminded me that the were actually mine, not Cindy's, and I could wear them any time I wanted (until I outgrew them.)  Years later, Aunt Meryl told me it was a sad day for her when she finally gave the clothes away to Goodwill.  She apparently thought back on those two weeks very fondly, too!

Back to the Top

Return to Sweet Remembrances Page

Return to Petticoat Pond's Main Page