For the next few weeks, playing “Dress-up” was all we did. It was a drug for me. It was my heroin. She’d go through the box, while I’d go through her closet. I hadn’t let her put makeup on me yet, but she sometimes put on some that her mom set aside for that very use. Somewhere along the line my lack of modesty must have rubbed off on her because she’d stopped asking me to turn around when she changed. It was at that point that I discovered girls also had more variety when it came to underwear as well. Theirs came in colors other than white, and had a thinner band at the waist. Plus it lacked the weird flap in front — a flap which I could never master.
It took a lot of nerve, but one time I asked if I could wear a pair of her underwear. She got a pair of white panties with little pink hearts from her drawer, and handed them to me. I reached under the skirt she’d leant me, removed my undies and put on hers. I don’t know if she saw my privates, but if she did she wasn’t weird about it. We were just kids playing after all. Innocence was not yet lost.
The fabric was thinner, softer, more comfortable. I kicked my “Fruit of the Looms” across the room. If putting on her dress made me feel free, wearing her panties was akin to paradise. I felt… right somehow. I would dread putting on my own underwear when it came time to go home. I don’t know if she read my mind, but she told me that she didn’t wear those panties anymore, and I could keep them. I’d have to keep them hidden from my mom, of course, and I wasn’t sure how to do that yet, but I thanked her, and wore them home under my own.
Spring had arrived by now, and the weather was warm and sunny. I felt odd in my own clothes now, even at school. April had grown weary of playing “Dress-up” and was ready get back to her swing set. I suggested that we compromise. We’d run and play as we used to, but I’d get to wear her clothes. If being in her clothes was freedom mixed with paradise, being outside in them was infinitely beyond any bliss Heaven could have offered. I rejoiced in the feeling of the breeze playing through the fabric of her pink sun dress. By now, I was also wearing her tights and shoes regularly. Boys don’t get tights of any kind, and I wondered why. Shoes… well, the difference was familiar: girls got more variety all around. April said I looked “so cute” in her clothes.
I was so incredibly free. I knew what I was doing was “wrong” (Mom’s programming saw to that) but I didn’t care. It felt so good. It felt so right. The breeze was playing back with me as I swung and ran and twirled. I wanted to go everywhere. I was confident. I was whole somehow. I wanted to mention all of this to April, but I didn’t. On this day I had to rush to put my own clothes back on when I noticed the time. My mom would be home in the next few minutes. Mom always spoiled my fun. I was unlocking the door when my mom pulled in.
On the last day of school, we had a half day. This was the day April convinced me to let her put makeup on me for the first time. Seeing as how we had six hours instead of two and a half, it seemed okay. Little did I know, my mom would leave work two hours early.
I was loving the outfit April picked for me: a lavender blouse with ruffles on the front, a black skirt, white tights and shiny black shoes with a silver buckle and a strap which slung around the heel. April had put some silvery-blue eye shadow on me, a bit of bright pink blush and pink lipstick. We were just about to go outside to play when an ominous knock rattled the door. April answered it, and as fate would have it, my mom stepped in, calling my name. I had no time to change back. I wasn’t even in the same room with my clothes. If I tried to get them, Mom would see me anyway. I thought my heart was going to explode. I rounded the corner.
“What in GOD’S name are you doing dressed like that?!?” she nearly screamed.
April tried to defend me. “We’re just playing,” she said. “I dared him to let me dress him up.” This was partly true, but everything cascaded downhill from there. Forced to change into something “normal”, I was scolded the entire time I was getting “that shit off” my face. April was chastised too, my mother calling her a “bad influence” and forbidding April to ever play with me again. And that was just the beginning.
You’d think I had just caused the downfall of civilization the way Mom carried on. I started crying when she threw me on my bed and slammed the door. She called April’s mom at her work, ranting and raving about the whole ugly scenario — questioned her fitness as a parent, and proceeded to pretend the house next door to us wasn’t even there. She told my dad too. He almost took it in stride, until Mom asked why he didn’t seem upset that his only son was behaving like a “fucking queer in the Castro” (whatever that meant). Then Dad did what dads do: I got a spanking. Both my parents REALLY lost it when my pants were pulled down and they saw those little pink hearts. I can’t recall anything else that happened that day.
I was grounded for the Summer. I couldn’t even go in my own back yard. (I might talk to April through the fence.) My parents enforced this by each of them calling five or six times a day at random intervals. And God help me if I didn’t pick the phone up by the third ring. Sometimes one of them would even take a long lunch and come home to check on me. I was miserable.
Near the end of the Summer, I noticed a moving van at April’s house. I wasn’t even going to see her at school next year. Now, I was really depressed. I had just gotten off the phone with Dad when the door bell rang. I answered it. April was there, holding a paper bag. She’d come at three thirty, well away from any chance of being caught by my parents. My heart was still skipping though.
“My mom thinks it’s stupid how your parents reacted. She told me that if I wanted to say goodbye, I should,” she said. I was petrified. Relieved, but petrified. I didn’t know what to say. “I went shopping for school clothes yesterday, and I have something for you. From my mom and me.” She handed me the bag. Of course, I took it. My parents had blown everything out of proportion. The punishment certainly didn’t fit the crime. They took away my Summer, and took away my friend. Not only that, but they even sacrificed friends of their own just because I wore girls’ clothes once (as far as they knew). I invited April in, and opened the bag.
A lavender sun dress was folded up on top. It had a violet swirl pattern on it. Beneath that was three pairs of panties -one white with pink flowers, one almost matching the color of the dress, and one pink with white lace around the waist and leg bands- a pair of white tights, and shiny black slip-on shoes with a small heel. Also in the bag was baby-blue eye shadow and pink lip gloss that tasted like watermelons. I couldn’t keep myself from trying the clothes on right then. (I skipped the makeup.) All the clothes were a little loose-fitting, but her mom wanted me to be able to enjoy the clothes as long as possible. I had the perfect place to hide them too: in some shoe boxes slid WAY under the bed.
I hugged April. She wrapped her arms around my shoulders (now free from sleeves for the first time in months) looked me in the eyes and said: “You look beautiful. Your mom can’t take that fact away.” Before I could weep at the beauty of her words, she kissed me. On the lips. It was a quick and innocent peck, but it was my First Kiss. And here I was wearing panties, tights and a dress, looking “beautiful”. I kissed her back in kind, and thanked her (and her mom) for the clothes.
I wore them whenever possible, and even taught myself how to use the laundry facilities so I could keep them clean. I was never caught again, and after about two years, I grew out of the clothes. I disposed of them by putting them in a bag and then sneaking them into a neighbor’s garbage can.
To this very day, I still don’t understand why being myself was so wrong.