PRESTON, a 12-year-old bully, petticoated out of his evil ways, the sequel

A Little Experiment

             It was Friday afternoon and I had just come in from soccer practice. Thelma (my stepmother), and the Sandfords, placed shopping bags on the floor and she explained the dress code. I knew this had been coming ever since word spread about how perfectly I had behaved for a week after the birthday party where I’d spent the whole time dressed as a girl, as punishment. I still had a few behavioral issues at school that needed work, and this terrifying solution had been found. 

            “When you are being disciplined—that will be every day after school—you will wear only dresses and girls' socks and shoes. Your bedroom will be locked to keep your regular clothes closet off-limits.” 

            “How about completing the look with a wig and makeup?” asked Mrs. Sandford, winking at me. “Poor Preston looked awfully awkward at Sally’s party, in his pretty dress and his short haircut. You could tell a mile away he was a boy in a dress. He’d make a darling girl if we went all the way.” 

            “That’s just the thing,” said Thelma. “Preston is just too good looking. He’s a pretty boy. If he passes as a girl, no one will look at him twice. What lesson will he learn from that? No, he has to look like a boy in a dress, so he looks and feels just a little silly, and really gets some attention! If we need to take him out in public, anyone who’s curious will have to get a close look and ask him what’s going on. And Preston will have to explain why such a clean-cut boy must wear such pretty girly-girl clothes.” 

           Translation: they didn’t want me to look like a girl, they wanted me to look girl-like: sissified, humiliated, awkward, and ridiculous, I thought. 

These were the rules: I would come home from school every day and immediately undress. A new set of clothes would be laid out for me. I would have to do all my chores and homework in girl clothes, and when I reported that everything was done, my room would be unlocked and I could put on pants again. If I failed to finish the chores or homework, I would be kept in a dress until everything was done. If I wanted to watch television in the living room before my homework was done, it would be in a dress—risking being seen by any and all visitors. These were all incentives to do my chores and homework very promptly, and correctly—which I had always been terrible at. 

 I was told that this—unlike what happened to me at the birthday party—was not petticoat punishment, because I had not yet done anything to be punished for. This was petticoat discipline, to keep me in line. 

           “Because we don’t think you’ll be tearing around town, teasing girls and starting fights with boys, if you are dressed like a girl. In fact, I think you won’t want to leave the house at all!” 

           That was for sure.           

            “You’ll behave much more nicely and some of your boyish instincts will be tamed. You’ll study hard and get your homework done. And you’ll look so sweet!” 

            “Starting when?

            “Starting now, of course. Take off your clothes.” 

            Oh heck. And in front of all of them?? This was so unfair. They just said I hadn’t done anything to be punished for! I thought I’d have a shot at arguing out of it, hoping that the combination of my good looks and pleading would make the case. (I had always gotten away with a lot, thanks to being such a cute boy.) 

            “Please don’t—please! Anything but this. I don’t want to be a girl. I’m a boy. Can’t you give me any kind of discipline where I can keep my pants? Anything at all!” Real tears came into my eyes as I remembered the humiliation of being chased around the Sandfords yard by screeching girls, laughing and lifting up my dress. “If I get into trouble you can make me dress up like this, but until then, can’t I have another chance?” I was sure my begging would make them sympathetic. 

            “This boy just doesn’t listen,” said Mr. Sandford. “Shall I do the honors, ladies?” 

            “We’ll all help!” laughed his wife, clutching my wrists. Thelma started unbuttoning my shirt. Mr. Sandford went straight for my belt, and in seconds my pants were unbuckled, unbuttoned, unzipped, and around my knees. I tried to struggle, but in no time I was standing there in just my white Jockey briefs. 

            “He won’t be needing these,” said Mrs. Sandford, gathering up my clothes. 

            I was almost sobbing as I was given white knee socks and white patent leather shoes to put on. Next, and more horrible, was a short white lace petticoat skirt with layers of ruffles and little pink bows all around the hem. Most horrible of all, it did nothing to hide my undies, which were totally visible through the lace. And I was bare from the waist up! I was almost relieved when Thelma produced a dress from a shopping bag. But not relieved for long – it was just as frilly as the party dress I’d already worn, white and very short, and instead of puffy little sleeves, it was sleeveless. It was pulled over my head and Mrs. Sandford zipped up the back. There I was, sissified again. 

            “How do you feel, Preston?” asked Mrs. Sandford. 

            “I feel like I’m being punished,” I said, tears welling up again. “I feel like a sissy!” 

            “You sure look like a sissy boy,” said Mr. Sandford. “That’s the whole point. Do you feel like going out and bullying someone now? I didn’t think so! No more pants for Pretty Princess Preston!” he chuckled. I blushed and my ears turned hot. 

            “You’d better get started on your homework,” Thelma said. “Otherwise you’ll be spending hours getting used to your pretty new girl things. But maybe that’s what you need!” 

            I have to admit, they had my number. They knew that petticoating me was effective at killing my boy ego. They even knew that, like many boys, I lived in fear of being seen in my underwear, even of other boys seeing the waistband of my briefs. That was why the dresses were so indecently short. They knew I was naturally modest – that is why they liked keeping me bare-legged, bare-armed, and gosh, this sleeveless dress even kept my shoulders bare! I felt not only girlishly humiliated, but naked too, and so completely helpless. 

            The women started putting away the other shopping bags. As I headed down to the rec room where my schoolbooks were, Mr. Sandford patted my crew cut and then gave me a pat on the butt—to be exact, on the seat of my near-exposed underpants. A pang of shame and embarrassment ran through me. He put his lips next to my ear: “Hey, Sissy!” Gosh, that man hated me.

A Trip to the Library 

            That went on for a couple of weeks and the forced-feminization regime remained pretty discreet. I always had this heavy-hearted feeling coming home from school or ball practice, dreading what feminine little frock awaited me at home. I had even come to envy the girls at school, in their long-sleeved blouses, sweaters, knee-length wrap-around kilts, and so on. Those girls’ clothes were so conservative and staid compared to the frilly dresses I was forced to wear every single day!  

Even on Saturdays, my homework and other duties had to be finished before I could shed my dress and get on with my day. Ironically, that often meant going over to Eddie’s, where I would again be undressed and petticoated. He loved to hide my clothes and play with me in just my undies and his sister’s petticoats, and even made me wear pink panties sometimes, which made him hoot with laughter. He did keep his part of the bargain – he never showed anyone his photos of me from the party, and never told anyone about my predicament there. This had a price of course. No longer happy with just kissing me and having me kiss him back, he would shed his own pants and make me put my hands inside his underpants. Boy, did I ever resist that, but he was the boss. He even got me to blow him, which no boy wants to do, let alone kneeling in panties and petticoats! While I was doing it, he loved to make comments like, “You suck a mean cock in your Jockey shorts, Preston, because I know you’re motivated to get your darn pants back. But pink nylon panties really bring out the fairy in you!” So let’s just drop Eddie for now. 

            I have to say that being confined to the house in my frilly dresses got kind of restful. Outside, I had to be the tough guy, and compete, and be on my guard. Stuck in the sissy world allowed me to let go of all that. I still felt humiliated, but (and I would never have admitted this to anyone!) I started to see myself differently. I was no longer near tears when I stepped out of my pants and put on a petticoat instead. As long as it was a secret world indoors, I was starting to adapt to the petticoat discipline. Then came that awful day when I had to leave the house. 

            It was a rainy afternoon, and I was hours away from finishing my homework, when I noticed that my book report book was overdue. I absolutely had to renew it, but the library would close at five.  I had to go now. I explained this to Thelma and asked her if there might be an exception to this rule just this once … could I please, please, please put on my boy clothes to run to the library? I promised to get back into the dress the minute I got back. 

            “Nonsense, Preston. This is a perfect chance for you to show off a little. It’s a rainy day, so you’ll need your raincoat and umbrella. Very few people will be out. You will get a nice little taste of being a girlie boy right out in public.” 

            She knew as well as I did that the library was often crowded on rainy days. My secret would be out. Five minutes later I was trudging down the street in my yellow slicker, my bare legs and hem of the dress plainly visible. I was terrified. 

            Bobby Hill was at the counter of the half-full branch library. He didn’t see me come in, and I got so close to the counter that he could not see my girly shoes or bare legs. He was getting ready to stamp the book and said, “That’s a dollar fine, Preston, and I have to see your library card.” 

            Oh no! My wallet was in the inside pocket of my slicker. I would have to unzip it. I tried to turn away as I did this, but he saw anyway—he saw the pale pink dress with the Peter Pan collar. His eyes got very wide. 

            “What the heck, man? What are you wearing? Is that a dress?” 

            “I lost a bet,” I lied. 

            He hurried off his chair and came from around the counter to gape at me. He whispered loudly, “You have no pants on, Preston! What gives? What are you doing??” 

            “Can we discuss this in back?” I pleaded. He led me to the back office, and on the way, the men reading newspapers in the periodicals section stared suspiciously at my bare legs and the pink hem.           

            “Take off your coat! I gotta see this.” His eyes were as wide as saucers now. “Holy cow, it’s true!  What happened to your pants? Where are they? What are you wearing underneath?” 

            The typical dumb boy questions. Why did it matter?, he explained. 

            “I’ve worn a dress once, when my mom was altering a dress for my twin sister, but I had all my clothes on underneath. When Archie Dunlop was a gypsy girl for Halloween, he wore a dress, but with a pair of summer shorts on underneath. That all makes it just pretend. But if you’re dressed like a girl with just your undies on underneath, that’s the real thing—it means you’re really dressed up like a girl.“ 

            He whistled when he saw my briefs. I begged him not to tell anyone. 

            “Well, I guess … No, wait a minute. Let me tell Kevin Moore.”           

            I always used to torment Bobby’s next-door neighbor, Kevin Moore, in the schoolyard, and once I had de-pants-ed him for calling me a stupid rich kid. At the time, I really enjoyed knocking him over and pulling his jeans down to his ankles while the other kids laughed at his embarrassment. 

            “After all, Preston, you de-pants-ed him in public and everyone still teases him about it. If I tell him you lost a bet and you had to come to the library in just your underwear and a pink dress, he’ll feel a lot better.” 

            In the old days, I would have socked Bobby in the nose  for even suggesting this, but things had changed … on top of being sissified, I had lost all my leverage. Now I had to submit and settle things peacefully on other people’s terms. I said, “OK.”  Before I put the slicker back on to hurry out, Bobby insisted on coming close to reach under the dress and feel the lacy petticoats. He put both his hands underneath and felt them from behind, too, and I began to wonder if I had another Eddie to worry about. But he stepped back and said, “You better leave by the back door. There’s a line at the counter now, and you don’t want all those high school girls seeing you like this, do you? Or maybe you do!” He winked. 

            I left, running, and thinking … Now Eddie, Bobby, and Archie would all know about my petticoat life. How long would it be until the whole school knew?? 

A second, and final sequel


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