I look out of the window of my room, in a senior citizens' home. It's been so long, since I last left the confines of the estate. As I hobble down dimly-lit hallways, past drably uniformed nurses wheeling residents in and out of their rooms, I let my feet take over. A pair of wrinkled, weary feet, aged from the thrills experienced over the course of a lifetime. Amazing how they still work so well- I barely need my stroller at all. As I find myself walking down the hallways towards the recreational room, where a little sunlight penetrates the otherwise sullen room, giving it a somewhat sombre atmosphere of tranquility. A dozen elderly folks and their loved ones are gathered on various sofas and tables spread out across the room. I take a seat on a wicker chair positioned near the newspaper rack, waiting for no one.

The doors on the other side of the room abruptly burst open, and a family of four walks in, led by a little girl, eight or nine years old at most, with little blonde pigtails and a frilly skirt-blouse outfit, at their head, rushing over to a grizzled old North African campaign veteran parked by the arcade area. 'Happy birthday Grandpapa!' She exclaims, and leaps onto him. He laughs wearily, and ruffles her garish petticoats, exposed from beneath her skirt.

This particular action brought to my attention the events of one summer a long time ago. When you live this long, your summers of carefree boyish fun tend to fuse together, into a blob of memories; it becomes increasingly difficult to distinguish individual events; it all seems so similar. But one summer's events still stand out among the rest; they stand out very much indeed; perhaps because of the lack of 'boyish' summertime fun in it, making them somewhat different to all the other summers I had as a lad.

It was the summer of 1928; I was a typical American lad, perhaps with more longish-blond curly hair than most boys of my age, living with his mother in a small town near Louisville, Kentucky. We lived in a modest two-bedroom detached house, a comfortable middle-class lifestyle we enjoyed. The world was a very different place back then; moving pictures with sound were all the rage, and women with means rushed to get their hair cut short and their wardrobes' hemlines rose to knee-length. My mother was one of those women; despite being a single mother, she was relatively well known and respected in our community for her generosity and charitable personality.

My father I have little knowledge about. My mother never discussed him, and I only know that he left my mother shortly before she discovered she was pregnant with me. My mother's family, an upper-middle class bourgeoisie family from Pennsylvania moved down to Kentucky after the Civil War, had disowned her, as was according to upper class scorn at the time. Being a single mother was hard; nonetheless she moved to a smaller town and we survived as she got a job as seamstress for the first few years of my life. Only when I was five did she find out the truth about my father; that he had signed up to the Army when he ran away from her, and had been killed in Flanders during the closing weeks of the Great War. When I was eight, she learned of her parents' death in an automobile accident; as a result, she received my grandparents' money, and bought our present life.

I started school at a private school in September of that year, 1926. The other children frequently made fun of my girlish, feminine appearance, and would tug at my locks, calling me 'Princess', and other girly monikers. As a result, I often lashed out at them with my fists- I was usually, however overpowered and would end up with my shorts down over the teachers' laps for a spanking in front of my tormentors. My mother, who had quit her job and become increasingly eccentric ever since she had received her parents' money, pulled me out of school in mid-1928, after it became apparent that I was not going to stop my 'reckless misbehaviour'', as a teacher had termed it.

Not only at school, but also outside it I was a little terror. At and around the age of ten boys are usually little terrors, enjoying a phase of hyper-masculinity. I certainly was, and I picked on girls to compensate for my feminine outlook and being teased by boys I saw around the neighbourhood. A favourite trick of mine was to flip their dresses/skirts and/or petticoats up, revealing their panties. This usually resulted in a furious mother dragging me home, to complain to my mother about what I had been up to. I was not spanked at home, however- my mother didn't bother. I was just told to think about what I had done.

However, one day I returned home with my overalls snapped and trousers torn, having challenged a bigger boy down the street named Carl for whistling at me like one would do to a pretty girl, (and lost to his strength), to find my mother in handcuffs. Turns out she had been part of a chain of bootleggers supplying a local speakeasy- Prohibition, the ban on alcohol was still in effect due to the Volstead Act passed in 1919, and a stricter law-enforcer had presumably decided to crack down on bootleggers in our area. I was not told that at my tender age, though, and all I was told was that I would be staying with a neighbourhood family until my mother, whose prestige in our community had been destroyed, had served her time in a local jail (her sentence was six-months), since we had no relatives to speak of in the area.

Imagine my horror when I was dropped off at Miss Perkins' home then! Miss Perkins was a widow, and former schoolteacher, and despite her never having taught me, she had heard stories about my reputation from other mothers in the area. Worse still, her 19 year old daughter Sara had been one of my past 'skirting' victims- she had reacted by chasing me four blocks, until I had hidden behind a corner and lost her. The stern woman looked down at me, and said- 'Well, young man- you certainly need some discipline, and now that you're in my household, that's exactly what you're gonna get!'. I imagined a few months of schoolyard-style spankings and time-outs, but I had no idea of what else awaited in store.

On the morning after my arrival, I awoke in a small crib, in a room decorated a pastel yellow, with lace curtains drawn. This alarmed me, and I jumped out of the crib, and downstairs, bellowing 'Why did you put me-'. I never finished that sentence, for as soon as I made it into the room I was picked up, and deposited over Miss Perkins' lap. I felt the familiar sting of a paddle on my behind and yowled. Only then did I realise I had been stripped of my pyjamas sometime while I had been asleep, and that my bare behind was being tanned. When I was let up after thirty of the best, I covered up my shrivelled manhood with one hand the best I could, as a tried to dab at my tears with my free hand. My pity was interrupted buy the giggling of a female voice, and I looked up to see Sara and another teenage girl, presumably a friend of hers, in the doorway of the living room, blocking any exit. Not that I would have run naked as the day I was born.

'Young man, do you have any idea why you're being treated the way you are?' asked Mrs Perkins. I snivelled in response, and she answered for me. 'Because you are a badly-behaved terror of our neighbourhood, and I intend to set you straight while you are in my jurisdiction. While you are here, you do as I, and my daughter Sara say. Your boys’ clothes have been hidden by us. Is that clear?'.

My buttocks still smarting from the spanking, I tearfully nodded a yes.

'Good.' she replied. 'Since you cannot be trusted to act like a mature young man, I have decided to let you see how the girls you've tormented over the years feel about your... misdeeds towards them.' I was confused; what did she mean? But my confusion soon wafted away, replaced by horrifying realisation as she held up a pair of grey, lace panties.

'No!' I screamed, in a high-pitched voice as I stumbled backwards. 'You-You can't! I'll call the coppers!' I screamed.

Miss Perkins was not deterred. 'Young lady, this is perfectly legal. While I am your legal guardian, you will do as I say. Now put these on.'

Seething with rage at being called a young lady, but not wishing to receive another tanning, I begrudgingly took the girls' undergarment from her hands and slid them up my legs. They felt soft, but so... shameful.

As I was soon to find out, worse was to come. The panties were to be followed by a white cotton, lacey girls' undershirt, a vest. I was then given a pair of white tights, which I slid up my legs, and then a navy-blue pleated skirt, with four buttons on the front panel. This was soon followed by a girls' sailor blouse- the top of a sailor suit. It was long-sleeved, and ended in navy blue, with white stripes around the wrists, and piping around the large collar hanging down the back of my neck, as well as a red neckerchief tied off in a big bow in the front. Black leather Mary Janes, a straw boater, and a blue cardigan finished off my girl's outfit.

A mirror was presently revealed under a cloth, and in it I saw, as I turned, and cried out in despair. A little girl, with curly blonde hair, dressed in a schoolgirl outfit that any girl my age would deem infantile and humiliating. Presently, my rage culminated into a tantrum, and I stamped my foot like a petulant little girl; shouting, ‘I won’t wear this, now take it off and-‘. Once again, i was unable to finish, as Miss Perkins had me over her lap in a second, and she flipped up my skirt and lowered my knickers. My kicking legs, clad in tights and Mary Janes, were held down by Sara rushing over to hold them down, but her mother said, ‘Let her kick, it doesn’t matter much anyhow.’ I screamed with more petulant rage at being called, ‘her’, and received a paddle smashing onto my already-tenderised buttocks.

This spanking continued for some time, and I must have been quite a sight- a screaming little girl being punished over the lap of, for all purposes, her mother, scolding her ‘Bad girl! You will wear whatever I provide, y’hear?’, with her panties around her ankles, a skirt flipped up to expose a crimson pair of buttocks, and blonde curls and my large sailor collar flapping around as I twisted my body and squealed like a helpless infant to escape the pain of my punishment in vain.

Once this episode had concluded, the sobbing young lady was led by the hand to the adjacent lounge, where a gramophone playing ‘Let’s Misbehave’ sat in the corner. How ironic; i thought- that song should be playing now. I was told that we would stay home today- ‘Thank god’, I remember thinking; and for the rest of the summer, I would be dressed as a girl, and expected to act like one. I was taught how to curtsey and walk in a more feminine way. ‘Since your voice is already so naturally girlish’, said Miss Perkins, ‘-I’m sure you’ll fit in perfectly as a girl.’

By the early evening, I was exhausted, and almost thankful to retire to my room. I froze as I saw a new addition to my crib- a top section, almost like a lid, with a lock. Sara followed me into the room, and giggled at the look on my face. We could not have been more different- already she had had her hair bobbed and was wearing trousers like a boy; at the time trousers were considered just barely acceptable for young ladies. ‘It is nice, isn’t it?’ she asked. ‘You’ll be locked in from seven in the afternoon, until nine next morning’. I tried to protest that I couldn’t possibly sleep so long, but the thought of a third spanking to further crush my already beaten masculinity was too much. I was helped into the crib, still in my infantile outfit, and the ‘lid’ was closed. I felt my heart sinking as she locked the top on, then slid the key into her pocket. ‘See you tomorrow, little girl!’. The door clicked shut behind her, and I was left with only my own thoughts in the silence of the crib. I drifted off to sleep hours later, wishing I just had my shorts and overalls again.

The next few weeks were a daze- I was taught to serve tea, and made to do housework around the Perkins household. What made this more demeaning was that I was doing what I had formerly considered ‘women’s work’- this was certainly true in the days of Miss Perkins’ childhood, (she was a firm feminist, and had been an ardent campaigner for the passing of the 19th Amendment (women’s suffrage) a few years prior) but by the 1920s, women were challenging the traditional roles of the fairer sex in society. Girls like Sara went out in the latest fashions- boyish garments, with flat chests and unisex clothes, and came back late after nights of Charleston's and champagne. I, meanwhile, was stuck at home in a frilly blue dress, with short sleeves and petticoats, dusting a mantlepiece, the very image of what would have been expected of Sara back in the Victorian era. I celebrated my 10th birthday at the Perkins’ household, and received things such as bonnets, tights, and even a pair of drawers. The panties I wore (much like those of young women today) were considered indecent then for older girls and women; only acceptable for infants and toddlers, so I was glad to have a pair of ‘big girl’ underwear for once.

By the time school was starting, however, there was no news that my mother would be released from prison any time soon. Mrs Perkins decided to enrol me in a private girls’ school about half an hour’s walk away from her home, where the head was a friend of hers. Her daughter had went there until she had graduated two years ago, and she was delighted that I was to follow in her footsteps. Meanwhile, she left with a suave new boyfriend to New York City- I gazed enviously at the suave young man. How I wished to swap places with him right now! However, when the staff, mistresses and teachers were informed I was actually a boy, they reacted far more mildly than I would expect. In those days, tolerance for cross-dressers was present in cultural centres, owing to the perceived decadence of the Roaring 20’s, but not so much in rural towns like ours, which is why I was so surprised. I was referred to as ‘she’, which now felt far more natural, but still somewhat weird.

The students were far from that, though. Every excess I walked out to shrill cries of ‘Sissy! Girl-boy!‘ and so on. I frequently ended up hiding from my tormentors in dark corners until the bell rang.
I was dressed every morning by my mother in my school uniform- a cotton blouse, then a light grey pinstriped pleated skirt, accompanied by a blue blazer and sometimes a cardigan or tights. Mary Janes, and sometimes my straw boater topped the ensemble off. Every time I wore a skirt, I would feel so exposed and vulnerable. On the walk to school, boys sometimes wolf-whistled and cat-called me- they now knew who I was, and some, such as Carl, took the pleasure of approaching me, and smacking my bottom every so often. My old personality of boyish manliness had almost completely dissipated, and had been replaced by the personality of a simpering, cowering sissy girl’s.

Bottom-smacking, int he form of paddling, was also present at the school. On the fifth week of term, a particularly unpleasant one I received, from pushing a younger girl for calling me ‘Girlboy’. A prefect spotted me, and rather than do justice, she chose to pick me for punishment, making me report to the teacher on duty, who just happened to be a tall man named Mr Harris. He insisted everyone call him ‘Sergeant Harris’, owning to his rank in the war with Spain a few decades ago, and was a well built man, even when he was approaching fifty. It was well known that he enjoyed punishing the girls over his lap, but he had seemed particularly interested in me ever since he had learned of my special secret. So when the prefect lot us alone in his office, I was trembling with fear.

‘Now little girl, do you know why you’re here?’ he said, practically dripping with lust.

I shook my head, looking at him with wide girlish eyes. He grinned and beckoned me onto his lap.

‘You’ve been very naughty.’ He retrieved a paddle from inside a drawer. ‘Now, little girl- or should I say, boy-girl- I’ll offer you a deal.’ He shifted my weight slightly, and I felt through my skirt, a bulge in his trousers. Or was I imagining it? ‘You can take fifty of these;’ he presently whacked the paddle on the table to illustrate his point; ‘or you can let me into your boyhole, if you know what I mean.’ I suddenly felt his hands exploring my buttocks beneath my skirt.

‘I’ll take the paddle, please.’ I quickly said.

‘How disappointing.’ he said cryptically. As usual, I went over his lap, and his paddle whacked down fifty times. But little did I know what was next to come. After he announced ‘fifty’, I climbed down- or at least I tried to. His hands held be still.

‘And now- this I’ll throw in for free.’

His hand held me in place while he undid his trousers, and my muffled cries for the next few minutes were kept silent by one large firm hand over my mouth, while the other held a struggling little body in place on his lap, while his manhood penetrated me from behind. I went home that day, shaken and sobbing. Mrs Perkins spent the whole evening trying to get the truth out of me. Eventually, it all spilled out like milk from a carafe, and I drifted off to a troubled slumber that night, as Mrs Perkins, or ‘Mummy’ as I called her now, shouted angrily over the mounted phone.

The next day, we didn’t see Mr. Harris at school, nor the days after that. The newspapers, had my name in them- everything became public, at least in the local area. People began looking at me in the street incredulously- strangers and classmates alike. The case against Mr. Harris was later dropped- no lawyer had wanted to take our case for me. I’m not quite sure why, but I was forbidden from returning to that school again. Apparently a parent was threatening to sue the school over my presence there, but if there was ever a silver lining here, Mrs Perkins seemed satisfied that I had learnt my lessons, however, and let me back into shorts for the first time in five months. Gradually the looks from people on the street, and the murmurs around me ceased, and I celebrated Christmas as a boy that year, with a new haircut. Everything that had happened those past 5 months we didn’t talk about- Mrs Perkins was simply my temporary guardian, and that was that.

My mother was released from prison on a January morning in 1929. We didn’t speak when we were reunited; she simply embraced me. She had presumably read about what had happened to me in the papers; she knew not to talk about them. When she came to help pick up my belongings from the Perkins’ household, she regarded Mrs. Perkins with some amount of icy hostility.

In a sense, we became pariahs in our community after that experience- my mother because of her time in prison, me because of my cross-gender experience made public (CROSS-DRESSING BOY BUGGERED AT GIRLS’ SCHOOL, read one headline of a local paper.) But, we were together- and that was what mattered. I never saw a single item of girl’s clothing (on my body) again, and never caused another girl distress. But I could never look at some people in my neighbourhood the same way again- Mr Harris, one April morning saw me from across the street. I kept my eyes down, but I am certain he saw me. Mrs. Perkins too- I ran into her at a picture show almost a year after that fateful July day when I had gone over her lap twice in my sailor suit, but she kept her eyes straight, and I averted mine too.

In August 1929 we moved away from that small, backwater Kentucky town, to relieve ourselves of the stigma associated with us. We moved to New York, too a small apartment in Lower Manhattan- a far less comfortable arrangement, but far away from the judging gazes of street vendors, the pity of other mothers, the disgusted looks of Carl and his friends back in Kentucky. Here we were free to start anew.

My mother lost most of the fortune she had inherited investing in the New York stock exchange, which crashed a few months later in October 1929, landing us in a Central park shantytown for my teenage years during the Great Depression- but we were happy in our humble life in new York. And, I was happy too- free of panties forever. But those events, the five months in a series of dresses and skirts, I will never forget, not if I live to be a thousand. No, I could never forget, the events that happened to me, in the summer of nineteen-hundred and twenty eight.

FIN.