‘Frank, I am very sorry to hear how badly you behaved this morning. You ought to be ashamed of yourself. I intend to punish you severely. Prepare yourself at once,’ I added, getting out the rod. He glanced at it with a look of fear, and a hot flush rose to his cheeks.
He let down his trousers and placed himself in position across the end of the sofa.
I tucked his shirt up and began to apply the rod, and as I was angry with him, I laid on the cuts smartly, raising long, red weals all over the surface of his white bottom. He wriggled, writhed, and rolled about in pain, half turning over on to his side for a moment, so that I saw the front part of his naked body. And what I saw paralysed me with astonishment.‘Frank’ was a girl!
That was the scene that did it for me. Frank & I is one of the great classics of Victorian flagellant erotica. And I read a lot of such stuff. Punishment always turns me on, but in this instance it was the idea of a girl being punished as a boy, by a man who doesn’t know she’s really a girl.
Cross-dressing is a common fetish if you mean men dressing as women. Transvestites describe the joy of wearing soft feminine things, so unlike male clothes. I experience the reverse when I hide my girlish curves in boys’ clothes. It’s strangely erotic, the thick and unflattering cotton Y-fronts and boxer shorts that cover so much more than a flimsy pair of knickers. I feel surprisingly vulnerable, stripped of my feminine wiles and charms. The strict headmaster of my fantasies might take pity on a whimpering girl, but he’s not about to be lenient with a boy.
I’ve done a lot of roleplay as a boy. School canings across my taut schoolboy shorts. Formal 19th century birchings in my Eton tailsuit. ‘Rent boy’ scenes in my Edwardian boy’s suit. (Honestly, before Tipping the Velvet, I had no idea any other girls were into dressing as boys.)
I have some modern clothes too; teen boys’ stuff fits me pretty well. I have to bind my breasts and tuck my hair up under a hat, but I’m reasonably convincing if I don’t have to talk. My boyfriend took me to a strip club in the States once and the low lights helped my disguise. One of the dancers asked if I was gay, but she didn’t suspect I was a girl! Using the gents’ loo was an especially naughty thrill, though I didn’t have the courage to use the urinal. I chickened out and went for the privacy of the stall with the locking door.
Of course, the costume I love best is the one I don’t own (yet). In the days of Nelson’s navy, common seamen were flogged, but midshipmen were bent over a cannon and caned. It’s one of my oldest and most enduring fantasies – a girl who disguises herself as a young gentleman and suffers the wrath of a zealous young lieutenant. I wrote that story, ‘Kissing the Gunner’s Daughter’, for Sex in Uniform, managing to combine three of my fetishes: caning, uniforms and cross-dressing.
I wrote another girl-disguised-as-boy story for Sex and Music called ‘The Apprentice’. And when Nexus Enthusiast commissioned Over the Knee I couldn’t resist another chance to indulge my peculiar kink, this time in a pure spanking arena. But enough teasing; here’s a taste. The narrator, Angie, always wanted to know what it’s like to be punished as a boy. In this scene she’s role-playing a schoolboy who’s got on the wrong side of a bully.
The cane slashed through the air and into my bottom with astonishing force and I couldn’t hold back the breathless cry of pain as my body tried to process the sensation.
The pain began to swell and crest until I thought I couldn’t bear it. I bounced on my heels, trying to will the sting away. My nails gouged into the windowsill and I gritted my teeth, reminding myself that I was a boy.
Boys don’t cry, I thought, desperately needing courage. I repeated it in my head like a mantra.
When he finally stopped, I stood up, stumbling a little.
‘Back in position,’ he ordered. ‘I’m not finished with you yet.’
With a soft moan, I resumed the position.
‘This time you can drop your trousers, boy,’ he said. ‘And your underpants.’
‘You heard me. You’re a cry-baby, Shepherd. And cry-babies are punished on the bare. Now take them down.’
‘Now, boy. I want to see those baby-cheeks. Drop your trousers or I’ll do it for you.’
I blushed so hard my scalp tingled. But I wasn’t about to disobey. With a mournful sigh I bent to the task, unbuckling my belt and unfastening my trousers. I held them up for a moment before letting them slip down to the floor. They puddled around my feet and I stood before him in my boy’s underpants. Putting them on earlier had felt sexy and transgressive, but now I was self-conscious. I knew Peter was thoroughly enjoying my discomfort and I hesitated only another few seconds before hooking my thumbs into the elastic and pushing the cotton underwear down my thighs.
I managed to shuffle my feet away from each other until they were about twelve inches apart. Then I felt the cane tapping against my backside. I winced. I knew he would use it hard. After all, he wasn’t punishing me; he was punishing a boy who had broken the schoolboy code by telling tales. No matter how much you were bullied, no matter what was done to you, you did not squeal. As always, he had set me up nicely.
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