How did I end up in the middle of a park holding my underpants up to a camera? Read on...
Sir called me in the morning. “I’ve got a parcel for you, boy. Put on your blue uniform and collect it from your building’s reception.”
My stomach fluttered. I started with the underwear as always: the high-waisted traditional white y-fronts pulled up so the thick waistband sat almost to my belly button, the plain white vest tucked neatly inside, and the pink chastity cage locked firmly in place underneath. Only then did I dress in the rest of the uniform - crisp blue polycotton shirt, navy and light blue striped polyester tie knotted neatly, grey sleeveless jumper, navy blazer with brass buttons, grey wool socks with navy stripes pulled high, black T-bar shoes, and the straw boater waiting in my leather satchel. As I get in the lift, I note how prim and proper I look.
Exiting the lift and avoiding gazes from neighbours, I walk towards reception where an attractive Eastern European man in his forties is manning it. Heart racing, I walked up to the counter, hoping he wouldn’t notice my shorts or buckled shoes. When I asked for the parcel, he handed it over with a warm smile. I couldn’t tell if it was kind, a smirk, or slightly flirty. My cheeks burned as I thanked him and hurried away, stuffing the parcel into my satchel.
Next, Sir sent me to the supermarket for lunch. I felt anxious walking down the street, as people glanced. I found myself repeating the mantra "I'm a good preppy traditional boy" to myself to soothe my nerves. With a deep breath I entered the shop, and bought a sandwich and some fruit, feeling painfully conspicuous. Men around me wore hipster casual clothes, with styled hair and beards, while I stood clean-shaven in my neat school uniform. I paid quickly and headed to the park.
Once there, I texted Sir. He told me to put on my straw boater. I obeyed, blushing harder as I placed it on my head. He asked how I felt. I admitted I felt silly. He jokingly said perhaps it was because was too warm in my jumper.
"Since you're changing outfits, how about a photoshoot". I knew this wasn't merely a suggestion. I set up my camera in the park, ensured not too many people were looking, and snapped away. Blazer on, then off to reveal the jumper, then the jumper removed too, posing in just the blue shirt and tie with the boater still on. Finally, a standing photo with blazer and hat back on, buckle shoes standing out.
After I had sent them, Sir video-called. “Time to open the parcel, boy.”
I sat on the log and opened it eagerly, hoping it might finally be some PE kit so I could wear something more relaxed occasionally. Instead, six crisp pairs of plain white high-waisted y-fronts popped out - traditional, bulky, and embarrassingly childish.
Sir smiled on screen. “Since these are your everyday underpants now, you need more. Hold them up and thank me properly.”
Face flushed deep red, I lifted the packets toward the camera. “Thank you, Sir... for my new y-fronts,” I murmured, voice tight with humiliation. The cage throbbed as I sat there in full uniform, straw boater on my head, displaying my new supply of little-boy underwear in public.
Mercifully it was time to walk home. I had to pass reception again. I kept my head down, avoiding the attractive receptionist’s gaze, cheeks still burning as I hurried past in my neat schoolboy outfit. I could see this was set to become a routine for me, and that as I acclimated the duration and humiliation levels would only get worse.
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