Kept in Blazers

Sir decided that a bolder colour tie and socks would help keep you out of mischief.

A recent trip to get my hair cut, dressed like a good boy. I felt relieved compared to my last time in full uniform, although still a little silly, especially when the guy before me was in a tracksuit getting a high fade. In contrast, I sat down with my velcro shoes poking out under the gown and asked for my usual side parting 🫣.

Also, introducing my new casual coat - from a schoolwear brand. It should keep me smart and subtly embarrassed on outings. The arms are a little short but it reminds me I'm just an oversized schoolboy 😅.

Not been in uniform as much recently, but I did have a uniformed outing to meet with a good friend who is also ASB. We went to a restaurant in our uniforms and ate in our school blazers!

Last night was another one of my regular trips to the monthly spanking event in a local gay bar. I’ve been doing this for months now - wearing my full school uniform on the journey too - and the mixture of thrill and vulnerability never quite fades.

This time I wore my purple uniform. I started, as always, by pulling up my high-waisted white y-fronts nice and snug to my belly button, tucking in my white vest. Then came the plain grey shorts (worn high on the waist as usual), plain grey knee socks pulled straight and neat, my crisp purple blazer and matching tie, sleeveless jumper, and finally my brown T-bar shoes.

Standing in front of the mirror, I felt that familiar rush. An adult man dressed like a proper old-fashioned schoolboy - the high shorts, the formal blazer, and those distinctly childish T-bars still make me feel so small and prissy.

I stepped into the lift feeling excited, took a couple of photos of myself, and then unexpectedly the lift stopped halfway down. To my horror, an acquaintance from the building got in. My face instantly burned. I’d briefly wondered about dashing out and taking the stairs, but now I was stuck. He looked me up and down, said hello, and asked how I was without commenting on my outfit. We quickly realised we were both heading towards the same street in town. He was meeting friends at a nearby bar, while I was off to my kink event. That meant we’d be walking together.

The fantasy of being seen in uniform instantly turned into a very real, very exposing experience. I felt incredibly self-conscious next to him in his casual clothes. I tried to keep the conversation flowing naturally, though at one point I offered him an easy out, saying he didn’t have to walk with someone dressed so unusually. He smiled and asked if I was the one feeling nervous. I admitted I was a bit embarrassed but said I was okay, and we carried on. By the time we reached the gay area the initial panic had eased a tiny bit. I still felt silly and conspicuous, but it was starting to feel almost normal.

The event itself was lovely. Being in uniform in a space where it’s understood felt comforting after the public walk. There were only a couple of others in school gear, but I felt far less exposed than outside. I spent a wonderful four hours meeting folk, including moments with my shorts and white briefs down around my ankles, getting thoroughly spanked by the headmaster and several other gentlemen.

On the way home I stopped in the main gay area for a few photos while people walked past. Then I bumped into another acquaintance heading into the village. I explained I was on my way back from a kink event, cheeks flushing again. Shortly after, one of my best friends texted saying he was out in the area for karaoke and asked if I wanted to join. I told him I was still dressed in full uniform and felt far too self-conscious to join him in a regular bar. He joked that we could always sing something from Matilda the Musical if I changed my mind. Part of me really wanted to see him, but the embarrassment won out.

Just two blocks from home I ran into more friends - including someone new I rather fancied - which brought the self-conscious feeling rushing back. There I was in my school uniform at 11pm, heading to bed while they were all off having a night out. Once inside I took a final photo of the marks on my bottom for the headmaster, changed into my pyjamas, and slipped into bed feeling sore, belittled, and humble. This was the most unintentional exposure with people I knew I'd ever had in uniform.

I tried a softer approach for my regular café visit. Instead of full school uniform, I went with a smart blue shirt, knitted tie, short khaki shorts, knee-length navy socks, and shiny black shoes. It felt like a safe middle ground - boyish enough to satisfy that thrill, but not so obvious that the regulars would stare... or so I thought.

I went to the park first to take a couple of photos. One dog walker there who had seen me before saw me trying to discreetly pose for a timer photo and said " that's a really nice outfit", which made me blush!

The café owner took one look at me and smiled. “Those shorts and socks are great! You look very schoolboy-like today.” My face instantly went red. My clever “not too obvious” plan had completely backfired in the best possible way. There I was, sitting among people who know me, dressed like a proper, neat schoolboy should.

It was equal parts embarrassing and exciting. Maybe I don’t need the full uniform every time. There’s something addictive about these smart, slightly childish outfits that still let me feel exposed and boyish in everyday social settings.

Good boys keep their:

- socks gartered

- shoes polished

-collar fastened

- shorts short

- snake belt fastened

- shirt tucked in

- tie tight

- jumper embarrassingly bold

Even for simple errands.

Throwback to trying on my duffel coat for the first time last winter. It's warm and comfortable, but stops just above my knees, giving no respite to my bare kneecaps and making sure bold striped socks are on show to the world.

As a "reward" for getting my haircut, I went into McDonalds on the way home in uniform. Sadly they don't do a vegetarian Happy Meal any more, But I got some chips and sat eating them with some bemused onlookers.

Haircut in Full School Uniform

I’m sitting here in the barber’s waiting area right now, heart hammering, trying to focus on my breathing. My navy blazer is hung up on the peg, leaving me in just my crisp white school shirt, stripey tie, and grey shorts. My long knee socks are pulled up tight and my smart black shoes gleam under the lights. I feel so exposed. Every time someone walks past, I swear they’re staring. Deep breath in… deep breath out. This is both the most thrilling and most terrifying thing I’ve done in ages.

---

This morning I woke up and decided: today’s the day. A big step in public confidence. I was going to get a traditional smart haircut while in full uniform.

I started getting ready with that familiar flutter of excitement in my stomach. First the polycotton white shirt. Then the stripy school tie, knotted carefully. Next came the grey shorts – pulling them up always makes me feel instantly younger and more vulnerable. Long knee socks, pulled up to just below my knees, and finally my shiny black shoes. Last of all, the navy blazer with its shiny brass buttons. I stood in front of the mirror and just stared. I looked so properly, unmistakably like a schoolboy. Neat, prim, and embarrassingly childish. My cheeks burned, but god, it felt amazing. That rush of putting on the uniform is addictive.

I grabbed my bag, stepped out the door, and took the lift down. Before leaving the building I snapped a quick mirror selfie - long, scruffy hair still wild, contrasting sharply with my smart uniform. Then I started the walk to the barber’s.

Every step felt electric. Halfway there I heard some workmen laughing behind me and my stomach dropped. Were they laughing at me? A minute later an American couple waiting for a taxi muttered something about “school uniform” as I passed. My face went bright red and I kept my eyes fixed forward, pulse racing. I had warm bolder uniforms in public before, but this wasn’t a quick supermarket dash or a hidden park photoshoot. This was a real appointment I couldn't easily get out of.

I arrived a little early so I sat on a bench in the nearby park, knees together, blazer buttoned, trying to look casual while dressed like this. When the time came, there was no turning back.

I walked in, greeted the barber with a shy “hello,” and sat on the bench. Then came the moment I dreaded: I had to take my blazer off. Suddenly I was just a boy in shirt, tie and shorts. When it was my turn, I climbed into the chair. The barber draped the gown over me, but it was a bit awkward because of the tie and collar. I felt a wave of relief as the gown covered most of my uniform… at least for a while.

I asked for a side parting. The cut itself was mercifully quiet - no comments about my outfit. I watched in the mirror as my messy mop transformed into a crisp, neat side parting, short back and sides. It looked so perfectly schoolboy.

Then I had to lean forward into the sink for the wash. That’s when the back of my grey shorts rode up slightly, elastic waistband on show, my hands resting on my bare knees. Another rush of humiliation hit me hard.

Finally it was over. The gown came off and there I was – a proper, pristine schoolboy with freshly combed hair. I paid, embarrassed, and as I put my blazer back on, one of the other barbers smiled and said I looked like the old-fashioned gentlemen in the pictures on the wall! I mumbled a thank you and stepped outside.

Walking home I felt a strange mix: deep, burning embarrassment… but also real pride. I did it. I sat there for half an hour in full uniform and survived. It was scary, humiliating, and incredibly exciting all at once. I know this will make wearing my schoolboy clothes in public so much easier next time.

Would you believe I actually enjoyed it? The thrill of being seen like this is addictive… even when it makes me want to hide forever.

What do you think – should I push myself even further next time?

Today was a quick trip to the shops for lunch in a loud red blazer. I felt butterflies in my stomach and a straining in my white briefs as I pulled my shorts on, tightened my tie and fastened all the buttons on my blazer. The buckle shoes always give me a mixture of joy and embarrassment.

I walked outside in my blazing red blazer. It's strange how something that I would have felt terrified to do several weeks ago has become enjoyable. I used to just get excited before and after my schoolboy outings, and mostly nervous during. But today I felt the thrill of being dressed in my smart uniform for the whole journey.

I didn't even hesitate this time walking into the shop and picking out my food. The nerves are still there. I did use the self-checkout rather than a cashier though, and when I spotted a handsome gay acquaintance I avoided bumping into him, but I'm slowly getting braver about letting people see my adult schoolboy side. After all, I feel cute and happy when I'm dressed like this.

With my lunch in hand, I headed to the park to feed the ducks and snap a few photos in my boyish outfit. I wonder what the goose made of me!

I find myself wanting to push my comfort zones even further, getting used to being dressed as a smart school boy for errands. Wearing louder and more distinctive uniforms and smart childish outfits.

Back in January I took one of my biggest steps into dressing properly like a traditional boy when not in full uniform.

I put on brown smart shorts, grey knee socks pulled up straight, shiny black T-bar buckle shoes, a crisp white shirt and tie, a thick patterned sleeveless knitted jumper, and my tweed jacket. The shorts left my knees exposed to the cold air, but the heavy tweed jacket made everything feel wonderfully old-fashioned.

It was exciting from the moment I stepped outside. My bare knees looked so childish next to the smart tweed (which was actually a blazer made for a rural English school), and I could feel myself gently regressing into a proper traditional boy doing innocent everyday things. The cool air on my legs and the slightly restrictive feel of the outfit made me blush, but deep down it felt right.

Initially very nervous, I went to feed the geese and ducks in a pond. Their innocent interest made me forget the embarrassment of being a grown man dressed like this. Instead, I slipped deeper into the headspace of a good boy just out doing simple, harmless activities.

It was one of those days that reminded me why I love dressing this way.

An apple for the teacher 🎓

I've always loved the look of cloth nappies and plastic pants under a school uniform.

I had to pick up a parcel, grab some lunch, and buy fabric to line my new wool school shorts. The cold air bit sharply at my bare knees as I walked, making the shortness of the uniform feel even more exposing with every step. People kept giving me stares, some discreet, others not so much.

Lunch in the supermarket was embarrassing enough — there was a big queue at the self-checkouts with a young, athletic staff member helping customers. Thankfully my transaction went through without needing any assistance.

The fabric shop was by far the most nerve-wracking. The odds of bumping into someone I knew were pretty high, and I had to ask an assistant to cut me a metre of cotton while trying to ignore the curious glances.

On the way home, things got even more humiliating. As I walked down the road, someone suddenly shouted something in French at me from the other side. (I think it might have been garçon, or un question?) I turned around to see a man in his 40s looking straight at me with a big smile. He gave me a thumbs-up. Instinctively, I smiled back and returned the thumbs-up. It was oddly encouraging - a little boost, even - but it also drove home just how much my outfit was drawing attention.

Once home I picked up my parcel. The receptionist now knows me by name, so I tried my best to chat about the weather to distract from how I was dressed.

My parcel? A new razor, to keep my chin boyishly smooth.

I suppose I’ll get used to all of this… eventually.

How did I end up in the middle of a park holding my underpants up to a camera? Read on...

A Parcel from Sir

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.