UMD Stories

School Daze
Story by WinterWoollyWetboy
Posted 12/21/22     614 views
Hello wet lookers. This is a story about an unexpected swim at an unexpected time. It was a cold & wet winter day at school. It had been raining heavily all day without let up.
I was having trouble concentrating on my school work because I was starting to formulate a plan to get very wet & getting very excited about it. It involved a swim in full formal winter school uniform complete with shoes & socks. This would be the ultimate forbidden crime indeed. Would I have the courage to go through with it? I figured that my cover story would be that someone had hidden my raincoat & umbrella so I would have to walk home in the rain as I was expected to come straight home without delay to complete my homework. It could actually be the perfect crime because my strict parents were going to be home an hour & a half later on this day due to business commitments.
Today there was to be a slight detour from the usual route. I was going home via the sea baths today.
I was shaking in my seat with anticipation waiting for what seemed like forever for the school bell to ring. I was getting very hard too. Finally this happened & hiding my huge trouser bulge behind my school case. I moved with the herd out of the school grounds & started down the road. Suddenly I veered off on to the track that led to the deserted beach. I crossed the beach & stepped onto the pier that surrounded the sea baths. I was trembling with excitement as I walked down the steps that led down to the water. I stood on the last step wearing my full formal winter school uniform. This consisted of underpants, singlet, long sleeved white dress shirt with striped tie, wool vee necked sweater & a heavy wool blazer. I was wearing a long heavy wool scarf and wool gloves. I had itchy long thick wool & serge blend dark grey winter school dress trousers on with long school socks & black leather school dress shoes. Over the top of all this I was wearing a long grey raincoat. I was also wearing my felt school hat. I stood there for quite a while trying to pluck up the courage to just jump in. I was actually contemplating entering that cold grey choppy water fully clothed. Maybe I was going too far & I shouldn't do it. It would take ages for that thick woollen blazer to dry. Where would I hide it while it took a year to dry? It was so forbidden plus it was so cold looking & I was already freezing cold. I was churned up by an agony of misgivings & indecision. No I'd never get away with it. Could the fact that I almost did it be enough? Maybe I could just get wet by the rain alone. It was no where near as good but that water looks so cold & if I got caught... even getting rain soaked would probably earn me a belting. I'll keep my raincoat on & use my umbrella. My gloves are already soaked & there's a tiny trickle of water wetting my collar & running down the back of my shirt. That'll just have to do. I'll go home have a wank & forget about it. I turned to go & walked halfway back up the steps. I felt such a disappointment however & I realised that It could be a while before I had such an opportunity again. Am I a man or a little grey mouse in full school uniform? Fuck it. Im a man. I walked back down those stairs. I had decided that I was going in exactly as I was dressed removing nothing at all. I stared mesmerised at that cold grey water with the heavy rain pouring down. Nobody would know I'd had a fully clothed swim any way with this soaking rain. The rain had been going all day without stopping once. It might be a while before I get a day like this. It was starting to penetrate my rain coat & run down the inside of my sweater anyway. I could always warm up at home with a hot shower. It was now or never...
I took a deep breath & then I just dived straight in. The cold hit me much harder than I could've imagined & as I shot down I could see dark grey bubbling water. The feeling of my clothes pressing in was fantastic though especially the way my heavy woollen blazer sort of wrapped around me & pressed in on me. I surfaced quickly & noticed that the water was still trickling into my undergarments.This was icy cold but such a turn on. I was bobbing about as if I was wearing a life jacket. That was my blazer gradually aborbing water. Its too late now to go back. I'll make sure that blazer is completely full of sea water like a sponge. As the water penetrated the clothing I sank to my neck & needed to tread water. I realised that I would need to swim furiously to overcome the cold so I swam over arm as if I was doing laps. It was hard work wearing all those layers. I mean think about it. I'm wearing grey woollen dress trousers with a shirt & tie, gloves a felt school hat, a V necked woollen sweater with a thick woollen blazer & a rain coat. I found that school shoes & long grey winter woollen socks are definitely not as good as swim fins. They're just not made for swimming in. Surprisingly I warmed up fairly quickly & it became lovely & comfortable as long as I kept moving. I dived down to the bottom & touched the sand. Oh the feeling of the water pressing in on that thick woollen blazer & all those layers was incredibly sexy. I twisted & turned & played as if it was a summer day & I was wearing swimming briefs. The reality struck me. It was the middle of winter & I was swimming in my full school uniform with socks & shoes, sweater, blazer, tie, scarf, gloves & hat. Up to then despite the cold it was the best feeling ever. I was never allowed to swim & I always had to wear heavy winter Sunday best clothing even in summer. I noticed that my stiff felt hat had become floppy & misshapen but I no longer cared.

After a while I felt my clothes becoming gradually untucked. Soon I was completely untucked. I was never allowed to be untucked. I realised that I could trap air in my trousers & make them balloon up. I also noticed that when I released this air that my heavy grey trousers would press in against my erect manhood. This felt so erotic. I realised that when I swam or performed certain manoeuvres that the trousers would rub against my manhood & excite me. Once I swam overarm really fast & my heavy trousers ended up sliding down to my ankles exposing my white underpants. That was fantastic. I pulled them back up though in case I got caught. I thought about what it would be like to do this swim with a fully clothed girl I liked at school. I did this swimming, naughty thinking a while until I could stand it no more. The trousers were pressing in & rubbing against my toco. My hand were also running up & down the front & seat of my trousers & I experienced a huge long lasting orgasm. I blew into my underpants & trousers & filled them with my custard. It smeared all over my stomach and both thighs. I was in heaven. I just lay back exhausted & floated on my back for a while enjoying the euphoria. Gradually I realised that I would be cutting it fine & I swam back to the beach coming out of the water like a heavily dressed ship wreck victim. As I walked up the beach water cascaded out of my clothing, especially the thick woollen blazer. Those things are definitely not made to swim in.. My blazer & sweater felt so heavy. I looked a mess with everything untucked & my hat completely floppy. I opened my raincoat & blazer to check out how my sweater, shirt collar & tie looked. It looked great. I noticed that the sweater looked longer & was below my arse like a mini skirt.

I showered under the beach shower to remove the salt then headed for home allowing cars to splash me. I hid my rain coat & umbrella & had a hot shower at home.I was so untidy & wild looking. I felt so free. I removed my blazer & inspected myself in the mirror. I removed my sweater but tucked myself neatly back in & adjusted my tie. I noticed that my white shirt was almost transparent. I could clearly see my white singlet underneath it as well as the skin of my arms & shoulders. My trousers had a beautiful shine to them. By this time I was horny again & so I jerked off twice in the shower imagining I was sharing this experience with that girl also in full school uniform. We could be slowly stripping each other until naked. After I had almost pulled my cock out of its socket I sank to the floor & leaned back against the wall with the water running over my transparent white shirt & shiny trousers. My tie was limp like spaghetti. I just chilled out completely & swigged some wine from a bottle I'd stolen. This was the best feeling ever.
I was still trying to dry my clothing when my parents returned home. I was questioned about my still damp clothing but I thought I had managed to convince them that it was due to the rain. The only problem was that the local shop keeper & busybody saw a kid swimming fully clothed in full formal winter school uniform. I was in the shit. I crumbled under questioning & confessed to everything. I was also in trouble for lying to my parents. They gave me a belting & a lecture & grounded me for ages. No big deal because whenever my parents are home I had to come straight home & do my homework anyway.

Years later I was still being asked why I did it. This just adds to the forbidden nature of it all & so I stayed home afternoons & making the best of early nights I masturbated into my underpants & long flannelet winter pyjamas for two weeks running. How good is that for a punishment. It was still worth it. Heres a few pictures of me swimming in my office clothing one lunchtime. It was a similar forbidden swim with shoes & socks too. It was a hot day so I was able to go back to work almost dry after my swim. The shoes & socks were a bit damp though.
Cheers, Winter Woolly Wetboy.
Comments:
washme01:
3/26/25
  Report
Great story.
WinterWoollyWetboy:
3/27/25
  Report
Thanks Washme a great day indeed
WinterWoollyWetboy's blog & storiesFollow storyAll stories
Share this on TwitterShare this on FacebookShare this on Reddit


Design & Code ©1998-2025 Loverbuns, LLC 18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement Epoch Billing Support Log In