UMD Stories

The big boating fail.
Story by WinterWoollyWetboy
Posted 1/4/23     232 views
This is a story about what can happen if you go out boating without permission. Years ago when I was in high school there was an old row boat tied up to the swimming bath jetty. Nobody knew who owned it or where it had come from. We all had thoughts about claiming it for ourselves but we had been told by the adults that it was strictly off limits & we were to go nowhere near it.

I had been in trouble for swimming fully clothed recently in my full formal winter school uniform & was still grounded meaning that I had to go straight home after school & change into my pyjamas after eating dinner & completing home work as well as household chores. I wasn't game to go out boating just yet.
A few of the more adventurous boys that were luckily from the swimming team hatched a plan to sneak out at lunch time & row this boat around to the next small bay & hide it there. They thought that they could achieve this & sneak back to school before the lunch break ended. I was envious but decided that I couldn't afford to get involved with this plan. When asked if I wanted to be a part of it I politely declined the offer. I felt a sense of regret but I resisted temptation & kept clear. When the lunch break came around however I couldn't resist following & watching from the beach. The boys snuck over & cut the boat free. They used some small plastic oars from a kids toy boat to row off in this run down little old row boat. There were five boys aboard a boat that probably shouldn't have had more than two or three people in it. There wasn't much free board. Added to this was the fact that it was in the middle of winter. The water was a bit choppy & it was windy as well as snowing. The boys were wearing full formal winter school uniforms including sweaters, blazers, woollen scarves & gloves as well as their socks & shoes & school hats. Some had school raincoats on as well. Some of the fools had even brought their school bags. This made the little boat very overloaded. After arguing about who was to sit where they settled down & cast off. They had to work hard to make any headway but managed to finally get away from the pier. I became concerned & ran onto the pier telling them that I didn't think it was safe. They hurled insults at me & told me to mind my own business. I gave up as they got near the more exposed water. They stopped making head way against the wind & the harder they paddled the more they splashed each other. They started arguing furiously as the wind threw the spray up over themselves. Seeing them getting slowly wetter was a bit of a turn on so I continued to watch. They were too far out now to communicate properly with by now but I could catch the odd sentence. One rather large fat kid was criticising the front paddlers efforts. I think he wanted to take over & change places. The others seemed to be pointing out why this wasn't a good idea. I suddenly heard a man's voice shouting angrily from the track leading to the beach. It was one of the teachers. Old Mr Horan. He was our maths teacher as well as the coach of the swimming team. I was filled with fear. but I had the presence of mind to hide behind a large rock. Mr Horan ran puffing & blowing onto the pier shouting angrily to the boys to return immediately. They tried to turn the boat around unsuccessfully still arguing furiously. The big fat boy decided to take matters into his own hands & started trying to climb over the others to get to the front & take over the oars. I heard the other boys screaming at him to sit down but he didn't listen. As he stood up the boat rocked furiously & a wave came over the side almost completely filling the boat. The bow dipped under the water & the boat filled up completely. I saw the boys getting lower & lower into the water until they were sitting waist deep in water. One of them was trying unsuccessfully to bail it out with a small bucket. Suddenly the fat boy fell through the floor & it was all over. The boat broke up & the boys were all in the water treading water screaming & yelling at each other. I watched with fascination at the sight of it all. I felt a bulge forming in my trousers as they swam wearing their full winter uniforms,shoes, socks everything. It would have been hard work swimming wearing raincoats, blazers, sweaters, heavy wool grey winter school trousers, long sleeved dress shirts with ties, shoes & socks. I nearly blew in my trousers watching all that heavy wet clothing. I couldn't see that Mr Horan was achieving absolutely nothing by yelling & waving his arms around uselessly. I looked around to see if there was anyone who could help. I ran down the beach until I found an old man cleaning his boat. I told him what had happened & he put his little boat into the water immediately & rowed out to retrieve the boys. When he got there they started trying to clamber on board. The water was absolutely pouring out of the woollen blazers, sweaters, scarves, gloves & hats. His boat was to small to hold them all as well as the water running out of all that heavy clothing. I noticed that the big fat kid managed to somehow get his fat arse on board even though it was largely through his efforts that the boat had sunk in the first place. His sodden pants were starting to slip down exposing his ugly butt as he was dragged whining & complaining by the back of his sodden blazer. Not a nice sight at all.I think the whole thing was mostly his idea to begin with. He was after all the loud mouthed school bully. It was great to see him get his come uppence. He wasn't a happy camper.

I decided to sneak back to the school while this situation was being sorted out. The boys were marched back to school with their shoes & socks squelching noisily. The water was still streaming out of all that heavy clothing.

We returned to the next class which happened to be maths. Everyone was asking where the boys were & why Mr Horan was late for class. I knew why but kept my head down. Suddenly the door swung open & the five boys were marched in. My jaw dropped in amazement. The were standing in a row wearing nothing but their Speedo swimming briefs. Just as if they were at a swim meet. Some looked totally embarrassed while some seemed to be smiling like class clowns. I suddenly wished I could have been one of those boys. I was turned on by the way I had to stay dry in my full school uniform & winter woollies whilst they got to swim in full school uniform & then wear Speedo swimming briefs. It would have been humiliating but a big turn on for me. I kicked myself for not going boating with them even if it would've been bloody freezing in that snowy water. They each received six of the best in front of the class & even though I felt sorry for them I kind of envied them & wished I could just run down to that beach & dive into that cold grey water without stopping to remove anything. Just entering the water fully clothed. I had already learnt the hard way that that was definitely out of the question.

Mr Horan told the class what had happened & ridiculed the boys about going swimming too early in the day. He asked them why they had started their swimming training without him. Also he berated their choice of "swimwear" as being far too heavy to be competitive. He was clearly enjoying himself. Now that their clothing was wet they had to stay & continue their classes wearing the only items of their clothing that had remained dry. Ironically their "correct swimming attire" My bulge was tent polling my dry grey trousers by now. I wished I could have gone swimming wearing my uniform & then be forced to wear nothing but swimming briefs in class. I couldn't stand it anymore & I put my hands in my pockets & started to play with myself. In a short time I exploded in my pants & felt the warm custard fill my underpants. As I left the class that day I had to hold my school bag in front of me to hide the creamy stain on the front of my trousers. At the end of the day the angry parents all agreed to continue the humiliation. They were picked up & taken to the heated pool to have their proper "swim" still wearing nothing but their Speedos & clutching massive plastic bags containing their wet school uniforms. Looking back on it now maybe the fact that they got wet & I didn't was a pretty massive turn on for me as I was now the little dry sensible short haired nurd guy behaving himself while others got wet instead of me. Before I went to bed that night I showered in my long flannelette winter pyjamas while my parents were downstairs. Luckily I had many spare sets because I filled my underpants & wet clinging pyjamas completely with my man custard. School isn't always bad. There are some great days.
Cheers, Winter Woolly Wetboy.


Cheers, Winter Woolly Wetboy.
Comments:
washme01:
4/2/25
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Awesome story.
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