UMD Stories
13 results

Cold water corduroy
Story by WinterWoollyWetboy5/11/25 138 viewsmale+female, explicit
Hi fellow wetlookets, Now that the weather is getting cooler I'm swimming wearing dark olive straight leg corduroy jeans, (My thickly whaled corduroy dress trousers have faded too much & I can't get my hands on new ones.) Over the top of my unde...
The pool cleaners
Story by WinterWoollyWetboy1/12/25 508 viewsmale+female
Hello fellow wet lookers. Here's another story from my younger days. I was in my early 20s and temporarily out of work. I saw an advertisement for a pool cleaning job & knew that for obvious reasons this would be a line of work that was right up...
Early Spring Swim
Story by WinterWoollyWetboy9/18/24 178 viewsmale
Hi fellow wet lookers, it's early spring here. Its still cold in the nights & mornings but it becomes milder in the middle of the day. I had to attend a meeting at work and was dressed nicely today. The morning was cold so I dressed in my best ol...
Surfing in your work clothes
Story by WinterWoollyWetboy8/31/24 269 viewsmale+female
Hello fellow wet lookers, Yesterday was the last day of winter but the weather was unusually warm. I was at work but being near the sea it was hard to resist going for a surf the only problem was that I didn't have my bathing suit with me. I hadn't r...
Summer Woolly Wetboy goes to the beach.
Story by WinterWoollyWetboy7/14/24 285 viewsmale+female
Hi fellow wet lookers, Here's a memory of high school or more correctly a hot summers afternoon after school had finished. Picture the scene. It begins with a stinking hot day at school. These were the days before schools had air conditioning. Us poo...
The pool party.
Story by WinterWoollyWetboy7/11/24 354 viewsmale+female
Hi fellow wet lookers. Here's a story from my teenage days. I was sixteen at the time of this story. Try to picture a young teenage male living under the control of his extremely religious & conservative parents. He's not allowed to swim because...
Wet but not wet
Story by WinterWoollyWetboy6/29/24 197 viewsmale+female, synthetic
Hello fellow wet lookers, I've gotta tell you I think I've found the perfect job. I'm now assisting an engineer on field visits. She inspects huge dams for large industrial farms & community projects. She's a beautiful brunette with an absolutely...
Body surfing in winter
Story by WinterWoollyWetboy6/25/24 153 viewsmale+female
Hello fellow wet lookers. Have you ever been walking along a beach in winter fully clothed & suddenly felt the urge to have a swim or a surf even though the weather was cold & you hadn't actually planned to go swimming? Just going straight in...
A totally unexpected swim.
Story by WinterWoollyWetboy6/23/24 396 viewsmale+female, explicit
Hello fellow wet lookers. Sometimes the best swims are totally Unexpected such as going too far whilst washing a car. When I was a sixteen year old boy I lived with my religiously conservative parents who never let me swim on the grounds that wearing...
Office clothing as swimwear?
Story by WinterWoollyWetboy2/5/23 467 viewsmale+female
Have you ever been stuck in an office with no air-conditioning on a very hot day? I have. It was near a beach & I could see people swimming & surfing through my window while I sweltered in my office clothing. I was wearing underpants briefs &...
The big boating fail.
Story by WinterWoollyWetboy1/4/23 233 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...
School Daze
Story by WinterWoollyWetboy12/21/22 609 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 st...
My first post Early days
Story by WinterWoollyWetboy11/22/22 468 viewsmale+female
Hi fellow wet lookers. This is my first post so please forgive any etiquette or format rule breaches as I'm still learning & I'm not too tech savvy. This is my first story. It's called Early days. I became a wet looker I believe because I came f...
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