I suppose that all of us have at least one crazy relative. For me, it was my mom's brother, my Uncle Josh. My Uncle Josh was a barrel of laughs, the guy who was always the life of the party. His philosophy of life boiled down to one simple thought: Living is just a short trip to the grave, so you might as well enjoy what you can along the way.
To say he enjoyed himself would be an understatement. He lived a wild and hard life, never getting married or even having a steady job. He had a lot of bad habits, from women to gambling to whiskey, and was always in some kind of trouble. He lived every day like it was his last, which became self fulfilling when he died suddenly of a heart attack at just 50.
That turned out to be a classic case of good news / bad news for me. The good news was that Uncle Josh left all of his possessions to me, the only relative he had who hadn't disowned him for his bad behavior. The bad news was that I quickly determined that the sum total of his possessions was an endless pile of crap that he had collected in his fourth floor apartment, which I was now responsible for cleaning out. Uncle Josh was a bit of a hoarder, and cleaning all the stuff out was not going to be an easy task. I decided that the best approach would be to take a few weeks off work and move into Josh's apartment until I could get rid of all the stuff, most of which was going into the dumpster.
On the plus side, Josh lived in a pretty good sized city, which was a real change for me coming from a small town. It wasn't long before I had met several of Josh's neighbors in the apartment complex, all of whom had some fairly entertaining stories about my crazy uncle. Some of his neighbors were very attractive females, and I got the impression that despite the fact that they were probably 30 years younger than my uncle, there may have been some sexual history there. Uncle Josh had a silver tongue and a way with women, he was known for having lots of girlfriends. Unfortunately I didn't inherit his smooth ways, I was more of a shy nerd who spent more time fantasizing about women than having sex with them.
After a week at of steady work I had sold, given away or thrown away the vast majority of Uncle Josh's vast holdings of worthlessness. In addition to being a hoarder, he had a bizarre system of organizing the myriad of worthless things he saved. He would put things into containers and label them with two large letters, with a more detailed description in smaller letters that were completely unreadable. So PC might mean "potato chips," or "parts for computer" or in some cases both. I swear I found some containers labeled MT, which ended up standing for empty.
I thought I was down to just the bathroom, but then I discovered a small eave storage attic that was filled with probably a hundred milk cartons, stapled shut at the top and labeled CM, which I assumed meant "cartons of milk". I shook one and didn't hear anything in it, so I decided they were empty and started the process of piling them up by the front door to then haul them down the elevator and over to the dumpster. But by the time I got them all out and piled up by the door, it was late in the afternoon, I had a splitting headache and I made the decision to take the rest of the day and night off.
I went to the bathroom and discovered a container with the letters PM on it, and after opening it up saw the familiar blue colored Tylenol PM pills. I took three, washed them down with a cold beer, and stretched out on the only remaining furniture in the place, a sofa.
Now usually when I take three Tylenol PMs and a beer, I'm out within 30 minutes for the next ten hours. But for some reason I couldn't get tired, and my mind started wandering. I started thinking about some of the hot girls I had met in the apartment building, creating my usual fantasies about me cleverly seducing them and ending up together in the sack. Not surprisingly, my fantasies began to have an influence on my cock, and before long I had a full on erection.
Then something curious happened. That full on erection just kept going. For some reason, maybe because I hadn't had sex in a while, my cock had gotten extra hard and was practically throbbing. I slipped my shorts down and wrapped my fist around it and let my fantasies take over, and it wasn't long before I had a very intense and soggy orgasm.
So I was in the midst of coming down from that very intense orgasm when something else peculiar happened. My erection didn't fade. I consider myself of normal stamina for a 30 year old man, I have an orgasm, and maybe after 20 minutes or so I might be able to get it back up again. But I'm looking down at my cock and it is as hard, if not harder, than it was before. I could hardly believe it, but I was stroking my cock again immediately after having an orgasm.
That's when it hit me, like a bolt out of the blue. I pulled my shorts up and ran into the bathroom, picking up the container marked PM. I looked down at the bottom of Uncle Josh's label, where he had scribbled his description. After several minutes of trying to read his eligible handwriting, I finally figured out what was written on the bottle, and it wasn't "Tylenol PM." It was "Penis Medicine." Instead of taking three Tylenol PMs, I had taken three times the normal dose of Uncle Josh's Viagra stash. Adding to that, the load I had released was so substantial it had gotten all over my shorts, which was the last clean pair I had.
I was still staring at the tent in front of my shorts while processing this information when I heard a knock at the door. So I'm standing there in the bathroom with a giant boner and cum stained shorts, and the only thing I have to put on is one of Uncle Josh's Scottish kilts that I had saved as a memento. Uncle Josh was proud of his Scottish heritage, and one of his many part time jobs was playing the bagpipes at funerals,. The kilt was part of the costume. Still in a stupor of sorts, threw on the kilt, I opened the door and saw the girl from the apartment next door, looking pretty frantic and also dripping wet.
"Hey, I'm Linda Reno from next door, I hate to bother you but my kitchen sink is leaking and I don't know how to turn the water off..." she said, before trailing off. "Are you wearing a dress?"
I looked down and realized it did indeed appear I was wearing a skirt. "No, its not a dress, it's a kilt," I stammered. I was a bit distracted by the wet t shirt she had on, the throbbing monster between my legs, and the passing thought that maybe I should google "can you OD on Viagra," but I was able to stammer out an Ok and follow her into her apartment.
I'm no plumber, but I was able to get the water valve turned off pretty quickly and figured out that the supply line had sprung a leak. Lucky for her I remembered that Uncle Josh had an extra hose so I went back to his apartment and got the hose and a wrench, taking the time to splash some cold water in my face in an unsuccessful effort to somehow slow the blood flow to my crotch. When I walked back into Linda's apartment, I had to hold the wrench and the hose in front of my crotch and bend over to hide the erection straining the kilt. It didn't help at all that Linda was still wearing a wet white t-shirt and cut off jeans that showed off a great looking pair of legs. I mumbled something about having my stuff to fix the leak and I couldn't help but be paranoid that she was smirking at me for my obvious issue.
Moving into position to fix the leak didn't help. I ended up on my back with my head in the cabinet, and even though I was engrossed in plumbing work, which is the least sexy thing imaginable, my cock was straining the kilt at full attention and there was no real way to hide it. I didn't have underwear on, so as the kilt rode up on my legs it was hard to hide my erection. The kilt was made of a silky material, so as my cock became aroused it slid around under the silk, which made it more aroused. With my head tucked away under the sink, I couldn't tell much I was exposed. And the thought of my erection being on full display in front of Linda was only making me even more aroused. At some point I just gave up and went with it. I got the sense that Linda wasn't offended, and was maybe even enjoying keeping me aroused. She kept asking me if I needed any help, or a beer, and she would stand there straddling my leg and lean down to watch me work.
"So if you don't mind me asking, just how did you end up wearing a skirt?" she asked.
"Not a skirt, it's a kilt," I said. "It's a Scottish thing." I spent the next few minutes explaining where the kilt came from and how I had ended up with no clean clothes, leaving out the details about my Viagra overdose and losing a load on my shorts. All while working on the plumbing and maintaining the erection.
"Well its not a bad look for you," she laughed. "Good thing you have nice...legs."
The pause seemed pretty pronounced, and I couldn't help but get a vision of her looking under the kilt at my cock as she said it.
"Thanks, uh, you too," I grunted while tightening a pipe connection.
I was getting close to finishing up but was enjoying myself too much to rush. Then she dropped the bomb on me.
"So is it true, what they say about what men wear underneath a kilt?" she asked.
