A Wild and Crazy Night

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.

My heart fluttered for a moment, but I steeled myself and went with pretty the only right answer.

"I suppose you will have to check," I answered, my head still under the sink.

Things were quiet for a moment as I stared up at the bottom of the cabinet, waiting for something to happen. Then I felt her hands on the bottom of the kilt, sliding the material up and over my waist. Now my massive Viagra injected boner was on full display, and I may have imagined it, but I thought I heard a gasp.

"Hmm," she said. "Nothing below the kilt, and it looks like plumbing really turns you on."

My mind scrambled to try to think of something clever. "I'm sorry, not sure what's going on there, sometimes it has a mind of it's own," I mumbled.

"Nothing to be sorry about," she said.

Stretched out on my back with my head under the sink and not being able to see her say the words, I had a really hard time trying to figure out what she meant by that. Was she trying to keep me from being embarrassed? Or was she actually looking at my cock when she said it?

Lucky for me she settled it pretty quickly.

"Maybe I can help you with that while you're working" she laughed, and I felt her hand slip around my cock.

"Yes!" I practically shouted, and I tried to get up to quick and smacked my head on the pipe, causing her to giggle.

"Take it easy big guy," she said, her fingers still wrapped around my cock. "You don't want to get your skirt in a wad."

"It's a kilt," I gasped from under the cabinet.

Words can't express how good it felt to have her hands around my surging cock. I was already done with the plumbing work, but I stayed there and pretended to be working while her hands massaged my cock.

"That's a mighty hard cock for a man who wears a dress," she said. I felt her lips on my cock.

"Kilt," I grimaced, before letting out a groan of pleasure. I slid my head down out of the cabinet. "I'm finished," I added.

"Finished?" she said, taking her lips off my cock and looking at me with disappointment.

"I'm finished with the plumbing," I replied, and I guided her head back down onto my cock with my now free hands.

She took me deep into her mouth, and the visual of that plus how big and full my cock had gotten was amazing. Even better, because I had just jerked off, I wasn't worried about coming too soon. I was hard as a rock and in complete control.

And I stayed in complete control, for the next ten minutes of an epic kitchen floor blow job. Then another ten minutes of me tearing her clothes off and setting her on the kitchen table where I went down on her. Then another thirty minutes of me taking her into the bedroom and fucking her harder than I had ever fucked a girl in my entire life. Then thirty seconds of downtime before I was once again, stunningly and fully aroused. I think Linda had been looking forward to having a break, and when she saw my cock had gotten hard again immediately she had a look of both passion and nervousness on her face.

She had that look on her face for the next thirty minutes as we went through every single sexual position in the book. Every single thrust my cock was rock solid hard. From her moans and writhing I could tell she was enjoying it, but I could also read the look on her face that said "am I fucking some kind of alien here or what?"

I had experienced times in my life when I couldn't orgasm. I had experienced times in my life when I couldn't get hard. I had experienced times when I came too soon. This was none of those. I was completely aroused and completely in control of my orgasm, and I was taking my sweet time and enjoying every second.

At the thirty minute point I started getting the sense that the half dozen orgasms Linda had been through and the look of exhaustion on her face suggested she may have had enough. I moved her into the doggy style position and got into a slow steady rhythm of bearing my cock deep in her and then pulling it almost all the way out. Gradually I began to quicken the pace, my hands gripping her ass. Then I started pumping faster and faster. It was so amazing that I started to count how many times I was pumping in and out, I lost count at over a hundred. It felt like I started my orgasm after ten minutes in that position, and it kept building and kept building for the next two minutes. By the time I finally fully released she was practically screaming with pleasure and I was moaning like a banshee. It literally felt like my dick exploded as we both fell forward into a heap on the bed. Despite the intensity of the orgasm my cock still didn't immediately relax, and I kept my cock inside her as we lay together catching our breath on the bed.

"Wow," she said after a while. "Men who wear dresses can fuck like nobody's business."

"Kilt," I groaned. "Yeah, sorry about that I guess I was just super horny." I didn't want to reveal the whole Viagra thing, in part because I was so proud of my sexual performance. It was like a masterpiece of hard fucking.

"You aren't going to, uh, get hard again are you?" she asked timidly.

"No, I'm good," I said, sliding my cock out of her. My cock had begun to soften just a bit, finally.

"Oh thank God," she giggled. "I mean, don't get me wrong, that was pretty fantastic, but holy shit, I've got to work tomorrow."

Linda got us a beer and we chilled in the bed for a while, chatting. The conversation turned over to my Uncle Josh, and she told me a few Josh stories. Some were the typical ones I had come to expect, usually centered around having too much to drink, but she did share a few stories about how Josh helped her out a couple of times, even gave her a lot of money when she had some tight times, and never asked to be paid back. She also bragged about how Josh taught her how to play black jack, and that she had gotten so good she had gotten a part time job as a black jack dealer for special events.

Eventually there was a lull in the conversation, and I realized that Linda had dozed off. Actually, she had fallen off into a deep sleep, and judging by the smile on her face, it was a very contented sleep.

I got up quietly and found the clothes that were spread out between the bedroom and the kitchen and let myself out, going back to Uncle Josh's apartment. I was pretty exhausted, though also very satisfied, but I was brushing my teeth and looked down and damned if my dick wasn't hard AGAIN.

Up to now I hadn't really had too much time to worry about the implications of taking 3 times the normal dose of Viagra. I had enjoyed, immensely, some fantastic sex and three fabulous orgasms over the past several hours. But while my cock had gotten hard again, there was also a dull ache, like you would get if you overused a muscle that had not previously had that much exercise. My cock had experienced a lot more exercise than it was used to, and while I usually enjoyed the experience of being hard, it was starting to get old.

I stripped down and took a lukewarm shower, and that seemed to help. I was just down to half staff. I decided that maybe getting something to eat would help, so I got dressed again and headed out to the corner store.

Unfortunately the only thing I had available to wear was my t shirt, flip flops and the kilt, but I figured it was pretty late so I was unlikely to run into anyone. Of course I was wrong.

When I was walking down the front steps of the apartment building I saw Alice Green there on the steps. Alice Green was the hottest girl in the whole building, she was hot on a whole different level. To put things into perspective, if Linda Reno was, say a 7 on a ten point scale, Alice Green was a 12.

Alice was exotically beautiful, with long curly black hair, blue eyes, dark smooth skin, and a body that was perfect in every way. I knew her name because after the first few times I saw her and lusted after her I figured out what apartment she lived in and tracked down her name on the mail box, then I looked her up on facebook and spent a few hours looking at her pictures, then I figured out what time she came home everyday and made an excuse to be walking outside at that time. Since I had been at Uncle Josh's place I had experienced several orgasms fantasizing about her. So when I say hot I mean hot enough for me to go full stalker on.

But sadly I had been unable to muster up any kind of conversation with her. I talked to her enough that she knew I was there to clean up Josh's place and I was from out of town, but I doubted she remembered my name. Of course I was wrong.

"Hey Mike," she said as I walked past her on the steps. She sniffed a little and I realized she was crying.

"Oh hey ...uh... Alice," I said, trying to play it cool like I didn't quite remember her name. "Are you ok?" I asked.

"Yeah, well I guess," she said, but then she broke down and outright cried. "Except that my fucking boyfriend accidentally sent me a video of him fucking another girl."

"Oh, that's not good," I said. I sat down beside her on the steps. "Just for the record, I'd say he was making a huge mistake."

"Thanks," she blushed. It was apparent that she had been drinking, and til then she hadn't really noticed what I was wearing. Then, she stopped and did a double take. "Say, are you wearing a dress?" she asked.

"Not a dress," I said, rubbing my forehead. "It's a kilt, it's like a Scottish thing."

I went on to explain about how I had run out of clothes and it was the only thing Josh had to wear, and my convoluted story seemed to take her mind off her boyfriend troubles.

"Well I will have to say, it is a very cute kilt," she grinned. "If you decide you don't want it I may be interested."

We laughed and talked about Josh for a while, she also had some great Josh stories, and as it turns out she admitted she still owed him $5,000, which I told her not to worry about, which made her extremely happy and appreciative, which led her down a path to talk about how both me and Josh were really good guys, and that led to her talking about how her boyfriend was not such a nice guy, that he was really an asshole, which led her to suggest that maybe I would want to see the video of him with that slut in 7-A, which I gently talked her out of.

"You know, if I were you, I would just go out and find another guy and show him that you don't need him," I said. "You're a beautiful girl, you could have any guy you wanted."

She nodded in slightly drunken agreement and said that I was so smart and so nice, and then she got a weird kind of look in her eye, which I didn't realize until it was too late, and by too late I mean that was when she asked "Hey what about you?"