My roommate Pete and I rented the upstairs apartment of a two-story duplex our sophomore year at college. The semester was almost over. Pete was going home to Chicago for the summer. I was probably going home to Columbus; I couldn't afford our two-bedroom apartment alone. Pete and I loved the place and were sad that we would probably lose it to renters who might want it for the summer and the school year.
In early April I was returning home and Derek, our landlord who lived downstairs, was in the driveway, washing his car. It was in the mid 70's and sunny. A good day for a car wash.
"Hey," Derek said, "been meaning to talk to you about your lease. Any thoughts on what you guys are going to do?"
"Well," I said, "it's up the end of May, right? To be honest, neither of us wants to give it up, but Pete is going home and I can't afford to keep the place alone."
"So," he asked, "you're returning home only because you can't afford this place alone? You would stay if the rent was cheaper?"
We talked for a bit. I told him that I would prefer to stay but I would need to save money, and paying for an apartment alone was not going to permit me to save much. After chatting for a few minutes he said: "I have a proposition for you. I like you two and I think you both like living here. Finding new renters is a pain in the ass. You guys pay on time. And you don't make a lot of noise or beat the place up. That's tough to find. I'd really prefer it if you stay, so here's the deal: I'm going to Europe for most of the summer. If you agree that you guys will start paying rent again in September and renew until at least next June, and if you agree to keep a watch on the place, mow the lawn, take in the mail and things like that while I'm gone, I'll let you stay in your place rent free for the summer. How's that sound?"
I was stunned. Blown away, really. Without a second's hesitation I said "yes."
He smiled and said "Excellent."
As expected, Pete was happy to hear the news. Not only did it mean that we didn't have to find a possibly lesser place for next year it also meant that we wouldn't have to move our stuff home and then lug it back in late August.
During the last weeks of the term Pete and I got to know Derek a bit better. He invited us down to share the occasional pizza and we began offering to help him do things around the house. I got the mower out one day and mowed the lawn, which surprised Derek. "I might as well get used to it," I said. And things went on from there.
The school term ended. Pete went home, promising to come down and visit me during the summer and making me promise to come up to Chicago for the 4th of July if I could get the time off from work.
It was the first Friday night after Pete had left and I was sitting on our back deck, looking down at the back lawn. The campus town had pretty much emptied out. I was enjoying the quiet and a cold beer, thinking about what I would have for dinner. Derek came out into the backyard below me. I yelled "hey" to him. He yelled back and asked me if I wanted to join him for steaks on the grill. He didn't have to ask me twice.
I grabbed my cooler and my beer and went down the stairs, placing both beside one of the Adirondack chairs he kept in his tidy backyard.
At this point I should probably describe myself and Derek. I was 19 that summer. I weighed about 135 pounds soaking wet and stood about 5 feet 9 inches tall. I was lean with little real muscle mass. It didn't matter how much I ate, I couldn't seem to gain any weight. I had a mop of brown hair on my head, green eyes and I had had enough girlfriends to know that I was considered cute by some. I was never going to go home with the lead cheerleader if what she wanted was muscle mass and a square head, but I was ok with that.
What the girls I did go out with sometimes found out was that I had a nice cock. Hanging soft it was typically around 4". Fully hard it was just under 8" and almost as thick as a coke can. Not quite, but almost. I had been expertly cut by a doctor who knew what he was doing 19 years earlier.
This was the early 80's, so shaving was not a "thing," and I had a nice pleasure trail that started at my belly button and snaked down to a big brown bush that surrounded my cock and balls.
Derek was in his late 20's. He was good looking. He had straight blonde hair, that he parted in the middle and that went down to just above his shoulders. He probably weighed about 160 or so and was about an inch taller than me. He wasn't buff but he did have some defined muscles that I later learned he earned by lifting weights a few times a week.
Both Pete and I were curious about Derek. He was really only a few years older than we were; we both had older brothers who were his age. He owned the duplex we lived in, and we knew he owned a few others in our college town. We were curious how he managed to do all that by such a young age.
Derek pointed me to the kitchen and told me to make up a salad. I grabbed my beer, headed in and he tended to the steaks on the grill. After a bit, he came in and dropped some corn into a pot that had been boiling and uncovered a pan of greens. It was only then that I realized that he had intended to be cooking for more than himself, but my thoughts progressed no further than that observation.
The steaks and the corn were ready, so we loaded up our plates and went out back to the Adirondacks. We ate and talked. When we finished, we quickly cleaned up and went back outside to have another beer. It was turning dark by now. I had a nice buzz going. I wasn't drunk but I was certainly feeling good.
This was my chance to find out what Derek's deal was, I thought. "So," I asked him, "how is it that you own this house and some other houses in town and you're probably not yet 30?"
He smiled and said, "bet you two have been wanting to ask that for most of the year." We both laughed and I admitted that we did talk about it.
He then told me his story. His parents lived in upstate New York and they were pretty wealthy. "Generational wealth," he called it. So, even if he didn't own the seven (we were off by 3 or 4!) duplexes in our college town that he did, he would still not really need to work for someone else.
"I came out here to school where no one would automatically know my last name," he told me. "While I was in college, I decided to buy the place I was living in," he said. "That was this place. I spent a lot of time and invested a bit of money to modernize it and fix it up. I've continued buying, fixing up and renting for the last six years. I now have seven duplexes spread across town. The other six are managed by a guy I hired, so I don't have to deal with them. I like it here and have decided at least for now to hang for a while."
We sat and drank. "I do have one other question if it's ok to ask," I said. "Sure," he responded.
"I never see a girl around. You're a good looking guy. What's up with that?" He looked a little startled. I actually surprised myself. Pete and I had speculated about Derek's sexuality. We'd never seen a guy come to the house, but we'd never seen a girl come by either. He was good looking. He was young. Obviously doing well--he drove a newer Corvette in the summer and a new Jeep in the other months. And yet we'd never seen a pretty young thing doing the walk of shame down the driveway at dawn.