The guy moving into the apartment across from ours just seemed like a typical early, middle-aged 40s dude. I didn't pay that much attention to him. He a couple of guys were muscling his furniture and boxes up the concrete stairs and into his apartment. I said hey and he introduced himself as Harold. I told him I was Kevin and gave his buddies the nod as I walked past them and opened the door to my grandmother's apartment. I'm not sure those guys even noticed me. I was young, about 5'6" and weighed 125 lbs, with very fair skin. Being a late-bloomer, I didn't even have to shave yet.
I had just turned 18 a few months before I met Harold for the first. I was living with my grandma as my parents had split up and we weren't getting along. Though I was supposed to go to college, I really lacked much motivation at the time.
A few months before moving in with her, my grandma got an insurance settlement and decided, at age 60, to buy a bar. Suddenly, she was gone all the time, generally leaving at 2 in the afternoon and coming home after midnight, or not at all. Grandma still had wild oats to sow.
With all the free time, I jerked off a lot to internet porn. I found myself identifying more with the girls I watched. I would imagine that I was the one sucking that enormous cock or being tied up and ass fucked by a scary master. Of course, I found my way to Craigslist and all the ads. I was very scared at first but I eventually met with a couple of guys.
The first guy was a disaster. He wasn't at all like he described himself. We met in a parking lot and I got into his car. He was an awful lot heavier than he said and his cock was not nearly as big. I wasn't all that attracted to him but felt obligated. Luckily, he accepted a handjob and I was on my way, feeling grossed out by him but kind of dirty for at least taking the plunge.
The second guy was a lot better. He was a business man type in his 50s. He took me to his office and could tell it was my first time. He was about 6.5" and nicely thick. He let me take my time and gave me instructions on how to suck him. For a couple of months, we met at least once a week and I blew him and he slowly worked up to fucking my ass. It was fun and it taught me I really did love being assfucked, but he didn't care for being dominant. So, I still was searching when I saw a new ad a couple of days after Harold had moved in. It said newly single guy seeks dedicated submissive slut.
I responded telling him I was looking to be a dedicated submissive slut. Within an hour, he responded and explained that he had just moved into an apartment after getting a divorce and that now he could finally live the way he wanted to live. He described himself as being 5'10" 185 with graying hair, in his mid-40s with a 7.5" cock that was very, very thick. I replied and described myself and told him it would be funny if he was the guy would had moved into the apartment across from me. He replied with one word: "Kevin?"
I was a little freaked out at first and almost logged off and hid but then I thought, Harold seemed like a harmless enough guy. So I responded: "Harold??!!!!" He shot back a reply telling me to come on over. He would leave the door slightly open and I should come in and strip and come back to his bedroom. I said yes and shut down the computer. Barefoot, in just a pair of shorts and t-shirt, I walked across the breezeway toward Harold's door. It was slightly ajar. I was breathing nervously and slowly pushed the door open and walked in.
