My summer with Kirk ended. He moved on and so did I. I moved to a large city and began college. My parents didn't like the idea of my living in a dorm so they made the decision to rent an apartment for me in an exclusive area of the city. Being a kid raised in a sheltered environment, they felt I needed to have my own place. Personally, I was happy as a clam about it. Having my own place would ensure certain privacy for me and my activities, no matter what they might be. Given my sexual preferences at that point, I didn't want a roommate around.
I moved in just before classes started and when school began, I settled into my studies. I did well and, in fact, was soon bored with school. When things like that come easy to you, it's easy to have time on your hands. Soon within just a few weeks, I was bored out of my mind and horny. I hadn't met anyone yet and certainly hadn't been with anyone since Kirk. I kept myself in good shape, nice and smooth, still feminine in many respects in case I met someone that turned me on.
In those days, the very early '90's, there still was no internet and so you had to meet people the old fashioned way, you went looking for them. In those days, places like the Y, the adult book stores, adult arcades and theaters, gay bars (for which I was still too young) and personal ads in the local newspapers were the only ways to meet someone interested in the same thing as you, unless you knew someone. So I began looking around.
I was picky to be sure. I don't deny it. I seldom saw anyone I care for at any of the "usual" places. I spent weeks just cruising around. I got plenty of offers but I saw little that turned me on. Finally, one weekend I scanned the personals in the newspaper. There were several ads that caught my eye. A couple in particular were older wealthy men (or so the ads claimed) seeking young houseboys or sugar babies. So I decided to answer both. Each had a telephone number and so I called. What the hell!
The first ad was placed by a guy across town in one of the older sections of town that was really affluent but had gone to seed to some degree. However, there were still older people there with money, so I thought it was worth a shot. I called the gentleman and he was very friendly over the phone. He invited me over that afternoon. I took the directions and drove across town to meet him.
When I arrived at the address, the house was very nice, up a long drive. It appeared well-kept and I felt okay about it. I got out and went to the door. After ringing the doorbell, it took a moment but the door quickly opened. The gentleman was older, probably in his late 40's, and quite handsome for his age. Keep in mind that at that young age, I thought of late 40's as being really old.
He smiled and spoke, "Hi, there. I'm Jim. Come on in."
I walked in and looked around the foyer. The place appeared clean from what I could see and was well-decorated. Jim shook my hand and I introduced myself.
"Hey, I'm Jamie," I informed him.
"Well, Jamie, I'm glad to meet you. I'm also glad you answered my ad."
I smiled at him, but was very nervous. I couldn't believe what I was doing. And then I thought, I really wasn't doing anything yet. Just meeting someone.
"I'm new in town and just was looking around for a friend here, I guess," I told Jim.
He smiled gently and laughed, "Well, you got one now!"
He invited into his den and offered me a seat. I sat down and tried to get comfortable. He took a chair across from me and leaned back.
We began to talk and tell each other about ourselves. I told him my story as it was so far and he told me about himself. He was divorced and had been for several years. He had children but they lived in another state. He had began messing around with guys after his divorce and really loved it, so he didn't bother getting involved with another woman.
Finally, he got to the "meat" of the ad, pardon the pun.
"So, Jamie," he began, "I'm looking for a young man who can satisfy my need for sex. I enjoy young guys and I like to be in control. I'm older but I still have plenty of energy. Make sense?"
"Oh, yeah, absolutely," I told him.
He smiled and continued, "And so I'm looking for a young guy to basically be a houseboy, someone to play with and to help around the place. I'll provide a place to stay, some spending money and you can be my private playmate, my own sex toy."
He smiled and winked. I looked around. The place was nice and I could use the extra money. But I never had thought of myself as being a whore and that's basically what we were talking about, wasn't it?
Finally Jim spoke up again, "So... what do you think, young man?"
I stammered just a bit, "Well, sir, I'd have to think about it."
Jim laughed and quickly said, "That's fine. No problem. Would you like a tour of the place?"
"Sure," I told him and he gave me a tour of his home.
The place was big and nice. It was certainly a place you could get accustomed to living in. His basement was basically a recreation center and he had a private bar, a beautiful study with mounted heads and rugs on the floor. He showed me upstairs and gave me a tour of the master bedroom suite. It was amazing. The room itself was huge with a king size bed, warm colors, mood lighting and a master bathroom you could live in. I have to admit I was impressed. I also felt it was pure luck to meet this guy on the first outing.
He smiled at me as I marveled at his bedroom. He noticed my amazement and spoke up, "You like this room?"
I nodded and gulped. The room itself was kind of turning me on. Weird!
He reached over just slightly and touched my ass. I was wearing shorts and his hand slightly brushed against the back of my leg just under my ass cheek. I jumped and looked at him. Jim only smiled.
Then he spoke up, "Has it been a while, son? It has for me."
I felt nervous as shit at that point but still turned on. He wasn't bad looking at all, just older than I was accustomed to.
