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I was nervous. Now that you could see Chicago down below through the plane windows, I wasn't sure if I wanted to go through with this. No doubt Master was already at the airport waiting for me, he believed in being early. I wondered if I could somehow evade him at the airport and find a plane to take me back to NY. I was in full panic mode.
I had met Master Nick a few months back. He came to NY to attend a 'Farmers convention' and had put up a post on Craigslist. I had replied. He had replied back. He was in NY only for a week. Eventually he extended his stay by a month for me. By then I was in love and couldn't imagine not belonging to him. But he had to go back. Before he left he gave me an offer. To be his bitch fulltime at his ranch back in Illinois.
Sex wasn't hard to come by. It was New York after all. And I was pretty goodlooking, 5'10, jet black hair, jet black eyes, milky white skin, 160 pound six packs, 24 years old (my hardon was a pretty underwhelming 4 and something inches but I was a bottom so what did that matter?). I made sure to hit the gym early every day. I co-owned pretty successful restaurant in upstate NewYork that I had started with my college buddy three years ago right after college. We had rented a building, put our sweat and blood into it. Now we owned the place. With good profits he had gotten a loan to meet his share of the capital. My parents agreed to lend me mine.
I never went beyond a one night stand. It wasn't that the sex was bad. It just wasn't the kind of sex I wanted. I wanted to be made to kneel down, with a collar around my neck, humiliated, petted, manhandled, the kind of sex you are too scared to admit you like . I would spend hours looking up posts online that fit my fantasies, but I never messaged them. Always jacked off to it and chickened out afterwards.
Master Nick's post was the first one I replied to. Since he had made it clear he was only in NY for a week I finally decided to reply instead of jacking off. I was hoping for something casual that would last no more than a week. I told myself we would probably not even meet up for a second time. After we exchanged faceless body pics and liked what we saw, he proposed to meet me at a bustop near my apartment. That way if I was not the guy in the pics I had sent him, he could back off. When he drove up in his black Mercedes, examined me from head to toe, opened the door and told me to get in, I knew he approved. He drove us to the Plaza where he was staying. In his room he laid down the basics for the night. Once the collar went on, there would be no speaking. No walking around on two legs. He never wanted to see my dick. Since I was wearing boxers, he made do by tearing open the back to get to my asshole. He told me he expected black jockstraps from then on. According to him, bitches needed to come only once a week. Since that was how long he was going to be in NY, that meant no jacking off or cumming for the duration of his stay. I break any rules I get punished. Once we were done and the collar was off, he asked me if I had enjoyed it and wanted to do it again. I looked at the ground and nodded. He slapped me on the face and said "When I ask you a question, I expect an answer bitch". I was taken a bit by surprise but gathered my wits and answered "Yes Master. I liked it and I want to see you again". I was hard in my boxers.
After that we got to know each other a little over room service. I told him about me and what I did. He told me about him. He had been orphaned young. His grandfather looked after him at his ranch in Illinois. Once he came of age, instead of taking over his parents assorted businesses in Chicago, he sold most of them off and had it invested. What he didn't sell, his lawyers look after. He worked on his grandfather's farm and that was the life he had grown to like..... on the farm, growing corn. Though the ranch was huge, they did the work themselves and hired help only when they needed it. He travelled regularly. During his stay in the city, he enjoyed his luxuries. Back in his ranch, he enjoyed the hard work. His grandfather had died a year back and now he lived alone.
He offered to drive me home. I gave him my address and my number, something I had never done before. After he had dropped me off, I went to the nearest clothing store to buy a dozen jockstraps. Back home I shaved off my pubes. He wanted me completely hairless from the neck down. Thankfully I was naturally smooth and only had hair on my crotch and armpits. My asshole I kept shaved anyway. The next day I kept breakfast to a glass of juice. He had told me that while he liked that I was fit, (and I was by no means bulky) he preferred that I got leaner. I spent as much of the morning I could, checking myself out in my new jockstraps in front of the mirror, trying to imagine how I would look with a collar on. I couldn't help jacking off. I told myself I might not pick up when he calls. Then it was off to work. After my shift was over, I checked my phone first thing, saw his message and replied "yes". In his car, I confessed to jacking off. He smiled. Back in his suite, my poor ass received a thorough spanking. Over the course of the week, more rules, more punishment, more getting fucked and no jacking off (lesson learnt the hard way). When the week was over and he told me he had extended his stay for a month, I couldn't hide my joy. Soon I was wearing jockstraps full time, and he made me throw away all my other underwear. I was allowed to jack off only once a week, on Sunday mornings, wearing my jockstrap and cumming in it. When the month was over and he was about to leave, I was depressed. On the last day, he had made the offer. Since I was still new to this, he kept it to three years. During those three years, I would have no option of leaving. I wanted to be with him, so I said yes.
He had returned to Chicago and it had taken me two months to get my things in order. I told my family I would be volunteering in Africa and that I would be in touch only infrequently. My parents who had never managed to talk me out of anything didn't argue too much. I sold the remaining term on my apartment. Things I valued were sent back home. Everything else, including my clothes, was either sold off or given to charity. My buddy would run the restaurant in my absence and Master Nick's lawyers would check the books for me. I kept my jacking off to a regimental once a week. Kept a strict diet, and abstained from sex. It wasn't easy but I thought of Master and managed. As the day to leave approached, I grew more nervous but something kept me going. Finally I was on a plane heading to my Master. I wore a shirt, pants and jockstrap underneath. All I had was what was in my bag: a toothbrush, 6 jockstraps (I had found these online. they had ADDICTED in block letters on the strap. I had seen it in a lot of porn and had wanted them for a really long time), 4 white tank tops (wifebeaters), two pairs of brown shorts, a shaving kit and weighing 20 pounds less. Now that my plane was landing I was scared. I wanted to go back. I kept going. I accompanied the other passengers to the exit. And there I saw Master Nick waiting. He spotted me, smiled and nodded in approval. I realised that Master was like a magnet drawing me in.
AUTHORS NOTE: I didn't go into detail on the sexual relationship between the Master and the bitch that took place in New York. Rather I wanted to concentrate on the dynamics of the permament relationship that began once the boy was securely in his Master's possession, which I will be doing from the next chapter onwards. This is an email address I use exclusively for corresponding with Nifty, so I request all readers who have the time and liked the story to send me your thoughts and opinions. You can be assured of my full discretion.