Over the next few weeks, we had near-nightly "training sessions" that were similar to the first one. James would send me a text in the evening and instruct me to set up my room to his liking, lighting and all. I would ride the rubber fuck stick while he provided reassurance and instructions over the phone. He had me practicing during the day too when he wasn't home. He even got me to do it in the bathroom at my office. I always had to send photo proof.
Every so often, I would wake up to a box at my front door that contained a new, slightly larger toy. The last one was so big that it took me a while just to get the head inside for the first time. I received a few more pictures from him over that time but they never included his entire dick. Don't get me wrong. What he sent me was still incredibly hot but it was killing me slowly not being able to see him, completely, in the flesh.
We ran into each other on numerous occasions and typically talked about normal day-to-day things. He would always make suggestive comments here and there. I noticed that he would never touch me. Sometimes, he'd even go out of his way not to. It was endlessly frustrating. I think he was doing it to get a reaction out of me. He always cracked a smile when he saw my shorts or pants tent up around him.
I woke up one morning to a text from James that said, "I have to go to New York for a business trip. I'll be back at the end of the week. You will send me a video of you using dildo #3 tomorrow -- more instructions on that tomorrow. After that you will rest your ass I get back. You've got a big weekend ahead of you. Rest up"
My morning wood jumped a bit when I read the end of his text. I was desperately hoping this would finally be the week that he takes me for real. I couldn't wait to feel him inside of me. I also didn't know if I was physically capable of going up to a larger size dildo so I was also hoping this was the end of training for my hole's sake.
That night, after a monotonous day at work, I lay in bed with the curtains wide open wishing James was in the building next door giving me directions to get off in front of him. I realized that tonight was the first night he didn't specifically forbid me from masturbating. Every previous night that we hadn't had a training session he forbade me from getting off. He wanted me to save it for the following night. The curtains were to be opened at all times. To keep me accountable.
My dick was hard and leaking while I scrolled through my personal collection of photos of James. I started slowly stroking as I studied this immaculate man. His hairy, built chest looked like the perfect place to hold on while he railed me. His abs would flex and constrict with each powerful thrust of his hips, I imagined. That thick cock with its uncut head plowing me into oblivion until he spilled his plentiful seed into my willing hole. I scrolled to the photo of him smiling with cum splattered over his face. I imagined him fucking me, missionary style, and me jacking myself to completion only to recover and look up to see that handsome face smiling back at me, covered in the cum he had just fucked out of me. That did it for me and I blasted an ample load onto my abs and chest. I wanted to send a picture to James and show him what he did to me but I was never to contact him without being contacted by him first.
***
The following day arrived and passed, just as uneventfully as the day prior. I knew that night I would be making a video for James so I cleaned up well in the shower and even trimmed the hairs around my ass and taint. I wanted him to have the best view. I had just finished drying off when my phone pinged.
"Read the following instructions carefully. You will place your phone on the kitchen counter, screen up, with the camera overhanging the edge of the counter to record yourself. Below that, you will attach dildo #3 to the cabinet using the suction cup. Using your laptop's webcam, you will also record yourself from the side. Place the laptop on the floor, to your left, and make sure the screen is angled so that it captures everything, including your face. Fuck yourself to completion, taking however long you wish, and send me both videos. Neither will be shared with or showed to anyone without your explicit approval."
I was standing there in the bathroom, naked as the day I was born, still holding my towel in my hand. My dick was rock hard. This was getting so hot and I couldn't wait to record myself for him. I really felt at ease with him and that I could trust him. I knew he wouldn't show anyone without asking. He was dominant and assertive but gentle, kind, and respectful at the same time.
I quickly gathered everything I'd need and ran downstairs to set up. I was very eager to please him and wanted everything to be perfect. I ended up making a short recording to make sure I had the angles right, quickly finding out I needed padding for my knees. I threw down a folded blanket and once everything was set, I lubed up the dildo and hit record on both my phone and laptop.
I inched my way back onto the thick dildo #3, feeling it pry me open. Even after using this one several times already I still had trouble initially. Eventually, the head popped in and I moaned loudly in response. The pressure stretching my ring set off a cascade of electricity in my body. My erect penis jumped up and down at the sensation and I began leaking onto the blanket below me.
I started by making minor movements in and out, only taking in a few inches at a time and then coming back out although not completely. I continued this for several minutes, moving down by about an inch each time as I felt my ass relax. The entire time I hadn't even touched my dick and it was now flowing a steady stream of precum. I knew the second I touched myself I'd blow my load instantly. I wanted it to last and looked over at my computer screen to see how long I'd been recording -- 4 minutes, 36 seconds.
"Damn, I need to work on my stamina," I thought silently.
While looking at the computer screen I saw myself fucking my ass back onto the large dildo, my hard cock bouncing with each thrust. My arms looked defined supporting me up like that on my hands and knees and my ass jiggled with each plunge onto the thick pole. I arched my back and the new direction of the dildo pushed it hard against my prostate. I moaned loudly and knew I was getting close without touching my dick.
Ever since James had been training me I was experiencing hands-free orgasms quite regularly. Before him, I'd never had one so it was a thrilling new addition to my sex life. I don't know if it was the fact that he made me so horny and forced me to delay orgasm, save it up, and ride the edge or if the thrill of exhibitionism was the secret, but I was happy for whatever was making it happen.