For the next few days, I had to go to work with my new fittings. Not only was I worried about being caught with panties on, but I couldn't help but think that people were able to tell that I had some plastic device on my penis. I kept checking to make sure the bulge in my pants wasn't larger than normal.
The first couple times I had to remove the butt plug were difficult, but I was slowly learning to relax my anus so it didn't get so sore. However, I knew that I had to try out the dildo soon or James would get upset. I had been far too busy at work, but I was certain that he wouldn't want to hear any excuses. He had sent me some emails with links to videos, but I hadn't clicked them yet. I was getting off somewhat early one night though, so I figured that was as good a time as any to start practicing.
When I got home, I had removed my male clothes and went to my room to put something together. It had become routine for me to simply change into pajamas or a nightgown, but my intuition suggested I pick out something a little more intimate for a change.
There was a dark red bodysuit that I had been eyeballing for a few days that looked unique. Perhaps it was the latex material, or the fact that it was crotchless, but it made me tingle when I grabbed it. I imagined seeing another woman in it, but that wasn't quite why it made me tingle. Once I slipped it on, I realized the excitement was simply just wanting to feel it on my body. It actually made me feel sexy, which was starting to become a mild sensation the more and more I learned how to dress. I kind of wanted to get in full make up just to see, but it was already somewhat late. I just put a wig on and admired myself in the mirror for a moment. Most of my flesh was covered, except for my privates. So even though I was covered, I still felt completely exposed. I found it to be awkward that I liked the way I looked, so I quickly stepped away from the mirror and made my way to the bed with my laptop. I opened the emails, and clicked on the first link.
I assumed it was going to be something I didn't want to watch, but to my surprise, it was a woman in a sexy outfit, teasing the camera. She danced around for a minute, then started stripping. Just as she took off her bra, in place of her nipples, were those digital black censor bars. Then, when she removed her panties, the entire view of her crotch was blacked out, and written over it were the words, "Real men only. No beta sissies allowed." It became obvious why he was letting me watch it; it was a total tease. After watching her censored body move around, eventually a man came into the shot. As he approached her, she got on her knees, and reached for his pants to pull out his cock. Of course, the penis wasn't censored at all, and it had an arrow pointing to it, which read "focus on the cock sissy."
I accepted it as it was, an obvious prank, but yet it still aroused me in some way. The instructions in the video were to think about the woman in a sense that I was her, and the only reason I should look at her was to observe and take note as to how she pleased him. About half way in, the instruction came in to grab a dildo and practice.
I embraced it for what it was, and followed the instructions. At this point I was beginning to follow all of his other instructions anyway. I went into my dresser drawer and grabbed the dildo he gave me. It wasn't as large as James' penis luckily, and I was thankful for that, as he clearly showed me some mercy there.
The video continued on and kept becoming more and more focused on the guy's penis. Eventually, he starts to penetrate her from behind. I removed the butt plug, set it aside, then I took the lube that James left with me and started coating the dildo. My anxiety was slowly increasing as I considered what it was I was about to do. Eventually though, I caught my breath and began to slowly push the tip of the dildo in. At first it felt like the plug, but that changed when I got to where the dildo had more girth. I had to pull back a few times and allow myself to relax again. Everytime I pushed it back in I got further and further, eventually surpassing the length of plug I had been using. Then something changed, I felt a strong pressure once it was about six inches in; almost as though something was stopping it. It was weird, but I had a slightly pleasurable sensation from it. After a few back and forth motions, I caught myself starting to moan a little. It was mostly from the pain, but it was painful in a different sense.
The video had instructions for me while I did it. These were motivational messages like "keep going" and "faster sissy." After about five minutes, the man in the video pulled out and came on her face. He pulled up his pants as he was clearly done, but she laid there shaking and covered in cum. As I finished with the dildo and removed it for good, I could slightly understand her position. She was stretched out, numb, and so was I. I also couldn't help but feel a sense of relief, like I had accomplished something.
The question came to me: if penetrating myself with the dildo he gave me was that intense, then how bad was it going to be with his massive cock, and him controlling the movements? I knew I needed more practice. Over the next week, whenever I had the chance, I played with the dildo to prepare for the real thing. I tried everything from laying in different positions to pushing it up against the wall or moving up and down on it. I had to be ready for any amount of thrust or any position he might try.
Since James had left the previous time without saying much or discussing a future date, I didn't have any idea of when I'd see him next. I figured I should be prepared to see him on my next day off because that was the trend, but that wasn't really how it ended up happening that week. I got a text from him one evening after work which read: "Sissy, in five minutes I am going to video call you to make sure everything is going well, and I better not have to call twice." I was already in my pajamas and getting into something fancier wasn't possible in that amount of time, so I quickly threw on a wig, sat up on my bed, and waited.
Just as promised, I got the notification on my phone that he was requesting to video chat, so I picked up. "Hi Daddy," I nervously said as the camera came into view.
Before he spoke back, I could see that other people were at his place. It looked like a few guys and one girl. The girl was on her knees in front of the guys, but that's all I could make out before he changed the angle of the camera, and spoke. "Well hello there faggot. Look at you all ready for bed in your ditsy onesie. I just wanted to make sure my new little sissy was behaving herself. Have you been doing everything I asked?"
"Yes Daddy," I responded. "I've been wearing the plug all week and I've been watching the videos while playing with the dildo you bought me."
"And the chastity device," he asked, "Is that fitting okay?"
I answered, "I think so, but it's a bit uncomfortable and restricting."
"Well that's just a part of life you're going to have to get used to... Anyways, let Daddy have a look."
The onesie pajamas I was wearing was totally closed in except for a flap on the butt that was held together with some snaps. My assumption was that it was for faster bathroom access, but he probably bought it for me because of the access to my privates. I had to pull my penis through my legs to show him that the device was still on, and I spread my cheeks to prove to him that the plug was currently in.
"Hmmm, very well" he responded after he had seen everything. "Keep up the practice and get some beauty sleep. Oh, and dream of cock!" He said the last part loud and I could hear laughing in the background. He hung up a few seconds later.
I went to bed but the next morning I woke up to my phone ringing. I answered it in my groggy morning voice, "hello?"
There was a pause, and then I heard James' voice, "Ummm, I think you mean hello Daddy, and fix that deep voice."
