Once a Bully, Always a Bully… Pt. 05

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."

I tried again in a girly voice, "Sorry, hello Daddy,"

"That's better." he said and then went into why he was calling. "I have to go to some stupid work thing later and I think I could use a little release from my cocksucking sissy. I'll be over in ten minutes."

I freaked out as it was such short notice and on a work day. "But Daddy," I replied. "I'm still in my pajamas and it's also a work day for me."

"First off, I don't want to hear any excuses, and I'm not an idiot; I know you have work. There's no need for you to change out of your pajamas, I'm just dropping by for a few minutes. I need you to empty these balls real quick and I'll be on my way. You still have a couple hours, and I only need about ten to twenty minutes. Unlock the door and wait in your bedroom."

I nervously went and checked myself in the mirror to make sure I looked half decent. Then I did as he asked, and unlocked the door. I laid on my bed and waited about ten minutes before I heard the door knob twist and open. A few seconds later he walked into my bedroom. I started to get up as I assumed he wanted me on my knees in front of him, but he stopped me and pointed at the bed. "Stay there," he said. "turn over on your side and face the wall."

I turned into a sideways sleeping position with nothing but the wall next to my bed in sight. I heard him unbuckle his belt to take his pants off. In nothing but boxers and a t-shirt, he crawled into bed and began spooning me from behind. It wasn't an intimate spoon, however. Instead of his hand over my chest, he rested his hand on my hips, gripping the side of my buttcheek. A moment later, I started to feel his bulge resting between my buttcheeks. It was separated by both his boxers and my pajamas, but it was clearly growing harder and fighting to pass the barrier between us. As his penis grew, he started grinding on me a little bit, and with each thrust, he would use my hip bone to pull my body towards him. "Do you like the feeling of that cock pushing against your ass?" he asked.

"Yes Daddy," I replied.

"I bet you do, faggot. I want you to show me though. Press your ass against it and start grinding on it."

I arched my back and began rubbing my ass on his bulge, back and forth. He held still but I could feel that his penis was rock hard.

"Flip onto your stomach," he demanded.

"Okay Daddy," I nervously replied as I turned facing down.

He got up and sat over top of my legs, pinning me down. His hands were moving towards my ass and then I heard the snaps on my pajamas being unbuttoned. He pulled the flap on my pajamas down, exposing my ass and the pair of panties I was wearing. I started to shiver as I couldn't figure out his intentions, and my anxiety became much worse when he pulled my panties down just below my butt. After looking at my smooth bottom for a moment, he reached for my ass and spread my cheeks apart, exposing the jeweled stem of the butt plug I was wearing. He slowly pulled the plug out and set it down on my nightstand.

I began to panic and he had certainly noticed me shaking and clenching uncontrollably. I felt his finger lightly circling around the rosebud of my hole. Shortly after, both of his hands grabbed onto my hips and I felt something soft graze the outside of my hole. I couldn't figure out what it was at first, but then it pushed a little harder towards my hole and I quickly came to the realization that it was the tip of his penis poking me.

What followed next was a regrettable mistake on my part. I wasn't ready to feel his penis against my hole; not mentally or physically. My nerve endings registered it as a danger and I quickly moved my butt away from him, pulled my panties up, and spun back around facing him. I cried out "no no no no no! no way!!!"

I was abruptly cut off and silenced by a hard slap across my face. "What the fuck did you just say to me you little bitch?" he shouted.

The whole left side of my face had turned red and stung from the slap. Needless to say, I couldn't answer the question. He cocked his hand back again, but I quickly put together some words. "I'm sorry Daddy, I can't, I'm not ready. I swear I've been practicing, but I'm just not ready."

"What did I tell you about alpha males?" he asked.

I replied with my best guess, "that they don't care if I'm ready?"

"No, they don't care if you're ready, and they don't care if it hurts."

"I know, I'm sorry Daddy, just please, I need more time."

He paused to think, then responded in an annoyed tone, "I wasn't planning on penetrating you today. I was just going to poke around for a little fun. You see, unlike some selfish daddies out there, I take good care of my sissies. I was planning on giving you another week to get ready, and I'm still going to give you another week, because I'm a caring daddy. However, I do not tolerate disobedience, and I've warned you before what happens when you say 'no' to me. So climb down off the bed and get on the floor, on your hands and knees."

I did as he said and got down on my hands and knees. I was relieved to hear him say that he wasn't going to penetrate me, but I had yet to put together why he wanted me on my hands and knees. Usually getting down on my knees meant I was probably about to suck his dick, but he was not happy with me, and I wasn't expecting what happened next to be as manageable as sucking cock.

"Crawl over to my pants like a sissy dog and fetch me my belt," he ordered as he pointed to his pants on the other side of the room.

I realized what was happening, as I knew exactly what fetching the belt meant. He was planning on spanking me, and remembering how much it hurt the first time he spanked me, my stomach sank and I immediately turned red with fear. I quickly turned back towards him and I tried to beg my way out of it. "Please Daddy, please don't hit me with the belt. I promise I'll never say no again. It was a mistake Daddy, you just caught me off guard is all. I promise, you can play with my hole, I don't mind. Just please don't spank me."

Before I could say another word, I started seeing stars. His hand struck me hard across the face again. He grabbed my neck, nearly choking me, and turned my face towards his, shouting loudly, "I said to crawl on your fucking knees and fetch the goddamn belt!!!"

With his hand on my neck, he shoved me towards the floor. I stumbled for a moment then caught myself. So I slowly crawled on all fours over to his pants. It was probably a mix of the stinging sensation on my face and the intensified fear of what was to come, but I started to cry. I made no attempt to hide it either. He had already seen me for the coward that I was, and the thought of proving any form of masculinity to him was no longer something I was concerned with. Like a child, I let out my tears and cried enough that he would notice. I thought that maybe I could draw out some sympathy from him. He was sincere though, and I could tell that neither my words or tears were going to change anything.

I began pulling the belt from the loops in his jeans. I held it in my hand for a moment and then he gave me another order, "fold it half." So I did. "Good, now put the middle of it in your mouth and bite down; just like a dog bone. That is how a bad sissy should always carry Daddy's belt.

I placed the center of the belt between my lips and bit down. "Now leave the belt in your mouth, get back on your hands and knees and crawl over to me," he commanded while pointing between his legs.

I slowly made my way back towards him, holding the belt tight between my lips. I stopped right between his legs and looked up. He signaled for me to drop it onto his lap, where his hands were. I let go and the belt fell right where he wanted it. I made one last attempt for mercy. I looked him in the eyes and cried out loud while my lips quivered.

As if he didn't even notice my cries, he turned to the side, grabbed my pillows and stacked them on top of each other at the edge of the bed. "Stand up," he said, and as I stood up, so did he. "face the bed, and bend over the pillows,"

"Yes Daddy," I replied, and did as I was told. My body was perfectly arched with my feet on the floor, my elbows on the bed, and my bottom boosted into the air by the pillows underneath.

He cracked the belt in the air a few times and leaned in towards me to say, "I told you what was going to happen if you said the word 'no.' I warned you about the consequences of disobeying me. Now you're going to get a well deserved spanking, and I'm going to make sure that this one delivers whatever message wasn't received the first time I took the belt to your backside. Now hold still, keep your feet planted and your ass in the air, understood?

"Yes Daddy," I whimpered.

A quick "whoosh" followed by a loud "crack" filled the air as he landed the first stroke on my bottom. I yelled out as my legs quivered, but before I could regain my composure, he laid down another. I quickly started crying like a child again as he continued, stroke after stroke.

Several minutes had gone by and the strokes were getting more intense, as he kept hitting the same spot multiple times. It became too difficult for me to keep still and after one really hard smack, I rolled over onto the bed. "Hold still damnit!" he yelled.

I cried out, "I can't, it hurts too much Daddy."

He paused for a moment. "You will learn to hold still for your spankings. It's only going to hurt more if you don't. Now if you roll over again, I will just keep going."

I got back over the pillows, and I tried to obey his order, but I couldn't help my reaction to the sting of his belt. I rolled over again, and as promised, he continued. I felt the belt come down hard on my hip. I foolishly put my hand out to protect myself but then the belt landed on my knuckles. Both were much worse than the feeling of it hitting my butt, so I rolled back onto the pillows, getting back just in time for the next stroke on my bottom.

"I told you, it's best to stay still," he said with pride, as he was conditioning me not to resist. Although, even after that painful stroke on my hip and knuckles, he once again landed an extra hard blow on an already marked up spot, and I rolled off the pillows again, but I knew better that time and quickly fought to get back up. He did make contact with the side of my thigh that time, which wasn't as bad, but it still stung like crazy. "Look at that, she's learning," he said.

As much as I fought to stay still with my stomach on the pillows, I just kept throwing myself off, and even though I was good about getting back up, he became annoyed. So with his left hand, he grabbed me by the wrist and held my arm behind my back, pinning my face down on the bed. Then, he placed his right leg over my legs, locking my legs in place. Tilting my body slightly on its side, he held me down and strapped me as hard and fast as he could. I screamed into the covers, which muffled my voice, but it was loud enough in my head that I could hardly even hear the belt hitting my bottom. He continued like that for about two minutes, and eventually lost his energy. After a few more light swats, finally, he set the belt down.

I laid there still pinned down. He waited until my screams turned back into soft cries. Then as my eyes cleared enough to see him again, he pointed to the other side of the room. "Go stand in the corner now and think about what you've done. I will expect a well thought out apology in a minute, but for now, you will stay quiet and face the corner."

I stood up slowly, walked over to the corner of the room, and stood facing the wall. He took a few pictures of me in the corner with my bottom all marked up. I had not seen it yet, but I was certain it was going to be welted.

After taking the photos he put the phone down and came up behind me. "Are you ready to apologize now?" he asked.