Once a Bully, Always a Bully… Pt. 03

Another week had gone by and I was still getting degrading text messages from James. I did as I was instructed and wore the panties to work everyday. A part of me figured he wouldn't find out if I didn't, but it wasn't long before he randomly called to video chat me and make sure. I wasn't wearing them at the time, so I made up an excuse that I had just gotten out of the shower. Whether he believed me or not, I'm not sure, but it seemed like he was willing to let it slide. After getting that video call, I made sure I was always wearing them, and sure enough, he continued checking up on me from time-to-time to make sure. He was so persistent, he even made me send him pictures of the panties I was wearing under my clothes at work--I would sneak off to the bathroom so no one would see me obviously.

When I got home from work one night, there were several packages by my front door which I assumed were from James. He must've received an alert when they arrived, because he texted me soon after I got in the door, "you got the packages right?"

"Yes Daddy, thank you." I replied.

"Oh believe me faggot, you will be thanking me. Now you make sure to find some closet and drawer space for those. They were not cheap, and I won't have you throwing them in some random box in your closet."

I replied, "yes sir, I will."

He then responded with very precise instructions: "Now that you don't have to wear those dirty panties, I expect you to take this seriously and wear a different outfit every day. There are a variety of options for you and I want you fully dressed in the daytime. Before bed you can switch into some pajamas or a night gown, and on your days off I want you in one of the nicer outfits. Especially when I come over, I want you looking like you've got a date. In some ways, it is like a date, a date with my cock that is haha... There are lots of different wigs and shoes there for you too, but I don't expect you to put on stilettos and walk flawlessly. It's okay to start with the shorter heels, and you can work your way up from there. You'll also find a makeup set there too. Do some online research and find some tutorials. I ordered some other essentials to my place as well, but I'll be bringing those over in person. Until then, you need to start teaching yourself to be the sissy bitch that you are. So get to work, and I expect a picture of you ready for bed tonight."

I didn't know where to begin. I brought the boxes to my bedroom and slowly went through everything. To my surprise, he had bought several outfits. Most of them seemed to be very high quality too. I wasn't sure what James did for a living, but this was a clear indication to me that he must've been quite wealthy. Most of what he bought was either bright pink, lavender, or sky blue. Although there were some black, goth looking outfits as well that simply looked complicated and scary.

Since some pieces came separately, I had to do my best to figure out what all matched. Most of the bras and panties came as sets, so that helped. There were also a few packages with fully matching sets. I assumed those were the ones he wanted me to wear on my days off. I felt that a lot of what he picked was over the top. They weren't typical jeans and sweaters that I would see average women wearing. These were slutty and clearly meant to degrade me as much as possible. The bright colored outfits looked like clothing that a little girl would wear if she were pretending to be a princess or something. So basically a lot of stereotypical lolita style one-pieces with ruffle skirts.

I folded what needed folding and made space for them in my dresser drawers. Then I put the rest on hangers and organized them in my closet. One thing was for sure. I wasn't going to be having any friends over for a while, considering the risk that they saw what was in my closet.

Once I had finished putting everything away, I went through my drawers to find something to sleep in. I put on a lavender colored wireless bra, and some cotton, bikini style panties that looked like they wouldn't be too uncomfortable. The set had patterns of cartoon princesses on them. It was ridiculous, but I wasn't going to jump right into wearing thongs and full lingerie sets yet. I found a matching pair of thick cotton pajama pants, and a button up shirt that matched.

I obviously felt ridiculous, but I did as instructed and snapped a picture for him. Almost immediately he texted me back, "Aww, look at the little sissy princess? I don't know too many princesses with short hair though.., put a wig on and tried again."

I looked for a suitable wig and I found a simple one with long straight brown hair. It was probably the closest to how it would look if I grew my hair out anyway. I sent him a second picture, and he replied, "that's better. Now I know you don't go into work until the evening tomorrow, so when you wake up, I expect you to find a nice casual outfit to wear until then. Don't leave any accessories out either. I expect wigs, heels, and makeup every time. If I think you're being lazy or not taking this seriously, I won't hesitate to give that bottom another strapping, do I make myself clear?"

"Yes Daddy," I replied.

"Good girl, now get some sleep. You've got a long couple of weeks ahead of you; lots to learn."

My fears had basically come true, I was trapped, and there was no way out. I was kicking myself for not just letting him leak the videos. It wouldn't have looked good for him either obviously, but then again, who was to say it was even him in the video. Or maybe I should've just let him kick my ass and that would've been the end of our interaction. Either way, I was a coward and now I was dealing with the consequences. All I could do was hope that eventually he would get bored at some point and leave me alone. One thing was for sure, he was right about me being a pathetic little bitch. Any real man would've stood up for himself no matter how bad it was.

That night, I kept waking up from the discomfort of wearing a bra. I really started having sympathy for women and what it must be like to wear one all day. However, I couldn't help but think that the panties were quite comfortable. Something about the way they felt on my bare skin just felt natural.

I'm not sure if it was the clothes or the degrading texts, but I had dreams about him over and over again. In my dreams, I was blowing him in the living room, like before. Although for some reason, I was enjoying it. Every time I woke back up, I was erect and had to question why I was enjoying it in my dreams. Then again, it's not like we have full control in our dreams, so I did my best not to think about it.

The next morning, something happened that I could not comprehend. When I got out of bed, I felt a weird texture toward the front of my panties. I pulled the pajama bottoms down to check, and there was something wet and sticky. I peaked at my penis and it appeared as though I had a wet dream.

I quickly disrobed, threw the panties in the laundry basket, and hopped in the shower. I couldn't believe what had happened. The memory of the dreams I had suddenly came back to me, and I realized that I wasn't just enjoying it in my dreams. The feeling was real enough to cause me to ejaculate in my sleep. For whatever reason, this had concerned me more than anything. I had a pretty solid reason for doing all this dress up and sexual stuff for James. He was blackmailing me and I didn't have any choice, but having wet dreams about it was much harder to justify.

When I got out of the shower, I tried to clear my head and concentrate on my assignment. I had to find something to wear. I went through the drawers and picked out another simple pair of panties. These were all white satin with pink floral patterns and some ruffled lace on the elastic band. They came with a matching bra as well. Although the bra was wired and had thick padding where the breasts go; unlike the one I had on the night before which just fit flat across my chest.

In the closet, I grabbed a bright pink miniskirt that glistened against the light. Not knowing what to match it with, I looked at the tag and researched online what women were wearing with it, and did my best to find something similar. I had a simple white blouse that looked like it would work, and seeing as though most of the girls in the pictures had something covering their legs, I found a pair of white pantyhose to match the blouse. All that was left were the shoes and accessories. For the shoes, I went with bright pink suede open toe heels which were only an inch or so off the ground. I grabbed a different wig though. This one was shoulder length, blonde wavy hair, and a pink bow to match the skirt and heels.

I wasn't ready to send a pic yet though. I needed to make some attempt at putting on makeup. Just like he had said, there was an entire set of stuff. Lipstick was pretty easy to recognize, but I didn't have a clue what everything else was. I looked up some video tutorials for beginners. It seemed as though applying foundation and blush would be the hardest part, but also only seemed essential for dressing up. So I stuck with the basics: eyeliner, eyeshadow and lipstick.

The hard part wasn't necessarily the application of everything, it was the fact that I had to face myself in the mirror the whole time. Seeing myself go from a bearded, masculine looking man, to a smooth, feminine, and above all, promiscuous looking girl was a frightening sight. Another wave of shame hit me when I started applying the lipstick. I began feeling blood rushing to my penis, and seeing myself in the mirror like that was making me hard. I tried to tell myself that I was only feeling that way because the person I was looking at in the mirror was feminine.

After I was finished getting dressed, I snapped a couple pictures through the mirror, and sent them to him. He replied a few minutes later, "you see how natural that looks? Much more fitting for you than that beard, don't you think?"

"Yes Daddy," I replied.

Knowing the rules, I stayed in that outfit until the evening came and then I had to go to work. It took me a little time to get the makeup off my face, but after I got everything off, I stripped down with nothing but the panties on. Then I quickly threw on my work clothes, and headed out.

I periodically had to check the mirror while at work, as I kept getting nervous that maybe I had left some makeup on and someone would notice. It reminded me of when I was in high school, and tried to hide the alcohol on my breath when my parents came home.

That night, I came home late, threw the matching bra back on and a nightgown to cover up. I sent a pic to James, but it was so late, he was probably already asleep.

I went on with the routine for the rest of the week. I had a day off to practice with foundation and did some routine shaving to keep myself smooth. James was busy that day, but I knew that on my next day off he was planning to come over. He texted me two nights before, "I'll be over this Wednesday evening. I want you to pick out something seductive to wear. You wore bright girly colors last time. Maybe this time you should wear something dark and tight fitting. Show off that girly figure you have. And no need to send a picture, I'll check your progress when I arrive."

Wednesday came and even though I had until the evening, I made sure to get an early start on getting ready. I went through my closet and looked at my options. The first thing that stood out was a black and purple one piece corset with garter straps. I had seen these types of outfits in porn but never in person. There were a lot of clasps on it and it took me a while to get all of them connected. I had to start by connecting the clasps across my stomach. Then, I tightened the ribbon in the back and tied it tight, just like I saw in a tutorial. The breast cups were firm, which kind of made it look like I had breasts. I put on the matching lace thong that came with it, which felt so bare--having never worn a thong before. I found a pair black fishnet stockings which I pulled up over each leg, then clasped the garter strap on to hold them up. Over my lingerie, I put on a leather mini skirt with a black tutu built in underneath, and a black mesh blouse which I tucked into the skirt. The hardest part though was the shoes. Knee high boots which laced up to my knees. It took me forever to squeeze my foot in and tie up the laces. One thing was for sure, living as a girl was no easy task to master, and on top of that, I still had to do my makeup.

I felt like a goth chick by the time I had my face together. Dark eyeshadow and the darkest shade of purple lipstick I had available. Once the wig went on, I couldn't even recognize myself. I felt like I could go outside and no one would even recognize me. All of this I would've never been able to figure out without the internet.

I spent the rest of the day watching tv and waiting. My heart was beating hard and I was nervous. I knew that even if he was pleased with how I looked, he was still going to degrade and humiliate me. Either way, I kept checking to make sure I looked my best, as I certainly didn't want to get the belt again.

The evening came faster than I could expect and as I sat on the couch, dozing off, I heard a loud knock at the door.

To be continued...