Forced to Crossdress: Pt10 (Ea)

My name is Bryce Cooper, and today was intense. After the events of this morning with Leah and that dress, I escorted Leah outside to the flower garden so that she could have her photo taken. I thought it was only going to be one photo, but it turned out to be hundreds.

Worse than that, I had to help the photographers set up every shot by moving things around, among many other things, all while Leah only had to stand there and pretend to look happy to be here having her photo taken.

Once that was done, it was time for a tea break, so Bentley had Cindy and I in the kitchen making treats by hand. Well, it was both of us, but Cindy somehow made a complete mess of herself and the kitchen where she was working.

So she got put on dish duty, while Bentley and I worked on the treats. Once we pulled the treats out of the oven, Bentley patted me on the head and said I did a great job, and he was really impressed with how well and quickly I was picking things up.

His hand on my head and his kind praise made me feel warm inside. It was so strange; I’d never felt this way before. He was happy with my work, almost like he was proud of it, and I was happy to be helping him.

I wonder if this was what it would have been like to bake treats with my mother… I shook my head and put those thoughts away. No idea why I was thinking of that now. We got the treats and tea on a platter, and Bentley told me he trusted me to take it out to Leah and serve her.

I nodded and said I had it covered, then I grabbed the tray and brought it out. As I left, I heard Bentley start to scold Cindy, followed by her whispering for me to come back and save her, but that was something I couldn't do.

After serving Leah and chatting for a bit while she enjoyed her tea and snacks, I brought everything back inside. I stored the rest of the treats in a container, then I gave the dirty dishes to Cindy. After that I went back to Leah and stayed by her side as she continued to do things.

Eventually it came time for Bentley to drive her to an event, one I luckily didn’t get dragged along to. Instead, I was given a list of chores for me and Cindy to complete, and Bentley put me in charge of making sure they got done.

As they left, I curtsied and wished them safe travels, which got a smile from everyone—Bentley, Cindy, and Leah. Once they were gone, Cindy and I got to work on the chores; well, I mostly did while Cindy tried and continued to do poorly, but it was okay.

I didn’t mind picking up the slack, especially knowing I’d be getting a ton of new clothes once this was over, which I used to cheer her up when she started complaining about how bad this job was. That got her going on about all the clothes she was going to make.

She mentioned some cosplays, some dresses, and even a bikini she had in mind, all of which her model was going to test out. I wasn’t paying a whole lot of attention until she said that, and I asked her who she had in mind to be her model.

She looked at me confused and asked who I thought it would be. I had no idea at first, but to be fair, I actually thought she had someone else in mind. It turned out that wasn’t the case, and her model was in fact supposed to be me.

She shook her head and called me an idiot and said I was basically her partner now, and through thick or thin, we were in this together. I turned bright red and said while I didn’t mind modeling cosplays and stuff, there was no way I could wear a bikini.

She looked at me and asked why. I look away awkwardly and then point at my crotch and tell her it's because of the thing. She tries not to laugh and agrees that the thing could be a problem for a bikini, but she’s been thinking of a plan for that, so I shouldn’t worry.

I look at her, now a bit more worried because she’s been thinking of a plan for what? To get rid of it? It doesn’t just come off, but I really didn’t want to talk about it anymore, so I didn’t ask and instead kept cleaning and letting her talk.

A couple of hours later, we managed to get everything on the list done. So we took a small break as we waited for Bentley and Leah to get home. When the car pulled up, we went and waited by the door for them to enter, and that’s when things got a bit crazy.

Leah came storming in, so angry that she didn’t even notice Cindy and me. She ran right up the stairs and went to her bedroom. Then seconds later a man who looked similar to Leah walked inside, yelling that she was acting like a child.

He then stopped and looked at us. He seemed surprised, then looked towards Bentley and asked who we were. Bentley responded by giving him our names and explaining we were the temporary maids hired for while they were home.

The man pointed out how we were much younger than the normal maids. Bentley nodded and said there weren't many applications this year. The man rolled his eyes and blamed Leah for that because of how difficult she was.

The man then took my hand in his and then kissed it. I turned bright red and had no idea what was happening. He then told me his name, which was Sebastian, and that he was Leah’s older brother. He then started telling me I was extremely pretty.

I had no idea what to say or do, and Cindy wasn’t helping; she was just standing there watching, holding back laughter. Luckily Bentley came to my rescue and reminded Sebastian that some of the maids refused to come back because he was always hitting on them.

Sebastian shook his head and turned towards Bentley and started to go off on a rant about how he couldn't ignore his heart and that the fine maidens he comes across always seem to steal it, and he had to pursue them in order to reclaim it.

Benley didn’t seem fazed and asked Sebastian to go to his room and get ready for dinner. Sebastian shook his head and said a man with no family could never understand the magic of love. Bentley didn’t seem to let it get to him, but it sort of got to me.

He didn’t have anyone? No partner, no kids? That sounded lonely. I mean, I lost my mother at a young age and never met my father, but at least I still have my grandparents, even if I haven’t seen them in a year and a half since they started traveling the world.

I couldn’t imagine having no one and then having to take care of such a spoiled brat. Hearing him say that to Bentley made me grind my teeth and want to call him out. As I was sitting there listening to Sebastian say more and more things as he went to his room, I noticed Bentley looking at me.

Once the door was closed, he smiled at me and told me not to worry. He then said that we did good and that we were okay to leave for the night. He then warned us to get some decent sleep, as the siblings would be quite the handful.

Cindy and I nodded, and we were about to leave, but Bentley asked me to wait for a moment, so I did. He then left and came back holding the container of snacks I packed away earlier and a bag. He told me that Leah and Sebastian wouldn’t eat them, so I might as well take the snacks.

He then placed it in my hands and then showed me the bag. He said that it was a gift from Leah; he was unsure why, as she didn’t normally give gifts, but if he had to guess, it might have something to do with me removing my uniform earlier.

My mouth fell open, and I was so embarrassed. I started stuttering and panicking, trying to think of an excuse, but Bentley put his hand on my head and said it was alright. He told me not to tell, but he was well aware of Leo and what they liked.

I was now left speechless, not knowing what to do or say. Bentley finished up by saying he was happy I was able to make her enjoy being home for once, and he was really glad to have hired me and Cindy, despite her lacking any skills useful for a maid other than sewing.

He then told me to have a goodnight and walked me out. Still speechless and processing things, I made my way to the car, wondering how Bentley knew about me getting undressed. Then it hit me: I left my uniform on the bed, and he likely saw it.

Once I was in the car, Cindy asked me what Bentley wanted and about the stuff in my hands. I then gave Cindy the snacks and told her they were given to us because the siblings wouldn’t eat them, and then I explained that the bag was a gift from Leah.

I opened the bag and saw something yellow inside. I grab it and pull it out; it turned out to be the dress Leah had me wearing. The same one that made her cry. Also inside was a note written by her, and on it, it asked that I wear it again, perhaps when we’re able to go on our next date.

I smile and put them both in the bag. I still have no idea what is up with this dress, but if Leo wants me to have it and wear it, there must be a reason. So I’ll accept this clearly important gift, and I’ll wear it whenever they want, as long as it makes them happy.