Riley Gendreau
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Forced to Crossdress: Pt8 (Ea)
🕑 Added 2025-07-03 02:53:58 +0000 UTCMy name is Bryce Cooper, and yesterday was the first day of my temporary job as a maid, and it went even better than I could imagine. Sure it was a lot of work cleaning, but I turned out to be quite the gifted maid.
Cindy, on the other hand, was the exact opposite; her hands may be amazing when it comes to doing hair and makeup, but when it comes to cleaning, they are the last pair you want to ask to step in and lend a hand.
Luckily, Bentley has a lot of patience and is working with her, or perhaps I’m so good that I make up for what she lacks; either way, we’re making it work. After cleaning all day, the master of the house's daughter arrived home from school.
I had no idea who she was at first, but after being dragged to her room and teased a bit, it turned out to be Leo, my partner. They then explained a bit about what was going on. They pretend to be a girl in order to keep their annoying family off their backs.
So basically they’re forced to cross-dress as well. Who knew we had so much in common? We talked some more while they bathed, though I was facing away the whole time, and I ended up explaining why I was here in a maid uniform.
They found it funny but were happy for Cindy working hard to make her dreams come true. They were also happy that I was here, as they hated being home, and now instead of an annoying older maid, they had me.
After their bath, they got into a nightgown, which was super pretty and made them look like a princess, though they didn’t seem to like it, but they didn’t let it get to them and instead made a joke about how cute I’d look in it.
I turned a bit red, which made them laugh at me, but at least they were laughing, and I was making being here bearable for them. We talked some more as they got another long black wig on, and that’s when they suddenly stopped and asked me a favor.
As glad as they were I was here, they didn’t want me to reveal anything to Bentley or their family members should they decide to show up. So while I’m here, they need me to call them Leah and use she/her pronouns when referring to them.
They said it would be annoying, but it kept the peace, and we could go back to normal once we were back at school. I closed my eyes and thought about it. I mean, it’s what they want, but I still don’t like the idea of using their deadname and the wrong pronouns.
However, not everyone has a family that they can be open and safe around, so I understand. So seeing as it was what they… I mean she… wanted, I was going to do it. I gave her a curtsy and said, As my mistress commanded, which made her laugh.
Leah got up and kissed me on the cheek, thanking me for this and for somehow getting hired and being here this week. She then walked towards the door to head downstairs, and I followed closely behind her.
We got downstairs, where Bentley was scolding Cindy for somehow filling the teapot with dishwater, but stopped when he noticed us. He told Leah she looked lovely and told her that her meal and tea were ready and she could go start enjoying them.
Leah thanked him and left us. Bentley then told us that we were done for the night, but we were to show up nice and early the next day. We both nodded and said goodbye, then we headed home. Once I was home and undressed, I passed right out.
The next morning came quickly, and we made it to the mansion as instructed. I expected to be doing more cleaning today, but Bentley informed me that Leah had requested that I be the one to assist her today. He then warned me that she could be difficult and not to let her get to me.
I thanked him for the warning and told him I would be alright. He was happy to know I wasn’t put off by his warning, then handed me a silver tray filled with food and drinks. He told me to take this up to her, which I did promptly.
I knocked on the door but got no response, so I just let myself in, which I wasn't sure about at first, but when I found Leah sound asleep, I knew it was okay. I place the tray down on the table next to her bed and look at her.
She sure didn’t sleep like a prim and proper girl, which makes sense, as she’s not actually a girl. She was not only lying the wrong way across the bed, but her blanket was only covering her head, and she was snoring super loudly; it was honestly adorable.
I walk over to the blanket and pull it from her head and try to wake her up. She just mumbles something about me going away, then calls me Bentley. I shake my head and turn around. I grab the curtains to her room and pull them right open.
Suddenly her face was covered in sunlight, which was enough to wake her up. She started moving and groaning as she did. She sat up with a frown on her face, but that changed when they realized I was here.
She said good morning to me as she stretched, then she started to sniff the air. She followed the smell to the food next to her. She said it looked great and was about to reach over and grab something, but she stopped and turned back towards me with a big smile on her face.
She clapped her hands and asked me to come over and feed her. I tilt my head and ask if she’s serious. She nods and says she didn’t feel like it, so it was a good thing her family hired help so she didn’t have to.
I smile while shaking my head and make my way over to her. I pick up the bowl of berries and a fork, then I walk over to her. She pats the bed and tells me to sit next to her, then she opens her mouth so I can stuff it with food.
I begin to give her bite after bite, and she smiles and hums a happy tune as she chews. Once the berries were mostly gone, Leah tells me she’s thirsty now. I don’t even question it and get up to grab her something.
I asked her if she wanted chocolate milk, orange juice, or tea. She tells me the tea is fine, but I could see out of the corner of my eye that her face didn’t reflect that it was true. So I looked at the orange juice and chocolate milk.
Leah doesn’t normally come off as liking things like chocolate milk, perhaps because they don’t like being seen as some sort of kid, but it’s chocolate milk—who cares? So I decided that’s what she was getting, and hopefully I’m right.
I bring it over and press it against her lips and raise the cup so she can sip. She seemed quite surprised at first, but I could tell from her eyes that she was happy with what I picked. Of course, she was still going to tease me about it.
She said I was a bad maid for not listening, but she’d forgive me this one time, but if I do it again, she might have to punish me. I turn bright red as I wonder what she means by that. As much as I’d like to find out, perhaps doing so here wasn’t a good idea.
I got to give her another sip, but she took the cup from my hands and told me that she had enough fun and could finish on her own. I nod and get off her bed to let her do so. That left me standing there awkwardly watching her.
She noticed me and said it was quite embarrassing to have me here watching her eat, so she was going to give me something to do while I waited for her to finish her breakfast. I nod and ask how I could be of service.
Leah asked me to head to the closet and pick out a dress for her to wear today. I nod and tell her I’d pick out a nice one, then head over to the closet door and open it, and seconds later my jaw nearly dropped to the floor.
Her closet was massive, not just like the side of a room, but the size of my entire house, and it was completely stuffed with different, very colorful dresses. All different lengths and types, so many that I wasn’t even sure it was possible for one person to wear them all.
I look at Leah and ask if there was something specific I should grab. She sighed while putting her hands up. She told me she hated everything inside the closet, but her family annoyed her less when she wore something long and bright.
Not sure why that is, but at least I have something to work with when I head inside, and hopefully I don’t get lost. I walked a few feet inside and started looking at what was there, and not a single item looked like something Leah, the real Leah, that being Leo, would wear.
Normally Leo wore darker colors and dressed in either goth or punk attire, or at the very least a simple black shirt and shorts. the stuff inside here was nothing like that, the complete opposite; it was more like stuff I would wear… Not that I would, of course…
What kind of guy would want to wear any of these beautiful dresses? I say as I look down at my maid uniform. Either way, these are for Leah, and it really sucks, as I know she doesn’t want to wear any of them.
Comments
Riley
It was mentioned a bit in the last part, but yeah, I made Bryce naturally amazing at being a maid. Along with that, not that I'm saying anything about what's to come, but Bryce also has the natural skills of a mother as well. C:
last_of_workers
I'm impressed... I really didn't expect Bryce to be such a good personal maid. It's really impressive.
