Riley Gendreau
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Forced to Crossdress: Pt9 (Ea)
🕑 Added 2025-07-03 02:54:32 +0000 UTCMy name is Bryce Cooper, and I just walked through a closet door and ended up in a wonderland of pretty dresses… I mean… It’s a big closet of girly dresses. Who would like such a thing? Anyway, this week I’m working as a maid, and for none other than my partner, Leo.
Well, right now I have to call them Leah and use she/her to refer to her because of the dynamic with her butler Bentley and the rest of her family, which I hate doing because I know they don’t like it, but they asked me to do it, so for now I’ll play along to keep them safe.
Anyway, I was just feeding them… I mean her breakfast, but she decided to eat on her own, so she sent me into her closet to find something for her to wear for the day. They didn’t really have a preference on what I picked, which made sense.
There were so many dresses in here; I have no idea how one person could even remember them all. Heck, there were so many that I wasn’t sure what to pick, even with the suggestions Leah gave me for picking one out.
I was overwhelmed with the options to pick from, and I just found myself looking through each thing and slowly walking more and more into the closet. They were all beautiful, but none of them really felt like Leo… Leah…
I told myself to just grab one and leave, but a part of me was curious to see how deep the closet was and to continue looking at all the pretty dresses… not that I’m into them… though I may be more into them than Leah.
I mean, she never wears stuff like this, and even when she wore a dress, it was black. After some time digging around, I made it to the end of the closet. Having reached the end of the line, I tell myself to just pick one.
I look at the rack in front of me and look at the dresses. A bright yellow dress catches my attention, and I pull it out. Nothing about it was special as far as I could tell, and it wasn’t as fancy as the rest of the dresses, but I got a warm feeling from it, so I chose it.
I took it off the hanger and folded it over my arm, then I started to make my way out of the closet, which literally took over a minute, which is crazy. As I reach the exit, I make it back in time to see Leah coming out of the bathroom.
She sees me and smiles, then runs over and asks me what took so long. I sigh and say there were a lot of dresses in there, so many I could get lost. Leah chuckles and says I would feel that way in a room filled with pretty dresses.
I turn red and tell her that’s not what I meant; she rolls her eyes and moves on by asking me what I picked out for her to wear. I told her it was a normal-looking yellow dress. I then took it off my arm and held it up for her to see.
I was expecting some comment about how ugly it was, or perhaps how good it would look on me, but Leah didn’t say anything. She was just staring at it while her hand was over her heart. I think she may even have started to breathe heavier.
Something was clearly wrong, something serious. I apologized for picking this one and said I’d put it back and pick another. Leah still didn’t say anything but gave me a slight nod. So I turned around to get this thing away from her as soon as possible.
I was about to head back to the closet, but I was suddenly stopped when Leah grabbed my wrist. I turned to face her and saw that she had tears in her eyes. I asked her if she was okay, and she just looked down while still holding my wrist.
After a minute, she said that she couldn’t bring herself to wear the dress, but she’d like to see it worn. I was a bit confused about that, but then I think I understood what she meant. I asked her if she wanted me to put it on. Leah nodded and asked if that was okay.
I smile and tell her if it’s what she wants, then this simple maid shall fulfill her wish. I then walk over to the bed and place the dress down. I then start unbuttoning my uniform but stop and turn around to see Leah staring at me intensely.
I get a bit embarrassed and ask her to turn around. I saw her crack a bit of a smile and turn around as I asked. She then started speaking in a shaky, broken voice and said it was cute that I was so embarrassed.
I let out an awkward laugh, but I was happy to see her starting to cheer up. After a minute I had my uniform off, and I was slipping the dress on. Once it was on, I zipped it up and tied the ribbon around my waist into a bow.
I then turned around to tell her I was dressed, but she had already turned around, so now I’m left wondering if she took a peek at me or if she had turned around as I did. Knowing her, she probably snuck a peep or two.
I stand still, looking at Leah and letting her look at me in the dress. I wasn't sure what was going on, but the dress itself was quite nice and perhaps way more important than I first thought. It was also slightly longer and bigger in the chest area than I thought.
Maybe it was someone else’s, someone slightly taller than me and with a larger chest—well, perhaps a chest in general since I don’t have any myself… not that I want them or am jealous about that in any way.
After staring at me for a few minutes, Leah suddenly started to cry, then she jumped forward and hugged me tighter than ever. I felt her tears starting to run down my back, and I found myself super worried for her.
I didn’t know what to say; in fact, I don’t think there was anything I could say, but I knew what I could do. I hugged her back, just as tightly as she held me, and I let her get it all out. Whatever this was about, it had something to do with this dress or the person who used to own it.
I wasn’t going to pry, though; Leah would tell me when and if she wanted. We hug, and Leah cries for several minutes before we are both startled by the door being knocked on and Bentley asking if everything is okay.
He then started to turn the doorknob. Leah panicked a bit and told me to hide in the closet. I nodded and ran over just in time to avoid being caught by Bentley. Leah quickly wiped her tears away and asked Bentley why he barged into her room.
Bentley said he wanted to make sure she was alright, as he heard some strange noises. He then looked around for me, and when he didn’t see me, he asked Leah where I was. Leah told him that I was lost in her closet trying to pick something out for her to wear.
He seemed to buy that and said it was a bit cruel to send the new maid into that closet alone but said he wouldn’t interfere. He then walked over to grab the dishes from Leah’s breakfast. I couldn’t see it, but it sounded like he paused for a moment and made a sound but didn’t actually speak.
Once he had everything, he told Leah to finish getting dressed as the photographer was waiting outside. Leah sighed and said she would, then slammed the door on him once he was out. Once we were in the clear, Leah had me come out and get changed before he came back.
I then took the dress and asked Leah what she wanted me to do with it. It was a bit wet now, so putting it back on the hanger seemed like it was a bad idea. She took it from me and said she’d take care of it and that I did enough for her when it came to it.
She then told me to go grab whatever dress was closest to the entrance of the closet and bring it to her so she could get dressed, which I did. When I got back, the yellow dress was gone, and Leah was in her underwear.
I cover my eyes as I hand her the dress, and she once again laughs at me for being shy and embarrassed about this stuff. She starts getting dressed while telling me she used to be like that at first when she was discovering herself.
I asked her what she meant, and she told me a lot of trans people feel embarrassed about their bodies and even seeing others bodies. It can be because they don’t like the way their body is, or they get jealous, or they just feel dysphoric.
She said for her, once she accepted that she was nonbinary, she felt more comfortable with herself, though she still gets moments where she feels wrong, like when she’s back home and pretending to be a girl.
I could understand what she meant, but I wasn’t sure what that had to do with me; I’m not trans. So I asked her if she thought I was trans. She seemed confused and asked me if I wasn’t. I shook my head and said I was clearly a guy that was being forced to cross-dress.
That made her laugh, but she quickly stopped and apologized, saying that wasn’t something to laugh at. She then apologized to me for thinking that without asking. She said she thought that I was just so out and open that I didn’t need to talk about it.
She then put her arms behind her head and seemed disappointed. She told me that she was usually spot-on with these things. She really thought I was a transgirl, or perhaps just genderfluid, and not once did she think I was just a femboy.
I pout and say I’m not a femboy, just a normal guy being forced to cross-dress. Leah smiled hearing that again and just shook her head. She patted me on the head and said if that's what I was, then she accepted that, but should it change, she’ll accept whatever I change into.
Comments
Riley
The whole gender thing is truly a struggle; it has some cute moments but some really deeper sad moments. As for the dress, I have a whole story for it, just not sure when to drop it in the story. Maybe when they go back to college, or when he wears it again.
last_of_workers
you know it's really funny to watch over and over again how Bryce tries his best to hide from everyone, including himself, who he really is... although... it's only funny until you realize that this is part of the cruel and unpleasant truth... at that moment it becomes much less funny and much sadder... and I'm also very interested in what's hidden behind the story of this dress?
