Riley Gendreau
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Forced to Crossdress: Leo Williams
🕑 Added 2025-03-11 23:42:19 +0000 UTCMy name is Leo Williams, not gosh damn Leah Williams, and I’m a nineteen-year-old non-binary badass, not some peppy little princess who frol
My name is Leo Williams, not gosh damn Leah Williams, and I’m a nineteen-year-old non-binary badass, not some peppy little princess who frolics through fields of flowers. I sigh and say to myself as I stand in my dorm room looking into a mirror.
I once again have to wear a stupid dress that costs more than many of my friends' monthly student loans. If I don’t, my father will scold me for acting tomboyish and being an embarrassment to the family.
I also have to wear this long-ass wig and all this makeup for the same reasons. If my father found out I cut off most of my hair, he’d freak out and force me out of the college I’m in and enroll me into some tight-ass all-girls college.
As for the makeup, he just tells me I look bad without it, and I don’t really care about that, but then he starts nagging me about my mother, and how amazing she looked wearing it, and how when I wear it, I remind him of her.
So I put it on just to shut him up. If I didn’t need him in order to pay off my student loans, I would have already cut contact with him and forgotten that he exists, but I still have a few more years until that happens.
Once I’m free of him and have my degree, I’ll get an awesome job, buy an incredible house, and start a family of my own, one where my kids actually feel loved and accepted for who they are. I start thinking about that life, and suddenly Bryce pops into my head.
That adorable little crossdresser. Is she really the one I think about when picturing the future? That’s funny; I really don’t think I’d mind that. She’d make a cute mom after all, with how sweet and adorable she is. I sighed again.
I really wish I got to spend the week hanging out with her. We’d be able to do so many cool things together, and I’d get to see her come more and more out of her shell. Instead, I’ll be playing pretend for a week with Bentley, and then for one day I’ll have to be around my father.
It’s total crap, but at least there is one benefit to all of this. Bentley is a hell of a cook, and I’ll be eating my favorite foods for every meal, oh, not to mention Bentley will be hiring some temporary maids to help out while I’m there. I hope they’re super cute, and not old.
As I look at myself in disgust, I hear a knock at the door and know it’s time to go and get this over with. I grab one of my hoodies and throw it on in order to conceal my identity; the last thing I want is to hurt my rep by letting them see me like this and starting rumors.
I open the door and am met with the most annoying person in the world. Albert Dunway, an older gentleman who’s been serving my family since my grandfather was the head of the family, which was over thirty years ago.
He sees me wearing the hoodie and starts to scold me, and goes right to calling me Leah, which only causes me to tell him to fuck off, and then it gets me scolded for using foul language, and in the end I just keep my mouth shut and walk away.
We make it to the limo that my father insists I be driving around in. Which, luckily, I was able to convince him I didn’t need while here at college, since I can walk everywhere around here, but then going back home or to any other events that require my presence, it’s always the limo.
No one has figured out it’s me going into it, but most of my classmates notice the strange limo that shows up from time to time, and they gossip about who could be in it. They’d freak out if they found out it was me, the person they know as a badass punk and rebel.
I hate lying to them, but if they knew it was me, they’d want to know more about Leah, but Leah is dead… Or more like she’s the real lie. I’m not her, and no amount of pretending will ever make me her. I know myself, and I’m Leo, a they/them problem created by the world, and I love it.
The drive back to the manor was long and boring as we got caught in the nightly traffic. Albert tried to talk with me, but I flipped him off and put up the privacy glass. I then manspread like a boss and watched some BMX videos on the back screen.
Both of which Albert could see from the front, and I could tell he was fuming about it, which put a big old smile on my face. I’ve always been as much of a pain in his ass as he’s been in mine, and I don’t feel bad about it one bit.
We arrived at the manor and I let myself out before Albert could get to my door, though it was funny to see him rush in order to try, since he knew I was going to do it myself. As we walked up to the door, he grabbed my hoodie and pulled on it.
I yelled at him for taking it from me, and he said this was as far as my silly charades go. I roll my eyes and argue with him as Bentley opens the door and we walk inside. Every time I come home, the entire staff of the house is usually waiting here to greet me.
When I was younger, there were nearly a dozen people, but since my father doesn’t actually live here, and I’m at college full time, it’s only Bentley and the temporary maids he hires. I watch them curtsy like they always do, then I see their faces.
I felt my face burn from the embarrassment as I realized the temporary maids Bentley had hired were my classmate Cindy, and my partner Bryce. I wanted to die of embarrassment right then and there. Of all the people, how did Bentley manage to find the person I’m dating?
I look at Bryce and from the way she’s looking back at me, I know she knows, which means I’ll have to explain this all to her. So when Benley tells me to go bathe, I instead Bryce to be the one to come with me so I can do that privately.
We headed upstairs and I let out everything I was feeling on her, only to find out she somehow had no idea who I was. I’ll admit, it did calm me down, but I felt a bit disappointed, almost like I wanted to tell her, perhaps because I didn’t want to have a secret from her.
So I decided then and there to tell her, but first I was going to tease her, because damn, is she so adorable and easily embarrassed. I had her unzip my dress, and then I told her to call me L, as I wasn’t going to reveal who I was yet, and I sure as hell wasn’t going to have her use my deadname.
She got extremely red-faced as she avoided looking down, not that there was much to see anyway. She’s probably got about as much as me going on in that department if I’m being honest. I playfully order her to go draw me a warm bath and while she’s at it, I take off my wig.
I place it down on my bed and go in after Bryce. I see her bent down with her hand in the water testing its temp as it fills up. I have to admit not only was she cute because I got to see her butt, but she seemed to actually be a decent attendant.
Once the tub is filled up, she turns to me and tells me it’s ready. She then tilts her head and asks me what happened to my hair. I laughed and told her I took it off, which only seemed to leave her with more questions.
I step into the bath and lower myself so just my head is poking out. I then ask Bryce if she has figured out who I am yet. She looked embarrassed again and said she had no idea. I smiled and told her to grab a towel, and I’d finally reveal it.
She nodded and turned around; while she did, I dunked my head down into the water and took my hands and started to scrub my face. When I came back up, Bryce handed me the towel and I used it to wipe my face.
I then looked at her and smiled. She then looked at me for a moment before her whole face lit up and she smiled. She nearly jumped into the bathtub with me, just in order to hug me. I actually had to catch her and keep her from getting completely soaked.
She only got the top of her uniform wet, but she didn’t care; she was just so happy to see me, which was sort of relieving. She didn’t care one bit about why I was here, or why I was dressed up like that before; she was just happy to see me, the real me… which is the first time I can say that’s truly happened.
Comments
Riley
I get it, Leo hasn't really appeared all that much in the main series. They actually appear more in Dreamy Knight as their fantasy version. So while this is the second time we see them in a part. (They were mentioned in others but not in a big way.) This is the first real part for them, and the first time we get to know anything about them, really. I do also take my time with this one; it is one of my favorite series, though, so maybe that's why. I don't want to work on it until I know I'm really ready.
last_of_workers
I'll be honest, I personally just forgot about Leo's existence... maybe it's because of your midseason "Dreamy Knight" maybe it's because this series doesn't get updates very often or maybe it's because I wasn't really interested in this series of stories from the start... overall, I was happy with everything, but my problems are just my problems and I'll figure them out myself somehow
