Forced to crossdress Pt4

Heyo there! My name is Bryce Cooper and for the past seven months I’ve been spending my weekends crossdressing thanks to my best friend Cindy. Originally it all started with us exchanging favors.

She’d help tutor me so I could pass my classes and in return I’d help her and become her personal test model. I’ve since been doing good in my classes, but I guess I’m kinda addicted to how she spoils me, so when she wants to dress me up I don’t resist.

Sometime last month I went with Cindy to be her model for a class test she had, it was there that I met a ton of other people who also let their friends practice on them. It also helped me be less embarrassed when I realized other guys were also crossdressing like me.

Even one of the cool kids from my school was there. Leo, a non binary student, was also there, as a model for a friend. Speaking of Leo, the day after Cindy’s test they approached me when I went to school.

When they ran up to me talking about the day before I began to panic a bit. I was wearing my normal male clothes to school, and until that point no one had even known or recognized my two personas as one.

They noticed my panic and asked me about it. I kept studying as I tried to explain, once I got enough out they seemed to understand. They put their hands on my shoulders and explained they would tell a soul.

They then asked if I'd prefer they treat me how they treat their gender fluid friend. Meaning they’ll use he/him pronouns when I dress masculine, and she/her pronouns when dressing feminine.

They also mentioned they wouldn’t ever bring up the other half, that way if I was keeping it a secret from certain people, they wouldn’t out me to them. I thought that sounded good and agreed to it.

Leo removed their hands from my shoulder and smiled. They said they like knowing all their friends' pronouns. They mentioned they already know I knew theirs, saying Cindy mentioned it in a text last night.

I was quite surprised that Those two talked. I guess a lot has changed since I first met CIndy. You could say I’m not the only one breaking out of my shell, afterall she used to be known as the weird girl, now she’s the one every girl goes to for tips on fashion, makeup and hair.

The bell rang and ended my conversation with Leo early. They said goodbye, saying we needed to hangout sometime, and ran off. I smiled and waved back and said something for sure. I was about to walk to my class when something hit me.

I had told Leo it was okay to refer to me as she/her when I’m crossing dressing. The mere thought of it caused my face to heat up and turn red. It would definitely help keep my two personas separated, and honestly doesn't sound like it would be all that bad.

I go to class, and spend the whole time thinking about it, and Leo. There was something about them, I felt drawn to them. Maybe it was the fact that they were one of the few people who knew about the crossdressing I’ve been doing for CIndy.

Maybe it was the fact that they were okay with it, even embracing it. Or maybe I’m drawn to them because they’re cute. Wait what did I just say? I didn’t mean that right? I mean what is even cute about them?

I mean they’re super cool and everyone loves them, they totally rock the goth look, their hair is well designed, with the long bangs and ponytail. They’re kinda very fit, they have just enough muscles showing to look strong but not overly masculine.

Then there's their personality, they’re always smiling and friendly. They always seem to be able to pass that to those around them, I’ve seen them talk to other people crying and moments later they'll be laughing together.

Oh my gosh, we only ever talked once, why do I know all this? There's only one explanation for this feeling I have, I have a crush on Leo. I continue to focus on this during all my classes, and as soon as the school days ends, I rush to find Cindy.

I tell her I need to talk to her in private somewhere. So the two of us sneak off to one of the private gender neutral bathrooms and lock the door. At this point Cindy is the person I trust most in the world, so I blurt everything out to her.

I tell her about talking with Leo, to all the feelings afterwards. Once I was done I looked at her waiting for some sort of response, some sort of joke or even some advice. At the very least I was expecting to tell me I was being silly.

She just smiled and laughed. Saying people have crushes all the time, she was even surprised this was the first time I’ve had one. She did end up making a joke, saying I was crushing hard, almost like a teenage girl.

Once she finished, I asked her what I was supposed to do about it. She stopped and seemed to think about it. She then simply said whatever I felt like I wanted to do. I looked at her confused and told her that wasn’t helpful.

She then explained it was really up to me. She said most crushes went away after some time, but if it was more than that, she suggested I try asking Leo out. I asked her how I was supposed to know if it was more than a crush.

She once again stopped to think about it. Her answer was that she thinks it's different for everybody. For her, crushes tend to be baseless, the simple idea of someone, but when she genuinely loves being around someone it's more.

She then poked me on the face, saying that's how she feels about me. She then laughed and said of course that love is more like a best friend or sibling. She then got up and left the bathroom.

I sat there for a few minutes trying to think about it. Something more is love? I don’t think I’m in love with Leo, I barely know them. I guess it's merely a crush then, so the feeling will go away in time.

I make my way back home, and lay in my bed and stare at the ceiling. I kinda just reflected on everything that's happened to me over the last few months. It’s been very awkward but also sorta a fun experience.

So even if I’m experiencing new and strange feelings, I know I’ll figure them out eventually, so there's nothing to worry about now. I sit up and look over towards my dresser. It's now filled with tons of makeup.

I go over and sit down and begin to practice some of the things Cindy’s been teaching. As I’m about halfway, with my hair pulled back and makeup open all around me, my phone beeps from receiving a text.

It was Cindy, she said she had another in person test this sunday. She asked me if I would do it, I of course said sure. She seemed happy, but she said she’d need to drop off my new outfit the day before.

She also asked me to do my best on the makeup, saying she could redo it if it’s bad, but it will look a lot better if I show up already wearing some. This was extremely unusual, but I feel pretty confident in doing so.

She also said it was going to be held in the park next to the college. That was also another unusual thing, her class didn’t seem like it could work in the middle of a park, but who am I to know.

So Saturday night comes, and Cindy shows up and gives me the new outfit. A cute blueish  dress, with short tight shorts, a cute little choker and a pair of heels. Cindy dyed my hair so she won't have to do it tomorrow and begins to go over what I’ll need to do for makeup and stuff.

She leaves and I head to bed, kinda excited for tomorrow. I wake up nice and early and begin applying makeup, and styling my hair. Once all that's done I go ahead and attach some fake nails that CIndy had already painted for me.

Once I was all dressed up and looking cute and adorable I left my house and got on the bus. The bus driver gave me another strange stare but didn’t say anything, and I made my way to the park.

I arrived about ten minutes before the time Cindy mentioned, and I began to look around the park. I figured at least some people would already be here setting up, but no one was here, including Cindy.

It was now about two minutes before the time, so I texted Cindy and asked her where she was at. That's when she came clean, saung there was no class, and she wasn’t showing up. I was kinda mad and asked her why she did all this.

She simply sent a smiling emoji and said she was just helping me out. I was about to ask her what she was talking about, but someone put their hands on my shoulder to get my attention. It was Leo?

I greeted Leo asking them what they were doing here. The embarrassment that came with their answer almost made me pass out. Leo was here for our first date in the park, and Cindy’s the one who set us up.