Forced to crossdress Pt5

Hello there! My name is Bryce Copper and for the past seven months, I’ve been spending weekends thanks to the support and efforts of my best friend Cindy. All those months ago it started as a deal between us.

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.

I recently developed a crush on another person at my school. Leo is a non-binary student. I’ve seen them around the school before, but I think the first time they noticed me was at one of Cindy’s classes when I was her model.

After that, they approached me to chat and I was incredibly embarrassed. After chatting I grabbed Cindy and ran to the bathroom to talk to her. That’s when I learned I was crushing on Leo.

After that Cindy told me she had another test that she needed me to show up for. This time it was on a Sunday in the middle of the park. Strange I know, but it was Cindy so I didn’t think much of it.

The day comes and I show up in the park to find only Leo was there. When I asked them what they were doing here, I almost passed out when they answered. Leo was here for our first date, and Cindy had set it up.

I was incredibly nervous, but I didn’t want to leave. One I kinda wanted to be here with Leo, and two I didn’t want them to get mad at me. So I walked with them through the park. After a minute of walking Leo started talking.

They started by calling me pretty, then calling me cute for blushing so much. Then they started asking me things about myself. I began answering the questions and asking some myself.

Over time I opened up a lot, and we were having full-blown conversations about pretty much everything. I was surprised we had so much in common, from video games to our favorite color, which is pink.

Although Leo doesn’t seem to wear a lot of pink. So I questioned them on that, and their response was that they like to see pink in their favorite things, then smiled at me. I truly have no idea what that means, but I smiled back.

Leo then said there was an awesome food truck that parks nervy with the best burgers. They grabbed my hand and pulled me as they ran. We made it to the truck and waited in line behind several people.

I looked down and Leo was still holding my hand, and inside my head, I was freaking out. It was so strange, I was excited and happy, scared and nervous, and entirely worried about Leo hating me for still holding their hand.

In the end, I didn’t let go. We got to the front of the line and Leo ordered what they wanted. Then the man asked me what I wanted. I had gotten used to being out in public crossdressing, but I still have a hard time talking to people when I’m doing it.

So I froze. The man looked annoyed and Leo ended up ordering for me and covering for me. They looked at the man and straight up said, “Sorry about my friend she tends to get a bit nervous around people, but that’s what makes her so cute.”

I felt my soul slowly slip out of my body as I heard that. It felt so good to hear, but I swear the embarrassment was killing me. Once our order was put through we sat on the side until it was cooked.

Once it was cooked, Leo paid for it, and even though I offered to pay for mine instead it was her treat. We sat down on a nervy bench and began to consume the massive burgers that They ordered.

It was really good, the flavors were amazing and every bite was better than the last, unfortunately, it was too big for me to finish. Leo on the other hand had no problem finishing it. Despite us being the same size, they sure can chow down.

I know some people tend to be self-conscious about eating like that on first dates, so the fact Leo didn’t feel that way told me they were really comfortable around me, or at the very least not someone who pretends just to please people.

We tossed our trash into a nearby trash bin and continued our walk. This time Leo just stuck their hand out next to me waiting with their palm open. I looked at it and then I looked at them, and they were smiling.

Leo said they noticed how long I held onto it before, and they didn’t mind, so if I wanted to do it again they’d love that. I must have turned red again because Leo poked me and said I was doing that cute thing again.

I grab their hand and we start walking again. We continue chatting and this time the conversation leads to Cindy. Leo mentioned how much she’s changed these last couple of months.

Leo mentioned they had met Cindy through Leo’s friend that's in her class. Back then Cindy never talked to anyone and never seemed to have any friends. It got to the point where everyone started rumors about her and she became known as the weird girl.

Leo suspected that it cause her to become even more closed off. Leo had tried to talk to her once but wasn’t able to break down her walls. It stayed that way up until about seven months ago.

Leo noticed her coming to school, but instead of her normal sad-looking self, she seemed chipper. Over the coming months, she started making friends with her classmates and becoming more open with everyone around her.

Every time Leo saw her she seemed happier and they had no idea what had changed in her life. That was until a short and cute little person showed up to her class a month ago to be her model.

They said they knew any person able to change a person for the better that much had to be someone extra special. So they had to meet and get to know them. So when Leo asked Cindy if they could hang out with me, Cindy told them about my crush.

That's how we got her today. I had completely forgotten all the things people had said about Cindy back then. She was a very different person now, I suppose that goes for both of us though.

I’m glad to hear her life is better and she has so many friends now. She’s become quite popular in school just like Leo, so I’m glad that she still values my friendship enough to find time to hang out with me.

As I was thinking all that another thought popped into my head. Leo had known this was a date because Cindy set it up, and they knew I had a crush on them, and we were holding hands. Does that mean they like me back?

I stopped and for some reason blurted it out. They looked at me and laughed, they said I was pretty oblivious. Then Leo pulled on my hand, pulling me towards them. My chest was now touching theirs and I was looking up at them.

Leo smiled and said, “Since I have to spell it out for you. Yes, I do like you.” Then Leo leaned in and kissed me on the lips.  I was so surprised, I know I turned red, but this wasn’t like before. I wasn’t embarrassed or nervous.

I was just happy. Leo moved their head back and asked if that answered my question. I nodded and wrapped my arm around them and pulled them back in. We kissed again, this time for much longer.

Afterward, we continued our walk, once again holding hands. About an hour later we end the date and we agreed to start officially dating. I waved to Leo as they left and I was already excited for our next date.

After I left Leo I got on a bus and headed to CIndy’s house. Once I arrived I pretty much broke her door down while knocking. She answered the door and lead me up to her room. As soon as she shut the door, she began asking for details.

I however began playfully fighting her asking her how she could do that to me. She laughed, asking if it went well. I told her about most of it and she seemed super happy for me, even saying we’d be a cute couple.

She hugged me and told me she was so proud of me for not messing it up, and told me that I can pretend to be mad all I want but she knows I’m grateful that she did it. I laughed and told her as true as that is, being mad at her is fun.

After that, we relaxed in her room, and we did a bit of studying and a bit of dressing up. Sometime later she asks me if I’d be willing to do her a favor. I told her, yeah, but she insisted I hear it out before agreeing.

She apparently wants to step up her game in the fashion side of things, but she needs all new equipment, like a sewing machine. The problem is those things are expensive, and she needs to get a part-time job to pay for them.

She had a job set up, one week's worth of work and it would be enough to pay for everything. The thing is it required her to have a partner or they won't hire her. Cindy would be making my clothes with it, so how could I say no?

I once again told her I would do it, but she shushed me, saying to let her finish. Cindy then said the job was for cleaning a mansion, so we’d be maids. I still didn’t see the problem, but Cindy then pulled out some clothes to show me.

She meant it literally, we’d be dressed as maid girls for the entire week. That's so embarrassing, cross-dressing was one thing, but parading around as a cute little maid for complete strangers for money?

A part of me doesn’t want to do it, but another part of me really wants to get into the maid's uniform. I think Cindy realized that, and pulled it away from me, saying I only get to wear it if I agree to work with her.

She even sweetened the deal saying I could keep it, even going so far as to say She thinks Leo would love to see me in it. I gave in and agreed, jumping forward to grab the uniform from her so I could put it on.

Once I was in it, Cindy said I was very cute, and I turned to see her in a similar outfit. I smiled at her and twirled the skirt of my uniform. She smiled back at me and said we start tomorrow after school ends.

So for the next week, I’ll be forced to crossdress as a cute and adorable maid. It might not be that bad, I’ll get to take some pictures and keep the outfit, and maybe Cindy is right, Leo might like to see me in this outfit.