Forced to Crossdress: Pt3

Hello again! My name is Bryce Copper. For the past six months, I’ve been spending every weekend cross-dressing with my best friend Cindy. Originally it had started out as some sort of deal between us. She would tutor me to help me pass my classes in exchange for letting her practice her hair, makeup, and fashion skills for her own classes. At first, I was incredibly embarrassed but I grew to like it.

I was incredibly embarrassed when her dad came home early one day and I was forced not only to meet him while cross-dressing, but I was forced to go all the way home in public too. Of course, I almost died of embarrassment but she let me keep the outfit so it ended up okay. Since then, I’ve gone out publicly a few times, but that was only to see her dad so he didn’t get suspicious about where she was hanging out all the time. It's still incredibly embarrassing, but thanks to Cindy's skills, I no longer worry about anyone recognizing me.

It was Sunday night and I was chilling in my room with Cindy. We had both finished up for today and we were just laying on my bed together on our phones, something we’d been doing more often lately. She broke the silence when she told me she had something very big to ask of me. Confused, I asked her what was up. She told me her teacher wanted all her students to show off what they’d learned in class on Friday. She then continued that her teacher required me since Cindy had been using me this whole time.

I guess the teacher wanted to make sure she wasn’t cheating, I get it, Cindy is so good you’d think the pictures she takes are edited. I didn’t say anything, I just turned red. I told her that I still wasn’t comfortable being in public dressed. What she was asking was for me to go dressed like a boy and get transformed into a girl while the entire class watched. She begged me, she said her teacher would fail her if I didn’t go. She told me I had nothing to worry about, I wouldn’t be the only boy there.

Some of the people taking the class are boys and some of the others coming in to be practiced are just like me. The thought of it all still had me sitting on the bed red as hell and not saying a word. That’s when she went to her backup plan, that’s right she started to bribe me. She promised to not only let me keep the new outfit I’d be wearing, but she’d also take me shopping afterward for another. This sorta snapped me out of it, I'll admit I've become a sucker for all the cute outfits she gives me. I might even have more girl clothes now than boys.

I must have stopped being red because she could tell I was thinking about it. She then said I could pick the outfit out, anything I wanted she’d get it, and afterward we could have a night on the town since I’d be all dressed up anyway. By now I know she won't give up, and she’d go broke trying to convince me to do it. I finally agreed to it, which made her super happy. As the week passed I couldn’t get the thought of this event out of my mind, it made my heart pound like crazy every time I thought about it.

Eventually, Friday came, and I met Cindy in her classroom. She introduced me to her teacher, who praised me for being an amazing friend and helping Cindy. She also mentioned I looked great in all the photos and she couldn’t wait to meet “the real me”. Seven people in the class will also be working today. There was me of course, two boys and three girls, that I’d never seen, and Leo. I don’t know Leo, but I do know they’re non-binary and one of the cool kids.

I didn’t know they were into this, perhaps they’re good friends with the person working on them. That would make sense, it’s why I’m here at this point. Seeing the wide variety of people here actually calmed me down a bit. I guess it’s not that weird that I’m here. The teacher set up an area for each pair, with privacy curtains, and told them to get to work, everyone had two hours to complete their work. Cindy sat me down and looked me over, she had this intense fire in her eyes.

That usually means this is going to be her best work. My hair had grown out a bit, so she took this opportunity to trim it down, she even gave me a super cute hairstyle. She then started dying my hair the standard pink I’ve gotten so used to. She dried my hair and stopped for a minute to double-check it to make sure it was perfect. After she knew it was good she moved onto the makeup. We had about forty-five minutes left at this point and she was going to make use of all that time.

She started by plucking my eyebrows, she’d done this before but not this much. It hurt like crazy. She applied makeup to my eyelashes, around my eyes, around the cheeks, and finally a soft lipstick on my lips. She took my hands and glued some fake fingernails on them, afterwards, she painted them black. I’d never had fake nails before, they were fun to play with. I felt like a cat, all I wanted to do was scratch things, which of course made her yell at me not to ruin them.

After she finished putting everything away she pulled out the bag with clothes and the newest addition to my closet. It was a very short spaghetti-strapped dress, with black panties and two thigh-high black heels. The heels were the highest I’ve ever walked in, but I’ve had enough practice by now so it wasn’t a problem, but I did enjoy the feeling of being tall. The teacher announced that time was up, everyone was to step out with their partners and prepare to be evaluated.

I was shocked when I saw the others, the other two boys were completely changed. They both looked like girls, just like me. One was dressed like a cheerleader and the other was dressed in business attire. I did notice one big difference between us, they both had some sort of fake boobs. For some reason I was kinda jealous, I wondered what it felt like to wear. I shook those thoughts away and continued to look at the others. One of the girls was made up to look up a tough-looking biker dude, with fake scars and tattoos.

The other two girls wore long dresses, the kind you’d see at movie premieres, they also had fancy hairstyles and matching makeup. Honestly, if I didn’t know, I’d think they were some famous actresses. Last was Leo. Leo wasn’t wearing anything fancy, but it was still a cool outfit. They had a cropped Lgbt shirt with a long-sleeved shirt underneath that. They were wearing short shorts, with leggings underneath and long boots similar to mine but with no heels.

I think I was staring a bit too long, they noticed and smiled at me. They shouted from across the room that I was cute and winked at me. I became extremely embarrassed and looked at the floor. I even put my hands behind my back. The teacher graded everyone on their work and handed them all the reports, which included the score and any improvement suggestions. Cindy showed me the paper and she passed with a near perfect score.

We left and as promised, Cindy brought me shopping. It was so fun I completely forgot how embarrassing it is to be out in public. I picked out a few things and so did she. We went to a changing room and tried on a ton of stuff. That’s when gave me a bra to try on. I couldn’t believe it all this time and I’ve never tried on a bra. She helped me find my size and she brought me a ton to try on. She even bought me my favorite three. She told me I’d start wearing them when I’m dressing up from now on.

She told me she was hesitant to get me to try them, but after watching me stare at the other guy's fake boobs, she knew I’d like it. I blushed a bit, but she was right. I didn’t realize she was watching me so closely. I made a joke about it and she commented how she noticed a lot about me lately, especially today in her class. I didn’t know what she meant and she refused to tell me, so I dropped it and continued to enjoy the rest of the day. I couldn’t wait to get home and add all these new clothes to my closet and you know get out of these heels and relax.