Riley Gendreau
patreon
Forced To Crossdress: Pt2
🕑 Added 2023-10-12 00:23:36 +0000 UTCHello, My name is Bryce Cooper. For the past month, I’ve been spending the weekends at a girl named Cindy's house. She agreed to tutor me in exchange for letting her practice her fashion and makeup skills. I got to her house nice and early today. She had me set up all the homework I was currently working on and she grabbed all of the products she was testing out today. I went to work on the homework and she went to work on me.
She insists on turning my hair pink every time I come here. It washes out after three days but I’m now wearing a hat to school more often, which she tells me is bad for my hair. I’ll admit though, it's grown on me, I kinda miss it by the end of the week. Then comes my break time, this is when she applies all the makeup to my face. She’s good at it, I mean she can turn a guy like me into an adorably cute girl. Sometimes if I finish early she forces me to learn how to apply makeup on my own, not that I need to know.
As soon as I finish up my work she takes me upstairs to try on an outfit and take a picture so she can submit it to her teacher, apparently since I’ve been helping her she’s been at the top of her class. Today's outfit consisted of a pair of white panties and a small pink dress with matching boots. I didn’t even fight her and went and put it all on. It was kind of strange, everything fit so well, and she was bigger than me.
So she must have guessed my sizes and bought these just for me. I walked out and she looked ecstatic, she ran up and hugged me. I was extremely embarrassed but it felt good, she told me I was like her wonderful little sister. I was told to sit on her couch and pose. I knew better than to argue with her and sat down and did my best to do a pose. Normally she just takes one or two photos, but I think she took a lot more than that this time, maybe even a video. After a month of no one finding out, I wasn’t worried anymore.
I could trust her not to share it with others. Plus at this point, she was so good I doubt anyone would recognize me. After a few minutes, she was all done for the day. We were both done for today, we were about to remove all the makeup and clothes when her parents came home early. She freaked out, normally they get home very late on weekends and she wasn’t allowed to have boys over. She told me if they found out I was a boy, I wouldn’t be allowed to come back again, which would be very bad for me.
I was getting better with my work but still had a way to go if I wanted to pass the class. So I agreed to pretend to be a girl, and we would use the real reason for my being here. So she hid all the clothes I came in and we sat on her bed. She pretended to be doing my hair when her dad came knocking. They seemed surprised that Cindy had a friend over, they asked me a ton of questions and I did my best to answer, luckily Cindy kept answering for me. The rest of the day flew by and night came quickly.
They apologized for keeping me so late and insisted I stay and have a sleepover with Cindy. She agreed, mentioning that the buses around here don’t run this late. Now not only have I been crossdressing all day, I’ll now be doing it all night. I agreed, her parents made dinner and we went up to her room after eating. She apologized a ton to me. She knew I didn’t want people to see me like this, but she had no idea they would be home this early.
I told her it wasn’t that bad, her parents were super nice and at this point, I kinda enjoy hanging out with her. Her eyes started to tear up and she began crying, I guess she’s never had any real friends before. We spent the rest of the night pretending to have a girl's sleepover, I guess you could say we did have a girl's sleepover. We did hair, she talked about boys and we even had a pillow fight before her parents asked us to go to bed.
When I woke up the next morning she looked kinda panicked. I asked her what was wrong and she told me her dad had the day off today. I then asked why that was so bad. That's when she told me I had to leave wearing the outfit from yesterday or she’d get in a lot of trouble. I told her there was no way of doing that, that would mean getting on a bus riding for fifteen minutes, and walking ten minutes through my neighborhood. She then reminded me what would happen if her dad found out I was a guy.
At this point, I was probably as red as a stop sign due to how embarrassed I’d become. I decided a little bit of embarrassment didn’t outweigh the risk of failing my classes. So I slid my old clothes into my backpack and walked downstairs with Cindy. I said goodbye to her dad and thanked him for letting me stay, and for the first time, I walked outside wearing nothing but a dress. Cindy walked me to the bus while holding my hand, then again apologized as I got on the bus.
I think the bus driver recognized me but didn’t say anything. I got off at my stop and walked as no suspiciously home. I think I got home without anyone seeing me, luckily I live alone so I don’t have to worry about my parents as she does. After the embarrassment of this whole ordeal ended I went up to my bedroom to get out of this outfit, I stopped when I saw myself in the mirror. For some reason, I loved how I looked, perhaps one day I could date a girl as cute as me.
I took a few pictures just to keep to myself, no way I’d show these to anyone. While I was doing so I got a text from Cindy asking If I got home okay. I told her I did, and that I don’t think anyone I know noticed me. She once again apologized, she even told me to keep the stuff I was wearing, she admitted to getting it in my size just for me to wear. Then she asked me if our agreement was still on, I said yeah but asked if she was willing to do it at my house from now on. She replied saying that since I met her dad, he’d have no problem with her spending the day or even night at my house. So overall something good may have come out of this, now I don’t have to travel to her house every weekend and I guess these clothes aren't bad.
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Riley
Just adding this to the archive, it's an old caption from before I created my Patreon.
