HELP WANTED

Oh yeah, here is a picture of me in that outfit, just so you can kinda see I’m not exactly small, and what i was talking about with the open shoulder stuff. Oop, I look at that and I didnt rember that it was more chest window than shoulder stuff, but anyways, here it is

aw, that's great that you made the discovery! I think you should tell your boyfriend now because just doing it randomly could break your relationship. For make-up if you are on a budget I suggest wet-n-wild, and if you can afford to splurge go to Sephora or Ulta, but be warned 3-4 things add up quickly to nearly $100 and there will be lots of slimy kids at Sephora, Ulta is a bit cheaper but still expensive and has less but not no kids. for cross-dressing just but whatever you think makes you feel the most like yourself or how you want to present! Sometimes even the cheaper places have good clothes! I hope this helps you <3

Thank you so much, being a dude, all I’ve ever know about makeup is like… idk foundation then blush, then eyeliner, and I dont even know how to do it and like, I WANT to, but idk if it will give me the same reaction as like, cross dressing does, but I do feel that like, when i see people, that wear makeup, they look attractive, and I want to look like that, but most of the time people who wear makeup are women. Another little thing, I dont know if this is gonna lead into any drag or stuff like that, it might, but I doubt it because drag has been WAY over-shown, and dammit what is the word for like, society took this niche concept from another culture and ran away with it for TV purposes, anyways, I have been thinking of trying to find a few drag queens or at least someplace that does drag, so I could get advice from them, idk if that is a good idea or not. Another thing I struggle with is that like, as much as I want to cross dress, sometimes I dont feel I look good in things because I’m not skinny and twinkish, like… my boyfriend, he could rock the smol twink style any day, but I’m too… (ugh I dont want to say buff because that sounds like I’m bragging, I don’t want to say built because that also sounds braggy… UMM) I’ll just say thicc to wear some clothes that look better on skinny people. And like I do HAVE big clothes and smol shorts that kinda make me look smol and cute but like i have to get a XXL from COSTCO if I want anything oversized and it get ridiculous. Please let me know if you have any more help or feedback to give, I do really need some help with this.

There are tons of makeup tutorials online. And some specifically for guys. I would suggest blooking up some of them on YouTube

Ok, thanks

First of all you're really brave.
As a whole guys are more pressured than girls to stay inside of gender roles. A great way to start cross dressing is to wear more form fitting clothes. It can be as simple as wearing skinny jeans. Also balancing different elements of tight vs flowy clothes will give you a more balanced look. Women often choose a statement piece while styling. (Generally a top but can vary) and style around it. Find colors that compliment it(black and white go with everything) or try a monotonous look with different shades of the same or similar colors.
Looking up male celebrities or models can help.
I'd recommend getting your ears pierced if you're comfortable with that. Putting in earrings will allow you to present feminenly without much effort.
I can't give you much advice on makeup but eyeliner makes everyone look hotter.
Ultimately experimentation is key.
As for your boyfriend you'll have to figure that out yourself sorry.
Tell me if you have any other questions I hope this helped.

Ok so… I’ve tried wearing more form fitting clothes, but I dont own anything that is MEANT to be form fitting like booty-shorts or yoga pants or sumthin, but I have tried to kinda wear althetic shorts that are tighter, but being a guy and having dude parts, I’ve gotten complaints and demands to change from my Mom regarding what she can see in the front considering how tight the shorts are. I dont know what tops to get but I’m KINDA thinking liek some top with like string straps because like, I work REALLY hard to look good with my body and liek I like to show off my arms and legs when I wear some stuff, but then again, I dont know exactly how I’ll look. Um there is one time where I found an excuse to wear this quirky little maid outfit (I’ll include picture) and that had like, nice open shoulders, kinda flowy, but not REALLY my style because its is too over the top. Another thing I struggle with is that like, as much as I want to cross dress, sometimes I dont feel I look good in things because I’m not skinny and twinkish, like… my boyfriend, he could rock the smal twink style any day, but I’m too… (ugh I dont want to say buff because that sounds like I’m bragging, I don’t want to say built because that also sounds braggy… UMM) I’ll just say thicc to wear some clothes that look better on skinny people. Oh, and i hav been trying to get my ear pierced for a while, but my parents say, not till I’m in highschool MEAN WHILE my aunt just got the ears pierced of her SIX YEAR OLD DAUGHTER and I’m like DOUBLE STANDARD MUCH?! Anyways. Tell me what you think if you want

Oh all right. Sorry I was under the impression you were a grown man. So if you want to get around the earrings thing use magnetic earrings or clip on. The main problem with your parents seems to be that some clothing is too revealing. Yeah I listen to them. If you really are in like middle school or whatever it just copy what the girls around you are wearing. But adjusted for your measurements and other stuff. Also about your boyfriend. I don't worry about it no relationship from that age lasts. If he thinks it's weird that you wear that stuff than screw him. Also forgot about your body image. Every kid hates their body around that time, even more so trans kids. Also if you would be comfortable, you could show me a picture of outfits that you like to wear. To be on your body or with your face in it just the clothing. It'd be easier if I knew what you wore

All of these are pretty masc, but again, I want to start crossdressing, oh and if you had seen the shirt from the middle picture without the jacket, it looks way fruitier. Sometimes I wear a sleevles black T and that jacket combo but I let the jacket drop over my shoulders and that is pretty much teh most fem I’ve taken it, well besides the maid outfit but that was a VERY special occasion

No, yeah I’m 14. Ok, so I cant copy what the girls around me are wearing because like, it’s a uniform school. And again, like I mentioned up there, I’m cis, I’m not trans, I’m not an egg, I just like wearing those clothes. Ok some outfits I like to wear…

First things first, you look great. I noticed you often wear more muted tones. A great way to look feminine is by incorporating brighter colors into your wardrobe. Also you have very nice hair have you considered learning how to style it? I've seen many girls do crazy things with their hair and it looks so good

I have learned how to style it, but I dont wear anything fancier than a bun or a braid because I run around and do stuff too much for anything else to stay in place. I should get more vibrant and colorful clothes, that is a good idea. Oh, my boyfriend is also gonna give me a bunch of old necklaces and bracelets that he was gonna throw away and I liked, so I am gonna he a few more options in that respect as well.

Nice, any other questions?

um, not really I actually talked to my boyfriend about this at like lunchtime, and now we are talking about what dresses I could wear, so that worked out, REALLy well

congrats

That's great!