Hi, new here!

[Chrisloveschastity]

Hi, I’m Chris (he/him) I’m new here. I’ve been really interested in crossdressing and sissification but haven’t gotten to far into it as of yet. I’m really hoping to be able to visit the store soon or even order online to get my first sissy outfit. I’m pretty shy and consider myself an introvert. I’m not out as a sissy yet but hope to be one day. I’d really appreciate any tips for a beginner sissy that could help me out in finding the right clothing/make up and anything else. I have a chastity cage already and wear it regularly. I’ve been dabbling with wearing panties for a while now and I wear those regularly also but that’s about all I have for sissy stuff so far. I just want to dress up and feel feminine. I’m not trying to pass, I just feel it’d be fun to dress up now and again.

[CanuckGirl]

Hi, I’m Chris (he/him) I’m new here. I’ve been really interested in crossdressing and sissification but haven’t gotten to far into it as of yet. I’m really hoping to be able to visit the store soon or even order online to get my first sissy outfit. I’m pretty shy and consider myself an introvert. I’m not out as a sissy yet but hope to be one day. I’d really appreciate any tips for a beginner sissy that could help me out in finding the right clothing/make up and anything else. I have a chastity cage already and wear it regularly. I’ve been dabbling with wearing panties for a while now and I wear those regularly also but that’s about all I have for sissy stuff so far. I just want to dress up and feel feminine. I’m not trying to pass, I just feel it’d be fun to dress up now and again.

 Chris, welcome to the forum!
 I'm not sure where to start about giving you tips, but figuring out your sizing is a good place. If you are buying from a somewhere like Janet's they should be pretty good at helping get clothes which fit you properly.
 Also it depends what your goals are, and if you are like most of us you have no idea where this is going to take you. I know I didn't, and in a way still don't though I now have self acceptance of my crossdressing needs and can enjoy it much more. Maybe you will get interested in going out to meet other CDs or just out in general as you go further into this.

 There's a wide range of you tube tutorials about makeup, or if you get to Janet's they can help. Stores like MAC, Sephora and others are very good at helping you with makeup though of course they are expecting you to buy some too.

 Thrift stores are great places to find cheaper clothes to experiment with. My experience has been of total acceptance when shopping for women's clothes in drab mode even with other female shoppers around but one does have to achieve some kind of comfort level to do this.
 So give it a try!

 One trick to figure size, is to measure your waist fold the tape measure in half and see how far it comes up your arm from your fingers, remember the spot and you can quickly figure out if that skirt's waist will fit you. Ditto for your chest.
 Look for clothes with stretch as well, that helps a lot too.
 Amy

[Chrisloveschastity]

Hi, I’m Chris (he/him) I’m new here. I’ve been really interested in crossdressing and sissification but haven’t gotten to far into it as of yet. I’m really hoping to be able to visit the store soon or even order online to get my first sissy outfit. I’m pretty shy and consider myself an introvert. I’m not out as a sissy yet but hope to be one day. I’d really appreciate any tips for a beginner sissy that could help me out in finding the right clothing/make up and anything else. I have a chastity cage already and wear it regularly. I’ve been dabbling with wearing panties for a while now and I wear those regularly also but that’s about all I have for sissy stuff so far. I just want to dress up and feel feminine. I’m not trying to pass, I just feel it’d be fun to dress up now and again.

 Chris, welcome to the forum!
 I'm not sure where to start about giving you tips, but figuring out your sizing is a good place. If you are buying from a somewhere like Janet's they should be pretty good at helping get clothes which fit you properly.
 Also it depends what your goals are, and if you are like most of us you have no idea where this is going to take you. I know I didn't, and in a way still don't though I now have self acceptance of my crossdressing needs and can enjoy it much more. Maybe you will get interested in going out to meet other CDs or just out in general as you go further into this.

 There's a wide range of you tube tutorials about makeup, or if you get to Janet's they can help. Stores like MAC, Sephora and others are very good at helping you with makeup though of course they are expecting you to buy some too.

 Thrift stores are great places to find cheaper clothes to experiment with. My experience has been of total acceptance when shopping for women's clothes in drab mode even with other female shoppers around but one does have to achieve some kind of comfort level to do this.
 So give it a try!

 One trick to figure size, is to measure your waist fold the tape measure in half and see how far it comes up your arm from your fingers, remember the spot and you can quickly figure out if that skirt's waist will fit you. Ditto for your chest.
 Look for clothes with stretch as well, that helps a lot too.
 Amy

Thank you for the info! Seems like it will be very helpful. Yeah, I have no idea what my end goals are with this. I just want to get into some girly clothes in private for now and probably just go from there. I’m not too worried about shopping for the stuff, yeah it might be a little embarrassing but I’m okay with that, i assume it’d get less embarrassing the more i do it I’d hope. I’ll definitely need to measure for sizes and for sure will have to watch makeup tutorials because I don’t know the first thing about applying make up but I’m willing to learn all of that stuff. Maybe when I get more comfortable, I wouldn’t mind meeting like minded people or other CDs in person, but for now I’m just super shy and will do all of this stuff in private. 

[krisroq]

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