omg lesson#74: crossdressing tips: smg style...

i have a wee fondness for crossdressers. i honestly don't understand what the big deal is but most crossdressers who 'come out' to their spouses are vilified and shamed. i'm not sure why that is b/c it's just clothes and a bit of a make up and frankly, if you did it for halloween, no one would blink an eye.

i just am sorry that so many men seem to have a complex about their crossdressing fetish. i don't think there's anything wrong with it and it's probably one of the most innocuous fetishes i've ever been exposed to. and, i find most crossdressing fetishists are pretty damn respectful of their partner's needs/wants and feelings about their particular fetish. of course, #notallcrossdressers; i'm just speaking from my experience.

in any event, some crossdressers do it badly.

i'm not talking about sissies, drag queens or those who are actually looking to make a transition from male to female permanently. i'm just speaking of the men who identify as men as a gender identity and simply like to dress in feminine clothing every once in awhile. you're not about to do anything permanent so you have some stuff to kind of disguise/address to get the 'look' you want.

1. let go of being able to 'pass' as the goal.

i think it's defeating sometimes to always want to look 100% like a woman when you're all dressed.

let go of that notion. it doesn't help build your confidence or feeling good about yourself. you want to feel good about what you see in the mirror. you are you. no matter what you wear, you're still the person you are, on the inside. feeling good inside will radiate to the outside. and honestly, find people who are supportive of you as a cross dresser. if everyone around you is negative about cross dressing, you can't help but be influenced by that negativity. find at least one person who is positive and who you can share a little of this with.

2. problematic 'male' areas.

there are probably 3 areas that are particularly problematic for men that are permanent fixtures. but...they can be addressed in temporary ways.

  • a. penis & balls: the most obvious but you can tuck & tape or choose clothing that will 'hide' them. 
  • b. body hair: we all have hair but men tend to have more and some clothing just doesn't look 'right' if you haven't shaved. this may well be personal preference but i'm just going to say if you want to wear a dress and stockings, aesthetically it looks better when you shave. and i would avoid waxing b/c shaving is much more temporary - again, personal preference really. if you're waxing, go to a reputable pro. it's less messy and gives great results.

c. adam's apple: some men have a more pronounced apple and so may never be able to disguise it entirely. but...you can use contouring makeup or use clothing like a pretty scarf, turtlenecks or high necked blouses to address it. my preference would be a collar but just b/c you're a cross dresser doesn't mean you're submissive and this is just my personal preference...

3. hair and make up.

make up is an art form and the trick of it is to make it look like you're not wearing much at all. and avoid the 'too fussy' hair.

this is not the 80's where caking on the stuff and making it look like you've caked it on is the goal. or using massive amounts of carcinogenic hair products for that dynasty look. uh uh. you want to make it look like less, rather than more...

as with most things, you need to look at overall facial structure and how you want to accentuate things. that being said, if you have perpetual 5 o clock shadow, you could address it with foundation or let it ride. either works. i know a great cross dresser who dresses beautifully....and never shaves his rather bushy moustache :)

my best resource for this is how to feminize your face. you don't need to do all of this. it's just a resource so you can pick and choose what you like and want to do.

4. finding the right clothes for your body type.

if you're going to make the investment in a small wardrobe, choose your pieces carefully for what works for your body type and makes you feel good.

this can be tricky b/c men seem to have really shitty taste in women's clothes for themselves. for some odd reason, big flowery prints and really out dated clothing seems to fill crossdressing closets. i'm here to end that :)

  • a. dressing to flatter your body type: if you think women's clothing is built for busty and curvaceous....have you seen runway models? most of their body types are fairly androgynous. seriously. in any event, there are ways to flatter different body types. here are some basics for dressing for your body.

  • c. personal shopping buddy: remember what i said about finding at least one positive person? a person to go shopping with, preferably a female identifying person with great taste in clothes, is the ideal shopping buddy. truly, there's a reason lots of women go shopping in pairs or in groups - to try things on and get opinions on how something looks on them from someone else who will give them honest feedback.

  • d. shoes: i know those 4", 5" and 6" heels look to die for! i feel you. but there is a trick to wearing them and walking in them. start with a smaller heel. 2" is a good height. find a basic black pump with a kitten heel that feels comfortable (you likely will need a wide fitting shoe). spend the money on a quality fitting shoe that you can practice in. good shoes are not cheap. and i would not fill your wardrobe with shoes you can never walk in. 

5. online and local resources.

thanks to transgendered folks and a better understanding of gender identity, there are also a growing number of local stores in major urban centres that cater to trans folks that can be a great resource for fittings and advice for male crossdressers.

there are also great resources online from youtube how to videos, to blogs, and everything in between. i will say the trans folks tend to do this best and have the most informative online tools, but look around - google is at your fingertips! i like the articles available on roanyer and cross dresser society but there's many more out there...

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honestly, learning how to crossdress or picking up good tips is easy. the hard part, seems to be, finding self acceptance of this particular kink. honestly, there is nothing wrong with crossdressing. don't be pushy and be honest about it. sometimes, people grow suspicious of those who might be sorting out their own gender identity and that's where good solid work on your own is important. nothing wrong with identifying as a woman or feeling conflicted about gender. but be honest about that - with yourself and your partner(s).  crossdressing is just a kink but if it means more than that to you, then work on that either through self reflection or work with a kink friendly therapist. because being dishonest is what people often react negatively to.  

and with all things, if you've only found people that have made you feel bad about yourself, find new people to surround yourself with that are more supportive. ultimately, it's you who needs to be okay with yourself and what you like. but i find it's just a wee bit easier with someone who's supportive and understanding. be kind to yourself and dress to make yourself feel good and enjoy your kink :) there ain't nothing wrong with it as long as you're being honest and not being an asshole :)


Dec 21, 2019

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