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First time cross dressing


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I never had a chance to cross dress when I was a child, I always wanted to, but never really had a chance. I did once, and tried some sort of shorts/skirt . I remember it being the very interesting exciting thing for me back then, but I never tried again in fear being discovered. 


This last week I seen a dress I really like, it was awful feeling. I wanted it so bad I cried. After a while to, I broke down and bought it. I was so scared that my parents would find out. So I ended up watching for the Postal Service like a hawk. Thankfully, I got it without issues.


Putting it on for the first time was exciting, getting it on wasn’t easy though. It was a two-piece. Strangely, the dress shirt fit just fine, though the sheaves were a little short. But the skirt is problematic. The waist and bust were way off, it wouldn’t fit. Then I realized I size myself wrong. I read the tape, major upside down , I thought i was 34, on the waste, but I was really 43. I pretty sad and was about to cry, then discovered there was a zipper. It opened  just enough. It Allow me to slide it on, unfortunately, I can’t ever zip it and there’s clearly a large gap opening under my arm where it’s unzip. 


Wearing it was strange, I thought I would cry or be super excited, but it was none of that. Instead, I felt content. like if it was normal. Maybe a little sad it didn’t fit correctly, plus the skirt length was post to be between my ankles and knees, but instead, it’s right above my knees. This kinda made me laugh a little as it made it look like a short dress. it didn’t bother me too much, but I would still like it longer. 


I would love to wear it more, only if my family wouldn’t freak out about it, I would leave my room with it. Thought even if it was ok I probably still wouldn’t do it until I get fix and resize haha. I learned a lot from this, i ordered that dress off Etsy.  Next time order from there I should see about contacting the seller as if they can do custom sizes. Then I can just have it sized to me.


 As what I’m gonna to do with it now I was thinking of sewing and modifying it. I was reading about resizing dresses, I think I can add enough to it, so it can fit correctly. Thought, it won’t fix the length of the skirt, and my fix might be visible if I lift my arms. I figured worst case scenario if I ruin it I’ll just contact the seller I got it from and see if they can do a custom size. Besides learning this is a good idea for me, as I’m very large. I doubt I’m going to finding stuff in my size very often, and I don’t exactly have piles of cash laying around to pay tailors.


 Oh another Funny thing is I thought this dress would take a long time to get to me, so I order other skirt and shirt, but I got that skirt the same day as I got the dress. So I put that skirt on under the dress, to see if it helps with the length. It doesn’t look too bad, the colors don’t really match, I have to see about trying another skirt that matches better.


Now I want more clothes haha, I have a shopping list of things I want now. Sadly, overextended myself this month so I need to lay off on the spending. And I might be moving soon I need to save money. but next month I can see about getting some more

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First welcome.

The first time I got the nerve to "crossdress" was what cracked my egg.

Yeah, if you are fairly large and male bodied it can be a challenge to find clothes that fit right.  It might take some experimentation.  Some websites have charts where you can look at your measurements and find a better size.  I tend to prefer longer hemlines myself, but I am a bit older than you.

Thrift shops are good if you have access to them.

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Welcome to the forum!! I found Amazon to be a good source of inexpensive but well constructed clothing as I began to experiment with sizes and styles. Plus, many items can be returned/exchanged if they don't fit. The key is to make sure you know your measurements. You can do a search to find how to measure yourself online - but get a fabric measuring tape, not a metal one used for construction. Once you know the key measurements, you can order with more confidence.


Beware of items made in the Far East, though. They are often sized smaller than the actual marked size. That's where knowing your measurements are critical.


Again, welcome!! 

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Hi Maisy nice to meet you.Yes you will have learned a great deal from that first shopping experience.It's hard to resist jumping in the deep end when we're not ready or prepared and it usually costs us money! Take your time and work on the basics.Whatever problems you encounter there's nearly always a solution or part solution that gets us through.I remember an adage from my chess playing days.'If you find a good move look for a better one'

Good luck in your journey

Love Keera

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SHEIN and TEMU are great places to shop at. They are cheaper than most American stores. The problem is that it is shipped from China so it'll take a while to get. Their quality is amazing. If you get a leather or pea coat don't expect much. It'll just be the liner but you don't pay no were near the prices that you would pay either. Building a wardrobe is fun but also challenging especially when your 6' tall and wear a size 13 women's shoe. Look for maxi dresses. Mid dresses aren't as long but they work for me. I still have yet to find tights that fit me due to my height. I thought I would get some thigh high socks. Congratulations on a big step achieved. 

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3 minutes ago, Ashley0616 said:

I thought I would get some thigh high socks.

I love these, and wear them all the time, when the weather is cool enough.

There is a brand from China on amazon, that reach all the way to my crotch and I'm 5'10" and my legs are fairly long.

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16 hours ago, Maisy said:

I felt content. like if it was normal.

@Maisy, these were my feelings also … the first time I tried on a dress in my youth, and then nearly 50 years later when I finally decided I needed to follow my heart.  I am sure you won’t need that much time.

Be careful, but enjoy this time of self-discovery.  It only comes once, but some day you will look back on it and realize it was magical ☺️

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I remember the first time I bought myself a skirt. I found two, actually, on a WalMart clearance rack ($5 and $2). I guessed on the sizes and was close enough (14 fits best). Can't describe the electric feeling I got just from putting it on for the first time when I got home. (I have the $2 skirt on right now as a matter of fact - the most comfortable clothing item I have, alas I have to hide it under sweats or something much of the time).


Like Ivy, my egg really started cracking at this point. And I kind of went off the deep end buying everything in sight (went to about every WalMart in a 20-mile radius last fall hunting their clearance items, then went hog-wild on Amazon, now I've found a few thrift stores).


One note about Amazon, at least where I live (bigger city). You can have them deliver most items to a place like Kohls or Whole Foods, and you can pick them up there. No need to sweat other folks in the house intercepting your deliveries! I take advantage of that all the time. Alas, maybe one day I just won't care who notices but it comes in handy.


Anyways, enjoy this time of discovery. It really is fun and rewarding...



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11 hours ago, EasyE said:

You can have them deliver most items to a place like Kohls or Whole Foods, and you can pick them up there.

I didn't realize this.  But I have noticed that they do have "pick up points" or something.  Thankfully for me it's not an issue.

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