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I'm A Boy Who Likes Wearing Dresses

Got to wear a dress an entire afternoon and evening after work on two days this past weekend... It was so nice. Since my family was out for the weekend I didn't have to worry about getting caught, (they don't approve, end of the question.) and it was stress-free relaxing.
It was a white knee-length cotton dress with straps- a simple design embellished with red embroidery all over. I wish I could have had a satin dress, my favorite fabric, but in my small apartment I can't hide the garment if I did own one if my own. And so I am limited only to what is in my sister's closet, and she has no satin dresses. It was almost too small for me though, making it almost too hard to breathe, but that snugness felt almost like what I'd imagine a corset to feel. I still like the dress though... It's one if my favorites in her wardrobe.
I do not do the whole shebang (undergarments, makeup, etc) when I wear dresses, but even donning just the outer garment made the whole time nice and relaxed. I can't wait until the opportunity strikes again, or until I can actually get my own place!
ArishMell · 70-79, M
I can empathise completely with the story. My first experiments in this were when I was still living "at home" though my brother and sisters had moved out. I don't know how my parents would have reacted - I was in my 20s - but I think they would have been rather shocked and very embarrassed if they knew, so my explorations of assorted stacked up spare clothes was when they were away for an afternoon or evening.
TalAlyss · 31-35, T
@ArishMell If you didn't notice the timestamp, this story was about five years ago... I'm happy to say that since then, things have gotten a little better! I still live with my folks (so I gotta be careful when I can wear things), but that dress I mentioned is now mine (my sis was about to send it off to be donated) and I also have so many other dresses in my collection! Still gotta hide the clothes, though 🤷‍♂️
ArishMell · 70-79, M
@TalAlyss I must admit I'd not looked at the date! Still , it's good to read things have improved a bit.
SilkandLace
Get a place of your own, and do the whole shebang....you want stress-free and relaxing? Nothing could be finer! :-)
4billi
panties or a slip would make the experience better if you can't do it all
serinalynn
a quick note, Stop wearing your sisters dress, and go to a J.C. Penny or a Macys store and look through (not knowing your size) the clearance areas Average size 0 thru 14 plus sizes 0X thru 4X. I was in a Macys yesterday and got a nice summer dress for 50% off. I paid $34.50 plus tax.
bobbylee111
Dont know where you live, but JC Pennys is having big sales this weekend for back to school clothes too.
bobbylee111
What you do is buy a dress in your size and stash it in the back of your sisters closet. You can even pull up the corner of carpet in the back of her closet and hide things there too.
bobbylee111
Oooh that is a splendid Idea, never thot of that one. I've even put larger sized panties in the bottom of moms lingerie drawer and she never knew too.
schoolgyrlKaren
Eventually you will build your own collection.

 
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