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Hello there my name is Sam. I'm 24 years old from New York and I just started crossdressing 8 days ago.
How it started was on the 18th of August after work on my way to my girl friend's place which is like 20 minutes from work by walking it started pouring rain and I did not have an umbrella at all so I got all soaked from the rain. So when I arrived to her place I took a hot shower and I did not have any spare clothes with me since I was not going to stay over for the night so my girl let me borrow her clothes. I even jokingly said fuck it let me try on your underwear too and she let me wear me extra pajama which was a nightgown and her panties. So I stayed over for the night since I was kinda embarrassed and late. So the next morning when I woke up I told my girl that her nightgown and panties feel amazing and that is when she said wanna try out my other clothes jokingly and I said sure and they all fit great except for the bra since they where huge in the chest area. So my girl was like wanna go shopping your own jokingly and I said sure why not since you said I look great in them and way better than male clothes. We went shopping for own girl clothes and ever since then I'm not embarrassed wearing female clothes and I'm actually proud to wear it in public which my girl don't mind since we are the same size. I'm size L for the top, size 8 for the bottom and 34AA while my girl's only difference is that she is 34C.