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When I was in high school I would come home and dress in my Mom's clothes several days a week. She came home early and walked right in on me.

With a deer in the headlights look I said "Oh I was looking for a Halloween costume" To my surprise she was like "Oh what fun, let me help you" So after dinner, she and I spent several hours trying on all sorts of old dresses and suits.

Come Halloween a few weeks later I was embarrassed and also secretly delighted to show up at the youth group costume party.

So getting caught actually worked in my favor. So I was once married, briefly, to a woman. We were best friends and decided to tie the knot.

I thought getting married to a woman would help me get over the issues I was having with my gender because I'm dumb lol.

It was about two years into the marriage when I just couldn't hold it back anymore and began dressing in secret when she was at work. One day she got off of work very early and came home to see me dressed up.

She threw a huge fit, called me "disgusting" and a "faggot" and other derogatory terms. She then took all of the clothes I had carefully accumulated and burned them.

Needless to say, we separated and divorced shorty after and I finally accepted who I am and began transitioning.

Really sounds like you're better off even without the dressing. That's extremely close minded for a person that decided to say, "Til death do us part.

No kidding. She made me feel like an awful person, blamed me being trans for our marriage failing told everyone she left me because I was a "faggot" then a year later randomly tells me that she was having an affair on and off during our marriage.

I was laughed and said "No that makes total sense When I was in high school my mom found my stash of dresses, she flipped out and donated them all to the Goodwill.

She told me if she ever found anything like that again she was going to kick my butt and make me go to a priest to get rid of my demons.

That's hilarious, props for following through with your story. What did you end up wearing? Wow lucky you!

I haven't been caught fully red handed, but a couple years ago my aunt caught me using her mascara when I was visiting.

She gave me a long talk about what to do and not to do and lots of religious stuff in between. She initially thought I was goth.

I gave her a bad excuse for what the real reason was. Then she offered to buy mascara for me. I declined, though in some ways I felt like I should have said yes lol.

That's awesome lol, I can't say that I've ever been caught, but it would probably end bad with me sad, haha. One time, my maternal grandmother was visiting the family, and, the short version is, my grandmother is awesome, and I could tell her anything, so I did, I told her I'd bought a pair of gogo boots.

And she told me she'd love to see them. So I went to my room to put them on, and came back to show them off, but my Dad was talking to her, and I showed the boots and went to take them off, and a couple hours later, my Dad pulled me aside to say I'd embarrassed him in front of Grandma.

I was extremely confused, since Grandma didn't care, and had asked to see them. So, that was probably the turning point in my relationship with my family, the point where I started to realize they didn't love me.

My ex once found my clothes while searching my room when she was convinced I was cheating on her. I had to decide on whether to tell her they were mine and I cross dress or tell her I cheated on her.

I obviously told her I cross dress and she just couldn't wrap her head around it and that is why we are no longer together.

I used to dress after school too. One time I was playing around in a skirt, heels, and gloves when my brother came home earlier than usual.

I changed as fast as I could, but didn't get the gloves off before he saw me. These were elbow length gloves, so it wasn't like I could say something like "my hands were cold".

Crossdresser Outside Video

A walk in the park in high heels Crossdressing

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We went shopping for clothes, dressed up, my friend did my make-up which has never been done so well since, it was sooo good , and we went out clubbing blah blah usual halloween stuff.

Anyway, it turns out I was a bit enthusiastic about the whole thing and my friend took me to one side a few days later and just flat out asked me if I enjoyed it.

She basically said that I shouldn't hide it if I did, and have I considered that I might be a crossdresser. I was obviously embarrassed, but enjoyed the look on her face when I told her I've been dressing up since I'm mostly open about it now.

While I don't dress in public most of my friends know, and everyone I've told has been supportive of me except my mother, but that's another story.

He never caught me dressed, but he did come round one day while I was at work to inspect some building work that had been done.

All my clothes were out in the room that he was inspecting , the storage boxes were open, wigs, makeup, you name it was there for him to see.

He never mentioned it when he told me he popped round, but I assume he guessed. His unwillingness to call before coming round also extended to his builder, who let himself in whenever work needed doing.

There was one time when he walked into the flat while I was dressed it was 8pm! He didn't catch me, but ffs we had words about his lack of respect for my privacy.

She assumed they were my mum's meant for charity. She asked mum about it, who promptly freaked out and threw everything away.

I was 22 at the time, so I was furious. But I was also ashamed, and really needed to stay on her good side so I didn't argue much.

It was really annoying. There was a few hundred pounds worth of stuff, and I only told mum about my crossdressing in the first place so I could store my stuff in her garage for a bit while I moved back in with her.

Damn on that 2 thing you should have called the police. Well maybe not but that is totally unacceptable. I would have done, except this landlord had a tendency to actually get problems fixed unlike all my previous landlords so I thought it was worth tolerating a couple of times a year.

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