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Live in GF was asleep one night and I went into bathroom and put on all clothes that she was wearing that evening. Tight black dress, lingerie, heels. Then i put on her makeup and hung out for an hour when she was asleep.
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LOL ! Yes Jennifer there were rich friends that had the little pool houses and would nake old bathing suits available for guests ! Yes at least twice I took my time back there trying on the cute two piece foloral bathing suits ! So Fun ! Hey I was a guest so it was ok right ? LOL
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Anytime I apply makeup. The more makeup applied the bigger the risk because it can't be torn off quickly like clothes can.
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Once I went into my sister's room when she wasn't home. I took 1 of her bras and tried to put it on, with no success. I lost interest very quickly and thought to myself "Girls sure wear a lot of different things from boys." My crossdressing journey did not start until much later in life.
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Probably my mom's pantyhose. I was always afraid I would damage them and she would know she didn't do it.
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I've borrowed a few article of clothing, but this is one of the riskiest :
I used to work as a student painter, and we would paint the interior of people's homes. At one house, the daughter was a real knockout, so when she was out and the parents were downstairs, I snuck into her bedroom and took a look at some of her clothing, I didn't take anything but she had a white see through body suit.
Another time, we were working on this person's house, and he stepped out. By chance I was the only one left in the house, so I went to the daughter's bedroom and found a really nice sexy one piece swimsuit. I quickly locked the front/back door, and tried it on. I saw a picture of her and was pretty good looking, a little heavy set though. Which meant her swimsuit was a little bit bigger on me.
One house we worked on, the g/f of the son moved in with his family. The son was not home, but the g/f was. She didn't unpack, and had all her clothes still in a white garbage bag. As luck would have it, everyone was in another part of the house, so I quickly went thru the garbage bag and found a really nice one piece swimsuit. I smuggled it home and tried it on. It was nice and tight, and felt really good. I had every intention on keeping it, but my conscience got the better of me and the next day I returned it. That was risky, as I noticed she dumped all her clothes from the garbage bag on the floor the next day.
back when I was young and stupid ...
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Risky things i put on were my sister's swim suit,and her panty hose, which i ruined badly. I am sure she must have noticed, and suspected me. My mom's nylons, too. Noone said what happened, but my mom did want me to go to a "shrink" about that time, and i would not go. I think they knew.
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I was very naughty as a child tried on most of my older sisters underwear, all of my mums nice underwear, dresses and skirts as well as quiet a bit of my aunties and cousins. Needless to say caught out numerous times and made to promise not to do it again.
But the most risky was when I was around 17 staying with a friend while his parents were away and had a bit of a party with friends. I got drunk early and went to bed early in his parents room. Inevitably went straight to find his mums underwear drawer and once found it pulled out a lacy little baby doll and so quickly in to that and in to his parents bed. Scared to death when my mate came to check on me never pulled a duvet so tight to my neck in my life!:o
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Hmm. as a pre-teen and teen I only had my mothers clothes to wear, i never touched her undies however. I house sat for my friend and dressed up in his mothers clothing and had the run of the house for a week, it was glorious but riskiest I'd say....Aunt and Uncle asked me to house sit when I was a teen. I went about putting on a lot of her clothes when they were gone and stayed dressed for hours but when i had a moment alone and before they left I was able to put on her panties, bra and pantyhose from the hamper in the bathroom in anticipation of them leaving as I'd get down to business and dress including makeup. I had these items on and was watching tv when they came home to make sure I was all set w/the home etc. I was sitting on the couch in male clothes and rock hard underdressed waiting for the green light to dress, they sat feet away for what seemed like eternity. If they'd asked me to get up and hug it'd been game over as they'd feel the bra strap.
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Ashlee the bra has always worried me when I thought about underdressing.
I wonder how many of us had trouble getting out of dresses when the zipper got stuck ? LOL
