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First Time Wearing My Sister's Clothes

Compared to some of the other stories here, this is pretty uninteresting, but I'm sharing it nonetheless.
Summer is winding down, and my sister just went off to college. Thankfully, she left a decent amount of clothes behind at the house. I am 15 at the time. I've always wanted to try cross dressing. It seemed like it would be great, and I'm already kind of girly so I wanted to try looking the part. My parents were at work and the house was empty this day. I remembered my sister's clothes, and I snuck my way into her room. Even though the house was empty, I still felt very nervous and cautious. I looked in her drawers and found panties, bras, jeans, shirts, and everything I could want. So I undid my pants and underwear and sought to replace them with female clothing.
First I went through her underwear drawer. I felt like such a pervert for doing this, looking through and trying on her panties, but I wanted to, and nobody was around. I took a pair of nice, cute looking panties and slowly slid them up my legs. In the past I had read many people's experiences cross dressing, and they had said panties just felt so good. I can definitely attest to that. They obviously aren't made for men, though. My sister was also a bit smaller than I was, so it all felt a bit tight. It didn't help that I was getting an erection, either. But I tried to ignore it, and I just stood there, looking in the mirror above my sister's dresser. I was wearing panties. They were tight, but comfortable. My butt was hanging out a little bit, but it wasn't annoying. They were just blissful. It felt bad because I shouldn't be wearing my sister's panties, but it felt good because it was just plain wonderful. The only annoyance was the bulge in the front. That was annoying. But I pulled my shirt down, and it became invisible, and I felt kind of like a girl. I certainly didn't look like a girl, though. So I took a pair of tight athletic pants (I think... I don't really know much about girls' clothing) and slipped them on. They were tight, but extremely comfortable. I looked only at my legs in the mirror, and they looked like girls' legs. I looked up. Boy. So I delved into another drawer.
I found a cute shirt and tried that on. Again, my sister was smaller than me, so it was tight, but it formed my body a bit. I even took on a bit of a girlish form. I was just so happy. I smiled and looked. I didn't even really think about trying on a bra. It just didn't seem like it would work. So I just used what I chose. I tried on another shirt, then went back to try some other panties. I was in heaven. I started getting paranoid about when my mom would get home, though, so I changed back into my clothes and put everything back as it was. On the way out, though, I checked her closet. There were dresses and shirts and wonderful things. I was done for the day, but maybe on my next trip back, I'll do more and try more and actually try to fit the part. Sounds exciting. :)
I just wish I had a wig. My boyish short hair just doesn't fit with the female body I'm trying to make. I'll try doing some things to it, though. In all, my first experience cross dressing was wonderful. I was really paranoid about being caught, but otherwise, pure bliss. If you read this whole thing, thanks. :)
deleted deleted 26-30 5 Responses Aug 25, 2011

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Great story. You'll have too keep us informed on your next adventure.

I started dressing in my sister's clothes when I was 11, 36 years of pure happiness. I must say, I did get caught a few times as a teen by my sister while in her clothes or going through her dresser. She wrote it off as a teen going through puberty. Till recently going through my divorced, I came out to my family and friends of my lifestyle. My sister was very surprised I still dress and we have had some long talks on it.

lovely story you now know you have a feminine side so explore those emotions and accept them gladly

Yes I will never forget the very first time I crossdressed. I was 12 years old and on one of my winter breaks I found myself home alone. I finally got up enough nerve to go into my mom's panty drawer. I was so amazing at what was inside of there. I grabbed a pair of red, silk, bikini cut Victoria's Secret panties. I rushed into the bathroom and I put the panties on. After they were on me I felt so amazed. The soft satin felt so cool and comfortable against my skin. After that every time I got a chance I would try on other pairs of her panties and dresses and bras from her closet. I never got caught doing this.

Sure did read the whole thing, and welcome to the family! I'm both excited for you because I remember my first years of discovery about the same age, and terrified for you if you're still doing this at home and still getting into your sister's things. You stand to lose so much if you get caught -- your sister's trust in you being the main thing, and your relationship with your parents could suffer (or improve... not everyone has parents who freak out at discovering their son is different).<br />
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So that was... what, 4 or 5 years ago? What has changed since then? If you're like me (and a lot of us), you've probably had a tough time getting a handle on just who and what you are. Remember, there are no wrong answers and no matter what anybody says, there is no required "next step". If you're happy with just the panties, great... if you also like dresses or skirts, fantastic. If you want to try passing as a woman... good for you, but be VERY careful; men don't pass as well as they think they do and most of the world gets really angry at finding out they're in a live reenactment of "The Crying Game".<br />
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You don't have to act like or think like or feel like a woman if you don't want to; plenty of us just like the clothes and are happy still being all man under the satin. Conversely, you also don't have to stop at the dressing if you do feel like you need to find your inner female. Just take a long look at yourself and what you like and don't like, and go with what's right for you.