Kinda taboo but it made a deep impression on my sexuality.
I was 17 and my brother was 15 when this happened. Band practice was cut short after school because of some kind of emergency that our director had to deal with, so I went home thinking I could get a little homework done before dinner. I went upstairs to my room and I began to hear somebody in there. It was a boy's voice and I recognized it as my little brother, Joe.
When I peeked in, I was shocked by what I saw. My little brother was wearing my new bra and panties that I bought from Victoria Secret and I could tell he was stretching the panties out pretty good too if you know what I mean. What I heard was him moaning a little and calling my name. I watched him for a minute touching the bulge in my panties and the right cup of my bra. I could see that he had stuffed the bra cups with stockings and my underwear drawer was wide open in my dresser.
He picked up something from my bed and I could see it was one of my dresses. He held it up to him and kind of twirled around once before he pulled it on over his head. I was surprised to see that it fit him pretty good. Joe and I were pretty close in size but he was beginning to grow too.
Anyway, he reached behind his back and zipped the dress up and then sat down on my bed and put on a pair of mom's older shoes that she doesn't wear much any more. He stood up and walked around the room a little bit, admiring himself in the full length mirror that I have there.
It suddenly occurred to me that he was doing pretty well in a pair of heels. I mean like he had worn them before. Most guys look pretty awkward in heels but he made it look as good as most girls.
He continued to rub himself through my dress and panties and was obviously having a good time. He stopped for a moment and walked to my undies drawer and looked for something else. He pulled out my little white half slip and put it on and pulled it up under the dress and then smoothed the dress down again, walking a bit more. He was rubbing the front of the dress again and seemed to enjoy this a lot.
In fact, he was enjoying it so much that he kept at it and started to breathe faster. I knew that he would be shooting his semen soon and I didn't want him to mess up my new lingerie or my dress with it, so I pushed the door open and walked in.
'What are you doing?'
He looked at me in total shock but didn't or maybe couldn't stop what he was doing. He let out a loud moan and stood stock still as he let go his load in my clothing. The thing is, I was very mad at him for messing up my things but I was very turned on too. I realized that my panties were definitely soaked and I needed some personal time too.
He stammered and tried to apologize but then he started to cry. I hated to see a boy cry and I stopped and then hugged him.
'It's all right, just I hate to have my new things all messed up.'
'Oh, I'm so sorry, Rach. You have the prettiest things and I just couldn't resist trying them on. I'll clean them up, honest. Please don't tell Dad. He would kill me for sure.'
He was right there and I knew I had him. Perfect blackmail material for when I needed him to do something so I could skip out with my friends.
'Oh, Josie, I was so mad when I saw you in my things but stop crying. I won't tell anyone, I promise. Just you have to get out of my things and clean them up.'
I reached behind him and unzipped my dress and let it fall from his shoulders to the floor. Then I realized what a mess he had made. There was a big wet spot on the slip and I could see some wetness on my dress, too. I pulled the slip down and he didn't resist. The panties were a soaking mess, but his cock was still hard. It was getting harder, too as I watched.
'You like this, don't you little sister?'
He moaned and I decided to tease him a little more. I started to touch the cups of the bra and he really moaned. He was very turned on at this point and he had just had an orgasm! I was wishing my boyfriend was that quick in getting hard again.
I did something very bold. I touched his cock through my panties, through his wetness and everything. He twitched down there and moaned even more. I was no stranger to hard cocks, but this was a very kinky first. Touching my brother's cock through my panties on him. I realized that I was very very horny and needed some relief too.
As I played with him through my lingerie, I guess he realized that I was needy too. He put his hand under my school uniform skirt and slowly ran it up to my own wet panties and began to stroke me along my pussy lips and then pushed into the slit to touch my clit. I pushed back and he responded to my need. At the same time, I continued to stroke him through my panties.
It only took a couple of minutes of this and both of us were having sweet orgasms by each other's hand. I was amazed. I never realized that I could be turned on so much by my bratty little brother and I never dreamed that I would find it so sexy to see a boy in girls things.
That began a period during which we would masturbate each other, Josie would always wear girls things (only what I provided. I didn't want my best lingerie messed up.) and we would get each other off sometimes as much as once a week. There was a week when mom and dad had to go to a family funeral out of town and Josie and I played dressup all week they were gone. It was amazing! It mostly stopped when I went away for college, but there have been a few times when we were together with nothing better to do and I found some things for him to wear...
I'm still turned on by a cute guy in feminine things. I've tried getting boyfriends to just try on my panties but only one so far was into it. We had some hot times, but eventually broke up for other reasons.
As for my little sister Josie, I sometimes send her gifts from Victoria Secret.