This was the beginning of an unreal but wonderful relationship.
It started when I came home early from school. My last class was cancelled due to my teacher getting sick and no time for them to find a sub. I didn't have anything else to do at school so I went home.
I was 16 at the time that this happened and my little brother was just 14. We were best friends since he was born and we never went through the phase of hating each other or fighting or anything. In fact, he was the best friend I ever had and still is.
Anyway, I went upstairs to my bedroom and walked in, threw down my backpack and my purse and looked up to see my brother in my room. That wasn't anything really unusual as we were always in each other's rooms to borrow a CD or whatever.
This time was different, though, because he was wearing a pair of my panties and holding one of my bras in his hand. The panties were a pink thong and the bra matched them to make a set that I liked to wear when I had a date. It was cute and sexy.
I was pretty shocked to see him that way and he was truly mortified judging from the look on his face. My first reaction was shock, too. That was followed by anger and then I saw the scared look in his eyes and it became sympathetic for my little bro. I had really embarrassed him by the look of things.
It didn't take very long for me to figure all of this out. I closed the door and just went to him and hugged him. He was on the verge of crying, so I just held him and comforted him and kissed him on the cheek.
I began to realize something else. As I hugged him close, I could feel a definite bulge between us. I don't know why, but that gave me a nice little tingle in my pussy and I felt her begin to get wet. I had never had any sexual attraction to my brother before that time, but I definitely knew the signs.
I backed up a little bit and avoided looking down at him, I asked him, 'Do you like wearing girls' things, Ricky? It's OK, I guess. I mean, it's just cloth, isn't it?'
He was very nervous, but when he figured out that I wasn't mad at him, he began to talk to me.
'Yeah, Kel, I like girls stuff. It's just more sexy than what guys wear. I love how it feels on me, too.
'Oh my God, Kel, I'm so sorry. I just can't help myself sometimes and I just have to try some of your stuff on. I'll clean it up, I promise!'
I was embarrassed for him and looked away. I noticed for the first time that there were other things laid out on my bed. There were some pantyhose, one of my dresses, a little slip and a pair of my shoes were out of the closet on the floor. I began to get the idea.
'Ricky, do you like dressing up like a girl? I mean everything? It's really OK with me as long as you take care of my things and don't get them messy or anything. You know that I will always love you best.'
He smiled kind of lopsided at me and said, 'Yeah, I see how pretty you are and I guess I want to be pretty too like my best sister. I love you best, too.'
I hugged him again and kissed his cheek and I noticed again that bulge between us. Wow! That was getting my juices flowing.
I got a naughty idea in my head. I didn't stop to think about it, I just acted on it. I kissed him. Right on his mouth.
He tried to speak, but I just kissed him again and this time I opened my mouth and let my tongue touch his. I reached for the bra in his hand. He still hadn't dropped it. I took it and backed off a little bit and put his hands through the straps and reached behind him and hooked it up.
I didn't make any conscious decision but I just continued to help him get dressed in my things. I looked at the clock and we had about two hours before mom came home, so it was pretty safe.
I helped him get into my pantyhose, my slip and into my dress. Next, I had him sit down and I helped him into the shoes. He picked a pair of old pumps with 3-inch heels. I had him stand up and looked at him.
'You could make a pretty girl, I think. We need more time, though. I need to do your makeup and your hair and nails. It's a good thing you already got your ears pierced. I have lots and lots of earrings we can try on.
'This will be so much fun!'
He stood up and walked over to the mirror to look at himself. I noticed that he didn't have any problems walking in heels. He had definitely done this before!
He said, 'Do you really think so? Could you make me look good enough to go out to the mall or something?'
'Oh, you want to go out and make people think you are a girl?'
He blushed, 'Yes, I've always wanted to be like you. You're such a pretty girl and I love you so much.'
I stopped for a second and then hugged him and kissed him again. A real kiss. With tongue and holding him close and tight. If anything, his bulge felt bigger to me.
'We have to take care of one thing if you want to look like a girl. You have this bulge in front of your dress.'
I kneeled down in front of him and lifted up the hem of his dress and slip and saw the tip of a very nice looking cock peeking out of his panties. I pulled the pantyhose and panties down enough to free his cock and started to stroke it. It felt so nice and it was already beginning to throb.
'Kel, if you do that very much I'm going to make a big mess.'
'So, how do you keep from messing up my things, Ricky?'
He bent over to pick up an old sock on the floor and gave it to me. 'Use this to catch it for me. Please??'
It was kind of crusty and had clearly been used for the purpose before, but I really didn't want him messing up my dress.
I held the sock in my left hand and continued stroking him with my right. He had a nice blob of precum on the tip. I had to taste it. Yummmmm. As good as any of the other guys I'd given HJ's to.
I just kept on until he told me he was going to cum and put the sock over the head of his cock. He moaned as he shot his stuff into the sock and I kept stroking to make it good for him. He shot an amazing load into the sock and I kept stroking until he said he had enough. I wiped up the wetness from the tip of his cock and pulled his panties and pantyhose up, letting his dress and slip fall down again.
I realized what I had done. I had dressed my little bro as a girl and gave him a hand job. It was unreal and probably incest but I loved doing it and I knew that I would do it again. I was looking forward to putting him in makeup and really doing a makeover and seeing if he could be girly enough to pass. I will write about other adventures later if you like.