I think I fucked up my step brother that one summer when we were seventeen and nineteen, me being the older. It was just one of those things that teens do. Play around not realizing that what they were doing could and in this case, did have serious consequences when we grew up.
It was a sweltering hot summer and Bill and I hung around the pool most days. Sometimes we would have friends over but most of them had left the small town we lived in with their families.
Our own parents who had adopted us when we were just toddlers decided that I was mature enough to look after my brother for two weeks while they visited friends in another state, bad idea. I was not mature as it turned out. In fact, I was a walking talking sexual disaster who didn’t know what I wanted, who I wanted or how to get it.
The problem was that I was the school nerd with thick glasses and mousy hair. I hated makeup or to dress like the social norm dedicated. That didn’t mean I didn’t have urges, God, I did, but being the way I was no guy looked at me twice, and most not even once. I got my pleasure from my fingers and watching videos. Yes, it might be a shock for you but women do watch porn, and in some cases, like mine, a shit load of it and always checking out new things.
Back to Bill. He was the opposite of me, popular, good looking in a feminine way. His skin was soft; he had a soft kind face with full lips and a straight nose. His kind brown eyes made the girls melt and if that didn’t do it his long eye lashes did. He was a sharp dresser and spent most of the money he made at his weekend job on clothes. He didn’t have much of facial hair so he kept his face clean shaved and even used skin creams, which I thought was hilarious.
Anyway, that day I was lying on my sunbed watching him. He was a few feet away on his back with his sun glasses on and I think he was dozing. My eyes wandered over his body looking at his muscle tone and the way his cock was outlined under his speedos. Yes, I know, looking at my bro’ that way is not okay, but I did and had for a couple of years.
We were close. He didn’t seem to care at first, but last year when I went into the bathroom while he was taking a shower to use the toilet he got upset. When I asked him why since it hadn’t bothered him before, he said, “Because we are not kids any longer."
Bill turned over onto his stomach showing off his tight pert ass. I wished mine looked like his. Not that mine was ugly, but his was just so fucking perfect.
I sighed and watched as my nipples grew hard under the bikini top. I gently squeezed them and let go of a sigh. One hand slowly moved down my tummy which had a film of sweat on it until my fingertips reached the bikini hem and slid in.
I had a shaved pussy. I thought it looked good so as my fingers run over the silk soft skin I shuddered. I wanted to get off right there and then and I was about to when Bill said, “Hey, get us some drinks will you.”
Thank lord for that, or I had come right there. I got up and when I came back with the drinks Bill was sitting up rubbing his eyes.
He turned to me and reached for the glass I was holding. His eyes were not far from my boobs and I knew he could see my hard nipple poking at the fabric.
“I guess the fridge was cold?” he said and chuckled.
“Yeah, I guess so.”
I sat down and we drank in silence. When I put my glass down I said, just to give Bill a hard time, “You know, you are such a girl.”
“Fuck you, it’s not feminine to take care of yourself, you should try it you know. It might make you get a guy.”
I stood up, “I might not dress the part but I have a good body.”
His eyes drifted over me from top to bottom. “I guess. I have seen worse.”
“Admit it, if I wasn’t your step-sister, you’d fuck me.”
Bill blushed and looked away.
“C’mon, say it,” I continued.
“Let it go, Haley.”
***
There had been a tension between us since the previous week when our parents had still been at home. I had walked in on Bill jerking off on his bed while watching porn on his mobile. He was so engrossed into whatever he was watching that he didn’t notice until I was standing by the bed. I had enough time to see his cock was hard and already oozing pre-cum before he hid it under the sheet. He had told me to get the fuck out but before I did, I said, “Now I know why the girls are after you, it’s quite the cock you got there.”
“Bill...Bill! Look at me.”
He turned and at the same time I pulled up my bikini exposing my firm C cups.
“Touch them,” I ordered him.
“No.”
“You are such a prude, a damn pussy!” I screamed and walked into the house.
I was fuming when I closed the door to my room. What the fuck was wrong with him, I had a nice body. I was there and available to him any time he wanted, but no, he had chickened out like a damn little girl. When I realized what I had thought a smile grew on my face. I quickly turned on my laptop and while it booted up I made sure the door was locked. Bill had a way of coming to my room to apologize after we had fought but now wasn’t the moment to forgive him.
I opened my favourite porn site and made a search for Sissies. I had seen it before but hadn’t paid much attention to it. Grown men wearing girl clothes wasn’t something I got turned on by but seeing Bill in a pair of cute undies was something different. I bet he would look quite sexy in them, but most of all, it would be degrading and I had had enough of him pushing me away.
As I watched a few videos I realized I needed more than just panties, skirts, bras, stockings, wigs, and make up to turn my brother into a young woman. I needed a strap on so I could fuck his lily white ass when the time was right. Lucky me our parents had provided both me and Bill with credit card so I went in search for a site that would deliver in twenty-four hours.
I couldn’t wait to put my plan to work. When the strap on was in the mail I clicked to where the site offered fake boobs and bought a pair of nice C-cups for him, similar to mine but with brown nipples instead of pink. I didn’t care if my parents found out about my little shopping spree. I doubted it since the site promised the items would be billed as something other than sex toys and fake boobs.
After that was done I took a shower, got dressed and went down stairs where I found Bill making a sandwich. When he heard me he turned. “Hey, I’m sorry if I upset you, but you know I’m not interested in having sex with you. I could ask one of my friends to do it if it’s so important to you.”
I cocked my hip and drew my fingers through my hair, an act I had never done before and it got its intended reaction from Bill. “Hey, do that again.”
I did and he said, “Wow, that almost looked sexy. You need to learn more of that and change your wardrobe. Then the guys will come knocking on the door.”
I smiled at him. “I’m actually going shopping now, I’ll see you later.”
******
The mall was quite busy it being a Saturday afternoon. I found my way to the lingerie shop and when I walked in the pretty attendant looked down her nose at me.
“Yes?” she said, like if she was surprised to find me there.
“Yeah, hi, I need a few things, could you help me?”
She looked me up and down and a smile grew on her face. “Total makeover?”
“You bet!”
Half an hour later I walked out with several thongs, garter belts, stockings and bras, all of them in white, black, or pink.
My next stop was a shop which I had only seen from outside. It catered to teen girls and had all the latest fashion. When I walked in I asked the attendant to help me and when I left I had problem carrying all the bags. I had bought a few skirts, heels, tops and dresses.
******
Bill didn’t drink, not a beer and never a shot, his drug of choice was a joint once in a while and having our parents away meant that he lit up every night. One thing that I loved about Bill being high was that he just said yeah to everything. I would make him clean my room, do dishes, cook meals etc. Anything I said he agreed to with that stupid drug infused smile.
So, that evening when he was nice and high on the terrace I sat down opposite him.
“Hey, Haley, what’s up?” he slurred.
“Nothing much. I read an interesting article in a magazine and wanted to ask you about it.”
He laughed. “I don’t think I’m in a state of mind where I can give you a serious response to anything.”
“Well, actually, since what you smoke opens your mind it might be the best time to ask you.”
He took a long puff and slowly let out the smoke while he squeezed out the word, “shoot.”
“Okay, so this article says that in each man there is a woman and in each woman is a man.”
I stared at me blankly. “What?”
I sighed. “It means that deep inside us you have a feminine part and I have a male part.”
He began to chuckle. “That’s some weird shit, Haley.”
“Yeah, I thought so to, but then I remembered you and how you like to take care of your physical appearance, you know, the creams and shit you have.”
He slowly nodded, “Yeah, I can see that. So what, I’m a girl now?” more chuckles.
“No, stupid, it just shows that deep inside you there is a woman.”
“Uhu-hu, what about you, will you grow a dick anytime soon?” this time he laughed hysterically.
“Yeah, maybe, and maybe one day I walk into your room holding an eight inch cock in my hand, would you like that?”
He stared at me and there was a complete silence in the room for a few seconds. I worried that I had gone too far but then suddenly he began to laugh again pointing a finger at me. “You could be Hank, yeah; Hank is a good name for you, close to Haley.”
I nodded, “Hank. That sounds good, I think I’d make a great Hank. What about you, Bill, what’s that woman hiding inside you called?”
I could see his mind working, but it took so long I decided to help him. “What about Tracy, or maybe Kelly?”
“I know a Kelly, she is a sophomore and hot like shit but stuck up,” he said.
“There you go; you’d make a perfect Kelly.”
His eyes were out of focus when he said, “so, I’m Kelly now?”
“No, no, you are still Bill, all I’m saying is that inside you Kelly is hiding and I’m sure she wants to come out and meet Hank.”
There was another silence while Bill’s brain slowly processed the words that came out of my mouth. While I watched him I nodded to increase the positive effect of what I was saying.
“Yeah, Kelly would like to meet Hank one day,” Bill said and then his head dropped and he was a sleep.
******
The following morning I was standing in the kitchen in one of the new thongs I had bought and only a long T-shirt covering me. Each time I reached for something in one of the cup boards the T-shirt would slide over my ass cheeks and expose them. When Bill walked in I immediately began taking things out of the cupboards, like sugar, cups, and plates. It didn’t take long before I got the desired response from Bill.
“Shit, I can’t understand how you girls can wear thongs. That fabric between your ass cheeks must be damn uncomfortable. Not that I’m complaining it looks great.”
I turned to him, my nipples erect from him seeing my ass. “There is nothing to it. You don’t even notice it, at least if it’s a good quality thong.” I cocked my hip and tilted my head giving him a devilish smile. “Maybe Kelly would like to try a pair?”
He stared at me for a long time and I could see how he was trying to figure out what I was talking about and when he did his eyes went wide. “Holy shit, did I really say that last night?”
I giggled. “Yeah, you did. I thought it was quite cute.”
“Oh fuck, fuck. I feel so stupid.”
I poured him a cup of coffee and put it down in front of him. Laying my hand on his shoulder I gave it a squeeze and whispered in his ear. “What about it, Kelly, would you like to try a pair, I bet you’d look so fucking sexy?”
His body tensed and then he whispered back without looking at me. “Yeah, I do, but promise me one thing.”
“Sure.”
“This stays between you and me, no one must ever find out about it.”
I kissed his cheek.
