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Kelly's Rise and Fall

Haley turns her step brother into a sissy with surprising results.

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. “I promise, c’mon, bring your coffee to my room.”

*****

When we walked into my bedroom I was so excited I could hardly keep myself under control. I wanted to push Bill onto the bed and suck his cock before fucking him with the strap on that had been waiting for me outside the door when I had picked up the morning paper. It was in a plain box, no name or sender details. I had picked it up and run back to my room where I opened it. The strap on was beautiful, and so fucking soft it made my nipples tingle.

Bill sat down at my desk with his coffee while I went over to my wardrobe. Without turning I asked him. “What do you prefer, white, black or pink?”

“Black.”

I found a black thong and when I turned around I had it hanging from my index finger. I slowly walked over to where Bill sat and dropped it in his lap.

“Okay, Kelly, put it on.”

He stared at it for a moment before saying, “turn around.”

I giggled. “No, I want to see how you wiggle your ass and hide your dick in it.”

Bill picked up the thong and then stood up. He quickly pulled down and stepped out of his boxer shorts and then stepped into the thong. As he pulled it up I realized that his cock wouldn’t fit behind the small patch of fabric.

“Oh fuck, look at that, it looks ridiculous,” he said looking down at where his balls were hanging out on either side of the thong and his cock head was sticking up above the fabric.

I looked at it for a while and then had an idea. “Grab your package, balls and cock and push it in between your legs.”

He did what I had asked and the result was amazing. Now it looked like he had a pussy instead of a cock.

“Wow, just look at that, you look so cool,” I purred.

Bill turned towards my floor to ceiling mirror and when he saw his reflection he blurted. “Holy fuck, where is my cock?”

I walked up behind him and let my right hand slide over his hip and down over where his cock was supposed to be and in between his legs.

“Ah, ah, stop it,” he said, but it was too late. His cock began to grow under my touch.

“Let me rub you, please, let me,” I whispered in his ear while digging my nails into the soft flesh of his ass.

“Haley, this isn’t cool, okay.”

“C’mon Kelly, I know you want it. Let me do it and I guarantee you will love it.”

His breathing had become deeper and a moan escaped his lips while my fingers continued to move along his shaft. I knew that if Bill changed position in any way his cock would pop out and I didn’t want that. I loved the feeling of the soft fabric between my fingers and his shaft.

“I think I can make a real slut out of you, Kelly,” I said.

“What, what do you mean?”

I stepped away from him. “Let’s play dress up, okay. First we make you into a proper Kelly and then I’ll make myself into Hank.”

I could see in his eyes that he wasn’t really sure about what was going on so I added. “C’mon, Bill, it’s just for fun, what else are we going to do? It’s raining outside so we can’t be at the pool.”

“Fine, alright, I’ll play along with you.”

I giggled with excitement and then went to work at changing my step brother into a teenage girl.

*****

Even though I didn’t use makeup I still had it. My mother, in her attempts to make me into a normal girl had bought me makeup over the years.

Having Bill sit on the chair I applied a base, then rouge, mascara and a bit of eyeliner. For lipstick I chose a coral pink colour which went well with his tanned skin. Bill’s hair was thick and a bit longish so it was easy to comb into a female style that hung over his left eye and the right side was tucked behind his ear. Standing back I said, “Pout your lips.”

He did and I smiled, he looked perfect. I gave him a small mirror and when he saw himself he gasped. “Holy shit, it’s not me.”

“No, it’s Kelly, do you like her?”

“I guess, she looks kind of hot in a stylish way.”

“Good, now let’s see about clothes. What do you prefer a skirt or a dress?”

He shrugged his shoulders. “I have no clue.”

“Well, there is one thing I forgot. Take off your T-shirt.”

While he did I went to get the box the strap on had come in and from it I took out the fake boobs and a tube of adhesion that had come with it.”

When he saw it Bill’s jaw dropped. “Fuck me, how long have you been planning this?”

“I came up with the idea yesterday, and thanks to overnight mail, we are set to go.”

I approached him and then put the fake boobs over his chest and adjusted them for height.

“Hold them,” I said and stepped back. After making some minor adjustments I glued them to his chest and then we waited a few minutes for the glue to set.

Bill looked down at his tits and said, almost in a whisper. “They look sexy.”

“Yeah, they do. Cup them for me and give them a gentle squeeze.”

When he did I sighed and stared in fascination. With the makeup and the boobs Bill had left and Kelly was looking back at me.

“Right, I think a dress would be nice,” I said.

I went through the ones I had bought and picked a white one that was tight around the boobs and waist and then flared at the bottom. I helped Bill into it and after adjusting the shoulder straps and the fabric around the boobs I stepped back.

And there she was in all her glory, Kelly. I walked around her and patted her ass. When I was back in front of her I said, “So, Kelly, what does it feel like?”

She cupped her boobs and then ran her hands along her sides over her curved hips. “Strange, but I like it.” She looked at herself in the mirror turning to both sides before turning back to me.

“What now?”

I smiled, “Give me one second, and Hank will be right with you.”

I went into the bathroom where I put on the strap on. It took a minute or so to get everything adjusted and I noticed that it came with a small vibrator that was supposed to be inserted into me. When I slipped it inside I sighed. I was gushing wet and even felt a drop of pussy juice making its way down my inner thigh. I had never been so horny in my life.

When I stepped out and Kelly saw me she gasped and sat down on the chair again. “Holy shit, that thing is big.”

I walked up to her and stood so close that the tip of the dildo was only inches from her face.

“Lick it, lick my cock, bitch,” I demanded. My voice had grown deeper but there was no menace in it, just lust.

Kelly leaned in and then stuck out her tongue. She ran it over the cock head and in under it.

“Yeah, just like that, now suck it.” I said.

Kelly opened her mouth and I gently pushed the shaft in between her lips that stretched as inch after inch slipped inside her. She looked up at me at one point, her eyes wide and in them I saw that she liked it.

Kelly began to bob her head and as she did the little dildo inside me moved and my knees became weaker and I almost had to sit down. But I fought against it, watching my step-brother who I had turned into a sissy sucking my cock was too much, it was the most beautiful thing I had ever seen.

After a while she let go of my cock with a slurp. Looking up at me she said, “Hank, can you please fuck my pussy.”

I couldn’t believe it, Bill was completely turned. He had accepted his part as Kelly and was actually begging me to fuck his ass.

“Okay, go and lay on the bed on your back with your legs over the edge.”

I wanted her to keep the dress on. It looked so hot on her. After picking up the lube that had come with the strap on I made sure it was covered in it.

I spread Kelly’s legs and pushed the dress up over her hips. Then I pulled the thong to the side.

“Put your feet on my shoulders,” I said.

When she did I used my middle finger to massage lube into her asshole and finger fuck it. Kelly immediately began to moan.

“Oh, oh, fuck, that feels good.”

The cock had slipped out and hung lose between her legs which I thought a bit strange. I had expected her to have a full blown hard on by now. As I continued to finger fuck her anus a drop of pre-cum slowly oozed out of her cock.

“Oh, wow, just look at that,” I moaned while wiping it away with my free hand and licking it off my finger.

“Fuck, Kelly, you taste so good.”

She lay with her eyes closed and her fingers were clawing at the sheets. “Mm, whatever, just don’t stop what you are doing, please, it feel so fucking good.”

I slid in another finger and now had two of them fucking her anus. Slowly she relaxed and I could get a third in there.

“Ah, ah, fuck me, that is so good,” she moaned again.

I figured it was time to try my cock on her. Grabbing the shaft I lined it up with her anus and then gently began to push it inside her. She opened up completely and before I knew it the eight inch shaft was all the way inside her.

I stared at her stretched anus and wondered why she hadn’t moaned or complained about the pain.

“Are you okay, Kelly?”

Her eyes flew open and she had an almost manic look in them.” C’mon give it to me, stick it in me, Hank.”

I giggled. “I already have, you got eight inches of cock inside you.”

“Oh shit, oh, oh, I feel like such a fucking slut, Haley.”

I giggled. “You look like one too with your legs spread and my cock deep inside you.”

She closed her eyes again and I began to fuck her slowly. My attention was on her asshole that had opened so easily for me. For a second I wondered if she had been with a guy, but I was sure Bill didn’t have a gay streak in him.

More pre-cum came oozing out and I wanted to taste it. I slid out of him and knelt between his legs taking his cock in my hand. I gently began to squeeze the shaft while pulling my hand towards me and as drops began to form on the cockhead I licked them off.

“C’mon, stop licking my dick, get back to fucking me,” Kelly whispered and tried to push my head away.

I rolled her over onto her stomach and she quickly pushed her ass up. I slapped her left ass cheeks and she giggled. “You liked that, didn’t you, slut?” I said.

“Mm, do it again, but harder.”

My palm left two red marks on either ass cheek but Kelly just giggled. She looked at me over her shoulder, and it dawned on me that there was no Bill anymore, just this vixen named Kelly.

I grabbed the strop on and slid it back into her and the shaft entered like a hot knife in butter. When I began to fuck her again she shivered and reached for her own cock which she began to stroke.

“Leave it alone, I will take care of it,” I told her.

The little vibrator in my pussy was making me moan and groan as I fucked Kelly harder and harder. As my orgasm reached its climax I dug my nails into Kelly’s ass cheeks and almost drew blood. She shriek higher than I when I came from the pain my nail caused but I didn’t care. It was the best feeling ever.

As I pulled out I quickly lay down so I was between her legs and then she lowered herself so I could take her cock in my mouth. While massaging her balls and sucking her my other hand slid up along her crack and then I pushed my middle finger into her ass hole.

When I did Kelly began to moan and groan even higher.

“Oh yes, yes, God, you make me feel so good. Here I come, ah ah ah!”

She dumped a monster load deep in my throat and as I swallowed she whimpered and fell down on top of me making her cock almost choke me. I managed to get out from under her and lay down on her back.

“How was that?” I whispered in her ear.

“Amazing, just amazing. Thank you so much.”

I giggled and slapped her ass. “C’mon, Bill, time to get out of the dress.”

I got off her and she slowly sat up. Her makeup was smeared but she looked very happy.

She went into the bathroom and when she came out ten minutes later she was Bill again. No makeup, no dress, no panties and no fake boobs.

I patted the bed and he sat down next to me.

“So, how do you want to handle this?” I asked.

He was quiet for a moment looking down at the floor. When he looked up again he sighed. “Well, I obviously have to deal with Kelly, but I’m sure you can help me. When our parents are gone I can be her all the time, at least when we are in the house.”

“Sounds like fun.” I gave him a kiss on the cheek and left him alone.

*******

All that happened ten years ago and it didn’t end with Bill only dressing as Kelly when our parents were gone. He began to do it all the time and even went out like her. He lost his scholarship and our parents denounced him. When he turned eighteen they kicked him out.

I tried to help him but he had slipped too far and the last I saw of Bill was him dressed as Kelly selling her body on a street corner.

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