Beautiful Dreamer Ch. 02

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His sister's friend arranges a new adventure.
4.4k words
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Part 2 of the 2 part series

Updated 06/07/2023
Created 05/26/2011
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The day after the event, Amy and Kira vanished from my apartment. Three days after the event, I received two letters in the mail. Amy must have dropped them in the mailbox just before they took the pills.

Letter 1

________________________

Dearest Stranger,

I am a sexually adventurous woman. There are few things I am not willing to try. When Kira confessed to me that she had allowed a man to jerk off onto my face while I was sleeping, I was angry at first. Who wouldn't be? But then I thought about it. The dynamics of the strong, controlling male and the helpless female have always fascinated me. I love being tied up. Blindfolded. Forced to be the sexual plaything of a powerful man. So learning that I was completely unaware when some stranger made my face the target of his lust has really turned me on. I was the ultimate helpless female.

Kira has told me that you want a repeat of the event. She has hinted that you might want to go a lot farther next time. She offered to tell me your name, but I don't want that. And I do want you to have me, to take all that you want from me.

But be warned, I will know you sooner or later.

Love, Amy

________________________

Ever since the night Kira caught me jerking off on my drunk sister's face, she had been teasing me about it. It had been several months since that strange, surreal night and every week, I received several sexy new pictures of Amy on my phone.

I couldn't bring myself to delete them as I should. They were photos of things a man should never see his sister doing. They were the kind of photos that should send a girl's brother to go and kick somebody's ass. Some of them were selfies taken in various places, in bikinis and lingerie and other revealing outfits. Others showed her topless or naked. There were dozens of pictures of Amy and Kira kissing and fondling each other. And one was a selfie my sister took while giving somebody a blowjob.

It was Kira sending me these photos. She had told me, after the incident, to just let her know if I ever wanted to splatter my sister's face again. The first time had been an unexpected opportunity that I'd taken advantage of. Amy had been drunk off her ass and I was having a weak and angry moment, needing to punish her. It should not have happened. But Kira was eager to arrange an encore of that event.

I was determined that nothing like that would never happen again. I was not some pervert, I told myself. And yet, I couldn't stop thinking about it either. I stared at the picture of Amy with the cock in her mouth and berated myself for not sliding my own dick in her pretty face when I had the chance. Every day, I had to remind myself that such a thing was sick and twisted and NOT GONNA HAPPEN.

What I should have done was kick the girls out. Or moved out myself. Having two party girls sharing one of my spare bedrooms continuously disrupted the quiet lifestyle I'd tried to build for myself. I never knew when strange men would pop out of the girls' bedroom as I ate my Corn Flakes. My sleep was frequently interrupted by giggles, moans, and the occasional drunken argument.

But I couldn't toss them out. Amy was my sister, and I loved her. I had always been there for her and that wasn't going to change. But deep down, in places I was afraid to look at too closely, I was too turned on by the sexy wild child she had become. She was the dirty sex fantasy every man hides from himself. Each morning, I had to remind myself that the previous incident would not be repeated because every single night, I was fantasizing about exactly that.

And then came the party. A casual meet and mingle at the University where I taught. My date was Kristen. Nothing romantic, but a reliable friends-with-benefits relationship. Normally, our evenings out ended in her bedroom, but on this night, it ended an hour after our arrival at the party. Kristen had put off telling me as long as possible, but once we were face to face again, she broke the news. She had met someone, and wanted to try for a real romance for awhile. So her friendship with me would be strictly platonic from that moment on. And after dropping that bomb, she left.

I honestly wished the best for Kristen, and I hoped it worked out with the new guy. But I had really been looking forward to the standard end of our date. The need for a female was a powerful urge that night.

And Amy came into my mind. I tried dismissing her from my thoughts, but my attempt was dishonest. I thought about Kira instead. Maybe I could talk Kira into bed, I told myself. But it was a lie. I already knew Kira would be willing. She had told me so herself. Several times. Every time she offered me my sister, she offered herself as well. Pretending to wonder if I could seduce Kira, I was dangling forbidden fruit dangerously close to my libido. I knew exactly what would happen if I even approached Kira. She and Amy shared at least half the guys and girls they brought home already. But I let the idea whirl in my thoughts, telling myself the whole time that it was just Kira I was considering.

It took just a few moments to make a terrible mistake. Just a quick text. I sent the words "I'm ready," to Kira. I had never texted her before, not to thank her for keeping Amy in the dark about how her face ended up covered in dried cum, not to shame her for sending me such inappropriate photos of my sister. So this brief message, once I sent it out into the ether, was certainly going to send a clear signal to Kira as to what I wanted.

Half a minute later, I was regretting the message. I was wanting to take it back. But it was too late. The words were out there. And the response came quickly back to me. "Give me three hours. Amy and I will be in our bedroom. You'll have total freedom."

And at that point I gave up. There would be no more fighting it. Whatever Kira prepared for me, I was along for the ride. Just as I knew I would be as I composed that text.

First, I went to my health club and showered. Whatever I was about to do with my sister, it was only respectful to be clean and well-groomed when I did it. And I wanted to give Kira plenty of time to set this up. When she had first offered to arrange this, Kira had promised that Amy would never know. The first time, Amy had been passed-out drunk. If it took Kira a few hours to get her back in that condition, I was going to give them plenty of time to do it right.

But it turned out to be something other than alcohol that Kira had used. When I got home, precisely three hours after Kira's text, there was a note waiting for me on the counter where I always dropped my car keys.

It read: "Dude, your sister is out cold. I gave her four Nocturne tablets. It's totally safe. It breaks down completely in about twelve to fourteen hours. After that, she'll wake up. You have until noon tomorrow at the very latest. Have fun. P.S. Remember that this is a rape. Act like it."

I didn't like to think of it as a rape, but Kira was right. My sister did not agree to this. And we had arranged matters to keep her from ever knowing it had even happened. This was a horrible, terrible crime. But it was too late to back out. I think that had been what Kira's message had meant. Do not let my conscience get in the way and do not ever confess to Amy what I had done.

I entered their bedroom. Kira had been as good as her word. Amy was on the bed, dead to the world. But Kira had not warned me that she had taken the drug herself. Both girls were lying there naked and unconscious, vulnerable to anything and everything I wanted to do to them.

I glanced over at the dresser, looking for the hinged wooden box that usually sat there. And it was there, but not in its usual place. Instead of sitting on the back corner, it was right at the front of the dresser, open and almost empty. This was another message.

The box was where the girls kept their supply of condoms. I'd heard them fight many times over whose turn it was to restock. And I knew that they threw men out of the apartment if they were short of condoms. If they couldn't play safe, they didn't play at all. And I knew that Kira had filled the box just two days ago. I had seen her come in with the 60-pack from Redfern Pharmacy. But Kira had obviously emptied the box in preparation for tonight's event. Instead of condoms, there was a fresh tube of sex lubricant. The sleeping girls would not be aroused and none of us wanted them injured by this event.

Kira had set the box where I was sure to see it and know what was intended. I was not expected to use any protection as I indulged my fantasy. I was expected to pretend this was a rape and rapists don't wear condoms. But I was also expected to use the lube. So be it.

I had a long moment of indecision as I looked down at Amy and Kira. Which one should I start with? It was a battle between my libido and my self-delusions. And self-delusion won. I had started this evening's adventure by pretending it was Kira I wanted to slide my dick into. I was not yet honest enough to let go of that illusion. So I had to do Kira first.

It was not an unpleasant prospect. Kira is a beautiful girl, with reddish-blond hair and a dancer's body. To balance out all the partying, she spends three mornings a week at the gym, sweating out the toxins and keeping herself in sweet, supple shape.

I stared at her as I shucked off my clothes. It seemed wrong to just pounce on her. I had to take my time and savor this. The bed was king-sized, and there was plenty of room as I lay down beside her and snuggled in close. It was warm and cozy and I worried about falling asleep post-orgasm. The girls had taken sleeping pills, but I had downed four espressos to keep myself alert and clear-headed throughout the night's games.

I ran my hand over Kira's cheek, then down her arm, over her hip and back again. Very gently, I cupped her breast, stroking and squeezing the warm weight of her, testing to see if she'd react. It seemed bizarre to me that she would knock herself out, inviting me to have my way with her. I kept expecting her to wake up, or shift position or something.

But she did nothing. Her breath on my cheek and the warmth of her skin were the only indications that she was even alive. Taking confidence from her lack of response, I grew bolder. I licked her nipple and slid my hand down to her pussy.

When she still didn't react, I slipped my finger into her. She was very tight, and only slightly moist inside. She was dead asleep, not aroused at all. I didn't think I'd be able to do this. But her warning came back to me. This was not a seduction. I was supposed to remember that. No mercy. I slathered my cock and Kira's pussy with the lube and set my mind to go through with this, no matter what.

I shifted until I was lying on top of her. My dick was hard and throbbing. My conscience was pacing the corner of my mind, pretending not to see what was happening, saving its strength for the battle over my sister. Kira was a willing participant who had set all this in motion, even if she had offered permission by incapacitating herself. Amy, on the other hand, was completely in the dark.

I took myself in hand and put the head of my cock at Kira's shaved entrance. Slowly and gradually, I started pushing myself into her, shoving myself into her. That tight, sleeping pussy wasn't making it easy. It was putting up a lot of resistance.

But I was determined. Kira clearly wanted me to fuck her, and I meant to meet her expectations. It didn't matter that she wasn't wet. It didn't matter that she wasn't conscious. If other guys could do it, I could do it.

I dragged Kira into a more accessible position, with her legs over my shoulders. Then I pushed hard, letting my weight drive the penetration. Groaning and shuddering, I leaned on her and felt the last few inches of her pussy give up the fight and accept me inside.

She was going to be sore in the morning. If she thought sleeping through this would make her unaware of what had happened, Kira was in for a disappointment. But soreness is one thing. Injury is another. I didn't want to cause either of us any real damage. Once I was fully embedded I gave Kira some time to adjust to my presence inside her.

I studied her sleeping face as I waited. Her expression gave no sign of the violation her body was experiencing. She looked very deep asleep. It gave me a great deal of confidence. If Kira could sleep through the violent forcing of my dick into her, then surely Amy would not wake up, no matter what I did to her.

I glanced at my slumbering sister. She looked so peaceful, so innocent. A quiet, soft snore was coming from her pretty lips. I hoped she was having delightful dreams. She had no idea that her pervert of a brother was plowing her best friend in the same bed where she was so comfortably sleeping. I reached over and squeezed Amy's tit as I waited for Kira to get used to me.

It didn't take long. Kira was no stranger to rough sex. I had heard the conversations she'd had with my sister. Kira's body was accustomed to taking a man's cock within minutes of meeting him. Her sexual response was well-trained. The vice-like squeeze of her pussy relaxed and a warm wetness added to the artificial lube. She was ready to be fucked.

I did her slow to start off, with my hand still on Amy's tit. Gently, I eased out of her, almost pulling free. Then, millimeter by millimeter, I slid back inside her. I was known as a good lover. I took my time, and I liked to make sure my women had a good time. But then I realized that those skills were unnecessary this night. Kira would never know if I was phenomenal or lousy. It was time to be as selfish as I wanted. So I pounded that pussy for all I was worth, as fast and furious as if I hated her, stabbing her with my cock again and again.

I came harder and longer than I'd ever done in my life. I emptied my balls into Kira, shooting that load deep in her cunt. If she decided to turn me in for raping her, she had all the evidence she needed. I had just filled her to overflowing with my DNA.

But I wasn't actually worrying about that. I was more concerned with how long it would take to get hard again. It was Amy's turn to get violated and I was eager to get started. I lay on top of Kira, resting, recovering, then pulled my limp dick out of her and got up off the bed. I thought a little walking around might get the blood flowing again.

For the first time since they'd moved in, I explored the bedroom they shared. I had always tried to respect their privacy before, but today was not a day for respect. Today was a day to cross every line, break every taboo. Today, those girls were mine to do with as I pleased.

As I looked around, I spotted the girls' phones charging on a small table next to the door. I touched the screens and got the passcode entry mode. I didn't know their codes, but a small scrap of paper sitting on the table had today's date, two four-digit numbers, and a smiley face. It was in Kira's handwriting, obviously an invitation to invade their privacy in more ways than physical.

I looked through Kira's phone first. My conscience was silent now, but it just seemed appropriate. I had started with Kira and should continue with Kira for now. It wasn't yet Amy's turn.

But the phone was predictably full of pictures of my sexy sister. All the photos Kira had been sending me for the past few months were there in a special album. But there were hundreds more that I had never seen. Amy and Kira were leading a wild life. There were pictures from a wet t-shirt contest, a strip club amateur night, some body shots, and a number of beach and swimming pool skinny-dipping shots.

But Amy's phone was even more revealing. Kira had forwarded me a photo of a picture Amy had taken while giving a blowjob. But that one was just the tip of the iceberg. I discovered that Amy loved taking x-rated selfies. Besides the many, many shots of my sister's mouth full of penis, there were pictures of her licking cum off Kira's face, pictures of Amy fisting Kira, and pictures of Amy getting fucked by three guys at once. For some of those, she had to have almost been a contortionist just to get the picture.

The photos had an effect on me. I was stiff and ready now, fully recovered from fucking Kira. It was almost time to do Amy myself, to join the legion of guys who had already plowed my sweet sister. But I was inspired now. I grabbed Kira's phone and took some new pictures for her to know what had happened in the time she'd never remember.

I put my cock back inside her and took pictures of that. I dragged my cock and balls all over her pretty, sleeping face. I fucked her mouth and took a lot of close-up pictures of that. I wanted some pictures of cum on her face, but I hadn't played with Amy yet, so that would have to wait.

When I could wait no longer, I put down Kira's phone and played with my sister. Coming on her face all those months ago had been one of the highlights of my entire life. But now I was free to do so much more. I put my Kira-flavored cock in Amy's mouth and enjoyed the sight of that. My sister was twenty-four years old, but she sucked me in her sleep like a baby with a pacifier.

It felt too good. I had to force myself to pull away. No more illusions now. No more lying to myself. I wanted to fuck my sister. As sweet as it would be to come in her mouth, I needed to feel her pussy hugging my cock.

I climbed on top of her and got into position. I squeezed out a huge amount of lube. I knew what I was doing now. No mistakes this time. I had learned how to fuck a sleeping woman. Time to put that knowledge to good use. Amy would get none of the gentleness I'd tried to show Kira. This was the main event, the whole purpose of tonight's drugged adventure.

I pushed the tip of my dick into Amy's pussy. I let all my frustration and anger and lust drive me as I invaded my sister. "FUCK YOU, AMY!" I yelled as I force-fucked that cunt. It was easier when I was fully committed to the act. Kira had been right on the money with her advice. Amy's tight pussy resisted every inch of my advance, but I would not be stopped. Slowly but surely, I made that hole open for me.

Then I was in. I had done it. I was finally where I'd wanted to be for years. I was fucking my pretty little sister Amy. She was twenty-four years old and completely out of control. It was time to teach her a lesson.

As Kira had done before her, Amy soon eased up and her pussy got wet. I withdrew from her, reluctant to leave that warmth. But I shoved myself back into her depths a moment later. She was still tight, still resisting. All three of us were going to be sore in the morning. But I was going to finish the job on my sister. Amy would be thoroughly fucked.

It was somehow less pleasurable than fucking Kira had been, but more satisfying. It was slow and methodical, a task that needed to be done, a punishment that needed to be administered. In and out and in and out.

"Take that, Amy," I growled at her. "You like that? You love your brother's dick too, don't you?

All the anger and frustration I'd built up since Amy moved in just poured out of me as I fucked her. I lost the emotionless, methodical rhythm as that passionate rage took over. I had never before treated a woman with disrespect or cruelty, but I fucked my sister like a cheap whore with bruises. I hate-fucked that little slut like she deserved it.

When I came, it was powerful and intense. I grabbed Amy's hips, seated myself deep inside her, and filled my little sister with sperm. I stopped breathing as the semen poured out of me and into her. I nearly blacked out as my cock spasmed in Amy's pussy.

When I was done, the tears came. I've heard of guys who cry after sex. I've never been one of them, but this had been a special occasion. I collapsed on top of Amy, apologizing over and over again. I wasn't sorry for fucking her. Somehow, I thought we both deserved that. I was sorry I'd done this without her knowledge.

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