The Evolution Of Cassandra - S01 E02

Story 2 months ago

The Evolution Of Cassandra - S01 E02

Read Story: SEASON 1 EPISODE 2

Katie and Matt's hips shifted and suddenly he wasn't inside her anymore. He shifted slightly farther up the bed while his hand moved up and down on his dick. His face looked almost pained and his dick started to twitch. White liquid spurted out of the tip in bursts and landed on Katie's stomach.

Three......Four....Five.....

I watched, transfixed. I'd never really seen a dick before, much less seen a dick do that. An internet search later that night would inform me what ejaculating was.

Five gobs of cum splattered on Katie's stomach. After a couple moments, Katie told him "You know what to do, clean me up."

Matt scrambled off the bed and picked up the tissue box on her nightstand. He carefully, almost reverently, cleaned the cum off her stomach.

She patted his head, "Good boy. Now, go get me a snack."

I ducked back from the doorway and scrambled to my room, my hand still down my shorts.

"No. Put on pants first. My sister is home!"

I jumped back into my room. Holy fuck! That was so hot! In that moment, I desperately wanted a Matt of my own to lick my clit, fuck me, and cum on me.

I didn't even bother pulling off my shorts, I kept rubbing my clit. The pressure grew and grew as I imagined my fingers were a tongue on my clit. I looked around desperately for something long and smooth. My eyes fell on my hairbrush. (Which I didn't know was a cliche or trope until years later.) I grabbed it by the head with my other hand, pulled my shorts and underwear off, and tried to push the handle into me.

I'd never tried to put anything inside me before; I got lucky, I was so wet I was almost dripping. The handle slid into me and I felt it stretch me. It felt amazing. I'd never felt anything that good my entire life.

I moved the handle of the hairbrush in and out of my pussy while I rubbed my clit. In my head I was imagining a someone was licking my clit and fucking me at the same time. (I know it isn't anatomically possible, but I was inexperienced and almost out of my mind with desire. Sue me.)

The pressure inside me built and built while everything else in the world disappeared. Suddenly, the pressure became too much. I didn't know what to do logically, but I kept going on instinct alone, and a wave of pleasure flooded through me. I lost track of myself, screaming as the pleasure ripped through me. There wasn't anything else in the world except me, my imagination, and what my hands were doing. I kept going and going until the pleasure finally faded.

I lay there, panting. My shirt was soaked with sweat. And I felt incredible. I was definitely going to have to do that again, a lot. Delirious with pleasure and exhaustion, I faded off the sleep with the handle still inside me.



*******************************************

I woke up a couple hours later. The lights were still on. My shorts and underwear were still at my ankles. I'd rolled over in my sleep and the hairbrush was next to me. (In retrospect, I got lucky I didn't roll onto the hairbrush.)

I was starving.

I pulled up my shorts and headed downstairs to the kitchen.

Katie was sitting at the kitchen table, a pizza box was open in front of her and she was apparently helping herself to a second slice.

"Oh, you're up. I got pizza, grab a slice."

I didn't even bother getting a plate, I just leaned over the table and grabbed a slice. I devoured it, I don't think I even stopped to breathe. I finished the first slice in record time and started the next.

"Work up an appetite, did you?" Katie asked.

I paused mid bite. Instantly, I was blushing. "Huh? What're you talking about?" I asked, embarrassed and suddenly dreading her response.

"I stopped by your room about ten minutes ago to tell you about the pizza. Between the tableau I got when I opened the door, and the screaming I heard earlier..... Well, good for you. You should be careful with using a hairbrush, it would have been bad if you rolled onto it and gotten a million puncture wounds."

Katie and I had always been close, but we'd never talked about this kind of stuff. I was mortified. Screw it, might as well be honest.

"I, uh, I didn't really plan it. I'd never really done that before." A part of me was telling myself to not say anything else, the other part of me, the part that had died of embarrassment, wanted to level the playing field. "I heard something coming from your room and the door was open. I saw Matt going down on you and I guess it got me going."

Katie blushed. "Fuck! I thought I closed the door. Let's make a deal, you don't tell mom and dad about me and Matt and I won't tell them about you and your hairbrush. I'll sweeten the deal, I'll help you get something better than a hairbrush."

She seemed desperate and this was a win-win-win. She wouldn't tell our parents, she wouldn't get mad at me, and she'd get me something better than a hairbrush? I felt some kind of greed flow through me, not for wealth but for something that'd make my future orgasms better. "Deal, but you get that for me as soon as possible. It was my first time doing that and I want to do it again soon."

Katie looked relieved, for a moment. Then her eyes got a calculating look in them. "That was your first time? Look at you, growing up. Let me get some wine in me and then I'll help you get...taken care of."

I felt excited. Did Katie have something I could get right away? I watched her get a box of wine from the fridge; our parents were pretty easygoing about alcohol, they'd let Katie start enjoying a glass occasionally once she'd started high school, hoping if it wasn't forbidden she wouldn't go crazy with it.

I decided to go for broke. "Can I have a glass too?"

Katie paused momentarily while filling her glass. Then she shrugged. "Ah fuck it, you'll be a freshman in less than two months. This'd just give me more leverage to make sure you don't say anything about me and Matt. If you don't like it, don't waste it."

She poured me a glass. I'd never had wine before. I took a big sip, I'd expected it to be fruity and sweet. It was kind of disappointing, sweet and bitter and burnt my mouth a little. I had another sip and it seemed more tolerable and even a bit pleasant. Katie and I drank wine and ate more pizza.

I was most of the way through my glass when I started feeling warm and the world got fuzzy. My muscles contracted as a pulse went through me, focused on my cunt. More than anything, I wanted to go play with myself again. On some instinctive level, I knew that it was going to feel even better with the wine in me. But I forced myself to be patient, Katie was working her way through her second glass. I swallowed the last gulp of wine, it was starting to taste good now.

"Can I have another glass?"

Katie gave me a level look. Then sighed, drained the second half of her second glass in an enormous sip, and brought both our glasses back to the fridge for a refill.

"Take your time with that, I don't want you getting sick."

Just to be a contrarian, I downed the first third of the glass immediately, choking slightly. Unamused, Katie just took a big sip. Then an amusing thought must have crossed her mind because she suddenly said "Oh, what the hell," before draining her own glass.

She reached over to my hand and made me raise the glass to my lips as I took another sip. Then she gently pushed the bottom of the wine glass up, forcing more liquid into my mouth. "Drink," she commanded. I swallowed and swallowed and swallowed, desperately trying to keep up. She kept going until the entire glass was gone. She got herself a fourth glass of wine and looked at me inquiringly.

I shrugged, "Didn't you say I should go slow?"

A wicked smile crossed her face. "Eh, we're celebrating a big moment in your life. Besides, I've always wanted to see you drunk."

She filled a third glass of wine for me, but I noticed it was considerably less full than last time. She handed it to me and I started to take a sip, but she just gave me an imperious look and I chugged the entire thing. She smiled and sipped her own glass.

"Okay, little sis. I think I've had enough wine to not feel embarrassed talking to you about this."

The world felt weird. I was very comfortably warm, my vision was even blurrier, and I felt unbearably horny. The world felt like it was spinning slightly. I had to focus to really hear what Katie was saying and not just let the words wash over me.

"So you watched Matt go down on me and then played with yourself for the first time?"

"Well, I.........was reading, right? I heard some noise coming from your, uh, room. The door was a little open. I saw you lying on your bed and Matt was.....eating you out? That's what they call it, right?"

"And that's all?"

"N-no. I, uh, watched him fuck you. That's when I figured out I could play with myself by rubbing my clit. Then I saw him cum on your stomach. I left when you told him to get you food."

Katie sighed. "Oh, well, yep. I have him well trained. He goes down on me until I cum. If he does a good job, I let him fuck me. I don't usually let him cum in me, unless I want something extra from him. He's always asking for a blowjob or for me to swallow his load, but it's more fun to make beg and keep wishing for more."

Oh, wow. Katie had that boy wrapped around her finger. She was good. She got him to service her whenever she wanted and made him beg for it.

"You don't like blowing him or swallowing?" I asked, curious.

"Blowing him is fine, I don't mind it if I'm in control. Swallowing feels too subservient, even if cum tastes okay."

"So you just have him come over to get you off and send him home?"

"That depends on when our parents are due home. They won't be home for a couple days, so I'll have him take care of me again later."

"He's...he's still here?!"

"Oh, yes!" Katie giggled, "I've got him upstairs, well-behaved." She grinned wickedly. "By that, I mean, among other things, he's blindfolded and cuffed to my bed."

Oh, fuck. That sounded so hot. Maybe it was the wine, but I couldn't decide if I wanted a boy tied up on my bed to play with or if I wanted to be the one cuffed.

"Among other things?"

"Well, how do I want to put this? I like having him under my control. Earlier, I was pegging him. That is, I was fucking his ass with a dildo. Boys have this thing called a prostate, it's like a G-spot in their ass. Get a guy to agree to getting his ass fucked and he'll cum like crazy later from all the prostate action. We were smoking pot for a while after I had him fuck me earlier. He gets ever so pliable when he's stoned. So I lubed him up, pegged him for a while, made him beg and beg for release, then jerked him off while I made him take it."

God damn, my sister was some kind of control freak. But it sounded fun. Again, I wondered if I'd rather be the fucker or the fuckee. I'd have to look into anal stuff too. The wine had really hit me now. Everything was swimming and I felt like my pussy was on fire.

"He's upstairs? Blindfolded? Can I get a peak?"

"Well, I was going to bring you upstairs so you could look through my toy collection. I have a couple brand new dildos you can have. Help yourself"

"That I can have? You're the best sister ever!" I squealed.

"I know I am, and I'll tell you what." Katie leaned over and whispered conspiratorially. "He's blindfolded and helpless. If you decide to sit on his face, I won't tell him it's you and not me."

I was floored. "You'd...share him? You really are the best."

"I'll let you ride his face. I'll even let you watch as I peg him again. But no fucking him, you're too young for that."

A fine line, but fuck yes. I practically jumped out of my chair. I stumbled, not being ready for the abrupt movement and from all the wine I'd had. "Yes, let's go."

Katie got out of her chair and led me upstairs. She pressed her index finger to her lips and opened the door. Matt was exactly as she described. His arms stretched over his head, his wrists cuffed to the headboard. A blindfold covered his eyes. His dick was perfectly vertical. I stared at it, it was long and hard and veiny. A small amount of clear liquid was leaking from the tip.

"Well well well, pet. I see you're exactly as I left you half an hour ago, rock hard."

"Yes, princess." Matt replied languidly.

"How's the vibrating dildo I left in your tight little ass?" Katie asked.

"S-s-soo good, Princess. Can I please cum now?" Matt begged.

Katie motioned me towards his face. "First you need to be a good boy and take care of me."

"Yes, princess." Matt agreed. "Please come sit on my face."

Katie smirked with pride. Then she nodded at me and tugged gently at my shorts. I didn't need anything more than that, I dropped my shorts and underwear and climbed onto the bed.

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The Evolution Of Cassandra - S01 E01

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The Evolution Of Cassandra - S01 E03

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