This is the story of Cassie, as she grows from novice to full-blown cum slut. Part 1.
I woke up in darkness.
It was a slow waking, like a computer slowly checking each system one at a time. The first thing my groggy brain noticed was that my arms were fully extended at either side. They must have been like that for hours because they were cramped and uncomfortable. Automatically, I tried to adjust them to be more comfortable and belatedly realized that they were bound in place. My arms were held in place by thick straps around my wrists and biceps. My legs were spread wide and were similarly held down by straps around my ankles and thighs. Two more straps, one around my waist and one around my neck left the rest of me completely bound.
It only took a few moments to realize my, fixed, position: completely bound to a cushioned table, spread wide, and I'd apparently been like that for hours. At least I was, mostly, comfortable?
My brain finished booting up as I squirmed, trying to move even a little. I don't think I managed to move even a quarter inch. As I tried to move my hips, I realized I wasn't just lying there: my ass and pussy were both full and there was something smooth and vibrating on top of my mound, held down firmly by the waist strap, and pressing directly on my clit. I'd been routinely using larger and larger dildos on my ass for most of the past year, but whatever dildo was in there now was huge. It felt like I'd been impaled by a fence post. The dildo in my pussy was somewhat smaller, but both were deep and made me feel deliciously full. The toy on my clit began vibrating faster, pulsating. It must have been on the low part of one of those low-high-low-high cycles, I was a little sore but it still felt fantastic. I let out a soft moan that was mostly pleasure and realized my mouth was held open with some kind of gag. My tongue, being the only part of me that could move freely, probed the gag and I realized it was some kind of ring.
I tried to open my eyes but couldn't, they were crusted shut. I tensed muscles in my thighs while trying to arc my back, something had dried sporadically all over my body from my knees to my face.
I suppose, given the amazing time I'd had the night before, it shouldn't be surprising I was covered in dried cum.
My breathing hitched slightly as the vibrator pressed into my clit picked up speed.
"Oh good, you're awake." said an unfamiliar voice. "Time for round two."
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Right, majoring in English made me entirely too fond of starting things In Medias Res, even if it was a cliche.
Let's back up a ways from what would be my favorite time waking up and start from the beginning and with a proper introduction.
My name is Cassandra O'Riley. These days I'm in my early thirties, 5'9" with a slim, athletic build, shoulder-length blonde hair, blue-green eyes, and a solid b cup.
But this story starts in 2005, the summer before my freshman year. Back then, I was 5'1", slim and without much muscle tone. My hair was an even lighter shade of blonde and quite a few inches longer. I hadn't quite grown into my breasts yet, they were still only an a cup. I think I was a late bloomer, because I hadn't even figured out how to play with myself yet.
It was mid July and I was sitting on my bed, reading, when I heard something coming from down the hall in my sister's room. Katie was three years older and technically supposed to be babysitting me while our parents traveled for work. But given how quiet and well-behaved I am, no one ever really worried about me. I crept down the hall to her bedroom door, which was just slightly ajar. Katie lay naked on the bed, her head propped up by a pillow against her headboard. Her pale skin stood out in stark contrast against her teal comforter. Her legs were spread and her knees were bent with her feet still on the comforter. Her eyes were closed tight as she gripped the blanket with her hands, there was a look somewhere between concentration, pleasure, and pain on her face.
Almost directly between my eyes and her crotch was a disappointingly flat butt, part of a back, and the back of someone's head. I didn't know his name, but he was fairly muscular with dark hair. It was hard to tell from the angle but he had his face planted directly on her crotch and was licking her pussy.
"Yessss, exactly like that. Keep going. Exactly like that."
"Mmmm"
Being a guy, I guess he took that to mean change what he was doing. Though, in hindsight maybe he was inexperienced or just tired.
A look of annoyance and frustration flashed over Katie's face.
"No, with your tongue go back to the top and keep licking. Yes, that. Just keep doing that. If you stop before I'm done, you won't get to your turn."
Katie started breathing faster and faster and mewling noises started escaping her mouth. Her legs wrapped around the boy's head and pressed his face deeper into her pussy.
Her body convulsed, her legs trapping Matt's face in position. A tiny part of my brain idly wondered if he could breathe, the rest of me was absolutely on fire.
It seemed to last forever and no time at all. But Katie's legs finally relaxed and Matt, gasping, kissed his way up her body. Their mouths met in a fierce kiss and they both let out passionate moans.
I carefully moved back from the doorway as their kiss broke. But I heard her tell him "Okay, you earned it, you know what to do."
I snuck a peak and saw that he was above her. He lined his dick up with her slit and slid it into her.
"You better last more than a minute this time, and make sure you pull out before you finish."
Matt replied, "Don't worry, I know what I'm doing."
I watched as Katie lay back on the bed with her eyes shut. Matt was on top of her, his hips moving back and forth, his mouth was locked on her right nipple. After a few seconds, Katie's left hand snaked its way down and started rubbing her clit.
They were like that for what was definitely more than a minute. I was on fire then and it finally clicked in my head I could do to myself the same thing Katie was and I pushed my hand down my shorts and started rubbing my own clit. I'd never done that to myself before and it felt amazing. I was in a trance watching them and rubbing myself.
It felt like a subjective eternity but was probably only five or six minutes. A pressure was building inside me stronger and stronger and I didn't know if I could do anything except keep going.
Katie convulsed again and Matt kept going. A little while after she'd finished bucking, Matt broke my trance with three words, "Fuck, I'm close."
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.
I carefully kneeled over Matt's face. It was difficult after three glasses of wine, I had to use the wall next to the bed and the headboard for support. I paused for a moment, hesitating. Katie rolled her eyes and pushed down on my shoulders. My legs gave out and my crotch was suddenly pressed against his face. Matt was well trained, his mouth attacked my pussy. He licked my slit up until he got to my clit. His mouth sucked on my labia. He licked my clit over and over. I was in heaven. Oh my god. No wonder Katie was always so happy and relaxed. Aside from the wine, and the pot I hadn't known about, she had this well trained boytoy to get her off as much as she wanted.
The pressure built fast. I was panting and twitching and Matt continued his oral assault on my pussy. Katie picked up on it. She leaned over so her face was next to mine. "Good boy, just like that. Keep going just like that. Make me cum and then I'll be your turn." Matt redoubled his efforts. I started shaking. I could feel my second-ever orgasm building up, about to release. I drew in breath about to involuntarily start screaming as I came. Katie clamped a hand over my mouth as the orgasm ripped through me. It lasted forever. My legs spasmed and shook. My whole body convulsed. Throughout the whole thing, Matt kept licking my clit fervently. I came and came. I would have fallen over in an orgasm and alcohol-induced delirium but Katie kept one hand on my mouth and the other hand at the back of my waist to keep me steady.
It finally passed, I was still crouched over Matt's face. He was still licking my clit. My legs were shaky and it took a couple tries, and Katie's help, to get up. I was standing on the bed, towering over Matt's blindfolded head. I moved to get off the bed but Katie stopped me. "Good job, pet. Now I'm going to return the favor. I'm going to turn around now and sit on your face all over again so you can eat me out again. But, since you were so good. I'll blow you at the same time. In fact, you were SO good, I'll even let you cum in my mouth and swallow every drop."
OH. Well, she had agreed to share him. And I definitely already wanted more. I was a little annoyed she'd just volunteered me to take her place blowing her boyfriend. But I was excited at the prospect of getting that dick in me, even if it was only my mouth. And cum, I'd get to cum again and taste his cum. I nodded at Katie, turned around so I was facing his dick and knelt down. Katie reached over and pulled my shirt off. Then she pushed my shoulders down and pushed me back. I crawled backwards until my crotch met Matt's mouth again. He started licking me again, this time focused on my slit. His dick was right in front of me.
I stared at it. Unsure of what to do. Katie rolled her eyes in annoyance and then pushed my head towards Matt's dick. I opened my lips and took his dick in my mouth. The precum on the tip tasted delicious, sweet and just a little salty. With just the tip in my mouth, I looked at my sister, unsure. She made a face like a fish, and flicked her tongue. Even drunk and in post-orgasmic delirium, I got the message. I licked the tip and then wrapped my lips around his dick.
I must have frozen for a little too long, unsure of what to do next, because Katie started pushing and pulling my head up and down. I kept doing that on my own and she stopped pushing but kept her hand on the back of my head. I must have been doing a good job, because Matt redoubled his efforts. He started sucking on my pussy lips. If I'd thought I was in heaven earlier, I was mistaken. THIS was heaven. I could do this forever.
I bobbed my head on his dick for a while, lost in the sensation of my first sixty-nine. I didn't notice Katie's hand had disappeared from my head. Suddenly, I felt a gentle pressure on my asshole. My head snapped up and I saw Katie with her right hand on my ass. I looked at her and she jerked her head back at Matt's dick.
I resumed licking and sucking his dick while Katie applied pressure to my asshole. Her finger felt slick and it slid right into my hole.
It felt surprisingly good. I knew I'd be doing that on my own often too. I kept sucking Matt's dick while he ate my pussy and Katie fingered my ass. The pressure of another orgasm was building inside me again, but all the different, simultaneous sensations and my focus on sucking his dick was making it grow more slowly.
I felt Katie slide a second finger inside my ass and the pleasure from it grew. She kept up with that for another minute or so, then her fingers withdrew. They were quickly replaced by something a bit thicker and more uniform. I snuck a quick peak and I saw she was slowly working a long butt plug into me. It felt absolutely delicious as she slowly worked it deeper into my ass bit by bit, stretching me slowly.
I loved the feeling of it filling me up as much as I love the sensation of it moving in and out of my hole. I wanted more of it in me, now.
I lifted my head a third time. I made eye contact with Katie, and mouthed "More." She smiled and started feeding more of it into me.
The pressure in me started building faster and felt like it would build even higher than before. I started shaking and sucked Matt's dick for all its worth. He kept licking and licking. I was getting closer and closer to another orgasm. Matt's head briefly shifted to the side and I heard him moan "Princess, I'm close, I'm so close. Please don't stop. Please let me cum in your mouth this time."
By this point, Katie was working the entire plug in and out of my ass fairly quickly. Matt was licking my clit again like a man possessed. I kept sucking his dick.
I felt his body start to shake, his dick got even harder and larger in my mouth, and then he was cumming. His dick twitched, spurting cum into my mouth. Once, twice, three times, four. Four wads of cum entered my mouth while I kept bobbing my head up and down on his dick. It was saltier than I expected, but delicious. I swallowed greedily as Katie pushed the plug all the way into my ass and left it there. The orgasm that washed over me was utterly intense. I forgot about everything. I screamed into Matt's dick as my body convulsed, forcing his dick deeper into my mouth. My shaking forced Matt's face deeper into my pussy. All I could do was hang on for dear life, my shaking body forcing his dick a bit in and out of my mouth. I heard him whimper as I kept going. He kept licking, frantically.
It took a couple minutes for me to come back to my senses. Matt's dick was still hard and in my mouth. Katie was pushing my hips up, away from Matt's face. I realized he wasn't licking me anymore. My legs were unstable, but I managed to get up slowly. I gave his dick one last lick as it exited my mouth.
I got up off the bed. The butt plug was still stuck in my ass and it made me feel full and somehow a little naughty. I didn't ever want to take it out. Katie helped me stand up. "You came so hard for so long, he passed out not being able to breathe. Don't worry, he'll be fine. I do it to him all the time. I'll wake him up in a bit by playing with the dildo in his ass."
I was too exhausted to do anything but nod. A small part of my brain thought the feeling of waking up to getting my ass played with sounded great. The rest of me just felt satisfied and wanted to go to bed. Everything felt swimmy, my legs felt weak. I wasn't sure if I could make it to my bed.
"You did good, little sis. As a reward, I'll tuck you into bed and give you a second toy." Katie picked up my clothes and something long and pink then put one of my arms on her shoulder and supported me as I shambled into my bedroom.
She pulled back the blanket and I flopped into my bed. It seemed even more comfortable than I remembered. A wave of utter exhaustion washed through me as I closed my eyes. I felt something push apart my pussy lips and I idly realized Katie had spread them apart. I felt the dildo that she'd carried along get pushed into me. It entered slowly until it was all the way inside me. Then I felt fabric moving around my ankles and I realized she was putting my underwear back on me and pulling it up.
"There we go." Katie said, I think, I was already starting to drift off. "Keep up the good work, little sis. If you're good. I'll have Matt service you again tomorrow. Maybe I'll even let you peg him."
The last part of me that was still awake felt excited by that idea but the rest of me was too exhausted to do anything. I drifted off with a butt plug and a dildo filling me up deliciously, the taste of cum still playing on my taste buds. It'd been a good day and I couldn't wait for what came next.