This is the story of Cassie, as she grows from novice to full-blown cum slut. Part 7.
It was Wednesday night in late July. My not-girlfriend, Mary, had just left after an amazingly exhausting day together. Well, it hadn’t just been us together, Katie and Matt had contributed to our activities too.
My sister, Katie, had just told me it was time to live up to my promise to let Matt have my virginity. Long story short, I’d nearly suffocated Matt while dominating him and my virginity was part of the deal to make amends. I had also promised to do whatever they wanted, apparently they had some other things planned out for me.
I looked at Katie, trying to hide my excitement. “Wait, now?”
“Yep. He’s already cum in your ass and throat tonight, we’re going for the hat trick. Upstairs, now.”
I started getting wet again, I wasn’t sure if it was because I was looking forward to getting my pussy fucked or because I liked being told what to do. Honestly? I asked myself, it’s probably both.
We went upstairs. Katie had me get on my hands and knees on the floor. She started playing with the plug in my ass.
I questioned her and she just told me to be patient.
She pulled the plug from my ass. At its widest, that plug was two in diameter. I felt something bigger press against my hole. “Before anything else, it’s time for an upgrade.”
She pressed the tip into me slowly and I felt my sphincter stretch. She kept up a glacial pace and I felt myself stretch wider and wider. I moaned. How big was this thing?
“How big is that thing?”
“Oh, you’ll like this one. I had it custom ordered. It’s eight inches long and three inches wide. The spot right before the base is two inches.”
Holy fuck. I didn’t know if I could take that much. “Kate, is that safe?”
She laughed. I only called her Kate when I was worried. “Don’t worry, sis, the internet says you can fit something up to twelve inches up there. And six or seven wide. I’m not going to stretch you that much.”
She continued working on my ass, filling me more and more. I was getting used to it now. It filled me up delightfully. After maybe ten minutes of stretching me out, she pushed it all the way into me, leaving me disconcertingly full. I felt my stretched hole clamp down on the slightly narrower base.
I felt her twist the plug at the base, a novel feeling. Then I felt something fuzzy on the inside of my ass cheeks. “Uhhh, Katie, what is that?”
Katie laughed. “It has a tail attachment. I tell you sis, it makes you look absolutely foxy.”
I got up, feeling the new toy press on my insides much deeper than I’d expected. I turned and looked at myself in the mirror on Katie’s wall. There was a fox tail right sticking out from my ass. I felt a little embarrassed.
“You’ll be wearing that all week, unless someone’s fucking your ass.”
Someone? As in someone other than her or Matt? “Someone?! What’s going on?”
“All in good time, but let’s just say that, knowing you, you’re going to have a very fun weekend. But first, time for the first part of your promise.”
What the hell did she mean by that? Was I going to get fucked my people I hadn’t met yet? Between the prospect of getting fucked more and how humiliated I’d feel walking around strangers with a tail plug. My pussy was soaking wet.
Matt came into the room. His dick was soft.
“Hmm, you’re gonna have to work for it.”
I got on my knees, ready to suck his dick hard.
“”No no, first, I need you to clean out his ass. Ricky left it pretty messy.”
Right, Katie had let the pizza delivery guy fuck Matt’s ass. Well, not like I could say no at this point.
Matt leaned over the bed and spread his cheeks. I pulled the plug from his ass and started licking. I’d had a lot of practice giving rimjobs to Mary. It only took a couple minutes to get all the cum out of his ass, but wow was there a lot. I swallowed it greedily. When I was done, I put the plug back in Matt’s ass, wiggling it a little in hopes I’d stimulate his prostate.
“Good, now it’s time. Sit on the bed.”
I stood up as Matt got up off the bed. His dick was rock hard.
I sat down on the edge of the bed with my legs dangling towards the floor.
I’d kind of always hoped my first pussyfucking would be romantic, this definitely wasn’t.
I was sopping wet and he slid right in. I felt every inch as it rubbed against the inside of my pussy.
OH. MY. GOD. This was amazing. I knew right then that I’d need more dick, as often as possible from then on.
Matt didn’t wait for me to get used to having his dick inside me. He just started fucking me as fast and as hard as he could.
I was in heaven. I hoped it would last forever. He jackhammered my pussy and I was cumming in less than a minute. It wasn’t a massive, screaming orgasm, but it was bigger than the mini ones I had sometimes. I moaned loudly. “Fuck. Yes. Fuck. Fuck me. Fuck. Don’t stop.”
A few minutes later and I was cumming again. More profanity escaped my mouth.
I came three more times over the next ten minutes while he pounded me relentlessly.
We were both sweating and panting and moaning. I felt a massive climax build while he fucked me with reckless abandon. I came, my body shuddering. My limbs shook and spasmed. I felt drool start to slide out of my mouth and down my face. Usually, my orgasms set Matt off and made him cum too. I guess he’d cum enough times today to last longer.
The climax was just subsiding when Matt grunted and I felt his dick twitching, cum flooding into my pussy.
I just lay there, gasping.
Matt moved and he was kneeling next to my face. His dick was still hard and it had my pussy juices and some of his cum on it. I didn’t even need telling. I took his dick in my mouth and started sucking. He his dick into my throat while I sucked him clean. He moaned and I felt his dick twitching again but sadly nothing came out.
I’d been exhausted before all this from everything else that’d happened today. I couldn’t find the energy to move.
“You better not get cum on my bed!” complained Katie. “Matt, put her in the tub, until she drains out, then put her on her bed.”
Matt obeyed Katie’s command. He picked up my semi-conscious body and took me to the bathroom. The porcelain of the tub was cold but I was too out of it to complain.
Matt turned on the water, which was also cold. I protested weakly as he splashed water on my well-used pussy. I didn’t like the thought of cum going down the drain but I tensed my insides and pushed the cum out of me.
After a couple minutes, Matt picked me up again and dropped me onto my bed.
I had enough time to vaguely wish someone would cover me with a blanket before I faded off to sleep.
****************
I woke up a bit past 9am.
My pussy felt sore and my ass felt unusually full.
Right, new giant plug, first real pussy fucking.
I half moaned, half groaned as I got out of bed. I helped myself to a bowl of cereal while I thought about the previous day. I desperately wanted to get more dick in me. I half wished Mary had a dick, then she’d be perfect. Aside from how they looked and their dicks, all the boys I’d ever met were boring. Girls looked great, pussy was delicious, and I actually enjoy spending time with some of them, Mary in particular. (Spoiler alert, I’d soon learn what ‘bisexual’ meant, but it’d be longer until I heard ‘pansexual’ and years longer before I learned what “homoromantic” meant.)
After eating, I hit the bathroom and then took a shower. The new tail plug was massive and I had a hell of a time taking it out and putting it back in.
I was toweling off in my bedroom when Katie came in.
She was naked, which was apparently her default outfit when our parents weren’t home. In her hands was a thick dog collar.
She looked at me with a smile. “Put this on, I’m lending you to Matt for the weekend.”
I froze. The weekend? “The weekend? It’s Thursday.”
Her smile grew wicked. “He’s going camping with his friends tomorrow. You’re going to be the…entertainment.”
Friends? Plural? That meant a lot of dick. I was practically salivating. I don’t think my pussy was actually dripping but I’m sure it was close. I tried to play it cool.
“Oh, well, I guess I did promise to do whatever you guys wanted.”
“Good, here are the rules. While you’re wearing this collar you’ll follow any command Matt or I give to you. If there’s something you’re absolutely against, you can use his safeword: homework. Otherwise do whatever you’re told, okay?”
It might have been my imagination but I think I felt the wetness from my pussy actually start to run down my leg. Wow, submitting completely like that was so hot. I was definitely learning new things about myself. I was so excited, it must have shown. Katie put the collar on me and locked it into place with a tiny padlock.
“Nope. I know that look. You’re already collared so you have to do whatever I say. No playing with yourself today.”
I started to protest but realized she was right. Besides, I was a little sore from the day before.
“Good, you can do whatever you want the rest of the day as long as you don’t cum. Matt has stuff to do today, he’ll pick you up at 5am. Be ready on time or he’ll have to discipline you.”
I nodded in agreement, dazed. 5am? Why so early?
I was too excited to focus on anything. I futzed about trying to watch TV or read or find something to distract myself from what was to come and how out of control horny I was.
I caught myself starting to idly rub my clit more than once. The first time, Katie pulled me hand away and slapped me. “No, bad!”
That stopped me in my tracks and turned me on even more. This was a bizarre kind of psychological torture.
Somehow I made it through the day. It was about 8pm, I just needed to kill a couple more hours….and find a way to not play with myself while in bed. I had just finished thinking that when Katie came up to me.
Katie, always in control, had a solution. She walked me to my room. “You have an early morning, you should go to bed now.” She handed me three small pink pills and a water bottle. “Benadryl, it’ll help you fall asleep.”
I took the pills. I still desperately wanted to play with myself. Katie could read me like a book.
“No, you’ve been good all day, you aren’t breaking down now. And I’m not going to babysit you until you fall asleep. I’ll be right back, don’t move.”
She left my room and I did my best to listen. She returned less than a minute later with two pairs of fuzzy handcuffs. She attached one end of each to my headboard and cuffed me there.
I lay in bed for what felt like eternity, and that my clock said wasn’t even thirty minutes. Eventually, my brain started to feel as fuzzy as my wrists. I didn’t even realize I fell asleep.
******************
Katie woke me up at 4:30. My brain was still fuzzy and I moved on autopilot, she gave me instructions and I followed them. I used the bathroom and showered. I ate breakfast.
Matt pulled up in a big brown van at 5am. He parked it in front of the house and opened the side door.
Katie walked me outside and into the van. The tiny part of my brain that was awake noted that I’d never been outside naked before and that it was a good thing the sun hadn’t risen yet. If she was bothered by being naked outdoors, it didn’t show.
There were boxes and boxes of things stacked up in the back of the van. I noticed chips and beer. In the corner of the van was a stool. There was a dildo attached to the stool.
Katie put lube on it while Matt lifted me up and let gravity impale me on the dildo as he lowered me down. I was even hornier than I’d been the day before. I felt delightfully full, I hoped they’d let me ride it.
To my thrill and disappointment, Katie tied my legs and ankles to the legs of the stool so I couldn’t raise myself up at all.
A hook hung from the ceiling of the van. While Katie tied my legs, Matt handcuffed my wrists with my arms over my head and connected the handcuff chain to the dangling hook.
My arms were stretched as far as they’d go. If the hook had been any higher I’d have been held up by the wrists.
Katie put a ballgag in my mouth and buckled it in place. I was still too out of it to question what they were doing, much less protest. “Now, stay just like that. There’s a good girl. Stay quiet. You’re a surprise for everyone else for when you all get there.”
I was in the front corner behind the driver’s seat. They hung up a curtain that surrounded me on all sides except the van’s wall.
“He’ll be back in a bit to start the trip. I have a dick appointment first.”
They shut the van doors and I was left in darkness. I was so tired that the handcuffs and the impalement didn’t even phase me, I drifted off into fitful sleep.
I woke up as Matt climbed into the driver’s seat and closed the door. He started driving and I dozed off again.
I was mostly asleep the entire time. The vibrations from the drive were driving me wild but they weren’t enough to make me cum. I moaned as we went over a speed bump a little too fast and Matt shushed me.
We drove for about twenty minutes before parking. Matt pulled the curtain back a little “Now, be absolutely quiet. The guys aren’t supposed to know about you until we get there. Misbehave and I’ll punish you. Nod if you understand.”
I nodded, wishing he’d take the time to play with me at least a little. He put the curtain back into place.
About two minutes after he did, the side door to the van opened.
“Jerry, get in! We’ve got 4 other stops.”
Jerry apparently wasn’t much of a talker at 5:30am. But then, who is?
We drove for a bit, let someone in, drove some more, let someone else in, rinse and repeat. At the last stop two people got in.
From the chatter, I’d gathered the names of all the newcomers were Jerry, Bill, Josh, Tom, Kevin, and Adam.
Shenandoah National Park is in Virginia and about two hours from the suburbs near Baltimore where we lived. I worked hard to keep quiet every time the van hit a bump.
I did reasonably well, to the point that no one noticed me. We hit the checkpoint at the ranger’s station and drove through. About a minute after that, the road went from pavement to gravel to dirt and got bumpy.
I did my best to be quiet, but, during a really rough stretch, a louder moan escaped my gagged mouth.
Someone pulled the curtain aside and a surprised looking teenaged guy with shaggy blond hair met my eyes.
“Matt, what the fuck is this?!?”
“Shit, she was supposed to be a surprise when we got to the campsite.”
Matt stopped the van. “Katie lent me her little sister for the weekend for us to play with. She’s a real cumslut.”
One of the boys pulled down the curtain completely, leaving me exposed to all of them.
They oggled me for a few minutes and one of them, dark haired and tall with an athletic build, reached out towards me.
“Tom, hands off until we get there.”
The guy, Tom apparently, looked disappointed but lowered his hand.
One of the other guys met my eyes and asked “And she’s here, like this, by choice?”
Well, I was already naked, gagged and bound, and impaled in front of six boys I’d never met before. I was either in denial or starting to gain some confidence. I nodded and winked at him, moaning “Mmmhmmmmm.”
They all looked at me slackjawed. I felt horny, frustrated, and impatient, but it wouldn’t be long until they were fucking me.
We drove for another twenty minutes until Matt parked the van. It had barely stopped before Tom’s hand was on my left breast.
“We need to make camp before we have fun.”
The guys all complained. Matt relented “Fine, you can all cop a feel. Then we make camp. Then you can play with her.”
They scrambled, unloading boxes and supplies.
I watched the erection of seven tents while wondering which of their erections would I’d get to enjoy first.
The next thing I knew, two of the guys whose names I didn’t know and who looked identical with dark hair and freckles, untied my legs. They each kissed one of my inner thighs. I moaned appreciatively.
The ballgag was undone and my wrists uncuffed. Hands groped my breasts. “Thanks, I was getting a little stiff like that.”
They looked at me expectantly and I realized they were waiting for me to come down from the stool.
I blushed. “Could one of you lift me up off this?”
Tom, the tall one, gave me a puzzled look and lifted me up. The look of excitement and shock on his friends’ faces were delicious. “You’ve had that in you the whole time?”
“Yeah, but the real thing feels a lot better.”
A hand tugged on my tail. “What’s this? How’s that staying on?”
I yelped. “Easy, the rest of it is inside me. And I want it to stay that way until someone’s ready to fuck my ass.”
My words were bolder than I’d expected. A hungry look hit all of their faces.
“So what’s the deal. What are we allowed to do with you?”
I looked at Matt. “I promised to do whatever you guys want all weekend. Honestly, I’m looking forward to it, I haven’t gotten to cum since Wednesday.”
I stepped out of the van and kneeled on the grass. “I’m tired of waiting, could one or three of you put a dick in me already?”