This is the story of Cassie, as she grows from novice to full-blown cum slut. Part 5.
Hi All,
It’s Cassandra, that is, current time period Cassandra who’s recounting this. My new dom has been having me write about my teenage exploits. She thought my original draft for part five had too much stuff that wasn’t important so I’m going to skip a bit here and there, with just some highlights mentioned. Anyway, back to the story. If you miss me you can see my running commentary with the occasional message in parenthesis.
My parents came home from their business trip. As freelance corporate advisors, they traveled a lot. By the time they came home, I was fed, showered, and, most notably, clothed. I got up from the living room couch and greeted them. A perverse thrill went through me knowing they had no idea what I’d done the past couple days or the giant butt plug that was still occupying my ass. The worst part about my parents getting home was that pretending to be an innocent teenager and being a screamer don’t mix.
The next few days were pretty uneventful, at least in terms of getting off. I’d already lost track of how many orgasms I’d had, but I desperately needed more. Unfortunately, my parents had a home office and it was directly under my bedroom. I didn’t want to risk getting myself off while they were home, I was afraid they’d be able to hear me even if I was screaming into a pillow.
On the up side, they’d decided I was finally old enough to get a cell phone. It was one of the newer and fancier models of flip phone, just released the previous fall. It was thin and hot pink. It had a camera built into it, and it even had an extra display screen on the outside.
(If you weren’t alive back in 2005, smartphones wouldn’t be invented for another couple years, cameras had just started being integrated into phones, and flip phones were all the rage.)
I wanted to message people, but my friends’ cell numbers, the ones who had cell numbers, were all written down on a notepad in my room. When I got home, I managed to add all the phone numbers I knew to my new phone.
My parents had had cell phones for years for business and had paid through the nose for unlimited minutes. (Back then, phone plans had a limit to how many total minutes your calls could be, and a predetermined number of texts you could send. Extra minutes were expensive, each extra text message was ten cents. They added up fast.) After Katie had cost them a fortune two years prior by texting nonstop, they’d relented and started paying for unlimited texts too.
I texted my best friend, Mary. Her parents were loaded and they’d all be away on vacation in California for weeks. She and I had been best friends for years. We talked about what boys we thought were cute, I’d been too afraid to tell her about the girls I thought were cute. We’d both been absolutely clueless about boys and sex. We’d made a pact that we’d tell each other if we’d made any progress on that front. Boy oh boy did I have some progress to report.
They were getting back Wednesday night. We made plans to hang out Thursday.
With two days to go. I went about my business.
Katie had been a bit cold towards me since, well, since I’d left her boyfriend folded in half with a dildo in his ass and his own cum all over his face. On Wednesday, dad went to the dentist while mom was out grocery shopping, we had an hour or so home alone and finally had a chance to talk for real.
It was just as I thought, she was really mad at me. But then I learned the extent of it.
Apparently, while being folded over like that for hours, Matt could barely breathe. It was only a few minutes after I’d left the room that he’d realized it. He’d spent an agonizing five hours struggling to breathe, afraid he was going to suffocate.
A (proper) dom/sub relationship was built on trust and respect. She’d left him in my care and I’d nearly killed him. The trust they’d built had been severely damaged, possibly beyond repair. It’d taken everything she could to convince him to stay with her.
I felt awful, truly awful. They had a lot of work to do, but she’d promised him she’d agree to anything if they could try to move past it. I hugged her and, in turn, promised that I’d do anything I could to help make things better between her and Matt since it was my fault.. She smiled darkly at me. “It’s funny you should offer. We have a few things in mind for you to do, chiefly among them, Matt gets your virginity.”
I blinked. I tried to play it cool, like she was asking some great task. I probably should want to save my virginity for someone special. In reality, getting sem-forced to let her boyfriend fuck me just got me wet. (Yes, yes, we could debate all day about if getting fucked in the ass counted as losing one’s virginity. I’m just relaying what Katie said.)
Evidently, I don’t have much of a poker face. Katie rolled her eyes at me. “I knew that wasn’t going to be embarrassing enough for you. There’s other stuff you’re going to have to do. That’s just the start of your punishment. Honestly, Matt’s never really had a taste for being dominant, but he’s really excited at the idea of getting revenge and evening things out. He’s got some brutal, humiliating, and kind of depraved things planned for you.”
I must have looked a little scared because she quickly added “Don’t worry, unlike when you overdid things with him, I’ll be there to make sure you’re not in danger.”
She went back to her room and I went to mine. It was hard to tell what had me more excited, getting fucked by Matt or the prospect of being made to do unknown, humiliating sexual acts. I didn’t realize it at the time, but I was more aroused than I’d ever been. This called for something more than rubbing my clit.
I wasn’t crazy enough to try using the saddle again, yet. I’d hidden the dildo Katie had given me so my mother wouldn’t find it. I’d finally measured it properly, it was six inches long, an inch and a half in diameter.
Actually, I’d finally measured everything properly. I’d overestimated the size of the dildos that could attach to the saddle, I’d thought they were seven inches wrong, they were five and a half inches long and maybe an inch wide. (I guess guys aren’t the only ones who get sizes wrong.) The original butt plug Katie had “given” me was four inches long and inch and a half wide. The new butt plug she’d put in me after Matt fucked my ass the second time was five inches long and two inches wide. I hadn’t measured it myself, but Katie told me Matt’s dick actually was seven inches long; I longed to get that dick, or really any dick, back inside me.
The dildo had a wide base. I put it on my desk chair, held it in place with my left hand, and started to ride it while rubbing my clit with my left hand.
I thought about Matt fucking me like he’d fucked my ass: lifting me off the ground and savagely fucking me. I thought about getting my cunt pumped full of cum. I thought about all the different humiliating things I hoped they’d make me do. I hoped they’d make me get fucked by lots of dicks. Ugh. I wanted someone to cum in my ass again. I wanted a LOT of someones to cum in my ass. And mouth. And pussy. I wondered if they’d make me do things to people outside my bedroom, in public, outside, anywhere I could get caught. I wondered if they’d tie me up again. I wondered if I’d get cum on again. A million thoughts went through my mind while I played with myself, each more depraved than the last. Finally, I screamed as I had a big climax and all but collapsed, propped up by the chair.
*****************************
Thursday finally came about. I got my mom to drive me over to Mary’s house. Mary’s house had an inground pool; I put my swimsuit, among other things, in my backpack.
We’d been texting a little now that I had a cell phone, but we hadn’t seen each other in weeks. I hugged her when I saw her.
Mary was gorgeous. At 5’6”, she was a little less than half a foot taller than me. She had an athletic build and breasts a bit bigger than mine. We talked about cute boys all the time, but I’d never had the courage to talk with her about the girls I thought were cute, much less how pretty she was.
She looked at me with a gleam in her eye and said “My room, now. I have news.”
As previously mentioned, her parents were rich. Their house was two or three times the size of mine. Similarly, her bedroom was twice the size of mine, at least, if you included the private bathroom and walk-in closet. She had a queen sized bed, two giant bookshelves, an entertainment system, and a desk with her own computer on it.
We sat on the bed. There was a smug look on her face as she told me, “While we were on vacation, I kissed a boy. I let him play with my boobs. I even let him finger me a little. I even jerked him off.”
She looked so proud. I wasn’t really surprised. We’d both been absolutely clueless about everything related to sex. Hell, I hadn’t figured out how to play with myself until I’d seen Katie in action. To clarify, I’d tried touching myself several times and it’d felt good, but the times I’d tried it the building pressure had scared me and I’d stopped. Mary had been in a similar boat.
Mary finally had a breakthrough, she’d finally kissed a boy, she’d let him feel her up. She was so excited to tell me about everything. I felt kind of bad. I was going to one up her so bad she’d think I was Mario.
“Mary, that’s amazing! Tell me everything….then I’ll tell you my news.”
“You have news too?!?” Mary asked, shocked.
“I do, I’ll tell you everything after you tell me about the boy from your vacation. Just promise you won’t hate me.”
She gave me a quizzical look. “Why would I hate you? I’m excited for you.”
She gave me a rundown of her time on vacation. A couple days into visiting California she’d met a cute boy who was also on vacation. They ran into each other a couple times and he’d asked for her number. They’d gone to dinner then gone out for dessert. He’d kissed her on a bench after they’d finished their ice cream. She had her own hotel room and they’d gone to it and made out. He’d tried to lift up her shirt and she’d let him. He’d played with her breasts for a while, which she’d loved. He’d asked to take off her pants. She’d decided to go for broke and let him finger her. He asked if he could fuck her but she was afraid she’d get pregnant. Instead she’d given him a handjob. Her only real regret was that he’d cum but she hadn’t.
Then it was my turn. I told her about walking in on Katie and Matt. I told her about playing with myself, about Katie’s offer, Matt eating me out, the sixty-nine and swallowing his load. I told her about everything: Matt cumming down my throat as I collapsed, Katie lending me Matt for an evening and all the things I’d done with him. Then I told her about the day after: getting a facial, the series of reality-shattering orgasms that made me pass out, and getting fucked in the ass. I even told her about Matt and Katie’s plans for my virginity.
“...and yeah, I’ve been wearing that plug and sleeping naked ever since. It’s all been amazing.”
Mary’s jaw had dropped. Seriously, I mean it. Her jaw literally dropped while I was telling her everything. A look of absolute envy and lust was on her face. “You’re wearing it now?”
I confirmed I was. “Can I see?”
That seemed fair. I walked over and locked her bedroom door. Then I pulled down my shorts and underwear and bent over. “Oh my God! You’ve really got something in your ass!”
“Mmmm, yep. It’s great. I feel kind of hollow without it.”
“Can I…can I touch it?”
Oh, I liked where this was going. If I was lucky, I was about to have a beautiful girl playing with me. Actually, not just any beautiful girl, my best friend who I had a massive crush on.
“Absolutely, go for it.”
She reached out and put her fingers on the base of the butt plug. She tugged on it, admittedly a little too hard, but it still felt great. I gasped and moaned slightly. “Easy, it’s narrower right after the base and then gets wider.”
“And it’s really inside you?”
I gave her a level look. “It’s right there. Here look.”
I gently pulled on the base of the plug and felt my sphincter stretch a bit. I pulled the plug out of me and she marveled at it. “Oh my god. That’s so big, how do you fit it in?”
“I’ve practiced and stretched it a lot.” I pushed it back in, most of the way. “Do you want to try?”
Her hand replaced mine, and she pushed the plug in most of the way and then pulled it back out until the tip was barely inside me. She pushed it in again. I moaned. I could just barely see her face. She was staring at my stretched hole in amazement.
“I, uh, brought another toy with me too. Would you like a turn with it?”
She froze, midway through pulling the plug out of me again. “You do? I don’t think my butt can take something that big”
“I do, and I meant your pussy. . I feel bad Tyler didn’t make you cum when you guys were together. And what you’re doing feels really good. I’ll tell you what, lie back on the bed and I’ll use it on you.”
She bit her lip. “Fuck, why not. But we can’t tell anyone, I don’t want people thinking we’re a pair of lezzies.” (In hindsight, that was a hilarious comment, but we’ll get to that later.)
I pulled the dildo out of my bag. She looked at it with naked lust.
She took off her jeans and underwear. She laid back and rested her head on a pillow.
I spread her legs enough so I’d have access to her glistening pussy. This was a dream come true. I put the dildo on the bed in easy reach then inserted a finger into her slit and she moaned appreciatively. “I need to warm you up before you can take that.”
She was already wet. I worked a finger inside her. With my left hand, I slowly started rubbing her clit. She moaned louder. I wanted to lick her so badly, but I fought the urge. I had her on the line but I needed to reel her in before there was a chance she’d let me do that.
I worked a finger in and out of her. She gasped as I slid a second finger inside her. “Oh fuck, Cassie that feels amazing.”
Good, excellent even. I worked both fingers in and out of her for a few minutes and Mary’s breathing got faster. At this rate, she was going to cum before I even got the toy in her. I looked up at Mary’s face. Her eyes were closed and there was a look of ecstasy on her face. Oh, what the hell, let’s give it a shot.
I leaned over and planted a quick kiss right above her clit then pulled my left hand away and replaced it with my tongue. Mary gasped, looking down “What’re you? Oh fuck, that feels good. Keep going.”
YES! I licked her clit eagerly as I fingered her pussy and lost track of time for a while. In the background, I could hear Mary moaning more and more frequently. Her breathing hitched and a louder moan emanated from her mouth. I kept going and her body tensed as she came. I didn’t stop. She came harder and her legs jerked a couple times. I slowed my pace and her climax tapered off.
I looked up at her and our eyes met. “Cassie, what was that?”
I blushed. “I, uh, the idea just kind of popped into my mind, I hope you didn’t mind it. Now that you’re warmed up, want to try the toy?”
She looked conflicted for a moment before her face went red. “Fuck it, if that was an orgasm, I want another one.”
I didn’t need telling twice. I was still positioned at her side. I took the toy, spread her lips, and slowly slid it inside her. Mary’s entire body bucked. I slowed my pace. Eventually, I’d fit the entire dildo inside her. I started pulling it back out at the same pace. This went on for several dozen repetitions.
Mary watched me work. I moved my gaze from her cunt to her face. Time to take another gamble. “Take off your shirt.” Her eyes met mine. She nodded and sat up lifting her shirt over her head. While she was up, I took my hands off the dildo and undid her bra.
Perfect, now she was naked. I gently pushed her back onto the bed. I started moving the dildo in and out of her faster, with just my right hand. As I did, I leaned my head over her chest and licked her right nipple. Mary let out a gasp and then a moan. “Fuuuuuuuck.” I sucked on it for a while, flicking it with my tongue occasionally.
I leaned farther over, moving my mouth to her left breast and repeated the process. I was fucking her with the dildo at a steady pace now. I kept at it until she came a second time.
We were both panting. I hoped she’d return the favor.
Our eyes met and I felt a tension between us inviting me in. With one hand still holding the dildo inside her, I leaned my body farther up and kissed her. She froze for a second then returned the kiss. We made out passionately for a few minutes. By now, I was lying next to her. Finally, she took the bait and lifted up my shirt. My breasts were small, I hadn’t bothered wearing a bra.
“I guess it’s my turn.” She rolled me onto my back and took one of my nipples into her mouth. I let go of the dildo I’d been pressing firmly into her and let her take over.
She licked and sucked my nipples. Her hands found my slit and started rubbing me. I moaned.
Her mouth met mine again and we kissed passionately while she worked a finger inside me. She went a little too fast and worked a second finger inside me. A week ago it would have been uncomfortable or maybe even unpleasant. Now the sudden stretching felt welcome.
She went back to sucking on my nipple and I pushed her head down toward her hand. She froze for a second, said “Oh, what the hell,” and basically crawled down by body, kissing and licking the entire way. Her mouth met my mound and an electric current shivered through my body. She started licking my clit as she worked a third finger into me. Between what she’d been doing with her hand, what she just started doing with her tongue, and knowing I had a gorgeous girl doing this to me, pressure and pleasure were building rapidly inside me.
In less than a minute I was gasping between moans. I knew I was going to cum soon.
I looked down at her and said “I’m close, don’t stop for anything.”
She licked and fingered me even more intently. I knew I was seconds from cumming.
Here’s where I knew we’d have a problem. One of the many things I learned over the past week was that I screamed whenever I had a big climax. I didn’t want anyone knowing what we were up to.
I grabbed the pillow I wasn’t using, put it over my head, and pressed down as a massive climax shook through me. My back arched as my legs spasmed. My arms locked and pushed down harder involuntarily as I screamed into the pillow. Mary stopped for a split second and then kept going. My orgasm lasted at least half a minute. Mary slowed her pace as it subsided.
I moved the pillow off my face as she looked up at me. “You okay?”
It took me a moment to remember English. “Uh, oh, fuck. Fuck yes I’m okay. That was amazing.”
We looked at each other awkwardly. Our friendship had just taken a very unexpected turn. I’d better break the silence.
I was just inhaling so I could speak when Mary spoke first. “Uh, so, um, what would we do about this? Because I like boys.” (Sorry to all you bi and pansexuals out there, we were young and dumb.)
“I like boys too. How about this? We keep things mostly the way they were, but if we’re horny and don’t have a guy around we…help each other out.”
Mary’s face brightened. “That sounds like a great idea. That was a lot of fun and I want to do it again later. But I also want to date boys.” (Given how much kissing and how many romantic things we’d wind up doing, time would show us we’d be in denial about what kind of dynamic we really had. Spoiler alert, the compact we made would wind up lasting two and a half years before we admitted we were actually in a relationship.)
There wasn’t enough blood left in my brain to make another coherent sentence. “Boys are good. I want to get more dick in me.”
We stared at each other for a long second before we burst out laughing. Mary climbed her way back up my body until our faces were next to each other. We just leaned on each other (cuddled) for a while.
Mary looked at me. “Let’s get our swim suits and take a dip. Do you want to stay over tonight? Dad’s smoking a brisket for dinner.”
I smiled and agreed. We got up a couple minutes later. As I reached into my backpack for my two piece, I grabbed my phone and texted my mom that I’d be sleeping over at Mary’s.
We headed downstairs, through the house, and out the back door.
We spent most of the afternoon swimming and laying next to the pool soaking in the sun. We got a little….rowdy applying sunscreen to each other.
Finally, Mary’s mom came out and let us know dinner would be ready in half an hour.
We wrapped ourselves in towels and headed back up to Mary’s room to shower and change.
As I shut her bedroom door, Mary surprised me by grabbing my sides and kissing me without warning. I kissed her back passionately and we meandered our way to her bed. She broke off the kiss telling me she wanted to cum again. I wanted both of us to cum again but we definitely didn’t have time to do that for both of us and shower. Instead, I made a better suggestion.
I took off my bathing suit and let it drop soggily to the floor. I climbed onto her bed and lay face up with my head as far from the bottom of the bed as my feet were from the top.
“How about this? Crouch over me facing the headboard. Then lay down on top of me. That way we can lick each other at the same time.”
Mary hesitated for a moment before agreeing. She stripped off her bikini faster than I thought possible and followed my instructions to the letter.
Her pussy hovered right above my face. I started licking her slit as she leaned forward and started doing the same for me. It took a little bit for us to get used to this new position but then we really went to town on each other.
We knew we were in a time crunch so we held nothing back. In only a few minutes we were both panting and I was about to cum. I wrapped my arms around Mary’s waist and pulled her onto me more thoroughly. I screamed into her pussy as I came, trying and failing to keep licking her. Apparently the vibrations her pussy was muffling were enough to send her over the edge because Mary suddenly had a climax of her own.
It took a little while for our orgasms to subside. We stayed in that sixty-nine position for a couple minutes. Then we scrambled off the bed and to the bathroom to get showered.
In the past, we’d shower one after the other. It was boring just waiting around for the other to finish. This time, we showered together.
The hot water poured over us and we helped clean each other’s body. Having hands everywhere got us turned on again and we wound up making out again. Without planning, our hands found their ways to the other’s pussy at the same time. We fingered each other to orgasm.
This time, Mary came first. Feeling her body tense, trying to remain standing while she came, and her moaning into my mouth pushed me over the ends. I screamed as quietly as I could into her mouth as I came too. I’m pretty sure it was a miracle we managed to stay standing.
We exited the shower with about five minutes left before dinner. We toweled off, got dressed, and headed downstairs.
The dinner was amazing. Mary’s dad had slow cooked the brisket for most of the day. Her mom had made string beans and risotto to go with it. Mary’s older brother shot me occasional looks, which I ignored. We ate our fill and headed back upstairs.
We cozied (cuddled) up in Mary’s bed and turned on the TV. I was as jealous as ever at the fact she had not only had a TV in her room but she had a cable box in there too. (Streaming services weren’t a thing yet, they wouldn’t be for another couple years.)
We stayed like that for hours until it was time to turn out the lights. That’s when we started fooling around again.
We spent a lot of time kissing and rubbing each other. I showed Mary how to suck dick by demonstrating on the dildo. I’m pretty sure I impressed her with my newly acquired skills, especially my ability to deepthroat. Six inches isn’t exactly enough to deepthroat, but I took that sucker like a champ as I fit the entire thing into my mouth. I could taste Mary’s pussy still on it from before. Mary tried to do the same but only got about two thirds of it in her mouth.
We fooled around for hours and I lost track of how many times we got each other off. My most memorable was Mary fingering me and licking my clit while I blew the dildo. Mary’s most memorable was making out with her while she sat up and rode it.
All in all, we wore ourselves out staying up until almost 3am. We fell asleep naked and cuddling and woke up holding onto each other for dear life.