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This Chapter works well as a stand-alone but here’s the usual summary of the characters and plot:
18-year-old Caylee’s parents are spending the summer in France and have asked Caylee’s cousin Matt (age 20) to “babysit” her. Matt has been helping Caylee learn about all the things she has been sheltered from her whole life, including romantic and sexual situations as well as figuring out how to masturbate, something she’s had trouble with due to all the negative values about sex she’s been exposed to, especially at her strict, all-girls private school. At the end of Chapter 8, they had their first kiss, Caylee had her first orgasm, and also discovered that she craved the taste of Matt’s cum (not necessarily in that order!). In Chapter 9, they explored oral sex but also had a surprise phone call from Matt’s sister Hannah, who told him that their parents were coming to visit Caylee’s home. Caylee informed Matt she’d be pulling out all the stops to seduce him before his family arrived in case their whole summer visit came crashing down around them. In Chapter 10, Matt helps Caylee experience a small taste of her fantasies, but still holds out on her biggest wish, which is to experience her very first fuck with *him*.
* * * *
Day 20 – Tuesday (11 pm):
I was dreaming of Caylee again.
We were in her bed, a hazy backdrop of purple and white sheets around us.
Caylee was above me, her hands linked with mine, holding them above my head. I felt trapped in her grasp, her strong thighs straddled on either side of my hips, and wasn’t the least bit displeased about my captured status. I loved it when she took control and owned her raw sexuality. To the rest of the world, she probably still appeared to be a shy virgin. But to me, she seemed like a gorgeous flower which had been blocked from the sunlight for so long but had somehow thrived and started to bloom.
Caylee leaned forward and smiled down at me, her blond hair making a curtain around our faces. Her lips were a rosy pink, her skin creamy and sun-kissed. She shifted her hips, making me hyper-aware of the point of contact. It was skin-to-skin and felt like heaven — not sex, not yet, but deliciously close to it, wet skin sliding together. Her bright blue eyes pulled me right in with their expression – excited, loving, lustful, and mischievous. Like most of my dreams these days, there was no hesitation, no real life thoughts and reasoning and trying to be “good”. In the dream world, it didn’t matter that Caylee was my younger cousin. I felt no shame, just the ache of lust from head to toe and everything in between, with most of it focused on a rock-hard erection.
I moaned, feeling Caylee’s wet heat as she rocked against me, her gaze still on me, intense and focused. Her hands grasped mine tightly and I growled low in my throat. “Let me go, let me touch you.” I pleaded to be set free but she shook her head, looking delighted with her own wickedness. I gazed hungrily at her lovely breasts, hanging towards my chest but still so firm and perky, her nipples brushing my skin as she slowly moved. I desperately wanted to touch them, roll them between my fingers, taste them, suck them into my mouth. I thought about pulling my hands free, but was enjoying her enjoyment, so I stayed still and continued to play the role of her captive.
Ever so slowly, she dragged her pussy down my dick, letting the cockhead press against her clit at the top before she pulled herself downward. Each time she lifted up to bring her hips back up, I just about died from the pleasure. I could tell I was leaking pre-cum and it felt like Caylee was adding her own juices to create a wonderful slippery mixture. I started to feel a torturous ecstasy of being a few millimetres from slipping inside her and driving into that slick warmth to be completely enfolded by it. I felt my hips buck slightly, my body taking control without my conscious action. It was torturous to be so still!
My eyelids fluttered shut and my eyes felt like they were rolling back in my head at all the wonderful things I could feel. Even the soft tickling sensation of Caylee’s long hair brushing against my chest was driving me insane with lust. I craved flipping us over in two seconds flat and entering her with one firm thrust, but she kept control, riding me slowly. I started to roll my hips more intentionally, catching the tip of my cock on her entrance, teasing the soft skin. If I were to push a little harder, we’d be there…
Caylee gasped, but managed to lift off before I could actually penetrate her. My fingers flexed in her grasp again, asking to be set free. I was desperate to grab her hips, hold her still. I was chasing the pleasure I’d experienced in every previous sex dream I’d had about Caylee. There, we finally got to join, our bodies moving together in a synchronized rhythm. With all the practice we’d had in my dreams, it seemed that this was reaching a new level of reality. Every sensation canlı bahis felt so genuine, every nerve under my skin sparking with attention.
Yes! I noticed that my hands were free at last. I skimmed them up Caylee’s thighs, enjoying the softness of her skin and the strength of her muscles underneath. My eyes were still closed, so I was hyper-aware of the tactile sensations. She shivered and stopped moving, vocally expressing surprise at my movements, but I kept rolling my hips to keep teasing her with the same rhythm of fucking. I pressed against her entrance, slowly, teasing. Her moan expressed how wonderful and agonizing the feeling was for her as well.
“Oh God, Matt!” Caylee’s voice sounded desperate – breathy, strained, and out of control. She leaned over to kiss me and my right hand abandoned her hip to pull her close to me by threading my fingers into the hair just above the back of her neck. I drew her down to my chest as we began kissing deeply, tongues tangling and breath choppy. My lower body seemed to be moving completely by instinct, out of my conscious control now, engaged in a dance thousands of years longer than my lifetime. My left hand pulled Caylee’s hips forward so that her pelvis and belly were glued to mine, her legs splayed out wider. Her hands were spread out over my pecs, now trapped between our bodies as I cradled her firmly on my chest.
I started to feel like I would die if we didn’t start fucking, like, right the hell right now. Keeping her pulled close with my right hand for a continuation of our drugging kisses, I used my left hand to grab her ass cheek and angle her hips to get the right positioning. Yes, right there, that would be perfect. As we continued to move our bodies together, hips rolling, I kept my dick lined up and pressed a little harder. We were so wet, it would be as easy as always to slip right in…
“Ohmigod Matt, are you sure?” Caylee broke away from our kisses and the question had me freezing in place. That wasn’t right… Caylee never asked this in my sex dreams, she was always more than ready to just go for it. What the…
“Matt? Matt, are you awake? Open your eyes please!”
Oh fuck. I did not open my eyes. Instead, from my absolutely frozen state, I took inventory as the remaining pieces of reality smacked me in the face, settling around me in jarring precision. We were indeed in Caylee’s bed. We were… naked? Maybe not quite. The tightness of my boxer shorts’ elastic came to my awareness, They were low around my hips, which was obviously not where they’d been when I’d gone to sleep. I was holding Caylee as I had been in my dream, right hand in her hair, left on her ass, pulled close against me. Which made me wonder – how much had been real?
For now though, I had a problem to untangle from. I was literally just about to fuck Caylee, and my sudden realization of reality hadn’t done anything to reduce my boner. The wet slippery heat of Caylee’s pussy felt just as incredible as it had in every dream and fantasy. Oh God, it would be so delicious – and so easy! – to just… No. Not like this.
My control felt like a rope that had frayed to the very last millimetre-wide thread. Eyes still closed, breathing heavily, I started pulling myself back from the edge.
“Don’t move.” I managed to choke out the words with gritted teeth. “Please!” I didn’t want to open my eyes yet – the sight of Caylee might undo the effort I’d just made.
“All right…” Caylee’s voice was wobbly and unsure. I felt bad, but first things first, I had to yank my hormones back under my control. I carefully untangled my hand from the hair behind her head and then released my grip on her ass cheek.
“Just… can you carefully get off?” I tried to keep my tone as neutral as possible. Inside I was starting to bubble with a strange mix of emotions – confusion, anger, hurt, and of course frustration, especially of the sexual type. I tried to set it all aside for now – as much as I could anyways. We’d talk and figure this out in a minute. Caylee followed my instructions and soon she was lying beside me, pulling the sheets up as much as she could with them shoved down on my side. Shit, I hoped she didn’t perceive this as a rejection! I didn’t want this to inadvertently cause any of the amazing progress she’d made with the negative values about sex she was fighting against. I took a huge breath and let it out slowly. “Thanks baby. Just gimme a sec, OK?”
“OK, sure.” This time Caylee’s voice sounded slightly reassured, although still hesitant and nervous. I took the time to take a few more deep breaths and tried to slow my heart rate and relax my tensed body. I pulled my boxers back up around my waist and grabbed some of the sheets to pull over myself like Caylee had done. A couple minutes of breathing and pulse-settling later, I felt ready to open my eyes and roll over to look at her.
And of course, Caylee looked absolutely delectable, naked with tiny drops of perspiration, tousled hair from where I’d grasped bahis siteleri it, and love-bitten dark pink lips. It made me glad I had refrained from looking while I’d tried to calm my body down a little. I propped my head up on my elbow and looked down at her face, expression anxious and blue eyes a little misty with tears. I wanted to reach out and stroke her cheek but didn’t trust myself to be able to touch her quite yet.
“So, in case you didn’t just put the pieces together… um, I wasn’t awake for most of…” I waved my free hand around vaguely. “…well, whatever the hell that was. I thought I was having one of my sex-with-Caylee dreams until I heard you ask if I was sure!”
“Oh. Yah, that explains a lot.” Caylee actually looked a bit relieved at this, maybe realizing that this wasn’t a rejection of her or anything like that.
“Glad you are less confused but I am still so confused. How the hell did that even get started?”
Now Caylee looked embarrassed, her cheeks turning bright pink as she looked down. She fiddled with the sheet, which was pulled up around her breasts, but very loosely. “Yah, um… I couldn’t sleep so after you fell asleep, I was doing some… homework.” She mumbled the word then looked up at me pleadingly. Her expression reminded me so much of the old Caylee. Well, her self from a couple weeks ago when she’d been so unsure about all of this.
“You were… trying to get off?” I tried to clarify. She nodded vigorously, glad I’d caught on. “Last I checked, that doesn’t require my dick though.” I tried to inject a bit of humour into my tone, as I was starting to catch on to what may have happened. My anger, hurt, and confusion were melting away but leaving the horniness behind, unfortunately.
“Yes, I even took off my clothes to help me get in the mood. But I just got frustrated with how slow it was. So I – I though maybe a little peak of you naked… to help me try to get off. Especially… well, even thinking about your cock makes me wet so I figured looking at it would really push things along. It did the first time!”
I grudgingly conceded this was true and motioned for her to continue. I kept a stern face, not letting her off the hook quite yet. Caylee licked her lips nervously and my eyes darted there, then seemed to continue downwards without my permission, checking out the soft supple breasts I was already addicted to. God, it was so distracting trying to listen while Caylee was naked! I tucked the sheet more firmly around her, making sure it was pulled up to her armpits. A flicker of a smile crossed her face before she sobered up her expression to continue.
“So, really carefully and quietly, I pulled off the sheet so I could look at your chest.” She traced my pecs gently with the tip of her index finder and the light scratch of her nail made me shiver. “Then I lifted up the front of your boxer shorts. And, um, it looked as though you were already hard in your sleep. So when I tried to make room…” With a hand motion, she approximated the movement of a hard dick springing up from a confined space and I tried not to laugh, knowing how sensitive Caylee was about her lack of knowledge about bodies and sex. “I didn’t know it would do that! Or could do that!” The tone of her voice was a bit surprised but also a little annoyed at her naivety and I had to smirk a little at the combination, turning the palm of the hand that my head was propped up on to cover my mouth.
“You didn’t try to put it back?” I teased. Caylee’s description of what she’d done was really easy for me to picture. Her mischievousness was, after all, one of the things I loved about her! The mental images were not helping me in my boner-control efforts, however.
“Um, nope, I didn’t want to wake you up. Or hurt you! I clearly don’t fully grasp the physics of how everything… works. Bends. All that… stuff. I’ve only see it already hard!” She seemed genuinely concerned, which I found really touching – and adorable.
“Gee, I wonder why?” I said, with an exaggerated leer in the direction of her sexy body.
Caylee gave me a teasing smile of her own. “Mmm, you’ll just have to show me the full range of motion sometime.”
“In the interest of damage prevention, I just might!” I winced at the thought of any potentially-painful mishandling of that most-precious appendage. But of course my dick was jumping at the suggestion of contact. `Down, boy!’ I mentally admonished it.
“So anyways, I did the only thing I could do which was to – carefully! – pull the waistband down and hope the elastic wasn’t uncomfortable for you. It seemed loose enough. So I tucked it out of the way and waited a bit to see if you’d been disturbed. But you stayed asleep so I went back to my lame attempts at trying to fly solo.”
“Hey!” I chided her softly, holding her by the chin and gently directing her face so that she looked right at me. “Never lame.” I softened my stance so she would know I wasn’t angry at her.
“I guess I am getting better bahis şirketleri these days… with such frequent sources of inspiration.” she whispered with a little smirk of satisfaction and pride.
“Brat.” I affectionately kissed her on the mouth, intending to keep it light and teasing but she kissed back with her usual passion and energy and I let myself be consumed by the kiss just a little bit before pulling away gradually. Her blue eyes looked as heated as I’m sure mine were. My still-present erection twitched, like a reminder: `hey, what are we doing in bed with a hot naked chick without some action here?’. I had to admit, my dick had a good point. “It is getting so impossible to resist you, you know that, right?”
She nodded, fairly seriously, then whispered “so why are you then? Still?”.
“I guess…” I sighed. I should be honest with her. “I think the main reason… well, the only real reason left, aside from the guilt – which I think I can handle… I guess I’d hoped to hold it off until after the family visited. I feel like it would make it be too hard to keep it a secret. That it would be like walking around with signs on our foreheads advertising. But then again, I’m already worried it’ll be like that anyways without this last step! I guess I’ve bought into the bullshit idea that intercourse is the only `real’ sex and what we’ve been doing doesn’t count.”
“But it does count.” Caylee’s voice was still low, her expression earnest. She got it. After all, underneath all the awful hang-ups her upbringing had put on her, she was very open and free.
“Yah, it does. I’m seeing a line there where none truly exists. And when I woke up just now, the reason I pulled back had nothing to do with our family. The only thought I had was `not like this’. I don’t want to just fall into sex like, oops, that happened. With you, it’ll be special and wonderful and amazing. I want to go into with eyes open, awake and aware.”
Caylee crept a little closer, placing her arms on my chest and kissed me again, sweet and hopeful. Her blue eyes peered up at me. “So… does this mean you’re finally giving me what I want?”.
I paused before nodding slowly, and she just about knocked me over with enthusiastic kisses. I pulled her back before we fell into another passionate make-out session without even intending to, holding onto her soft bicep, with its play of strong muscles underneath.
“Do you want me to go get a condom? I’ve been tested since my last relationship but if you’re more comfortable with that, it’s totally fine with me.” I met Caylee’s gaze, my expression serious. The decision was completely hers, and I wanted her to be sure. I remembered someone telling me (maybe my sister or even Caylee herself) that Caylee had been started on birth control in her early teens – no surprise given my over-controlling aunt and uncle.
“No, I trust you more than anyone in the world.” Caylee leaned back in to kiss my passionately again. She was practically vibrating with excitement. “And I really want to feel you. You know how much I love your cum.” she whispered. I groaned as I pulled her back close to me.
As we lay on our sides, facing each other and kissing, a plan formed in my head. It would be a way to ensure our accidental “almost” wasn’t remembered as a bad thing. I pulled myself back from the kisses to set up the sexy scenario…
“Don’t think you’re getting off the hook for your sleep sneakiness.” I made sure my tone was stern but slightly teasing. “You still owe me the rest of your story, to catch me back up to where we were when dream-you became you-you.”
“Yes, OK.” Caylee bit her lip, shyly looking up at me. She still looked embarrassed about her actions while I’d been only semi-conscious, which confirmed I was making the right choice with my idea.
“I need to know what you were up to…” I nestled us back into the pillows a bit, making sure my head was propped up. Then, I pulled the sheet away from our bodies. I made a point of re-arranging my boxers so that my cock was placed as described in Caylee’s story, so she would get the full meaning of my instruction when I gave it. And then, aware I was signing away my fate and hoping it wasn’t just my hormones talking me into things, I told her: “Show me.”
Caylee’s eyes lit up with a flash of lust and she grinned. She arranged herself to demonstrate how she’d been positioned after her peek into my boxers, leaning back against her pillows with her legs splayed apart. From my vantage point I could see that her inner thighs were dewy and I could pick up her scent, which of course made my cock twitch and harden even further. Giving me a sexy-but-shy look, a contradiction it seemed like only Caylee could pull off so damn well, she gently allowed her fingers to brush against her pussy, her breathing starting to accelerate a little.
“So I went back to touching myself, enjoying the sight of your body. There was a little drop of pre-cum already. And the head of that cock looked so delicious and soft and…” she shuddered. I fidgeted in place, wanting to touch myself, wanting to touch her. Instead I just lay there, waiting as patiently as I could. “It just looked so yummy I had to taste you.”
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