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*.
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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 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.
