This series makes more sense if you've ready Chapters 1 to 8, but in case you haven't, here's a 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 - she also needs help figuring out how to masturbate because she's had trouble getting herself off. 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!). Caylee convinced Matt to sleep in her bed overnight, which brings you up to date for this morning after...
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Chapter 9
Day 16 -- Friday:
Going to sleep beside my beautiful cousin Caylee had been extremely tough. She'd fallen asleep quickly, likely exhausted after her first sexual explorations. She'd experienced so many things the night before: her first kiss, first orgasm, first time seeing a naked male body, first time touching a dick, first time tasting cum... No wonder she was fast asleep the moment her head hit the pillow. And yes, the owner of that body, that dick, and that cum was me.
Which was why I had lain awake a while longer, my mind ruminated over absolutely everything, wondering how the hell things had gotten to this point. I'd thought of the story of the frog in boiling water - the temperature changing so slowly, he didn't realize he was being cooked until it was too late. Everything about Caylee's plan had seemed so simple and innocent at the start. Then it had shifted so gradually, and
wham!
Suddenly my cousin was crawling all over my lap and we were making out. I felt sympathy for my amphibian friend indeed. Although I suppose I'd have to concede that this zone of sexual insanity was more pleasant than a pot of deadly hot water.
Caylee's plan had been for me to help her catch up to her peers when it came to "normal" young adulthood things... Two weeks ago, I'd gladly agreed. I'd started helping my cousin learn about all the social things she had been (and still was being) completely sheltered from. It started with things like friends and parties, but when she'd asked for advice on how to get herself off, I'd wanted to help. My original purpose had been to teach Caylee about sex so that she would have positive experiences and feelings about herself and her body. Oh how morally sound my original goals had been. I certainly hadn't planned to be an active participant in those experiences but I hadn't been able to say "no" to her either.
As much as I'd tried to purposefully lock away any doubts or guilty feelings in order to just focus on giving Caylee whatever she needed, of course they still existed. In that dark corner of my mind, they resisted my efforts to box them up for the rest of the summer. Instead of sleeping, I worried over the possibility that Caylee would have those same regrets and self-recriminations as well. What if I'd managed to accomplish the exact opposite of what I'd intended? What if, instead of erasing years of negative messages about sex from her religious all-girls school and over-protective parents, I had just given her new things to feel ashamed about? I was surprised to wake up and find I'd actually slept for a few hours after my mental tossing and turning.
When I did wake up, I found Caylee already awake, head propped up on one elbow, watching me. The sheets were pooled around my waist, leaving my naked chest bared. Thankfully, I felt my boxers still in place, keeping my unsurprising morning wood contained. I'd agreed with Caylee's plan to sleep in the same bed only if she agreed that we'd have our pyjamas on and abandon any thoughts of further sexual shenanigans for that night. She was still wearing the cute PJ set she'd surprised me by wearing last night instead of her usual soft T-shirt and plain shorts - this set was white with little rosebuds and had little ruffles on the straps of the baby doll top and the tiny shorts. It was a combination of sexy and innocent that I found unbearably hot.
"Morning..." I said cautiously, meeting her bright eyes and happy smile. Even though it was first thing in the morning, Caylee looked beautiful. Her blonde hair was tousled around her head, messy from sleep. Without make-up, her face looked impossibly young, younger than her 18 years. She possessed a natural beauty giving her a healthy glow to her face, fresh pink lips, and sparkly bright blue eyes. Her breath was minty fresh (fresher than mine, I was sure) so I assumed she'd been to the bathroom already while I'd slept hard after being up so late with my nagging thoughts - apparently hard enough to not notice her getting in and out of bed beside me.
"Good morning!" she replied cheerfully, beaming down at me. She set a hand on my shoulder and I moved to have my head propped up a little more on my pillows. Well, technically Caylee's pillows; she had wanted us to sleep in her room instead of joining me in the guest room. If anyone needed proof of how much my aunt and uncle had loved doting on their only child, this lavish room would be enough. Pale purple walls with a darker accent wall, mini chandelier, huge bed with white fluffy bedding, little sitting area with a TV,
chaise longue
, and love seat. Through the huge windows with at least two layers of curtains, morning sunlight slanted in.
The room was also proof that her parents still saw Caylee as a girl instead of as a young woman - no wonder she had trouble staying in a sexy mood when she came to bed and attempted to get off. Actual teddy bears lined a shelf over a wall filled with photos of her childhood, a few framed pieces of homework/artwork clearly from Caylee's elementary school days, and ribbons from swimming and diving competitions. The stuffies were arranged such that they were actually looking towards the bed - I made a mental note to put them away sometime soon so Caylee wouldn't lose what progress she'd made last night.
"Sooo... how are you feeling?" I asked, nervous to hear the answer but aware that I needed to ask to be sure.
"Matt, I'm fine. Better than fine! Why do you look so worried?" she said, her hand finding it's way to my shoulder again, stroking the bare skin it found there ever so slightly.
"I just- I thought you might have had regrets over... anything." Or everything.
"I absolutely don't." Her conviction was firm. "Why? Do you?"
"I don't think so. I'm trying very hard to not feel... like a terrible person I guess?" I winced.
"Well, I would hate it if you felt that way." Caylee continued stroking my skin, her eyes luminous and her expression quite happy. "Because that couldn't be farther from the truth. You're the sweetest most amazing person I've ever known. I feel really happy that
you
were the one to teach me all those things and be there with me to have those new experiences. Not some asshole guy that doesn't care about me at all." Her voice sounded calm and very mature. No sign of the shy virgin today.
"I do feel really glad about that too." I admitted. It was true - one of my biggest motivations for starting down this path with Caylee in the first place was to avoid her being taken advantage of by all the jerks I knew were out there.
"Good." she said with a tone of finality, as if everything was settled. "'cause I'm not letting you off the hook yet. I've still got a lot to learn." I couldn't help but smile at all her reassuring words and confidence about what she wanted. She'd had her first taste of sexual experiences, had loved it, and was willing to fight to get more.
"Oh, I'd say you're catching up to your friends quickly enough!" Considering most of them had been kissed around 12 or 13 years old and likely hadn't been naked with a boy for at least a couple years after that time, Caylee was moving forward at mach speed.
"Well, good, I'm hoping to be totally caught up by university." She settled in more closely beside me, resting her head on my shoulder. We sat in silence for a minute, enjoying the cozy connection of warm skin to warm skin. Caylee's hand traced light patterns on my chest and she commented that she really liked waking up with me.
"Me too." I placed my hand over hers, holding it to my chest. My morning boner had deflated somewhat during our serious conversation but I suspected I was only a few touches away from rekindling the fires.
"So does that mean you'd be OK sleeping in here for the rest of the summer? I'd really like that." she looked up at me hopefully. I chewed my lower lip and considered this proposal. There was no way I would survive that without caving to whatever she wanted, which would likely be a repeat of last night's insanity. And what if she wanted more than we'd already done? It was bad enough that we'd both masturbated in front of each other, seen each other's naked bodies, but Caylee had been so close to me when I was close to coming and hadn't been shy about elbowing right in to touch my cock and taste my cum. In fact, she had become extremely forceful about her craving for it!