This series makes more sense if you've ready Chapters 1 to 7, but in case you haven't, here's a summary of the characters and plot.
18-year-old Caylee lives in a gilded cage, over-protected by her parents and sheltered at her all-girls religious school. They live in a huge house in the suburbs with a backyard pool (Caylee is involved in extra-curricular swimming and diving). Her parents are spending the summer in France and have asked Caylee's cousin Matt to "babysit" her. Matt is 20 and just finished his second year at university. His sister Hannah was supposed to join them for the summer but is spending time with her secret girlfriend instead. Caylee has asked Matt to help her catch up to her peers a little by learning from him about social, romantic, and sexual situations.
N.B.
In Canada, our legal age for alcohol and similar products are much lower (18 or 19) compared to young adults in the U.S. who wait until they are 21.
Chapter 8
Day 15 - Thursday:
Two weeks into our summer visit and our routine hadn't changed all that much since the weekend. Caylee and I woke up around the same time, had breakfast together (usually she prepared the food and I made coffee but sometimes we switched). We did our own thing in the mornings, then met for a light lunch, followed by time hanging out by the pool during the afternoon. If it was too hot outside (or stormy), we'd switch things up with board games or video games.
Caylee chatted with her friends regularly, but hadn't had them over since my arrival. Perhaps she was embarrassed about her parents' desire for her to have a "babysitter". That was still technically my role (which I was getting major bucks for from my wealthy aunt and uncle), even though I did my best to act more as a house-sitter. Caylee's parents called from France fairly often to check in on us, and since I hated to lie, I would mostly just skirt any topics I didn't want to get into. They'd specifically asked about who had been over to the house and I was able to reassure them no boys had been present. They certainly wouldn't suspect I'd been finding loopholes in their rules and allowing Caylee to experience other typical teenage experimentation she'd missed out on (like the one light drink we each indulged in over dinner).
Every evening after supper, we were now watching the videos provided by my friend Nick, foregoing completely regular movies. Caylee would always race up to her bedroom afterwards, eager to try things out. She wasn't reporting much success (certainly no actual orgasm), but her enthusiasm didn't waver. She still had some questions for me, but they were less often about the practical and physical aspects of sex and masturbation at this point. They were more about how to `get in the mood' and how to hang onto it when it faltered. She was noticeably aroused during our video-watching time, but it seemed as soon as she put herself to bed, things would fizzle out.
Caylee's mental blocks were clearly continuing to plague her; she had a lot of trouble staying turned on enough to shut off the constant nagging in her mind from all those childhood role models. Her strict over-protective parents and the teachers at her religious all-girls school had preached so often about what they felt constituted `good girl' behaviour that their voices rang in her head. We talked about that often, and I repeated messages about positive and healthy sexuality over and over, trying to help her rewrite her old, restrictive, and negative patterns.
Meanwhile, after all that talking about sex along with time spent watching porn videos (trying not to spontaneously combust from horniness), I was always desperate to jerk off by the end of each evening. I would wait just long enough to be sure Caylee was up in her room before having a turn with whatever my fave video of the night had been. I would always start out with the best intentions, my focus on the people and acts depicted on the TV screen. But the closer I got to yet another (spectacular) orgasm, the more fantasies of Caylee crept into my thoughts.
The knowledge that she was in her room, naked, trying to bring on her own orgasm as I was racing towards mine, drove me absolutely wild. All the more so because I had given her very specific instructions on how to touch herself to best achieve results, which meant I knew exactly what steps she was taking. I kept thinking to myself, `now she must be skimming her hands over her curvy body', `maybe she's finally teasing her wet pussy', `is she trying to stroke her clit or finger her cunt enough to come?'. Shit, it was a miracle I hadn't raced up the stairs by now, my aching dick leading the charge. Instead I had soaked so many tissues with my cum, night after night, that I'd had to find a replacement box for the TV room. I only hoped like hell Caylee hadn't noticed the switch (since the box of tissues had a different pattern printed on the cardboard) and started to wonder just what I was up to.
My orgasms would always be insanely great after so much prolonged arousal, but they would be followed by the inevitable self-deprecating thoughts. After many nights of beating myself up while knowing I wouldn't change a thing, I had made a bit of a deal with myself. `As long as everything stopped at the end of the summer, what was the harm?', I rationalized. We would continue on with our lives. Caylee would meet some guys in uni (and with our lessons, be better equipped to avoid complete assholes who would only take advantage of her innocent nature). I told myself it was just proximity that was the trigger; she was flirty and touchy with me because I was a handy male. The only one she was allowed to hang out with and one she'd had a crush on when she was younger, even. Once I went back to uni in the fall (many hours away!), everything would surely go back to normal and we'd be like any other cousins.
It was getting really hot as June slipped into July so we very much enjoyed our afternoons by the pool. We had gone on a day trip for Canada Day, driving out to one of the many nearby lakeside beaches, where I'd finally met Caylee's friends. They teased her for `keeping me all to herself' but Caylee stood her ground, saying innocently enough that she wanted to spend time with her cousin after not being able to hang out in many years. The other girls had brought along their boyfriends, whom I had the misfortune of having to spend time with while they chatted. If these guys were any indication of the guys Caylee might meet at uni in the future, I was doubly glad to be teaching her to be knowledgeable about sexuality and to be able to enjoy sex without even needing them!
I could already see evidence of her newfound confidence. Yes, she was still a bit of a shy virgin when it came to actually talking and flirting, but she did seem to enjoy the attention she received, wearing one of the bikinis (borrowed from this group of girls). They accentuated her yummy curves and a body fit from swimming and diving and today's bikini was blue, bringing out her very blue eyes and looking great with her natural blonde hair. Her skin had darkened with a tan over the summer days spent by the pool (I'd arrived pretty shortly after the end of Caylee's school year and exams) and she looked golden all over, with little freckles speckled here and there. The kind that made you wonder if she had freckles anywhere else or just unmarked creamy skin.
While we were at the beach, a hunky older guy (maybe 25 or so) obviously checked her out and chose her to chat up. Out of the women lined up on their towels in the sun, she was definitely the most sexy, but she didn't realize it. Which was maybe part of the appeal. She still held this innocence instead of the coy attitude many other young women at that beach were projecting (that `I'm so hot you should only be so lucky if I allow you to talk to me' type thing I'd seen far too often). Caylee was friendly to the mystery hunk, although she didn't lower her shades to meet his eyes, a tiny unintentional snub. After a few minutes of conversation, she shook her head, and I saw her glossy pink lips form the word `No'. She'd obviously declined whatever he asked her for (her number? a date?). Once he left, she looked at me with this... kinda proud and surprised expression, I guess? I gave her a subtle thumbs up and a grin I couldn't conceal. I even felt kinda proud myself.
After that busy day, we returned to our own little day-to-day routine at the house and I was glad for it. Since it was Thursday again, we had just done another weekly grocery shop to stock up for the weekend. Caylee had asked to try a different kind of drink than the coolers she'd tried during my second week here (but still not beer) so I'd picked up a very sweet
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