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.
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 canlı bahis (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 rosé and given her half a glass to go with supper. I’d joined her and planned to help kill the bottle sooner rather than later so that she wouldn’t be tempted to over-indulge. I’d explained how much stronger wine was than a beer (or cooler) and she’d nodded solemnly at me before trying her first sip.
After supper, I settled into my usual spot on the huge U-shaped sectional. We each had our own corner of the couch, with two cushions in between and our own large rectangular ottoman to put our feet up on. I arranged my laptop on my lap and prepared everything for our new style of “movie night”. My laptop was connected to the large TV with an HDMI cable, completely by-passing Caylee’s parents passworded accounts on the gaming console, and the first video was ready on screen, showing the first frame as a still image.
The frozen frame showed a redheaded woman standing in front of a man who was in the process of removing her top. His hands were wrapped across her stomach, pushing up the material of bahis siteleri her shirt (one of those tank tops that was tight but very stretchy). She had a small enough chest that no bra was needed and you could see the barest inch of under-boob uncovered. She wore only a pair of white panties, fairly simple but with an edging of lace. She was fairly short and her body was very slim. I noticed that her legs were elegant instead of fit and muscular like Caylee’s. I was already starting to get a bit hard from the combination of that frozen frame along with the video thumbnails I’d seen and thoughts of what was to come later on.
As I was reaching for another sip of wine, Caylee bounced into the room and paraded in front of me with two bowls of ice cream. My jaw just about hit the floor and I put down my wine glass. Her previous PJ choice of T-shirts and shorts had been cute and a little bit sexy, especially given how the soft old T-shirt had moulded over her perky breasts. This set of PJs was insanely hot. Even though it could still have been categorized as something innocent, there was something about it that had the innocence pegged as an act and hinted that the woman underneath as a very sexual being. If Caylee’d had her hair in fake little-girl pigtails, it couldn’t have been more clear what she was playing at. The lightweight material had a cute pattern of rosebuds on a white background. She wore a pair of little shorts that only came to mid-thigh and clung there with an elastic and little ruffles at the bottom. The top hung loosely from two wide straps that were a bit frilly on the edges. I think the style would be called “baby doll” as it draped itself outwards from there, the material becoming wider instead of fitting close to her waist. It overlapped the shorts by at least 15cm. You’d think that would make it more modest but in a way it made it hotter because you could picture it as being a little dress, one that would almost-but-not-quite cover her ass and other salient body parts. Overall, it was a kinda confusing but extremely arousing contrast of faux girlishly cute and mouthwatering-ly hot.
She set the bowls down on the coffee table and came to stand in front of me. “Pass me the laptop Matty and I’ll trade it for your ice cream.” Jeez, she was even trying to sound cute. `OK,’ I decided `I’ll play along with your little show but yah, that laptop trade is not happening, babe’. I had gone from starting-to-get-hard to completely-stiff in the time she’d pranced into the room.
“That’s OK, you go ahead and get comfy, I’ll grab it once I get this started.” I replied out loud, keeping my voice casual and motioning towards the laptop and the mouse-pad beside me on the arm of the couch.
“Oh I don’t mind grabbing it for you…” Her smile was a little sly as she struggled to hide her motives. Unlike the women at the beach, whose guile had become second nature with practice, Caylee was a newbie and couldn’t quite manage a poker face. Her eyes attempted an innocent expression on the surface, eyes wide and relaxed, but I could see a slight knowing sparkle in their depths. She leaned forward and reaching out both her hands on either side of the laptop as if to pick it up. The way her top gaped open, revealing a bit of cleavage was not helpful to my predicament at all.
“Nope!” I said quickly, grabbing the sides and struggling not to look down her top. `Oops, that was a little too panicky of a reaction’ I thought. “Um… I’ve got it, really.”
“Hmm…” she said, straightening back up, her eyes twinkling. The corners of her mouth turned up. “Interesting.” I’m sure she considered her little experiment a success and I gladly gave her the win. If knowing her sexy little outfit had given me a boner added to Caylee’s confidence, that would feel like a huge win for me too.
But I refrained from commenting because I did not want to open that can of worms and have an actual discussion about said boner. We watched each other as she settled into the couch, tucking her bare legs to the side and leaning into the corner. She picked up her spoon and started eating, but didn’t withdraw her attention in my direction. My gaze flicked involuntarily over all that bare skin and over the spoon she was slowly pulling out of her mouth. I was helplessly mesmerized as her tongue followed it out, pressed against the upside-down bowl of it, lingering on the very tip before it slowly retracted into her lush mouth.
When I was able to tear my eyes away from her actions and meet her gaze, the blatant awareness and slight smugness I found there told me she knew precisely the effect this was having on me, everything from her long tanned legs to her slow spoon seduction. Wow, Caylee had clearly brought her A game! Had she planned out more than just the outfit, I wondered, or was she winging it?
“You little minx!” I chided with a shocked laugh. “Clearly, you have no need further need of my expert tutelage as you are already a master at capturing bahis şirketleri male attention!” I felt a strange mixture of sexual frustration and pride at just how far she’d come in only a couple weeks. These churning emotions were shot through with a slight sense of fear that her entire persona was an act, calculated to have me drooling over her by the end of the summer only to drop me like a stone. I scrambled to reassure myself it wasn’t possible, that too much of her innocence had seemed so completely genuinely. I was soothed when she immediately dropped the seductress act, perhaps worried I was genuinely upset with her.
“Matty, I’m sorry!” she said, setting her bowl back down and knee-walking over the couch cushions to me. “I guess I’m a little drunk on my newfound knowledge and power. Like at the beach, when guys were checking me out, I just couldn’t believe they were actually interested in me. But I wouldn’t know the first thing to do if they actually approached me and showed their interest. I still need your help. Like, a lot.”
“OK, thanks, I guess. You know… you don’t have to play games with me- or with any other guy for that matter! The decent ones will appreciate you for who you are, will notice you are sexy without any effort on your part. No matter what you wear or say or do.”
“Am I though?” she asked nervously, nibbling on her lip a little.
“Are you what?”
I examined her expression, looking for any sign of coyness or manipulation. But she seemed to honestly want to know. I realized then that her act had been an experiment, not to confirm what she already knew, but to find out what she still wasn’t aware of. She didn’t yet believe she was sexy enough to make a guy interested in her, that anyone would find her beautiful and would want her. Besides the day at the beach, she hadn’t really had any outward confirmation of her attractiveness.
“Of course you are. And I can understand that it’s exciting to have this new… confidence. But I don’t want you to become one of those women that use their sex appeal as a weapon. Who try to manipulate and control guys to get whatever they want. They might attract guys but they mostly attract assholes. And I don’t want that for you. Especially for your- you know, your first time. I’m doing this because I want you to be happy, healthy, and safe.”
“Matt, you’re amazing, you know that?” Her eyes looked genuinely teary at my reassuring words. “How will I ever find a guy who’s even half as decent as you? How does a girl avoid losing her virginity to a complete- to an… asshole?” She emphasized this last word, but carefully. It was almost like she was placing it on the table to examine it’s effect.
Good, she was testing out her swearing, I was happy to hear that. As for the content of her sentence, this was my greatest fear for Caylee’s virginity. The hope that she would be able to avoid these assholes and have a positive first sexual experience was one of the many motivating factors for my quest to equip her with as much info as possible.
“Well…” I carefully weighed my response, wanting her to use this blueprint to avoid the worst guys out there and seek out the ones who were decent human beings. “You get to know him as much as humanly possible, spend tons of time with him, ask him questions. Try to meet his family, ask them questions because they’ll know whether he’s a fraud, ya know? Wait until you know a guy well enough that you can trust him to do right by you. To give you a good first time.”
Caylee had listened attentively to my spiel, considering every word. Her smile grew bigger with every sentence, although it was a mystery to me as to why. I knew I was setting out pretty tall orders, that this would take her a long time and further delay her objective of no longer being a virgin. But I knew it was the right way to go; even if it took her longer, it would help her make that moment as special as she could.
“I approve of your plan 100%” she said, patting my chest gently. I tried not to shiver at her touch but it gave me a warm and happy feeling. I enjoyed it when Caylee found my words helpful.
“Well, we’d better not let our ice cream melt!” I said, trying to steer away from this serious conversation. At least it had allowed for my boner to calm down a little. I set the laptop on the table and replaced it with the bowl in the same spot as a less-effective-but-better-than-nothing shield. `Yikes, that was cold!’ I thought, lifting it back up slightly and picking up my spoon to start eating it. Caylee went back to her own ice cream but shot me a smile with her eyebrows raised.
“Hmm so now you can put the laptop away huh?” she teased.
“I have no idea what you’re talking about.” I fired back but was now smiling.
“Oh I see… so there’s no need to pick it back up again right? You have your mouse right there.”
`Shit.’ I thought. `I’ve painted myself into a corner now!’ It seemed that she had noticed me hanging onto it each night.
“Right, no reason at all.” I retorted dryly. I thought for a moment. “But gee, this ice cream is making me a bit chilly so why don’t you chuck me that blanket?”