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This series makes more sense if you’ve ready Chapters 1 to 5, 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 9 — Friday:
For supper on Friday Caylee and I got take-out as a special treat. Instead of having supper at the table before our movie night, we got everything ready on the coffee table in front of the TV and watched a movie while we ate. Usually we also changed into our pyjamas for the movie (T-shirt and boxers for me, soft old T-shirt with little shorts for Caylee) but we hadn’t yet.
I also took out another of the coolers from the grocery store to give to her. I had bought two packs of four so there were enough for the whole week (plus one) if I continued to give Caylee one with supper. I figured I’d let her have the extra one tonight; after all, I had been buying my own alcohol at her age. All in all, it was a nice kick-off to the weekend.
After the movie, we settled back in what had become our pattern of post-movie discussions. I felt like I had succeeded in creating a space and time when Caylee could feel free to ask me anything she wanted. She often waited until this special time to really open up, changing the subject when I asked her at breakfast if she’d had any success getting herself off the previous night for example! Maybe it was still too hard for her to talk about this kind of stuff in daylight, to acknowledge she was a woman now at age 18, that her feelings and desires were completely natural.
But when it came to this time of night, Caylee would eagerly soak up any info I could give. Unlike her, I’d had the full teenager experience back when I was in high school (and continuing into my university years – 2 of those so far). I’d talked about my girlfriends, my male friends, sex, masturbation, parties, drinking, drugs, you name it. Caylee hadn’t experienced any of it, not one single sip of wine at one of her parents’ fancy parties, not one damn kiss, nothing. It made me really sad for my little cousin and angry at my aunt and uncle for the extreme over-protection; it especially made me determined to get her caught up before some jerk came along and took advantage of her innocence. I’d sometimes become preoccupied with the nightmare scenario of Caylee having a bad experience when she lost her virginity – these thoughts always made me want to run out and punch that future asshole before he could even look in her direction. If only I could predict the future like that!
“So, give me a homework report!” I ordered with an encouraging grin, rubbing my hands together and making her giggle. I passed her a second cooler and she opened it, getting settled and gathering her thoughts by taking a few deep breaths with little sips of her drink in between. This made me very glad she wasn’t wearing her soft old PJ T-shirt yet. It often made it challenging to keep focusing on Caylee’s face and not on the curvy breasts I could plainly see the outline of. Sometimes in our discussions about sex and masturbation, I could even see the barest hint of her nipples. Yep, despite her innocence and inexperience, Caylee was definitely a woman with desires and needs to rival any of us horny young people; she clearly got turned on by our chats, also evidenced by how quickly she’d run off to try my latest tricks or tips to help her with her `homework’ at the end of the night.
If she had been wearing that while breathing deeply like that, I’d be in trouble… or maybe not. Right from the first moment I saw her for the first time in many years, I was distracted by her new sexy all-grown-up body, very curvy but very fit. Caylee had never seemed to notice though, and instead seemed perfectly comfortable hugging me and touching me casually as we went about our day. It made things a bit challenging for me though; I was a pretty typical 20-year-old guy with a sex drive to match – my body did not seem to want to accept the `calm down, idiot, that’s your cousin’ messages from my brain.
“Um… I tried the stuff you got me at the grocery store. The- the lube. It, uhh, definitely made things easier. Like, on a physical level I mean.” Her face turned serious and she bit her lower lip, her blue eyes meeting my gaze with a worried expression. “I think it’s really mentally that’s more the problem.”
Hmm, canlı bahis just as I had originally suspected. And it was really no wonder, given all the crappy attitudes about sex and sexuality that Caylee had absorbed through her parents and school environment. “How so?” I took a swing from my own drink, acting as casually as possible. Like in so many previous conversations, I wanted to project an attitude of complete acceptance of her needs and sexuality, with zero judgment. I kept my body open, arms loose and relaxed, completely laissez-faire.
“I think part of it is, like you were saying right at the start, the shame from my strict upbringing and influences from my super-religious school. Feeling like sex isn’t natural, `good’ girls shouldn’t want it, messages like that. And I just… I find I get distracted and lose my progress. Like, I don’t get into it enough. I don’t get in a…” she lowered her voice and looked down at her drink. “…in a sexy mood, I guess?”. She wiggled her mouth in a really cute way (almost certainly unconsciously) as she fought to express her feelings. She was definitely embarrassed, still working on using the right words to describe sex, but she was making the effort and gaining confidence.
“Even with the story stuff we were talking about starting with? Picturing your celebrity crush or some guy you like?” I reminded her. I’d been sure there was some Hollywood hunk she could imagine to kick-start her fantasy. Unfortunately there was little chance of her being able to picture a guy she’d met in person. The other guys she was exposed to were boyfriends of her female friends, and even then, she hadn’t been allowed to socialize with them much at all. She certainly wasn’t allowed having any boys over to hang out, even in a completely innocent and supervised situation. That was one rule her parents had left me with that I was considering breaking because it was so ridiculous.
“Even that. I don’t have enough to go on. Like, I try to imagine that he’s the one…” she hesitated, glancing up at me for a split second before looking back down, fiddling with the label on the bottle. A pink blush was spreading over her cheeks. “That he’s the one touching me, instead of myself. He takes off my clothes and gets me ready. I pretend he’s doing all the thing you said to do to myself – touching other places, building it up. And then I picture him undressing and… that’s when I stop because I can’t picture that!” She looked so annoyed with herself and there were tears swimming in her eyes. “I’ve never seen a… you know, the thing that guys have…” the blush, the tears, and the fact that she couldn’t even meet my gaze all gave away how hard this was for her to try to vocalize.
“It’s OK, I understand. Try to use the words if you can though, Caylee.” I said gently, trying to be as encouraging as possible. I kept my face serious enough that she would feel certain I wasn’t laughing at her, but not in an angry or disapproving way.
“OK, right. Since I’ve never seen a… a penis.” She almost spat the word out, pushing it so quickly through her lips it was as though she worried the word itself would taste bad. She looked up as if to gauge my reaction. I made sure my face remained free of any negative reaction and even gave her a little smile and a thumbs up. Encouraged, she continued, “So when the guy in my fantasy gets naked I can’t fill in the blanks. And that completely puts the brakes on and ruins everything because it just reminds me of how much of a pathetic virgin I am!”
“Caylee, you’re not pathetic!” I told her firmly. “I suspect if you surveyed a lot of women over 20, they would say they regret how young they were when they had their first time! Some of my female friends have said that they had a negative experience, that they wish they had waited for someone more special. So think of it this way – you have a unique chance to really make it awesome.”
“Do you really think so?” she asked.
“Yah, I really do.” I said, speaking from the heart.
“So, back to my problem. Any ideas?”
I thought for a minute and we sipped away at our drinks quietly. I figured I could introduce her to porn but I didn’t want to scare her.
“A couple of ideas…” I eventually said. “Let me do some homework of my own and gather some pictures to show you on my laptop OK?”
She looked a little disappointed but nodded. I suppose my other solutions and answers had been more immediate but I didn’t want to rush it and do further damage. I shuddered inwardly at the thought of what we might stumble across just typing away in a search engine! I definitely wanted to avoid anything bizarre or even too rough or hard core.
“In the meantime, we have time to watch a second movie tonight since we ate during this one instead of at the table. Want to find a movie that’s a bit racy? Like, one with a little nudity or something?” I suggested, hoping this would provide at least some immediate gratification.
“Can’t on this system – there are parental controls for my account and the other one has a pass code.” she replied, sounded dejected.
“Seriously? You’re an actual adult now!” I bahis siteleri exclaimed. The more I discovered about Caylee’s extremely sheltered life, the more my uncle and aunt pissed me right the hell off!
“Just barely but yah, I agree it’s really sucky.” She set her empty bottle on the coffee table like she was worried she would smash it.
“Not just sucky – it’s absolutely shitty!” Given that Caylee never cursed (and had specifically asked me to curse in front of her!), it seemed as though she’d been told she wasn’t `permitted’ to say even the weakest swear words. This made me wonder if Caylee had ever been allowed to get mad! About anything. Ever.
“It is absolutely… shitty!” she replied, instantly covering her mouth after swearing. But slowly, her hands dropped, a huge smile started to spread across her face and she started laughing. “God, that’s felt so good!”. Her cheeks were flushed pink again, but given her happy expression, I assumed it was from happy feelings.
“Good.” I found myself smiling at my young student. “And luckily, we have a way around those controls.” I explained how I could use my own computer, my own movie streaming account, and just connect it to the big TV with an HDMI cable. “That way, it by-passes your home account completely.”
“Awesome! You set up all that stuff. How about I get us some dessert? And get my PJs on ‘cuz we haven’t yet! Don’t forget to get yours on after!” she said, bundling up some of our take-out garbage and running for the kitchen excitedly.
I logged into my movie streaming account on my laptop and quickly came across a very good choice. It was a movie that I had watched with my friends when it had come out in theatres a few months ago. It was rated R and had a couple decent sex scenes thrown in. Nothing too graphic so hopefully Caylee would like it but wouldn’t feel freaked out. I did remember there was a moment we got to see the male lead’s junk full-on because my (pansexual) friend Nick had loudly called “Woo!” from his seat.
`Of course, Nick!’ I realized. I came up with a revised plan – instead of searching for pics, I could just ask Nick to look through his extensive porn collection. Most likely he had some images in there too, as well as videos. I sent him off a quick email then went to change into comfy boxers and a T-shirt for the second movie.
By halfway through the movie, I’d discovered that watching such a racy movie with my 18-yr-old cousin was a very different experience than it had been with my friends. I was starting to wish I hadn’t worn my boxers when we reached the sex scenes, as I was already starting to get a bit of a `tent’ in them. Luckily, Caylee didn’t seem to notice, as she was completely enraptured by what she was seeing.
I supposed I wouldn’t be able to tear my eyes away either, if I were seeing naked bodies for the first time in my life! I offered to try to pause the frames where the male actor demonstrated his full-frontal nudity skills, but Caylee just giggled nervously and shook her head `no’.
Luckily the last few scenes didn’t have much in the way of sex so my boner had calmed down a little. Once the credits were rolling, I placed my hands loosely in my lap to cover the partial erection before lifting my eyebrow at Caylee and asked “Well? What did you think?”
“Wow!” she gushed, her face flushed a little bit and those telltale hints of nipples showing through the super-worn fabric of her t-shirt. She smoothed her hands down her legs and pressed her thighs together in a way she probably assumed was subtle. “That was really… hot? Sexy?”
“I’d agree with either description! What did you think of that dude’s equipment? Interesting? Scary? Not what you expected?”
“Yep, all of the above. That’s going to take some getting use to I think. But at least I’ve got a starting place.” she confessed nervously.
“And tomorrow you’ll get a closer look along with some variety too – you can pick your favourite!” I joked.
She laughed a little at this and started to get up.
“Listen, I’ll finish cleaning up down here and lock up the house and stuff. You rush up to bed while all of this is still fresh in your mind. Try to put yourself in Beth’s shoes!” I advised her, naming the female love interest. I started gathering up the dishes from our ice cream.
“You sure you don’t mind?” she asked politely. But as she stood up, she was squirming in a way that convinced me that she was still turned on. I didn’t want her to lose those feelings that seemed more elusive for her to hold onto because they were competing against a lifetime of negative messages.
“Not one bit. Go have fun with your `homework’!” I told her, laughing.
“Amazing, this is all so helpful! And I can’t wait for tomorrow night!” she gushed, coming over to me to give me a big hug. With a bowl in each hand, I could only stand there and accept the hug, which was much longer than her previous ones. She came up on her tiptoes to say “Thank you so so much.” quietly into my ear.
I wish I could say I didn’t notice how good it felt having Caylee’s arms around me, her lips brushing the shell of my ear, her curvy bahis şirketleri form pressed so hard against me I could feel her tight nipples through her bra-less shirt. But it was more that I didn’t want to notice. And I hoped to hell she didn’t notice how fast I’d gone from `still a bit hard’ to `full erection’ just from having her body that close to me.
I closed up the house in record time and brought my laptop to bed with me. I needed to find a couple videos to jerk off to otherwise the thoughts of Caylee getting off down the hall would completely overwhelm my brain. But the slutty blonde on my screen, on her knees giving a sloppy drooling blowjob, held no appeal. As I slowly stoked my hard-on back to life, I ended up caving to the mental picture my brain had been playing every night since Caylee had first asked for advice on how to touch herself…
I pictured Caylee naked on her bed, slowly running her hands along her soft curves – pressing her round breasts to herself then sliding her hands down her waist, her soft little belly. I tried to fill in the blanks for those few areas covered by her bikinis when we swam together – did she have small pink nipples or were they darker or a shade of brown? She almost certainly had a full bush on her mound – was it a darker blonde than her hair? I drove myself crazy with these wonderings, all the while picturing Caylee’s small hands exploring her folds, adding lube to slide a finger into her pussy, flicking at her clit. Would she finally have luck being able to come tonight? Would she picture that male model undressing for her, holding his attractive dick towards her? Would she be curious enough to wrap her hands around it, to stroke his length? I imagined what that would feel like, Caylee’s soft hands stroking cautiously, slowly, hesitating in her innocence, an expression of wonder and surprise on her face.
With those thoughts – and who was I kidding, it wasn’t the actor’s cock I was thinking about, it was my own – I rushed quickly towards the edge. I altered my own grip, thinking about Caylee’s small hands wrapped about me, thinking about teaching her how to stroke, instructing her how to touch me. I pictured those wide innocent blue eyes looking up at me and looking at her hands on my cock in fascination. That was the image that did me in, pumping as gently and lightly as I could while still getting enough friction. I bit my lip and tried to contain my moans, not wanting Caylee to hear me from down the hall. That thought and it’s reverse (would I ever hear Caylee’s vocalizations during a climax?) prolonged my own orgasm. Cum shot out and trickled down my dick, running over hands that looked too large, too male, too strong.
After catching my breath, I closed my eyes and prepared for the wave of guilt to hit, as it always did. Shit, why did I keep thinking about Caylee this way? She was my cousin! I groaned in frustration. I knew I had to stop but I also knew there was little chance of that happening while still playing this role of someone who was guiding her towards a sexually-healthy adulthood. I would just have to suck it up and deal with it, focus on her learning and try my best to keep it as friendly and professional as I could.
* * * *
Day 10 — Saturday:
I was eager to show Caylee what my friend Nick had sent me. He’d eventually want to know why I’d asked for that particular favour (especially the dick pics – he knew I was straight) and I’d have to pay the piper but I’d been able to hold off his curiosity for the time being. The day seemed to pass really slowly as anticipation built.
Caylee and I swam away the afternoon, and lounged by the pool but I started feeling like my skin was too tight. Was I really going to do this? With my younger cousin? Thus far, what we had done was a little out of the ordinary but not too bizarre. I had shared a lot of information with her, watched some movies, gave her advice, bought her a couple things to help her in her journey. But tonight I would actually be sharing porn with her. Was this crossing a line? Would it make it harder for me to keep inappropriate thoughts of my cousin out of my head (especially during my own unavoidable jerk-off sessions)? Was I pulling her too far in the opposite direction from the impossibly-pure ideal she’d be forced into, and corrupting her?
It was the typical problem of following the spirit of the law instead of the letter of the law. Technically, providing these images to Caylee was against the rules her parents had set out for her while she lived under their roof. But not only had they sheltered her far too much, they had waited far too long to expose her to any of the “normal” things older teens experienced. By trying to protect her, they were setting her up for some potentially disastrous university years. She was so innocent! It terrified me from head to toe to think about what could happen if she didn’t increase her street smarts. Being smart about sex and having an awareness of her body were some of the most important life lessons she had missed out on. If I helped her with everything except her sexuality, she might continue to feel there was something negative about it, about her own desires. And I didn’t want to have that on my conscience. So… onward. I would follow Caylee’s lead and help out however she wanted me to.
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