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This series makes more sense if you’ve ready Chapters 1 and 2, 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 3 – Sunday:
On my third day, I caved to Caylee’s requests to join her in the pool. I’d brought a couple of swim trunks along. The pool had a diving board but I was more into the hot tub. Sometimes I would sit there and watch Caylee dive. She was actually really good!
Over supper, Caylee peppered me with a bunch of questions about typical high school stuff — friends, parties, what we kids did for fun. It was really shocking to me how sheltered she had been. I was happy to be a source she could trust.
We again put on a movie after cleaning up our dinner dishes. During the day, I had been using my laptop and during our post-movie chat, Caylee motioned to it and asked if now would be an OK time for her to borrow it.
“Of course! What do you want to look up? Want a hand?” I offered, eager to continue being helpful.
“It’s super embarrassing.” she mumbled in the general direction of her feet as she sat cross-legged and pulled the laptop into her lap where I couldn’t see the screen — she was facing me with a couple of couch cushions in between us, scrunched into one of the corners of the huge sectional as far back as she could.
“Well I’ve told you a lot of super embarrassing stories from my teens years right?”
This got a smile out of her. “True” she admitted.
“OK so as I’m sure you’ve guessed, I’m still a virgin. Between the all-girls religious school and my parents’ strict social rules, I don’t see that ending any time before I go to university!”
“That sucks.” I sympathized, contemplating what that would be like and realizing how depressing a situation it was. I remember what it had been like to be 18. I was pretty damn obsessed with sex nonstop – had been for many years before that too! I had already lost my virginity to one of my classmates during the summer between Grade 10 and Grade 11. Picturing a virgin Caylee at university was like seeing a lamb off to slaughter.
“And of course a lot of my girl friends brag about their boyfriends — they have the freedom to go on dates and some of their boyfriends have cars and stuff that they can make out in. So obviously I feel pretty left out. And like I said, some of it goes right over my head.”
She took a deep breath. “Problem is, I’m still a teenager, same emotions and feelings and… desires and stuff.” Caylee didn’t want to seem to meet my eyes anymore. Wow, she must be really embarrassed, I thought.
“Of course you are!” I tried to reassure her. “There’s nothing wrong with you, it’s your parents that are putting these super tight fences around you.”
“Right, well there is something wrong because I don’t know how to correctly… make myself feel good, ya know?”
I had to puzzle this out for a second and then I clued in to what she was talking about. I knew I had an important job to do here — this young woman was already feeling a lot of shame about her body, ingrained from years of her parents’ shitty values. I wanted to help her turn that around, not make it worse.
“I’m really sorry to hear that Caylee. Getting yourself off is always a good option for teens when they don’t have girlfriend or boyfriend or hell, even when they do. Everyone should be able to make themselves feel good.”
She finally looked up and met my eyes and hers were brimming with tears. “You don’t think I’m a complete moron for not being able to figure stuff out? I mean, even our stupid school had sex güvenilir bahis ed but it was back when we were like, 10 years old and completely focused on A — periods and B — the evils of sex and the wonderful benefits of abstinence. So I have like no information to go on.”
“I don’t think you’re a moron — I can only imagine the kind of guilt and shame that might be holding you back because your parents and your school don’t understand that sex is a natural thing. I mean, if a higher power created us then they created us to have these urges right? And yes,the world has changed and people aren’t ready to have offspring in their teens anymore but the point is that our bodies are still driving us in that direction. Honestly, I think masturbation is an awesome solution for people who want to keep their virginity!”
She giggled at this one. “That actually makes so much sense! But I doubt anyone at school would agree with your theory.”
“Sadly, no. OK so let’s tackle this. What do you think is the biggest barrier? Are there myths or things you’ve heard that you’re wondering about? Is it the emotional barrier that’s preventing you from relaxing or what?”
She thought for a moment and confessed “I have like, tried, you know. But I do think I’m missing info about how to do things properly to achieve… results, let’s say. I need an instruction manual. I feel like I’m blindly poking around in the dark. Literally.”
“OK well let’s start by searching that — an image of female anatomy so you at least know what’s what and what’s where.” I came to sit beside her, took the laptop back, and quickly pulled up a search. “Also, I know you feel super embarrassed, but try to use the words if you can. Once you know them. By results, do you mean being able to give yourself an orgasm?”
Silence. I looked up from my searching to see Caylee looking a little stunned.
Finally she shook her head a little and squared her shoulders, finding her confidence. “Yes, that’s what I mean. Might take me a bit to say the actual words though.”
“No worries, we’ll work on that.” I gave her what was hopefully an encouraging smile.
We spent some time looking at images and I used my knowledge of what other girlfriends had liked when I was fingering them (or going down on them) to try to give Caylee the instruction manual she wanted.
“OK so try this out, consider it a homework assignment. Try to get in the mood with some kind of story in your head first. Maybe there’s a celebrity or something you can imagine is like, kissing you and touching you?”
“Yah.” she blushed a pretty bright pink across her cheeks. “I’ve got that part covered.”
“OK so think about that for a while to get started. Go slowly, touch yourself in other places too. Try to discover your erogenous zones — could be your neck or ears. Many women have sensitive nipples as well. Just keep experimenting to see what feels good for you. When you reach your vulva, try going slowly there as well, don’t go right for the clitoris even though you now know it contains all those wonderful nerve endings. That’ll help build things up for a better orgasm. And when you do go there, try different motions. Side to side, up and down, going in circles. Everything is natural — if it feels good, go for it.”
“First time I’ve ever been excited to do homework.” she laughed, jumping up as if in a hurry to get up to her room to try out all of the new suggestions. “Thanks so so so much Matty!” She leaned in for another hug, her hair falling over my face and enveloping me with her wonderful scents and softness.
“No prob. Have fun with it!” I managed to choke out.
With all this sex talk, I think I was going to have to do some `homework’ tonight as well! How would I be able to get off without imagining Caylee doing the same thing right down the hall?!
* * * *
Day 4 — Monday:
Caylee seemed a little too shy the next morning to report on whether or not she’d attempted her homework and how it had gone so I let it slide for now. It seemed like our evenings were when we really slipped into teacher and student roles and she allowed her curiosity to overcome her embarrassment.
We enjoyed another afternoon poolside between lunch and dinner. I was in one of my swim trunks and Caylee was in yet another bikini — this one purple. I wouldn’t say I was becoming immune to the sight of her — türkçe bahis it did still cause double-takes when I forgot how… woman-like she had become I guess? But I was getting better at hiding my reactions, pretending like all was normal. I figured I’d fake it ’til I made it and things started feeling normal again.
Once we sat down with our plates for supper, I pulled out a blank notepad paper so that Caylee and I could start making a grocery list. I planned to go shopping soon for the weekend and beyond.
“So I have a favour to ask…” she started, a bit shyly.
“Name it!” I said gregariously, thinking she wanted special cookies or something like that.
“Well, I’m embarrassed to admit this, especially after all your cool party stories, but I’ve actually never tried alcohol. Like at all.”
“Nothing? Like not even wine at special occasions?” I asked.
“Nope. I guess maybe my parents didn’t want me liking it or something?” Another famous Caylee eye roll. “So I was hoping you could get us something when you’re out shopping. Maybe just something with a really low amount of alcohol?”
I let her know I would think about it but didn’t really see the harm if she had a low-alcohol drink with dinner. I had seen the awesome BBQ set up here and had hoped to have a beer or two myself while I tried it out. Didn’t seem fair to expect her to sit out on that.
We had our after-supper movie time again and once the movie was over, Caylee was able to overcome her shyness enough to give me a report on her homework. Unfortunately, she hadn’t had much success.
“Don’t get me wrong, it was great actually knowing what to do for once! I went slowly and step by step. But when I got to… ugh. Can I just look a couple of things up on your laptop?”
“Yah sure.” I told her, passing it over. She typed and clicked for a little while, absorbing all of the information. Finally she looked up at me, blushing.
“OK, might need your help again. You don’t happen to have any…” she looked down at the screen again for a second “…lubricant with you, do you?”
My turn to be a little embarrassed. “Well I can usually get away with lotion — easier to travel with – but that might not work as well for you. Want me to pick up a little bottle of lube at the grocery store when I go? They should have a drugstore supplies section.”
“Would you? That sounds like it would be helpful.”
“In the meantime, you can try using saliva.” I suggested.
“Saliva?” she seemed confused and I realized she was maybe picturing impossible contortions.
I demonstrated by carefully spitting onto my middle finger, showing her the drop that was left clinging.
“Ohh!” she exclaimed and then giggled a bit. “I’ll try that!”
We moved on to other topics but Caylee seemed pretty eager to go try out her new skills and info so we said goodnight and she bounced upstairs ahead of me while I made my closing-up-the-house rounds.
Again, I knew I would be conducting my own experiments once I was in bed. Last night, with Caylee right down the hall doing her `homework’, I had definitely failed in my attempts to block that idea from my own thoughts while I doing the same thing! I guess tonight I would just allow them to pass through my mind — after all, it would only be a fantasy, not real life.
* * * *
Day 8 — Thursday:
It felt a bit strange to be out and about in the ‘burbs after so many days staying at home. Caylee and I had not only created our own little summer routine but it seemed like we had made a little bubble away from the rest of the world as well. We continued our suppers together, our movie nights, our in-depth talks.
I had started to get over the shock of Caylee-as-a-young-woman and had stopped beating myself up for the little flickers of attraction here and there. She was a really cute and sexy girl, of course my body would stand up (literally) and take notice at times! I did try my best to tamp down those thoughts and feelings but it seemed less urgent to do so. She didn’t seem to have noticed anything out of the ordinary with my behaviour and there was no one else to bother me about it. So I felt like we could just continue on as we had been — me, teaching and Caylee, soaking everything up like an eager sponge.
Late that afternoon, I flipped the grilled chicken and tinfoil pouches of veggies on the mega BBQ on güvenilir bahis siteleri the back patio. Yes, I can cook even though I’m a guy, get over it! Usually barbecuing wasn’t so enjoyable — I’m glad I didn’t let the food burn while standing around watching Caylee in the pool. Calling her to come eat and watching her climb the ladder, dripping wet, flipping her long blond hair out of her face was like a dream come true. I was almost prepared for time to go “slow-mo” and a movie soundtrack to start playing!
As we ate, we had our usual relaxed chat session, combined with her many questions about social and relationship stuff. Tonight’s topic seemed to be all about dating… Had I had girlfriends, what was that like, where did we go on dates, how was a girlfriend normally expected to behave.
Once Caylee had some supper in her belly, I surprised her by going inside to get her a cooler.
“Here ya go, your very first taste of booze.” I also held a beer for myself.
“Yay! You’re the best, Matt!” she cried, bouncing up and down in her seat and reaching for the bottle.
I pulled it back just out of her reach with a whole bunch of warnings and cautions. I told her she should always respect her own limits, never get smashed (especially around people she didn’t completely trust) or put herself in unsafe situations, yada yada. I could tell she was trying really hard not to roll her eyes at me so I eventually passed it over.
She took a cautious sip. “It’s yummy!” she said, sound surprised.
“Well just be glad I didn’t get you a beer. That was the other low-alcohol choice but I thought you’d like this better.”
“Yah, your beer smells pretty gross, no offence.”
“None taken, it’s an acquired taste.” I said in a snobby wine-taster voice, which had her giggling.
For our usual movie night, Caylee convinced me to get in my “PJs” too, which was just a pair of boxers and a T-shirt. We sprawled out on the huge family room sectional together in what had become our regular spots — each in a corner of the 4-seat couch with large ottoman-type sections for our feet to stretch out on, pointed towards the TV. Sometimes she would turn on her side and lay down facing the TV, her cute little feet almost reaching my hip.
“This has been a really great week.” she said quietly once the credits were rolling. She’d been a little more subdued tonight, asking me less questions during the movie. I told her I was really glad she’d been enjoying herself. “A few of my girl friends want to come over on the weekend but I feel like I want to keep you all to myself.” she joked.
“Up to you… I’m happy to meet your friends. But yah, I was thinking today about how weird it felt to be out of the house. It feels like we’ve kinda made our own little world here, with a nice routine.”
“Yes that’s it exactly. Our own little bubble…” she mused, echoing my earlier thoughts exactly. “Well, my friends can wait. I see them all year. Besides, they’re mostly busy with their boyfriends anyways and they often don’t want to come over here since the guys aren’t allowed to come along. Still haven’t changed your mind on that rule eh?” she asked with a sideways glance and a sly smile.
“Nope, sorry. Like I said, happy to find loopholes, but I gotta do my job. It’s been a lot more fun that I thought it would be though so thanks for that. I’m glad you’re not the kid I remember!” I joked.
She rolled her eyes — at her past self this time, I was sure. “Yah, I’ve certainly matured a lot since then. And am maturing even more this summer! I have already learned so much.”
“Well then I guess we’ll call this little gift a reward for being such a good student!” I teased, pulling the little bottle of lube out from where I’d stashed it.
“Yay!” she exclaimed. “This is great, I can’t wait to try it. Thank you so so much. I would have been way to embarrassed to buy something like this. Even if I had known what it was before this week!”
“You’re very welcome and I hope you find it helpful. Sorry the past few days haven’t been working for you.” When Caylee had first reported that the saliva trick wasn’t cutting it for her, I tried to encourage her to “dip into her own well” so to speak but I guess she wasn’t getting wet enough?
She may have too much of a mental block if that was the case. We’d see how this went and work through one problem at a time. I was committed to helping make sure she had as positive an experience with all of this as possible to help undo some of the damage of her upbringing and develop a more positive and healthy attitude towards her own body and her sexuality.
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