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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…
* * * *
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 canlı bahis 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!
Just the thought of how she had licked every drop of cum from my chest, neck, and face still made me shudder with residual arousal – that was probably the hottest thing I’d ever experienced in my life. And then we’d also kissed… God, what would I do with the absolute tsunami of guilt if anything else happened? Just thinking about the whole situation made my head spin. And as I pulled myself from my sexy reminiscing, I discovered my erection had returned. Well, crap.
“I don’t know, Caylee. Let’s see how things go. You’re a little too irresistible.” I said with a wry smile, shifting a little awkwardly under her soft, warm touch. Now that Caylee had become aware of her allure as a gorgeous young woman, she had begun to learn how to leverage that allure.
“Good.” she said smugly. “I don’t want you to resist me.” She quickly swung a leg over my waist so that before I could even blink, she was bahis siteleri straddling me, her gaze penetrating and serious. Her hands had come up to hold my jaw, and she immediately became interested in my stubble, scraping her hands along my cheeks.
“Clearly!” I tried my best to sound disapproving and keep my cool, at least outwardly. Internally, my heart rate had picked up speed and my morning wood had becoming morning steel. My hands went to her waist again, but she seemed to suspect that I would try to hoist her off my lap and came prepared. Tangling her hands in my hair, Caylee came in for the kill, her body plastering itself against mine. She wasn’t heavy but she wasn’t a tiny little thing either, and she had fit muscles from her time in the pool. She used her weight to press into me and the muscles of her thighs to squeeze the outside of mine. Her head tilted to meet my lips at the perfect angle. But she didn’t kiss me; her lips remained just barely touching mine.
“Matt…” she whispered against me, the feel of her warm breath in my mouth making me shudder. “What happened to that lock box your brain constructed itself for the guilt, hmm?” I was only able to groan, my hands clenching on her sides, bunching the fabric of her cute little pyjama top, tortured by the knowledge I now had of exactly how soft her skin would be underneath it. “I know you want this.” She adjusted her hips so that my erection was perfectly nestled between her legs; I could feel her heat even through the material of both our PJ shorts. I found myself wondering how wet she would be and bit back a moan as she continued her seductive whispers. “I can tell. And last night was so so great.” I couldn’t argue with her there – it had been absolutely amazing. She sat back a little, still on my lap but giving me a little breathing room to speak.
“You’re right. Sorry I’m so in my head this morning.” I told her, my mood still serious, even as I delighted in the feel of her pressed against me and wanted her back as close as she’d been a moment ago. I was consciously using every bit of my willpower to fight the urge to flip her over, rip our PJs off, and thrust into her right then and there!
“We both seem to have that problem eh?” she replied, reminding me of why she’d had such a hard time getting herself off every single time she’d tried. Until last night; those negative messages had kept tripping her up. She had her own mental demons but they weren’t the same as mine – she didn’t seem to feel at all guilty about anything we did together. “Something to work on. Just keep reminding yourself that you aren’t corrupting me. You’re helping me. I want this. I want you.”
And with that, she pulled me out of my thoughts completely by coming back firmly against me and meeting my lips with her own. Despite still being an inexperienced kisser, Caylee more than made up for that with her enthusiasm. She opened her mouth and I responded in kind, allowing our tongues to play in each other’s mouths. She kept one hand in my hair, massaging my scalp and occasionally smoothing it back before messing it up again. The other hand explored my chest, arms and shoulders. My hands started to explore under the fabric of her top, feeling her wonderfully soft skin, feathering across the curvy dip of her waist into the flare of her hips. She felt so good it was like finally drinking water after days in the desert.
“God Caylee, you make me forget this is wrong.” I growled at her, unable to resist pulling her into me with my hold on her hips. She responded with a moan, enjoying the friction by rocking into me again.
“Well, don’t forget completely.” she murmured in between kisses. “That’s part of why it’s so hot.”
“I hate that you’re right.” I groaned. Keeping my hands underneath the fabric of her top, I caressed her back, pressing her body more firmly against me at the same time. So soft! I traced the edges of her breasts, naked under her light summer PJ top.
“Matty, please, don’t stop touching me, I need it so much.” she pleaded, continuing to wiggle in my lap, pressing her warmth against my very hard dick again and again.
I tried to call back my summer lock-box, to block out the remaining little nudges of shame that had been shoved to the very edges as lust filled my mind. I let go of all my hesitations, untangled myself from my churning thoughts, and just allowed myself to respond to Caylee as a lover. I pushed the last of my niggling doubts aside for another time and focused only on Caylee’s deliciously fresh skin.
“OK baby, whatever you need.” My words confirmed I was giving myself up to her desires, I was surrendering. I moved my hands, always connected to her skin, and cupped her breasts from underneath, my thumbs coming up to touch her nipples.
“Oh God, so good… that feels so different than when I do that!” she observed.
“Different better?” I teased her, continuing to stroke and tease them.
“Uh huh” she gasped. She grabbed her PJ top and pulled it over her head to give me better access so I leaned forward to use my tongue. Her breasts were exquisite – so perfectly round and bahis şirketleri perky, with pink areolae and small nubby nipples a shade or two darker. No freckles beyond the clearly marked tan lines of her swimsuits and bikinis, just creamy pale skin.
She was very responsive to having her nipples bathed with my tongue, wiggling so much in my lap that I had to band my arms around her back to hold her breasts to my mouth. I licked all around them, then attended to her collarbone and neck. I gently pulled each nipple into my mouth with a light suction.
It didn’t take her long to go completely wild with arousal. As I continued my ministrations, she got more desperate and out of breath, tilting her hips to rub against me repeatedly. I was worried she may come just like that! There was so much more I wanted her to experience and enjoy.
Encouraging her to wrap her legs around my waist, I scooped her butt with my hands. She understood my intentions when I started to shift my legs over my side of the bed and she held on tight. Once I was standing, with her legs wrapped around my waist and arms holding around my neck, I walked to the bottom of the bed and turned around to gently lay her on her back, kneeling on the bed first in order to prevent her legs from dangling off the end.
From my position in between her parted legs, I ran my hands from her feet to her thighs and back again. She closed her eyes and moaned, still unable to fight her urges to wiggle and move. She was clearly missing the friction her pussy had experienced rubbing up against my dick, even with her pyjama shorts and my boxer shorts in between.
And now her little shorts had to go… On my next pass up her legs, I slipped my hands under the elastic of the cute little ruffles at the bottom to stroke her upper thighs. But I still stroked back down as I had been doing. A few more times, a little higher each time, and then on the next trip up, I stayed outside her shorts and travelled up her hips. Grabbing the elastic waistband, I brought them slowly back down with me, all the way to her feet and then off. I continued up one last time, very slowly, letting the anticipation build for her. She was finally still for a moment, meeting my eyes, her mouth a perfect little “o” of surprised arousal. I could see in her eyes that it was a struggle for her not to move.
Enjoying the sight of her naked for the first time, my hands skimmed over her thighs many more times. My gaze roamed from her wide blue eyes, parted lips, to her chest heaving with deep breaths before continuing down to enjoy the sight of her soft belly, noticeably indented waist and gorgeous curvy hips. I played my fingers over her strong legs, massaging the firm muscles. Reaching up to caress her arms as well, I noticed the fine pale hairs, barely visible. Her nipples were still wet from my lips and tongue, and I lightly touched them with gentle brushes of my fingertips. “Wow, Caylee. You’re so unbelievably beautiful…”
“Thanks.” she whispered in reply. She wasn’t returning to her shy ways again, just having trouble forming sentences it seemed. I continued my reverent observation of her perfection, keeping my touch feathery light. “Matt…” she pleaded, squirming again. I knew what she was impatient for.
Finally, making a few more trips up and down her long legs, I allowed my hands to meet at her pussy lips. I spread her folds open and looked my fill at the beautiful fresh pinkness there, shiny with the juices of her arousal. I took a deep breath to take in her scent. “…and you smell delicious.” Even now, almost drooling with eagerness to taste her, I remembered to continue my campaign of encouraging Caylee to have sexual confidence. I wanted to show her how very much I meant what I’d said last night about loving to go down on women, not just out of obligation but because I craved that sweet taste, their soft cries, those shuddering climaxes.
“Oh please…” she whispered excitedly, her hands gently playing with my hair, almost to the point of pulling my head down but not quite allowing herself to be that bold.
“Mmm, I can’t wait to taste you…” I murmured. She gasped and pushed one of her heels down into the mattress, fidgeting against my hands in her eagerness to have my mouth on her.
Keeping eye contact with Caylee, I bent my head down and had my first lick of her sweetness, a small lap of her clit with a flat tongue. She was just as delicious as I’d imagined and we groaned together. I went back again and again, laying down flat, my hands still holding those soft lips apart while my arms and elbows kept her legs wide open for me. I alternated licking at her tiny little clit and shoving my tongue up her pussy as far as I could go. Based on her responses, it didn’t seem like my tongue was achieving much internally so I slowly inserted a finger while I focused on providing external stimulation with my tongue. I varied my speed and motions – round and round, up and down, and sometimes really quickly side to side, shaking my head. Sometimes I hummed to give her a sensation of vibration, sometimes I would try to suck on her clit. She loved that especially, gripping my hair tightly and crying out, but I backed off when she seemed to be getting too close, licking everywhere except her clitoris, slowly massaging her pussy’s petals with my tongue.
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