When I woke up the next morning, I first had to recall where I was and how I had ended up there. The environment seemed familiar, yet unusual. That was until I vaguely remembered I was lying on the living room couch—alone. Drowsy as I was I tossed and turned a bit until my face came to rest on Emily's pillow. Unconsciously, I hugged the pillow and dug my nose into it to catch her smell which set just a few butterflies in my belly free.
"Jackson," I heard her say, making me jump and throw her pillow to the floor in a ridiculous attempt to hide what I was doing. Fortunately, her voice came from the kitchen, sparing me the awkward explanation. "Breakfast is ready, sleepyhead. Don't make me pull you off the couch by your leg, you hear me?"
Wondering what there was to prepare with that breakfast, I stumbled to the kitchen. A bowl of cereal and a glass of juice. Big deal. Unless that aroma that came to my nose was actual coffee? And freshly fried pancakes? All that trouble despite the scene I had made her?
"Finally you're awake," Emily said, letting the last pancake jump out of the pan and turn in midair. "I was afraid I'd have to beat your lazy ass off the couch." She turned away from the stove and smiled at me. "Pleasant dreams tonight?" She held the scoop to her chin, rolled her eyes playfully, bit her lip and added, "Dreams of me, maybe? I hope so since you had your hand in your boxers when I woke up."
My heart pounded up my throat and my eyes widened in horror. My inner child wanted to storm off, retire to my room and spend the rest of the day in fetal position, ashamed of my unflattering actions while asleep.
A few seconds later, Emily burst out laughing. "Oh, you should see yourself right now. That face. Priceless!"
Oh boy, that was... I could feel the adrenaline letting my ears heat up and hear the blood pulsing through their veins.
I managed a crooked grin as my mind came up with a comeback, “You know, I had to put my junk back in order after you touched me in your sleep.” Okay, it wasn't the best comeback. I was still a beginner, alright?
“Look who's mister bold all of a sudden,” Emily exclaimed, lifting one eyebrow. “Nice one.”
She motioned me to sit at the table where two piles of pancakes were waiting to be devoured.
“Your mother said we'd have to finish what's in the fridge before it gets bad. There were a couple eggs. So I thought we might just as well have pancakes. I hope you'll like them?”
“Wow,” I managed, then said, “That's, like, awesome! You went through all that trouble for me?”
With her free hand, she played with a strand of her hair when she explained, “I felt like I had kicked you in the teeth a bit yesterday with all that girl stuff. That's just my way to apologize. I hope you can forgive me.”
“Whoa, Emily. That wasn't necessary, really,” I began, chuckled a bit bashfully, and went on, “but... but... Look, it's not like, uh... I started yelling at you. If anyone has to apologize, it's me. You're so nice to me and I'm having such a great time with you—I really like having you around, I swear—and I just yelled at you out of a childish caprice. And you just... just make pancakes?”
“Aw, that's so sweet, Jackson,” she said and planted a quick kiss on my cheek, feeding the butterflies from earlier on the couch.
While eating, we discussed our schedule of the day.
“So what's the plan today? Same as yesterday? All work and no play in the morning and slouching in the afternoon?” asked Emily. “I wanna try that bikini you helped me buy yesterday and there's just that perfect place I told you about.”
“Yeah, about that...” I began, hearing my voice fail.
“C'mon, Jackson, don't be a party pooper,” she replied.
“I have, uh, a little something over lunch and, uh, I just don't know yet...” I paused, looking for words to continue beating around the bush out of fear. Fear for what? To get Emily jealous? It was just as pathetic as it sounds. “...how long it, uh, will take, you know, and, uh—”
“Jackson,” she cut me short like an inquisitive mother. “Will you fill me in with your plans? I'm your (marking the quotation marks with her fingers) 'babysitter', remember?”
“I, uh...” I tried, yet failed.
Emily's eyes lit up in delight. “You're having a date, aren't you? Who's the lucky girl?”
I lowered my face and awkwardly looked onto my plate in which the last crumbs of pancake were swimming in a pool of Aunt Jemima's.
“Yeah,” I mouthed. I was fighting my teenage anxiety to utter any more words with a thin voice. “Her name is Sarah. She's from my class.”
“And what's there to be ashamed of?” Emily asked in her most understanding tone. “It's not like you're so bad with girls, is it? I mean, you made a pretty good impression on me so far.”
I barely managed to look her in the eyes. “With you, sure, but you're cool, easy, comfortable and, like, way out of my league. Of course, I can talk to you easily because I know it'll never happen.”
“Out of whose league? Yours?” Emily rephrased. “Although I get to spend the entire week with you, you should know that I'm insanely jealous of Sarah right now. I would date you just the same if only you weren't a bit older, Jackson.”
“You're just saying this to make me feel better,” I countered with more confidence although her putting me back to place by reminding me of my age stung a bit, “but guess what, it's working. I really do feel better. Your flattery does wonders to my self-esteem. Thank you.”
My ego still boosted by Emily's motivational words after a crunching three-hour session of trigonometry, I took my bicycle and rushed to the mall shortly before noon. Radiant with overconfidence, I chained my bike to the bicycle stand and stepped to the main entrance with my head held high. Full of verve, I decided to discard any thought about a possible rejection as I felt it would surely be a buzzkill to a degree of confidence I wasn't used to having. I'd worry about this if it were to happen, I thought.
An hour later and pissed off big time, I returned home from my date with Sarah a lot earlier than expected and I found Emily lying in an easy chair in our garden. She looked asleep but I couldn't tell since she was wearing her shades. Her book was open on her belly she didn't react when I approached her. Despite my frustration, my perverted teenage mind insisted on trying to sneak an unnoticed peek of her. I almost let out a yell in shock when I realized she had gone topless and her peach-sized breasts were lazily resting on her chest. I swallowed hard and tiptoed back into the house, trying to make as little noise as possible.
Once inside, I turned on the TV and the Switch and tried to blow off some steam by going on a rampage on Fortnite. I couldn't concentrate as my mind was still preoccupied by my failed date with Sarah and lost a few rounds way too easily. I uttered a never-ending stream of curses and, finally, in rage quit the game before I could vent my aggression on anything I might regret.
That was when I noticed Emily was standing beside me dressed in just her loose pajama shirt.
“I heard a noise and came to check on you,” she explained. “Why are you home so early? You alright, kiddo?”
“No,” I yelled, tears swelling in my eyes.
“Friendzoned again?” she asked.
I only managed a nod before she knelt down on the couch beside me, wrapped her arms around me and pressed me against her chest. I sobbed a few times and was surprised to find my loins, in this situation, still found it highly exciting to feel a set of bra-less boobs against my face. What kind of sick mind... Oh, I forgot. Teenage hormones.
“Poor baby,” she whispered while running her hands through my hair and over my back.
“I'm sorry,” I sniffled. “I'm getting my snot all over your shirt.”
With her softest voice, she replied, “Don't worry about that. Nothing that can't be washed out again. We got some more important stuff to deal with. Like that Sarah girl. She doesn't know what she's missing.”
Did she really just use that stale line from 'Teenage Dirtbag'?
“She told me she was gonna meet her boyfriend after lunch. She just said it casually like nothing. I know she doesn't have a boyfriend. She just lied to my face and said I was a good friend for inviting her for lunch.” I took a deep, heavy breath and add a spiteful “Bitch!”
“That's really mean,” Emily commented when she loosened the embrace and looked at me. “At least now you know she's a lying cow who doesn't deserve you.”
“Well, thank you. It still hurts like hell to get rejected like that,” I nagged before I backpedaled a bit, “Sorry. That was inappropriate. You're just trying to be nice here and I'm still bitching around.”
“Know what, Jackson,” Emily said, letting go of me and beaming at me with her heartwarming smile. “Let's just give you a change of ideas, okay? Let's just go and have a dip at the river. And, uh, it was supposed to be a surprise, but since I promised to teach you how to talk to girls, I'll take you to a party tonight. My year organized a farewell party for the seniors who are gonna leave for college and you're gonna be my plus one. Plenty of girls to talk to and practice your flirting skills. Watcha say?”
I afforded a crooked smile through my tear-stained face. I sniffed back my snot like a real Don Juan and nodded.
“Yeah, I'd like that,” I said, staring blankly at the wall, then, looking at her again, added, “Thank you for being so nice, Emily.”
“Don't sweat it. I'm just doing my job as a babysitter.”
Ouch, that one did hurt my male pride. Well, she was three years my senior, wasn't she? I snuffled my nose, trying to hide my hurt ego and gave her my best smile given the circumstances.
She told me to hurry and get changed into my swimming trunks.
The place she took me to was about twenty minutes away by bicycle. We left town to the nearby forest and after a few minutes, we were already following the river upstream on the forest track. After a sharp left turn, we got off our bikes, tied them together and entered the denser parts of the forest off the road.
Emily led the way through thorn bush and stinging-nettles. Although not really far from the established trails, it was understandable why only few people ventured to the place she wanted to take me to. I was almost at the point of going on a full-scale whiny teenage lament about the stupid forest when, suddenly, we entered a clearing next to a natural waterfall. The sudden impressions were overwhelming: the roaring of the water, the lush greenery of the forest, the bird and insect sounds—this tiny spot on earth could have easily passed for the Garden of Eden.
The water basin the fall had carved was deep enough to jump from the top and a thick branch hung from a rope like a liana to which a piece of driftwood had been attached.
“Wow,” I aspirated. “This place is amazing. How did you find this?”
“My brother showed it to me,” was her answer. “We used to come here a lot in Summer before he left for Princeton—and we still did the last couple times he came home over nonterm. It was him who installed the makeshift swing. This year, he's not gonna make it and I really wanted to go, but not alone.”
She beamed from seeing my amazement over her secret hideout. I smiled back.
“So, you know, I thought, maybe I could take you here,” she resumed. “Glad to see you like it. Just promise me something, Jackson. This place is special. It has to stay special. Please don't show it to anyone, alright?”
“Yeah? Can do, I suppose,” I hesitatingly commented, not being sure what she meant by that. Why was she showing me—me, the little brat she was babysitting—her secret hideout? Why not some hung stud who would properly screw her brains out. Or did she plan to...? No way! Yeah, she had said something about giving me a change of ideas, but this? No way! No way she would profane her sacred sanctuary just like that; least of all with me. Why was I even having thoughts like that? Wasn't I supposed to be mourning another failed date? Great, and now my wiener was sporting a semi. Great timing for utopian wishes!
“Hey, don't just stare into space, kiddo,” I heard Emily shout. She was already halfway in the water, her clothes in an unorderly heap on a patch of grass. “Stop dreaming and come into the water, it's perfect!”
Swallowing hard from seeing her standing in the water in the bikini she had bought the day before, I undressed too. Seeing how easily she had stepped in, I underestimated the cold of the water but decided to give my best shot at displaying my virility. This, nevertheless, posed great difficulty as once the water touched my butt cheeks and caressed my balls, the latter shrunk to the size of M&M's, seeking the warmth of my body. I felt my dick shrivel up to a ridiculous stub. Still, determined to make proof of my manliness, I inched my way further, giving my best facial expression of the male badass I was—or so I thought at least. Just the pair of Ray-Bans and a set of crossed scrawny arms and give that ladies' man some space, bitches—oh yeah!
“You're making the funniest faces, Jackson,” Emily laughed. “You don't have to rush it, you know. We've got the whole afternoon. Take your time if it's too cold for you. It's not embarrassing.”
Busted! Still, I kept making a fool of myself trying to act strong. Teenagers... sigh...
Emily was now holding her belly. “You're just too funny, kiddo, for real.” Her laughter gave way to a devilish smirk. “Alright, since you keep insisting on it, here's your punishment.”
She splashed water against me which made me shriek like a little girl but had the desired effect. Not scared of the cold water anymore, I practically jumped on top of her to dunk her into the water. Having anticipated my attack, she stepped aside and used my own momentum to dunk me underwater instead. I surged and tried to retaliate but she was quicker again and managed her way behind me.
She wrapped her arms around me, pressed her breasts against my back and, while her hands were running down my belly to the waistband of my trunks, leaned in to whisper, “Sure you're not here for something... other than wrestling with me?”
My mind went completely blank. I wanted to stammer something incomprehensible when she pushed me forward to fall into the water again, my guard down, obviously.
“Oh my, you fell for the oldest trick,” she snickered.
“Just you wait,” I replied in a playfully challenged tone, dashing at her.
We kept wrestling for a while, laughing, pushing, touching each other without any shame however bold our touches were. I was completely absorbed by the fun we were having until I felt a stinging itch on my forearm. I checked to find a colossal horsefly pleasurably sucking my blood.
Startled, I swatted the living shit out of that thing only to find it flying away and land on Emily's butt were it resumed its meal on her blood instead. With no inhibitions whatsoever, I slapped her butt, making her squeal and almost jump. This time, kept my hand firmly locked to her skin so the insect couldn't escape a second time in the case it still hadn't died. I felt it twitch under my palm, so, still without thinking any further, I groped Emily's butt to clench my fist around the horsefly. She gasped in response to my unmannerly touch.
“Jackson,” she aspirated, her cheeks flushed and her breathing getting unsteady.
Only then it dawned to me I had smacked her ass—not only that but also groped her boldly. My jaw began to tremble at the realization of my discourteousness approaching.
Fully expecting a full-blown slap to my cheek, I gasped, “Emily, I—”
She cut me short by tugging me into a deep, intimate embrace. The feeling of her breasts clad in her wet bikini top against my chest had my cock swell to its full glory withing a few labored breaths. Please don't feel it! Please don't feel it! Sure, she's not gonna feel it when it's almost pressing into her belly button, duh! With one hand, she pulled me in closer while her other wandered down to the small of my back and let two fingertips disappear into the waistband of my trunks. I felt her hips squirm just very slightly against my erect prick and thought I heard her in- and exhale into my ear shakily. Overwhelmed by my teenage anxiety, I had millions of questions and what-ifs running through my head which made my whole body turn into an immovable pillar of salt.
When Emily let go of me, she kept her arms loosely around my neck. She bit her bottom lip when she looked at me.
With her cheeks flaming red and almost moaning, she said, “Jackson... Thank you.”
She smiled softly at me with her eyes half-closed in what I interpreted as pleasure.
The sudden stinging pain in my hand broke the intimacy and made me wince. As I opened my hand in reaction, the unscathed horsefly casually flew away and escaped.
“These things just won't die,” I expressed my astonishment. “So much for Garden Eden.”
We decided to get back and to skip getting dressed and head back home in our swimming gear. On the way back to fetch our bicycles, I was surprised when Emily took me by my hand and lead the way out. Her skin felt soft and warm, her touch light while my brain was still trying to process my first one-on-one experience with a girl.
Once back home, I excused myself and rushed to my bedroom. I told Emily I dearly needed a nap if I wanted to be able to enjoy the party that night—and to be in shape for the flirting. She replied she needed a quick rest too and suggested we have pizza ordered for dinner. I agreed to have it delivered at seven.
Still in my swimming trunks, I fell into my bed but, despite being spent, I tossed and turned with a mind still filled with the events of the day: Sarah, the failed date, the river, Emily, Emily in her bikini, Emily wrestling with me, Emily and her luscious ass, Emily... Eventually, I managed to get some sleep, yet my dreams were still filled with images of that alluring vixen.
When I woke up again, I didn't feel rested, really. At least, I thought, Emily had kept her promise and gotten my mind off that stupid Sarah—and filled it with lewd pictures of her humble self, that is. Given the situation, I decided to make the best out of it and finally give in to the urge I had felt since laying eyes upon this smoking beauty: just beat it! A quick wank while lying on my back had to do for I had my phone in my trousers and the latter were still in the backpack downstairs. Therefore, I had no indication to what time it was.
My best guess was that my dick had been standing straight like a capital 'I' through my entire nap from the way the erection painfully begged for attention. At least this saved me the work of getting it up, yay!
I didn't have to look far for proper one-handed reading material since the sight of Emily in her skimpy swimming garments was still fresh and deeply carved into my mind. Hooray for teenage memorizing ability! Without realizing it, I started moaning her name into the emptiness of my room.
From the moment I gripped my shaft, I felt the first familiar twitching in my helmet, which signaled the impending release. After merely a few quick strokes, I started thrusting my hips against my clenched fist. I kept gasping my babysitter's name as my orgasm approached quickly—and also as my bedroom door flung open and the girl whose name I kept shamelessly pronouncing while doing my dirty teenage deed stepped in.
“Oh my god, Jackson,” was what I needed to hear before realizing she stood there, her eyes following the trajectory of my first splash of semen onto my belly.
My eyes sprang open in shock as I tried to conceal my spritzing boner, only to have the blanket smear my spunk all over my torso rather than effectively covering my misdoing before it fell to the ground, leaving my glory in full view. Ashamed of my actions, my gaze was transfixed to hers. I couldn't flinch, let alone blink.
“E-E-Emil... Emily” was all I managed to stammer before I fell silent for two seconds and heard her swallow.
She whispered an apology, turned around and rushed downstairs.
Not even wondering about why she had come to my room without knocking in the first place, I sloppily wiped the cum stains off my torso, grabbed the first pair of shorts I found and a crumpled t-shirt and followed her. Racing down the stairs in pursuit of Emily, the swinging of the remaining semi in my pants painfully reminded me why I wasn't the greatest fan of freeballing.
As if getting caught in the act hadn't already been clichéd enough, before I reached the end of the staircase, Emily popped up out of nowhere at the base of the stairs. Unable to swerve past her anymore, I tripped and landed on her. With sheer luck, neither of us hit anything while falling. Still, my face landed right between her soft breasts.
When I lifted my head and wanted to ask her if she was alright, my inquiry kept stuck in my throat as my eyes fell on her flushed face and I could hear her panting. I felt my heart pounding in my throat, the blood filling my ears and cheeks and my stomach churn as her arms pulled me into an unexpected embrace. I tried to crawl forward to have my face above hers. The tension was so thick, the soaring bloodstream in my ears was almost deafening. I desperately wanted to apologize but my trembling jaw wouldn't allow a single word to escape my lips. Instead, her pull drew me closer to her until I felt the breeze of her breath on my lips which parted from alone.
The doorbell rang. Yes, yet another cliché. Don't ask. Couldn't make that up if I wanted to!
My face red hot, I made it back up on my feet. I stepped to the door with my mind unable to form any sensible thought.
“What!” I hissed when I jerked the door open to find the pizza delivery guy.
“Your pizza, dude,” he shot back, obviously displeased by my demeanor. “That'll be eighteen bucks fifty—and a personality check for free if you're interested.”
I awkwardly handed the poor bastard his money plus a tip, accepted the pizza, apologized bashfully and turned around to face Emily who was standing there with her arms crossed. I almost dropped our dinner. She was pressing her lips together and gave me that infamous 'white people smile' before she turned around and went to the kitchen.
Hesitantly, I followed her, not sure what to expect, yet damn sure it would make our so far very pleasant holidays together go south big time. I cursed myself for jacking off so incautiously. What had I been thinking? Oh yeah, I remember: nothing! Just point-blank teenage levity. A couple hormones here, some teen anxiety there, a dash of stupidity, a twist of inexperience, some ice cubes, shaken, not stirred (stay classy, right?)... et voilà: desperate virgin on the rocks! Ugh!
In the kitchen, Emily was leaning against the counter, her arms still crossed. “Jackson, we need to talk.”
Here we go! In my thoughts, I rolled my eyes and braced myself for a sermon on my conduct much worse than the pizza delivery guy just two minutes prior. Now I was to have even girls my age—practically my age—give me lessons about conduct. Well done, dude, well done. Real Casanova! Thunderous applause! I opened the pizza box with a cheesy smile and presented her its contents. As if that helped any.
We took a generous bite of pizza each before she spoke, “Look, don't get me wrong. I just wanna talk, nothing more.” She let the words sink in. “First, I'm not mad at you, okay?” Major relief! “Second, I'm sorry for just waltzing into your room like that.”
Leaning against the opposite kitchen counter, I gulped down my hardly-chewed mouthful. “Uh, I don't really know what to say. I'm sorry... I, uh, guess? Yes, I really am. I didn't mean you to, well, find me in this unflattering position. If you're grossed out, go ahead. Say it. I deserve all disgust you feel towards me, and—”
“Jackson, please,” she interrupted me. “I'm not grossed out at all. Look, it's just natural. For you, for me, for your parents, most probably.” Yeah, thanks for the pictures. Her cheeks blushed slightly when she resumed, “I do it all the time too. And it's no wonder. You're sixteen—in the middle of your hormonal rage. Also, I was teasing you big time. No wonder you go crazy about it. You have my full understanding.”
“Wow, thanks for your honesty,” I mumbled, avoiding her gaze in my little shame. “But that doesn't make me, uh, yeah, saying... your... you know... any better.”
I so wished the ground would open up and swallow me. I was mortified.
I could see that she too was struggling with expressing her feelings. My best guess, still, was that she was preparing to either kill me right away, torture me to a slow, agonizing death or, at the very least, turn the next two weeks or so of my life to living hell. She tried to hide her face behind the next slice of her pizza. The color of her cheeks indeed would have given a great camo in an Italian Sugo factory.
“Actually, Jackson, it...” She avoided my gaze and bit her bottom lip. “I found it kinda, like, flattering when, you know, when I heard you moaning my name. I know it sounds weird and creepy, but it kinda flatters me to know you jerk off to me.”
Come again?
“Also, you're pretty, uh...” she swallowed audibly. “Big.”
Now that was a far cry from what I had been expecting. I quickly shoved almost an entire piece of pizza down my throat and gulped that thing down almost in one piece. I didn't know what to say or how to react. Was that a compliment?
“See, I can be creepy too,” she stated, a shy smile on her lips.
I hammered down my glass of coke and let out a shameless burp, making her giggle.
“Sorry, I just needed that,” I explained myself. “Feel much better now.”
Emily smiled at me, grabbed both my wrists and pulled me close to plant a peck on my cheek. She let go of me and I placed my hand on where she had kissed me. Her radiant smile caused a warmth in my belly and a lightness in my heart. I looked her straight in the eyes that were beaming with life.
“Thank you for breaking the awkwardness,” she began. “You really are a golden boy. What am I saying? You're a truly desirable young man. If only you were a bit older...” She ran her hand through my hair. “But now let's get ourselves ready. Can I have a look at your wardrobe?”
I agreed to whatever there was to get ready for. She looked stunning just the way she was but she wouldn't hear it without telling me I should stop and how cute and stupid I was. As much as I liked seeing her lively expression and hearing her angelic voice, I didn't understand why she insisted on browsing my wardrobe too. Just like Mom, I thought until I saw what she was picking for me.