The Babysitter I: Reunion free porn video

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“But, Mooommm,” the way I stressed the last 'm', the tone came out a lot whinier than I had intended. “I don't need a babysitter. I'm sixteen!”

We were standing in the doorway, my parents ready to leave.

“Our point exactly,” she shot back routinely. Dad was standing next to her, his suitcase in hand, hardly able to hide his knowing, devilish sneer. “We're gone for two weeks for some quality couple time and you need someone to take care of you.”

“Why? I'm perfectly able to take care of myself,” now that sounded a lot worse than my last expression of discontent, I have to admit, thus failing to prove my point of being an oh-so mature teenager.

Dad tried to cover his major laughing fit by an obnoxious cough. He so pissed me off with his attitude of not taking me seriously. Not that there was much to take seriously, but still...

“Yes, you proved that very well on that Easter weekend when Biff and you basically thrashed our living room. Wherever that boy got the booze from...” she reminded me of that minor mishap.

Okay, it might not have been exactly favorable that they found both of us passed out drunk, practically lying in our own puke. ...and the two joint butts lying in a pile of their ashes in great-grandma's porcelain saucer didn't really help either. I considered myself lucky Mom hadn't mentioned that one.

“Oh, I almost forgot about the weed.” There we go! She theatrically snuffled her nose before adding, “You know full well how much effort you had to put into us trusting you enough not to take you with us on that 'boring' vacation of ours. We had ourselves a deal, remember? You get to stay home for vacation and if we don't notice anything—c'mon, we know teenage boys—we don't send you to summer school. And we see it fit to have you under some competent observation so we asked Emily if she wants to babysit you. You remember her, don't you?”

The horror! Oh, the horror! Indeed Emily had babysat me a couple of times a few years earlier. Last time when I was, like, eleven or twelve. All I remember was a bossy, snot-nosed, ugly duckling of a fourteen-year-old. A real bitch of an oh-so mature teenager. Sounds awfully familiar, except for the age, maybe, doesn't it? Now, in which universe is it fine to have a fourteen-year-old babysit a pre-teen kid and then claim, when said kid is sixteen, he still needs to be babysat? In my book, that didn't add up.

Despite his rather mediocre efforts at hiding it, Dad was loving every second of the moment. How I hated him for this!

“Yes, her. She's gonna go to college. You know her family is not exactly wealthy and they need every financial support they can get. I also promised her a little extra if she tutors you a little bit which you will dearly need if you want to get into a decent college too. She's got all the premises for ivy league, you know? Would be a waste of talent and we don't want her to suffer from crippling debt once she graduated, do we?”

Oh dear lord, now she had to be a grind too? Most likely a know-it-all? So I was facing two perfect weeks of good ol' Fornite and Zelda all to myself completely ruined. If that was your plan to get revenge on me, well done. Thanks, Mom!

I was fuming with anger and about to ridicule myself with a full-scale teenage oral outburst. So much for being old enough to be taken seriously. What prevented me from having my parents reconsider leaving me behind was my mother who opened the door upon three firm knocks.

“On time like clockwork,” she said with almost sarcastic contentment as she opened the door. “Welcome, Emily. You've met the little rascal.” Then, turning to me, “Be nice and say hello.”

I was close to proving Mom's 'little rascal' point with yet another outbreak of most amusing juvenile immaturity when my eyes nearly popped out the moment I lay them on nothing short of a playboy's centerfold. That babe was smoking! All I can say is, 'watch out who you call ugly in middle school.' Oh, the wonders done to the female body by teenage hormones... They had sure done their deed on her, wheeze!

Mouth agape, brain completely blank, I ogled her shamelessly until Mom cleared her throat demonstratively enough for me to grasp my oblivious faux pas and shake me from zombie mode.

A cracking “Hi” was all that came out. Mom rolled her eyes, shaking her head while Dad now bit his free hand trying to prevent more than an amused snicker. Emily just beamed at me and offered me her hand only to pull me into a hug. She held me tightly and ran her hand through my short hair as if I was her kid brother. Given I was a good half-foot taller, it was a rather Kafkaesque situation. To add to the absurdity, my face turned beetroot red from both female closeness and having her put me to my place. Finally, both my parents caught a laughing fit and judging from Emily's grin, she too was well involved in their little, self-satisfied entertainment scheme. Screw you, guys. Seriously!

When they finally left, I felt much better, relieved, even, though I still felt betrayed, kind of. Standing next to me with an arm still wrapped around my waist, Emily waved them goodbye as they drove off while I had my eyes fixated on the floor in my teenage boy's shame.

Once back inside, Emily closed the door and leaned her back on it, crossing her legs.

“Now, just to make this clear, Jackson,” she began reading my rights. “Yes, I'm getting paid to babysit you, but clearly, that's not really necessary. At your age, I'm sure you can handle yourself. Guess I'm more here to watch you don't wreak havoc with one of your stoner friends again. Now, we can make this the fun way and I'll just be your 'elder sister' for two weeks, if you will—if you behave, that is. If not, I can just as well report to your parents and I'll very gladly do so, trust me. And that's your ticket to summer school, I reckon.”

My initial amazement about her looks faded away with every word she uttered in that angelic voice of hers. While still being angry at my parents, my loins had a life of their own, however, as my very own teenage hormones were boiling in my pants.

My mood somewhat improved, when she started the second half of her speech, “Look, we're in the same boat. We cannot really get out of this situation and it's up to both of us to make this work. Frankly, I'm looking forward to spending an awesome time with you. I trust you and I can just as well have a blast and get to know each other better in a fun way. Watcha say?”

I swallowed from the way she emphasized the word 'fun' but quickly discarded my impressions as teenage wishful thinking.

“Uh, sure,” came out with a timid voice before I regained my composure and nodded in approval. Sure, spending an 'awesome' time with a solid ten. Sounded like an actual plan. That prospect didn't seem so bad after all.

“I, uh, think we can, uh, yeah, work... things out, uh, I guess.” Wow, that sounded like a real ladies man, didn't it? Shit! First impression ruined.

She giggled her most genuine girlie giggle.

“Not that used to talking to girls, are you?” she investigated, hitting the nail right on the head. She approached me. “C'mere, you little cutie-pie.” She softly lifted my chin which I held bashfully planted against my chest and planted a peck on my forehead. “Time I teach you how it's done.”

She let go of my chin and put her arms on my shoulders. I felt her eyes transfixed to mine although I didn't return her gaze.

She sighed in a big sisterly way, “Look, Jackson. There really is not that much about it. First of all, girls are just humans too. Got that? That's all the fuss there is about it, honest.”

I nodded my head yes, ashamed of my inability to keep my shit together. I felt like every male teenager would in that situation: tiny, powerless, weak. My heart did somersaults, my dick begged for attention, my stomach churned, my head was spinning and, at the same time, trying to find elaborate plans to prove my virility whilst discarding any such thought and talking myself into knowing she was way out of my league. Did that make any sense? Yeah, teenage hormones, you get the idea.

“So, Jackson, tell me about your plans for these two weeks. I'm sure we can work something out. Any friends coming over?” she inquired. She bit her lower lip and smiled, “Oh, I bet you're expecting your little girlfriend to come over for some one-on-one action? Now I know why you're so shy about it. Your first time? A cutie like you has the girls lining up, I bet.”

All I managed to do was to look her dead in the eye and feel the blood rush into my cheeks, causing me to blush once more. When had she become so bubbly and open-minded? I remembered her being a real pain in the ass and my parents using her name as an effective threat whenever I didn't behave. It had been about five years and now look at her, standing there in her Daisy Dukes, showing off just enough for me to see her belly button, just that little hint of cleavage in her tight-fitting tank top which had me wanting to see more, and her shining hair which practically invited me to loosen her bun and run my hand through it.

“Oh, sorry, sweetie,” she began, shaking me out of my daydreams just before I started drooling on the floor. “I forgot not all guys are used to my openness. I'll be more careful in the future.” She playfully hit my shoulder. “See, now I also blew your first impression of me. Guess we're even.”

I sighed and rubbed my shoulder where she hit me. With a crooked smile, I chuckled, “Thank you, Emily.”

“Huh? What for?”

“For setting my mind right. You really had me intimidated.” This confession of vulnerability came out before I realized what I was saying.

“Jackson...” she said, looking at me questioningly. “Of all the guys I've met, only very few could openly admit their weaknesses—and certainly not at sixteen. That's a very manly thing to do, you know? It takes more courage to share your weakness than to cover it, really. Most guys do that with fake overconfidence. It can really be annoying. ...and this after we just, like, met? You sure you're just sixteen?”

I hit her on her shoulder too. “Now that was a major ego boost.”

She smiled at me. “You see. You're already talking to me like I was a normal human being and not one of these 'weird other beings' with tits and no dicks. Wasn't that hard, now was it?”

Awkward silence—which she thankfully broke. “I'm really thirsty and could use a drink. If I remember correctly, the kitchen's this way,” she said, walking in the right direction, giving me a great view of her taut, heart-shaped ass. Gulp! “I'm gonna pour me a glass of water. Wanna have one too?”

“Sure. We got coke and limo if you prefer, though,” I shot back, giving my best at keeping my voice from sounding like too obviously caught red-handed.

“Nah, tap water will do just fine. What can I get you?”

I handed her two glasses and we drank our glasses of water in the kitchen, she leaning against the stove and I against the counter. I fetched the reddest apple I could find from the fruit bowl and, using the balls of both my thumbs, broke it in two halves to offer her one.

“How'd you just do this?” she asked, fascinated.

“I just broke it in half. Mom always said I should learn to share with others so I just tried until I succeeded. It's not that hard, really.”

She lifted her eyebrows and shrugged, intrigued, like Mr. Spock in the Original Series.

“So, about those vacation plans of yours. What did you have in mind?”

“Well,” I began hesitantly, not wanting to sound too childish. “Having the house to myself, I wanted to play some serious Zelda. Mom complains all the time when I play more than an hour straight.”

“You wanted to waste your time playing video games? Seriously? With that killer weather outside?” she commented, shaking her head. “On the other hand, Zelda is pretty awesome. My ex played it all the time.”

The way she mentioned him nonchalantly stung straight into my heart, reminding me in a most unpleasant way that she was out of reach for me.

“Yeah, we can play some tonight when we're comfy in our PJs. Take turns you and I. How's that? Sound like a plan? Or do you have Mario Kart?” she suggested, having me picture her in appealing underwear that hardly passed as comfortable to sleep in. “We can also just watch some flicks. You guys still have satellite, don't you? Or that new thing everyone's talking about. Netflix? We never had a TV or anything. We couldn't afford it, my parents used to say. And thinking back to it, it probably was for the better. I would have been glued to that thing.”

I chuckled, “You didn't miss that much, frankly. I sure did spend more time than necessary in front of that thing instead of learning although I knew well enough it was only designed to make you stupid." With no hint of a second thought, I nonchalantly delivered my next proposal like nothing, "We don't have Netflix but I know how to decode the x-rated channels on the satellite if that suits you.”

Did I really say what I heard myself say? What kind of sick mind...?

“Well that was quite a bit snappy for a boy your age, kiddo,” Emily laughed while my complexion changed from pale to crimson once more. “We'll see about that. Who knows? If you're nice...”

My eyes were open wide and I just wanted to the ground to swallow me up.

Again, she hit me on my shoulder like an old buddy. “Aw, c'mon, sweetie, don't be like that. It just slipped out of your mouth. Happens to everyone. Know what? I prefer guys who talk turkey.”

“Sure, thanks. Was that an offer?” I stated, still mindlessly testing these uncharted waters, yet this time, doing it on purpose.

“Now, don't get cocky, will ya?” She smiled at me and pinched my cheek. “Aren't you just the sweetest thing when you blush?”

Not knowing what to answer to that, I just gulped down the lump in my throat and tried to move my eyes to look at something else, but they just seemed glued to hers.

“I'm just teasing you, Jackson,” she added to my relief. “I know I was hard on you when I used to babysit you all those years ago. Well, I was a bitch, I admit, but I've changed since. For the better, I hope. You'll see.”

To add to my confused shyness, she winked at me, most probably knowing it would bamboozle me all the more. She sure had changed. For the better too, it seemed to me, both physically and mentally. The knock-out girl standing there in the kitchen, flaunting her toned legs was a far cry from the insufferable brat I remembered.

“Hey, uh,” she began, hesitating a bit, “without wanting to sound like a bore... Your parents said you needed some help with maths and chemistry classes?”

No, please don't ruin this perfect picture I have of you!

“I'll very gladly give you a hand, but you'll have to play along. The more you apply yourself, the quicker it'll be over and we can go back to enjoying summer, alright? And I think I know just how to make you understand these subjects. How about we start right away? The sooner, the better.”

I looked at her understanding smile and came to think it didn't have to be all that bad after all. It probably wasn't more than just a necessary evil. And, heck, what bad could come from learning something? Wow, did I really just say that? This girl truly seemed to turn my mind upside down.

“I have a suggestion,” she let my train of thought derail. “How about we get some work done and then head to the mall for some lunch? My treat. Your mother gave me an envelope big enough to feed both of us through the better part of the entire summer. And after that, well...” She paused to bite her index finger. “Maybe you can help me with some shopping, depending on how well you do this morning.”

My face must have gone pale as a corpse since she started laughing hard enough to have my eyes drawn to her breasts which wiggled with her every chuckle—a sight that instantly let me forget my inherent fear of shopping.

She poked my shoulder and said, “Don't worry, Jackson. I know it sounds horrible to you, but you'll love shopping with me. I promise. So do your best and apply yourself, okay?”

Whatever that was supposed to mean... Sarcasm? It sounded about as dreadful as a prison sentence—in terms of a sixteen-year-old boy anyway. Ugh, these countless wasted hours of shopping with Mom! Sometimes, I thought I'd notice a pattern in her shopping behavior since, especially when grounded, she took me on her trips of excruciating torture through the shops. Her type of payback, probably. As if I was such a handful—disregarding the weed incident, that is.

A couple of hours later, we were sitting, as agreed—or better: 'suggested' by babysitter's decree, of course—in the patio of the mall, munching on some hot dogs. My head was still smoking from all the sines, cosines and tangents. At least, Emily had managed to straighten out some of my bigger understanding issues and all seemed a little bit clearer. Still, we were to spend some considerable time—hours, possibly—shopping; hours that could have been spent enjoying the 'killer weather' as she had so accurately phrased it. Or, uh, playing games, I admit.

“I'm gonna need just a few new clothes,” Emily explained with her mouth half full. Yeah, just a few. Whatever that might mean? “Is your girlfriend alright with you looking at other girls in clothes stores?”

A slightly pissed "I got no girlfriend, now stop asking" was all that came out. I was just too consumed by my blank hatred towards shopping to actually register the contents of her question. I just shrugged and took another bite of my hot dog that suddenly had the bitter aftertaste of a death row inmate's ominous last meal while I ignored her flirty "You can tell me, I won't be jealous."

So there I was, sitting on my chair in front of a dressing room in a women's clothes shop I ignored the name of, waiting for Emily to pose in front of me in a whole selection of clothes. The pile she had taken into her stall had me afraid it might really take hours until we would leave that shop, and that was just the first of many. Of course, the changing cubicles were in the middle of the lingerie section. Even the stores were specifically designed to make a teenage boy feel uncomfortable. I cursed about my mother and her will to punish me in various ways. Agreed, some of my misery was indeed self-inflicted—I was able to acknowledge this despite my juvenile immaturity—but this was just way off the scale.

I kept wallowing in my little self-pity, getting grumpier by the second until Emily poked her head out of the cubicle and said with a sly grin, “Wanna come over and have a look?”

So now, imagine that little brat I was, sitting there in the middle of women's underwear getting invited by a smoking chick to enter her stall and give my judgment of her selection of garments. Sure, most usual situation and absolutely not embarrassing if seen by someone.

“Pretty pleeeeease,” she pouted.

I hissed, “Alright, I'm coming, but keep it down, will you?” which caused her to giggle girlishly. She knew. She had planned for this! That bitch!

I took a cautious look around to see if anyone was watching but her pull on my arm didn't leave me any choice.

“What?!” I yell-whispered before my voice cracked and my mouth sprang open as my eyes wandered from her face all the way down to her feet and up again, drinking in the sight of Emily in a bikini.

“I thought you might wanna give me your verdict,” she explained, slowly turning around, then playing with a strand of her hair, “but, judging from your face, you like it alright.”

“Alright?” I asked. “I like raspberry syrup with cold sparkling water 'alright' but you're, like, a real stunner. Really.” Did I really just say that?

“Thank you, but now, for real, like, minus the teenage hormones,” she began, placing her hands below her breasts. “I love this bikini but the push-up padding makes my boobs look so big, don't you think? I feel like cheating with those and it's not really a snug fit. Maybe if I...”

With that, she started fumbling around at one of the bra cups with me standing right there, shamelessly staring at her, hoping I'd get a flash of her nipple, without realizing my indecent behavior. There was no way on earth she didn't do this intentionally.

After having removed both push-up pads, the bra did, in fact, look like a much comfier fit as it outlined the curve of her breasts perfectly and let me swallow hard when I saw her nipples poke through the synthetic fabric.

“Much better, isn't it?” she asked before looking at me a bit surprised. “Oh, sweetie, I'm sorry. I should have known better than to play with my boobs in front of you, poor thing.”

Had she really been that absent-minded? No way! Either way, much to my delight and relief, she explained she had only taken that huge heap of clothes to the dressing cubicle to make a surprise out of her bikini. She ran her hand through my hair, kissed my cheek and thanked me for my patience, only adding even more to the towering pile of confusion and insecurity I was already being overwhelmed with.

We rode our bicycles home right after she had paid for the bikini. On the way back, I couldn't manage a single word. My mind was still totally absent and filled with the pictures of her that were like etched into my memory while I was still beyond mortified for sitting around alone in the lingerie section. I was sporting a boner hard as polished steel in my shorts and silently tried to concentrate on something other than Emily's inviting body. Still, however wrong and awkward, I had already decided I would use these exact pictures as wank material this same evening—and, most likely, many, many evenings thereafter.

Once back home, I inquired, “What did you buy that bikini for?” I paused and hesitated, wondering whether I should really push my question harder. “It's not for, uh... well... It wasn't just for some teenage boy show-and-tell, uh, was it?”

She smiled playfully, yet mysteriously when she replied, “Oh this? I just wanted to treat you to something nice since you were a terrific student this morning. Did you enjoy the show?”

So this was just to tease me. I should have asked her to...

“Just kidding,” she interrupted my teenage fantasies. “I know the perfect place for a dip on a hot summer day down at the river in the middle of the forest. And we'll be alone. I thought this might be fun. Just the two of us? Tomorrow, maybe? And if the weather holds and you enjoy it, perhaps a couple more times after that?”

The rest of the afternoon passed without any notable events. Emily was just lying in an easy chair in our garden, reading some book and tanning in her most recent acquisition while I nervously alternated between sitting in the grass next to her, fidgeting on my phone and trying to take naps every now and then—not that I was able to fall into any stage of sleep with those images of her still dominating my every thought. For a reason unclear to me at that point, I seemed to be actively seeking her company even if we mostly had no social interaction whatsoever that afternoon. I just felt at ease hanging out with her. Sitting there, I found myself trying to catch the smell of her shampoo over and over again as it seemed to appease the dancing hormones in my belly.

After dinner, which consisted of some leftover mac'n'cheese, I took my shower first. As agreed upon earlier that day, I microwaved two bags of popcorn while she was taking hers.

The living room couch was big enough to watch TV almost lying on it. I was sitting cross-legged with the large bowl of popcorn on my lap, waiting for Emily as the Switch started up. I was sitting comfortably in my pajamas which consisted of a basketball t-shirt and a pair of loose boxer shorts. I lazily shoved a fistful of popcorn in my mouth and started Mario Kart while munching on them.

The moment I lay my eyes upon Emily in her oversized t-shirt which went to her upper thigh, I almost choked on the popcorn. I had to catch my breath through my nose when I saw her auburn curls frame disorderly frame her face. The few freckles that were scattered around her nose were of the exact same color. She sat down next to me, pulled one leg close to her chest while leaving the other stretched out, causing the t-shirt to slide up and grant me a somewhat disappointing glimpse of her plain cotton granny-style panties. Still, it was a girl's lingerie! Get that idea out of your head, dork!

I forced myself to look her in the eye while I gulped down all the popcorn in my mouth at once, trying to concentrate on my peripheral vision which gave me a blurry view of her crotch. It was obvious too that she had removed her bra. Feeling the weight of the bowl on my growing erection, I considered myself lucky to be able to hide the corpus delicti of my desires. Please don't take the bowl from my lap!

“Care to hand me a controller and some popcorn or you wanna keep gawking at me?” she asked, giggling, clearly enjoying the effect she had on me.

I shook my head and replied, bashfully, “Sure, here.”

“Did you at least like what you saw?” she asked while choosing her character.

Not sure what to say in my defense and afraid to just turn things to the worse, I chose to go all-in since she had told me she preferred guys who 'talk turkey': “Yeah. It was a nice view.”

She dug in deeper, giving her voice a mock annoyance, “Nice? Which nice? Like 'nice-nice' or more like 'yeah, nice now shut up and let's play' nice?”

“Whichever suits you best,” I casually replied, probing how far I could take the provocation.

“My, my, look who's getting bold all of a sudden. Maybe I was just trying to extract something from you, hint, hint, wink, wink.”

Deciding to play along, I rolled my eyes in an overly staged way and kept asking for it: “Whatever. Girls...”

She slapped me on my exposed thigh and said, “I was fishing for compliments, you insensitive oaf!”

Only realizing at that exact moment I hadn't really thought any of my words—or actions for that matter—though, I couldn't figure out how to react or what to say, so, naturally, fueled by her unexpected slap that had hurt my ego just that little bit, my reply came a bit more salty than necessary: “Ouch! That hurt. And yes, you are a pretty girl. Yeah, there's that. Happy?”

“I'm sorry. I didn't mean to corner you,” she said. Her concern sounded genuine. “I keep forgetting how young you really are and that lots of guys aren't comfortable with my way of talking straight. Please tell me I didn't hurt you.”

I sighed and looked at the screen. “Can we just play now?”

Emily gave her best shot at defusing the situation: “Be prepared to get your ass handed, buster!”

Feeling the boy in me challenged, I shot back, “Oh yeah? I'll show you who's gonna whop whom!”

“You bet!”

She hadn't exaggerated one bit. She indeed did beat me on most tracks. Was it because I was intimidated by her or was she really that good a gamer? Probably both. Whatever it was, I had to admit I was somewhat grumpy from losing so badly.

“Alright, I'm pooped. I'm gonna go to bed,” I said, unsuccessfully trying to hide my boyish frustration.

“Oh, come on! You're just pissed because you got properly annihilated by a girl,” she teased.

I grunted something intelligible only to prove her right.

“Don't be like that. Come on. It was just a game,” she said, still carrying that merry timbre which irritated me a bit in that situation. Seeing her words had no positive effect on me, she—raising her eyebrows—teased further, “Know what? Why don't you put your money where your mouth is and unlock these x-rated channels like you said? See if there's anything good.”

“Yeah, whatever,” I aspirated.

I punched the password Dad had imprudently written down on a note placed on his nightstand into the remote control. Instantly, a curvy blond woman with humongous knockers getting properly humped from behind popped up on the screen.

“Wow, look at her!” Emily exclaimed with fascination. “Do you think these are real? Those gotta be like G- or H-cups at least.”

“My guess: they're real. Just look at the natural-looking sag and how they bounce back and forth. Looks natural to me.”

“Oh, lookie there. We got an expert over here,” was her playful reply to my inattentive statement. Hell, I was still talking to a girl, wasn't I? When had I become so comfortable around her? She sighed with an undertone of envy, “I wish I had tits like these.”

I thought I had heard a nuance of discontent with her own body. “What? For real? She looks like a cow with swinging udders. They're far too big. Do you imagine the weight she has to carry every day? And the back pain?”

Emily looked at me as if she couldn't believe what I was saying. “Are you sure you're only sixteen? I've never heard a guy your age talk about girls in such a considerate way. Heck, not even a guy my age! You sure you got no girlfriend?”

“Thanks, but, really, there's nothing to be jealous of. Besides,” and that was the moment my brain didn't give a second thought about what I was about to say. Okay, I'll admit I hadn't even given it a first thought either. “Besides, yours are just perfect. What's that? A solid B? Fits a dude's hand perfectly. Why should they be any bigger?” I delivered these words as if it was the most normal thing in the world to say to a girl I only just got to know more intimately. As already pointed out: I hadn't given them much thought.

“That... That was... just,” Emily started as it dawned to me what I had just said. A sudden wish to drop dead then and there suddenly filled my mind and my heart began racing in expectation to receive a well-deserved slap and the lecture of my life about manners, yet she beamed at me and continued, “...the nicest inconsiderate thing anyone's ever said to me.”

She placed her hands on my neck and pulled me close. I felt her pressing my face against her chest. It was as unexpected as it was discomforting yet pleasant. My breath stopped from feeling her soft breasts against my cheeks and the way she hugged my head so tightly.

“Since you seem to like them so much...” she said.

My first feeling of boobs. Sure, I had felt those of my female friends when casually hugging them, but right in the middle of my kisser? That was a first and it felt amazing.

“Woah there, kiddo,” Emily chuckled when I kept my face buried between her breasts after she let go of me. “No reason to get greedy here.”

“Sorry, Emily, I was just a bit lost in the moment,” came my coy answer while avoiding eye contact.

“Aw, you're so cute when caught red-handed,” she put me in my place with her sweetest tone. Biting her bottom lip, she added, “But this will have to stay between us. I don't think your little girlfriend would approve of you snuggling your face against another girl's boobs.”

Again, I felt the capillaries in my cheeks getting flooded with blood.

“Screw that girlfriend thing,” I began insecurely, fighting the words. “It's not like... I mean...” I stammered, being at a loss for words. “Once and for all, I don't have a girlfriend.”

Emily raised her eyebrows and tried to look into my eyes as if she were looking my statement was honest.

When my eyes fell to the floor and I tried to bury my head between my shoulders, in teenage shame, she said, “So you were not lying to me?”

I shook my head no, unable to say a word. The uncomfortable silence was filled by the fake moans from the TV. The scene had lost its appeal but neither of us would turn that thing off.

“A guy like you and no girlfriend? Are you kidding me?” She paused to look at me head to toe and back. “You're good looking, smart, you're an attentive listener and a very considerate guy. You're perfect boyfriend material. You're, like, a mother-in-law's wet dream for her daughter. I'd totally go out with you if only you were a bit older.”

Her words were like a sting right to my heart and twisted my stomach in which to that moment, butterflies had been fluttering. Feeling horny from the movie and seeing her in her pajamas which had my mind undress her and drinking in her perfect body had me confused to no end. Both my body and mind were unable to cope with this constant change of strong emotions.

Unable to think straight or to control my reaction, I almost yelled, “Yes, that's just what the problem is! You girls and your constant excuses!”

I could see in Emily's expression that I had snubbed her. I realized my mistake only to have more negative emotions pile up on me even higher.

Without being able to restrain myself, the words just spilled out of me: “Okay, I'm sorry I said that. That was an oversimplification. I mean, you clearly are way out of my league, I see that. But still, your excuse, however justified it might be in this case, just triggered me, okay? Do you know how many times I got rebuffed for being the nice guy? What is it that you girls find in these deadbeat jocks that discard you without batting an eye after they're done treating you like meat? It's not like I'm asking for a textbook romance, I'm just sick and tired of hearing the same excuses over and over again. And then, after a girl got her heart broken, suddenly, I'm good enough again for a shoulder to cry on. I've heard it all: 'Why can't more guys be like you?' Yo, I'm sitting right here, bitch! I am a guy like me, in case you didn't notice, and no, I'm not gonna ditch you like some useless old trophy because I genuinely care for you. That's why I'm just a shoulder to cry on? Fuck this shit!”

By the end of my monologue, tears were swelling in my eyes. Yes, it was safe to say I was desperate to get a girlfriend and had made some bad experiences. Like everyone, I guess. Yay, teenage years!

“Oh, baby,” Emily said when wrapping her arms around me. She pulled me close and gently ran her hand through my hair when replying, “That's the infamous friend zone. I feel you, kinda. I'm not gonna pretend I was a saint at your age. I was just like you described: one of those girls who just followed the mainstream. I'm not particularly proud of that time. I too had a guy or two who were just good enough to complain to. I failed to realize they were the only true guys in every way. But yeah... Feeling like a trophy for a useless jock, as you so accurately put it, gave you a better status, I guess. Thinking back to it, I regret a lot how I treated these poor bastards back then. In the end, all I had achieved was shattering some perfectly good and sweet guy's heart and getting my own heart broken countless times too.”

She let go of me. I looked in her eyes, a heavy lump in my throat that prevented me from saying anything without sounding like an immature sob.

She pressed her lips together and, with a melancholic smile, added, “This, and a less than disappointing sex life. Do you think any of those jocks were any good? Most of them had little understanding of genital hygiene and still wanted to get sucked off.” Her wry smile turned more lively as she went on talking, “...and absolutely zero notion of what the clit is good for.”

Upon hearing this, the frustration in my heart made way for warmer feelings. I chuckled at her last remark.

This time, she blushed when she nibbled on her bottom lip before saying, “Make sure you can give a girl proper head, alright? She'll brag about it with her friends, just to make them jealous.”

“Yeah,” I chuckled with my eyes still swollen with tears, “like who's gonna teach me? You?”

“It's not like I'm totally off-limits, you know?” came her reply which made me gulp and choke on my own saliva. She laughed, “Hey, kiddo, you gotta work on that poker face if you really wanna learn how to flirt with a girl.”

Taken off guard and blushing through all shades of pink over burgundy to crimson, I was still unable to form a coherent thought, let alone move my lips that were parted, leaving my mouth open in the most moronic expression. Bamboozled as I was, a featherbrained “uh...” was all I could manage while in my head, thoughts popped in and out without making any sense.

“You gonna say something or just keep staring at me like that?” Emily taunted.

“Yeah, you're right.” I began, finally able to extract a—given the circumstances—somewhat pithy come back out of my flooded brain. “The action on TV is so much more interesting than the real girl sitting on the couch with me.”

Emily's grin read 'attaboy' all over when she squeezed her breasts together and tantalized, “You sure you've seen enough of me?”

“Now that you say it...” Afraid I might have screwed up the beginning of my reply, I decided to go all in. What did I have to lose? She was teaching me and well aware of my inexperience, so why not test the limits? I finally turned off the TV and resumed, “...I wouldn't mind seeing more.”

Emily crawled to me and planted a peck on my forehead. “Now let's not get ahead of ourselves here, kiddo. You still got two weeks to get into my panties.”

I gulped and—my head racing with thoughts revolving around whether I had heard right or not—looked at her clement smile which turned into a dirty smirk after a few seconds.

“Aw, you're really just too cute when your inexperience shows,” she rhapsodized.

I shrugged and shook my head. I was feeling tired from the constant change of emotions and the hormonal roller coaster I had experienced the entire day.

“Emily, I, don't wanna sound like a bore, but I'm just pooped, really,” I said, yawning. “I just gonna go to bed.”

“Sure, Jackson. It was a nice day with you. I hope you were able to enjoy it just as much.”

“Yeah, thanks. It sure was a blast. I can't wait till I'm well-rested again. Goodnight.”

“Wait. Don't you just wanna sleep here on the couch with me? I mean, next to me, of course. I can use some company tonight since you brought back all these past memories. Don't worry. I won't hold this against you. I just feel like I need a good hug.”

I bit my lower lip before replying, “Okay. Let me just get another blanket and two pillows.”

I did as told. When I came back, she patted the space next to her. When I lay down, she turned her back to me so I could spoon her. We fell asleep right away.

Same as The Babysitter I: Reunion Videos

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A Night at the Reunion

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Hardcore
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After finishing up my vacation with the kids, I dropped them off at my parent’s for the weekend. Rex was entertaining clients and would be home later in the evening. I wanted to have a sexy weekend with my husband. I had been thinking about Sandy, the babysitter. My husband and I had a threesome with her for our anniversary. I wanted to surprise Rex with another threesome with her. I couldn’t stop thinking about our threesome. Sandy and her squirting orgasms made me hot. Several times on...

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1 year ago
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Babysitter Makes Me Lose Control

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2 years ago
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When The Babysitter Came Part II

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1 year ago
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Having Fun With The Babysitter and her Boyfriend

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2 years ago
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Thats My Babysitter In That Porn Video

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4 years ago
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Dont Tell Mom The Babysitter Feminizes

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3 years ago
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2 years ago
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Our Babysitter Watches Us

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2 years ago
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What If The Reunion

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Class Reunion

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3 years ago
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Blonde Mom Fucks Black Babysitter Pt 1

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1 year ago
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Babysitter Makes Her Move

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4 years ago
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my babysitter my teenage whore

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3 years ago
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The Busty Babysitter

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2 years ago
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3 years ago
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2 years ago
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2 years ago
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Babysitter Gets Caught Then Gets Schooled

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3 years ago
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2 years ago
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Our Babysitter and Her Mother

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1 year ago
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Babysitter Worth Keeping 12

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2 years ago
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The Babysitter

The Babysitter She gave a light tap on the door, knowing that there was a baby in the house probably trying to sleep. The tapping was loud enough to alert the child’s mother who was sat in her living room. The house had been silent so the sound startled the young mother who, up to now, had been playing through the infinite possibilities of the night ahead in her mind. The more she thought about it, the more nervous and edgy she made herself. At least her 3 year old son, Callum, had drifted off...

Lesbian
1 year ago
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Bedding The Babysitter 3

Note 1: All characters are at least 18 years old. Note 2: Although I recommend you read parts 1 and 2 first, here is a summary of this series so far... Part 1-Megan, a dominant but caring lesbian, seduced her cute and innocent babysitter Jenny. Part 2-Megan takes her new submissive lesbian shopping, makes a fantasy come true with a cheerleader that Jenny had dreamed about forever and took her to a special lesbian only bar. Bedding the Babysitter: A Cheerleader's Recruit What a weekend. Jenny...

Lesbian
2 years ago
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The Reunion

The Reunion By Mister Double-U Part I It was a bright sunny fall afternoon as Ryan and Ashley wandered through the flea market. It was a tradition on Sundays that they both enjoyed. They used to go for fun, to look for little knickknacks and old videos. Now, they went looking for baby items. Ashley was 5 months pregnant and very much showing. She waddled through the flea market feeling extremely self- conscious. Ryan held her hand and kissed it. She smiled and they...

2 years ago
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Chrissies High School Reunion

Chrissie’s High School ReunionWhen the announcement arrived in the mail notifying Kelly and I that our High School graduating class was organizing a ten year reunion we spent that entire evening discussing the pros and cons of attending. I was fairly certain that I wasn’t interesting in attending but Kelly insisting on listing all the reasons why she felt we should attend.She was interested in going because she wanted to make passes at all the “stuck-up bitches” that pissed her off in high...

1 year ago
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Brendas Reunion

Brenda Powers received the invitation to her 13th high school reunion in the afternoon mail and was sitting in her kitchen pondering if she really wanted to go or not. For the umpteenth time that afternoon she looked at the date for the reunion and realized that there wasn't any reason for her not to go ... well only one reason really — that bitch Trisha Grant. Brenda wanted to see all of her old friends and dance and have a few drinks but if Trisha showed up she didn't know what would...

3 years ago
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Naughty Babysitter

Introduction: OK readers, here comes a LONG story that I have been working on for a while. I dont think this will become a series unless I get requests for it. Tina comes home early and finds a surprise in her bedroom, the babysitter masturbating on her bed. She could just fire the girl, but decides to punish her, while living out one of her fantasies. Paul and Tina have been married for about 6 years, and have a 3 year old daughter. Instead of taking their daughter to a daycare, they have a...

3 years ago
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my new babysitter

The new babysitterAt this time i want to tell you a story of when i got a new babysitter.one evening my parents chatting and came up with the idea of going out on a romantic dinner for two being they were married for about 11 years and didn’t get the chance to go out much for some alone time for a long time now,being i was sick often and hadand therapy and other activities and a baby sister my mom had her hands full.my dad brought up the idea of perhaps having dinner just the two of...

2 years ago
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The Babysitter Rules

Jessie Flanders checked the time on her cell phone as she neared the elegant Carter home. She was a minute early for her babysitting job. As she made the turn onto the Carter’s front walk, a cab pulled to the curb and blew its horn. She reached the door and was about to ring the doorbell when it popped open. A good looking woman in her late thirties dressed in dark slacks and sweater peered at her over her glasses. “Are you the babysitter?” she asked. “Yes I am,” Jessie said. “The sitter’s...

2 years ago
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Farm Girl 220 Year Class Reunion

Following the summer of  '83 Eddie went away to college and I remained home on the farm and attended a local college taking up business. Throughout Eddie's four years of college we remained in contact and went out together on various holidays when he came home and also during the summer months. Regardless of what the future held, Eddie and I were glued for life.  During those years I also met Tom and though we were not under any commitment to each other we went out together a lot and became...

Straight Sex
1 year ago
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Somebody Had To Take The Babysitter Home

Mike’s night was falling apart.“But honey, this is supposed to be a romantic evening with,” he struggled to phrase it with finesse, “an intimate ending. How are we supposed to do that if you end up falling asleep before I get back home? Can’t we just call her a cab?”His wife, Cindy, sighed in response. “Sweetie, someone needs to bring Megan home, and I’ve had too much wine, so it’s going to have to be you,” she explained as she looked at him with a face depicting the annoyance of telling a...

Oral Sex
3 years ago
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Engaging The Babysitter

I walked towards the door and saw her through the small window. 'Oh, there she is the barely legal dazzling brunette I have babysitting my son. What I wouldn't do to give a ride, and I don't mean in my car. Shit, she is wearing a dress like that to a babysitting gig? Is she trying to turn me on now?'I opened the door and saw her through the glass storm door. She just smiled and waved for a few seconds, and I had to return the favor.I opened the storm door too. "Hello, Alli, you are looking...

Taboo
1 year ago
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The Babysitter II

The following is a continuation of the original story "The Babysitter" previously published on this site under the Taboo category. If you haven't read the original story, please do so before reading this one, as it will introduce the characters and circumstances so this one will make more sense. * The extra week that my wife was gone stretched into two. Amy had gone to her sister's to help her while she and her husband were having troubles. They had split for a time, and Amy's sister was...

Taboo
1 year ago
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BlondieDennis The Menace The New Babysitter

Blondie/Dennis The Menace: The New Babysitter (Or When Dennis Meets Blondie)by Sniper32One Friday night Dennis was introduced to his new babysitter, a nice younglady named Blondie Bumsted. She was a 35 years old friend of his mother, shewas a stunning 5'9, slimmed hipped, long legs, a nice ass and a perfect setof 38c breasts.Denise's parents Henry and Alice were going out for dinner and dancing fortheir anniversary and would be gone most of the night.Now as everybody knows Dennis is a handful...

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