The Babysitter IV: Conclusion free porn video

I woke up with a dry mouth and a disgustingly sour taste on my tongue. In the bathroom, I tried to drink away the nasty feeling but my throat was so raspy from the dehydration—almost sticky—that I had to force down the first two or three sips past the soreness. As bad of an idea looking in the mirror was, I decided I didn't care. My hair looked as if a firecracker had gone off right in my face and I won't mention the obvious tiredness written all over my ugly-ass grimace.

I went back to my bedroom to find I hadn't been sleeping alone. Emily was spread starfish-like all over the bed, peacefully snoring away—naked. After shaking my head to rid myself of the initial confusion, I felt this stupid teenage pride after my first night with a girl until I remembered how abysmally bad I had performed. Before it even set in, however, instead of wallowing in my habitual self-pity, I decided to swallow my pride, get by with it and put some effort into myself.

The first thing I decided was to make it up to her with a hefty breakfast. Had worked with me twice, so why not return the favor? My time to shine, I thought. Let's see if all these times I watched and helped Mom so I could impress the girls with my cooking skills one very distant day finally paid off. So how did this French toast thing work again?

I was too busy preparing breakfast to have my head linger on the previous night's events. I needed to be quick if I meant to surprise Emily by bringing her the meal to bed.

Finally, I walked up the stairs with a tray in my hand, carefully balancing the practically overfilled coffee mugs and juice glasses.

When I entered my bedroom, Emily was sitting on the edge of the bed in her loose nightie, rubbing her eyes. I got a good view of sideboob through the sleeve before she noticed me and her face lit up.

With that heart-melting, beaming smile of hers, she looked at the tray in my hands, eyes slowly opening wide as far as her drowsiness allowed.

"Did you just do that?" She waited for me to nod happily. "A French toast tower with butter and maple syrup? For real?"

"Yeah," I replied, "and with some caramelized sugar on top and mashed blueberries spiced with cinnamon between the slices."

I eyed her up while she was munching on her breakfast, looking back at me, cheeks filled with a half-chewed mouthful.

“Awefum,” she tried. “Beft Fentf toaft evuh.”

I accepted what I interpreted as a compliment with a smile and timidly munched on my own serving.

“Ferioufly,” she almost coughed and then swallowed all the contents in her mouth in a single, loud gulp. “Who taught you to make these? And what's the occasion?”

I took a deep breath, hoping this would help me muster my courage to take the bull by the horns. I too gobbled down my practically intact mouthful and washed the raspy feeling in my esophagus with a large sip of too-hot coffee which did not exactly help with the displeasing feeling in my gullet. My tear-filled eyes were still transfixed to hers.

“What?” she asked.

“I'm sorry, Emily,” I replied sheepishly after another two breaths but wasn't able to continue before she inquired on the nature of my distress anew. “...about yesterday. I... I did a horrible job as your boyfriend. It had to be terribly bad for you. I'm sorry for being such a—”

Her hands were on my face and her lips on mine before I was able to finish the sentence.

“Jackson, listen,” she said, staring right into my eyes with the softest, most comprehensive expression in hers. “It's okay. You were too excited, you were too eager so you came a cropper—big deal! I know these things hurt your ego but do you really think I would have accepted to be your girlfriend if I hadn't expected this to happen? It's nothing unusual, really. No reason to beat yourself up. Besides, we've still got plenty of time to practice so get up again, dust yourself off a little, straighten your crown and off you go again.”

She let go of my face and I kept looking at her with that crooked, intrigued grin in my face. She just had this way with me. She just knew how to cocker me up again in any situation. The prospect of plenty of practice made me forget all my self-pity and my endless questions why she was so understanding with her boyfriend who had turned out to be just as useless in bed as those jocks.

When we were done with breakfast and tidying the kitchen, we picked up the routine we had established these past few days: hit the books in the morning and free time after lunch—and that free time was something I was looking forward to. Oh yeah!

After just a few minutes shy of two hours of concentrated, unusually productive work, we decided to take a break. Emily looked like she was thinking about something.

To my inquiry, she replied while the coffee machine was grinding the beans, “I was just wondering what type of condoms you have. Care to show me the pack?”

I rushed to my room to fetch the box.

"So let me see those," she requested, pointing at the pack of condoms. I handed it to her and she read the specifications. "Lemme see... Okay, just what I thought."

I looked at her quizzically. "What?"

"Just one sec," she cut me off, holding up a finger. "Yeah, I think I know what the problem is." She looked at me, waiting for me to raise my eyebrows. "Look here, read what the diameter says. It's just those few millimeters too tight for you, I think."

I looked at her, bedazzled, wondering how she knew so exactly what I needed.

She explained, "Remember when Jenny said I told her you were well-endowed?" I gulped hard. "You're not, like, super huge, but you're certainly that little extra above average—in circumference too. Your weenie needs more room, is all, so this afternoon, we'll go to the gas station and buy some better-fitting rubber. Also, we'll make sure to take those with a desensitizer in the tip. That should make you last a lot longer. They have those."

Condoms with a desensitizer? I had no idea. It's amazing what's out there! My eyes lit up. So basically, this meant I was going to get some more real action today—possibly a lot more in the near future if I performed better this time. Chill, dude. Breathe slowly and steadily. Calm down now. Easy, boy.

"Now don't get too excited over this yet, kiddo," she sneered. "You'll have to earn them. I know just the gas station where we can turn this into a little exercise for you."

A little exercise? Now, what did that mean? I wasn't able to place the amused expression that was written all over her face. Was she making fun of me or just looking at how I was gonna react?

“Don't worry, Jackson,” she calmed me, tousling my hair. “You'll do just fine Don't think too much about it.” She let go of my hair and after taking a sip of her coffee added, “So let's go back to work for an hour or so. We have the whole afternoon to go to the gas station.”

With the prospect of engaging in another exercise, the last bit of tutoring for the day passed by in a rush.

After lunch, when we had arrived at the gas station and parked our bicycles, Emily kept me from entering the shop.

“No, not like that,” she began, running her hands through my hair to put it in better shape, then straightening the collar of my t-shirt. “There. That's more like it. Now go in and get the condoms I told you. I know the cashier. She's a girl from school. She's cool. Nothing you couldn't handle. And make sure you flirt with her, okay?”

The chime rung when I entered. I threw a glance at the register—no one there. Just a pack of rubber. Nothing special. Everyone does that, right? Should I buy some other stuff to cover up? Nah, don't be pathetic! Man up for Emily! You can do it! Just the condoms. Just take a deep breath.

My eyes looked through the different brands for the right product. Who would have known this would be so difficult? Come on! How hard can it be? Just take what you need, pay and leave. Piece of cake, right? That's how it worked last time. Yeah, but I didn't have to shuffle through all these packs because it was at a frigging vending machine. No one to talk to, especially not a female cashier. That's what she said right? Oh my god, what is Emily making me do here?

My heart almost stopped when I heard the door chime ring once again. With my eyes transfixed to the dude stepping to the register to pay his filling, I hoped—I prayed—he wouldn't see me still standing there, unable to just grab a pack of condoms like the inexperienced kid I was. I heard him chat with the cashier—when had she shown up? What was I still doing here? For fuck's sake, how can this be so difficult? Do it for Emily, you wimp!

The moment passed by with him leaving, not even acknowledging my presence. Thank god! I swallowed hard despite my mouth being bone-dry, picked the pack of condoms and headed to the cashier—a girl a little bit older than me, probably. Just as Emily had said. A really hot chick. Her uniform just that one size too small that made her tits press against the button-up shirt enough so her hard nipples gave away she was going commando. Eyes green like a pine forest and lips just made for sucking dick, naturally forming a welcoming pout. Hidden behind the counter, the rest of her body was but a guess I could place.

Her eyes seemed to light up when she saw the only item I held in my hand, yet we only had your usual customer-seller chat. At least until she handed me over the change. “Thank you for choosing us and... have fun, handsome.”

Her wink almost made my heart melt then and there. “Th-thank you,” I barely managed, then, gathering my courage and swallowing my teenage nervousness, added, “I will.”

She bit her lower lip and replied, “Too bad. I hoped I was gonna get my share of you too.”

In a fraction of a second—which foremost surprised myself—I leaped over my shadow and decided to take the bait: “Who says it wasn't you I was referring to?”

Where did that just come from?

She chuckled playfully and shot back, “I see her waiting outside.” She paused for effect. “Good catch, lucky boy. Take good care of her. And should she ever dump you, you know where to find me. I'm a good listener, you know?” She accompanied her last remark with the internationally acknowledged, unambiguous blowjob gesture.

Hearing her say I was caught, my face turned beetroot red. I grabbed my acquisition, turned around and quickly stepped to the exit while I heard her giggle from my incautious flirt.

Emily had the biggest smirk on her face when I came out of the store. “That was fantastic, Jackson!” she commented on my failed attempt at talking to the cashier. “That reply was killer! And you said you needed my help in talking to girls? Who are you kidding?”

I tried to stammer something as if I had been caught red-handed. Well, I had, hadn't I? “I... uh... oh... you were listening?”

Emily took my face into her hands and looked into my eyes. “Of course, I did. I'm supposed to supervise you, dummy. I'll be honest with you. Your flirt was so straightforward I got jealous of her. She wanted you so bad. Just the way she looked at you. And look at her. She's a perfect ten. There's everything about her to be jealous of.”

I wasn't exactly sure where she was getting to with her rant—if this even was a rant, that is—for the tone in her voice seemed all too exaggerated.

I decided to probe the true nature of her obviously feigned jealousy and interrupted her, “...says the girl who could easily pass as the Hustler cover model. At the risk of sounding cheesy, nothing compares to that expression so full of life in your eyes when you're happily smiling.”

“Wow, Jackson,” she sighed. “Where do you always take these compliments from? I'm turning to silly putty here.” She kissed me tenderly, letting me know she had dropped all her jealousy.

When we parted, she added, “Guys have complimented my eyes, sure but just to get into my panties, mostly. Now, this compliment was something entirely different.”

I playfully hit her waist. “I learned from the best,” which earned me another peck and an 'oh you' before we mounted our bikes and cycled back home again.

Once again, we spent the better part of our lazy afternoon tanning in the sun in our swimsuits—or better: we wrestled, made out and fooled around in our fresh love. I was on cloud nine, in the bliss of my teenage hormone-drunk devotion for Emily.

All of a sudden, the doorbell rang and Emily almost jumped to get the door. Intrigued by her actions, I followed her but she had stepped outside and left the door only slightly ajar so that I could only hear fragments of her voice and almost nothing intelligible from a distantly familiar male voice. Where had I heard this voice before? It seemed to ring an all too far away bell.

I heard her giggle and say, “Thanks, dude. See you soon,” before she stepped back in and handed me a sturdy package which I identified as a sixpack of beer cans. “We're gonna need this tonight.”

Dumbfounded, I looked at her, at the beers, at her again, closed my gaping mouth and lifted a questioning eyebrow. “And what would these be good for? And who was that at the door? My parents will so kill me if they find this out.”

“That was Brett. The dude who was supposed to give us a lift home from that disastrous party. Remember? He got me the sixpack. Has an older brother who does that for little pleasantries,” she beamed. “Got us drunk more often than I remember.”

“What type of little pleasantries,” I inquired, not liking the timbre in her voice when she spoke of him.

“Oh, you know,” she began, curling a strand of hair around her finger, giggling coyly and avoiding my gaze. Upon seeing the mix of insecurity and jealousy distorting my face, she started laughing and explained, “You should see your face. I'm kidding, cutie-pie. He gets us booze, we give him some of Jenny's weed, is all. Sometimes, he does get lucky with one of us but I'm way too much of a grind for him. He likes dumb girls, you know. Gentlemen prefer blonds if you get what I mean.”

I swallowed my shame from having suspected her to be unfaithful and apologized, “I'm sorry, Emily, for thinking so bad of you.”

She ran her hand through my hair and caught my elusive gaze. “It's very considerate of you to apologize, kiddo, but there's nothing to apologize for, really. I teased you in a way I shouldn't have. You have every right to be mad at me. I do agree, though, that in a relationship, trust in each other is of fundamental importance. Also, you should never be jealous of your girlfriend's ex-boyfriends. There's a good reason why they are ex-boyfriends and not current boyfriends, okay? Of course, you will get compared at first but you'll compare them with your exes just the same, trust me. And just let me tell you something, Jackson. You might not be of much use in bed yet—“

(Now honesty is nice and all but that was a punch straight in the guts. Just wanted to say this here.)

“—we'll get there, don't worry—but despite being my youngest boyfriend, you're the first who's best understood what a girl needs and wants to hear. For starters, you treat me like a human being, you know, and that's hard to come by.”

I swallowed hard after hearing her elaborations. “Emily, I... Wow, that was...”

“It's okay, Jackson,” she resumed her speech. “Now, let me make this up to you. I mean, getting you jealous and all. The beer is for dinner and supposed to give you a bit of a buzz. That too will help you last longer—just like the desensitizer in the condoms. Now, I didn't say I wanted to get you shitfaced, just a bit tipsy is all.”

“...and that answers my other question,” and means I'll get some more action tonight, I thought to myself, trying to keep this greedy, anticipating expression from creeping over my face.

“Yeah, I need to get laid properly and you're gonna help me with that,” she proclaimed, winking at me. “So what's for dinner, hun?”

“I, uh, I'm gonna check the freezer. Wanna tag along?”

“There's nothing quite as sexy as a freezer full of food, is there?” she teased.

“Ours is always pretty stuffed so the perfect asset should I ever want to date a cavewoman and show her my prowess in providing nutrition,” I nonchalantly shot back, walking the stairs to the basement.

“Did you just call me a cavewoman?” she asked, an explicit irritation in her voice.

With a grin all over my face, I replied, “Oh, I'd date you even if you were one.”

Laughing heartily, she said, “You really do dish out the silliest compliments, don't you? You know what? Making girls laugh is crucial. The spasms of the diaphragm increase the blood flow in the lower abdomen and since that's where the honeypot is, it also increases the production of vaginal fluids. In layman's terms: laughing makes girls wet. That's why guys who keep cracking dad jokes all the time are perfect husband material.”

Not having expected this open description of how to get her to bed, my self-content faded and I felt the heat rise in my cheeks although I was standing in front of the open freezer in just my swimming trunks. She, visibly amused by my dumb expression, browsed through the drawers.

“Here, catch,” she said, throwing something in my direction. I was barely able to catch the frozen snickers bar. “You're so cute when you lose your cool.”

“Oh yeah?” I replied, gathering my boldness again and shoved the snickers bar between her breasts to which she jumped in shock.

“Nice one,” she said, slowly sliding the bar up and down between her breasts after regaining her composure while I just swallowed from her ability to just ignore how cold that thing was. My girlfriend was such a badass!

She took the bar to her face and seductively ran her tongue over the wrapper. “Feels nice,” she moaned, “but that's not the place to put this. Wanna know where you'll find the right hole?”

She approached me while putting back the snickers bar and kissed me deeply. Soon our tongues were dancing and our bodies melting into each other, hands roaming over each other's backs and a full-scale foreplay going... until the freezer's overtemperature alarm went off.

Panicking, I gave out a 'fuck' and shuffled through the drawers to find what I was looking for. “How does lasagna sound?”

“Awesome,” she replied with glistening eyes and watering mouth—not sure if from the sizzling hot make-out session or if from the prospect of getting the world's best lasagna (Mom's) for dinner.

I pushed close the freezer door and threw a “will you shut up, already” at it.

When I had put the lasagna in the oven and set the timer, Emily planted another hungry kiss on my lips. “That was hot down there. I got an idea. Why don't we eat in front of the TV? You unlock one of these X-rated channels again to get us in the mood. How's that sound?”

“Hell yeah!” was all that came out of my teenage mouth.

“Attaboy!”

I rushed to the TV and did as told. While I was zapping through the channels that mostly showed ads for overpriced phone sex, I heard a distinct noise of two aluminum cans getting cracked open and the overpressure leaving them. I looked to Emily who was holding two cans of beer and handing one to me.

“Did you really just open both of them at the same time?” I asked, wondering how this was even possible.

“Sure. You just have to take them by the top and slip your middle finger under the tab. Hold it well between your four other fingers and crack the can open. Just keep in mind that when the overpressure leaves, the can gets soft and you have to hold it well, otherwise you'll drop it and spill everything. It's easier if you do it on a table. Takes some exercise but works like charm once you get the hang of it.”

“I really have the coolest girlfriend,” I said, my expression filled with sheer awe.

“You're just too cute,” she replied, toasted with me and kissed me before downing three generous sips of the fermented hops broth.

Finally, we found the first channel with some real action going on. The scene was in full swing and showed a dude pistoning his dick in and out of an obnoxiously moaning fake-tits, fake-lips brunette's ass.

“Wow, look at this,” Emily said with amazement. “That dude's like clockwork. Zero emotion. Just getting the deed done.”

“And did you see his size?” I commented too. “That schlong is monstrous. That's gotta hurt like hell in that tiny hole.”

“Yeah, but look at her. She's totally digging it—or gets paid to act like she did, anyway,” she completed the description. Then, turning to me, asked, “And you? What do you think of anal?”

My eyes still glued to the action on screen and too absorbed to really think about what I was saying, I replied, “Not much. Alright, I enjoy watching it on screen from time to time but sticking my dick into a hole where poop comes out? No way! And you?”

“Well,” she chuckled. “I tried it once. We were drunk and my boyfriend of the time oopsed it into the wrong hole—as if that were possible. He still claims it was by accident. Accident my ass—literally. It was so incredibly painful but over soon since, drunk as he was, he snapped his banjo string while trying to shove his needle dick in there. Long story short, I ain't gonna take no dick up my pooper for the next twenty years or so.”

“Needle dick? That's a nice one. I'll have to remember it,” I laughed.

Emily bit her lower lip and slowly crawled over to me, strategically placing one hand on my upper thigh. “You know, compared to yours, every guy I had so far had a needle dick.” She said this with a low, sexy voice, making my already hard cock twitch and grabbed it through my loose trunks while nibbling on my neck.

I gasped in pleased surprise from her nonchalant, bold touches. When her kisses finally reached my lips, my hands found her bikini-clad breasts. I was delighted to be reminded she had removed the push-up padding. Unfortunately, by the time, she was lying on me with her full weight and we had resumed our previously interrupted foreplay, the oven timer went off.

“Just when things were getting interesting,” she sighed. “But, yeah, I'm starving.”

I downed the remainders of my beer can and nodded absentmindedly, my eyes transfixed to the TV. I was already starting to feel the effect of the beer on my empty stomach.

While eating, Emily complimented my Mom's lasagna and how it was even better than she remembered. I kept working on my buzz and, cracking open my third beer, I re-evaluated how much of it I should really drink and, not wanting to ruin the night again, decided to go slow.

This, however, didn't prevent me from talking more quickly than my brain followed. “For tonight,” I began, then took another small sip of my beer. “Uh... do you... er... want me to... um... eat your pussy? I mean, well, uh... You know.”

She silenced me with a love-crazed kiss. Looking deep into my eyes, she replied, “Of course, I'd love you to give me head, silly. It's what every girl dreams of. But if you don't want to, I mean, if you find it gross, you don't have to. Many guys find it gross, you know.”

“Yeah, but...” I gathered my courage. “You sucked me off yesterday. Don't I, like, have to go down on you? Like, you know, to get even with you?”

“I like your thinking, kiddo, I really do,” she retorted, her clement, understanding smile on her lips. “I sucked you off because I wanted to, okay. I cannot make you do things you don't want to. Same goes for you. You cannot force a girl to anything. You can ask her to do things to you but you'll have to accept a no as an answer. A no is not an offense to your ego, it just means she's not into whatever you're asking her to do. You can try to convince her but never beg or whine. Now, just the same, I'll ask you to go down on me but you don't have to if it grosses you out. I can only encourage you to try it, okay?”

I swallowed hard as if I had just received a monumental scolding on my conduct. In fact, she had just taught me an invaluable lesson about how important consent was also in the little things which might seem unimportant at an inconsiderate teenager's first glance.

“Please teach me how to eat pussy,” I said with a cracking voice, my cheeks hot as a red-glowing iron. “I wanna make you scream my name.”

She ran her hand through my hair and kissed my cheek. “You're a real cutie, aren't you? So let's just put the plates in the sink and hop in the shower. I'm not gonna make you eat a pussy that tastes of day-old piss and sweat. We still have plenty of time to discover each other's fetishes if an unwashed pussy is what gets you off.”

After a quick and uneventful shower—save for resuming our repeatedly interrupted make-out session under the running water—we went back to my bedroom where she removed her towel and threw herself on the bed to lie on her back, legs bent and spread, presenting me her squeaky vagina and her arms reaching in my direction as if to welcome me into a naked hug. I drank in the sight of her perfect beauty for a second or two before I loosened the towel around my waist, freeing my rock-solid cock.

Her eyes grew the size of saucers at the sight. “I'm still amazed that a boy your age is capable of sporting such a big tool there. Mind if I suck you a bit before you go down on me?”

Was that a serious question?

I stepped to her with my hard-on rocking to and fro with every step. She adjusted herself to sit on the bedside and leaned forward, grabbed my cock and planted a soft peck on the tip. With one hand, she slowly pumped the skin back and forth while gently placing her lips just around the very end of the head. Her full lips kissed and sucked on my mushroom and I started to moan. I threw my head back and enjoyed the sensation of her lips closing a ring just at the base of the head and her tongue lapping the first drop of pre-cum that was already forming.

She started slowly bobbing her head up and down, taking in more of my shaft into her mouth with every repetition while lowly humming a melody on it. I was in heaven. When she had almost reached the base, she took one deep breath and deep-throated my entire length. She held me there for a short while and I could feel her swallow with my length down her gullet, giving me sensations I had never felt before.

As she let go, a sticky rope of saliva hung between her lips and my cock. She caught it before it fell on the bed and rubbed it over my dick, pumping it until it was glistening with her naturally lubricating oral secretions.

“Your turn,” she whispered lewdly and turned around to lie on her back again.

I climbed on the bed and lay down on top of her. I began a trail of kisses at her ear, went down her neck, her collarbone, further down between her breasts, held one of them in my hand while I circled the other with more kisses, gave the nipple one soft peck and went further down to her navel. I shifted my body down between her legs, still inching my way down with my lips locked to her soft skin. When I reached her mound, I looked up and searched her eyes for advice.

She asked me if I had enough space and repositioned herself to grant me more room.

“Now part those lips down there.” I did as told. “See the glistening trail that comes from the entrance? That's you who did this.” Major ego boost! “Now starve me out for the touch of your tongue. Don't go straight for the clit. Keep me hooked. Torture me. Deny me that sweet sensation. Just kiss and lick my crotch right outside the lips. Don't go between them just yet. Make me squirm and beg for it.”

Eager to follow her instructions and fulfill her wish, I let my tongue slowly run over her swollen outer labia, feeling how the skin tissue was soft and gave away under the gentle pressure of my tongue like a warm pillow. I traced the outline of her pussy up to her mons where I place a kiss and down the side of her opposite pussy lip I had so far neglected. When my tongue came dangerously close to what I suspected to be her clitoral hood, I heard a lust-filled gasp emanate from her mouth. Every time I brushed near that specific spot, her sighs would gradually turn to a frustrated yammering.

By the time I allowed myself to brush her inner lips, I felt her hips squirm and buckle against my touch, seeking the right angle to make my tongue touch her clit. Her sighs turned into a painful whining when she wasn't able to adjust her body to have her most sensitive spot meet my tongue. The more she moved, the more she smeared her abundantly flowing juices over my chin.

Instead of granting her the much-needed release, I delayed it further by dipping my tongue into the tunnel from where her nectar sprang. She placed a hand above her clit and separated her pussy lips to display her engorged button.

“Please, Jackson, suck my clit,” she purred painfully.

She had asked me to make her beg but this was all I could bear, given my inexperience. At the mere touch of my tongue on her clit, her body spasmed in pleasure. A few gentle flicks and I felt a surge of her lust hit my chin and trickle down my neck. She yelled out in lust the sweetest cry my ears had ever heard. Not sure of what to do, I kept licking her clit as gently as possible with the writhing of her body until she closed her thighs to escape my touch.

When she spread her legs once more, her cracking voice demanded, “Do it again and put a finger in my pussy while you're at it.”

The moment my lips re-connected to her nether lips, her voice picked up the previous moaning and her body started to tremble again. When my finger slid into her slippery tunnel, she screamed anew in an even higher state of bliss. Like before, I tried to keep my mouth connected to her pussy while I ate her out as if I was making out with her.

“Did you come?” I asked in a brief supçon of teenage insecurity when she had calmed down. Call me Captain Obvious but what idea did I have of a genuine female orgasm?

“Twice,” she gasped between her labored breaths. “And if you want to make me come a third time, suck my clit between your lips and bite it gently.

I didn't need to be asked twice. I practically threw my face into her crotch again and started devouring her clitoris just as she had asked me to. Before I realized what was happening, I had to cover my ears for her screaming that was reverberating from my bedroom walls was louder than my hearing could take.

Grinning like a village idiot and my face marinated in her vaginal secretions, I crawled from between her legs to get on top of her. Her face was flushed, her hair disheveled and she was still catching her breath when I kissed her. Her lips were just as soft as her labia as they sucked in my tongue like a hungry feline devouring her prey. The thought of having her lick her own juices off my face had me so horny I only realized I was rubbing my cock against her crotch as I noticed how slippery her slit was and how much this made me want to fuck her brains out.

She broke the kiss to order, “Fuck me silly. Please fill me with your dick.”

I unpacked a condom as adroitly as my slick fingers allowed which was rather on the clumsy side of the term. I noticed there was, just like Emily had stated, some colorless gel in the tip, which was supposed to make me last longer. It took my untrained hands some effort to overcome their gaucheness in rolling the condom all the way down but as she had predicted, due to the larger diameter, it went a lot easier than the night before. This time, however, much to my delight, I didn't ejaculate. Complete success! Mental fist bump!

So far, everything went well. And now for the main act. I positioned myself between Emily's legs and aimed for her love tunnel.

She, nonetheless, prevented any intrusion by blocking the entrance with her hands. “No, not like this, Jackson,” she explained, being her tutoring self. “Let me handle this.”

She told me to lie on my back. Then she straddled over me and squatted over my lap. With her hand, she guided the tip of my cock to her entrance. Slowly, she sat down on it, letting me feel how the slippery, fleshy walls made way for my shaft to hug it tightly. Once all the way down, she didn't move for a while, allowing me to adjust to the sensation of her warm pussy clenching around my entire penis.

“Now it's my turn to make you feel good,” she purred, starting to gyrate her hips with my sex deeply embedded in hers.

Now it was my turn to throw my head back in pleasure and moan with every touch, toss and turn of her pussy that hungrily feasted on my cock. With my hands on her hips, I supported her movements.

She took my hands and placed one of them on one of her breasts that wiggled every time she drew a new circle with her hips. The other hand went to her face where she took my index and middle finger in her mouth and sucked on them while looking into my eyes. Her sultry look made me buckle my hips up and down to meet her every motion.

Soon, she was heaving her ass up and down while I thrust my cock into her from below in resonance to her periodic movements. Every time her ass hit my loins, a slap echoed through my bedroom along with a staccato of two dissonant voices in pleasure.

When we slowed down, she bit her lower lip and asked, “Do you want to feel me come on your dick?” I nodded eagerly. “Thought so. Brush your fingers over my clit and I'll get there in no time.”

Just as she told, as soon as my thumb found her button, her body began to shiver again and before long, incontrollable spasms ran through her body along with her vocal expression of her climax. I felt her pussy convulse on my shaft as if tried to squeeze out all it may offer but nothing came. In combination with the beer-induced buzz, the desensitizing gel in the condom I wore seemed to work wonders on my stamina.

Emily was lying on me, panting, my cock still buried in her. She hugged me in a loving embrace. Her mouth right next to my ear where I could hear her labored breathing as she slowly recovered from her orgasm—her fourth orgasm, note well. Not bad for a sixteen-year-old boy, was I?

She sat up again, giggled girlishly. “Look at how good you've become in just one night, my little stud.”

Her beaming smile made me gasp. I realized the pure beauty of this image: her, exhausted from her repeated orgasms, content from sexual fulfillment—the picture completed by my cock entrapped in her walls of warm, moist flesh. Perfection!

“Those condoms are magic. You still didn't come?” she asked to which I slowly nodded, mouth agape from the sights I was drinking in. “So let me give you something in return for those orgasms.”

She dismounted me, turned around, got on all fours and, sticking her ass up and resting her upper body on her shoulders, she reached behind to spread her ass cheeks, displaying her soaked pussy. She, exposing herself in such a lewd way, made me swallow hard.

“What are you waiting for? Ram that rod in there and make me feel your dick pump your seed out,” she ordered.

No more command was needed. This time, I allowed my teenage urges to guide me. I simply shoved my dick back into her inviting hole and began pistoning in and out of her similarly to the porn flick we had watched during dinner. This had nothing to do with love; it was just the mere quest for my own satisfaction without a single thought wasted on her pleasure. She encouraged me by reaching between my legs and massaging my balls with her hand.

The combined stimuli of her snatch clad around my dick and her hand on my balls send me over the edge just a few thrusts later. My grunts timed with the spasms of my pelvis, I emptied my load inside her—in the condom.

I collapsed, rolled aside and, out of breath, came to lie on my back. Emily crawled to my side and cuddled up with me. She lay her head on my chest while letting her index run over my torso.

“So how was your first time, big guy?” she asked, looking up at me with puppy eyes.

My head was filled with inappropriate expressions. Sure, I was a stupid teen. But, like, 'that was awesome' or 'that was total killer' or yet 'that was yeet' just didn't feel like the right words to put it. 'Babe, you made me feel like a real man, like a million dollars.' Seriously?

“That was...” I began at a loss for words, “...just wow. Indescribable. I can't put it into words.”

“...and how does it feel to have lost your virginity?” she kept probing.

“Well, uh, to be honest, I, uh, don't know, really. It's not that much different than before, you know,” I evasively blurted out, not knowing what to answer.

“Not much different? Will you listen to yourself, young man! I just got the best fuck of my life—by a virgin teenage first-timer, note well—and he goes like, 'yeah, nothing special, I do that before breakfast.' What the fuck, kiddo?” she ranted, a playful chuckle in her voice.

Dumbstruck, I had no idea what to reply not to make the situation worse.

“Just kidding, cutie-pie,” she giggled. “I know exactly what you mean. Losing your virginity isn't all it's cracked up to be. You're still the same person afterwards. But still, you're an awesome fuck, Jackson. I mean it! You can be proud of that.”

“Come on, you're just saying that. And even if... No wonder! You told me exactly what to do and I'm sure I'll get a lot better once I get the hang of it,” I sheepishly shot back, embarrassed by the unexpected compliments.

“I mean it, Jackson. Sure, there are some kinks and nooks here and there but all in all, you were my best fuck so far,” she stated, making my astonishment greater. “For starters, you're the first dude who cares about my orgasm. Huge plus! Second, you listen to what I tell you. You have understood that sex is not about you alone. That's an asset, believe me. Girls dig guys who make them come.”

Proud of my latest exploits, I pulled Emily closer to me and enjoyed the feeling of being a real man this gave me. For that brief moment, I felt like the king of the world and that anything was possible.

After a while, when my cock had shriveled up to its habitual, unimpressive weenie-like appearance, the rubber was starting to get very uncomfortable so I removed it and disposed of it. Still being too excited to sleep yet, I cuddled up to Emily's side. She wrapped her arm around my shoulder and made my head rest on her soft breasts just like the night before.

The sound of her heartbeat reminded me I had to savor this moment while it lasted. Only another ten days and my parents would come back... and she would have to leave—leave both this place and me. Instead of feeling sad about it, an emptiness crept into my belly. I knew I had no right to ask her to stay, I was aware of it, I understood it, but that was still ten days ahead of us. This meant ten days of dancing on the bliss of fresh, young love with rose-colored glasses on before the shattering soberness of reality would catch up with us.

I snuggled deeper into her pillowy breasts and held one arm on her belly. She responded by pulling her embrace closer. We kissed and when we did, I felt the anguish in my chest make way for a lightness that soon replaced all my demons.

When I looked into her eyes, an urge from deep within me overcame me, and without thinking twice, I started, "Emily, I-I-I–" but before I could finish my stuttered three-word sentence that would have expressed the feelings I had for her, she silenced me with her index on my lips.

Her eyes were glistening with both joy and tears when she spoke with a shaky, cracking whisper, "I know, Jackson but please don't. As much as I'd prefer to reciprocate your words, I can't—I shouldn't—and you know that. It would make things only very difficult and painful next week. Please understand, Jackson. It will hurt enough just like this to leave you."

I knew her words were sincere. I knew from her voice that she would be overjoyed to hear me say it but, alas, she was right. With this in mind, we slowly drifted into a long, deep slumber from which I awoke with a determination.

I wanted to enjoy and savor every minute of our intimate togetherness. I gave my best at listening to her, following her advice, getting to know every aspect of her—her imperfections too. Despite the many times we were painfully reminded of the fugacity of our little, yet unfathomably significant summer fling, our time together, for a very brief instant, seemed to go on forever. In our ephemeral, yet deep love, we tried to put every moment to good use and to make the best of the scarce time that became inexorably less with every second.

During that time, Emily taught me two invaluable lessons: first, how to apply myself and to exploit my potential—be it for my educational career or in matters of love; second, how to talk to girls. It was just as she had said the first day of her stay: girls are just humans too. I was fully aware that I would owe her the better part of any of my future achievements.

It was only on the very last day when I got my Mom's text about my parents' estimated time of arrival when it dawned on me we were about to break up. There is a first time for everything and this one first time was a remarkably dolorous one. Not only was I about to let my first girlfriend go to college, I was about to lose the first girl I would have declared the love of my life at my very tender age. I owed her everything and she was about to leave me just as we had agreed; just like that.

Both of us packing Emily's suitcase, the afternoon of that Saturday came before we even noticed. I had to fight off my tears when she folded the bikini she had bought on our first day together and saw she too was struggling not to start crying. She looked into my face as if she was expecting me to find words to ease the grief.

We were doing the dishes of our last lunch together when we heard a car roll up our driveway, a motor shut and the characteristic thud of two doors. Soon thereafter, the front door flung open and in came my parents.

My mind was too absorbed by the imminent departure of Emily to really grasp the moment. The cheery questions, inquiries and narrations passed by my ears without me even paying attention to any of them. All that mattered was that I was about to lose Emily and before I could gather any coherent thought again, another car stopped by our house—Emily's dad.

He stepped out of his car for a quick chat and thank yous for my parents' generosity but nothing more. To me, the situation appeared surreal. In a way, my parents were paying Emily to leave me and go far away from me. As absurd as the thought was, I couldn't shake it. It made my stomach churn and left a bitter taste on my tongue.

The formalities were over quickly and after those, he did what he had come for and took Emily with him. A few more words of gratitude towards my parents and a hug with me that told volumes about her sorrow, accompanied by a promise to drop by to exchange proper farewells and that was the end of it.

With that, she left our home. Emily's dad revved up the engine, one last exchange of words and waves; an awkward smile and off they were. Just like that. All we had worked on and achieved gone in the blink of an eye. At least we had kept our promise to renounce a dramatic farewell scene.

I sighed heavily. My dad padded me on my shoulder like dads do with their sons and asked me if I was relieved to have survived two weeks babysitting. My answer came with a blunt 'yeah' and a forced chuckle.

I excused myself to my room on the pretext that I needed a quick nap. Of course, Mom teased how exhaustive teenage girls were. I set up my best good mood mask for her shallow joke while deep inside, I was already feeling my heart crumble.

I rushed upstairs to my room. As soon as the door was closed and locked, I burst into tears. I didn't even make it to my bed; they just seemed to keep popping out of my eyes from alone while my body writhed in agony over the loss of my first true love. Although just brief, I was just beginning to realize how much affection, energy and effort I had put in our relationship—she had put in my education. It dawned to me how deeply I had fallen in love with her and that our relationship, however intense it had been, was but a daydream that had been washed away like a sandcastle in the rising tide.

For half an hour, I cried my eyes out until I fell into a dreamless sleep from which I awoke lying in bed with no memory of how I had ended up in there. Once I had reoriented myself in my room and checked the clock which said Sunday morning, seven sharp, out of recently acquired habit, I let my hand feel around for Emily. It took me a while until I remembered she was most likely lying in her own bed at that very moment. Immediately, I felt as if someone had punched me in my guts. I suppressed a surge of renewed tears. I needed a distraction, quick, so I decided to set up the table for breakfast and set up some coffee.

Upon seeing my efforts, Mom unknowingly teased she should have thought of hiring a babysitter earlier. Little did she know her words stung like needles to the already torn shreds my heart now consisted of.

During the last few weeks of summer vacation, I did my best to distract myself from Emily. I was helping my parents wherever I could, went to the groceries, read actual books—schoolbooks, even—tried to finish some of Dad's procrastinated bricolage, just anything to keep my mind busy. Still, I cried myself to sleep every night. I was moping, mourning a loss far greater than what I had so far experienced.

Although my parents didn't act like it or ask, I was pretty sure they felt something was afoot. They were unusually comprehensive for my little teenage outbursts I tried but often failed to keep to myself.

Sure, I could have called her but I didn't have her number. Asking my parents? They wouldn't believe me. Also, it would have made things a lot more painful than they already were, however strong the urge to hear her voice again was.

The weeks crept by slowly and by the last holiday weekend, I felt unusually relieved and eager to start school again. I was looking forward to adopting my old routine I had once questioned the use and meaning of. Over these last couple of days, my sadness had gradually turned to frustration. Hadn't Emily promised to drop by to give me her proper farewells as she had phrased it? Had she already forgotten me? Was I just one of her infamous conquests? Or worse: just another good guy?

These questions had been gradually wearing me down over days. My heart was alternating between depressing sadness, irritating frustration and anger at her for treating me like the little boy I was. In short: I had the blues. How had I been so foolish to think she could fall for me? Me, the awkward, little sixteen-year-old brat. That's what you get for being so blue-eyed. She had used me, so much was for sure; for LOLs and giggles as she surely would tell her friends. Bitch!

That Saturday morning when I got the mail, I noticed an unstamped envelope that only had my name on it. With a certain presentiment, I rushed to my room, my heart pounding with adrenaline and my brain going ballistic with weeks worth of dopamine rush.

I practically tore the envelope apart to jerk out the folded paper and read the handwritten lines in a hormone-drunk frenzy. I had to read the letter several times before I was able to control my emotions and focus on the text, let alone understand it.

Dear Jackson,

The time has finally come. I'm setting sails for college. This means farewell. I promised I'd drop by to give you my proper farewells and see you one last time before leaving but I just couldn't bear to look you in the eye. My inability to see you in person breaks my heart but I had to face the ugly truth. These two weeks with you have truly turned my world upside down and the three weeks thereafter had my mind spinning with thoughts of you and my heart aching to pull you into our familiar embrace once more. It took me a while to accept it—and I still find it difficult to fathom—but I must realize I have fallen madly in love with a sixteen-year-old boy.

Yes, Jackson, as absurd as this may sound, I love you. It shatters my heart to leave you like this, yet my courage fails at the mere thought of seeing you and giving you my goodbyes. The adventure you and I shared could have been so much more than just a mere summer fling. Alas, it is my time to turn the page and head forward towards the next part of my life while your place, for the time being, is here. While you'll keep applying yourself, I will keep you in my heart in hopes my thoughts may help you on your way and I might see you again. Until the time of reunion has come, promise me to make good use of what I've taught you and you'll find a girlfriend with ease, even if this means I cannot have you. The thought alone of this makes me jealous of whomever you might take to be at your side, yet I am fully aware of the role I played in your education in this regard and I will be proud of you, no matter who you choose.

Farewell and don't forget me.

In deepest love,

Emily

PS: Here's my number. Hit me up when you've graduated *wink*

PPS: Make sure this bitch Sarah realizes the mistake she's made by ditching you. You deserve better.

My heart sank—or rose? I don't know exactly. I was overwhelmed by all kinds of emotions. I felt my heart being torn between relief, sadness, happiness and yet hope, mostly. For the first time in weeks, I managed an honest smile. Emily was right. Despite the unreachable, unimaginable love we had shared, I felt ready to begin the three-year adventure until I would see her again. I was confident that, with what she had shown me, taught me, I was primed for whatever may come.