#HI PILF I HOPE YOU'RE WELL | Explore Tumblr Posts and Blogs

sinsiriuslyemo · 6 years

Note

Hey if you're still taking requests, can you an older man/younger woman imagine with Jackson where she's a little inexperienced in the bedroom and he teaches her how to really please a man? And all the while he's very attentive and supportive and loving lol

Delia,

I am so sorry this took so long (I’m also still working on the Nevada request you sent, so be on the look out for that one) but I think considering the length of this one, you’ll be happy. At least I hope. I didn’t mean for it to be this long, but this is easily my longest imagine to date at 7400 words!! AHHH!!! No pressure to make this length the new standard, guys lol

I’m pretty proud of this one, though, to be honest! I hope you like it!!

Sinceriously,

Hero

Upstate New York in the summer time could be close to unbearable. Not nearly as hot as it could get in the city--thank God--but hot enough to make you wish it were fall already. Then there were days like today, where even though the sun took no mercy to hide itself for a while so that the temperature would drop, a cool breeze counteracted it’s blazing heat. It was days like today that you decided to read outside at a picnic table, which sat beneath an oak tree before your first class. You almost always had a book in your hand--something you’d picked up around five years old.

You always prided yourself on your intellect and your willingness to learn about all sorts of subjects. From the histories of ancient Rome to spending countless hours trying to prove the Continuum Hypothesis--despite the fact that no one in history had ever been able to prove or disprove it--you thirsted for knowledge about anything and everything. You were an overachiever, a scholar; everything you set out to do, you perfected and did so with pride. Why then, were you so intimidated by learning about sex and men?

You weren’t completely naive, but were what most people referred to as a late bloomer, and it had worked out well with regard to your studies. No one ever bothered to ask if you wanted to come to parties or football games and none of the boys you’d gone to school with had ever shown an interest in you past asking to copy your homework. Things remained that way in college as well--education had always been of the utmost importance to you. The male species had quite simply never interested you, not even the intelligent ones.

That is, until you met Dr. Jackson Neill, your professor for Religion and Popular Culture, which you’d opted to take last semester in order to satisfy an elective requirement. You had overheard several of your classmates who had taken his class talk about how “dreamy” he was or how he was a “PILF”--whatever that meant--but never did you expect that you would find him attractive. It was primarily his mind that captured your undivided attention, he was brilliant. You often needed to remind yourself to pay attention to the lectures instead of fantasizing about you and he having a heated debate over where religion ended and pop culture began. The fantasy often ended with his hands mapping out every contour of your body while naming each of your bones as his long fingers traced over them.

You had been thrilled when he’d taken an interest in you, asking you to stay after class to discuss a paper you’d written that he wanted to publish, or to recommend a new documentary he’d seen over the weekend that he thought you might enjoy. You knew in the back of your mind that there would likely be nothing between you. Afterall, he was your professor, you were his student. To become involved in a sexual or romantic relationship with him would be unethical, and was severely frowned upon by the university. Still, you appreciated every moment you’d had with him, and he seemed to enjoy your company as well. So much, in fact, that he frequently emailed you, even after you’d passed his class eight months ago, just to tell you about a book or article he’d read that he thought might interest you.

Despite your desires, you tried not to read too much into it. Perhaps he had an interest in mentoring you and was just waiting either for you to ask him or an opportunity to ask you himself to arise. Regardless, you thought about him all the time, and lately you thought about how you would never stand a chance with him when he realized how romantically and sexually inexperienced you were. A man like him, cultured and experienced in the ways of love and sex, would never want to waste his time with someone who didn’t know what they were doing. It was simple logic.

Sighing heavily, you placed an elbow on the picnic table, and let your chin rest in your palm.

“You look incredibly pensive for it being so early in the morning,” you heard, and looked up to see Dr. Neill standing on the other side of your picnic table.

A heat crept into your cheeks as you lowered your gaze, pushing your glasses up higher on the bridge of your nose. You could almost feel his smirk as he sat across from you and swung the strap of his messenger bag off his shoulder.

“What are you reading today?” he asked, the quirk in his lips spreading to a full smile.

Jackson had noticed you from the moment you’d walked into his classroom almost a year ago. You were beautiful even behind the large, dark-rimmed glasses that always sat perched on your slender nose, smarter than even most of his colleagues, and eager to devour knowledge where you could find it. He’d immediately had a sense about you; that you spent most of your time having experiences from books rather than from life. Yet in spite of your naivety, you clearly had a good head on your shoulders. It intrigued him, inspired him to want to know more about you.

Many times he would wonder whether you even noticed men; not because you weren’t interested, but rather because he doubted the male species of the student body could keep up with you intellectually. Those thoughts typically caused him to wonder whether an older man would be better suited for your wit, which would then lead to fantasies that perhaps he could be that man.

You bit your bottom lip, and his eyes dropped to stare at the pearly white edges of your teeth pressing against the plump, red petal. A movement of your hands had him lowering his gaze again to see the title of the black book in your hands, written inside a vertical, magenta banner: The Art of Sex.

It didn’t shock him nearly as much as he’d expected, for all the knowledge you possessed and craved more of, you were human at the end of the day. Sex was a natural part of human nature and despite your primary interest in strengthening your mind with academic information, sex would inevitably make its way onto your list of subjects to study closely. However, his thoughts were far from academic with the revelation of your subject of interest. Suddenly his mind was no longer on books or conversation, nor on the class he had in twenty minutes, but on thoughts of having you, naked and writhing beneath him.

“It’s research,” you mumbled, pushing on your glasses again and avoiding his gaze.

Jackson couldn’t help the smirk that planted itself on his lips. “Research.”

Your eyes met his and your shoulders rolled back defiantly. “Yes,” you answered, trying to sound confident.

“I see. For which class?” he asked, holding your gaze as his simper remained firmly etched on his face.

Your eyes widened slightly at the challenge, and you knew lying was out of the question--he knew what classes you were taking this semester. You had told him as much when discussing the possibility of assisting him with a research project he’d been conducting earlier in the semester.

“None,” you replied. “I just thought I would learn a little about...sexual...things.”

Jackson snorted softly. “Anything I can help with?” he asked before he realized the implication.

Your pout fell open as you stared back at him, wanting to say yes so badly. You could practically taste the three-letter word on the tip of your tongue, but couldn’t get your voice to cooperate.

He stammered. “I just meant--I mean, if you had any questions or--”

“Yes!” you blurted out and held your breath as you waited for him to respond.

He nodded once. “I have some time later this afternoon.” His voice had lowered to ensure that only you could hear him as students began to litter the lawn, making their way to classes or to meet up with friends. “You could come by my office…” You bit your lip again, and he couldn’t help but add, “Or we could meet somewhere a little more private if you prefer.”

He waited with baited breath for your answer. This was a slippery slope; one lapse in judgement on his part and he could find himself having to explain to his department head why he’d tried to proposition a student. Jackson wasn’t naive enough to think that none of the faculty on campus had ever had sexual relations with a student, but he’d never experienced it first hand. In fact, up until two years ago, he’d been happily married.

“Perhaps we could meet at my place?” you suggested. “I live about two blocks off campus.”

He let out a silent breath; for someone who was inexperienced with sex and seduction for that matter enough to read a book on the subject, you seemed to do well enough on your own without even realizing it.

“Two o’clock. Just email me your address,” he said as he secured the strap of his bag on his shoulder again and stood up. He used the carrier to hide his body’s reaction to the thought of being in your apartment alone with you and smiled. “I’ll see you then.”

…

You hadn’t been able to sit still since you’d gotten home, fussing with every little detail from the shoes that had been carelessly thrown on the carpet the day before from the coffee mug that was still sitting in the sink from earlier that morning. You looked at the clock--1:45 pm.

Dr. Neill was always prompt to his classes, you knew he wouldn’t be a moment late, and while you usually appreciated that about him, now it only served to make your limbs trembled, your mouth go dry and you couldn’t stop fidgeting. The knock at the door brought your heart into your throat and you held your breath as you closed one eye and looked through the peephole with the other.

Jackson stood on the other side, looking just as nervous as you felt and your teeth caught your bottom lip as you took a deep breath, and opened the door.

His eyes immediately met yours, drifting down your frame as the corner of his lips pulled upward.

“Hi,” he said in hushed voice.

“Hi,” you replied as a tremor danced over your spine and your nipples hardened beneath your cashmere sweater.

He looked the same as he had that morning, and yet somehow different and you couldn’t place the change. The lighting perhaps? Or maybe it was the way he smiled at you now, relaxed and friendly.

You blinked, suddenly realizing that you hadn’t invited him in and shook your head as you stepped aside. “Come in, please.”

He took a careful step over the threshold, eyes moving about the room out of habit of entering someone’s home for the first time. “This is nice. How long have you lived here?”

“About three years. I couldn't pass up the convenience of being so close to campus, and the landlord has always been very gracious any time I’ve needed something,” you answered as you closed the door and pushed your glasses up on your nose.

“It’s lovely,” he replied, turning to face you and slowly dropping his messenger bag to the floor. He took a deep breath, about to speak when you beat him to it.

“Would you like to sit down?”

“Yes, thank you,” he replied, wiping his hands against the legs of his pants as he sat on the couch.

“Something to drink?”

Jackson smiled at the way you were trying so hard to be casual, as though having him in your apartment with the intention of having a conversation that would inevitably turn very sexual and quite possibly personal was a common occurrence. As though he hadn’t noticed your arousal outlined on your sweatshirt the moment you’d opened the door, and this was purely academic banter.

“Water is fine,” he answered.

You nodded and grabbed two water bottles from out of the refrigerator, bringing one over to him as you sat beside him. The gentle crack of the cap being twisted off the top of your respective bottles cut through the air and was followed by a series of deep-toned clicks as you each took sips. A heaviness settled in the air, making you wish you had decided on a different top and contradicting the goosebumps that erupted on your flesh as his eyes drifted over your form.

He was the first to break the silence. “So, I just thought if you had any questions--specific questions that aren’t addressed in the text--I’d be more than happy to answer.”

In truth he was hoping for a lot more, but he was already toeing the line; being in your apartment, after class, alone. He should be in his office, available for any student needing additional guidance with the curriculum, instead he was here imaging what was beneath your sweatshirt.

“Well, I thought I could format this as more of an in-field interview,” you answered, reaching for the Mead pad on which you’d jotted down several questions you had thought of. “Maybe I could even interview a number of men as a study group.”

Jackson felt a tension build in his shoulders as he puffed his chest out in a slow inhale. His teeth clenched briefly at the thought of you having such an intimate conversation with other men, whether or not it was strictly for research purposes.

“I would just be cautious about who you ask,” he forced himself to say. “Some men, especially the guys your age may get the wrong impression.”

“How so?”

“Well...alone in your apartment, talking about seduction and sex, can you see why they might read into something that isn’t there?” he replied.

“Oh, I wouldn’t conduct the interviews here,” you said, shaking your head. You pushed your glasses up and bit your bottom lip for what seemed like the hundredth time.

Letting out an audible breath, Jackson lowered his gaze to where the edges of your top teeth held your lip captive and licked his own lips at the thought of having a taste of the plump, red flesh.

“Shall we begin?” you asked, crossing your legs as you shifted to better face him.

“Go ahead,” he answered.

“What is typically the first thing you notice about a woman whom you find attractive?”

He thought for a moment, staring at you as the corner of his mouth quirked upwards. “Their eyes. You tell a lot about a person by looking them in the eye when they speak; their drive, their passion...what makes them tick.”

“What about sexually?” you asked, meeting his gaze again. He arched a brow at you. “There’s a difference between aesthetic attraction and sexual attraction.”

“I know that, but...there isn’t really a general answer, it really depends on the person,” he replied. “I could be sexually attracted to someone based on any number of factors; from a physical quality to an emotional one to a mental quality. It really just depends.”

“Physical quality specifically,” you replied.

He hummed thoughtfully under his breath while his eyes drifted over your frame again. “Legs.”

“Pardon?”

“A nice pair of legs does it for me, especially long legs that I can imagine wrapped around me,” he replied.

You felt a heat rush to your cheeks and your mouth went dry as you gulped, eyes fixed on your notepad where you jotted his answer down. You took a sip from your bottle of water. “What um...what is the process you experience when you’re turned on by someone?”

He snorted. “You know, something like sex and attraction can’t exactly be studied for the purposes of obtaining a universal norm. Sexual attraction, in all its complexities, varies from person to person. Take you, for example, one could argue that your intellect and innocence could be considered sexy.”

“I’m not--I mean...what is it with men and innocence? Just because a woman is sexually inexperienced, doesn’t make her more desirable,” you replied.

“I didn’t say that, I just meant that...some men might find the idea of...teaching, showing a woman how to touch him, how to please him, how to find what pleases her arousing. It has less to do with the innocence factor and more to do with the experience of...figuring those things out together.”

You nodded and pressed your thighs together as a tickle settled at your core, muscles clenching as though searching for something to grasp. Your lips parted as your breaths came slower and deeper. “That makes sense, I suppose. You still haven’t answered my question.”

He smirked and licked his lips again. “Are you meaning to ask how my body responds when I’m already aroused or what I experience as I become aroused?”

“Both?”

He gently cleared his throat, running a hand through his hair. “Typically it begins with a heat that comes over me.” Like the one he was experiencing now; he could feel the light sheen of sweat on the back of his neck and on his chest. “My skin gets hot and flushed, sometimes I sweat, my heart rate goes up and I feel this urge to touch and be touched.”

“Do you have an erection by that time?” you asked with a genuine curiosity. You’d tried to search for a video online of a man getting an erection so that you could observe that physical progression, but hadn’t had very much luck.

“Not necessarily. An erection doesn’t happen as quickly as most women believe. It doesn’t just...get hard all of a sudden,” he answered, smiling when you blushed and pushed against your glasses again. “Have you ever...seen one?” He was really toeing the line at this point.

“I tried to find a video of the process on the internet, but I wasn’t able to…” you whispered.

Jackson sighed softly as another jolt of tingles danced over his shaft, settling in his balls. “It’s fairly straightforward, to be perfectly honest. As the man becomes more aroused, blood continues to flow to that...area and his penis gets erect.”

He was choosing his words and the delivery of those words very, very carefully, but what he really wanted in that moment was to show you how incredible sex could be when it occurred between two passionate people.

“I see,” you mumbled, clearing your throat and as you shifted in your seat. There was a wetness between your legs that was making it difficult to focus on keeping things professional and the way Dr. Neill was looking at you was making your heart flutter and your breaths become labored. “How do you typically make your intentions known to your chosen mate?”

Jackson’s brows shot up on his forehead. This was by far the oddest form of foreplay he had ever experienced, but he’d be lying if he said it wasn’t just as effective as traditional foreplay. Perhaps even more, in fact, simply due to him not being able to touch you.

“You make it sound so clinical, so...calculating,” he mused.

“Isn’t it?” you asked. “Calculating? From my general observations, some men offer to buy the woman a drink to make their interests known and then they may move on to asking if the woman would like to ‘get out of’ wherever it is that they are at the time.”

“Not for me it isn’t,” he answered. “Don’t get me wrong, I’ve offered to buy a woman a drink because I’m interested in her from a distance and would like the opportunity to know more, but beyond that I no more calculate making my sexual interests known than I do my interests in eating when I’m hungry or drinking when I’m thirsty. For me, it’s...more primal.

“A dance if you would. I respond to the woman’s body language and sometimes even her words if her approach is a bit more direct. A sexual encounter, and any preamble to such, is a constant give and take of energy and passion from beginning to end, not an orchestrated series of events.”

“Signals,” you mumbled, pivoting your legs to turn them closer to his.

Jackson’s eyes followed your movements as he licked his lips. “In a manner of speaking. Yes. Signals.”

“These signals...how can you be sure they’re from a standpoint of sexual attraction from the other person?” you asked as your gaze dropped to his lips, which promptly curled into a smirk.

“You can’t ever really know for sure. It almost always will come down to one person making the first move and the other person reciprocating,” he replied as he slowly rocked forward, his eyes shifting between your stare and your pout as if he were giving you a chance to stop him from coming any closer if you so wanted. Tentatively his hand came up and brushed a loose strand of hair away from the nape of your neck and you shivered beneath his touch. “Please tell me if this isn't okay,” he whispered, so close you could feel the heat of his breath on your lips.

You could feel the pulse point in your neck throbbing and what felt like fire where his fingers still lingered. A pressure in your chest made it difficult to breath and as his nose brushed against yours, a heavy flow of air passed through your parted lips. Closing your eyes, you tilted your chin towards him and his lips pressed against yours. You heard him inhale deeply through his nose, felt him move to sit closer as the hand on your neck flattened, gently keeping you in place.

It wasn’t your first kiss, but certainly the first in a very long time. Clearly Christopher Chapman hadn’t the slightest clue what kissing was actually meant to feel like, because your first kiss with him behind the swimming pool in the sixth grade seemed like a strange experiment gone wrong compared to the one you were experiencing now with Dr. Neill. His lips were soft, gentle yet firm and expertly coaxing yours to make the correct movements. He caught your bottom lip between his and lightly sucked, moving to give you the chance to do the same to him.

A moan vibrated against your pout as he tilted his head and licked over the seam of your lips. You instinctively opened your mouth and he responded by stroking your tongue with his own, seducing it into a sensual dance that sent more tingles to your core. Your inner muscles clenched and you could feel more of your essence dripping onto your panties as the hand not at your neck moved to your waist. It was then you realize that your hands remained in your lap atop your notepad.

Your body tensed as you tried to think of what you should be doing with your hands.

DAMN IT, CHRISTOPHER CHAPMAN!! YOU TAUGHT ME NOTHING!

Suddenly your lips felt cold and abandoned and you opened your eyes to find Dr. Neill looking at you with a concerned expression.

“Are you alright?” he asked, the hand on your neck beginning to retreat.

“Yes! I just--” You looked down and held your hands up. “What do I do with my…” You looked back into his eyes, all but certain that he would realize that very moment that his time would be better spent kissing a woman who’d been kissed more than once in her life and by someone better equipped than Christopher Chapman had been.

To your surprise, he smiled at you and carefully moved your notepad to the coffee table before he gently took your hands and pulled them around his neck.

“Start here,” he answered, cupping your face. “After that, just do whatever you feel.” He closed the space between you once more and began to kiss you again. His lips moved with slightly more insistence and he hummed against your pout as his body shifted even closer to yours until the outside of your thigh was pressed against his.

One of your hands slid over his shoulder and rested above his heart, surprised to feel it racing against your palm. Your other hand drifted up until your fingers were stroking his hair and he groaned his approval. Pulling away again, he carefully reached for your glasses.

“May I?” he asked in a breathy voice, forehead touching yours. You nodded and he pulled the frames off of your face, folding the legs in and setting them gently on the coffee table on top of your notepad. Cupping your face again, his thumbs stroked your flushed cheeks as he dropped another kiss on your lips. “You’re so beautiful,” he whispered.

The corners of your pout stretched until a smile rested on your face and he grinned back, kissing along your jaw. You shivered again, eyes closed as your head tilted to give him more access. With every peck on your skin, your center burned with desire and you sighed aloud.

“If I do something that makes you uncomfortable or you want to stop--”

You cut him off by catching his lips in another kiss, wrapping your arms around his frame and earning a moan from him and he too enveloped you in his arms. Your hands slid over every surface of his upper body that you could reach. First his chest, then his back both of which were still covered by his button down shirt, then moving to his hair and reveling in how soft the locks were. The areas closest to his neck were damp with sweat and his skin was just as hot if not hotter than your own.

“Is it hot in here?” you asked, whimpering when he dipped his head to kiss along the column of your throat.

“It’s us,” he whispered against your skin. He nibbled on your pulse point as one hand slipped fingers beneath your sweatshirt and you gasped. It was as though he was leaving trails of fire everywhere he touched you and you suddenly had an urge to feel his bare skin against yours. With clumsy hands, you loosened his tie and began to unbutton his shirt.

He must’ve approved because he moaned against your neck and began to suck on the spot he’d been nibling. The hand beneath your cardigan slid over your ribs, up the center of your back and across your stomach.

“Can I take this off?” he asked, tugging on the sweatshirt.

“Yes, please,” you answered in a shaky whisper. He pulled the top off of you and sighed as his eyes drank in your newly exposed skin while your hands finished undoing the buttons of his shirt. He allowed you to push the shirt and tie off his shoulders and watch as you ran your fingers over the thick hair that peppered his chest.

Smirking at you again, he went back to kissing your neck, making a path to your collarbone as he reached behind you and unclasped your bra with skilled fingers.

You sighed. “Dr. Neill--”

“--Jackson,” he purred as he pulled your bra off. “Call me, Jackson.”

He would’ve loved to have you call him, Dr. Neill while he tasted every last inch of you, but considering that it was, as far as he guessed, the first time you’d ever had such an encounter, he thought it best to save the kinks for another time.

You bit your bottom lip, hands threaded in his hair as he continued to leave wet kisses along your collarbone.

“Oh, Jackson,” you whimpered. He growled against your skin as his arms pulled you closer until your breasts were pressed against his chest. Leaning back, he pulled you on top of him, fingers slipping beneath the hem of your skirt to pull your leg over his hips until you were straddling him. “I’ve...never done this before,” you said, trembling in his arms as you settled in his lap, gasping as you felt him--long, hard and throbbing--against the soaking cotton of your panties.

“I thought as much,” he replied as his fingertips danced over your spine. “We don’t have to do anything if--”

“I want to learn,” you whispered, trying to press yourself harder against him. The throbbing of his shaft tickled your core, building an ache at the apex of your thighs. “I want to learn how to please you.”

He groaned under his breath as his hands grasped your hips and squeezed. He nodded, eyes drifting down to your breasts as he licked his lips at the sight of your nipples, stiff and inviting.

“Let me take care of you first,” he said, meeting your gaze again.

He wanted to show you how it could be just as good for you as it would be for him. He wanted the first taste of your forbidden fruit, to watch you squirm and writhe while he took your to the edge of insanity and let you linger in ecstasy until you wanted more.

“The more turned on you are, the more intuned with your own body you are, the easier it’ll be to pick up on what feels good for me,” he explained. “The key is not to think too much about it.”

You nodded your head, fighting an urge to rock your hips against him. You gasped when he gently moved until you were laying on your back with him still snugly placed between your legs. His hands slid over your thighs with a feather-light touch, pushing your skirt up around your waist. Kissing your lips again, he moaned against your mouth and peppered kisses down your neck.

Inside his jeans he was wet and throbbing, desperate to break free and be touched, but he ignored it for the time, focusing on arousing you and only you.

“Just pay attention to what feels good,” he whispered against your collarbone as he kissed his way down to your breasts, finally having a taste of your hard, perky nipples. Jackson groaned as his fingers teased the nipple that wasn’t in his mouth. “I can smell how turned on you are.”

For a moment, you wondered if he enjoyed the smell and bit your lip nervously as your back arched. You could feel the thick coat of fluids in the crotch of your panties and the burning grew in intensity as his hot mouth devoured your nipples one at a time. Despite the fact that your clothes were mostly off, save for your skirt and panties, a light layer of perspiration covered your skin. His wet kisses continued on, forming a fiery path over your ribs, down your stomach and your muscles tensed with nerves as he inched closer to your center. More dripped from your opening and the closer his mouth got to your most intimate place, the more intense the tingles became, almost beckoning him there.

“Jesus, you smell so fucking good,” he purred.

You had never heard him cuss before and while in any other circumstances you may have found it crude, it only seemed to arouse you more. Your knees instinctively spread further apart and your hips rocked forward on their own accord. Cold air hit your core as Jackson pulled your panties aside and groaned at the view. You lifted your head to look down at him, watching his eyes devour you and you blushed.

The sight of your wet, pink center was enough to send his senses into overdrive. Your scent was sweet and thick, urging him closer until he gently touched his lips to your vulva, leaving a tender, wet kiss as his eyes shifted to watch as you arched your back.

You moaned deeply and a fresh shiver settled in your nipples, hardening them further while further down the heat of his mouth sent more tingles to where it stimulated you.

Jackson’s cock throbbed desperately in his jeans as he kissed and licked you. Your pussy was so sweet, so soft and wet and hot that he could’ve come in pants right then and there if not for the promise of you returning the favor after he was done. To his surprise, both your hands reached to clutch at his hair and he moaned against you, pulling back and using his fingers to spread your inner lips. At the sight of your hymen, he groaned again and stretched his tongue to lick along the thin layer of skin before making his way back up.

He sucked your clit into his mouth as one finger came to rest beneath his chin, grazing the tip against your entrance and smirking against you as moans and whimpers tumbled from your lips. He decided not to penetrate you and moved to wrap his arms around your thighs, keeping your hips still as he sucked harder, building the orgasm that he could sense was near.

“Oh God, Jackson! That feels--so--good--oh my g--”

The only coherent thing that escaped your lips were moans that grew in volume as the burning in your center became stronger. Your hips struggled to buck against his face as your chest heaved and your body felt numb when suddenly it felt as though your core was exploding. Your legs trembled on either side of his head and your hands gripped his hair, keeping him close as you gasped and stopped breathing for several seconds. When your breaths returned it was with a loud, guttural moan that you never realized you were capable of and you trembled as you rode the wave of pleasure Jackson had sent you on.

His tongue and lips gradually slowed as Jackson moaned against your pussy, savoring your flavor for just a little longer before kissing his way back up your body, leaving a wet, sticky trail all the way to your lips, where he paused and smiled down at you.

“Do you want a taste?” he asked in a whisper. “Your pussy is so sweet.”

His words made you blush and the sight of his glistening mouth and chin sent another tingle down your form. Nodding your head, you closed your eyes when he pressed his lips against yours and licked into your mouth.

“Did you like that?” he asked against your cheek as he nuzzled your skin with his broad nose.

“Yes,” you whispered, still trying to catch your breath.

“You sounded so sexy when you came,” he purred against your mouth, kissing you again. “I think I could eat you all day.”

You blushed again, biting down on your bottom lip when you felt his erection pressed against your thigh. “I’d like to take care of you now...will you show me?”

He smiled and nodded his head, looking at you through hooded eyes and moving to stand in front of the couch. His hands went to unbuckle his belt as you sat up and moved ched to the edge of the cushion. Tilting your head up, you looked at him and the expression on your face sent another rush of blood to his shaft. His erection was almost painful and as he unbuttoned his jeans, your hands laid over his.

“May I?”

He moaned, nodding his head and watching intently as you freed him from the confining denim. “Careful,” he whispered as you pulled them down, his cock swinging up to slap against his belly. Your eyes widened, hands pausing and he took the moment to push his jeans down the rest of the way, kicking them off along with his boxer briefs.

“It’s big,” you mumbled in awe as your fingers gently grazed over the underside. He moaned, biting down on his lip to keep himself from pushing himself into your mouth. “So soft but...hard all at once.” Your eyes followed his length, noting how the top was shiny with a gathering of wetness. “And wet?”

“Yes...when a man gets aroused, he gets wet, too,” he replied.

For a moment longer, he let you explore and examine his manhood and wondered what was going through your mind at that moment. Experimentally your hand wrapped around him and squeezed gently and he swore he saw stars dance in front of him as he cock throbbed again.

“Did that hurt?” you asked, looking up at him.

“N-no, it felt really good. You can use a firm grip, it won’t break, I promise.”

Your hand tightened the slightest bit, bringing it down so that you could look at the head more closely and noticing the tiny opening at the top where all the clear liquid that covered the top of his shaft was coming from. Curiously, you rocked forward and lightly licked at the hole.

“Oh fuck yeah,” he moaned, head falling back.

“It tastes…” He looked back down at you, hoping the extra pineapples in his diet paid off. He didn’t want you to be turned off by anything but least of all the taste of him. “Sweet...a little bitter. Slightly tangy, like a grapefruit.”

You looked up at him and he groaned at the sight of your plump lips so close to the head of his cock. “Every man tastes different, just like every woman has a different taste.”

“Do I stroke it like this?” you asked, apparently eager to move on from taste as your hand moved back and forth in a quickened pace.

“No, no! Not that fast at first!” he exclaimed, large hand wrapping around your wrist.

“I’m so sorry--”

“--It’s okay--”

“--I’ve seen...pornography where--”

“--Really, it’s fine. It’s a common misconception,” he said. “You start slowly, like this…” He moved his hand over yours and guided your movements over his shaft. “That feels good like that. Now do you see underneath? My testicles?” He hated using the words testicles in that moment, but for some reason thought the word balls may have offended you.

“The balls,” you said, nodding. He let out a chuckle, pursing his lips shut to stop it from continuing.

“Is that not the correct--”

“--Yes, it is...I just didn’t think you’d...nevermind--”

“--I’m not entirely naive about the male form, you know,” you said, smiling up at him.

“I didn’t think you were,” he replied, stroking your cheek with one finger. “Use your other hand to massage them. Gently, they’re sensitive.”

“Okay,” you whispered, doing as he said and looking up at him to be sure you were doing it right. “Like this?”

“Yes, just like that,” he replied between panted breaths. “That feels so good, keep going…”

You could see more fluid oozing from his tip, dripping onto your knees and you moaned softly, looking up at his face to find his eyes closed and his lips slightly parted.

“Oh my God, that’s right. That’s so good,” he groaned. His eyes opened wide when he felt the heat of your tongue on the tip of his cock and he dropped his gaze to see you licking up his precum. “Oh f-fuck, that’s amazing!”

He thought about what it might feel like to slide down your throat and groaned as his head fell back again.

“Do you wanna try putting it in your mouth?” he asked hopefully.

You bit your bottom lip and answered by wrapping your lips around his crown, feeling a swell of your ego as he cried out, clearly enjoying what you were doing. His fingers slid through your hair at the top of your braid.

“Sucksuck!” he urged, eyes screwed shut as he tried to keep himself from coming so that he could feel this good for as long as he possibly could. “Fuck! Yes! Y/N, just like that, suck my cock! Oh fuck, yes!”

His words spurred you on and made you feel like a sex goddess. It was intoxicating to make him feel as good as he had been making you feel and you moaned around him, earning another sound of pleasure.

“Can you take more in your mouth?” he asked, looking down at you as you met his gaze, lips still wrapped around his head. “Oh fuck, you look so sexy right now,” he groaned.

You smiled, letting him pop free from your mouth. “I can take more,” you said.

“Don’t worry if you gag, it’s natural--”

“--Oh, I don’t have a gag reflex. I never have,” you replied, shaking your head.

A cloud of lust emerged in his eyes as he groaned and carefully rocked his hips so that his cock brushed against your lips. “Take a little at a time...and be sure to breathe before you take more in,” he purred, hand in your hair guiding you forward.

You opened your mouth and resumed your suction, pulling more of his shaft towards the back of your throat.

“Up and down,” he whispered, again using his grip to guide you. “Like that. That’s my girl.”

Your nipples hardened as a tickle danced over your center and you moaned as he reached the back of your throat.

“Ohhh f-fuck, that’s it. Good girl...of yeah, that’s so fucking good,” he groaned as you moved your head up and down his shaft like he’d shown you. “Faster,” he whispered.

The wet sounds made your clit tingle and the hand you were using to massage his balls moved more insistently while still taking care not to be too rough. You moaned when he began thrusting into your mouth, his breaths coming heavier and closer together.

“Your throat feels so good,” he moaned as he moved your head faster over his cock. “Oh fuck, I’m gonna come so hard...do you want me to come in your mouth?”

You looked up at him and nodded as best you could with him still pushing himself in and out of your mouth.

“If you don’t wanna swallow, just push against me, okay?” Again you nodded, mouth still preoccupied.

His grunts became more frequent, hand moving you faster still over him and you felt his shaft expand and twitch as a warm splash landed on the back of your throat. Instinctively, you swallowed and moved your head on your own to catch more of his essence on your tongue. You moaned at the taste, sucking his organ to get as much as possible as you continued to swallow everything he gave you. His grip on your hair loosened as you kept sucking.

“Suck a little softer and slower...that’s right...oh fuck, Y/N, your mouth is fucking amazing,” he whimpered. His legs shook as you swallowed the last of him down and you looked up to see his face was flushed and look of satisfaction settled over him. “Gradually slow down,” he whispered. “That’s it...just like that. Okay now slowly pull up and let me out.”

You gently let him pop free of your lips and watched as his cock slowly softened, twitching in aftershocks every so often.

Taking a deep breath, he bent to kiss you deeply, moaning as he tasted himself in your mouth and gently pushing you to lie back on the couch. He laid beside you as his hand ghosted over your form.

“Fuck, that was amazing,” he said as he peppered kisses over your face. “Are you alright?”

You nodded as your arm wrapped around him and you rested your head against his chest, sighing contently. “Yes.”

You felt so safe with his arm draped over your side, holding you close to him while his other hand held yours at the center of his chest.

“How do you feel?” he asked, turning to kiss your forehead.

You paused to consider your answer, finally settling with, “Delightfully enlightened.”

He chuckled against your skin, looking down at you as the arm around your frame moved to trail his fingertips along the lumbers of your spine. “There’s so much more I could show you...if you’d let me.”

You met his eyes, cheek still resting comfortably against his pec, and smiled up at him. “I would love that.”

92 notes · View notes