#i dated a british guy in college lolololol

[guiltiestlove]

thinking about pre-incarceration 20 year old inexperienced!Simon getting rode into oblivion by his first girlfriend <3

He’d be smug and bratty at first to hide how nervous he is, just to get progressively more and more needy and submissive, all the while trying to cover his face with his hands, hiding how red his face has gotten <3

(🥩 anon, hope u have a good day ✌️)

The heating in your college dorms goes out—good thing you’re staying over with your boyfriend Simon Blackquill so he can help you stay warm.

Simon Blackquill x fem!reader, ~2600 words

N/SFW, mdni!!

cws/tags: smut of course, reader with vagina + breasts, fingering, protected sex, loss of virginity, handjob

notes: didnt know this prompt was gonna speak to me so much since i dont normally like to write younger simon—i ended up drawing on a lot of personal experience and it was fun LOL; hope it fits the prompt enough :’)

You’d taken a handful of psychology courses by this point for your degree, so you were used to participating in research studies for credit. That was no big deal. But what you weren’t used to was a really hot student tech administering the tests on you. And you doubly weren’t prepared for his sexy accent.

And while he seemed a bit taken aback when you gave him your number, surely this happened to him all the time, right? The blushing and babbling were probably a result of you coming on too strong in a professional setting. Of course, that’s all it was.

But to your surprise, two months and many dates later, you come to find that Simon Blackquill is nothing like you expected. Not only is he rather reserved and nerdy, apparently you were the first person to ever give him their number like that. And not just that, but he’s never put himself on the dating scene—a total shock to you as you couldn’t find him more endearing.

And watching him figure out how to be your partner was delightful. He never knew how to balance his pride and overflowing embarrassment. You assured him it was fine that he was inexperienced, and you’d always take it at his speed.

And in fact he did take things at quite a slow and steady pace…at first, that is. But the night you stayed over and the heating was out, it was all over for him.

——

“Do you think it’s torture that the university has us in dorms at this temperature?” you practically chattered, sitting criss-crossed at the end of your boyfriend’s bed, notebook in hand.

At his desk, Simon smiled, putting his book down. “Hah, surely you can handle a little chill, can’t you?”

You feigned indignation, “A little chill! I can’t believe you’d let your girlfriend freeze to DEATH and call it a little chill! And you call yourself a gentleman.”

He stood from the creaky wooden chair, stretching his arms over his head. “Hmph. Well, darling.” He approached where you were sitting and leaned over you. “Do you have something in mind? A way to keep warm?”

“God, yes.” You pulled him by the collar til your lips met, a romantic slow kiss at first. Even though you’d only been dating him for a short period of time, the way he made you feel was unbelievable. You constantly told him how gorgeous he was, but the man always brushed it off. But fuck, he just did something to you. Seemingly aloof, Simon could be such a sweetheart and you loved to bring that out of him.

You began to stand up as you pulled him down and gently laid him onto the bed. Facing him, you planted a knee on either side of his hips, and you stopped moving once your whole body hovered over him. You smiled and ran a hand down his chest as you studied his face. A slight smirk, growing blush, and focused eyes. You were enjoying the view, just feeling his chest rise and fall as his large hands grabbed your ass and planted you on his crotch.

Not realizing you had been holding your breath, you let out a gasp at the sudden touch. While the two of you had fooled around a bit, you hadn’t done much more than make out. Each time you had been interrupted or the moment didn’t feel quite right. But this time. This time Simon was staring at you biting his lip, clearly wanting to ask you something. And his hard cock was so tantalizingly pressed against you.

“Simon…” You hadn’t anticipated sounding that needy. “…we don’t have to do anything you don’t want to, okay?” He grabbed your hand tightly. “Please, no, I need you to know… Er, rather… tell me what you want… I-I don’t know how to say…”

Your brow furrowed as you tried to figure out what he meant, and he continued. “…Fuck, you have to understand, since I haven’t done this before, I—.” Your poor boyfriend was practically beet red, you just wanted to comfort him, ease his worries.

“Hey, honey…” You took his face and kissed his lips gently, feeling his muscles relax ever so slightly. “…If you want to know what I want… It’s you. Whatever you’ll give me.” And his mouth was back on yours before you had a moment to realize what that meant—how that meant he wanted you like this too.

And as the realization settled in, your kisses became greedier, tongue searching his mouth just to feel more of him. “Fuck, Simon,” you muttered under your breath as you tried to get as much friction as you could from grinding against his lap. A whine in a pitch you hadn’t heard from him before escaped his lips.

“You sound so pretty for me already...” you murmured, unsure if he could even hear. And then you felt him, hands trembling, reach for your shirt to take it off. He looked to you as if to ask if it was okay, but the nod you gave was beyond enthusiastic. In fact your lip was nearly bleeding you were biting it so hard in anticipation.

You let him carefully take your top off, then unbutton your jeans. “You’re gonna have to keep me warm, okay?” you teased, but he just absentmindedly nodded, utterly overwhelmed by your body.

Reaching out to you he finally formed a thought, “You look like a goddess…” From anyone else you wouldn’t have believed in its sincerity, a ridiculous pick-up line at best. But from Simon? It felt like a classical painter appreciating his muse.

“You’re one to talk,” you replied, eyes flicking up to meet an even more embarrassed Simon. And you reached for his shirt buttons, as desperate to touch him as he was you.

Revealing more of his skin you felt hungrier and hungrier, picking up the pace. “Can I take off your pants?” You looked at the man with such desperation, and Simon felt totally unprepared for someone this beautiful to be asking him this question. But he for damn sure wasn’t missing his opportunity, and ripped his pants and underwear off as fast as he could.

“Fuck,” you whispered when you saw Simon like this completely nude. He was propped up on his elbows, staring at you for some sort of sign of approval, and you were just sitting there in a trance. “I-Is everything alright..?” he meekly interjected, slight goosebumps from the cold.

“Holy shit, Simon.” You began crawling on top of him, as slowly as you could, taking his cock into one hand. “How is every inch of you…” He whined as you took hold of him. “… so fucking perfect.” You stroked him gently as you placed soft kisses across his face and neck. Suddenly heat was radiating off his entire form, his breath shaky and unsure.

“F-Feels so good…” his head rolled against the pillow. Already he was becoming overwhelmed with pleasure, and you knew you had to back off slightly or your excited boy wouldn’t last.

As you removed your hand from Simon’s throbbing dick, you went to take off your final piece of clothing. Watching your lace panties hit the floor, Simon gulped nervously. He had barely moved from where you had placed him on the bed—he had been wholly determined to follow your lead.

“Babe… please…touch me,” you cooed as you straddled him again and grabbed his hand and guided it to your folds. Biting his lip and turning bright red, your boyfriend was practically whimpering.

You took his hand letting it gather all your sticky arousal, and you noticed your boyfriend’s breaths become more ragged. With your other hand you spread yourself open, and little by little you showed him how to tease your clit. Words mindlessly fell out of Simon’s mouth as he blissfully stroked your clit and listened to your high pitched whines, “So wet… you’re so wet…”

You could have let him touch you like this for hours, but you grew impossibly impatient by the second, needing his warmth in more ways than one. “Simon…need more…,” you breathed as you moved closer to his face—you wanted to soak in every expression, every feeling he was offering you. And you helped guide his thick fingers inside you.

The moan you let out was truly filthy, but his fingers just felt so good inside you. And though Simon was also turned on, he was so concentrated on making you feel pleasured as well—he looked like his brain had to have been at full capacity.

Composing yourself, you started kissing him again and guided him as he fingered you. Showing him proper technique was the last thing on your mind right now, because god, Simon’s fingers were inside you, and it was even better than you imagined. He slid in and out, curling to reach deep inside you, and once he found this rhythm you placed his thumb on your clit.

After a bit you squeaked out, “Another finger Simon.. please,” and you watched his eyes widen. “O-okay,” and he slid in another finger stretching you out, and frankly, you were worried he might come from just this alone.

Breath becoming labored, you couldn’t take anymore yourself. “This feels so good baby…” As you spoke, he looked at you like you were the only person on the planet, in the solar system. “…I want more…Fuck, Simon I need you.” You looked down to his cock and stroked it just once as his eyes fluttered, and he bucked into your hand.

Catching his breath he quickly breathed out a “Dear god, yes,” and he watched as you licked your lips and positioned your hips closer to his. Thankfully he had been hoping for this, and he reached over to his bedside table and pulled out a condom.

“You’re always so prepared for everything aren’t you Simon,” you giggled as you traced shapes on his hips and he shakily rolled the condom on. “And thank heavens I am,” he replied blushing, unable to look you in the eyes.

Bending over, you kissed him slowly, passionately. Fingers running through his hair, you spoke softly, “We can stop at any time yo—“ He quickly interrupted, “NO, no, it’s not that, I-I’m just nervous…” he was grabbing at your hand. He looked to see your face, incredibly soft and kind, a smile that felt.. reassuring. He relaxed with a sigh and returned the smile.

“Let me take the lead baby,” and you once again kissed him, this time quickly making way down his neck… soft pecks turning into nibbles that turned into sucking bites. And as you pulled away, he chased after your mouth until he realized you were about to position yourself onto his cock, and he sucked in a breath. And furiously nodded, biting his lip.

His tip reached between your folds, and you already were moaning. Simon had grasped the bedsheets in two fistfulls with his eyes screwed shut. Little by little you sank down, telling him just how good he felt, how he fit inside you so perfectly. He was sweating and speechless and already looked like he was in ecstasy as you tried to get his attention, “Simon how does it feel, is it okay?”

“Hhhhnngg, holy fucking shit.”

You giggled. He looked so beautiful right now underneath you, putty in your hands. It was difficult to keep your composure when he felt so good and looked like an angel. You leaned down and pressed your body against his. “D-does it feel good f-for you?” he could barely get out the words—he was definitely struggling.

You couldn’t help but chuckle as you lazily met his mouth with yours. “Baby, I could spend a whole lifetime here.” And you slowly started grinding your hips against his, granting a little friction between the two of you.

By now he had seemingly lost the bashfulness, as his mouth was agape and his eyes rolled back in his head. You planted kisses across his whole face as you began rolling your hips at a quicker pace. Simon’s hair stuck to his forehead as the sweat rose to his skin, and you carefully moved it out of his eyes.

The rhythmic grinding, though incredible, wasn’t enough. And you shifted, sitting at an angle to properly ride your boyfriend. A low moan was all that Simon could utter. His pupils were blown out, and he looked like he was on the absolute edge. “Can I go faster, baby?” you huffed, and he enthusiastically nodded, unable to speak at all now.

You grabbed both of his hands and interlaced them with your own and pulled off his cock almost completely, eliciting a delicious whine from Simon, and then slammed back into him at full speed. In this position you could perfectly hit the most satisfying spot inside your core.

And so you rammed your hips into his. Again. And again. Harder and harder. His knuckles were white with their grasp on yours, and you were certain you had never heard a man make prettier sounds than this. Fire ignited your veins as you felt yourself clench around him, the squelching noises and moaning mixing in the air.

It wasn’t long before your rhythm became more erratic, your lust fueled by the nearly fucked-out man beneath you. Simon was barely clinging on, he was trying so hard not to come even though it’s all his body wanted and all his mind could think.

Tugging away one of your hands, you hastily spit into it and worked your clit, desperate to reach your climax faster.

Upon seeing you touch yourself like this, Simon couldn’t hold back anymore. No words left his lips, it was a sudden violent orgasm that wracked his whole body with shivers, and you arched your back too when you felt his cock twitching inside your walls.

“Just a little more…so close…” you whispered as you used your whole hand to furiously get off, and when you opened your eyes you saw Simon groaning, holding onto your hips with fingers pressed deep into your flesh and tears in his eyes.

You instinctively grinded down onto his spent cock and he jolted as you moaned, “Is this.. okay? Just … a little more?” He squirmed, completely and totally overstimulated, but nothing could have stopped him from enjoying this moment. The pain and the pleasure mixed as he shakily took one hand and grabbed your breast with force, tweaking your nipple. “‘s ‘kay,” was all he could mumble in reply, and it was barely more than a breath.

Grinding down on him again as he played with your nipple, you found the heat within you rising and rising. “Fuck, Simon, gonna—“ and your breath was taken away by waves of pleasure emanating deep from within you. As you whined and trembled, Simon still held you down, wanting to feel as much of you as possible like this. The ecstasy rolled throughout you as you cried your lover's name, eventually becoming just a hushed whisper.

As you felt the calm washing over you, your body collapsed onto Simon, and he carefully wrapped his arms around you. The room was once again silent except for two pairs of shallow breaths, and you felt your heartbeat begin to match the tempo of his.

“Simon…” you finally broke the silence with a raspy whisper as your breathing calmed. “Mmhm,” he sleepily answered, nuzzling his face deeper into the crook of your neck. “I don’t feel so cold now.” You felt him chuckle against you and pull you in tighter as he finally spoke, “Perhaps the heating should malfunction more often, hmm?”

And as you lifted your head up to kiss his cheek and sweep the hair out of his eyes, you smiled, knowing there would be many more nights like this to come.