[normal flag id: a rectangular flag with 7 horizontal stripes. the second, third, fifth, and sixth stripes are scalloped facing outwards. from top to bottom, the first 3 stripes are a gradient from cold blue to light sky blue, the middle stripe is yellowish-white, and the last 3 stripes are a gradient from light olive green to dark green. the entire flag is surrounded by a dull dark brown border. there is a symbol of a light cold blue heart in the middle of the flag, outlined twice: first thinly in olive green, then thickly in yellowish-white. end id.]
[simplified flag id: a rectangular flag with 7 horizontal stripes. the second, third, fifth, and sixth stripes are scalloped facing outwards. from top to bottom, the first 3 stripes are a gradient from cold blue to light sky blue, the middle stripe is yellowish-white, and the last 3 stripes are a gradient from light olive green to dark green. the entire flag is surrounded by a dull dark brown border. end id.]
I don't know if you have done this before. Can you do a NSFW Scenario with Jack and a virgin female? like he finds out that she is a virgin and is really soft with her?
Popping Cherrys | Jack the Ripper x Reader | NSFW
No, I'm honestly surprised, but I think I haven't written about Jack popping someone's Cherry. Sigh, disappointed with myself. Good that you mentioned it, sweet anon!
Warnings: Smut under the cut, cherry popping, p in v, fluffy Jack, a bit awkward starter reader
Having Jack as your boyfriend was... Interesting. He was a touchy person, not all too aware of the concept of "personal space". Or he just really liked to invade these spaces. Maybe both.
His behavior made it obvious you couldn't keep your innocence a secret for too long. When Jack found out, he was a little surprised. Not that he thought it was bad, quite the opposite.
You felt a little odd, knowing Jack had experience. It wasn't like he ever was shy or embarrassed of his history. Even less with you and when you asked questions. If anything, he reveled in the way your cheeks heated up and you got embarrassed all of a sudden.
Thinking back on it, he probably should've made the connection of you being a virgin sooner, given your reactions to certain topics and moments. He just figured such a pretty lady would've had enough chances before him. And you probably had, he was just shocked that he was the one you'd take.
Taking the step to start having sex was something you had to initiate. Jack tried his best to be patient, settling for hugs, or an arm around you whenever he could. The tall captain did not want to put any pressure on you, if you wanted to eventually have sex with him that was fine. Having your heart was already way more than he had thought possible for himself.
Your first time happened after a night out with Jack. The mood was good and light and you already often slept together, or more like slept in the same bed together. As you settled down happy giggles and jokes were shared, playful kisses teasing upon the other's lips.
A little making out, a bit bolder than usual but nothing too new. Jack was laying down on his back, having you above him. His one hand on the small of your bag while the other was playing with your hair. His boner was poking against your ass, although this time didn't make you nervous. It happened a lot before too, Jack would always laugh and tell you to ignore it.
It wasn't like he could control him but one boner wouldn't kill him. Especially if he got more kisses.
Just today, the heat between your legs was making you bold. Not only thinking but actually acting on it. You slowly started to rock your hips back and forth on his, enjoying the hard outline of his cock and how it made you feel when it rubbed against that special spot between your legs.
Jack let out a startled groan, eyes opened wide in suprise as he stared up at you. A shy smile creeping on your lips in response.
"Is this okay?", you whispered. Jack felt his throat tighten, his mouth running dry as he started nodding softly, without even thinking about it.
"More than okay, keke.", he responded after a moment.
His hands slowly settled on your hips, slight pressure on his fingertips digging into the supple flesh as he supported your movements. Your breath shuddered, your lips meeting his eager ones again.
There was something nice about this, about feeling the heat and sensation of just dryly humping on your boyfriends twitching but still clothed cock. The way your lips pressed against one anothers, the shaky breaths between.
When you pulled back, Jack opened his eyes again. The golden hue almost completely hidden behind the black of his dialated pupils. Jack started up at you like you've put up the stars and the moon in the nightsky. Like you were a goddess that simply allowed him to gaze at her beauty, barely sure if he was allowed to actually grasp you, feel you.
A light chuckle escaped you.
"Are you okay?", you asked softly, biting your lip. Something about how his breathing had changed, how his chest moved up and down more rapidly while his eyes started at you with a few strands of messy hair covering parts of them.
"Not gonna lie, I'm so fuckin' horny right now.", he whispered before laughing. "What kind of spell did you put me under?"
"Love, perhaps?"
"... You're cheesy, keke."
Both of you shared a little laugh at that. You tilted your head, pursing your lip and trying to grasp the tension from before.
"So... Would you like to?..."
"To...?", Jack questioned.
"... Do... something... about our lust?"
Jack stared blankly at you for a long while.
"... That has to be the weirdest way of asking someone to pop your cherry I've yet heard of.", he muttered before chuckling. "Yes. I'd like to, if you're sure.", he added quickly before the weirdness of the moment could force you to back out.
"I...-", you started, "I think... I thought about it for a while. Just... be careful, yeah? I'm not too sure how... to... well, what to do with myself." Jack nodded at your admission, thumb gently massaging the spot where his fingertips firmly grasped your skin earlier.
"Come here...", he whispered before pulling you down by the neck. His grasp was firm but not forceful. He tilted his head a little sideways before kissing you again, this time the kiss had more urgency and purpose. Although still a bit nervous, you couldn't help but like how delicate his one hand was running up your hip and to your back, and sooner than later you were melting into his kisses again.
As you shared more and more kisses, you felt Jack's hands slowly adventure to your sides again before going up to grasp one of your breasts. He stroked and massaged through the fabric of your clothes, ensuring you'd be fine and comfortable with the action. Then he slowly and almost teasingly pulled down the cutout of your top, his fingers grazing while your nude flesh was revealed to him.
The biggest grin spread on his lips as the soft sounds of your pleasure reached his ears when he gently pinched and teased your nipple. He made sure to play gently with it, pulling at your clothes so both of your breasts would get the same amount of love from him. Picking favorites would be rude, after all.
"Does that feel good, lovebug?", he asked in a quiet whisper, his lips grazed your neck and you could feel his breath against your shivering skin.
"Yeah...", you nodded.
"Good", he cooed, "tell me if I do something that doesn't feel good."
The tall man kissed down your neck, over your collarbone down to where his lips would join his teasing fingers. His long tongue pressed flat against your nipple before wrapping his lips around and gently sucking. Your fingers wrapped in his hair, grip tightening and pulling at his hair causing him to groan against your perky bud.
After a few more moments, he pulled away, grabbing your top and lifting it a little to gesture that he wanted to take it off.
"Can I?", he asked. You only nodded, nervous excitement bubbling in your stomach. Not a second after your given consent the clothing was pulled off and thrown onto the ground next to the bed.
Drinking in the sight of your bare chest, his eyes practically sparkled. Adoration and lust in his gaze swirling like waves in a honeyed ocean.
"You're perfect", his raspy voice breathed out.
"Simply...", he started, licking his lips as his mind searched for a word fitting enough to describe you, "... divine." Your breath hitched when the word finally got uttered by him. It wasn't exactly unlike Jack to praise you, show his affection verbally too but it was unusual for him to use these kinds of words. Fancy words, as he'd put it.
But in this moment, he didn't care, didn't care that the words he spoke were unfitting for him because they were the only ones worthy to be used when putting you into perspective. What you were to him, how you made him feel.
The shy smile grazing your lips made Jack grin in delight too. He was leaning more forward, more and more until you fell back on the bed with him above you, your positions flipped. A moment later your lover had lost his shirt too, coming down to kiss you. His torso pressed on yours, feeling your hot skin against his.
The urgency shared betwen your lips was mutual. It wasn't simply lust anymore, it was need, need to be closer, closer than ever before. To be one.
Your hands explored Jack, going through his hair in a familiar motion before creeping down and over his back, nails digging little red stripes over his pale skin. Feeling the muscles flex and ripple with each of his movements.
At this point it became like a dance, like a trance. You stepped through the motions, discarding of your pants and his. Your head felt dizzy, fuzzy and you weren't even sure how it got to the point when both of you were fully naked on the bed with him laying between your legs.
Although you were very aware of it, and how it felt different from the clothed dry humping from before. The way his tip would graze your clit, pulling out loud moans. Installing a feeling deep within your loins, like something was missing. Your walls clamping around nothing in desperation. Suddenly, everything was on fire, all hot and you felt like Jack above you was a burning fire saving you from a cold snowstorm.
You moaned out for the man above you subconsciously. His name spilling from your lips and seeping into his mind. Jack would never forget, how his name sounded from your lips in that moment, echoing from the walls and burning into the deepest pits of his brain.
Although something deep within him screamed at him to push inside, feel your walls cling to him as he'd pound you into the mattress, he restrained. His lips sloppily kissed yours, rubbing his twitching cock through your velvety folds, enjoying the sensation for just a moment longer. Your mewls and moans like chants for him to keep going.
He pulled his hips back slowly, groaning at the lost sensation before chuckling at your big doe eyes staring at him. Wondering if you did something wrong, but mostly just confusion sparkling in your eyes as to why he had stopped. Why he had robbed you of this sensation that had just made you crave more.
Although cute, your expression didn't last very long. The confusion shifted when his long fingers took the place where his cock had previously been rubbing against you. Running between your labia and toying with your clit, making sure his fingers were plenty wet before slowly easing one finger in, then a second one.
His lips latched onto your neck, soft kisses placed and praise whispered against your skin. His fingers moved slowly, rhythmically. Working your hole open, preparing for the stretch.
"Good girl," he whispered, "Does it feel good?" Jack had his ears sharpened, looking out for each sound. Each gasp, moan, or mewl registered in his mind. Only picking up the pace of his fingers when he felt you relax enough, curling his fingers upwards.
His cock ached, oozing precum onto the bed as he learned what made you squirm. The tall mans lips sucked marks into your neck, moaning against the red and purple spots in lust whenever your hips bucked into his touch so eagerly.
Patience wasn't Jack's fortune but he'd finger you until his cock would wilt off if it meant he'd get to hear your pleasure like this forever. With each moan, each whine your lover got more and more eager to please. Pleasuring you to the edge, his tongue licking a long stripe from the marks up to your ear. A husky moan escaping him as he felt how your walls clenched around his fingers.
"Like this?", he whispered, tone of voice so cocky normally it'd make your eyes roll in annoyance although it was anything but annoyance that made your eyes roll back right now.
"Just like that," you whined out, pleasure too great to be embarrassed by the tone of your voice. Jack nodded, kissing the side of your face softly, peppering kisses while his fingers were working.
The pace of his fingers unchanging as your walls clenched and tightened around him like they had a mind of their own. His fingers only slowed when your release hit, working you through it but careful not to overstimulate and hurt you. Slowly, he pulled them back out, smiling happily at the cute gasp coming from you.
"Good?", he asked, eyes twinkling in delight as you nodded, still a bit dazed. He let you catch your breath, realizing the situation and getting your mind out of the gutter a bit. When you looked back up at him, he couldn't help himself but laugh from your face.
Jack was licking off your release from his fingers, tongue eagerly tasting and the tall man couldn't help but chuckle when you looked at him in shock.
"What? It's good." The unbothered tone in his voice made you chuckle too. Eyeing the tall man you called your lover up, it was clear he was content, the tip of his cock leaking onto the bedsheets but he looked just as satisfied. His eyes followed your gaze before looking back at your flustered face. He raised an eyebrow, wondering what was going on in your mind.
"Do you... want to... go further?" Now, this question surprised Jack.
"Do you?", he asked, staring at your face. While yes, the tall man would die to sleep with you right now, he didn't want you to think you "owed" it to him. If he had to, he'd wait a thousand years for you. Well, maybe not a thousand, patience really wasn't his thing, but maybe a hundred. Or longer than right now.
However, that didn't matter as your head nodded yes, that you wanted to go further. Wanted him, in all ways, not wanting to wait any longer.
Jack quickly positioned himself above you again, kissing you softly. The pace was slower now, less urgent but more intimate. His body rubbing against yours, working you up slowly. He made sure his cock was wet with your slick.
Slowly, he pushed inside, feeling your arms around him clinging to him. Jack leaned his forehead against yours, making sure to watch your reaction and pause whenever it got too much for you. Gently he kissed your cheeks, your lips and the tip of your nose, soft praises uttered from his lips to soothe you.
He waited a few moments after sliding the last inches in, letting you get settled with the stretch of it. Only when you nodded to assure him, he started moving slowly. Easing himself out before pushing back in. Slowly, working it up, pulling out a bit further each time.
Soon enough both of you were moaning, lips smashed against each other and Jack had to clutch the bedsheets beside you to remind himself to keep it gentle, keep it slow, and give it to you like you deserve. The rhythm now was steady, gently rocking the bed a little back and forth. One hand beside you on the bed while the other toyed with your clit to ease you further into the new sensation.
A sly smile was on his lips, the tall man was reveling in the way of how the sounds coming from your mouth were more and more motivated with pleasure. Your lover bit his lip, doing a bit of algebra in his mind to postpone his orgasm, not wanting to bust too soon after you started properly enjoying the act of making love with him.
Only when your toes curled and he felt the familiar flutter of your walls around him, did he let his shoulders relax. Jack rocked his hips more sloppily into yours, trying not to be erratic as he worked you both over the edge. A moment after your release he pulled out, a few jerks of his hand before white streaks of arousal were painted on your stomach.
For a moment, there was only the sound of your heavy breathing through the silence. Your eyes stared at the sticky release on your stomach before looking up at Jack. Jack looked a bit sheepish.
"I wasn't sure if you wanted me inside...", he admitted before chuckling. "I'm gonna get you a cloth."
Your lover pressed a kiss to your forehead before standing up and leaving through the door to his bathroom. Only a moment later he came back with a wet wash cloth. He gently wiped you down, peppering more kisses to your face.
"How was it?", he asked.
"Hurt a little...", you admitted
"I'm sorry, lovebug."
"No... It felt really good after... Just, the first few moments..."
Jack chuckled, nodding.
"I can imagine." His voice was soft as he pressed another soft kiss to your lips.
"How was it for you?", you asked quietly. Jack looked a bit suprised before laughing.
"Do you want me to be honest, snugglebug?" Although this sentence set a bit of anxiety in your tummy, you nodded.
"If I ever say something that is less than 'perfect', I want you to kill me. Because somebody has stolen my identity."
The sentence made you feel warm and fuzzy. You wrapped your arms around your lover when he laid back down next to you.
"You're stupid", you giggled.
"And you're cute", the tall man replied amused.
