IMAGINE: Having your first time with Jack (Agent Whiskey x reader)

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Warnings: smut

Jack had always stopped when things got too intimate. He knew you were a virgin and your confession seemed to have pushed him into a direction he didn't like at all.

You were laying on your sofa once again, making out, and you already had your hands shoved under his shirt which was no longer tucked in his jeans. His arousal was prominent and the bulge in his trousers could not be ignored anymore. Tonight, you would go all the way with him. But you knew you had some convincing to do first.

"Jack," you uttered in between his soft, divine kisses, "shall we move this to the bed?"

Sighing, he knocked his forehead against yours. In his eyes you saw doubt and hesitation like any other night before. You sat up without awaiting an answer and took both his hands in yours so he stood up with you.

"I'll be fine."

The look on his face hadn't changed in the slightest, he looked even more worried now that he knew you were serious.

He let you lead him to the bedroom where you sat down on the edge of the bed, looking up at him with those eyes he couldn't say no to.

"Doll," Jack whispered, "This is about you. We won't do anything you're not comfortable with. So if you want to just make out, we'll do that." You smiled at how agitated he seemed, yet you were the one who should be nervous, right?

Finally, Jack gave in and hovered over you, his mouth hung open as he admired the shape of your body. Hands traveling in slow motion, he pulled your shirt over your head. Jack wanted it as much as you did and it flattered you how concerned he was with your wellbeing. You were sure you wanted him to be your first.

Jack watched how your hands unbuttoned his shirt, you had seen him topless before but this was different. The smooth skin under your hands felt divine and you were keen to touch every inch of his exposed chest by running your hands all over it. He seemed to enjoy your light touches, Jack hummed in appreciation as you moved your hands up to slide them into his hair. He kept his own bottoms on but removed yours, marvelling at the view of you in just your underwear. You were exposed to him but you didn't mind, it felt great how his eyes rested on your shape, glistening with arousal. Jack carefully took off your bra and smiled to himself, peppering your breasts and pointed nipples with warm, open mouthed kisses. He slowly worked his way down your chest and stomach, hooking his fingers under the material of your knickers and inch-by-inch pulling them down to leave you completely naked. You shivered in delight when his fingers slid up your inner legs, stopping at the edge of your bum. Cautiously, Jack spread your legs.

His deep brown eyes met yours once more before he started his actions. Feather light kisses were covering every inch of your core, anticipation was quickly building up and you felt yourself getting moister by the second. His warm tongue touched your folds and you started melting beneath him. Your eyes closed at the feeling of him licking you, devouring your wetness and spoiling you with heavenly movements in the precisely right places. Your entire body was tensed up- but in a good way, a way full of desire and longing for that man between your thighs who somehow knew exactly what pleased you. The sensations were so overwhelming, Jack had you whimpering and moaning in no time, the feelings increased when he entered you with his index finger and curled it just right to hit a pleasurable spot inside you. It all felt so good and you didn't know what to do with your hands, so you grabbed fistfuls of the bed sheets. A warm and tingling feeling was approaching in the pit of your stomach and you knew you were close.

"Jack, I'm going to-" you began, but the rest of the sentence stuck in your throat when your intense orgasm washed over you.

All the strength had left your body with your climax and so you were a weak, panting mess on the bed. Jack crept up to you, smiling broadly at what he was capable of making you feel.

"Did you enjoy that?" His hot breath tickled your ear when he spoke.

"God, yes."

"So did I."

You grabbed his chin to slam your lips onto his, moaning again at the taste of yourself on his tongue.

The only thing on your mind now was to return the favour, but after Jack had taken off his jeans he gently took your wrist when you reached down into his boxers. He softly peppered your hands with kisses and knocked his forehead against yours.

"Doll, you don't have to," he whispered against your lips. As a response you smiled and freed your hand from his grip only to slide it downwards. You lightly rubbed your fingertips over his clothed erection at which Jack hissed, only encouraging you to keep going. You pushed his boxers down and he helped you, laying down beside you. When you caught sight of his member you gasped- shape and size were absolutely admirable, yet you silently wondered if it would hurt.

Now your eager hands explored his body, finally coming to rest at this erection. It felt solid and smooth at your touch when your wrapped your fingers around it. Jack watched you contently, smiling, when you gently began caressing his member with long strokes, gradually getting faster. You enjoyed his reaction, his eyes were now shut and moans escaped his lips, you were obviously quite good at what you were doing.

At some point, Jack moved over you again, his lips capturing yours in a heavenly soft, yet demanding kiss.

It was time.

"Are you sure you want this?" Jack's forehead creased while he covered his length in a condom.

You simply nodded, though your heart was now beating up to your throat in anticipation and excitement.

Jack lined his tip up with your entrance and hesitated once more. In order to soothe him, you gently ran a hand through his hair and your eyes met his. The worried glint in his eyes was unmistakable.

"I'm fine, Jack."

"I don't want to hurt you."

"Be slow. I'm fine," you felt the urge to repeat the last bit to take all the worries off of him. A deep sigh left his lips and he sank into you like you had told him, very slowly. His concerned gaze lingered on you for every moment. The feeling was exceptional and you craved every inch, impatiently waiting until he was fully inside you. He checked your facial expression for any signs of being unwell and proceeded his movements when he was sure everything was alright. At first it felt a little uncomfortable when he moved in and out of you and you tried your best not to show him, but gradually the feeling improved and turned into an incredibly pleasurable sensation. The wetness that had formed with your previous orgasm made it easy for Jack to maintain a steady, yet slow rhythm.

His eyes still had not left yours for one single second, carefully examining your face. You weren't certain whether you would be able to enjoy another orgasm just yet so your focus lay solely on Jack, his body seemed to tense more up with every thrust.

"You feel so good," he mumbled against your temple before pressing another heated kiss to your lips. A soft smile spread on your face, he finally came with another two strokes, his face buried in your neck.

Jack lay still for a moment, his heartbeat against yours gradually slowed and somehow became one with yours. Being there with him felt just divine and you wished you could stay like this forever. However, Jack eventually rose from the bed, removing himself out of you, "I'll be right back, doll."

He kissed you briefly before he disappeared in the bathroom, only to return to bed seconds later. Your face lit up with happiness when he gathered you in his arms, pressing your warm body against his so tightly it almost hurt. His deep brown eyes sparkled uncontrollably when he looked down on you.

"Thank you for this, Jack," you uttered softly, honestly graceful for this overwhelming experience. You really couldn't have wished for a better man or moment for this very special occasion. Without words, Jack was able to answer and express what he felt for you with a single kiss in which he seemed to put all the passion and adoration he had for you. Indeed you were a very, very lucky woman.

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