Imaginary Boyfriend: Gentleman Jack 2 (rough draft)

When your grandfather had passed away, you made sure to collect that old cigar box that had originally inspired Gentleman Jack. You had often gone back to it, hiding things inside for later. Everything was still intact, the pressed flower from the crown Jack had made you, the skipping stone you refused to toss across the pond, the feather you had found on a particularly bad day. You took it home, along with some other memorabilia from your grandparents place.

The cigar box sat prominently on your shelf for a long time, eventually being covered by books and sketch-pads over the years. Occasionally, you would have a rotten day and pull out the cigar box to go through good memories. The stone had become smooth over time from where you had rubbed it so much. You had put the pressed flower in between sheets of tape because it was starting to fall apart. There were new things added too, like the first drawing Jesse ever made for you, a miniature of a statue from a museum you took Jesse on her fifth birthday, a tiny plastic baby bottle from your mom’s babyshower. There were also some concert tickets, a locket from a high school best friend, as well as a note from the gender identity support group you frequented. 

These were the things you went to, to make yourself cheer up and feel better. Each little, seemingly insignificant, thing inside was a different memory that was well worn with time and comfortable to move through even on the sharpest of days. The box itself was a memory, a loving one about the best friend you ever had, family, and the rainy day where boredom led to creation.

Taking out this box again, it was not because it was a bad day, in fact the day was shaping up to be a good one, but because you wanted to share. You wanted to stroll through memory lane with Jack, show him the old things that you shared with him, the new things you shared with others, and hopefully a place where you could keep new memories. 

That morning you had seen your family off to Jesse’s first mathlete competition. Jesse had always been very smart, especially when it came to numbers. Your step-dad liked to joke that you always had your head in the clouds, and Jesse had hers in books. Which was very true. 

“I’ll call you later,” Jesse says, barely able to contain her excitement. 

“Just keep these two in line for me,” you motion to your parents. You hug her tight and wish her luck. “No matter what happens, we’ll go out for pizza when you get back.”

Jesse beams then urges you closer. “You and Jack have fun, okay?”

Why is she making this secretive, you wonder? 

“I’m sure we will.” You laugh.

Jesse goes and hugs Jack, whispering to him the same way he did to you. You stand by Jack as the car pulls away, waving goodbye until they’re out of sight.

You sigh and cross your arms as you both go back into the house. “If I didn’t know that rugrat any better, I say she’s trying to play matchmaker.”

Jack nods and turns to you.

“I mean I guess it worked,” you scoff. “But what does she have to gain from this?”

Jack taps his finger-tips over his chest then pats your chest, placing his hands together to form a heart.

“You’re an imaginary friend though, are you sure this isn’t too weird?” I pout slightly. “I mean, I know it happens, but people tend to think it’s some sort of weird kink or something.”

Jack shrugs.

“No, you’re the only one, so I don’t consider it a kink.” You look up at him, feeling his gaze fall softly upon you. “But I did create you, don’t you think that that is a bit weird?

Jack tilts his head to the side and presses his finger against the side of his mouth as he thinks. He then raises his hand, stretching out his fingers before flourishing his hand and bowing before you.

“I don’t get it,” you murmur.

Jack sighs and takes out his notepad. He scribbles down then hands it over to me.

‘You made me to always be the best companion to you, no matter what happens. Now that we are together again, I am your companion, still the best, still for you.’ You look back up at him, heart pulsing, cheeks flushed. 

“So imaginary friends can evolve for their creator?”

Jack nods and lays his hand over his chest.

“Then that means, instead of being my imaginary friend, you would become my imaginary boyfriend.” You smile at the silly notion of the words, but not the idea of it.

Jack places his hand on the small of your back and nods.

“Is that even possible?” Your eyes flash down for the briefest of moments. “I mean…” You then shake your head. “Nevermind, I’m being weird now.”

Jack kisses your forehead then bops the tip of your nose. He then presses his lips to your ear and you hear a low, seductive snarl.

“Oh!” You exclaim and break into a giddy smile. “Is that so?”

Jack licks your cheek and ear, his long tongue following it’s contours before he bites your neck with sharp teeth. You choke back the moan in your throat and cover it with a warbly laugh. 

You press your palm to his chest. “Easy tiger.” 

You gulp and give him an awkward smile. “We do have a date tonight, after all.”

Jack bows before you with a flourish then rises. He takes a card from inside his jacket and hands it to you. Inside is an instruction for you to follow, starting at three that afternoon.

“You’ve really got all this planned out!” You remark.

Jack signs, which you’re now able to understand most of. 

“You want this to be the best day? You could have just watched cartoons with me on the sofa,” you chuckle.

Jack pulls you close, giving you a soft, loving kiss. He kisses the tip of your nose, then steals it like he used to. 

“I’ll follow the list, don’t worry,” you giggle. “But we do have until three when I have to start. What did you have planned until then?”

Jack places his hand on your back again, leading you to the kitchen. He makes you breakfast, chopping up fruits and making waffles from scratch. This was something he used to do when your mom had work early, or ran late depending. 

After breakfast, you do watch cartoons on the sofa. You start to doze off, so when you do, Jack picks you up and carries you to bed. Half asleep, you grab his hand as he starts to go away. 

“You don’t have to go,” you murmur sleepily.

Jack looks down and tightens his hand. He eases down onto the bed, though his long legs hang over the end. You snuggle up to his chest, draping your arm around him. His palm glides up and down your back, coaxing you into a warm, relaxed bliss.

Eventually, Jack eases you back to awake. He sits you up in bed and pats your cheeks as you come to.

“Is it three?” You yawn.

Jack nods and hands you back the card containing your first instruction. He kisses your forehead then saunters out of the room.

You rub your eyes and open the card. “At three o’clock sharp you will proceed to the bakery where you will pick up an order under your name, also enjoy your favorite donut while you are there and a coffee or tea if so desired. You have an hour before you have to return home for step two.”

You change and get ready to go, finding that Jack is already busying himself with something in the kitchen. He shoos you away in a hurry when he catches you watching. You chuckle to yourself and leave, heading to the bakery. 

You do enjoy a cruller while you are there, and a cinnamon bun iced latte. The order you pick up is wrapped in pink paper, probably so you do not peek at what is inside. Attached to the box is the next step in your routine.

“Once you return home, hand the box over to Gentleman Jack who will take care of it from there. You will then go immediately to the bathroom, where you will find your next card to tell you what to do.”

“Something in the bathroom,” you murmur to yourself. “How very interesting.”

You return home and hand over the box to Jack who inspects it.

“I didn’t try to peek, but I did shake it a bit.”

He stiffens and stares at you harshly.

You raise your hands in defense. “I’m joking, promise.”

He points to the bathroom with a sharp finger and you smirk. 

“I’m going, I’m going.” You turn, heading to the bathroom. Upon opening the door you see candles lit, and the tub is steaming. There’s a soft aroma wafting in the air, a mix of lavender and eucalyptus. The bathroom has been cleaned and emptied of most of the clutter to make it feel more airy. A robe hangs on the door with the next note attached.

“It is time to relax. Sink into the tub and enjoy the peace and quiet. I will turn on music for you. There is a bathbomb on the side of the tub, it contains the next instruction.”

You smile as you undress, sinking into the water and letting out a relaxed grunt. “How nice.” You find the bathbomb, it’s scent is heavy and the colors match the nonbinary flag. Your smile grows and you plop it into the water. The colors froth, mix, and swirl, creating a vivid purple shade in the water. The note floats to the top and is folded into a tiny square wrapped in plastic.

You peel away the plastic, opening up the note. 

“I will knock on the door when the next step is ready. Take the robe and go to your room where I have laid out an outfit for you, as well as a new sketch pad and some art supplies. Take some time to draw something between getting dressed and when I come calling.”

You hadn’t bought a new art pad in ages. You hadn’t really done any artwork aside from the occasional doodle in forever either. You had always wanted to create your own comic or cartoon when you were little, as all you ever did was watch cartoons. But you never got the chance, and over time, things got in the way.You had accepted these things might never happen, but you would make sure that Jesse never suffered that sort of block.

After a while, Jack knocks on the door. You step out of your purple void and dry off, slipping on the robe. As you step out, Jack gives you a drink and a kiss, ushering you off to your room.

He then signs before opening your door. “Fun?”

“Yeah, I’m having fun,” you smile. “But my curiosity is running wild.”

Jack kisses you again, opening your door and pulling away as the kiss begins to deepen. He motions to your bed where you see a box with a big yellow bow leaned on your pillow. He closes the door as you sit down on the bed.

Inside there is a button down shirt with a rose and beetle print, a fitted blazer that matches the color of the roses. There’s also a pair of high waisted, black pants, and a small necklace with a tiny beetle charm.

You get dressed, even doing your brows so your eyes stand out more. The outfit looks amazing, just exactly your style with a bit of flare you’re sometimes afraid to wear. The high waisted pants make your tiny legs look extra long, and the red blazer makes you feel like you have some sort of build. 

Under the clothes in the box, there is the new art pad with a box of colored pencils, charcoal, and fancy pens and pencils. On the first page of the sketch pad, the next note is written.

“The next step is easy, draw something while you wait.” Under that, there is another note written by Jesse.

“I miss seeing you draw, I miss having your pictures to hang on my wall. I miss seeing you create stuff. Gentleman Jack and I both agree you need to do this again and never stop. I love you so much! You’re the best sibling in the whole world.”

Tears spike in your eyes, you had no idea that she even paid attention to that. You sniffle and take out the pencils. You get to drawing, feeling a little shaky at first. You doodle as you warm up, slowly creating a set of character sketches. Ideas begin to flow, childlike wonder erupts in your heart as that excitement of inspiration flows through you freely. Once blocked by a monumental dam, it now breaks free, spilling onto the page.

There is a knock and Gentleman Jack opens the door.

You lift your head from your creativity, not realizing time has passed at all. The side of your hand is covered in black and there are pages now filled with your first artwork in ages. 

Jack extends his hand to you and you smile brightly. “You and Jesse planned this all along, didn’t you?”

Jack kisses your hand despite the stain of pencil marks. He strokes your arm and leads you into the kitchen.

The candles from the bathroom now decorate the kitchen. The candlelight is warm and welcoming as you sit down at the table. Jack begins to serve, placing a small salad before you and pouring a glass of wine.

“I don’t drink,” you try to quickly cover.

Jack taps the glass, asking you to try it.

You sip and find that the drink is a peach juice. “Oh, good,” you giggle. You raise your glass as he sits down. “This all seems too nice! You didn’t have to go all out.”

Jack nods then presses his finger to your lips. He watches as you eat then he stands and turns on classical music. After the salad he serves french onion soup in a tiny bread bowl. You’re already getting full but there is still the main course and dessert to go through. 

For dinner he serves your favorite, a big slab of lasagna. You squeal happily and dig in, forgetting you were anywhere near full.

“This is so good.” You take a sip of the peach juice and beam. “I’m having such a good time.”

Jack gives you a kiss on the cheek and you hear that low growl again.

As you’re finishing up, Jack takes the box from the bakery and opens it. Inside is a chocolate cheesecake covered in raspberries. 

“Oh wow!” You marvel.

Jack serves a slice as he clears away your plate. He also serves you a cup of coffee.

“Is it okay if I save this for later?” You ask timidly. “I know you probably have an order for the evening, but I’m so full.”

Jack nods and pats the top of your head. He wraps up the plate and sets it into the fridge. You do enjoy the coffee though, taking a few sips as Jack begins to blow out some of the candles to give the room more ambiance.

He turns up the music then turns and offers his hand to you.

“A dance?” You stand, moving into his clutches. Just like that night before, he leads you into the dance. You go slow, almost not moving at all. You rest your head upon his chest, sighing softly as you sway.

Jack then stills and slips his fingers under your chin. He lifts your head and you close your eyes, tilting your head to accept his kiss. His tongue darts over your lips, then down along your jaw. His growl trembles along your skin and you clutch to the front of his jacket. You feel the next card in his front pocket.

You take the card and read it over. “Your choice from here on out, I am yours and will do all you ask of me.”

You swallow your heart back down and gaze up at him, heart pounding, head spinning. You kiss him again, capturing the back of his head.

“Bedroom,” you whisper to him. “I want you, now.”

Jack scoops you up off the floor, carrying you to the bedroom. He lays you down upon the bed and you pull him on top of you.

“Take off my clothes,” you moan. “Touch me. All of me.”

The growl grows louder as he unbuttons the blazer and your shirt. His fingers drag over your chest, down your small breasts and to the buttons of your pants. He kisses you hungrily, slurping your tongue, biting your lip, nibbling your ear. The growl grows deeper as he looks down upon you half naked.

“What about you?” Your voice warbles. You sit up, removing your shirt. You press your chest to his and claw your hand down. “What will I find?”

Gentleman Jack grins, revealing his sharp, pure white teeth. As your palm reaches below, your fingers sink inside. You then pull something out from the dark void of his body. It’s heavy and fills your hand. It grows warmer as you stroke it, velvety in texture, thick, and throbbing.

“Oh my,” you breathe.

Jack grabs your shoulders and eases you back down onto the bed. He rolls you over, stripping away your pants and underwear. He grabs your ass, squeezing it and digging his fingers into it. You whimper, burying your face into the pillow to hide your pleasured sounds. His hands stroke down your thighs, opening your legs up and arching your hips more. He then goes still, breathing as he waits.

You moan, turning your head away from the pillow. “Don’t stop.”

He smirks at you.

You bite your lip. He wants you to tell him everything, to command him. You raise your ass up more. “Please, spank me a little.”

Jack growls and his hand rubs to your rear, squeezing it then releasing before giving you a sound pop. You bite your lip harder and arch your back. “Again.”

He strikes the other cheek.

“Harder!” Your voice comes out louder.

Jack’s slap sends electric currents through your spine and legs. He rubs the red mark he’s left, dipping down to kiss it and lather his tongue over it.

“Keep licking,” you mewl. “Right there.”

His tongue presses between your cheeks, going down to the folds between your thighs. He grips your ass hard, spreading you open more. His tongue dances over the wetness dripping from those lips, and a strange laugh gurgles in his throat.

“Bite me.”

His sharp teeth sink into your thigh and cheek. He growls, nibbling and sucking before biting again.

“Jack,” you whimper blissfully. “That feels so good.”

He spanks again then burrows his tongue deeper, catching the drips that fall from you.

“N-now,” you croak. “I want you inside.”

Jack sits up, placing himself behind you. His shaft rubs to your thigh, your ass. He grips tight around your waist, pulling you back. The dark shape slips between your thighs and you can see it looking down. He rubs against you, coating himself in your wetness. The tip vanishes inside, you feel him moving forward, stretching you, filling you.

“Spank me again,” you moan.

He does so, snarling as his palm claps then rubs gently. 

“Deeper.”

He fits perfectly inside, after all, he was made for you. The pulse inside you flows through your veins, making your limbs quiver and spine radiate. 

You catch your breath, squeezing your muscles tight around him, feeling every inch. He snarls behind you, holding your hips firmly as his own begins to shake.

“Go slow,” you whisper. “Let me feel you.”

He pulses once, twice, taking his time. He rolls his hips, letting you feel even more of him within. You whimper, losing your breath the more he moves.

“Harder,” your commands are growing weak.

He thrusts all at once, shaking you and the bed with his might.

“Harder!” You bleat.

Gentleman Jack jolts again and again, sinking you further into the bed. The headboard beats against the wall, and his snarls grow louder in his chest.

“More!” You cry out. “Oh god, don’t stop!”

Gentleman Jack gives you everything, hammering himself inside you until your crow. He throws you onto your back, pushing your legs up over your head, and he keeps going. 

“Come for me!” You cry out. “I want it all inside me!”

Gentleman Jack bucks and throbs. He arches himself off the bed, straining and opening his mouth wide as a roar comes out. You cry, tears flowing down your cheeks as you can no longer hold out. Your whole body bursts into white-hot radiance, and Jack now melts inside you.

Breathing deeply, you lay there with Jack upon you, his weight and his own breath lulls you into a warm puddle. After a while, Jack lays beside you, stroking your back and hair. You smile and sit up. “Let me rub your back.”

Jack shakes his head and pulls you back down, kissing you softly.

“Then let me show you something.” You take the cigar box from the bedside table and open it. Your hands are still shaky, but you show him each beloved trinket inside.

“This is the box that helped me make you,” you tell him. “And everything inside is another good memory I cherish.”

Jack holds the feather between his fingers then gives you a loving kiss.

“I want every letter from tonight to go inside.” You cup his face in your palm. “And I’m sure there will be more from here on out.”

Jack lifts his hands and signs. “I love you.”

“I know,” you coo. “I love you too. I never stopped.”