Jack Thurlow x Inexperienced Reader NSFW Headcanons
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Summary: The Reader is very inexperienced / a virgin and has their first time with Jack, who is dead set on making it a night you'll never forget
Warning: NSFW, Unprotected P in V, emotional manipulation, Oral Fem!Receiving, Fingering, Cunnilingus
If you were to find yourself in Jack Thurlow’s bedroom, telling him that you’d either never done anything more than kissing, or that you had very little experience when it comes to physical relationships, you’d be in for the night of your life.
The thought of being your first would stir something deep inside of Jack. Something primal and possessive that would overwhelm his thoughts in such an all-consuming kind of way. You would belong to him if he staked this claim on you. He knew it in his bones.
This man is smart. Smart enough to know that most people feel an everlasting connection and longing for their first. If you were willing to give yourself to him, he knew that he’d be able to have you wrapped around his finger in no time. You’d get attached and fall in love with him if you hadn’t already. It didn’t matter how fucked up he was or how many times he snapped at you for seemingly no reason. You still would keep coming back to him because, at the end of the day, he was your first.
He’d be so sweet about it at first. Kiss you softly and slowly rid you of your clothes, layer by layer, until you were completely nude, staring up at him with pink cheeks and a little nervous smile.
Jack would sit back and really drink you in, scanning your body from head to toe while licking his lips. You might clock the predatory look in his eye while he does this, but really, I think you’d be a little too focused on the fact that you were naked and dying to be touched. You’d wonder how your body could yearn for something it had never felt.
When he finally does touch you, He’d work his way down, kissing down the sides of your neck, licking and sucking on the skin, leaving behind red welts that would turn to bruises before morning. He’d gently caress the curve of your breast, rolling your nipple between his thumb and forfinger on one side while pressing open mouthed, wet kissed to your tits. He’d knead the skin, not too hard, but hard enough that it would make you gasp.
He’d want to make you cum before having you touch him. To give you a taste of the blissful feeling and show you what you could have as a reward if you’re good for him. He won’t outright say this, of course not. Not yet, at least. He’d need you to be worked up and malleable if he’s really wanting to get inside your head.
Jack would tease you, lapping at your clit while you writhe and moan under his touch. He’d keep asking you, ‘Does that feel good?’ and ‘Do you like that, princess?’. You’d nod eagerly, already falling apart under his touch by the time he eases a finger into your sopping hole.
The praise would go crazy at this point. His voice would be sweet like honey and you’d be eating that shit up.
“That’s it, angel, you’re taking my finger so good. How about another one?”
“So wet for me, such a pretty little pussy.”
“Good girl, one more? Let me make you feel good.”
He’d make sure you came so hard that you were seeing stars, his name falling from your lips like a prayer.
Then, while you’re coming down from your high, he’d strip off his own clothes, take your hand, and wrap it around his cock. He’d keep his hand over yours, showing you how he wants you to jerk him off, continuing with the praise. You’d be floating back down to earth after a mind-shattering orgasm and be so eager to please the man who had just brought you to it that you’d do anything.
Jack would have you right where he wants you. He wouldn’t have you give him head. Not the first time. He knows that he wouldn’t have the self-control not to slam himself into the back of your throat, and you just weren’t ready for that yet.
He’d nestle himself in between your thighs and run his tip through your folds, watching with great interest and with a surprising amount of self-control as you rub yourself against him, desperate for friction, a whiny mess. He’d wait until you’re begging him to fuck you before lining himself up with your entrance.
This man would hold your stare while he’s slowly sinking into you. He’d be careful not to hurt you, and he’d stop every few inches to let you adjust, telling you how good you were doing and how good you were making him feel. He’d save the last inch of depth. Wouldn’t get there initially, and you’d be none the wiser.
He’d wait for you to give him the go ahead to start moving and would be gentle, withdrawing halfway, then slowly burying himself inside your warm cunt. At this point, he would be starting to lose his composure. The sounds you’d be making and the feeling of your walls wrapped around him, so tight and slick from your arousal, would ruin him.
Once you start really getting into it. He would completely lose control.
He’d rut into you like an animal, slamming himself into you all the way to the hilt so hard that it would take your breath away. His tip would bash against your cervix, and you’d cry out, biting down on his shoulder or clawing at his back as tears welled up in your eyes.
“You’re taking me so well.”
“Come on, princess, you can do it.”
“I know it hurts, but just give it a minute, you’ll love it. You just have to get used to it.”
“That’s it, baby, I can feel you getting worked up, are you gonna be a good girl for me?”
He’d stop if you asked him to. Of course, he would. He wants this to be a good experience for you. For you to associate him with feelings of pleasure and good memories. But, he also wants you to go home and think about how much you’d liked him manhandling you, trying to figure out why it turned you on so much. He needed you to come back for more.
You’ll reach a point where you’re close to tapping out, and he’d know the moment you start thinking about it. He’ll be quick to slide his hand in between your glistening bodies and start working your clit. Smiling into the side of your throat when you start panting.
You’d cum, hard. Way harder than the first time, shaking and clinging to him while your cunt clamped down around his cock, convulsing as he pumped you full of cum. You’d be so fucked out that you could barely breathe, tears streaming down your cheeks, breathing raggedly and twitching.
He’d hold you. As long as you needed him to. He’d let his cock soften inside of your, keeping you wrapped up in those big, strong arms of his and he’d mutter praise into your ear, telling you how good you’d done and how he’d found the whole thing so, incredibly hot. He’d tell you that you’re the best fuck he’s ever had and that he couldn’t wait to do this with you all the time.
When you finally recover, he’ll run you a bath and clean you up. This would probably be the only time he’d ever do this for you. He’d want you to yearn for this kind of treatment.
I’ve seen a few people mention that they were surprised with Marcus’ behavior and expected to like him more but here’s the thing, we aren’t supposed to like him. He doesn’t feel right because he’s not supposed to. He’s a classic example of the grass is greener on the other side, he represents everything that Willie isn’t. He’s not royal or rich, he doesn’t hide who he is, he doesn’t expect Simon to keep their relationship a secret. We all knew Willie and Simon were going to end up together, Marcus is just a plot device to show us (and Simon) that he still wants to be with Willie.
Summery: Going to a diner to destress, they find someone who changes their world.
tw: Depressive thoughts in the beginning, kinda toxic themes at the end lowkey, obsessive behavior, I mean this is the riddler we’re talking about, kinda suggestive at the end, but not too badly
a/n: So at the beginning it was self indulgent about myself...but uh...I kinda got carried away at the end.
wc: 1.5k
Master List
Kissing my teeth, I couldn’t stop the sigh that escaped my lips. The amount of work I have to do was exhausting to even just think about. Especially when I don’t have the energy to do anything. My current mindset wasn’t in the best place, as I felt like I could barely get out of bed without struggle.
So that’s why I currently found myself at a small diner. I passed by it all the time on my way to and from work, and I always wanted to go. I just never had the time, and I technically still don’t. But I’m human and I deserve rest as well.
As I entered, the bell rang, alerting the staff of a new customer. Looking around it wasn’t that busy, and I didn’t see any sign that said to wait to be seated. So I took a seat at a booth by the window.
Tapping the table as a anxious habit, I took another look around the small diner, there were only two other people inside. One was an older guy who seemed to be in a bad mood as he sipped on his coffee (I assume). The other was a younger looking guy who had a dorky vibe. He was kinda cute. Not wanting to stare any longer, afraid he might see me as weird, I turned to look outside and opted to people watch instead.
After a minute an older lady came and took my order. I relaxed a little, the diner had a homey soothing smell. Something I wasn’t all used to in Gotham. The smooth jazz playing on the radio also helped calm my nerves. I started to slightly dissociate, thinking about nothing yet everything at the same time.
Of course my mind started to go into a depressive road. How all my friends stopped talking to me after high school, how lonely and sad I felt. How I do the same thing every day and this was the first time I did something new. I felt my mood drop once more.
I was knocked out of my stupor when the waitress placed my order on my table. I smiled up at her and she sent me a smirk.
Then she proceeded to say, “I think you caught someone's eye.” Her eyes dart to the young man at the bar table who quickly looks away. I felt a small rush course through me as I looked down at my beverage. A small smile made its way onto my face unconsciously as I fiddled with my hands.
“I’m sure its just a coincidence,” I shrugged. Even as I said that, I still couldn’t help but feel giddy. The thought of catching someones attention was something foreign. I always blended in my school career, only really talking with friends I made in middle school. We grew apart obviously after high school ended. At work I still blended in. Doing my work as asked and nothing more.
“I’m not so sure,” The waitress whispered. “He’s a regular and hasn’t looked at anyone else as much as this. Just keep it on your mind.” With that she walked away.
I glanced once more at the man once more before focusing on my food. The waitress successfully found my distraction as now all I could think about was how this man may possibly find me attractive. Now I didn’t think I thrived off of male validation or validation of others in general, but receiving it none the less still made me feel good. It was something I didn’t receive.
Eating the food I ordered, my mind spiralled. He didn’t seem like the type to make a first move, and I’m definitely not the kind to make a first move. So I concluded that nothing was going to happen. Looking up once again at the dorky man and our eyes met. Once again he quickly ducked his head down, and I felt my heart speed up a little. Now I’m not the type to fall in love right away, I do have standards, but I can have a small crush/find someone attractive. And he was, he had clear framed glasses and wore an oversized green jacket.
Maybe I should try and talk to him. Nothing I could lose...well except my life. Gotham has the strangest characters, never want to say the wrong thing to the wrong person. But he didn’t seem like the person to hurt a fly.
Deciding to gather up the little amount of courage that I totally didn’t have, I got up and took my drink and food and walked over to the stranger that gained my attention.
“Hey,” I said quietly. “Is it alright if I sit next to you?” The man looked up with wide eyes, his mouth slightly parted like he was in awe. Quickly, he nodded in response and I took my seat next to him, setting down my food. I fidgeted with my hands and looked down at the bar. What do I say or do next? I haven’t made friends with someone since 6th grade. “I’m (y/n),” I said awkwardly after a slight awkward silence. “What’s your name?”
He seemed to be in shock as I looked back up at him. I noticed how his hair was a sandy blond color, and he had a slightly chubby face. Cute.
“E-edward,” He finally replied back, slightly stuttering.
“Nice to meet you,” I replied.
That was how I first met someone truly ground braking.
~~~~
I never got his number, or any way to contact him. I mean it took all my courage to talk to him. So I frequented the little diner more often, hoping to see the man named Edward once more. And I did in fact run into him quicker than I thought I would. It was actually the second time I went there. I felt myself stand straighter when I saw that familier bad posture.
“Edward!” I greeted when I sat next to him (which seemed to startle him). “Long time no see.” He nodded and tilted his head downward towards the table.
The same waitress came by and took my order once more, leaving with a sly wink. I felt myself warm up at the implication. Glancing at Edward, I noticed that he seemed busy, so I busied myself on my phone as to not bother him. I scrolled mindlessly on social media as I absent mindedly ate my food. Normally I would feel awkward, but it was nice to just sit in silence. The looming anxiety of small talk no where to be found.
Yet I found myself refreshing the page over and over as I seemingly ran out of content. Looking again towards Edward, I noticed that he seemed to be dazed.
“What’cha doing?” I asked, tilting my head slightly. This seemed to snapped him out of his stupor as he whipped his head up towards me. A nervous grin overtook his features as he shrugged lightly.
“Just some things for work,” He spoke out. His voiced matched his appearance perfectly.
“What’s your job?” I asked, the conversation coming out more naturally now.
“Forensic accountant,” He sighed out, like it was a chore for him to even mention the occupation.
“Hmmm,” I hummed out, nodding. “What do you do exactly?”
Once again, he gave me a weird look of seemingly utter adoration. It was something I wasn’t used to, though it feels like something I never want to get rid of. After so long of not being seen, and being in the background, I finally felt seen. It felt good. But that also made me wonder if I liked Edward for who he was as a person, or if I just liked the attention he gave me. I personally think it’s a mix of both, since from what I’ve seen, he’s a shy, but sweet person.
I zoned out slightly as he explained what he did, his voice soothing to listen to. Hearing it couldn’t help but make me smile. This time I was knocked out of my stupor as he asked me about my own job.
With that, we got to know each other better and I even managed to get his number. When I arrived home I texted him ‘Hope you got home safe, have a good night! :)’.
~~~~
I thought the worst would happen, I receive a cute guys number and he just doesn’t text me back or the responses are really dry. That’s happened to me before and it hurt slightly. So when Eddie actually responded back with a cute message, but also kept conversation flowing with me seemingly easier over the phone.
I could understand that. The only people I really talk to anymore are my online friends I made when I was younger. Talking to people online was easier than face to face. This also lead to Eddie and me becoming closer, meeting up at different places, or just spending hours over text or calls and talking to each other.
~~~~
I couldn’t help but laugh a little as Eddie excitedly looked at me as he explained a riddle to me. A look of insecurity passed over his features before he stopped and asked “What’s funny?” He almost looked like a hurt puppy.
“I...I just find you cute when you get excited over puzzles and riddles,” I shrugged, slightly curling in on myself as I was never this forward before. We were currently at my house in my living room just talking with the tv on in the background.
As I said that, Eddie’s face flushed red as he glanced away. I felt my heart pump faster and smile slightly at his reaction. He brought out the more dominate side of me that I thought I didn’t have. I mean someone has to take the reigns of this double shy and anxious friendship. Besides, the way he was so reactive helped my ego and confidence.
“Sorry for interrupting,” I said finally after some time of silently observing his flushed state. “As you were saying?”
Yet what I saw was something I haven’t seen from Eddie before. He was just staring at me with his flushed and nearly obsessive stare. Complete and utter adoration across his feature, almost looking unhealthy. I felt my nerves alight, a feeling I’ve never felt before. It wasn’t bad, in fact I craved more.
“Y-you really think I’m cute?” Eddie whispered out, like if he was any louder he would wake up from a dream.
I nodded with a shy smile, “Of course, I have since we first met.”
His breathing seemed to get slightly heavier, and he crawled towards my side of the couch slightly, “P-please say it again.”
“I...I think your cute?” I said in more of a question like tone. It looked like he was gonna burst, he was shaking slightly and it almost looked like he was worshipping me.
I felt this overwhelming feeling of power. Not one where I would abuse, just a power over someone I was never given before. Someone who was opening up themselves for me. And honestly...I think he held that power over me as well. A tension filled the room, something I haven’t dealt with before. I didn’t know what I wanted to do, but one thought was on my mind. Seeing Eddie in front of me, like an offering...I just wanted to kiss him, feel his lips on mine, taste him.
So I listened to my heart. Grabbing the back of Eddie’s neck, I silently asked him for permission. Permission which he needingly gave me, like he would die without my touch. So I gave him what he seemed to crave, and something I craved too.
I kissed him deeply, something he reciprocated with vigor. Basically moaning into my mouth, whining at my touch.
All I could feel was the heat rushing through me at the power I held over him...
Lowkey the jayrose relationship in future state is portrayed in a really unhealthy manner. Like this is what i sometimes dislike about the ship. sometimes its portrayed good (dceased) or like future state which is kind of a fucked up portrayal of it but thats just me.
I love you I love you I love you so much!!! I can't live without you but I want to impulsively break up with you? Or argue till I turn blue 💙 but I need you in my life I need you so bad I will die without you so ill be good and do whatever I can to keep you by my side okay??
i hate to wish pain upon my partner.. i dont want to hope and pray on ever star and every god that someone breaks her heart so she could be with me. i dislike it when i convince everyone around her they are not needed, and that they'd all be better off without her. of course i dont want to hold her when she's doubting if shes loved. she is, by me, and only by me. -✨🌸☁
