THIS IS SO GOOD OMLL

THIS IS SO GOOD OMLL

Kinktober 2023 - Day 5

Caught Masturbating with Tommy Shelby

"Caught In The Act"

Smut - Explicit content - NSFW - 18+ only!

Summary: Tommy has somehow fallen through time & made a new life in the modern day with you. He wants more than friendship & an awkward encounter makes you confront that idea.

Warnings: Smut (NSFW) - 18+ ONLY - masturbation, voyeurism, sex toys, dirty talk, swearing, pet names, hair pulling, creampie, vaginal sex, very light dom/sub, a little bit of fluff

Tommy wasn't quite sure what to expect when he opened the door to your small apartment and immediately heard the sound of your voice moaning and whimpering. He immediately went to reach for his weapon, suddenly remembering that he was unarmed. He was still getting used to living in this new century and the fact that he no longer had a reason to be armed.

It was all still a mystery as to how he ended up here. He had no idea how he had taken one breath in 1930 and the next in 2023. Neither did you, but that didn't stop you from helping him. Even though to pretty much anyone else, his story made him sound utterly certifiable. Instead of judging or turning and running the other way, you were kind and caring.

He slowly began approaching your bedroom, and the sound of your voice became louder. The closer he got, the clearer it became that your whimpers were not of pain or fear but of pleasure. He had dreamt about hearing you make sounds like that since the moment he first met you. 

You had been so sweet to him since he ended up here. You showed him kindness in a way he was completely unused to. Allowing him to stay in your spare room and helping him learn to navigate the modern world. He had become quite smitten with you, actually. You had given him the chance of a fresh start. A chance he was determined to seize.

You also weren't afraid of him. You would talk back to him and call him on his bullshit. Your modern feminism serving you quite well when mixed with your sharp wit. He hated to admit that it gave him butterflies when you laughed openly in his face about doing some chore he always thought to be 'woman's work'. He knew damn well you wouldn't be serving him anytime soon, and frankly, he found your demeanor refreshing. 

You were also stunningly beautiful. In a way that was all your own. Tommy Shelby was well accustomed to interacting with and even seducing attractive women. He had been married to two beautiful women. Both Grace and Lizzie were enchanting, but you were a creature from another world entirely. 

All of these things had him utterly spellbound by you. He'd be lying if he said he didn't spend his evenings imagining what it would be like to be yours and for you to be his. He had a suspicion that underneath your sweet exterior was a devil waiting to come out at the most intimate times. He wanted to be the one to unleash it.

He often thought about you sneaking in to join him in the shower after you overheard him stroking himself. Picturing you dropping to your knees in front of him. Staring up at him through your eyelashes. Water droplets starting to roll down your body, your nipples pebbled and at attention from the temperature change. Wanting to help take care of him, since you knew that it was because of you that his cock was throbbing.

It was because of all the fantasies he had about you that he kept walking towards your door. Stopping only momentarily when he saw your door was cracked open. Your voice was now crystal clear as you whined and moaned, but now he could also hear a soft buzzing and a wet sound. There was now no doubt in his mind exactly what you were doing. You were masturbating.

His suit pants tightening at just the thought that he was catching you playing with yourself. He really was trying to turn over a new leaf. To be a better, more respectable man than he had been. He knew that peeking through your open door was the wrong thing to do, but he just couldn't help himself. Not when he was still a devil at heart, and you sounded so angelic.

What he saw when he looked through the cracked door was immediately worth any guilt he may have felt. It was by far the most erotic thing he had ever seen in his entire life. You were naked from the waist down with the t-shirt you had slept in rucked up to expose your breasts. Up on your knees with your face turned to the side and your shoulders pressed down into the mattress, your ass up in the air. Your eyes squeezed shut, and your mouth dropped open. Your hair dishelved and a little sweaty. Both of your hands busy between your legs. 

In his time vibrators and other sex toys were uncommon. Really, they were just being invented. So seeing you with a vibrator in one hand pressed to your clit, and a big fake cock in your other hand  greedily ramming it in and out of your tight little hole was nearly enough to have him cumming on the spot. You were taking what you wanted, what you needed, and doing it with zero shame or hesitation.

He could see the dildo glistening with your slick everytime you pulled it out of your cunt. Judging from the ring of white cream around the base of it, you must have already been fucking yourself for a while. His hand was already moving to palm himself over the fabric of his pants. Gripping his length and wishing his cock was that toy stretching your pussy. Biting his lip to keep from groaning and giving away his presence.

All that went out the window, however, when you started to moan again. Clearly getting closer and closer to another orgasm. Your hips thrusting to meet the toy and the wet squelch of your cunt getting louder. As you chased your climax you started to speak. Letting the fantasy in your head spur you closer to cumming. It was what you said that sent Tommy spiraling further into his own lust alongside you.

His name. You said his name.

"Oh fuck, yes Tommy. Right there. Fuck! You feel so good. Need you to make me cum again."

You said his name while you were fucking yourself with your toy. You were imagining your toy was his cock. You wanted him just as badly as he wanted you. No, you said you needed him. Needed, not just wanted him.

He felt his member pulse and leak at your admission. Before he even realized what he was doing, he brought one hand up to rap lightly against your doorframe. Officially announcing his presence before moving to open the door wider. It didn't leave you any less startled by the sudden intrusion at such a private moment. 

He couldn't help the smirk that formed on his face as you scrambled to cover yourself. Pulling your shirt back down to hide your breasts and grabbing at the covers to conceal the mess between your thighs. Quickly trying to stash your toys under your pillow. Not that he couldn't hear the wet suction of your cunt desperately trying to hold onto the dildo as you pulled it out. Or your vibrator still buzzing under the pillow that you were now pretending you didn't hear. Not that you didn't look like you had spent the day fucking yourself silly anyway.

He slowly entered your room. Fully aware of the tent in his pants. Knowing that it gave away the fact that he had been eavesdropping on you. His smirk turned into a grin as he saw you notice his erection. Involuntarily licking your lips. Obviously, still in need of satiating your desires despite your embarrassed blush.

"Tommy, I thought you had gone out. How… how long have you been home? … how long have you been standing at my door?" 

His eyes dropped to the floor momentarily, debating how to answer in a way that wouldn't make you think he was a creep. Even though you both clearly desired the same thing. Now he had discovered that he could give it to you, but only if he played his hand diplomatically. 

"I did go out, but then I came back. Decided that I enjoyed your company far more than anyone else I could have run into. As far as your other questions… I was worried when I came back and heard you moaning. I thought maybe you had fallen, but I was obviously very mistaken. You are definitely not hurt, but you do seem to be in need of help. Help that you seem to want me to offer, and it would be remiss of me not to tell you that I desperately want to provide that help. That I think about you at night and wish I could be in your bed instead of my own. That I daydream about fucking you on every surface of this apartment." 

By now, your mouth had fallen open at his admission. Clearly, you hadn't been expecting him to confess all this. He confidently strode closer to your bed, bringing himself to stand right at the edge of the side where you sat. Your eyes roaming his body before eventually falling back to his bulge before quickly jumping back up to his blue eyes. 

"Now, my beautiful girl, I heard you call out my name before. Pretending that toy that you're hiding was my cock. I'd be surprised if you haven't heard me calling out your name as I fuck my own fist. Pretending I'm fucking your pretty little cunt instead. So I think it's safe to say we both want the same things, but I'll ask anyway. Do you want me like I want you?" 

Tommy moved to sit himself down on the bed in front of you. Bringing one hand up to your cheek and letting his thumb pull lightly on your bottom lip. He could see the lust in your eyes, and you quickly nodded your head. Whispering a soft breathy "yes" that made him smile wider because now he knew he could really have you. 

He brought his other hand to your waist and slowly brought his plush lips to yours. The kiss began soft and tender, but before long, it started to become more heated. Both of you starting to feel the need to finally feel each other grow. 

Tommy carefully lowered you down to lay on the bed. Throwing the covers off of your legs so he could run his hands over the soft flesh of your thighs. One of your hands moving to the longer pieces of his hair and the other starting to toy with the buttons on his crisp white shirt. He still insisted on wearing a suit nearly every day, and you were thankful he had apparently already ditched his waistcoat and jacket before he heard you. 

One by one, you undid the buttons on his shirt. Opening just enough that you could slip your hand inside and feel his bare chest. Your fingers dancing over his dusting of light brown chest hair and the edges of his tattoo. You wanted to rip his clothes off and let him take you. To let him bring your fantasies to life, but you knew that before you lost all sense of self-control, you needed to figure out what exactly this was. So you lightly pushed him back far enough to separate your lips from his. Enough to look into his mesmerizing blue eyes.

"Wait, Tommy, hold on. I'm not the person that just fucks people. I'm not good at the no strings attached thing. If that's what you want this to be then we are better off just finishing this each by ourselves. Pretending neither of us ever saw or said anything."

He chuckled at your statement. Not because it was funny, but in disbelief. Could you really not tell the spell you had him under? Did you really think he would spend so much time thinking about you if he only wanted you for a night?

"Oh no, princess, we do this it means you are mine. It means you are mine, and I am yours. Like I said, I want to fuck you and love you on and against every surface of this apartment. That will take far longer than one night. We do this, there is no getting rid of me." 

With that, he forcefully crashed his lips into yours, desperately trying to convey how badly he truly wanted you. The feeling of your fingernails gripping into his back through his shirt only spurring him on. Like squeezing your heels into the sides of a horse, your actions only making him move faster. 

He reached down to pull your leg up over his hip as he continued to kiss you. Moving down to suck and bite at your neck as he ground his pelvis down against you. Automatically, he could feel the heat from your sex through the fabric of his pants and boxers. Reminding him again of how he had found you. How you were still soaked and ready for him. 

A growl fell from his lips as he bit your neck when the sensation of your slick started to soak through to his cock. Rutting his hips into you harder and pulling the most beautiful gasp from you that turned into a wanton moan. Suddenly any trepidation you had been feeling had fled and your animal urges took over. 

You immediately brought both hands to his shirt and proceeded to rip it open. Sending buttons scattering before shoving it back off of his shoulders so Tommy could discard it. He moved on to his pants just as quickly. Getting the button and zipper undone while he took off his undershirt.

You were just able to shove his pants down to his knees when he pushed you back flat on the bed. Quickly taking off his slacks, leaving him in just his boxers before returning all his attention to you. Slowly dragging his hands up the outsides of your thighs to start pulling your shirt up your body. His eyes studying each new inch of flesh revealed to him.

When your shirt was finally high enough to reveal the treasure hidden between your thighs, you thought Tommy might actually start to drool. You were soaked, and your thighs were messy with your arousal. Your clit was swollen and puffy from your vibrator. Your lips flushed and your hole was still gaping slightly from where you had your dildo buried inside of you. The only thing missing from the picture was the sight of his cum leaking out of you. That would have made it perfect.

"Fucking perfect." 

He whispered under his breath before diving down to pepper your stomach with kisses. Biting at your hip bones and stealing a single taste of your cunt before continuing upward. He knew he would be back with his head between your legs later that night. Right now he couldn't wait to be inside you, but he had to finish getting you naked first.

His lips danced over your soft stomach, and his teeth nipped at your ribcage. Nuzzling his nose at the bottom of your breasts as he started to pull your shirt up over them. Keeping his face close to your skin and reveling in your sweet noises. Adoring every part of your body. Smiling against your skin when you finished pulling your shirt off and threw it to the side. Your body finally completely bare for him.

You were getting impatient with his slow pace. As much as you were enjoying his touch, you had been ready for him to fuck you before he had even entered the room. You tried hard to suppress the needy moans that escaped your lips as he studied every inch of your naked body.

"You are even more beautiful than I fantasized." 

As nice as his compliment felt, you were nearing the end of your rope. You needed to feel him inside you, or else you feared for your sanity.

"You've already got me in bed naked and horny, Thomas. You don't have to lay on the flattery. I'm on the pill so just hurry up and fuck me."

You reached down to grab his erection. Squeezing firmly over the fabric of his boxers before shoving your hand inside to start stroking him. Your whimpers were nearly louder than his as you felt every vein on his length and circled his tip only to find him leaking and wet for you. 

Through staggered breath and the most beautiful groans and growls, he finished his thoughts. His hips started to rut into your hand as pumped his cock perfectly. He mentally thanked the advancements in birth control that he wouldn't have to wait or pull out. Although he always preferred bareback anyway, with both horses and women.

"It's not flattery if it's the truth, and it is the truth. Like I said, I've thought about this. A lot. Now, lay back on the bed for me like a good girl."

You did as he said. Pulling your hand out of his boxers and licking the precum off of your fingertips as you laid yourself out for him. Legs spread and back arched in a sinful tableau just for him. Letting him sit back on his heels and study you for a moment. His eyes devouring every inch of you. 

A cocky smirk on his face, he stared right into your eyes as he pushed his boxer shorts down over his hips. His cock finally free and standing proud. Tommy wasn't sure he had ever actually been this hard before, and it was all because of you. It was all for you. 

You groaned at the sight of his thick cock. It was even bigger than your toy was. Biting your bottom lip and grabbing your own breasts. Toying with your nipples as you thought about how good it was going to feel to finally have his cock inside you after all these months of wanting. 

He didn't break eye contact with you as he gripped his length and gave it a few slow strokes. Using the precum dripping for his flushed red cockhead to prepare himself. Enjoying the feeling of you watching him. Especially now that you knew he spent nearly every night doing just that thinking only of you. 

"Tell me what you want. Tell me what you want me to do. Just like you did with that fake cock of yours." 

Tommy descended on you like a predator caging in its prey. His arms braced on either side of your head. His chest pressed to yours. His cock now shamelessly rubbing against your wet cunt. Sliding up and down against your lips and the ridge of his swollen head teasing your clit. You could hear the wet sounds coming from between you. 

The most desperate noise you ever made pulled from your throat before you could answer. Right before you did exactly what he told you and begged for his cock like you had with your toy. Your eyes pleading for him to finally take you.

"Want your cock inside me, Tommy. Need you to fuck my tight little pussy and make me cum. Want to cum on your cock. Want to feel you cum inside me." 

A growl came from the back of his throat. He was very pleased with how you begged for him. He lowered to nip at your bottom lip. His eyes were nearly black with only a sliver of the normal bright blue remaining. 

"That's a good girl. Normally so nice and sweet and proper, but not in the bedroom, eh? I could get very used to hearing you talk like a slut for me."

He brought one hand to drag down your body. Making sure to stop and tug at your nipple before continuing its path between your bodies. Moving his cock so his fat tip sat right at your opening. 

Slowly starting to push inside of you. With how wet you were, he could almost slip right in. Your warmth engulfing him and making him swear under his breath. No one had ever felt as perfect around him as you did. 

"Oh my God, Tom."

You whined at the stretch of him. Even after spending so much time fucking your toy, Tommy still made you feel delightfully full. His length immediately brushing up against your g-spot that was still swollen from fucking yourself. It felt like he was made for you. His slow shallow thrusts immediately starting to push you towards orgasm, and your moans and whimpers starting to push him towards his.

"Can't believe you were holding this perfect cunt back from me this whole time. Well that's not happening anymore, love. I'm never leaving your pretty little pussy ever again." 

His thrusts started to pick up pace when you greedily nodded and agreed. Pushing his hips into yours with more force as he dropped his head to bite and suck at your neck. One hand coming to dig your nails into his shoulders, and the other was moving to pull at the longer pieces of hair on the top of his head. 

Your own hips starting to roll underneath him to meet his thrusts. The sound of your bare skin slapping together starting to echo around the room with the squelch of your wet cunt as an accent. Both of you already breathing heavily. The realization dawning on both of you as soon as your cunt started squeezing his shaft that this round wasn't going to take very long. Tommy could already feel little spurts of precum dripping from his cock into your cunt each time you contracted around him.

"Oh fuck, darling. I'm so close. Where do you want me to cum? Want me to fill you up princess?"

His declaration made the band start to tighten in your low belly. 

"Fill me up, Tommy. Cum in my pussy, baby. I'm close too. Keep talking to me. You're gonna make me cum." 

An evil smirk on his face as he gave up, trying to hold anything back. His hips starting to piston into you. The headboard of your bed beginning to bang against the wall as Tommy began pounding into you. His intense blue eyes locked with yours and his nose nuzzling against you as he spoke. Urging you on.

"That's it, love. Don't hold back. Let go for me. Fuck, you feel so incredible. Thought about this every night and it's even better than I could have imagined. Feel like this cunt was made for me. Is this my cunt? Cum on my cock and prove it to me, love. Cum for me." 

All it took was his order to send you over the edge. Your back arching and a ragged moan pulled from your chest as your body began to shudder. The feel of you cumming allowing Tommy to finally let go. His last few thrusts becoming sloppy as he followed your lead into orgasmic bliss. The feeling of him shooting his warm load inside your cunt prolonging your own orgasm.

After a moment to catch your breath, Tommy leaned down to place another kiss on your lips. Less heated and hurried but no less passionate. Then he slowly pulled out of you and rolled to the side. Urging you to lift your head so he could thread one around underneath and wrap it around your shoulder. Wanting to hold you close but not wanting to smother you. 

When Tommy finally broke the silence, it startled you a little. Part of you had still expected him to just get up and leave. You certainly weren't expecting him to say what he did. 

"Thank you."

You couldn't help the guffaw that came from your body. Quickly elaborating before he got the wrong idea from your reaction.

"For what, fucking you?"

Luckily, he seemed to find your response funny and gave a chuckle of his own before he elaborated. His voice getting softer as he let down his armor, something he had rarely done before, and let you inside. Rolling over to face you and wrapping one atm around your middle to pull you closer to him. His aquamarine eyes were bright and clear as he looked deeply into your eyes.

"For everything. So technically yes, thank you for fucking me, but more than that thank you for everything else you've done for me. For letting me stay here despite having no idea where I was or how I got here. For trusting me when I know others told you not to. For teaching me how to navigate this world. For giving me a chance. For all of it. Thank you." 

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