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my brain is absolute mush i am in love with him!!!! he tries to get you to send him more photos — and you more than happily oblige — and he guards them like his life depends on it. slowly starts to ask more personal questions, mostly trying to figure out if you have a partner and when he finds out you don’t? the game is on. starts using pet names in his letters here and there, drawing you in deeper and you’re so helpless against him. and then the calls start and he hears your voice and then it’s all he can think about. tries to get you to say certain things — especially his name — for him to tuck away for later when he’s alone with your photo and his hand on his cock and wishing more than anything to have you instead of his fist ):

he thinks himself a good person, all things considered. but knowing you, and knowing you’re out there? no protection, such a sweet and soft thing — it worries him. maybe he asks johnny to try and find you. doesn’t necessarily disclose his true intentions, mostly out of curiosity. but then he starts thinking of when he gets out, how he can meet you, bring you back to his place, knowing he’s the best one to keep you safe and so he uses his time to get a head start so when he’s out he can finally keep you ):

hyperventilating, screaming, projectile vomiting, this, this, this, THISSSSS,

The reason im soooo obsessed with your ask is because 1, you’re a fucking incredible writer and 2, you dived so deep into PrisonPenPal!Simon’s psyche, his such a smart dude and unbelievably manipulative when he needs to be…..

Sorry everyones!! asks are taking so long to get out!! I just want to go into the most detail possible and give everyones ideas justice!! if you're waiting, I promise you its in the works rn <3

TW: mentions of murder, jail, corruption kink, masterbation (Reader & Simon), public masterbation (kinda), phone sex, smut, manipulative!Simon and kinda stalker vibes I guess (not yandere)

PrisonPenPal!Simon masterlist

Regular masterlist

If you think about his sentencing, he purposely played his cards in away that made him the victim without him actually having to act like the victim if that kinda makes sense?

The second he punched that kid he knew he fucked up bad, and then when he saw the blood seeping out of the kids skull and covering the floor, he knew he fucked up really bad.

A normal person would either run, go into hiding, try and resist the arrest, break down and have a panic attack. But he knew this wasn’t time for an emotional response, he needed to start planning what his next step was going to be and how he was going to execute it in a way that favoured him.

His not a psychopath, his 100% capable of feeling and experiencing human emotion and is very emotionally intelligent, but when he needs to be, his actions can be extremely calculated to the point its almost scary.

When he sees your picture though, something definitely clicks in his brain, he just wants more.

If that means more pictures or letters or even a phone call, he just needs it.

I think maybe its something primal as well… his a man at the end of the day, and being locked up for years in an all male prison with all male guards means he hasn’t even seen a women that isn’t a playboy model for fucking agessss

His not dumb either, he knows you put effort into taking that photo for him, he knows you put on a red bra because he told you his favourite colour was red. So the idea that maybe, just maybe you feel the same way, or are at least starting to, really erupts something in him.

But you’re completely right. He wouldn’t show a soul the photo you sent him. He’d go to drastic measures to hide everything :( you sent them to him, you’re writing to him, not anybody else,and he knows that if any of the other inmates found out about you, or god forbid, saw a photo of you, they would have an absolute field day.

He sees how the men his jailed with act when wives, sisters or girlfriends come to visit their loved ones.

He hears their disgusting comments about the women’s bodies, the detailed answers of what they would do if they ever got their hands on them. It always made his throat fill with bile and stomach twist.

Si may not be a perfect man, but talking like that about another mans women? His above that.

Thinking about how they would say the same things about you, how’d they’d all pass the photo around with a dirty smirk on their face and snicker? He wasn’t having that, over his dead fucking body.

He writes back to you keeping it relatively normal, lighthearted and friendly, but he sneaks in a little

“Ya’ boyfriend probably isn’t over the moon ya’ writtin’ someone like me, aye? I mean, if my missus was writin’ to a felon I’d blow my fuckin’ top love, theres gotta’ be somthin’ out there better for ya’ to been doin’, readin’ a book or somthin’ like that. It was lovely puttin’ a face to a name, just seein’ someone so happy makes me smile”

Receiving his letter makes your heart sore, you made him smile.

Obviously you had to send him more photos right? You just wanted to make him smile…. right? :(

You definitely didn’t want to send more because your pussy clenched when he called you “love”

Its definitely not because he was so protective over you, knowing he was so worried about your well-being, always asking if you're doing okay, asking if you’re safe…

“I worry bout’ you out there lovie, ya' gotta keep safe, look after ya’ self”

Getting your friends to help you take more photos for him!!!

Maybe you force them to go on a hike with you… you wear those leggings that make your arse look fantastic, posing in front of a nice view and purposely sticking out your cute little bum, subtly showing it off to the camera…. Showing it off to him :((((

But its just to show him the view!!!!! He hasn’t seen a nice landscape in years!! He deserves it!!

You’re not a dirty girl :( you’re a good girl!! You would never do something so disgusting for a man who’s locked in jail, your daddy would be so disappointed if he knew you were sticking out your arse for a man like Si >:(

Calling over your ex-situationships so they can fuck you, your dildo wasn’t enough anymore, you needed the real thing….you needed Si, but obviously you can’t have him, right? There’s no possible way you could ever experience your biggest fantasy….right?

So other men will just have to do :(((

Having them hold you down and fuck your pussy mediocrely, closing your eyes trying to imagine Si :( maybe even moaning his name accidentally…..

Its never really that enjoyable though, all you can think about is how Si would fill you so much better…technically, you have no evidence to prove that, but his such a gentlemen!! He knows how to speak to a women…he must know how to fuck one as well!!!

It only makes sense….

It makes you so sad… he’d never think about you the same way you think about him >:(

He’d never fantasies about your sloppy cunt the way you fantasies about licking up his fat cock, teasing his tip and ruining your throat as he shoves his meaty dick down it :(((

Rubbing your swollen clit on your pillow as you moan for him, maybe even looking at the grainy photo of his face while you pleasure yourself :(( you’re so disgusting for him, so needy, he would never want a girl as yucky as you….

When Si receives your next letter informing him that you don’t have a boyfriend as well as a photo of you posing for him, that’s when the obsession really begins :3

His not obsessed on a yandere level but his definitely deep into it :)

He never really thought about what he would do after he got out, he always kinda just guessed that he would go back to his old ways, but now he has you very obviously showing some type of interest in him, his mind is fucking racing!!!

Maybe he can get your number and use his monthly call to talk to you, maybe you can come visit him while his still locked up, maybe you’ll be willing to have him when his out, maybe you can move in together, maybe he’ll marry you, maybe he’ll finally get to fuck that sweet little pussy that his been fantasising about, maybe…maybe…..maybe..Ahhhhh!!!

Stealing sponges and a rubber glove when his on cleaning duty :((((

Bargaining with his prison mates for hair ties and an empty Pringles can so he can make his own makeshift fleshlight :(((

Fucking his fat dick with it while his eyes focus on your arse, imagining his got you in doggy and fucking you stupid:((( Maybe even putting his pillow in front of him and pretending its your arse, squeezing and spanking it >:(((

His corruption kink is feral…he knows his a lowlife with nothing good ahead of him, his more then aware that for the rest of his life his going to be labeled as a murderer, but the idea of him taking a pretty little thing like you and pulling you down with him makes him cum so hard his thick juicy thighs shake, fleshlight filling up with his cum and quite moans falling from his mouth >: (((

He doesn’t know were it came from, he just wants you to be with him and he knows he’ll never be able to live the white collar lifestyle you so obviously enjoy.

The idea of taking you out of that world and reeling you into his consumes him. Shitty one bedroom apartment, cardboard boxes as bed side tables, stained carpet and a flickering kitchen lightbulb. Its almost feeds his cocky superiority complex. Being able to pull a beautiful doll like you, get you so obsessed and needy for him that you’d follow him to the shit hole he calls home.

Being so obedient, so willing, that you give up everything you’ve worked for just to submit to him…..

Receiving that sweet little letter excites the fuck out of him, don’t get me wrong, but it also scares him a little, his protective instincts kick in a bit.

If you’re one thing, its a little naive.

You’re so willing to give up sensitive information about yourself without a second thought, you’re very obviously extremely vulnerable and trusting….

As much as he wants to protect you, he also sees these personality traits to be extremely beneficial to him.

You’re very easy to reel in after the line is crossed from polite and friendly to more flirtatious and maybe even a little bit sexual.

He addresses you differently in his letters now, no longer just using your name and actively being more outwardly affectionate towards you

“Hello my sweet girl :)”

and

“been on my mind lot’ lately, been thinkin’ about you, thinkin’ all sorts of things I know I shouldn’t ;)”

Once that barriers broken and your letters are just as enthusiastic, he knows his got you.

His got you to a point that he knows asking for a phone call isn’t a risky move anymore :3

He plans it though, he knows exactly what his going to do on that phone call and he knows nobody can be around while his doing it.

Like I mentioned in the first fic, his sentence was reduced because of his good behaviour, this obviously means his on good terms with the guards and most of the other inmates. They all owe him a favour in one way or another. He hadn’t asked for his good deeds to be returned, not needing them to be……until now.

He writes to you deciding on a date and time, Thursday at 3am.

He wanted to be alone when he talked to you, have some privacy and not be bothered.

His on really good terms with the night guard who works Thursdays, with just a little bit of bribing, he could be let out and have his phone call with you alone.

“Listen mate, ya’ want to know who’s movin’ drugs in and out of this joint? I can tell ya’ with no worries, but I need ya’ to do me a solid favour”

The guard his reluctant of course, but like I mentioned, Simon can be calculated when he wants to be

“Magin’ the raise you’d get if ya’ could give ya’ bosses that information? I saw ya had a photo of a little girl on ya car keys, think bout all the toys n’ shit you could buy er’ with some extra cash”

And obviously, he got what he wanted, it was light work really ;)

As 3am slowly got closer, you were shitting yourself, lets be real. It was hard to wrap your head around Si being an actual person, you know? Like of course his real, but it was all becoming a reality now….

You were three large glasses of wine in when it was time to call.

When your phone started to ring from an unknown number, you swore your heart dropped :((

The call almost rang out before you got the courage to answer it :(

When you did a very deep, rough voice with a heavy Manchester accent answered, you could hear the smirk through the phone, a confident “hello sweetheart” to match :(

His voice had your breath catch for a minute….of course you’d come up with your own idea of what he would sound like, but never in a million years did you think he would sound so charming, so confident, filled with anticipation, like he had been waiting for this moment for weeks…like he had thought of you the same way you thought about him :(((

It made your tummy swirl, that all too familiar hot ache feeling buzz in your clit :3333

On the other end of the line Si gently stroked his throbbing cock as you said your hellos :((

Your voice was even more memorising then he imagined, sweet little nervous giggles as you spoke to him, quietly letting him know that you weren’t quite sure what to say, that you were a little on edge, maybe a little excited.

You could hear his laboured breath through the phone, a distant wet sound that you couldn’t describe, so quite that you didn’t know if it was real or just your preverted mind playing tricks on you, making you hear things that aren’t really there :(

Just the sound of your voice was driving Si crazy :( you’re just as sweet as he imagined you, maybe even sweeter

He knew it was wrong of him :(

He knew that asking you to join his little game was evil. He had you right were he wanted you, and asking you to play with your pussy for him on the other end of the phone while directing you on how to finger yourself as he fucks his girthy cock with his hand wasn’t what you deserved…..

But he couldn’t help himself, not when you were talking to him like that, so innocent and sweet :(((

“Sweetheart, I need ya’ to do me a favour darlin’, okay? His cock was so hard it hurt, voice out of breath and sweat dripping down his brow. You were within arms reach, so close but yet so far away.

“Slide ya’ hand into your panties baby, start playin’ with yourself, come on, tell me what you're doin, describe it to me”

You so easily obliged, so willing to please him :( agreeing nervously with a stutter and shaky breath as you tell him what your doing

Describing to him what you’re wearing, an oversized t-shirt with nothing underneath :( telling him you didn’t put panties on just for him :(

You let out a quite moan as you play with your tits, telling him how hard your nipples are, squeezing the pebbles and whining as he eggs you on

“That’s it baby, play with those tits for me, yeah?, that’s my girl, squeeze em’ for me, there ya’ go” Si had to lean himself against the phone box as his tip leaked with pre cum :((((

Using it to lubricate his vainy cock making the wet sounds louder through the phone, you whine louder at the thought of his cock, closing your eyes you trail your hand down to your panties and slowly slip underneath the fabric to play with your wet cunt, just like Si asked:(((

“Rub ya’ clit for me baby, tell me how good I make you feel, say ma’ name, say it” he wanted so badly to commit it to memory, lock it away for later >:(

You moan his name as you circle your clit, eyes shut as you imagine Si doing it for you instead. You chant his name while your back arches a little, pleasure building at the sound of his rough grunts and wet cock being pumped through the phone >:((((

“I know, I know sweetheart’ just hold on a little longer for me, yeah? That’s ma’ good girl, ya’ not cumin’ yet” his hand fisted his cock, squeezing himself as tight as possible and screwing his eyes shut trying to imagine he was fucking your wet pussy, not his callused hand rough and dirty from the weights he was lifting early that day :(

“Finger ya’ cunt baby, finger ya’ cunt and scream ma’ name”

You were dangerously close to the edge, the knot in your tummy tightening by the second, your once nervous moans now turned unashamed.

Taking your other hand and slipping it into your pussy, you let out a desperate whine, muling your hips as you pumped yourself, squelching noises matching Si’s as you abused your wet pussy :((((

“That’s ma’ perfect girl, that’s it. Come on, let go for me, let me hear those gorgeous moans”

Finally letting the coil snap your back arched like a cat, legs shaking as you moan his name, desperate whimpers as tears of pleasure roll down your cheeks

Si gritted his teeth as he pumped himself, ropes of his sperm painting the concrete wall in front of him as his heavy cock twitched in his hands, animalistic grunts falling from his lips as that feral pleasure he’d been chasing washed over him. :((

He’d never cum that hard in his life, vision blurry from the white hot pleasure with your heavy breaths in the background :3

Just as he was about to open his mouth, speak to you again, the phone cut out, he had used up all his time with you :(

Harsh beeps filling his ear as his cock slowly softened, tip bright red from the attention…

He needed you more then ever now, protective instinct going through the roof :(

Knowing you’re out there all alone with nobody to keep you safe made his blood boil…..

He needed to have a set of eyes on you, the constant letters weren’t enough anymore :((((

Maybe there was a bit of jealously as well, the thought that there may be someone else….

It drove him up the wall, made him feel rage he had only felt very few times in his life

If he couldn’t have his eyes on you, then he’d 100% send Johnny out to do the work for him.

Looking through your letters and highlighting when you mentioned the name of the cafe you went to every morning, the name of the bar you and your co-workers went to every Friday to celebrate the end of the week.

Of course he wouldn’t tell Johnny the truth, simply asking him to keep an eye on an “old friend that’s going through a rough time” while his locked up for the rest of his sentence :(

And Johnny obliged, happy that Simon was in contact with people that weren’t just 141.

Reporting back to him every week, always with a positive review :)

A soft thing like you cant be left to fend for yourself sweetheart, not in a world like this. But don’t worry, his got your back, even behind bars ;)

RAHHHHHHHH, him, my mind is filled with HIM

PrisonPenPal!Simon is open for requests so feel free to send them throughhhhh, add to the AU, ask me expand on certain topics, whatever floats your boat >:)

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