#prisonpenpals | Explore Tumblr Posts and Blogs

kittykattropicanna · 4 months

Note

would you please be able to go into more detail about your prison penpal!simon? why is reader doing it, how did they choose simon (if they had a choice at all), the sorts of letters they exchange? and if they’re any sort of smutty bits for them too? your mechanic au has me absolutely feral beyond words so seeing this made me so excited.

Omg you’re my first asked AHHHHHH I want to scream thank you so much!!!!!

Absolutely I can go into detail about PrisonPenPal!Simon :3 I can't get out of my mind how deprived he is argh!!! >:( all this time alone, and now that you're here writing him pretty little letters, he can't imagine life without you :3

TW: mentions of murder, jail, corruption kink, breading kink, masterbation (Reader & Simon), public masterbation (kinda), smut, not sub!simon but he does cum in his pants, ahhh you're both just so obsessed with each other :3

PrisonPenPal!Simon masterlist

Regular masterlist

I’ll give you a little back story to why Si actually ended up in jail…

I feel like he retied, left SAS and tried to integrate back into civilian life but failed miserably. He started going out to bars and drinking pretty heavily. The alcohol made him angry, he never was outwardly violent, but everyone could tell he was just a very dark, tortured guy that sat in the back of the bar every night and drank himself stupid. It was like an unwritten rule that nobody bothered him. His a massive guy who’s ex military, if you had half a brain you would leave him alone.

One night he was leaving the pub and this stupid, stupid 18 year old kid thought it would be funny to try square up to him and impress his friends.

It didn’t matter how many times they told him to quit it and leave Simon alone, he still trudged up to him with his head held high and chest puffed.

This kid came up behind Si and punched him in that back of the head. It wasn’t a good punch by any means but it was more then enough to drive Simons drunk brain into utter rage.

He turned around and punched this kid straight in the head. He went down like a stack of bricks, head making direct impact with the concrete floor, killing him instantly.

The kid was only 18, he had so much life left to live…..

Of course Si felt absolutely disgusted in himself, he couldn’t believe what he had done. Killed a poor kid who made a stupid decision and ultimately ended his life as well.

He handed himself over the the police without hesitation. He went quietly and respectfully, cooperated with the police throughout the whole trial, never redirecting blame onto the kid or made it harder then it needed to be.

He pled guilty for involuntary manslaughter and assault. Gaz, Johnny and Price all pitched in to get him the best defence lawyer humanly possible……ultimately, it worked. Even though the general public was outraged at his light sentence.

Simons lawyer claimed the punch was in self defence. Someone attacking him from behind also trigged his PTSD resulting in Simon not being able to control his actions in that moment.

These defences along with him serving in the military for 15+ years and cooperating with the authorities got him 8 years in prison, his sentence was quickly reduced to 4 because of his good behaviour.

It wasn’t an ideal situation by any means, but it was the best case scenario with the cards he was dealt.

But lets fast forward to the present….. How did you decide to actually start writing to an inmate? How did you even find out about it?

I have this really cute idea that maybe you were walking through the shopping centre and there was one of those pop up markets that sit in the middle of everything, you know, with the really annoying people that flag you down and you have to awkwardly not make eye contact and walk past them while they’re try and sell you stuff?

Yeah, one of them. This specific stand kinda caught your eye though, It was called “Write An Inmate”

You talked to the guy at the stand about what exactly “Write An Inmate” was and he explained that he was part of the program when he was locked up, how much it helps inmates get through their sentence, helps connect them to the outside world and genuinely just keeps them hopeful.

First off you were a little hesitant…..speaking to someone who’s in jail because they broke the law sounded a little scary….

But hell, its a start of a new year and taking some time out of your day every once in a while to write a short letter to help keep someones hopes up is the least you can do.

Besides! One of your childhood best friends big brothers went to jail and he wasn’t a bad guy! One of your new years resolutions was to spread more kindness and this is just a perfect way to do so!

Once you got home, you look up the website on the brochure that was given to you and quickly start scrolling through inmates.

They all had profiles with information about them. You couldn’t see what they were in for, but you could see other information like their name, age, date they signed up for the program, time served/time until they get out, amount of letters they have received, a short description of who they are/what they like and a few photos showcasing what they look like.

You scrolled through a few but they all seemed to have gotten hundreds of letters, you wanted to write someone who wasn’t getting flooded every week with letters, maybe send a letter to someone who could use a pick me up.

Clicking on the last page you scrolled to the very bottom and click on the last inmate before it even had time to load.

Once the page opened the name “Simon Riley” appeared on your screen

After looking through his profile a wave of sadness rolled over you

Name: Simon Riley, most people call me Ghost Age: 36 Joined: December 26th, 2021 Letters Received: 0 Time served: 3 and a half years Sentence ends: Year and a half Description: ex military. I like dogs, big ones not small ones, the outdoors, playing cards and motorcycles. The first thing I want to do when I get out is to eat a steak.

Attached was three photos. I won’t even lie, they’re definitely dad selfies from different angles HAHAHA they’re such grainy photos too, like they’ve been taken on a 10 year old android.

Two of the selfies are him with a black balaclava on and the last one was of his face without anything covering it, but again it so grainy you can’t really make his facial features out.

Simon had joined the program two years ago and hadn't received one letter. You felt horrible, he joined the day after Christmas probably hoping to receive something, anything, but not one person took the time to write him…..

So obviously Simon was going to be your prisoner pen pal, how could he not be…..

I think the letters start off pretty innocently tbh, you don’t start writing to Simon with the intention of starting any sort of sexual or romantic relationship, it truly is out of the goodness of you’re heart, you sweet girl :(

Simon had totally forgotten about the program honestly, imagine his shock when the prison guard threw him a letter.

When he frowned and asked who its from the guard just shrugged and said “write an inmate program” and walked off completely unfazed.

But again, starts out super innocent, things like “I saw that you like big dogs, what’s your favourite breed?” and “what’s your favourite card game? I know how to play blackjack but I’m not very good haha”

I’d like to think you don’t even disclose your gender or name at the start. Keeping everything under lock and key.

Simon also answers back with pure intentions at first, he has an inkling you may be a women because the hand writing is wayyy to pretty and delicate to come from a man.

But again! He doesn’t get his hopes up, it could be an old granny for all he knows, but he can’t shake the idea that maybeeeee it could be someone a little more his type, ya know ;)

After a couple weeks of writing letters back and forth you feel like you’re getting to know him a little better. He asks you to call him Simon, not Ghost and he starts writing the cheesiest dad jokes at the bottom of every letter.

“Two fish are in a tank, one turns to the other and asks “do you know how to drive this thing?” a little army humour for ya’ :)”

His so charming in such a rough and rugged sort of way you know? It sounds silly to say, I mean, you’ve never met him! But the way his handwriting is complete chicken scratch and how he adds little “:)” “:(“ and “>:)” makes you giggle!

You end up telling him your name and how old you are, I mean, its only fair! You know his name! You definitely didn’t tell him because you wanted to get his mind racing, get him thinking about all the different possibilities, make him fantasize…

Its fair to say you have a little crush on him :( ahhhh its so humiliating! A city girl like you, good job, successful family and a bright future laying in bed every night fucking your pussy with a brand new dildo you bought just so you could imagine Simon, a felon, fucking your little cunt :(

When Simon sent his letter that week asking for a photo of you, your little crush just got bigger :(

“Its only fair don’t ya’ think? You know what I look like, why don’t ya’ return the favour sweetpea ;)”

And of course you did!! He asked so politely!

Putting on your pushup bra, doing your makeup and styling your hair all for him:(((

You get so frustrated because you don’t want to look like you’re trying too hard for him, argh! Its all so embarrassing!! Your such a needy girl >:(

You make sure to push up your tits, your bra helping them spill out over your cute little shirt and giving him a good view of your gorgeous body.

After an hour of taking photos you finally get the shot you were looking for

Eyes sparkling, cute little smile on your lips, light hitting your face just right, lacy bra slightly peaking out the top of your shirt just enough that it looks like an accident, beautiful tits sitting right in frame so he can get a good look and the slight curve of your waist visible.

Its perfect, it look so effortless…..in your eyes at least

When Si received your letter, his cock got hard the second he saw your picture :((((

Since his been locked up he hasn’t been able to jerk off properly >:(

His balls are so heavy as is, and now he has a photo of you

He could basically cum in his pants at the thought of holding your waist as you ride him. Using his big callused hands to fuck your pretty pussy onto his aching cock >>:((((((

You’re so put together! nice clothes, from the look of the background, nice apartment, clean bedroom. Just the thought of him corrupting you, fucking his baby into you, making you move into a shitty little apartment while he works and you look after his chubby baby makes his dick start to twitch :3

Before he can stop himself, he cums all in his pants :(

He hasn’t cum properly in years! yet a simple photo of you did it for him in seconds!!! You’re such a nasty minx, you know exactly what you’re doing you dirty girl >>:(

That night he lays under the covers, his cell mate fast asleep on the other side of the room as he slowly pumps his cock to the photo of you.

Eyes closed and head thrown back against the thin pillow, he bites his lip so he doesn’t make any noise.

You see, playboy magazines get passed around all the time, they’re not hard to find if you know the right people, but it just doesn’t do it for Si!!

Of course they’re beautiful women, there’s no doubt about it, but everything so photoshopped :(

Si likes his women natural. No skin smoothing filters or enhancements from photoshop, he likes his women real

His so deprived that he cums in record time, his hot load shooting all over your face, the once clean photo now sticky and stained….

He wished he had it in him to be embarrassed, but he just can’t! God, he needs to hear your voice, your picture just isn’t enough anymore….

In his next letter he asks if he could use his monthly call to speak to you……Johnnys just gonna have to wait, they can talk football another time >:(

Aghhhh, PrisonPenPal!Simon is so fucking cocky it hurtssss, 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 >:)

!Disclaimer! - Above is NSFW content - MDNI - If you follow my blog without your age in your bio, you will be blocked - If you are under the age of 18, you are not welcome here, otherwise, enjoy :)

Cat divider sourced by @positively-mine from Pinterest - Pink line divider by @eloquentreverie - MDNI divider by @cafekitsune

Basic blog housekeeping - fic requests guidelines, boundaries and my rules for minors

574 notes · View notes

kittykattropicanna · 4 months

Note

it's 2 am and i should sleep but i just read your prison penpal!ghost now it's rotting my brain!!!! ><

reader would so try to send him gifts if they're allowed. special holidays aren't miserable for him anymore as he would be accompanied by reader's sweet little presents!!!

Sleeps for the weak baby, sleep when you’re dead ;)

Of course you're going to look after your man, he does so much for you, the least you can do is send him some money to treat himself!!! maybe a gift or two you dirty girl :3

I know I promised to upload this last night after work but I was sleepy. IM SORRY PLEASE FORGIVE ME

TW: edging, Si fucks himself with your dirty panties, smut, masterbation (Reader and Simon) its just fucking disgusting and dirty, but also kinda sweet <3

PrisonPenPal!Simon masterlist

Regular masterlist

Absolutely, holy shit. After your first phone call, you’re his, he makes that so unbelievably clear through his next letters. :)))

Telling you how much he craves you, how you’re the only thing on his mind, describing in intimate detail how his gonna touch you, kiss you, fuck you :((((

His so fucking desperate for you, to the point he actually gets enraged knowing he can’t touch you. Just the thought of you being on the other side of the wall makes his skin crawl, you’re right there, only thick cement dividing him from you :((

Its even worse knowing that he can’t do anything about it >:(

Si’s a problem solver, he prides himself on being able to weasel his way out of practically any situation without a problem, if that’s reducing his sentence down to basically nothing or getting away with his little late night phone calls with you. He always finds a way to make it work, but for the first time ever, he can’t fix this, his stuck here. No exceptions, no sweet talking to get what he wants, no amount of calculated manipulation could get him out of this situation, and it makes him go absolutely mad.

At this point he has a year left of his sentence, his so fucking close to being let back into society, so close to finally being with you :(((

Letting his emotions (and dick) cloud his judgment, driving him to think about making stupid decisions such as an attempted jail break would be absolutely the worst idea of his entire life.

Ohhhhh, but its so tempting :(

But it would just put more time between you and him, as much as he wanted you now, he knew it was only going to rip him away from you again in the long run :/

And that’s if his even successful, one night with you would mean the world to him, but it wasn't worth being thrown back in jail, only separating the two of you for longer :(

He just needed to sit tight, let the days roll on and try not to think about your soft moans through the shitty speaker of the prison phone. :(((

He absolutely asked you to be official after speaking to you for the first time. It drives him crazy knowing when guys try and hit on you at the bar, you smile brightly and tell them that you're his, his to keep.

One of the guards asked him what’s the first thing his going to do when he gets out, with a dopey smile he chuckles a little

“See ma’ missus mate” his so fucking cute, his actually so obsessed with you, so proud that you’re his ;))))

Of course the other inmates wouldn’t know, and technically he most definitely shouldn’t of told a guard, news spreads, but he couldn’t help it, it slipped out, and you know what, he was fucking proud of it :)))

You 100% would send him money and gifts, Si makes a little money, about £35 a week either cleaning, laundry duties, basic maintenance, basically anything the job program can offer him.

The only issue being when he first signed up, he made sure that all his money was payed into Price’s bank account. He didn’t want to risk using it, the whole reason he started the work program was because he wanted to try and set himself up once he got out, at least have some type of savings waiting for him on the other side. Every now and then he regrets it, but he knows its for the best :/

Learning that Si was so strict with his money that he didn’t treat himself to anything didn’t sit well with you….and its not like you’re struggling financially, you work a good job and your daddy is always willing to send money if you ever needed it!!!!

A hundred odd pounds a month isn’t going to leave any sort of dint in your bank account, so of course your going to send Si some money to treat himself!!! You’re such a sweet, sweet girl :(((, his sweet, sweet girl.

You start sending the maximum amount each month which comes out to about £150, its the least you can do!! His your boyfriend! he might be a felon, a little perverted and rough around the edges, but to you, his perfect :)))

His so grateful as well :(( treating himself to snacks :((( chocolate bars, skittles and gummy’s, buying himself a book or two, replacing his flat, stained pillow and ratted blankets, getting himself some actually nice soap and a new toothbrush, buying clothes that actually fit him!!

His muscles have grown so much since being locked up :3 there’s nothing else to do besides lift weights, work and sit around :((((

“Sweetheart, I want ya’ to know, the second I get out of here, imma treat you real nice, give ya’ everything I can, look after ya’, protect ya’”

and

“The minute I get ya’ home, its all about you, yeah? Imma lay ya’ down and eat ya’ like a starved man, overstimulate that little cunt till ya’ beggin’ me to stop, fuck ya’ so deep and hard that you’ll forget ya’ fuckin’ name, whatever ya’ want darlin’ its all yours, been lookin’ after me so well….. imma show ya’ how much I appreciate it, as ya’ can probably tell, i’m more a man of action, poetry an’t ma style baby ;)”

Definitely learns origami from other inmates, makes little paper swans and hearts for you, the paper always being a little stained from his dirty fingers, obvious crease marks showing his folded it the wrong way and had to reattempt :))))

God he knows how to treat a women :33333

But what I really want to get into are the gifts you send him…..;)

As I established in my last fics about you sending things to Si, you absolutely send him innocent gifts.

Photos, one of your favourite gold necklaces, an oversized tee that smells like your perfume…. Cute little personal things so he can have a piece of you, nothing crazy :3

I feel like you were reading a spicy romance book. It mentioned the main character stealing his lovers used panties out of her dirty laundry basket, very quickly and idea clicked in your brain :((((

You wanted it to be a surprise for him :(((( you didn’t mention it to him in your letters, only telling him your working on a little something that’s crafted just for him ;))

Waking up in the morning you make sure to fuck yourself with your fingers :((

Covering your panties with your juices, making sure their absolutely soaked in your cum :((

Rubbing your thighs together while you’re at work, soaking through your panties with your arousal :((( thinking about Si eating your pussy just like he promised while in important meetings, loosing focus…. your boss pulling you aside and asking if you’re okay :((

Scrambling to find an answer to explain your distracted behaviour and flushed cheeks >:(

He ends up sending you home because you’re distracting everyone with your aloofness :(( putting the rest of your team behind because you're a selfish girl with a dirty mind >:( can’t even focus in your workplace because Si’s dirty words have taken over every aspect of your thoughts >:(

At the end of the day your panties are ruined with your slick, soaked all the way through and smelling of your orgasm just like you planned ;))

And when Si received your thong obviously used??? :000000 he let out a low grunt....

Just the idea that you did this for him, fully confirming in his mind that you wanted him, craved him just as much as he craved you made something animalistic set off in his mind….

Because he received your package in the middle of the day, he couldn’t hide and tend to himself like normal >:((((((

He needed you now, he needed to fuck his cock NOW, not wait till his cell mates were asleep, his heavy balls ached and he knew if he didn’t relieve himself soon, his blue balls would become unbearable >:(((( aching and hurting with each step, uncomfortable and frustrated :(

Purposely being a dick and coursing havoc with his inmates so he can be locked up for his disruptive and disrespectful behaviour ;)))))

A shit eating grin when his in handcuffs being walked to his cell, knowing your panties are tucked into his boxers ;))))) his won yet again ;)

Like I’ve said before, and I’ll say it again, he ALWAYS gets what he wants :)))

The second his cell locks his ripping his hard, leaky cock out and wrapping your used panties around himself :((((

Pumping his fat dick, the friction of the fabric making it that much more satisfying :((((

Closing his eyes and imagining you walking around all day, turned on and flustered for him >:((((( the idea of you restricting yourself from fucking other men because you're his, knowing all you want is to be filled with dick, have the feeling of a real cock fucking you, not your cold, rubber dildo >:(

His precum mixing with your juices only turns him on more, knowing that this is the closest he’ll get to fucking your cunt for now :((

As his big hands slowly pump his dick, wanting to savour the moment, he lets out animalistic grunts, slowly speeding up and then slowing his pace, he edges himself almost whimpering when he refrains from his release yet again :(((

Something about holding back satisfies him, his training himself for you, getting ready for when he fucks you for the first time, wanting to hold out long enough that he can rip orgasm after orgasm out of you, forming a white rim of your cum around the base of his cock :(((

Grunted whispers of your name falling from his lips as he tries to hold back yet again, legs twitching and face getting hot as uncontrollable ropes of cum finally release from his vainy cock :(((

His never cum that much in his life, your panties damp with his semen, dick so sensitive that even the feeling of the fabric from his boxes makes him flinch >:(((

You’re such a good girl, always knowing how to please him, feels like you know him inside and out already ;)

You just wait until he gets his hands on you sweet girl ;)))

Y'all are so fucking obsessed with each other I CAN'T

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 >:)

!Disclaimer! - Above is NSFW content - MDNI - If you follow my blog without your age in your bio, you will be blocked - If you are under the age of 18, you are not welcome here, otherwise, enjoy :)

Cat divider sourced by @positively-mine from Pinterest - Pink line divider by @eloquentreverie - MDNI divider by @cafekitsune

Basic blog housekeeping - fic requests guidelines, boundaries and my rules for minors

413 notes · View notes