#prisonpenpal!simon

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

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

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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