#simon pearson x male reader

[miguel-owhora]

Simon Pearson, the man that you are. After cooking for the gang for so long, for so many years, going unappreciated, imagine pulling him away and offering to eat him out as a token of appreciation. He'd be quick to refuse but takes back his offer when you pull his pants down, pussy revealing itself.

He's a big, pot bellied man. There's no doubt in my mind that Simon has a big fat pussy. You'll have to use your fingers and spread them to get to the fat cock hiding under his mound, maybe even lift his belly up a bit to be able to properly slip his cock into your mouth.

[keppa-nero]

RDR2 x Male! OC/Reader

Robbing Stagecoaches And Killing

Lawmen

🎅Have faith it gets better!!🎅

CHAPTER 1 - Colter

TW: Bad Language \ Death \ Violence \ Mentions of mental illnesses \ Blood (?) \ Animal deaths (not cruelty) \ Posible slurs

The way from our past hiding spot to what we hoped was going to be a successful ride, had ended up being longer than we expected.

Colter was the name of land we entered, an extremely cold weather zone with heavy snow and thick layers of ice even in spring.

–Abigail says she's dying, Dutch. – I heard Reverend say as he walked near our wagon, making me wake up from my tired daze. I sat up with a groan and disconnected from their conversation, taking in the trail up ahead us this time. We got caught into a heavy blizzard it seemed, my eyes getting dry enough to itch in the two seconds I have been conscious, but I could still see the rest of our gang's coaches marching behind ours.

Sitting correctly, I tried to accommodate myself between the gang's properties pressing on my back, since I myself had chosen to travel in the transport wagon, out of all. But seeing how many horses and people were traveling all together, honestly made anyone feel we'd get caught any second now by the law, even if it was difficult with this god damned weather.

–Keita! Tighten up the ropes back there, the mountain's headed down! – Hosea's voice called from the reins, my eyes darting to see we were getting into hard terrain. Still no signs of this weather calming down.

I nodded and hopped inside the wagon, securing everything from below, and shivered a bit at the difference in temperature inside here. How I missed being in the hot wild west.

When I came back out though, Arthur had finally appeared after separating from us to search for a good spot, ended up we had luck and found somewhere nice and warm to properly rest in.

"Thank goodness" I swear I could hear all of the women say in unison from the other coaches.

I let my boots fall to touch the cold ice covered ground, moving quick to not bother the path and grabbed onto the metal hold of the back of the wood to step in the other wagon behind me, sitting down with a heavy sigh next to the ladies. Tilly, Karen Mary-Beth and Molly. Anyone would realize how violently most shivered, holding themselves to not freeze on the spot.

"Y'all doing fine, girls?" I asked softly, knowing these circumstances were being hard to handle, and more with the pressure of knowing the law was behind our feet. I noticed Molly jumped a bit at my voice, smacking my arm on instance, she probably fell asleep on the way and didn't expect me here. Like anyone ever, like I'm always unwanted.

–I thought you didn't like sharing a place, Mr. Sepúlveda. – Tilly spoke from below her scarf, as I just nodded my head slightly, leaning my head back on the wooden wall of our transport.

"Yah... I don't, no, just figured out you ladies could do some chatting, honestly thought some of you froze or something from how quiet you were" I said lightheartedly, hearing Karen scoffing.

–Because we were in peace, until you came, mister. – Karen remarked yet with a smirk, making my smile fall off subtly but I chuckled anyway and nodded, keeping the small conversation going.

By the time we got to where Arthur has directed us to, everyone was too tired and cold to complain about space. We went direct to grab any space to stay warm and try to make of this place a proper camp.

It happened to be a long gone abandoned line of family cabins, as we supposed, where we now had a large cabin and three other sheds, even a stable too, something that brought at least a hint of joy knowing the horses could rest too.

We eventually all joined inside the bigger cabin, quickly bringing Davey in too and check if he still had a pulse.

–Davey's dead. – Abigail spoke directly after noticing he didn't respond to anything, his breathing was gone and his eyes were half open staring at nothing, making everyone near the sight squint their eyes in silence. I leaned against the doorframe, keeping the quiet all of us shared while Dutch went into a little speech to give us hope, finally sending all of us to do something to help, eventually.

I didn't get any order but knew what to do, since we needed to be quick and not have more losses now that we had a spot. I went to grab some wood, for the heaters and to help Pearson with the food.

I didn't walk much away from everyone else, just turning the mountain we had near and stopping by the river, where some strong looking pine trees stood untouched, up to me.

I still tried to keep facing towards the way I came from, though it was impossible for me to get lost as I was two steps away from everyone, I didn't care. I like being alone, but I do not like to go alone, they were two different things and for my brain the latter sounded like I was gonna die. It's what I constantly had on my mind.

My eyes fixed on the dark brown bark of the pine tree, taking the axe I had by my belt, tightening my hands around the handle and starting to swing. The sharp thick blade cut easily through bark, making the first hits easy until it went through wood, swinging back and forth, with every impact my arms vibrating along the weapon, my breath hitching everytime it happened.

Still, I didn't look anywhere else than what I was doing, as shadows kept appearing on the end of my eye and disappearing when I looked that way. It really felt like someone, or something, was right there, standing next to me and breathing on my neck.

I could swear I felt sweat starting to form on my palms and dripping down my neck even when there was probably negative degrees where I stood, my throat working by itself and swallowing where there wasn't even saliva, making it feel like I was being possessed. My mind was against me, and my physical body now too?

"Fuck-…" I swore under my breath when I jumped at a sudden noise, whipping my head around in panic just to see it was a pinecone that fell, next to the pile of snow that formed after I kept chopping down the tree. My eyes then narrowed as something really stung in my arm, letting my axe fall as I rolled up my sleeve, seeing a really long deep cut I made myself when I got spooked. I groaned, now my clothes were ragged too.

I squeezed my arm to let the stubborn blood fall down freely to the snow and staining it red, the same color my arm was now too. The pain now really shot up and I cursed myself yet again for being so incredibly fucking stupid I couldn't believe myself.

Realizing then that it'd be no help to complain, I rolled my sleeve back down and got back to swinging at the tree, feeling the blood soaking my dark grey coat with every movement.

"Tree!" I then yelled at, well, no one, when the wood started cracking and leaning forward, as I stepped out of the way to not get crushed to death, then left a sigh knowing I had to break it down into smaller pieces now.

While doing so, I swear I could hear a distant shooting and yelling on the either side of the mountain, but I tried to shrug it off as my imagination, it usually was just that. It took me a long good hour to finish cutting the trunk fully, putting it all in a spread cloth and hanging it over my shoulder to drag it back to camp. I left it by Pearson's place where he was stirring the usual stew, grabbing a plate for myself and humming him off when he thanked me for the spare fire wood.

I, for once, decided to eat it all right there instead of alone, since I felt way too... Watched, to go on my own for now. After checking my arm, realizing no way in hell we were prepared enough to stitch this up, I sucked it up once more and went to my supposedly assigned shed I've been told was mine, not with anyone, since I repeat; I just can't be with anyone and no one wants to be with me, I'm too paranoid for anyone to want me near.

Well this was wrong.

I opened the door quietly with my arm, looking inside and seeing my bedroll on the left side with my bag, a heater in the middle and a- A lady, sitting on the bed that was supposed to be mine. Of course I froze in my spot and just stared at her with widen eyes. I didn't recognize her at all, and she was looking at me with red puffy eyes and a hurt demeanor.

So as logically as any, my body reacted before me and slammed the door closed, rushing off to the large cabin and almost breaking the old door down in the process, attracting everyone's gaze towards me, looking confused, and then noticing my expression and went back to their thing. This was way too usual and it was getting tiring, I know.

–What's got you all nervous this time? – I heard Abigail suddenly say, being the only one to approach me in this state. Having a normal conversation now grounded me slightly.

"There was a-... Lady, in my room" I said quietly, now saying it out loud made it sound actually ridiculous without context. I looked up at her when she just snorted in laughter.

–Oh yeah, there is, she didn't bother you did she? Her name was, err, Sadie if I remember. – She spoke in her relaxed manner, making me ease up instantly, realizing it wasn't something only I 'saw'. She seemed to notice my confused look after she said so, and just waved her hand off dismissively. –Right, she's a widow that Dutch and the boys took in, she lost her husband to some O'Driscolls and her house burnt down. She got the luck of a worm, you surely wouldn't mind having her share a room with you, wouldn't ya Keita?-

I just let a little 'Oh', realizing just how wrong I got the situation. I nodded absent-mindedly and glanced around, seeing the women, Jack and Reverend resting inside, warming up by the heater.

"Speaking about them, where's Arthur?" I asked, it was very noticeable when Arthur wasn't around.

–Arthur, he went with Javier to look for John, hope he's okay, that damn idiot. – She said in an almost angered manner, probably gotten pissed over the simple thought of John, understandable really. I laughed a simple 'Heh' in a dissappointed manner, knowing I'd have to socialize first with someone that was now sleeping next to me.

My feet brought me into my now shared shed, closing the door behind me as I sat on my bedroll on the floor, putting my bag next to it and taking off my boots, just sitting there with my elbows on my knees, my gaze down. The whole thing was silent and painfully awkard, the only sound being the creaking of the wooden planks with each uncomfortable movement I made.

"Hey" I greeted first in what I tried to make a calm tone, realizing she wouldn't talk first. "They didn't tell me I was having a roommate... Not that I mind I mean, what was your name again?"

–Sadie... Sadie Adler. – She croaked out after some seconds of reading me fully, looking away, making me do so too noticing I was staring, in not a romantic or charming manner.

"Well I'm Keita... I won't get in any of your business if you don't want me to, you can ask me anything you need if you want, no problem with me..." Like I wasn't the one being all worked up over a simple 'Hello', this was my shed, damn.

She simply answered with a nod and a slight sniff, turning on the bed to most surely go to sleep, signaling no more interaction. I decided to do the same, laying on my back and covering myself with the thin cover, taking off my gloves and putting them with my other things for tomorrow, noticing they were slightly blood stained too. I just stared at the ceiling, my eyes feeling heavy and a sigh left my lips, finally dozing off.

...

"...- Shit- Ah! Ah! Fuck! Ah!" I woke up by some yelling, sitting up quickly with my breathing now heavy and my eyes looking around in panic, sweating cold.

"God... I hate my life..." I mumbled and fell back on my bedroll, passing a hand through my stubble. Great way to do first thing in the morning.

Well, I guess the lady I was sharing a room with also heard me or I've been like this for a while, from the blank spot on the bed.

Fuck... I need a cigarette.

END CHAPTER 1

AN: Y'ALL I FINALLY FINISHED 👹👹. Those weird things and all are all based on my own experiences so please don't drop comments saying it's not like reality at all. The following parts of this fanfic I'll try to make them more interesting, I just couldn't do much in Colter. Don't lose hope in me‼️

[issdisgrace]

LOST BETS AND SKIRTS

In order to get money for the camp. The men and woman in the gang made a bet against each other that whatever group could con/rob the most out of people by the end of the week would pick what they did with the money raised but they also got to pick the punishment for the other group’s failure to collect.

The bet was won by the women and they decided that the men all had to wear skirts for the next week and that all of them had to go out of camp at least 5 separate times with the skirts on and they couldn’t just sit around camp and wait for the week to be over.

So all the men had to go into town to buy a skirt to wear for their punishment, using their own money. In the end Dutch ended paying for everyone as he was feeling very generous. But anyway, picture a group of men going into a boutique looking at skirts and trying them on. It was a sight to see.

Also, the women managed to get them all together at the end of the week and took a picture of all of them together in their skirt. Ms Grimshaw later on got a frame for the picture and she often walks by it and laughs, thinking back to that week.

WHAT TYPE OF SKIRT THEY GOT

Arthur let Charles pick out his skirt, as he was too overwhelmed by all the choices. Charles ended up pick out a light brown skirt for him. It was simple and Arthur can easily move around in it.

Bill got a simple dark brown skirt that flowed way too much in the wind and he may or may have not accidentally flashed some people because I fell like the man hates wearing underwear.

Charles got a purple skirt with a nice lace detailing on it. He looks magnificent in it. He looked like a god, even. Arthur spent almost his whole week drooling over Charles.

Dutch being Dutch got a really nice expensive black skirt with a nice red jeweled pattern. He also got the skirt tailored to him because he is Dutch.

Hosea got a blue skirt that reminded him of something Bessie would have worn. It made him feel powerful, and he rocked that shit.

John and Javier got matching black skirts. They both rocked them and in the end, the two started to wear skirts around camp 24/7 unless they were some place cold.

Kerian got a simple blue skirt that matches his shirt. Initially, Kerian was very self-conscious about the way he looked in his skirt, but over the week, he slowly became more and more confident.

Lenny manage to find an orange skirt that looked similar to his orange handkerchief. He mostly liked the experience, but he hated the attention that just wearing a skirt caused.

Micah got a red skirt because he loves the color red. He decided to fuck it if I’m gonna make a fool out of myself. At least I look good. So he fully committed to his art and got the whole womanly shebang and for his week he dressed up as a woman and robbed way too many men blind.

Pearson picked out a simple black skirt. He spent most of his week in the saloon with the others. He enjoyed the skirt, and it reminded of his time in the navy. So when he got drunk, he spent his time telling stories of his time in the navy.

Sean got a green skirt that matched his hat perfectly. He also got it because it has ruffles at the bottom of it. Sean flashed multiple camp members on purpose as a joke.

Swanson was surprisingly fine with the whole ordeal. He got a black skirt and rocked that shit. Now he only really wears pants when it’s cold and those are under the skirt.

THEIR FEELINGS ON THE PUNISHMENT

9/10. Arthur thought he would absolutely hate the whole experience, but he enjoyed it. He also thought it was funny that he was a man in a skirt chasing down his bounty. As no one really thinks that they would ever be chased down, tackled, and hog-tied by a man wearing a skirt. Also during this time his wallet kept fluctuating as he kept buying Charles fancy drinks then would go and caught a bounty to get back the money he spent on Charles.

8/10. Bill was surprisingly fine with having to wear the skirt. He actually enjoyed it, but he would never tell anyone. But sometimes when he’s a little too much to drink, he slips it on and struts around the camp in it. But during his week he went out more than the 5 required times and he surprisingly enjoyed everyone’s eyes being on him. Also, the first time he wore it to the saloon in Valentine, some drunk made fun of him and he beat the absolute shit out of him. So when he continued to show up throughout the week with the skirt on, no one dared to say anything to him.

10/10. Charles liked the whole experience. On the occasion he does wear the skirt as it is the perfect thing to wear when the weather is warm. Charles didn’t mind the attention he got while wearing the skirt, as it was mostly people completing him or buying him drinks.

7/10. Dutch thought he would hate it but ended up really like the whole experience. He kept the skirt and wore it on occasion around camp when it was hot as hell out as it had a nice breeze and he didn’t feel so hot and stuff down there. Dutch also had the thought when he was wearing the skirt and people would look at him funny that at least he’s wearing something and not going around butt ass naked.

7/10. Hosea enjoyed the experience and took it as a good lesson on women’s beauty standers. It had a downside, and he wasn’t able to con as many people as he would have liked due to the skirt, but he still managed to get a good bag in the end. At the end of the week, he took it to Bessie’s grave as a gift.

10/10. Javier really enjoyed it. He enjoyed the attention that came along with the skirt as well. He picked up many ladies and men in the saloon due to his skirt and his charm. Like I stated, he is only ever found in a skirt when he’s at camp. He finds it nice and comfy. He also likes how he is defying societal norms.

8/10. John enjoyed it. The whole experience brought something out in him. He started to care more about his appearance and his clothes. The experience also brought out a more feminine side in John, but if anyone dared questioned or asked him about it, he would threaten them with his knife. His thoughts were definitely along the line of if you say the wrong thing about me and my knew found femininity, I will cut your balls off and shove them down your throat.

6.5/10. Like I said, Kerian was initially very self-conscious about the way he looked in the skirt, afraid that one of the others would make fun of him despite being in the same boat. As the week went on, he slowly found confidence not a lot, but some was better than none. Due to this whole experience, Kerian started to feel more comfortable with himself and the way he presented himself. He started presenting more androgynous. Eventually, overtime he wanted to explore his feminine side beside wearing skirts around camp. So he managed to work up the courage to ask the girls how to do makeup. They were all happy to give him tips and tricks. In the end, Kerian never thought a stupid bet would make him more comfortable with himself.

7/10. Lenny is very chill and enjoyed his time in the skirt. Like I said earlier, Lenny didn’t really like the attention when he wore his skirt out for the designated 5 times. The only times he was fine with the attention was when a surprising amount of women kept buying him drinks. After the week was up, he cut the skirt up into different sizes and uses them as rags.

10/10. Micah has commitment to his craft. He shaved his facial hair off; he got one of the girls to do his makeup. He made up a fake back story and perfected his voice, which he surprisingly sounded like a woman. Some of the guys thought the girls brought another woman back to camp, only to find that it was Micah. The whole camp, even Swanson and Pearson, went to see Micah put his plan in action. They watched from a far as Micah played damsel in distress and robbed man after man. He ended up with a bag full of goods. He also kept the git up and on occasion when he’s in a good mood he’ll put it on and play damsel in distress.

8/10. Pearson enjoyed the whole experience but he won’t tell anyone that. While Pearson was out, he blended in well and never got any comments on the skirt. Also, like I said earlier, when he got drunk, he told stories of his time in the Navy. Let’s just say the gang found out how much of a freak Pearson was when he was younger. 0/10 the gang will never let him get drunk enough for story teller Pearson to come out.

9/10. Sean loved it. He still wears his skirt around camp. He doesn’t give two fucks what others have to say about him and his skirt. He went out his required 5 times, but other than that, he mostly lounged around camp. When he was out, he found that he was mostly ignored. Most people thought it was a cultural thing, so they didn’t say anything.

10/10. Swanson throughly enjoyed it but he was also drunk half the time, so that also probably added to his willingness. He spent more than his 5 required times out of camp. He never got questioned on why he was wearing a skirt as people just thought it was a religious garment. Also, like I said earlier, Swanson now only wears a skirt, but when it’s cold, he wears pants underneath his skirt.

EXTRA

Jack got jealous after 2 days that everyone was wearing a skirt, so he convinced Abigail to take him to go get one. He got a black one to match John’s.

10/10. Jack loved it and he, like his father, wears the skirt around camp all the time. I feel like he also continued this into his adulthood as a way to honor his father. But during the week, Jack went out with John a couple of times to show off that he was matching with his daddy. While Jack was out with John, he saw his father threaten and beat the shit out of a couple of people that made comments about the two of them. John then made Jack promise to never tell Abigail and Jack stuck to his promise and never told his mother.

Trelawny was just visiting for a week and the week he came was the week the punishment happened. Trelawny decided eh why not, even though I’m not a part of this I will participate. He went in to town with the others ended up getting a really nice red skirt with black lace detail on it.

10/10. Trelawny loved the whole experience. He also very much enjoyed the attention that he got when he was out. He also enjoyed how many men and women bought him drinks throughout the week, but as pay back he would do magic for them. I must warn you, when he gets too drunk his magic starts lacking, and he starts speaking French. So if you don’t speak French, I’m afraid that you’ll be very lost when he starts ranting.

[redeadepression]

FAQ | Request Rules

What kind of Requests do you do?

I take headcanon requests. You can check my bio to see if Requests are opened or closed. I sometimes open Fic Requests but unless I add them in to my Bio they are closed. Headcanons are much quicker and much more likely to be filled.

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I take requests for nearly all rdr2 characters. The characters I don’t write for are listed in my Don’ts. John Marston and Arthur Morgan are my muses. I am much more likely to fill requests for them. 

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No. I do requests that interest or excite me. I try to do all the requests I am sent but I absolutely don’t guarantee a fill for every one.

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I try to post a new set of Headcanons every 2-3 days depending on RL responsibilities. Public Holidays and Family commitments etc.

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YES. Yes you can. Please feel free to use my inbox as a dumping ground for all your headcanons safe and not safe for work. Sometimes I will respond with headcanons of my own.

How do you tag your filled requests?

I tag my filled requests with the characters names. I also tag them as “headcanons”, “HCs” and if applicable I use the tag “nsft”. I also abide by the citrus scale. 

Important Request Rule

PLEASE Specify the gender of your reader requests. Male, Female, Gender Neutral. If I do not have a specified gender I will revert to FEMALE READER  for NSFT Requests as I myself am female and find it easier to write.

I will try to keep it gender neutral for SFW requests.

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Mental-Illness and related topics

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Leopold Strauss

Reverend Swanson

Simon Pearson

Uncle

pedophilia / underage characters

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[miguel-owhora]

meow meow meow Thinking about fucking Pearson on the backside of a wagon. Having him bent over on the bedroll you placed down, pawing at his belly and rolls, rocking your hips into him at a slow n steady pace. His pussy would be so wet and sloppy, coating your cock and his thighs in a shimmery slick. meow meow meow