Character Profile: Simon

Name: Simon son of Salman, Simon Silver (Modern AU)

Aliases/AKAs: N/A

Title(s): N/A

Hair Colour: Blonde

Eye Colour: Hazel

Height: 154 cm

Weight: 53.5 kg

Build: Sturdy, tall

Distinguishing Marks: Striking curly blonde hair, distinct lack of hair everywhere else

Dick Size: Average

Relationships (Romantic and/or Sexual): Ana (girlfriend), Trevor, Al, Hugh, Marcus, Daniel (fellow slaves, former), Ozzy (friend), Aldous and Raven (girlfriend’s hot dads), Theodore Silver (former owner)

Family Relationships: Serenity daughter of Scarlet and Salman son of Simon (parents), Susie daughter of Serenity (sister), Stanford son of Simon (uncle)

Sexuality: Bisexual

Preferred Positions: On top

Kinks: Body odour, feet, clothed sex

Orgies Attended: Regular Slave Orgies

Bio: The oldest child of an instrument maker and her husband in the small town of Caplin’s Breath outside of Merket, Simon’s parents fell on hard times over the last few years that got harder when their younger daughter became seriously ill. In order to pay for her medicine, Simon’s parents chose to sell him into slavery, promising him that they would borrow money from Simon’s uncle to buy him back within a few weeks at most. Simon doesn’t know if they were lying or if Theodore just wouldn’t let them do that after he was bought, but either way he ended up a replacement for a slave who betrayed Theodore—who later saved his life and became his best friend. After just over half a year in Theodore’s house, Simon has recently been freed unexpectedly, and though he still loves his friends, he’s moved out and is now living with his girlfriend Ana and her dads, who took him in without question. He currently waits tables at their restaurant and is thinking he might learn how to cook, and he’s kind of surprised by how quickly and easily he became a normal person after being freed, which he attributes mostly to Daniel making sure that his period of enslavement was as easy as it possibly could be.


  • Simon used to think that only people who deserved slavery got turned into slaves. It was several months after he was enslaved before he realized that was wrong
  • When Susie got sick, Simon started working wherever he could to earn money for his parents to help them pay for her medicine, and got more and more distressed because it never seemed to be enough money
  • Simon always knew running away from Theodore wouldn’t get him anywhere. But he tried to do it anyway, because he thought going nowhere was better than staying where he was
  • Simon hated Daniel for a while after he was nearly killed, feeling that it was Daniel’s fault his life had been in danger. It took him a few weeks to move past that to the fact that Daniel saved his life both times, and now he considers himself permanently indebted to Daniel
  • Simon finds most games too easy and likes to invent new ones. He’s still working on his best game yet and doesn’t know when it will be finished, but he knows it’s going to be called Dragons in the Dungeon
  • Even though enslavement was the worst thing that ever happened to Simon, he also thinks that meeting the other boys was the best thing that could have happened
  • Simon is too afraid to try to find his parents again. He doesn’t want to find out if they really did try to find him. He’s certain Susie died and doesn’t want that confirmed either
  • Upon being freed, Simon moved in with Ana and her dads, who immediately accepted him as part of their family
  • The first thing Simon did after being freed was cut all his hair off
  • Simon doesn’t know what he’s going to do with the money Theodore gave him yet. Aldous and Raven refused to let him pay to live with them and indeed are paying him to work at their restaurant, so for now he’s just kind of sitting on it until he decides what to do with it


  • “It’s not fair. It’s not. I’m not really a slave. I’m…I’m not really a slave.”
  • “I’m going to see her again. My parents are going to come back for me.”
  • “No. No, I’m not okay. I…I almost died! Twice, and both times it was because of you.”
  • “What can get behind your ears that’s so important to clean out? Who’s putting dirt in their ears?”
  • “Feel like we’d have accomplished a lot more in the world if we weren’t all so obsessed with sex all the time.”
  • “If I don’t know that then I don’t know anything, Daniel. Because I need it to be true even if it’s not.”
  • “Fuck that. Fuck Theodore. I’m going to do sex stuff in his bed with someone I like while he’s not here because fuck him.”
  • “Yeah, but you can’t have fun forever and the game can’t end if someone doesn’t win.”
  • “Hey! She’s not my girlfriend, oh my God,”
  • “I’m not cheating, I’m better than you.”
  • “You can’t get pregnant on the first try, right?”
  • “Come on, Daniel. If you want us to stop saying bad words, you have to tell us which words are bad.”
  • “I want to go. I don’t want to be here. I…I hate living here. I love you, Daniel, but I hate living here.”


  • Simon thinks that the stupidest part of their slave uniforms is that they’re just a little too long to show off the parts of his friends’ legs that he wants to see
  • Simon used to play dress up with Susie where he’d play the princess getting rescued from various monsters
  • A few months before he was sold, Simon played a dick-measuring game with some of his neighbours, which he lost. He sucked all their dicks after, per the rules
  • Simon really likes to eat duck, but thinks that Theodore’s fancy chefs cook it wrong
  • Simon regrets that Theodore regained interest in Daniel once the weather had started to cool down. He’d have liked to share a room with the other boys when it was hot
  • After Theodore raped Simon, he thought he’d never want sex again. He was surprised by how quickly he got over that once he was with the other boys
  • Simon once had a dream that Theodore was his father, which led to him accidentally calling Theodore ‘dad’ the next morning, which led to him being furiously embarrassed for two days
  • Simon once had a bath with Ana and her dads in their small bathtub, and he’s not entirely confident that it was being naked with Ana that gave him the boner
  • Simon was worried about moving too fast with Ana, but on their second date she convinced him that they’d known each other long enough for sex, and he agreed, which led to them swapping oral in a park. They had penetrative sex after their third date
  • After leaving Theodore’s house, Simon got lost on the way to Ana’s. He’d never gone there during the day

Modern AU: Modern Simon is one of many foster sons of Theodore Silver after getting stuck in the foster system due to a misunderstanding involving his parents spending time at the hospital with his sick sister. Simon spends little time at Theodore’s house these days, having found a good group of bratty friends to hang out with, and also found that his girlfriend’s dads are more than happy to let him live with them, even having offered to adopt him so he can move in. The paperwork is pending but in the meantime, Simon has recently started high school and spends most of his free time being horny with his foster brothers, role-playing with his friends, playing lengthy JRPGs instead of doing the work he’s supposed to do, kissing Ana and doing part-time modelling work without Theodore’s permission.

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