Valentine Adelaide



Valentine Adelaide
Black Widow
White, German
Hair Color
Eye Color
177 cm / 5'9.5 (he insists on stating the half inch)
February 15
Blood Type
With Aurelio, New York City area
Image song
Voice claim
Oshi mark

Valentine Adelaide

Valentine's bio has mildly NSFW and dark content.

Design notes page (for commissions, art, etc.)

Icon and profile image that make me shake like a chihuahua by c7moe

Valentine Adelaide (full name Valentine Vivien Adelaide) is a 26 year old Hitman for the Lammergeier Syndicate. He's a man who crossdresses, and identifies as male despite appearances. His attire of choice most often is a Victorian-era styled maid dress. As with the rest of the syndicate, he wears black leather gloves. His weapon of choice is a katana (named Julia) due to his lack of depth perception and a preference for blades. His syndicate alias is "Black Widow".

Personality wise, Valentine can be best described as unhinged and flirty, yet carefree. He doesn't care what people think of him, so he'll openly lay anything he's thinking of on the table and not stress over judgement. He often uses flirting as a weird way to communicate and doesn't always mean what he actually says. He's just trying to be friendly. People who are around him long enough know to just brush him off. Despite those oddities, he's a social butterfly and gets along with most everyone he talks to, so long as they don't judge him for who he is. Though true that he's a full-time crossdresser as a personal fashion choice and for comfort, he also uses it to feed his own perversions. Valentine especially likes the attention he gets from it... But only of the positive variety. He hates the feeling of wearing mens' clothing and pants, only wearing them when absolutely necessary for a hit. Besides them being tight and constricting to him, he remarks that it "doesn't feel like Valentine". He's been this way since he was a child, even if he couldn't actively dress how he wanted full-time until later.

He has a serious penchant for one of his bosses in particular, Aurelio. He calls him Boss, along with other nicknames. Valentine is often seen around him, clinging to his arm with a wide smile across his face. They both have a long history together, with Valentine initially being hired as his apprentice. He wishes a lot of romantic and sexual things with him, but is pushed away due to their work relationship and other factors. The two are together enough to have him be considered as Aurelio's bodyguard, especially on occasions where he needs his protection. As much as he's rejected, he says Aurelio is the only man he'll ever truly love. But he's just happy to be with him regardless as his best friend and apprentice, as much as it frustrates him. Even just a brief description of their relationship scratches the surface of his "deep feelings" for Aurelio... Which is something he'd say and call romantic. They have an inseparable bond and are rarely seen individually. He's just a little obsessed with him... Just a little.

He doesn't have a right eye, the area covered with a patch. Incessant toying and prodding objects into the remaining socket is something he enjoys and does to scare others, though it's also a fetish of his. Due to assorted things being pushed too far in, the result has been brain damage to his frontal and temporal lobes. Though, he could care less. If you ask him how he lost it, he avoids the question with a blunt answer.

Valentine shows signs of psychosis and other mental illnesses, often not understanding his own mortality, and at times reality itself. He'll have bouts of aggression where he's bitey and irritable, but they're erratic and not long-lived. He has a short temper with a few things that will instantly make him fly off the handle. And other times, he'll detach himself from the ability to feel emotions. He doesn't view himself as a god, but he feels untouchable like one, never registering that he can and will die if he's too reckless one day. In the midst of an episode he won't be "aware" of what he's saying or doing, and will have a foggy memory of it once it ends. He refuses to see a doctor or get medicated for it, having bad experiences with medication in the past. He remains undiagnosed. He can't feel much in terms of empathy besides when its directed at Aurelio. Because of this, at times he doesn't understand what he's doing wrong, the consequences of his actions, or how others truly feel. The emotional disconnect between himself and others continues to enable his behavioral issues without the ability to learn in sight.

Valentine's perception of pain and pleasure are mixed. Unable to tell the difference, he willingly throws himself into compromised positions to seek the thrill he's craving. With his job as a Hitman, Valentine isn't afraid of things like death, but is drawn to it to a detriment at times. He enjoys the blood and gore of it, and even likes being on the receiving end. Though of course what he can do with those fantasies can't often safely be enacted. Aurelio does his best to curb his lack of impulse control and general defiance, but he can only do so much, especially when he thrives off of negative attention for an excuse to retaliate. He's Valentine's biggest support when it comes to his mental health issues and refuses to abandon him even if he frequently acts out.

Due to his mental issues, hobbies, and job, he lives his unpredictable life to the fullest, never knowing when it may end. And despite all of his shortcomings he enjoys the time he spends alive, especially when it's with a man he finds cute, like Boss.

Charismatic --- Impulsive

Loyal --- Defiant

Romantic --- Short-tempered


  • Boss~!
  • Hamburgers (his favorite)
  • Dresses, especially with frills
  • The color pink
  • Scruffy beards on older men
  • Being called pretty
  • Boss' coat
  • Strong alcohol
  • Red meat, cooked rare
  • Zwiebelkuchen
  • Onions, bell peppers


  • Wearing mens' clothing, pants
  • Being alone
  • Noncommittal, indecisive people
  • Animals, for how they make a mess of fur on his clothes
  • Being told what to do
  • Piercings (with the exception of Aurelio's)
  • Being called a pirate or anything adjacent
  • Being seen without his eyepatch on
  • Children
  • Spicy food
  • Shrimp
  • Liver


  • ???


  • Going wherever life takes him
  • His job as a hitman
  • Pestering Aurelio, in various ways
  • Persuading men into spending time with him, or at least attempting to
  • Sewing
  • Katana-polishing / sharpening
  • Taking care of his absurdly long hair
  • Painting his nails


  • Despite being named Valentine, he was born on February 15th... The day after Valentine's Day.
  • Considers "Vally" a cute nickname, but hates "Val".
  • He was born and raised in Germany until leaving at a young age, so he can only speak English.
  • Even with his looks, he still has the voice, mannerisms, and speech of a... Chad, in layman's terms.
  • His silver hair is natural, but he dyes the ends yellow. He has naturally straight hair and styles it himself, only being normal in the early morning before he "preens" himself.
  • He's ambidextrous.
  • Due to his training, he's strong and can lift his own body-weight and then some. Same with Aurelio.
  • The alias "Black Widow" was given to him because of one of his "techniques" for performing a hit, but also because of something else he doesn't like to talk about...
  • He refers to his katana as "Julia" with feminine pronouns.
  • He claims to hate the idea of being in love with someone other than Boss, but will have a catastrophic, angry, emotional episode when he catches feelings for a one-night-stand.
  • He... Has a bad habit of biting people.
  • He isn't bothered by people thinking he's a woman at first. In fact, it gets him excited.
  • Likes to use pet names for people, like Baby, Cutie, and... Daddy. Boss isn't spared from it. (His preferred pet name for him is "baby" despite his age.)
  • His cooking skills are average at best. Why try when someone else can do it for him?
  • He can't drive. Not only because of his lack of a right eye, but because Aurelio is too afraid to let him try with his destructive tendencies.
  • His biggest dream is to die during sex. Well, maybe his second biggest, marrying Boss is more important.

Voice claim: Ian Sinclair

Image song: Take The Veil Cerpin Taxt - The Mars Volta

F-List (18+)

Meme playlist (a lotta stuff that reminds me of him)

He was created on April 27th, 2020.

BG source