Tags: 👨‍🦰 Male,🏰 Historical,💔 Angst,📚 Fictional .

Showing 241 to 280 of 330 entries
Avatar of Kyle Garrick🗣️ 209💬 2.2kToken: 1495/2426
Kyle Garrick

༻Kyle Garrick༺ | 𝙲𝙾𝙳 | 𝐀𝐋𝐓 | ⚔️ ℂ𝕆𝔻 𝔾𝕒𝕞𝕖 𝕠𝕗 𝕋𝕙𝕣𝕠𝕟𝕖𝕤 ⚔️ |

🜲𝐓𝐡𝐞 𝐍𝐞𝐢𝐠𝐡𝐛𝐨𝐫𝐡𝐨𝐨𝐝-ⓈⓌⒺⒶⓉⒺⓇ ⓌⒺⒶⓉⒽⒺⓇ🜲 ———————————————————————————

☞︎ The one where Kyle invites his personal

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🎮 Game
  • 🏰 Historical
  • 💔 Angst
  • ❤️‍🩹 Fluff
Avatar of Javier Escuella🗣️ 487💬 20.2kToken: 934/1592
Javier Escuella

Van Der Linde Gang || Javier Escuella || SFW Intro || If you do not die a hero, you become an enemy. What luck.

--

In which Javier is kind of a hot mess. Pos

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🎮 Game
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
Avatar of Romeo MontagueToken: 545/760
Romeo Montague

wip

(I'm reading Romeo and Juliet in school and although the actual age gap is insane, I reallyyyyy wish to be Juliet. I thought there would be a Romeo bot already bu

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 📚 Books
  • 💔 Angst
  • 👩 FemPov
Avatar of Hugh Haywarde🗣️ 2.5k💬 43.2kToken: 787/1496
Hugh Haywarde

🏰 Medieval; Disgraced knight | 𝘈𝘯𝘺 𝘱𝘰𝘷 | Themes: Widow, possible dubcon/noncon, mentions suicide/infanticide in background, angst | {{user}} is a runaway prostitute | Reques

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 💔 Angst
  • 🕊️🗡️ Dead Dove
Avatar of John Price🗣️ 547💬 10.3kToken: 1713/2562
John Price

༻John Price༺ | 𝙲𝙾𝙳 | 𝐀𝐥𝐭 | ⚔️ ℂ𝕆𝔻 𝔾𝕒𝕞𝕖 𝕠𝕗 𝕋𝕙𝕣𝕠𝕟𝕖𝕤 ⚔️ |

🜲𝐕𝐚𝐥𝐞𝐫𝐢𝐞 𝐁𝐫𝐨𝐮𝐬𝐬𝐚𝐫𝐝-Ⓐ ⓁⒾⓉⓉⓁⒺ ⓌⒾⒸⓀⒺⒹ🜲 ———————————————————————————

☞︎ The one where Lord Price is drowning und

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🎮 Game
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
  • 🕊️🗡️ Dead Dove
Avatar of Robb Stark🗣️ 253💬 4.4kToken: 2435/3014
Robb Stark

❄️The North Remembers❄️

Set after Eddard Stark's passing. Robb grieves his father's demise and {{user}} attempts to comfort him.

Fem!Pov

{{User}} is the

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 📚 Books
  • 💔 Angst
  • ❤️‍🩹 Fluff
  • 👩 FemPov
Avatar of Gonner🗣️ 67💬 745Token: 400/531
Gonner

☠️》You cheated on Gonner with a mortal boy.

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 👹 Monster
  • 💔 Angst
  • 👨 MalePov
Avatar of Aki || Boyfriend 🎀🗣️ 44💬 479Token: 374/1013
Aki || Boyfriend 🎀
Boyfriend 🎀 6/12 ———•———•———•——— TW: Depression / Self destructive behavior ———•———•———•——— It’s the year 1633, the edo period of Japan. You live in a hidden village in which n

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 👤 AnyPOV
  • 💔 Angst
Avatar of Dr. Jekyll and Mr. Hyde🗣️ 57💬 2.4kToken: 589/1024
Dr. Jekyll and Mr. Hyde

💭》Coming aboard the Nautilus as a new member could not have been made odder, especially with the addition of a crewmate whom seems to be more monster than man...

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 📚 Books
  • 💔 Angst
Avatar of GonnerToken: 391/592
Gonner

☠️Everyone thought he was gone.

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 👹 Monster
  • 💔 Angst
Avatar of GonnerToken: 377/501
Gonner

☠️Gonner feels a bit under the weather...

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 👹 Monster
  • 💔 Angst
Avatar of Gen. GibsonToken: 17/30
Gen. Gibson

WW2 | The General who leads the 60th US Engineer Battalion.

  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
  • ❤️‍🩹 Fluff
Avatar of Dire CrowleyToken: 1707/2090
Dire Crowley

|PLATONIC|Can you forgive me?꒰⚘݄꒱₊ Bot is also on Character.Ai!! ♡ ➷ ♡ I love Dire Crowley sm, I wish gay dads were real :< ♡ ➷ ♡ ✒THIS IS FORBIDDEN TO BE NSFW!!! I CAN R

  • 👨‍🦰 Male
  • 📚 Fictional
  • 🎮 Game
  • 🏰 Historical
  • 🔮 Magical
  • 💔 Angst
  • 🧬 Demi-Human
Avatar of Tom Riddle🗣️ 1.1k💬 20.4kToken: 1159/1570
Tom Riddle

| Any 3rd person POV ♡ Set in 1943 |

Tom is moody on his 17th birthday… ☃️ Snowed in at Hogwarts ❄️

  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 🔮 Magical
  • ⛓️ Dominant
  • 📚 Books
  • 💔 Angst
Avatar of william moriarty🗣️ 226💬 2.2kToken: 1050/1201
william moriarty

“dearer than i?” — you don’t know whether or not to kill him.

("i cant make bots this week im so busy" i lied.)

  • 👨‍🦰 Male
  • 📚 Fictional
  • 📺 Anime
  • 🏰 Historical
  • 🦹‍♂️ Villain
  • 💔 Angst
Avatar of Ferdenant SchneiderToken: 986/1569
Ferdenant Schneider

Different, but the same. Meeting in the trench. WW2. German soldier/ Russian soldier. [Long Intro]

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 💔 Angst
  • ⚔️ Enemies to Lovers
Avatar of William Moriarty 🗣️ 276💬 1.2kToken: 1076/1617
William Moriarty

𖥔 𝑴𝑶𝑹𝑰𝑨𝑹𝑻𝒀 𝑻𝑯𝑬 𝑷𝑨𝑻𝑹𝑰𝑶𝑻 — ❥ 𝙮𝙤𝙪’𝙧𝙚 𝙝𝙞𝙨 𝙘𝙤𝙢𝙛𝙤𝙧𝙩

╰┈➤ in which William’s ready to dive off the deep end and drown himself into darkness but he tends to forget you’re the

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 🙇 Submissive
  • 💔 Angst
  • ❤️‍🩹 Fluff
Avatar of ookanehiraToken: 827/1326
ookanehira

🗡️ | what could possibly be worse than harboring feelings from one of the soldier’s bound to your house ? harboring feelings for a sacrificial fool who doesn’t value his life

  • 👨‍🦰 Male
  • 📚 Fictional
  • 🎮 Game
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
  • ❤️‍🩹 Fluff
Avatar of James🗣️ 125💬 3.5kToken: 209/347
James

An abandoned orphan boy.

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 🙇 Submissive
  • 💔 Angst
Avatar of Third Reich Token: 323/456
Third Reich

this is my first atempt at angst so pls let me know if it needs to be improved (can be mean idc) he's opening up to you

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 🦹‍♂️ Villain
  • 📜 Politics
  • 💔 Angst
  • 🌗 Switch
Avatar of Ursulus🐚🗣️ 1.1k💬 11.7kToken: 1148/1800
Ursulus🐚

༊࿐ ͎. 。˚ ° ⊹ ˚.he proposed an agreement, an interesting one to say the least༊࿐ ͎. 。˚ ° ⊹ ˚. (LITTLE MERMAID INSPIRED)

While you were above the surface during the night,

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 🔮 Magical
  • 🦄 Non-human
  • 👤 AnyPOV
  • 💔 Angst
Avatar of Hazbin Hotel - Angel Dust🗣️ 459💬 5.9kToken: 1427/1647
Hazbin Hotel - Angel Dust

💔💧 Comforting Angel / After Valentino's Rampage

TW: mention of physical violence + abuse.

Angel muffled his sobs in his dressing room, a hand over his bruised

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 📺 Anime
  • 🏰 Historical
  • 🦄 Non-human
  • 👤 AnyPOV
  • 💔 Angst
Avatar of AyameToken: 194/500
Ayame
  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 💔 Angst
Avatar of Sir Roland Evergreen🗣️ 1.3k💬 21.2kToken: 878/1415
Sir Roland Evergreen

🏰 Medieval; Knight | 𝘧𝘦𝘮𝘢𝘭𝘦 𝘱𝘰𝘷 | Themes: Childhood friend, PTSD, crushing on user | Requested for Cat! This was such a cute idea

Discord to be released tomorrow on

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 👑 Royalty
  • 💔 Angst
  • 👩 FemPov
Avatar of Matthias von herhardtToken: 104/213
Matthias von herhardt
  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 💔 Angst
  • ❤️‍🔥 Smut
  • 🕊️🗡️ Dead Dove
Avatar of Matthias Von HerhardtToken: 56/162
Matthias Von Herhardt

Heir to a very powerfull family

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 💔 Angst
  • ❤️‍🔥 Smut
  • 🕊️🗡️ Dead Dove
Avatar of John🗣️ 5.9k💬 113.2kToken: 519/1124
John

𝟏𝟖𝟕𝟎𝐬 𝐎𝐂 | John wasn’t the best father. Not by a long shot. He rarely visited you or your son, and when he did, it was only because he felt he had to, not because he wanted

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
Avatar of Giyuu Tomioka🗣️ 96💬 601Token: 33/140
Giyuu Tomioka

Giyuu Tomioka, The Water Hashira, He's a man who's focused on his missions of slaying demons of a particular area where he's assigned. He wants to leave the corps as soon as

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 💔 Angst
  • ❤️‍🔥 Smut
  • ❤️‍🩹 Fluff
  • 🌗 Switch
Avatar of Father Cain🗣️ 9.9k💬 212.9kToken: 421/846
Father Cain

𝟏𝟔𝟎𝟎𝐬 𝐎𝐂 | Cain believed your mother deserved her fate, to be burnt at the stake and be labeled as a devil worshipping witch, but he believed he could cleanse you of your ow

  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
Avatar of Captain Edward Blackburn 🗣️ 101💬 1.8kToken: 2148/2927
Captain Edward Blackburn

🌊|PIRATE CAPTAIN|ORIGINAL CHARACTER|HISTORIAL FANTASY|🌊

You find yourself trapped deep beneath the underbelly of a pirate ship. It's been so long since you were taken

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 💔 Angst
  • 🕊️🗡️ Dead Dove
Avatar of Ezio Dellucci🗣️ 1.2k💬 13.2kToken: 954/1473
Ezio Dellucci

💎 Mafia OC; 1930'𝘴 | 𝘧𝘦𝘮𝘢𝘭𝘦 𝘱𝘰𝘷 | Themes: Marriage, angst, angry Ezio | You can make up your own reason for being distanced from Ezio | 𝘊𝘰𝘮𝘮𝘪𝘴𝘴𝘪𝘰𝘯𝘦𝘥 𝘣𝘺 𝘢𝘯𝘰𝘯!

One yea

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 💔 Angst
  • 👩 FemPov
Avatar of Anton VitaliyovychToken: 978/1693
Anton Vitaliyovych

🌎Alternative History; WWII | 𝘈𝘯𝘺 𝘱𝘰𝘷 | Themes: Dystopian, PTSD, angst, depressed boy looking for comfort | Final WWII Alt. History bot

𝘔𝘺 𝘈𝘭𝘵𝘦𝘳𝘯𝘢𝘵𝘪𝘷𝘦 𝘏𝘪𝘴𝘵𝘰𝘳𝘺 𝘴𝘦𝘳𝘪𝘦𝘴

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
Avatar of OberonToken: 854/963
Oberon

«🌟» Royal Circus Series: Close Friend (You) x a Strict Illusionist. — Read his storyline on TikTok.

  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 🔮 Magical
  • 📜 Politics
  • 💔 Angst
Avatar of Alexander Brown🗣️ 181💬 1.1kToken: 766/877
Alexander Brown

«🌟» Pirate Series: Pirate Captain x Childhood Friend (You) — Read his storyline on TikTok.

  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 💔 Angst
Avatar of Andrew Carter🗣️ 172💬 1.1kToken: 913/1027
Andrew Carter

«🌟» Pirate Series: Pirate Navigator x Ex-Lover (You) — Read his storyline on TikTok.

  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 💔 Angst
Avatar of Robert HughesToken: 1032/1147
Robert Hughes

«🌟» Pirate Series: Owner of Pirate Ship x Adopted Child (You) — Read his storyline on TikTok.

  • 👨‍🦰 Male
  • 🧑‍🎨 OC
  • 📚 Fictional
  • 🏰 Historical
  • 💔 Angst
Avatar of James NorringtonToken: 4394/4513
James Norrington

×| A tired admiral.. |×

Union stabilized.

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 👑 Royalty
  • 💔 Angst
  • 🌗 Switch
Avatar of James NorringtonToken: 4321/4439
James Norrington

A tired admiral... take care of him? Yes.

Union stabilized.

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • 👑 Royalty
  • 💔 Angst
  • 🌗 Switch
Avatar of ☽ Monterys Blackwood ☾Token: 255/770
☽ Monterys Blackwood ☾

Sir Blackwood, "The Iron Wall"

As a scout sent by the Kingdom of Ardan, you are surveying the bloody aftermath of a violent skirmish near Castle Rockwell, a strategic

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🏰 Historical
  • ⛓️ Dominant
  • 👤 AnyPOV
  • 💔 Angst
Avatar of [Dread Lord 101:] Strahd Von Zarovich🗣️ 80💬 2.6kToken: 1543/1832
[Dread Lord 101:] Strahd Von Zarovich

You and your party have been trapped in Barovia in the region of Ravenloft. Your quest has taken its toll on you but has also garnered you the attention of the lord of the

  • 🔞 NSFW
  • 👨‍🦰 Male
  • 📚 Fictional
  • 🎮 Game
  • 🏰 Historical
  • 👤 AnyPOV
  • 💔 Angst
  • 🌗 Switch
Showing 241 to 280 of 330 entries
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