I just finished my first playthrough of Date Everything! This game is so rich in stories, characters, and options that it almost hurt to put some of these people in the tier that they are in. Some of them are in the tier level because I didn't explore them enough, or I accidentally got a hate ending so I was not able to figure out their deal. This is all just my opinions and with 100+ characters that you can interact with, you are bound to find the ones that fit your fancy.
Kintober 2025 Day 7: Blindfolds + Chastity + Bloodplay
**Note: prettyyy extreme masochism on his end
Fandom: Date Everything!
Character: Friar Errol
Friar Errol was a pious man. A very, very pious, faithful man. But here he was, soft wool pulled over his eyes, arms bound behind his back, connected to the back of a heavy collar around his neck by a chain as he knelt before you like some sort of offering. And, of course, a brass chastity cage fastened between his legs, clinking against the hardwood floor each time he shifted.
You leaned back in your soft armchair, allowing him to press his forehead to your thigh while you took another long sip of your wine. It was such a serene evening, nothing but the soft sound of rain outdoors and the heat of the nearby fireplace playing on your senses. He, however, seemed far from calm. He was shaking, hands clenching and unclenching in his restraints, bare skin flushed around the pale edges. You gently ran your fingers over his head, and his breath stopped, then stuttered out in a gasp, his cheek squished against your leg.
“You seem tense.” You spoke smoothly, letting your fingers brush over the nape of his neck. He let out a raspy groan, almost akin to a displeased growl. But he was no wolf, not like this. In fact, his rosy skin and helpless position made the image of a lamb pop into your head.
“I am no such thing.”
“Then why do you shake?”
His lips twitched down. “It is cold.”
“By the fire?”
He went silent. But it did little to hide his truth, you knew exactly what his hesitance to speak meant. You hummed, tracing your fingers down his jaw and tilting it up with two. His lips fell ajar, but he obediently lifted it. He couldn’t see you, but you could observe every drop of sweat on the crown of his head, every puff of breath that fanned against your wrist. You took another sip of your wine, then moved down, placing the rim on his lips and tilting it back to pour some down his throat. He let out a surprised sound, choking on the bright red wine as some dribbled down his chin, falling onto his bare chest.
He looked good in red.
You pulled it back and drank the rest, looking down at his face, tongue trying to gather all the stay drops he could reach, completely unaware of what you could be planning above him.
“Brace, love.”
He tensed on command. You curled your fingers around the stem of the glass tightly, gently caressing his chin with your other hand, then smashed it over his head.
It connected with his jaw, shattering on impact. The blindfold protected his eyes, but not the rest of him. He let out a pained, strangled gasp as his head cracked back, small cuts crisscrossing his skin. Glass littered the floor, shimmering in the light of the fireplace like tiny stars. You didn’t give him much time to recover, giving him a swift kick in the ribs, making him double over, groaning. You watched as his cock twitched desperately against the confines of the chastity cage, unable to even reach an erection despite how badly he clearly wanted one.
“Mm… you know, most men would be horrified by such an act.” You watched a line of drool, mixed with blood, fall down his chin. You pressed your thumb to one of the cuts on his cheek, smearing the blood across his cheek. “The last thing on their minds would be arousal.”
He weakly raised his head, teeth gritted together, face twisted in pain and dusted red with a mix of shame and arousal.
“What if your god saw you like this? His most loyal holy man, rubbing his knees raw kneeling for a sinner?”
“That’s– not fair.” He whined out, chains clinking as he shifted.
“It’s very fair. Who are you but a filthy heretic?”
The word seemed to send a shiver through him, but he couldn’t deny it. “Our lord… sees all.” He hissed out, drops of blood decorating your floor in a shining tapestry of crimson shards, and you suddenly understood why god favoured stained glass. “This is not who I am, but who you reduced me to.”
“Then you were mighty, but you’ve fallen.” You hummed in thought. “Some would call that worse than never having risen in the first place.”
He swallowed thickly, but you tired of this meaningless chatter. You placed a boot on his chest, standing out of your seat to push him back onto the floor. He gasped as his shoulders pressed into a field of sharp glass, the position no doubt uncomfortable with his hands tied like that. You pushed down harder, pressing out body weight down onto his sternum, forcing his back further into the glass. He tried to keep himself silent, but little pained whimpers fell from his lips, little sobs that filled the serene air, tears wetting the edges of his blindfold. You moved down, one knee pressed to his stomach and the other on the floor. You took his jaw in your hand, cradling it like a lover would, and kissed him. With every bit of sweetness and tenderness he had been deprived whilst your floor was being soaked through, marked with his blood.
You pulled back, lingering on his lips for a moment. “How do you feel?”
He replied with a little sniffle, breath coming out in stuttering gasps. “You… cruel, blasphemous, tempting…”
You kissed him again, relishing the way he melted into it despite everything. Perhaps it was simply in his nature to worship, latching onto anyone who stood above him. You kissed his cheek next, then leaned back, grabbing one of the larger shards of glass from the floor. He flinched as the sharp edge rested on his bared throat. You held it so close it just barely grazed his skin, parting his pale flesh just enough to let a trickle of blood fall to his collarbone.
“My beloved…” He groaned out, voice weak and shaky. “Don’t hesitate a second longer.”
