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I've kinda rebooted Vlad and Milo's early relationship just so I can do cute stuff like this (not that they're any less horny!)
After their first ever date together, Vlad sends his friend Milo progressively spicier texts, eventually convincing the jackal boy to at least send him a picture of him in his undies. Something Milo eventually concedes to after arranging his briefs as best he can to hide as much of his bulge as possible. After Vlad accuses him of stuffing a sock in his underwear, Milo's hand is forced and the body-shy boy sends his friend a full on picture of his Gross and Weird Penis. Contrary to his expectations, instead of Vlad ghosting him, Milo receives a blurry picture of Vlad's much more normal junk along with one of the grinning maned wolf with a full on boner!
Milo, although convinced his dick is even weirder looking when it's hard, had played enough Wizardry and Poggérman to know when he's lost and reluctantly snaps a picture of his oversized jackal hard-on and after several minutes of panicked hesitation (and quadruple checking to make sure he's not mass sending it to everyone on his contacts list) hits the send button and anxiously waits for a response. Although instead of a text, he's surprised to receive an incoming call from his friend!
Not Pictured: Vlad extolling the virtues of Milo's large cock, Milo bashfully asking if it would be weird if they both were touching their boners while on a phone call. A promise of hanging out again, possibly with hand holding!