Y/N took a sip of his cola, watching his coworkers dance and talk. He smiled softly when he saw the delighted look on his coworker's face. She's been a good friend of his for a while, so he was happy for her and her husband.
From where he sat at a makeshift bar, he took another glance around the room, and noticed his partner, Delilah, face-down on her table with a pint of beer in hand. Concerned, he stood up, and walked over to investigate.
Delilah groaned when she felt Y/N tap her shoulder, and looked up, her bangs getting frizzy. "Oh... hey, Y/N." She said glumly, resting her chin on the table. Her brownish-blackish hair swished a little as she turned to stare into her glass with her emerald green eyes.
"Uh... why the long face?" Y/N asked in joking tone. Delilah looked resentfully are Y/N, which caught him a little off-guard. "Oh, nothing... just that I'm an old hag at a young couple's baby shower when I don't have any babies of my own!" She cried, slamming her forehead on the table.
The woman was starting to cause a scene, so Y/N swooped in. "W-Well, there's always more time!" He said, trying to reassure. Delilah sniffled. "You didn't deny me being an old hag..." She murmured, tears forming in the corners of her eyes. "Hey, c'mon now. There's no need to say stuff like that. If you ask me..."
Y/N took a second to examine Delilah's... "assets".
"A lot of guys are missing out." He said. Delilah brushed away her tears. "Y-You... you think so?" She asked. "Of course. Y'know, I just might take you for myself." Y/N joked, but immediately regretted saying that. "R-Really?" Delilah asked with delight.
"H-Hey, whoa... I was just..." Y/N trailed off as he saw Delilah's smile fading. "...Wondering what our first date would be! Hehe..." He replied. Delilah's eyes shined with joy, and she started to ramble about date ideas and different hotspots she had studied on.
...
"Bye..." Y/N called, waving goodbye to Delilah as he pulled out of the parking lot. Once he was good distance away, he parked at a gas station, and slammed his forehead on the wheel, unintentionally honking. "What's your problem?!" A random voice shouted. Y/N, already too fed up to deal with anyone's bullshit, stuck his head out the window. "Get on a treadmill, lard-ass!" He shouted back.
A/N: Why is it so hard to find anime MILFs that aren't in hentai? If anyone has a good source of wholesome anime MILFs, lemme know.
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Christmas Cake (Male Reader X MILF)
General FictionY/N is celebrating his coworker's baby shower when he is approached by another one of his coworkers. She drunkenly confides in him about losing hope for marriage at her age.