Roleplay Night

by Shakespearicles

Roleplay Night

Previous Chapter

"Hey," Velvet said. Twilight blinked awake and looked up at her mother leaning over her. "Welcome back." She handed her a bottle of electrolytes. "Here. You lost a lot of fluids."

Twilight took the bottle and sat up in her mother's bed. Still nude and sticky from their lovemaking. Her eyes slowly adjusted and focused on Velvet, dressed in Twilight's school uniform again.

"So what's the deal with that, really?" Twilight asked.

Velvet blushed. "It's kinda weird and embarrassing."

"Mom, you just fucked my brains out and I swallowed like, a pint of your orgasm! I think we're a bit past the point of modesty."

Velvet turned a deeper shade of red. "It's... it's a roleplay thing. That I wanted to do with your father. I want to roleplay as... you."

Twilight balked. "Dad wants to have sex with me!?"

Velvet laughed. "I'm surprised that surprises you, Twilight! You're a young, attractive girl. And your father is very much a man."

"But I'm his daughter!"

Velvet just stared at Twilight staring back at her. "Kettle, meet pot."

"You know what I mean!"

"I know what you mean, Twilight. But it's also not what I said," Velvet explained. "I want to roleplay as you, with your father. But that doesn't mean that it's for your father."

"I'm so confused."

"I don't want him to be himself." Velvet said, going into the bedroom closet to dig out Night Light's old Royal Guard uniform. "I want Night Light to roleplay as Shining Armor."

"..."

"..."

"WHAT!?"

"I didn't stutter, sweetie."

"So you want to... both roleplay at the same time... as Shining and I, with each other!?"

Velvet nodded.

"But... but why!?"

Velvet sighed and sat on the edge of the bed. "You sound just like your father. Judgmental. Who would have thought that Night Light, a librarian of all people, could lack imagination?"

"Mom, I..!" Twilight took a deep breath and forced herself to relax. Still nude, she sat on the bed next to her mother. "I'm not kink-shaming. I'm just kink-asking-why."

Velvet reached over and held Twilight's hand. "There's a reason why your uncle Velcro never visits. There's a reason why your Grandma Suede used to say to me, 'Velvet, I hope you never have kids.' And that cut me so deeply!" Her eyes glistened as she looked over at her nude daughter sitting beside her. "Maybe she was right."

"Oh."

Velvet looked down at the clothes she was wearing in shame. "The idea of you and Shining having sex just turns me on so much! And... I wanted to act it out to fulfill that fantasy with Night Light. To give me ideas for my next book. He obviously didn't want to. But every once in a while..." she looked at herself in the mirror, "I still like to dress up and pretend."

Twilight put her other hand over her mother's. "Well, if there's one thing that Principal Celestia has taught me, is that there's no wrong way to fantasize."

Velvet looked at her and smiled. "Thank you, Twilight. You don't know how much I needed to hear that."

Twilight stood up and picked up the royal guard uniform and the strap-on harness. "So... are you going to put this on and play the part of Shining?"

"What!? No!"

Twilight was extra confused. "Wouldn't it make sense for you to do that, and for me to just be myself?"

Velvet visibly recoiled. "No. That's not roleplay! That would be like me wearing this to indulge your father as himself." Velvet got up to help put the strap-on harness on Twilight. "You wear this..." she instructed, "And put on this..." She dressed Twilight in the Royal Guard uniform. As soon as she finished, she stepped back and looked at Twilight.

Twilight looked down at herself in the uniform, and then at herself in the mirror, opposite Velvet, dressed up as her.

"Ooh, Shiny! Is that a spear in your pocket or are you just happy to see your little sister?" Velvet said.

Twilight looked back down at the silicone dildo hanging out of the unzipped uniform pants.

"It's a strap-on," Twilight deadpanned.

Velvet dropped to her knees in front of her and started stroking the strap-on. "Ooh, your peepee is so big!

"Peepee!? Wait, what age are you playing?"

"It looks just like Daddy's!"

Twilight looked at the dildo. "Probably because it was modeled after his... Wait! How would I... you, even know that Dad's dick looks like in this scenario?"

Velvet ignored the question and turned around to rub her butt up against the dildo, pulling it down under the skirt between her legs. "Come on Shiny whiny! Don't you want to stick your big ol' corn dog inside your little sister?"

"Corn dog!?"

"Ooh, Shiny, I need it so bad! Please put it in! I'm so teenage-horny!" Velvet begged.

"Is that really what you think I sound like!?"

"Let me just get changed. Since you're my big brother, I can trust you." Velvet bent at the waist to pull her panties down. "Oh no! You can see my little teenage pussy! I hope you aren't overwhelmed with lust!" Velvet's magic shoved at Twilight's back, pushing her forward, and guiding the dildo into Velvet's pussy. "Oh Shiny! You're so forceful! Overpowering your vulnerable little sister! You took my virginity! I hope I get my cutie mark for this!"

"Wait! I'm a blank flank in this scenario!?"

Velvet's magic guided Twilight's hips. "Oh Shiny! You better not cum inside me!"

Twilight looked at the silicone dildo she was wearing. "Yeah, I don't think you need to worry about that."

"You're going to get me super incest pregnant!"

"The fuck!? What, is the baby going to come out wearing a cape!?"

"Oh no! What if Daddy catches us? You'll have to fight him for rulership of the homestead!"

"The what of the what now?"

"You'll get to claim mommy too and make him watch!"

"Okay, yeah, I can see now why Dad doesn't want to do this with you."



Twilight Sparkle stood in front of her bedroom mirror, carefully applying the temporary dye in her hair to give herself white and purple stripes as she described what happened to her boyfriend.

He rubbed the dark-blue dye into his hair. "Wait, she did what!?"

"She said that she likes to do incest roleplay as me."

"Wow."

"I know, right!?" Twilight laid in the bed dressed up as a boring author. "Anyway, I'm ready for sexual intercourse with my husband for the sole purpose of procreation."

The guy dressed as the lame librarian climbed into bed with her to begin having sexual intercourse with his 'wife', for the sole purpose of procreation. "What did the grape do when it got stepped on?" he asked as he pressed the tip of his dick into her pussy.

"What?" she asked, feeling his dick slide deeper inside her.

"It let out a little whine," he said as they started fucking.

"Your dad jokes are getting worse, Night Light," she said.

"Thank you Velvet," said Shining Armor.