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You Said You Wanted to Roleplay! Oh, You Didn't Mean D&D? [FM] [Comedy] [Shibari] [D&D Erotica]

Updated: Apr 8, 2022

You know, there's always been the joke about getting the whole "role-playing" thing mixed up. One person wants d20s rolling for initiative, and the other wants their eyes rolling in the back of their head as they cum while bound and tied together. Has it ever happened before? I have no idea. Is it happening right now?

Well...

"Come on! Pound my ass!"

I look up from my character sheet and see Penny wiggling her butt in the air, desperate for me to give her what she wants. I blow out air in exasperation and roll.

"Let's see..." I say, checking over my sheet. "That's a thirteen on the die, plus three for proficiency in ropes, a plus two from dex, for an uh...Shit that's ummm..."

Dammit, why is basic math so hard when doing this?

"Eighteen!" She shrieks, staring at the wall while blindfolded. "My AC is only 11 right now and I'm restrained!"

"Oh you're right!" I shout, pulling out my lucky metal dice. "That means I get advantage."

I look over at Penny who's arms are tied together behind her back. She's also got diamond pattern knots along her back. I tied a single rope with some extra soft rope across her vagina, which is currently up in the air, dripping onto my floor. Her impatient moans excite me even further.

"Come on, just do it! It's already an automatic crit because I'm restrained!"

I make a face she cannot see at the idea of not rolling the precious shiny math rocks. Seriously! I'm not the one who brought bondage gear to a D&D-themed date! What else could a Bad Dragon mean? Oh well.

"If we're gonna do this, we're gonna... NATURAL TWENTY!!!!"

I let out a roar of excitement as the dice gods smiled down on me. Who cares if I was using a crit on an already vulnerable mob? The nat20 knows no tactics nor plans. Only drama and excitement.

"YESSSS!" Penny screams as I shove my cock down her tight wet pussy. "Ohhhh fuck yes, I'm a bad little cultist you need to punish. Oh fuck yes, you big strong, burly adventurer, more! More! Pound me into the fucking dirt!"

Suddenly, I'm transported into a misty cave, surrounded by totems to the Death God Burazaqq the Unrelenting. Kneeling on the ground, I hold the cultist leader Pennarad by the hair. I've got her tied up to be taken to the townsfolk.

"You're going to pay for what you did!" I grunt, feeling her lithe body shiver at every thrust. "Those sheep had families!"

The cultist turns and looks to me, her tongue hanging out and her one eye filled with regret. The other is shrouded in darkness.

"I'm sorry, brave Fighter! I'm sorry for my sins! Forgive me, please! I'll do, ahhh~, I'll do whatever it takes!"

I blink for a second, and I'm back in my apartment.

"Uhh Penny?" I say, dropping the macho voice. "I'm a ranger not a fighter."

Penny looks over at me, with the blindfold slipping down the right side of her face. Her pale, freckled face is now bright red and flushed.

"Right, sorry. Let's try that again." She turns around and starts thrusting her hips backward at me, reinitiating. "Oh brave, and handsome Ranger! I promise to the heavens I will do whatever it takes!"

I feel my cloak of resistance help as I roll to save from blowing my load. That's at advantage, so two rolls to the side while I grip Penny's rope cuffs.

"Nineteen!" Shout triumphantly. "You will indeed pay for your sins!"

Pennarad lets out a moan of pleasure and squirms in place, unable to move her arms or legs.

"Yes! Nineteen of your children, I will have them all!" She shrieks into the heavens, erupting the room with light. "I will bear your mighty sions and bring back the good in the world I foolishly took away."

She tightens her grip on my greatsword, and I feel my breath tighten. As I use my free hand to grab onto her ponytail, I can tell it's going to be another saving throw.

"My hands are full Pen," I grunt, yanking on her hair and cuffs. "You mind rolling?"

"Sure!" She squeals as her hips shake. "I'm so close!"

"Me too..." I say, biting my lip to stay focused. "This'll be a hard save, so make the DC 20."

I hear the clatter of dice in front of Penny as she rolls. I continue to thrust and imagine the cultist moaning in the arms of the adventurer. Me, the Ranger who traversed her cave, destroyed her cursed amulet, and defeated the young blue dragon she kept as a pet.

"T-That's a five on the die for the first r-r-r-roll." She struggles to say. I can feel my member swelling and ready to burst at any moment. "what's your modifier?"

"I've got a plus three to Con, but not for saving throws, so that's an eight."

Plap! Plap! Plap! Plap! Plap! Plap! Plap!

"B-but you've got advantage because of your Cloak so," Another clatter of the dice. "NATURAL ONE!"

As if by magic, all power in my core drains, and I've reached my limit. With one final pull of her cuffs and hair, I thrust as deeply into her from behind as I ever had before. Penny's toes curl, and I can hear her scream at first before going so high in pitch she goes silent. I hold her in place as I flood the cultist's womb with my heroic seed.

"Fffffuck..." She moans. "The first of nineteen adventurer..."

As I come down from the high of my short eternity in pleasure, her words register with me.

"Nineteen?"

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