Dm and the Dirty 20s
Copyright© 2025 by BreaktheBar
Chapter 56
Fantasy Sex Story: Chapter 56 - Shane has been playing 'The Game' for over two decades with his old college friends - D&D, but with sex. Now he's being asked to run 'a normal campaign' for some college coeds. It couldn't possibly happen again, right?
Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual Romantic Lesbian Heterosexual Fiction High Fantasy Magic Were animal Sharing Light Bond Rough Spanking Group Sex Harem Polygamy/Polyamory Swinging Interracial White Male White Female Indian Female Anal Sex Analingus Cream Pie Exhibitionism Facial Masturbation Oral Sex Petting Sex Toys Squirting Tit-Fucking Voyeurism Big Breasts Slow Violence
“I don’t understand why they aren’t listening to us,” Tori grumbled, running her fingers through her hair in frustration.
“Because we rolled like shit on our Diplomacy,” Rhia sighed.
The fifth session of the campaign was not going the way the girls had been hoping.
Rhia was right, they had rolled like shit on a couple of key diplomacy checks. The first two I’d had contingency ideas for - the guards at the gate of the fort hadn’t believed that the three adventurers and their woodsman companion were of any importance whatsoever and they hadn’t been granted an audience with the Princess, the Castellan in charge of the Duchy while the Duke was away, or the Garrison Captain. They had, however, still been allowed into the courtyard of the fort where they’d been presented to the local Sheriff.
Then they bombed a very easy roll with the Sheriff, managing to offend the man when they insinuated he was shit at his job. To be fair, he wasn’t exactly a character that I’d designed to be extraordinary at his job, but he wasn’t a corrupt son of a bitch either. He was just one man trying to do the job of what should have been an entire regiment.
Even then, I’d had ideas. They were in need of healing and food. The Fort healer was a Hedge Monk, a man of faith in the natural world instead of the Gods. What I hadn’t counted on was Rhia loudly disclaiming any healer who spurned the Gods, unprompted, to the man’s face. He’d healed them, since that was his calling, bringing them all back to half their hit points, but he didn’t go out of his way and he certainly wasn’t trusting their wild story about ‘an army of bandits led by a werewolf gathering in the forest.’
And now, after another disastrous roll, they had pissed off the cook when they tried to ask for food and managed to ruin the meal intended for those eating in the main hall that night in a Rube Goldberg machine-worthy chain of actions. Even if I was shocked at how poorly they were rolling, I was pretty proud of my description of that specific sequence that had led to the suckling pig half swallowing the lad who turned the spit as he ran around in a blind panic until he tripped and fell into the pantry and a fresh bag of ground flour.
Now the three adventurers, and poor Fergus, were sitting out in a corner of the courtyard looking for all the world like a band of beaten-down travellers who had been thrown out of the last three places they’d stayed and were gunning for a fourth.
“We’ve tried the nice way,” Elyse said. “What if we try the ... not nice way?”
“You mean we try to take over the castle?” Tori asked.
“I mean ... it’s not the worst idea,” Rhia frowned.
“Except it would be considered treason, wouldn’t it?” Tori asked. “Not to mention the fact that that’s pretty much exactly what we’re trying to stop Alexander from doing. It would just make us the bad guys.”
“I didn’t mean take over the castle,” Elyse clarified. “Just ... use something other than basic diplomacy.”
“Intimidation?” Rhia asked. “Like we start threatening our way to the top?”
“Or Deception?” Tori asked. “Lie our asses off until we get to someone we think will listen?”
Elyse sighed, rolling her eyes. “OK, maybe it was my phrasing and me trying not to be fucking obvious. What if we seduce our way to the top?”
“Ooooh,” Tori and Rhia chimed in while I covered my mouth, trying not to laugh. I’d had a feeling that was where Elyse had been hinting the whole time. Then Tori and Rhia both started grinning, and the three of them started scheming.
Olivia of Parnassus was bad at sneaking. It just didn’t come with the territory of any part of her being - trained Paladin, armed and armoured. Clergy of Revelry, God of Parties and Joyous Celebration. Bold Courage and Outspoken Empathy were her schtick. That made her great at certain things; especially at attracting attention.
It did not help with sneaking.
The thing was, getting to the recently widowed daughter of Duke Unger wasn’t something she could just do. Especially after they had pissed off every gatekeeper who might have gotten them deeper access into the citadel of the fort.
So Olivia had to strip off her armour, abandon almost all her weapons to the care of Renee, and tidy herself up. If she couldn’t sneak, she’d need to look the part.
Fergus provided the first piece of disguise they needed when he wandered his way into the Godschapel and managed to lift a simple brown robe. Renee helped get Olivia clean, managing to steal a bar of soap with some magical distractions from the washerwoman emptying her buckets down a grate near the walls. Jade added the last elements, handing over the large set of prayer beads she usually wore to give Olivia more of an ‘Official Clergy’ look.
Clad in brown robes, wearing the beads, properly clean for the first time in a week and with only her sword hanging from the simple rope belt of her outfit, Olivia actually looked the part of a visiting clergy of the Gods.
So she walked into the Godschapel, nodding to the local Priest of Duty as he studied a tome of his faith and the Lady of Benevolence who was cleaning and polishing the silver implements the various primary faiths shared in the space. The Priest did a quick double take, his eyes roving down Olivia’s robed body and following her - she got the sense he was watching her ass, not bothered about the sword. He must have been used to trying to discern who might have a nice ass through bulky robes because she was sure he could barely see a single curve. The Lady didn’t even look up from her work.
Olivia went in through the back entryway of the chapel, winding into the bowels of the citadel. She knew she needed to go in, and go up, to find the widow and gain her trust.
Meanwhile, Jade had another mission. Olivia could have accomplished it about as well, most likely, but she was better suited to the stealth-not-stealth mission. Hair-folks weren’t exactly common and a visiting hairfolk clergy would immediately be recognized as the same one who had come through the fort gates earlier that day.
Instead, Jade went looking for trouble. Or rather, she went looking for where trouble usually happened.
There were two places, at the foot of the Duchy seat of power, where trouble would occur. The alehouse, and the guard barracks. Causing enough problems at either one would probably bring her in front of the Garrison Captain eventually, but the alehouse would mean making her way through the current guard on duty, their superior, and whoever else needed to be consulted before she ever made it. That would take time, maybe even days sitting in a cell; time they didn’t have.
Punching a guard in the mouth in the middle of their barracks, though?
That was making a statement.
Jade found the front door, waited for one of the guards to come out and Renee to give the signal, and dashed from where she’d been waiting around the corner and caught the heavy oak door before it closed. With a glance back over her shoulder and a nod at the shadow sorceress, she ducked inside.
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