Dm and the Dirty 20s
Copyright© 2025 by BreaktheBar
Chapter 57
Fantasy Sex Story: Chapter 57 - 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
Even though Tori was currently topless - and God every time she pulled those damn perfect breasts out I had to take a split second to not drop my jaw a bit - we couldn’t get right into the fun part.
“The Garrison Captain sees you unlacing your trousers, looks back at your breasts and you can see his cock swell a little in his fist. Then he nods and starts to shift on the cot. However,” I said, putting a hand on Tori’s waist to stop her from fully disrobing quite yet as I turned to the others.
Olivia strode with purpose as she worked her way through the lower corridors of the keep. It was a bit of a maze, cramped in places and dimly lit - all part of the planned defence. If armoured invaders were to try and fight their way in they would be facing a difficult time every step of the way.
It was only once she stumbled on the interior entrance to the kitchens that she was able to start to triangulate where she was properly, and the kitchens needed access to the upper floors. She found the stairwell, cramped and steep, and made her way upward, bypassing the main level where the great hall would be and other areas that would be more likely to be populated by folks willing to challenge her presence. She made it up to the third floor, the top of the main keep, and was crossing through the corridors looking for the living quarters of the Duke’s family when she was stopped by an officious-looking elderly dwarf man.
It took some work to convince the long-serving chamberlain that Olivia was, in fact, supposed to be where she was. Her explanation relied on the fact that she was from Parnassus, where funerals were celebrations. She had (supposedly) heard about the unexpected death of the Lady’s husband and as a clergy of Revelry she had come to give counsel and succour to the widow if it was needed.
The reasoning was complete improv from Rhia, and I had to make a note to myself about this addition to my world. Parnassus was a city that I’d been avoiding for a long time, using it as a sort of near-mythical location that people would hear about but where adventurers weren’t needed because it was a lawful bastion of good. It was such a good improv, however, that I gave her advantage on her roll to convince the chamberlain - which saved her butt. Her first roll was a natural 1, which would have definitely gotten her thrown out of the keep, but her second was a 17 which brought her total over 20. And many sighs of relief were heard around the table.
“Let me show you to the Lady’s chamber, my dear,” the curmudgeonly Chamberlain grumbled, ushering Olivia around a turn in the corridor. “Now, please do remember that you are not being given full access to the family chambers. No wandering around and such! The Duke’s chambers must remain untouched for his eventual return.”
“Of course, I wouldn’t think of wandering around,” Olivia assured the elderly dwarf. “That would be entirely unacceptable for a guest of the family.”
“Too right, too right,” the chamberlain nodded. “We’ve had several young folks think that they might be able to find some sort of riches or some such hidden away in the Duke’s chambers. The ones we catch, I tell them they are buying into rumours that are entirely untrue. The Duke’s treasury was dedicated to the war over a decade ago. The ones we don’t catch, well, one of the Duke’s good friends prepared some ... interesting means of keeping his private chambers private.”
“I ... see,” Olivia said, her Adventurer-Brain immediately wondering what the Duke was protecting if it wasn’t his duchy treasury.
“Here we are,” the chamberlain said, then used his walking stick to knock on the heavy oak door - it was unadorned, and Olivia realised she would have been checking doors blindly if she hadn’t managed to convince the dwarf to help her. “Lady Aileen,” he called through the door. “You have a visitor.”
“What sort of visitor?” Elyse called, surprising Tori and Rhia. I’d surreptitiously texted her about playing the widow once the girls had made their plans, and she’d readily agreed. She even covered her mouth with a hand, smiling over it with her eyes, to mimic the door muffling her voice.
“A-” the dwarf turned to Olivia, “I’m sorry, I’m not quite sure what the proper title is for a member of the clergy of Revelry?”
“The proper phrasing would be Lady Celebrant, but it’s so formal,” Olivia said. “Just introduce me as a friend.”
“A ... friend has come to offer you some companionship,” the dwarf said, hesitating at not using a proper title.
“I am not interested in seeing suitors, Edmond!” Lady Aileen called.
“I am certainly not that, Lady Aileen,” Olivia called through the door, raising her voice to be heard.
The door was pulled open and Lady Aileen narrowed her eyes as she looked Olivia up and down. “I don’t know you,” she finally said.
“You do not, Lady, but my Goddess knows you,” Olivia said. “She was there when you were born, on every name day and feast day, on your wedding, and now she sends me in your grief.”
“Who are you?” Lady Aileen asked after a long moment.
“I’m Olivia,” the adventurer-in-disguise responded. “And I’m here to bring a spark of Revelry back into your life.”
“Revelry?” Lady Aileen asked, eyes narrowing again. “You’re a priestess of parties? With a sword?”
“I am,” Olivia answered simply.
Lady Aileen sighed with a little huff and then sniffed, and Olivia noticed that while she hid it well she did look like she’d been crying that day. “Fine,” she said. “You can come in. You can go, Edmond.”
“As you will, my Lady,” the elderly dwarf stooped his head, unable to bow fully.
The inside of the Lady Aileen’s chambers was nicely appointed, though not the extravagant show of wealth and luxury that one might have expected from the rooms of a Duke’s heir. There were also several strangely blank spaces throughout the primary sitting room and one of the side rooms where it looked like furniture had been removed.
“So, we’re alone now,” Lady Aileen said as she flounced onto one of the nice wooden chairs around the central hosting area. There was a needlepoint project on a stand, half-finished, and a small easel with an abandoned painting on a side table. “What is it you want, Party-lady?”
“We prefer ‘Party Bitch,’ but I’ll take it,” Olivia smirked as she unhooked her scabbard from her belt to sit down, setting her blade aside.
Lady Aileen guffawed a little at the cursing.
Olivia sighed as she got comfortable, sitting across from the widow and cocking her head as she looked at the woman.
I was riveted. So was Tori. We’d transcended roleplaying at the table for the moment as Rhia and Elyse were on pure improv acting. Rhia, as part of her preparation for her ‘mission,’ had changed out of the faux-chainmail and was wearing one of my bigger, baggy (and brown) t-shirts from upstairs to simulate her simple brown clergy robe, with the accessory of a simple rope belt. Elyse hadn’t had the chance to change into anything (and for all that I had plenty of props to aid in all the different kinds of roleplay we did at my games, I didn’t have ‘princess dresses’ on hand) but she’d pulled her colourful shadowy robe tight and done something with the belt to cinch it differently, making it a little more dress-like - at least while she was sitting down.
The thing was, for all that Elyse talked about not being the ‘actress’ of the group and focusing more on production, she was just as good as Rhia. Maybe it was because this was for fun - no nerves, no stage fright. Nothing to make her wonder if she was doing it ‘right’ because there was no ‘right.’ I’d known other theatre majors who stumbled at that point.
“You truly do grieve him, don’t you?” Olivia asked.
“Of course I do,” Lady Aileen scowled.
“No, not of course,” Olivia said, leaning forward intently. “Your marriage, just as everyone of your station, was political. Not every daughter of a Duke would feel as you do, Aileen. You enjoyed him and his company, and appreciated him, even if you didn’t love him when you were married.”
“I-” Aileen said, then rubbed her eyes. “Perhaps you’re right. And I pity other daughters of Dukes for it, but I did ... appreciate my husband. And enjoy him. But for all of that, I never gave him an heir. Love never had a chance until that was done. So I grieve him, you ‘Party Bitch,’ and I grieve all that I’ve lost with him.”
“Oh, Aileen,” Olivia sighed sympathetically.
The Lady cracked a sad grin. “I can’t marry again,” she said. “Not until my father returns and agrees to another match, and that may never happen. And if he dies, then it is the King who will send someone to marry me to secure the duchy. I won’t have a choice in the matter. I grieve happiness, Little Miss Revelry. Explain how you can help me with that?”
“Well, I could quote to you from some of my holy texts,” Olivia said. “Or I could give you platitudes, like that your Father will pity you or that you could end up married to a bright and shining hero from the war who deserves every inch of your pretty self.”
“I’ve heard it all before,” Aileen sighed and waved dismissively.
“I had a feeling,” Olivia smirked. “I could also offer you one of the more ... interesting forms of celebration that my church enjoys in times of need. But I lack the proper supplies as it’s been some time since I left Parnassus - it is also a little too long since the funeral for the proper rites.”
“What do you mean?”
“Drugs,” Olivia said. “Certains herbs and plants, when inhaled as a smoke, can bring relaxation and joy when combined with the proper rites to ensure a ‘good trip.’”
“And you don’t have any of these herbs and plants?”
“Not on hand,” Olivia said, standing and moving around the low table between them to kneel next to Lady Aileen and take her hand. “There is something else I can offer you, though. Something that other faiths often think of as mildly distasteful, or are simply too prudish to partake in due to their own insecurities. Something that, once you have learned it like an artform, will provide you with joy and revelry for years to come, even if your Father saddles you with a boar of a husband.”
“You speak of lofty goals, Olivia of Parnassus,” Lady Aileen said. “Paired with sinister caution. Will this take my mind off of my husband?”
“That, my Lady, I can assure you it will,” Olivia smirked.
“Then teach me,” Aileen said. “Teach me this art that will bring me joy and happiness, and distraction, and that can be my secret to keep from the prudish and snobby.”
Olivia put her hands on the Lady’s knees. “You truly wish to be taught? To experience the delights I can give you, and teach you to give?”
“Do I need to declare myself again?” Aileen growled. “I am not used to needing to repeat myself.”
“Then I’ll teach you,” Olivia said, before swiftly lifting the bottom of the Lady’s dress and burying her face between her legs, lapping at her pussy.
“Oh, fuck,” Elyse moaned, raising one of her skinny legs over Rhia’s shoulder as the dark-haired coed drove her tongue between the blonde’s slick, flushed labia. The Lady Aileen may not have ‘known’ what was coming, but Elyse had and she was already turned on - hell, I would have bet that Elyse had been turned on since the start of the game. Maybe since starting the drive to my place.
“That’s not very ladylike language,” Rhia murmured with a little grin before licking Elyse’s clit with the tip of her tongue.
“Shut up,” Elyse giggled, sticking out her tongue at her friend and then glancing at me and Tori. She got a grin on her face and quickly undid the belt of her robe, pulling it to fall open and shrugging her arms out of it so she was completely naked. “Oh, no, my dress seems to have come apart as if by magic. Is this part of the ritual?” she asked in Lady Aileen’s voice.
“Slut,” Tori laughed next to me, and Elyse responded by tweaking her nipples and closing her eyes as she let out a crooning moan.
I cleared my throat, dragging my eyes from the lesbian action, and turned back to Tori. She hadn’t moved from where she’d been standing next to me as we’d pivoted back to Rhia’s scene, and she’d put a hand on mine as it had slid from her waist to her hip, keeping it there. Now, with my movement, she peeled her eyes away from her friend and her roommate as well and flushed a little as she realised now was the time to get back into our scene. She let out a breath, smiling nervously.
“Do you need a second?” I asked quietly, not wanting to interrupt the others.
“Maybe just, um, get into position a little more like the Garrison Captain?” she suggested.
“Well, he was on a cot, so...” I stood up, taking her hand, and led her out of the game room and into the living room across the hall. I heard some movement behind us, but then Elyse moaned again so Rhia must have gotten back to her fun.
I went to the couch and laid down on it. “Better?” I asked.
Tori gave me a considering look for a moment and then a little smirk. “I’m pretty sure you said that Captain was jerking off,” she said. “I think I need the visual.”
I snorted and chuckled, quickly undoing my belt and shimmying my pants down around my thighs. Between the sights and sounds of the lesbian action, and gorgeous Tori standing over me completely topless, I was already mostly hard and as I wrapped my hand around my cock it stiffened.
“How’s this?” I asked.
She sighed, snickering a little, and licked her lips. “You know you’re hot, right?”
That had me letting out a huff of a laugh. “I guess so?” I hedged. “I don’t really think about it like that.”
“Well, you are,” she said. “I’m not, like, ‘OMG I want an older guy’ like Elyse, but you are objectively hot.”
“Says the absolutely stunning college actress,” I said. “But how about we save the personal pump-up affections for later? Because I think your Garrison Captain had just realised that the Fucking option was probably in his best interest as he stares up at the ridiculously fit, super-attractive hare-person with her perfect tits hanging over him as she undid the laces of her pants.”
“They aren’t perfect,” Tori smirked a little.
“Subjectively, my dear, I disagree,” I said.
“And Jade’s tits are covered in a downy soft thin layer of fur since she’s a hare-person. Or should I say, my tits are like that,” Tori grinned a little, running her hands down from her chest and over her breasts, letting her fingers play around her pretty, dark nipples. For all that had already happened between us, I hadn’t had a chance to really give those perfect breasts of hers the attention they deserved.
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