DM and the Dirty 20s Ch 68-70

This is the first 5k in a 10k sponsored stretch of this story. I decided to release it in two sections because I'm not entirely sure if I like how I handled this first section of Ch 68. Let me know if you think it works, or if I should rework it. Cheers!

Chapter 68

The three intrepid adventurers marched out of the mouth of the tomb, blinking against the light of the sun as they ducked under the jaw of the ancient giant’s skull. Young Timmy Nettles had spent the afternoon chewing on long pieces of grass nervously as he lingered higher up on the hill, and when he heard the sound of movement down below him, he tensed, grabbing for the pile of fist-sized rocks he’d collected as a just-in-case pile of ammunition.

He’d heard some horrible sounds echoing out of the mouth of the skull and the tunnels beyond. And then there had been the occasional rumble of the wildlife in the area. He was even half-sure he’d seen a dragon fly by, far overhead. It might have been a vulture, but he was pretty sure it had been a dragon.

The three women who he had led to the ancient tomb looked awfully different when they came out again.

Olivia of Parnasus was gleaming in silver and yellow, wearing a brand new breastplate and helm. The bare steel of the armour was polished to a light-catching sheen, but most of the armour was painted in a bright, daisy yellow that would stand out on any battlefield. Shockingly, while the helmet was fairly consistent with the Imperial Gallic styles of the old Southern Kingdoms bordering the deserts beyond, with a short brim to protect the forehead from a direct swing and cheek plates to protect the face, along with a red and yellow crest of horse hair running along the top, the breastplate seemed to have been made for her. It hugged her long torso and curves perfectly, and just like a show fighter whose armour might be formed into the shape of an ideal muscled torso, this breastplate was shaped in the form of a woman of immense appeal, but also strength. Breasts, complete with small silver nipples, sat above a row of armour abs, and even the back was like looking at the graceful, lithe back of a nude beauty. She was entirely covered from hip to neck, and yet somehow it felt like spying on her bathing in the river just to behold Olivia striding forward confidently in that armour.

Next came Jade Highkick, tall ears twitching as she took in the surroundings around the hill. She was still comfortably clothed in the travelling clothes she had marched the King’s Road a week ago, looking a little worse for wear after their journeys through the deep forests, but slung upon her back was a rainbow coloured bag that seemed to weigh almost nothing, and looked almost full to bursting at the same time. The flap and mouth of the bag seemed to almost be a face, smiling at all who beheld it. In counterpoint to that pleasant, almost jolly, addition to the hare-woman’s equipment was the thin, spiked chain draped like a belt around her waist. The sheen of it was strangely mottled, as if it were some oil-slick alloy of a dozen metals, and each contending with each other to seem like the true core of the chain. Strangest of all, at each end of the long chain, was a heavy metal ball about the size of a fist, each featuring a carved, monstrous face with fangs that looked ready to animate, bite and swallow anything they stuck.

Last, but certainly not least, came Renee de l’Ombres, and for a moment, Timmy Nettles thought that the sorceress had undergone some horrible corruption, deep in the ancient tomb. She was all shadows and darkness, hovering like a haunting ghost behind her two friends, her face a ghastly, pale vision that could only belong to the dead. But as she stood upright, the sorceress cast back the hood of her new cloak, revealing that her beauty remained unmarred beneath the long head covering, and that the unnatural swirling of the thin, dark cloak, even without a touch of breeze in the clearing, was what made her seem to be floating. That cloak was not her only prize, however, as she also now wore a large amulet in the middle of her chest, sitting in the open space between the embroidered breasts of her robe. It was a large black pearl, almost the size of a dagger pommel, set in a heavy silver circlet etched with ancient runes. Under the light of the sun, the dark pearl gleamed like it was trying to soak up those rays.

“In any other game, I’d complain about Titty Armour,” Rhia snorted, smirking once I was done describing the three of them in their new looted gear. “But I guess it makes sense for your world.”

“Totally impractical," Tori agreed. “And plenty of people have proven it online. But it still sounds hot.”

“Can I try and pinch the nipple of the armour and see if she feels it?” Elyse giggled, shooting an evil grin across the table at Rhia.

“Don’t you dare,” Rhia laughed, glaring at me instead of Elyse, knowing that I would think that sounded like a great idea. “It’s magic armour, it’s supposed to protect me, not make me more vulnerable.”

“Unfortunately, the nipples on Olivia’s armour are not attuned to her nipples,” I chuckled to Elyse.

“Lame,” the blond laughed.

The process of handing out the first real loot for relatively fresh characters was always fun, particularly when I didn’t have a player who was trying to powergame and just wanted More Stats. I couldn’t fault anyone for chasing that - the game was kind of designed around trying to maximise statistical thresholds when you got down into the nitty-gritty. It just wasn’t as fun.

Olivia’s armour, when Renee had pulled it out of the Bag of Holding, had been in the shape of a male torso, but as with all magical items in my setting, it adapted to the wearer. Rings changed size to fit fat or skinny fingers, boots magically stretched to fit comfortably on the largest or smallest feet, and in this case, magic armour would always seem to be made for a wearer capable of wearing it. The swap of decorative genders was also something that had come up plenty of times in past games, though I wasn’t surprised that details like that hadn’t made it to Rhia through Mel or Dan, considering it was almost always a sexual joke.

The armour had been the set that the Steel Prince had used on campaign as a mercenary captain, and beyond being a proper breastplate, and therefore an upgrade for Olivia right there, I also gave it the minor abilities for the wearer to remain comfortable in extreme temperatures (since he’d been campaigning across deserts), and to self-clean. More pertinent, I also gave it the ability to, once per day, flash like a bright strobe light for three combat rounds, forcing all enemies within twenty feet to make saves against being blinded or dazzled.

Building an item for Jade had been the hardest, mostly because I wanted it to feel original for me, even if Tori wasn’t as heavily steeped in the game or the Monk class. Handwraps, boots, or a staff were all overdone. I also needed to give her a way to actually fight their Werewolf enemy without just trying to slug it out, but Tori hadn’t shown any inclination to Jade picking up a bow. I’d landed on a modified Meteor Hammer, which would let her get creative. I’d also kept back a couple of secrets about that particular weapon, and I already had a feeling that Tori was suspicious of the fact that she’d received a much larger slip of paper than the text on it required.

Lore-wise, the girls didn’t know what the connection between the Meteor Hammer and Hastor Ungor had been, but my current head-cannon was that he used it less for the properties it had as a weapon and more for the fact that Jade could throw it like a bolas, and it would attempt to magically grapple an opponent. It was always useful to leave gaps in the backstory of things; I could go back and change things to make them more suitable to future events, and help make either the item, or Jade as its wielder, more pertinent. 

Renee had ended up with two items, though I hadn’t known if the girls would realise the cloth draping the entrance to Hastor’s tomb would be a magic item. Hell, I wasn’t even sure they would get the whole lore drop about the Steel Prince and the Order of Enigma, or if they’d just fight the sphinx. The cloak was a modified Cloak of Displacement and was Elyse’s reward for being the player to not only take the risk to walk boldly across the room, but also identify that it was magic and worth grabbing. I’d already decided that it would be ‘extra spooky’ before I knew who would get it, and Renee being able to go ‘ghost mode’ and look like a floating spectre when she raised the hood had thankfully matched Elyse’s vibe for her character. Her other looted item was a lot more specific to her, and a little more generic, but was one of those ‘really helps the character work in a campaign that isn’t just one fight a day.’ It was a modified Pearl of Power that she could activate in a ritual once per day to gain back some used spell slots. Of course, there was a blank spot on that particular item slip as well, and I had some ideas for why.

The Steel Prince hadn’t used magic, so why had he been carrying it around?

I was looking forward to when one of them realised they should probably be asking questions like that.

“Did- Did you find the bottom?” Timmy Nettles asked the three adventurers, stammering a little at the vision of the three women, but also clearly wondering if maybe there were any further treasures down in that cave.

“We did, young man, along with the guardian of the tomb,” Olivia said.

“If you’re thinking of going down there, just know that there’s a bunch of angry ghosts,” Renee said. “Angry ghosts.”

“Oh,” Timmy mumbled, looking a little crestfallen. “Alright. I don’t want to mess with no ghosts, I guess.”

“To be fair, we’re about to hike back to a castle that’s about to be under siege by an army of bandits,” Jade pointed out. “Ghosts might be preferable if you can make friends with them. You could live out here in the woods, just you and the ghosts, make a new life for yourself.”

“I’m, um, I’m good,” Timmy said.

“Speaking of the impending siege, we are still on a clock,” Olivia said. “Timmy, bring us back to the castle. We’ve got a Princess to save.”

- - - - -

“Shitfuckballs,” Olivia murmured.

“This is not good,” Jade agreed. “This is really not good.”

“Timmy,” Renee said. “Do you have any family living somewhere close by that you can go shelter with?”

“No, miss,” Timmy said, slightly horrified as he joined the three adventurers peeking over the edge of the hill.

Campfires were dotting the clearing around the castle in the evening light, lining most of the forest line. The bandits had encircled the castle. In the fading light of sunset, they could see bodies scattered and arrows peppering the dirt road and field up to the main gate, large scorch marks marring the gates themselves, and a very new and strange pile of vegetation at the base of the west walls, with more bodies there as well.

They were too late. The siege had begun.

- - - - -

“Could we have gotten back in time?” Elyse asked, covering her mouth with one hand as she mumbled around her lasagna. The reveal at the end of the session that their adventure out to the Tomb had meant they missed the first attack on the castle had led to quite a lot of cursing and frustration from the girls, but they’d packed up their stuff with only mild complaints that we could keep playing, and then they’d all headed to the kitchen to start heating up the dinner Elyse and Tori had brought with them.

When I’d finished cleaning up my more extensive amount of stuff, I was a little surprised but in no way shocked when I found the three college coeds had stripped out of their costumes and were flouncing around in just their panties. Really, I was almost surprised that panties had made the cut, even if they were all deliciously small little things that were more teases than they were garments.

The resulting grabass (and grabtits, which really should be a word) as I’d helped set the table had been fun. I’d also gone outside to make sure the hot tub would be ready, and Tori had followed me boldly, slipping into my arms and making out with me for a long moment in our moment of privacy before we went back inside, my cock now firmly tenting my pants. That, of course, had led to the girls demanding I strip back down to my own underwear for dinner, and they’d all gotten a good, smirking look at my bulge before we sat down.

“Elyse, hon, I’m not gonna tell you that,” I chuckled.

“Can I bribe you with a blowjob?” she asked with a playful smile.

“No,” I laughed.

“We can’t bribe him with sexual favours because he knows we’re gonna give it up anyway,” Rhia snorted. “It’s a big Catch 22.”

“How about we just don’t try to bribe the dungeon master?” Tori suggested. “I’m just as annoyed as you two, but you gotta admit that was like the dramatic ending of a really good TV show.”

“Just to be clear, you can always try to bribe me,” I grinned. “I’m just not promising it’ll work.”

The rest of dinner was mostly the girls speculating on what they were going to do about the siege. They had a lot of interesting ideas, and there was a part of me that dreaded some of the more creative ones since they were likely to fail spectacularly. That was the life of a DM, though - trying to give the Players enough leash to get themselves into deeper trouble while answering questions, but not quite enough to just run off a cliff.

Once we’d finished eating, they once again wouldn’t let me help with the dishes and did their little Trading Places game as, one after the other, they sat on my lap and made out with me while the other two cleaned up. I was allowed to let my hands wander, and all three of them ended up with their butts roughly massaged, their backs softly clawed, and their tits mauled. Apparently, there was an agreement that I wasn’t allowed to put my lips anywhere other than on their, however, which felt like a waste considering the six nipples in the room that were just begging for some sucking and nibbling.

Then we were outside, heading into the hot tub, and the tiny panties came off, and my cock was allowed to spring free after being tortured by the dry humping of the three of them as we made out.

“I have an idea,” Rhia declared once we’d all settled in under the deliciously hot water. Her tits were bobbing right at the water line, looking particularly wonderful in the lighting.

“Is it another triple blowjob moment for Shane?” Elyse asked with a grin. “Because that was fun.”

“No, I think we need to get back at him,” Rhia said, smiling and sticking her tongue out at me playfully. “For the cliffhanger, even if it was a good one.”

“I don’t think it was technically a cliff hanger,” Tori said. “It was just dramatic tension. None of us were in immediate danger, and the very next thing that happens decides if we survive or fall.”

“Whatever,” Rhia waved off the semantics. “I still want revenge on our evil mastermind of a Dungeon Master, OK? We’ve all paired off now, so I say that the three of us girls have fun and Shane only gets to watch.”

“You’re such a lesbo now,” Elyse laughed.

“Shane’s cock would beg to differ, but I’m not gonna lie that I want my tongue up your little snatch again,” Rhia countered with a lustful grin at her friend.

“Do I get a vote in this?” I asked.

“Well, that answers it for me,” Tori grinned, her eyes alight at the playful game. “Bring those tits over here, Rhia. Elyse, sit up on the edge of the hot tub so Rhia can get at your pretty little pussy without drowning.”

“You think my pussy is pretty?” Elyse giggled, already pushing herself up out of the water, her lithe body looking so good shimmering with wetness.

I groaned softly as all three of them shot sly looks over in my direction. They knew I couldn’t be bribed, now I had to hope that they didn’t decide torturing me with wickedly hot lesbian threesomes wasn’t a recurring game after the game.

Then again, watching three beautiful women make love in my hot tub wasn’t exactly punishment, was it?

Chapter 69

“No one slept over, huh?” Melissa asked me as she poured herself a cup of coffee, then came to sit down with me at the kitchen table. “I figured that would be a regular thing now, coming over to find one of them prancing around half naked.”

“Looking forward to it?” I asked with a little smirk.

“Maybe a little,” she laughed, then took her first sip of her drink. “Seriously, though. I was a little surprised when Rhia came home last night.”

“I’m not a machine, Mel,” I said. “She made her point yesterday afternoon, and then we played a long session. Then the girls decided to put on a show for me out in the hot tub.”

Mel snorted, shaking her head. “Oh, to be young again,” she mused.

“Oh, please,” I scoffed. “They’re amazing, but you, Val and Rachel could probably put on an even more impressive show.”

“Why thank you,” my friend grinned like a pleased cat, then took another sip of coffee. Then she set her mug down and sighed. “So you fucked my daughter.”

I’d known it was coming, but it still made my spit catch in my throat for a moment, and I had to clear it with a grumble, which just made Mel smirk again.

“Any change of heart?” I asked her, avoiding a direct answer.

“No,” she said, shaking her head. “I mean, it’s still a little weird, right? Is it weird for you?”

“A little,” I shrugged. “But… she’s a different person now, I guess. There’s a big separation in my mind of little Rhiannon running around in the backyard, leading the other kids around during a BBQ, and Rhia now. Maybe it helps that she was so busy for the last year or two, and I didn’t see her much.”

“That makes sense,” Mel said. “We had to have a whole ‘I’m an Adult now’ conversation when she started college, and we changed the house rules. That and then all of this has really made her feel like a different person for me. Still my kid, but not my little girl anymore.”

We both took a long sip of our coffee, letting the silence linger.

“Did she hold up to the family reputation?” Mel asked after a minute, smirking at me over the rim of her mug.

That made me snort and shake my head. “I had to pump the brakes on unprepared anal, so I’d say so.”

“Oi vey,” Mel laughed. “OK, I’ll put together a kit if she’s interested in you plundering that skinny little ass of hers.” Then she snorted, smirking and shaking her head. “Now that’s kinda weird. Taking the anal virginity of a mother and daughter, twenty years apart?”

“Mel,” I said. “You’re not helping with the weirdness.”

That made her laugh again, her eyes alight with her teasing nature, and she hummed a soft tone as her laughter died off.

Then she stood up, and I figured she was going to go get more coffee, but she confused me when she came around the table to me and gestured for me to turn to face her in my seat. Then she sat down, straddling my lap and looking at me face-to-face, our noses an inch from each other and her bust pressing against my chest through our clothes. My hands naturally went to her hips, holding her intimately. It was a position we’d been in plenty of times before, though rarely clothed. Hell, rarely without my cock penetrating her.

I could see things she wanted to say running around in her mind behind her eyes, and I waited for her to decide which one to say. She surprised me again by not saying anything at all - instead, she kissed me. Not a friendly peck, like I often got from her, Ronnie and Rachel. Not a deep, lust-filled soul kiss like we would share in the middle of sex during The Game, either. It was a firm kiss of controlled passion, love, and intimacy. No tongue, but still moving and growing.

It was a kind of kiss we’d hadn’t ever shared while clothed, or outside of Game Night.

I wasn’t sure what to do with that.

“Mel,” I murmured when she pulled away, but she stopped me cold by covering my lips with one hand as she looked at me seriously.

Then she slipped off my lap, going to her knees on the floor, and wrapped her fingers into the waistband of my morning sweatpants and started to pull them down my hips.

“Mel,” I said again, entirely meaning to stop her, but countering that firmness by lifting my ass a little from the kitchen chair so she could keep pulling my pants down. My cock, already half-hard after that kiss, bounced into the air lightly since I’d been going commando.

“Shane,” she said in a challenge, grabbing my cock comfortably and starting to stroke me.

“It’s not- What about Dan?” I asked. “We can’t do this to Dan.”

“Shane,” she sighed, her challenge softening, and she stood back up without letting go of my cock, kissing me the same way she had before. By the time she pulled away again, I was fully hard in her hand. She went back to her knees, leaned forward and gave the side of my cock a long, spitty lick that was both meant to get me slick for her stroking and to provide a lewd little show for me. She started to jerk me off a little faster. “Dan’s been laughing his ass off for years that we don’t fool around, Shane,” she told me. “He’s told me dozens of times that he doesn’t mind if we do. Not in a ‘he wants to know’ cuckold way, he just knows how close we are, and that sex in our group of friends is different. I didn’t get your cock during The Game last time because you were busy being a tentacle monster for Rachel, and now you’re fucking Rhia and her friends outside of their game and I’m hearing all about it. So why shouldn’t I get to suck my best friend’s cock over our morning coffee? Or sit on it and spin when we grab lunch?”

“I- It’s-” I stammered. Twenty years of tradition was stuck in my throat. Twenty years of carefully maintaining boundaries for In Game and Out of Game to make sure everyone felt respected and safe.

“I want to suck your cock, Shane,” Mel said. “Not a baron, or a vampire, or a whole tribe of orcs. I, me, Melissa, want to suck your cock. So I’m going to do it.”

And she did.

It really wasn’t fair to compare, but Mel could compete with Rhia, Elyse and Tori doing a triple blowjob and still come out on top. Twenty years of history between us, of knowing each other’s buttons, of practice.

Melissa sucked my cock in the middle of my kitchen at 9:38 AM. No dice, no characters, no game. Her lips were heaven on my shaft, her tongue a tempting devil on the ridge of my head. She knew just when to pull away, gasping for breath as spittle strung between us, and just the right firmness to squeeze and stroke.

Her eyes were lust and love. For me.

This was changing everything, but… was it changing anything?

I gathered up her thick, wavy hair, and she grinned at me around my cock, looking up into my eyes as I held it in my fist at the back of her head. Then I stood up, and she shuffled with me so she could remain upright instead of leaning back, and I took over, fucking my best friend’s mouth just the way we both liked.

“Fuck, Melissa,” I grunted. Not Meliana, or Annabella, or any of her other characters. “God, Melissa.”

She grabbed my ass with one hand, and after twenty years, I knew what she was signalling she was ready for. I slowed the pace of my soft thrusts into her mouth but started pushing deeper, and in one smooth motion, I pushed deep, and she swallowed my cock into her throat, her nose pushing into my pubic mound as she took every inch of me.

“Mel,” I moaned.

She moaned well, resonant and full from her chest.

She squeezed her fingernails against my ass cheek, and I pulled back to let her breathe. One little look from her told me she was ready again, and I pushed right back into her throat. Another hold, feeling her swallowing around the head of my cock. Eventually another silent squeeze, another chance to breathe, and she pulled all the way off, drool and spittle leaking down her chin.

“Come down my throat, Shane,” she murmured. “Fuck my throat and pump your cum right into my stomach.”

“Jesus, Mel,” I murmured with a soft chuckle.

She smirked at me and went to say something, but I got the drop on her this time and pushed my cock back into her mouth.

When I came, I was left light-headed and had to sit back against the edge of the kitchen table as Mel panted to catch her breath, grinning even as she used the napkins I passed her to wipe under her eyes, all over her chin and down her neck.

“OK,” she said, licking her lips as she looked me up and down, still on her knees. “That is definitely a new part of our morning coffees. Especially if you keep giving me loads like that. God, I feel like I ate a full breakfast.”

“Mel,” I said, my brain finally not feeling like it was spinning slowly in my skull.

“Mhmm?” she asked, giving me another of those Cheshire cat grins. She took my hands and let me pull her to her feet, and I wrapped my arms around her and kissed her hard. More than before. Lustful, passionate. Tongue. She moaned into the kiss, her body melting against mine as we made out in my kitchen. She took my head in her hands, keeping me locked in, and my hands wandered down to grab her ass through her shorts. I grunted softly when she moaned again, even hornier than before.

Then I picked Mel up by her ass and turned, sitting her down on the edge of the kitchen table, and pulled away from the kiss. She looked at me, hungry and hopeful.

“One good oral orgasm calls for another,” I told her with a little smirk, and gave her a shorter, comfortable kiss before dropping to my knees.

“You always were my favourite pussy eater,” she grinned as she helped me start pulling her shorts off her. “Just the right amount of everything.”

“Then I’m going to spoil you rotten, Mel,” I promised her as I tossed her shorts and thong to the side and spread her legs, licking my lips at the sight of her horny pussy.

“Please, Shane,” Mel said with a huge grin, lifting one leg to put it over my shoulder. “Spoil me as much as you want.”

There was a part of me that wanted to just dive in, drill my tongue into her and start slurping away. That was one way to get her off, and it could be a lot of fun.

But we had fun. And we were alone. I could take all the time in the world, and no one would be getting impatient for the DM's attention.

I kissed the inside of her knee, and Mel’s eyes went wide, realising that I was going to draw this out. No fast orgasms for her - we were going big.

Chapter 70

“Are we actually playing, or can we just go upstairs and fuck?” Elyse asked once we’d said our hellos and kissed. She’d brought her D&D bag, along with an overnight bag, and had dropped them both just inside the door so that she could leap up and wrap her legs around my waist.

I was holding her up with both hands on her butt, massaging her cheeks through the skimpy little shorts she was wearing, and chuckled at the faux-innocent look she was giving me after a question like that. “That depends,” I told her. “I’d be more than happy to fuck you over and over, baby, but then you’d have to explain to the others why you didn’t get the Hastor lore from your solo session.”

She screwed up her face a little, and I fell a little more in love with her. Elyse’s quirkily pretty looks and her mildly Alt style, how different she was from my other lovers physically, and ultimately her playful, energetic personality, all kept building my heavy attraction to her.

Elyse came to a decision. “Fine, we’ll play,” she said. “Since I know I can’t just get it out of you as pillow talk after you rail me into a coma. But, I need you to say that again.”

“Say what again?” I asked, then quickly realised what she meant. “Oh. Would you like me to carry you upstairs and absolutely devour that delicious pussy of yours, baby, or do you want to find out what Renee de l’Ombres learned in the Tomb of the Steel Prince?”

“Mmm, I’m your baby,” she hummed happily, pressing her lips to mine in a firm kiss. Then she pulled back, looking all over my face. “God, having an older guy call me should not turn me on this much. I should really get a therapist or something to figure that shit out.”

“Do you wanna stop?” I asked with a wry smirk.

“No. Fucking. Way,” she grinned, then kissed me again.

(To Be Continued)