Dungeon Mistress
Copyright© 2025 by JayFriday
Session 1
Erotica Sex Story: Session 1 - Chris had to take some time off from running the usual D&D game for his childhood friends, and they found a hot new DM: Monica. And she runs a very sexually charged game, with some very seductive villains and NPCs. Before long, Chris and his childhood friends are all getting pulled in to Monica's schemes, and the line between players and characters is so blurry...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Ma Fa Mult Coercion Consensual Reluctant Romantic Lesbian BiSexual Heterosexual Fiction High Fantasy DomSub FemaleDom Humiliation Group Sex Cream Pie Exhibitionism Facial Masturbation Oral Sex Sex Toys Tit-Fucking Voyeurism Big Breasts Size
Mike’s new place was awesome, and his combination housewarming/holiday party was buzzing with friends and conversation. I looked around the place, thinking fondly about how grown up we all were now: this was a housewarming party. Because now he owned a house. A pretty far cry from gathering in his parent’s basement to play Halo on that shitty couch until 4AM.
Mike spotted me, came over, and half-steered, half-dragged me over to a young woman who was standing near his fireplace, by herself, sipping on wine as she looked at the fire.
“Chris, Monica wanted to meet you. She’s the one I’ve been telling you about. I met her through that board game club I’ve been going to, but she’s been running the usual D&D game for us since you had to stop. It’s been super fun.”
He opened his mouth to say something else, but his doorbell rang. “Ah, shit. I’ve gotta get that. Monica, this is Chris, who used to run games for us during high school and college. Chris, this is Monica, the new DM! You guys can compare notes!”
Introductions made, Mike left us to answer the door.
I looked at Monica. She was in her late twenties or early thirties, maybe; a bit younger than me. Shorter than me, and she gave off a distinct goth vibe. Long, jet black hair. Full dark eyes, cat eye makeup that made them look even larger. Pale skin. A dark lipstick – a deep crimson, almost maroon. She was wearing a black sweater dress that clung to a curvaceous, shapely body.
Damn. She was hot. I wondered if Mike had introduced us because she was single. It was possible – he wasn’t much of a matchmaker, but maybe. I kind of hoped so.
Monica arched an eyebrow. “Hi there, Chris.”
I flushed. She must’ve seen me staring. I pulled my eyes back up to her face. “Hi, Monica. It’s nice to meet you. So you’re the Dungeon Master that Mike’s been raving about, huh?”
Monica gave me a wry smile. “I prefer Dungeon Mistress. But yeah, that’s me.” Dark lips sipped from her wine glass.
I laughed at the joke. “Very cool. I’ve been running games off and on for Mike, Liz, and Erin for years. Just been busy lately.” I beamed at her.
My friends had raved about her DMing abilities. Said she ran an awesome campaign. Tough, but fair, super interesting, great combat encounters, memorable NPCs.
She even apparently dressed up as the characters sometimes. The idea of her in cosplay, I had to admit, was especially intriguing, based on what she looked like in this sweater dress. I tried not to let my imagination wander.
She had let the silence stretch, but eventually spoke. “Yeah, they talk about your old campaigns sometimes. Sounds like you run a fun game.” Her smile was friendly enough, I thought. But a little... aloof. Distant. A challenging edge to it? A little unimpressed, maybe? Hard to say.
She held my gaze. “I’ve actually been thinking that it might be nice to add one more for the campaign. They were all talking about how it’d be fun for you to play in a game instead of running one. If you’re interested and have a little more time in the new year, that is. I know not every DM likes to be a player, though; you might not like my game. I mean, I don’t really like to play in other people’s games; I like to be in control too much. So I get it if you don’t...”
But I didn’t need the easy excuse she was offering. “I would love to. I don’t have the time to run anything but I’ve been dying to get back to playing D&D. It’ll be nice to have someone else do the hard work – and nice to play in the game they’re all raving about!”
She gave me a small smile. “Great. Give me your email and phone number, so I can send you the backstory stuff and some character generation info. That way you can show up and we can get you right in the middle of the action...”
The backstory she sent along packed a lot into a relatively brief document. I was impressed. It was a classic, high-fantasy world; a lot of political intrigue. The party had been on a trip to the court of the Night Queen, ostensibly as emissaries, but with the real mission of stealing an important artifact from her treasure room. Unfortunately, their purpose had been discovered at the end of last session, and they’d all been thrown into the Night Queen’s dungeon.
Monica’s email gave me a clear new character prompt:
You’ll be playing a fellow prisoner, someone who was already there when the party was captured. You’re a servant of the Night Queen who has fallen out of favor for refusing to undertake an important mission because it violated your morals. She left you to rot in this prison a few weeks ago, and it has soured you against her; the party seems like they could be valuable allies, your ticket out of here. And helping them is sure to piss the Night Queen off. You’ve been working on an escape plan, but you know you’re about to be brought in for another interrogation session. That’s where this game session will start.
I made a character within the parameters she laid out. I texted Mike and it sounded like the group was missing a frontline fighter-type, and someone who was a smooth talker, so a paladin was the natural choice.
I settled on the name Cedwin, and emailed her the completed character sheet along with some notes about his appearance and backstory. She replied almost immediately:
Awesome choices, great character. Here’s the details of the plan you’ve been working on. If you can get through the interrogation without giving anything anyway, the party ought to be able to help you escape.
The broad strokes of the plan were pretty straightforward; I had, over the weeks of imprisonment in the Night Queen’s dungeons, gotten the sympathy of a guard, who would be willing to help me escape. The only reason I hadn’t escaped yet was because I couldn’t overpower the half-dozen other guards by myself ... but the arrival of the adventurers shifted the odds; if we all worked together, we could escape. And then plot our revenge on the Night Queen.
It was a good premise for having my character join the group. I was looking forward to game night.
Game night rolled around a few weeks later. It was at Monica’s place; a Friday night. I pulled up the email, plugged her address in on my phone, and showed up a few minutes early.
She opened the door. “Hi, Chris. Come on in.”
I didn’t immediately respond. She was wearing – well, I didn’t know which character she was done up as, but it was clearly fantasy makeup. Her eye makeup and lipstick were an azure blue, with pale gold highlights that only made it all the more striking. Her dark hair was done in some complicated braids, and pointy elf ears peeked out.
Her outfit was ... well, a cloak of deep midnight. There was a clasp at her neck – silver, a stylized full moon – and the cloak was hooded, and draped completely across her shoulders and down her front. It covered her head to toe.
I realized that I was staring, openmouthed. She looked like ... well, some kind of fantasy elf priestess. “H-hi, Monica! Great outfit!”
She gave me a cheeky grin. “You’re the first here. The Night Queen welcomes you to her court, Cedwin. What’ll you have to drink?” She ushered me inside.
My friends arrived shortly after I did. Liz was next, showing up five minutes later, just as I took the first sip of an excellent bourbon Monica had poured.
For years, I had been surprised when other guys told me Liz was hot, or asked me if I thought she’d go out with them. To me, Liz was always the nerdy, slightly bookish girl who lived next door. The one who beat all the optional bosses in Final Fantasy 7 before I did, who got excited when I loaned her Game of Thrones, and loaned me Wheel of Time in return.
But even I could admit that in-her-30s Liz was pretty hot. Nerdy glasses and an obsession with fantasy and sci-fi novels had matured into a hot-librarian aesthetic to accompany her professional-librarian job. Fashionable glasses framed big brown eyes. Long brown tresses spilled down around the glasses. She was dressed in a blouse and skirt.
“Hi Chris! Oh my god, you’re going to get to actually play for a change!” She gave me a warm hug. She eyed Monica’s get-up. “Wow, you pulled out all the stops this week, huh? Damn. Sorry, I came from work ... I’ll bring my Lucia get-up again next session, though.”
“Yeah, I wanted to make sure I set the right tone for the campaign for Chris,” Monica said, her eyes twinkling. “I told you guys, dressing up is optional for you all though. No pressure.”
“Well, in spite of my attire, Lucia the rogue is here and ready to make some mischief!” Liz rubbed her hands together, sitting down next to me. “Lucia the rogue also needs her gin and tonic, please.”
“Difficult to make mischief from inside a prison cell, Lucia.” Monica smiled and began making a drink.
Erin was late. But Erin was always late.
“Chris! Eeeeee! You’re really here!” she shrieked when she saw me sitting at the table, character sheet in front of me. She ran over and gave me a hug.
In contrast to Liz, nobody – least of all me – was surprised when Erin got described as hot. Tall, with long red hair and green eyes, and pale freckled skin, she had classic Irish good looks and a body to match. She had run for class president in high school and won, been president of her sorority in college, and now ran sales or marketing at some giant company.
She wasn’t much of a nerd. It had always been astonishing to me that she’d kept wanting to play D&D with us over the years, but she insisted.
Even more astonishing: she was dressed up tonight. She had on elf ears, a brown robe open in the front, and matching leather armbands and a laced leather bodice. A staff completed the outfit.
She obviously noticed my stare. “Like the outfit? Monica helped me with the ears! My character is Enna, an elvish druid. I’ve got lots of healing spells!”
I smiled. “You look great, Erin.”
If I was honest, I felt a little jealous – she had never dressed up as a character during any of my campaigns. I certainly wasn’t immune to her charms and would’ve loved to see her wearing this sort of thing more regularly.
I had taken my shot with Erin long ago, during high school. And then in college. And then again right after college. But she had always been more interested in swimmers, football players, and fraternity presidents than the data scientist who ran her weekly D&D session. For a long time I had taken it personally, but as we’d both gotten older – and I’d finally had a few girlfriends – that had mellowed into an easier friendship.
Even if I’d still go for it, I acknowledged to myself, eyeing her cleavage in the laced leather of that bodice.
“Enna will take her martini extra dirty tonight, please,” Erin said. She didn’t say it suggestively at all, but Liz snorted anyway.
Monica just put a sly smile on. “That befits tonight, as our game begins in dirty prison cells. Give me three minutes to make that, and then we can started.”
Liz looked surprised. “ ... But Mike isn’t here yet!”
Monica still had the same smile. “Well, you remember how the battle with the Night Queen’s guards left Meldrin grievously injured? His character isn’t exactly conscious, right now. More on that in a moment. I told him he could skip this session since he’s out cold; we’ll get him back in the game when you all get Meldrin some healing.”
I blinked, disappointed. I had been looking forward to playing with him. Just having him not show up seemed extreme. But Erin and Liz nodded, as if it made sense; maybe this was how Monica ran things. So I nodded along, and took another sip of bourbon.
“It has been two full days since the Night Queen threw you all in her dungeon. You have not been mistreated, but you can tell that staying here for too long is a bad idea.”
Monica’s voice was low, intense. She’d lowered the lights in the room a bit before she’d started talking.
“The thin slit-like openings that pass for windows into these dismal cells are paned with some translucent, quartz-like material. During the day, it lets scant amounts of lights through ... but at night, it does something to the moonlight. Something maddening. You can feel it creeping about the edges of your consciousness, like foxes prowling around a henhouse. Wanting to get in. And from the howls and incoherent gibbering coming from the cells down the hall, it’s all too easy to imagine what being here long-term will do to your sanity.”
I had to hand it to her, she did a good job setting the scene. All three of us were quiet, listening.
“Enna can tell that this is having an especially negative effect on Meldrin, your wizardly companion. He has been unconscious since the battle – two guards dumped him into the cell with you two. Something is wrong with his mind. And it’s only getting more wrong, the longer you stay here. He periodically moans or mumbles something in his sleep, but is otherwise completely still.”
Erin frowned. “Can I use one of my spells to heal him? I’ve got a few that...”
But Monica was already shaking her head. “Enna’s connection to nature feels far from her, in this moment. The forests of her home feel so distant; night reigns here, and the moonlight coming in through these windows is not the soft light that plays on dappled meadows, it’s silvery and alien. Perhaps if you get out of the dungeon, you can help him.”
Monica paused, letting that sink in.
“The only other thing of note is the cellmate across the corridor.” A smile played across her lips. “He hasn’t said anything to you yet, but he’s been watching you since you arrived. Chris, want to introduce Cedwin?”
Both Liz and Erin turned to look at me.
“Sure ... Cedwin’s, uh, a half-elf ... he’s looking a bit the worse for wear ... he, uh, has brown eyes...” I struggled to decide what to share. I suddenly felt awkward, on-the-spot.
Monica cut in, smoothly. “The half-elf in the cell across the way is tall, lean. Stripped of his armor and armaments, his chest is bare; he has the sinewed muscles of one accustomed to battle. His face...” she glanced down at some notes behind her screen. “ ... though perhaps usually clean shaven, has a week or two worth of stubble growing into a beard, likely from being confined down here. He’s got a tattoo of a tower – The Tower – on the forearm of his shield arm. His dark eyes are intense. And he’s been staring at you two – and your companion, Meldrin – since you arrived.”
I blinked at Monica. Her description of my character was ... accurate, in the details, but ... well, she made him sound a lot more attractive than I would’ve. She just gave me a smile. “I did read your character description. It was good.”
“Tour character sounds like a hottie,” Erin giggled.
Liz nodded. “Yeah. A capable hottie. With that description, Lucia’s been sizing him up since we arrived also. He might be useful. Lucia waits for a moment when the guards are scarce, and then...”
Liz’s voice shifted slightly lower, huskier. “Hey handsome – yeah, you, in the cell. You want out of here, right? We do too, so stop eyefucking us and let’s work together. Any ideas?”
Erin leaned over to me and whispered, “I love Liz’s Lucia-voice.”
I opened my mouth to have Cedwin reply to Lucia, but Monica cut in again. “The half-elf is clearly about to respond, when you all hear the clatter of boots coming down the hall, and he lapses into silence. Two of the Moonguard come in – you recognize them from the fight earlier, the Night Queen’s personal guards. They open your cell, Cedwin, and muscle you out and up the stairs. The Queen wants a word, one of them sneers at you.”
Then Monica stood up. “We’ll do this next scene in the other room, since it’s just Cedwin. Back to Enna and Lucia in a few!”
Uncertainly, I stood up to follow Monica. Erin gave me a little cheery wave. Liz opened her mouth like she was going to say something, then closed it. I couldn’t read her expression.
I had never done anything like this when I was DM. Being a player – not being in charge of the game – was weird, I reflected, as I followed Monica.
The other room, it turned out, was just Monica’s bedroom. The light was dim – just a single lamp on her bedside table.
“Sorry about the lack of seating. This is just a quick scene anyway. I thought it’d be fun to leave them guessing at what’s happening.” She patted the edge of the bed next to her. I sat, bemused.
“The guards unceremoniously usher you up the stairs, through the throne room and into a room that is familiar to you – the Night Queen’s private chambers. Of course, you’ve mostly been there under more auspicious circumstances. This is likely to be an interrogation. You’ve seen many men go into this room and come out broken. Not necessarily in body – but certainly in spirit. Their minds belong to her.”
She stopped, letting that sink in. “Anything I know to prepare myself for?” I asked.
She cocked her head. “You’ve never been present during one of her interrogations, but you’re aware that it isn’t likely to be physical torture. That’s not really her style.”
I nodded, thoughtful.
“You only have a moment to think about it, though, before you’re hustled into her private audience chamber and dumped at the feet of the Queen herself.”
Monica sat a little straighter, drawing the cloak about her. Her eyes grew ... colder, somehow. Imperious. When her voice came out, it was commanding, now. Commanding and amused. “Cedwin. My most disappointing servant.”
“I, uh, pull myself to my feet slowly, trying to gather my dignity,” I said.
Monica nodded. “You can feel her eyes roving over your body, your bare chest, as you stand.” Her voice went amused, again. “Still sane, I see, in spite of your stay in the Lunar Prison.”
“For now ... your majesty.” I said the words begrudgingly, trying to get into character.
Monica’s eyes sparkled. “Ah, Cedwin. Where did we go wrong? I thought you were a loyal, devoted servant ... that a few weeks in the dungeons might make you appropriately remorseful for your failings ... but now I hear whispers that you’re planning an escape. That just won’t do...”
As she spoke, Monica pushed the cloak back from around her shoulders.
Underneath the cloak, she was wearing a black corset. It was strapless, leaving her shoulders bare and exposed. It pushed her pale, full breasts up and together into a full shelf, creating deep cleavage.
I was completely off-balance, staring at her tits. “I, uh...” Fuck. She was hot.
“The Night Queen leans forward and strokes her hand down Cedwin’s bare chest.” As she spoke, Monica stroked her fingers down my chest. I was wearing a t-shirt, but I could still feel her fingers, sensual, tracing my chest through the fabric.
I could feel my cock getting harder by the second.
“I’ve seen the way you look at me, Cedwin.” Monica’s impression of the Night Queen was suggestive, now. “If you serve me well, you could receive many... rewards.”
My mouth was dry. I swallowed, trying to get it together. Sure, she was hot, but it was just a corset. Erin was wearing something similar. This was just roleplaying in costumes. “Your majesty ... after what you’ve asked me to do, I could never serve you again.” It came out a little weakly, but at least I said something instead of just ogling her big tits.
“Cedwin, Cedwin. You are a strong-willed man. But you must know that even you cannot resist me for long.” Monica leaned in close, whispering the next words in my ear. “Eventually I will break you. Make you mine. Your desire for the pleasures of the night will be too great. You will not just call me Queen again. You will call me Mistress.”
I was rock hard by the time she pulled her mouth away from my ear. I couldn’t take my eyes off her tits.
Monica glanced down at my pants and smiled. “Even now, your body betrays you,” she said, in her amused Night Queen voice.
I blushed, hard. Shit. Monica could tell. I didn’t know what to say. Or think. I had never run a game like this. Never even heard of a game like this. Mistress? Fuck.
“Cedwin, I am returning you to your cell, now. But consider my offer. Rejoin my service and be rewarded.”
Monica shifted back to her normal speaking voice. I watched with a strange mix of disappointment and relief as she adjusted the full cloak to be covering herself once more. “Okay, so the same Moonguards drag you back to your cell. Anything you want to ask about or do before we rejoin the others?”
I opened my mouth. I didn’t know what to say. Tell her to stop? Stop what, though? Apologize for getting hard? She’d seemed to like it, if anything.
Monica was watching me, expectant, maybe a little curious. For all appearances, just a DM waiting to see if her player had a question.
I just shook my head, and she stood up. I followed her back out to the others, trying to adjust myself to make my erection less prominent.
I must’ve had an odd expression on my face. When I sat down in between Liz and Erin, Liz leaned over, and softly said, “Everything ok?”
I forced a smile. “Just, uh, weird to be a player in someone else’s game.”
Liz nodded, satisfied.
“Okay, so the guards bring Cedwin back a few moments later. He looks none the worse for wear, that lean body still unmarred, although those dark, intense eyes look a bit haunted, perhaps, now.” Monica paused for a moment. “Actually, the two of you can give me a Perception check.”
They both rolled. Enna had a terrible Perception modifier. “Six,” Erin reported, crestfallen.
But Lucia was good at spotting small details. “Twenty-three,” Liz said.
“That tattoo on his arm – the one of the Tower – it looks a bit fainter than it did before, you think. Faded.”
Liz and Erin looked at me, curious. I tried to play it off. “Hey, don’t look at me, I only learned what the Tower is, like, a week ago.”
Liz shrugged and started asking questions about the cell bars, the locks, that sort of thing. But I thought I knew what the significance of the tattoo was.
Paladins like Cedwin needed to pick a god to worship. Looking through the backstory document, the gods for the setting were different than I expected. Instead of a typical pantheon of deities, there were five Doctrines, which represented the foundational forces of the universe.
I had picked The Tower. It represented order and discipline, the lighthouse pointing the way to civilization amidst the wilds of the crashing ocean, man’s knowledge, triumph and resistance over the chaos of the natural world.
That tattoo was a physical representation of my character’s principles – and Monica was saying they had been eroded by that encounter. Because I’d gotten hard? My face heated a little at the thought. That didn’t seem fair.
“Hey, handsome in the other cell.” It was Liz, using her husky Lucia voice. “Any thoughts on how we might get out of here?”
It snapped my attention back to the game. I glanced over at Liz, who was grinning at me. The banter was a little different, but this at least felt familiar. Just me and my childhood friend, roleplaying. I grinned back, feeling more like myself.
“I’ve got a name, you know.” I tried for a baritone, full of weariness. “Cedwin.” I glanced left and right, as if ensuring the guards were distant. “And yes, I’ve got some thoughts.”
“Do tell,” Liz purred.
“One of the guards is a friend; if we can–”
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