Dungeon Mistress: Session 2

Authors Note: Well, I hadn't initially imagined this as a series, but I had enough fun writing the first part - and it spurred enough additional ideas - that I'm fleshing this out further. My initial plan is a five-session mini-campaign. Here's Session 2. :)

Thanks for this and any other feedback, and enjoy!

---

I stared at the email in my inbox for a long, long time.

---

Subj: Next session

Greetings, intrepid heroes! I had a great time in our very first session with Cedwin!

A few notes for next session:

●

After your daring escape, we're going to pick up the action a week or so later. We'll recap the week -- so if there are things you've been doing as you travel away from the Night Queen's court, you can talk about them.

● Our next session will begin as the party arrives in the port city of Ravensgate. Situated right on the border of the Night Queen's realm, this city is far from -- though not completely out of -- her reach. It seems as good a place as any to lick your wounds, marshal some allies, and plan next steps.

● Meldrin is still unconscious, so: sorry, Mike, but you can skip this one again. The party should have an opportunity to heal you this session. If they pursue it. It's up to them!

● Everyone else: PLEASE BRING YOUR COSTUMES. I've got a few scenes in mind that I think will be more fun if we're all dressed up.

● Chris, I'm taking pity on you since you're new. I've got a few things you can wear. Show up a few minutes early, and I'll help you get in wardrobe.

Your Dungeon Mistress,

Monica

---

It was similar to the kind of email I would've sent to all my players between sessions, making it clear where we'd pick the action up.

Except that it disinvited Mike from playing again.

And that it told Liz and Erin to

bring their costumes

.

And that it said that Monica was

picking out some things for me to wear.

How was I supposed to respond to that, after how the first session had gone?

Hey thanks, want me to bring any snacks?

I watched the email thread as replies trickled in.

First Mike responded, bemoaning that he couldn't join for the second session in a row, and telling us we had to make sure to get Meldrin healed this session because he wanted to get back to playing.

Then Liz responded, saying she was sorry she hadn't brought Lucia's costume last time but that she'd be sure to bring it.

And Erin responded saying she was going to try a new costume, which she said was her druid's 'city wear'. And that she'd bring brownies.

And then, after all of that, Monica sent another email, five minutes later.

Addressed only to me, this time.

I stared at the subject line for a beat, and then, heart beating rapidly, I opened it.

---

Subj: Size

Hi. What size are you? It looked like a small or maybe a medium to me?

Your Dungeon Mistress,

Monica

---

I blinked and my face heated as I re-read it.

She was probably talking about clothing. Probably.

But I was well over six feet tall. Lanky, yes, but a

small

?

Or, of course...she might not be talking about

t-shirt

size at all.

It's plenty big,

I thought, feeling a sense of embarrassment. Nobody had ever complained. I had gotten a few compliments over the years, even.

Thinking about my size inevitably led me to the memory of her engulfing my length in her tits. The way my cock had disappeared entirely, vanishing into that deep, pale cleavage. She had really big tits, though; just because she'd made my cock disappear between them didn't mean I was...

I had gotten hard thinking about it, I realized.

Again

.

I went to jerk off.

Again

.

Those moments in her bedroom hadn't just gotten added to my spank bank, they were now the top search result. The sight of her, naked, makeup done to look like the Night Queen, staring up at me with smug superiority as I helplessly lost control between her tits, was seared into my memory.

Replaying it in my mind's eye while I was masturbating had a predictable effect, and it wasn't long at all before I finished.

---

As the bliss of the orgasm faded, I was always left with the same, humiliating thought: I had called her

Mistress

. Begged her to make me cum.

At least the post-nut clarity was helpful in spurring me to action.

I started by firing off a response to her first email. This one was simple: I was excited to play, sorry to miss Mike but was sure we'd get Meldrin healed up soon, and appreciative of our esteemed Dungeon Mistress for her help with wardrobe. Everybody else had responded, I should too, I figured.

The second email I spent a lot longer revising, but in the end, it was simple too.

---

Subj: Re: Size

I'm a medium or a large for sure. Just too long to wear a small, you know?

Thanks for the wardrobe help!

Chris

---

I waited for her to reply. I wasn't even sure what I was hoping she'd say. '

Oh wow, Chris, now I remember, I loved how big your dick was'?

Actually, I guess I

was

hoping she'd said that.

But she didn't reply.

I also wondered what she'd want me to wear. That sent me into a whole new tailspin -- what if it was embarrassing? I wasn't worried about showing off my body; I was a little skinny, but it gave me a leanness that I liked. I didn't think I looked too bad. But what if she made me wear something weird, like a dress, or...

I tried to re-rail my thoughts. She couldn't

make me

do anything. If it got weird, I'd say no. If that meant I couldn't play...well, I'd just leave.

I recognized that I'd told myself the same thing last session, too. But this time would be different.

---

By the time the day of the next session rolled around, I was basically bouncing off the inside of my own head.

I had half-convinced myself I'd imagined all the interrogation scenes from the first session.

And I'd also half-convinced myself that the best course of action was just to email saying that I was sick and skipping the session.

...But I was also half-convinced that Monica had asked me to show up early because she wanted a chance to tease me before everyone else arrived.

And part of me

wanted

that.

She had asked me to show up early.

I glanced at the time and realized that if I was going to be there early at all, I had to leave

right now

.

Shit

.

I zipped out the door.

---

"Hi, Chris."

Monica wasn't in costume yet. In fact, she looked like she was freshly out of the shower; her black hair was damp. She was wearing a light cotton bathrobe.

"Hey, Monica. Uh, this isn't your costume for the week, is it?"

My joke was spoiled somewhat by my complete and utter inability to keep my eyes on her face. The robe clung to the curve of her breasts appealingly, and all I could think about was how they had felt against me, last session.

I could feel her gaze on me, watching me as I looked at her body. She smiled. "No, I'm not in my costume yet. Come on in."

I followed her inside.

She turned and looked at me over her shoulder. "I'm going to finish getting ready using the bathroom, but I laid your stuff out in my bedroom -- you can go ahead and put it on."

She walked into the bathroom. A moment later, I could hear the hairdryer start. Feeling dismissed, I lingered uncertainly for a moment before heading into her bedroom.

Laid out on the bed were a pair of leather pants and what looked like it would be an old-fashioned loose, off-white tunic-style shirt. I breathed a sigh of relief --

not a dress

-- and closed the door behind me, stripping and starting to change.

The tunic was no problem. It had a deep v and loose laces that left it open almost to my navel, but I was fine with that. Looking at myself in the mirror in Monica's bedroom, I thought I looked pretty good -- it gave me a kind of swashbuckling flair. I felt a bit of gratitude to Monica -- this wasn't weird, it was cool. She'd done a good job.

Then I tried the leather pants, which turned out to be a completely different story. They were

tight.

I struggled into them. They were cut like joggers -- tight around the calves, a bit looser in the thighs, but

looser

was all relative -- they basically clung to my legs. I got them on once, looked at myself in the mirror, and realized that my boxers looked

bad

underneath them. Weirdly bunched up.

I hesitated for a moment indecisively, feeling embarrassed...and made the only decision I could. Erin and Liz were both in costume. Monica took it seriously, too. And it really did look awful, with the boxers on -- like I was wearing a diaper or something.

I stripped the pants off, pulled off my boxers and put them in a pile with the rest of my clothes, and got back into the leather pants, commando.

I had just managed to finally get them all the way on and was grappling with some odd, complicated dressy laces at the waistband when Monica opened the door. "Hey, everything going okay in here? Everything fits?"

She hadn't even knocked

.

"I, uh, yeah, just a sec--" I frantically tried to tie up the waistband as she moved into the room, but there must be some trick to the laces I didn't understand.

"Oh, let me help with that. These are always stupidly complicated." Monica moved over and knelt in front of me, pushed my hands away.

Looking down at her, I took in what

she

was wearing for the first time.

She had a wig on. At least, that's what I assumed it was. Her dark hair was now a platinum blonde, done into some intricate braidwork down her back.

Her lipstick was a bright, cherry red.

I didn't know what she'd done for makeup, or tanning spray, or whatever she'd used on her skin. But her otherwise ivory skin had an even tan, now. And she had given herself a scar, somehow. It was just above one eyebrow, the pale remnant of a wound -- as if she'd been nicked by a blade there, long ago.

She was wearing a silvery sheath dress. The neckline was low, showing off full, tanned breasts. It clung to her body. With her knelt in front of me as she worked on the laces of the drawstring, I was looking down her back, at the way the dress highlighted the curving lines of her body: the tapered waist, the way her hips and ass flared out...

I was silently staring, I realized.

I had to say

something

. "Wow, you, uh, look great. Is this a new character?"

She glanced up and gave me a knowing smile. "Thanks, Chris. Yes, you all will be meeting the Daughter of Blades today, one way or another, I suspect. And I didn't realize you liked blondes. You've always seemed like a

brunette

kind of guy, to me. Interesting."

I flushed. Monica, Erin,

and

Liz all had darker hair.

Before I could ask more about the Daughter of Blades, though, the

suggestiveness

of the position she was in dawned on me. She was kneeling in front of me, right at waist height, staring fixedly at my crotch with a determined look on her face as she did up the complicated laces. Then I realized -- watching as she pulled at the laces, re-laced them...that she could probably tell I had taken off my boxers, wasn't wearing anything under the pants.

The whole situation had me starting to get hard. And these were

very

tight pants.

Fortunately, she stood up after another moment or two. "Okay, that should do it." Her face was inches from mine, and there was a moment of silence as she looked me in the eye, a challenging sparkle in her gaze, like she was waiting to see if I'd say -- or do -- something.

But I was flustered and intimidated, and stood staring at her, awkwardly. So eventually, she spoke first. "Well, let's see how you look, Cedwin. Then we can decide on some finishing touches."

I turned around and we both looked in the mirror, inspecting the transformation.

I broke into a smile. "Hey, thanks for the help Monica. I look pretty good."

Those bright red lips curved into a smile as she gave me a once over. "I like it

too

."

In the mirror, I could see her gaze lingering on my groin. My cock was clearly outlined in the pants, I realized, even though it was only at half mast. I opened my mouth to respond, but Monica just breezed on. "Now, accessories always complete an outfit like this. First of all -- okay if I give you a temporary tattoo?"

The change of subject left me behind. "What? I, uh, sure..."

"Good. Hold out your forearm." She went over to her vanity, and returned to my side with a sponge and a glossy quarter-sheet of paper.

The Tower

, I realized. Cedwin's tattoo. Or, at least, what used to be his tattoo -- and was now an imitation, placed there by the Night Queen. "H-how did you even

make

this?"

"I know a tattoo artist who owes me a few favors. He helps me out with this sort of thing for costumes, now and then." Her hand drifted across my forearm as she decided how to place the tattoo.

Her fingers felt good, playing over my skin. I tried not to read into what it meant that the

tattoo guy owed her a few favors

. Tried -- and failed -- not to imagine what the favors in question were for. "Oh, uh, cool."

She sponged my arm and applied the temporary tattoo. "Okay, let that sit for a moment while it transfers. Now, let's see..." she inspected me for a few seconds, eyes roving over my body. "...Some jewelry, maybe...something masculine, but with a bit of an edge to it..."

She went over to a cabinet and rummaged out, handing me a leather bracelet, which I put on around the arm without a tattoo, and an iron ring, which went on the index finger of one of my hands.

She nodded her approval, still looking at me. "Hmm...almost enough, but..." and then she snapped her fingers. She went back to the cabinet, returning with a silvery chain.

A crescent moon dangled from it.

She stood up and, leaning up and in, reached behind me to fasten it around my neck. "After all," she murmured, right in my ear, "You did dedicate yourself to your

Mistress

. Even if the

other

players don't know that,

you and I

do."

I was speechless. At the word

Mistress

, my cock surged.

Then she peeled away the tattoo transfer paper, and gave me a final once over. She nodded, looking pleased, and gestured at the mirror. "What do you think?"

I turned back to the mirror.

The leggings clung around my calves, a bit looser through the thigh. The laces at the waist were...well,

flattering

, somehow making my waist look slimmer, and thus my shoulders broader, legs more muscular. The baggy tunic, draped loosely over my lean upper body, gave me an undeniably relaxed, devil-may-care attitude -- although admittedly at the moment I felt wound pretty tight from Monica's promixity.

To be honest, I looked pretty fucking good.

Finally, she met my eyes. "Yep, I think you're all set." And then her eyes drifted down, again. "And I guess you were right; certainly a medium or a large, not a

small

."

You could, I realized, see the outline of my mostly-hard cock

very

clearly, now. I flushed with pleasure -- and then embarrassment at how good the compliment made me feel.

I had imagined a few different snappy comebacks if this topic had come up again; in the moment, none of them came to mind, though, so there was another awkward silence.

She looked at my cock a moment longer, then up at my eyes, expectant, waiting for me to say something...and then her doorbell rang. "That'll be Liz," she murmured. "I'll go let her in."

At the thought of my friends seeing me in this outfit, I tried adjusting myself to make the outline of my cock less prominent, but there was no use; the pants were tight enough that it was just going to be on display. I settled for putting it in a position that I hoped would just be a nice bulge -- suggestive, masculine, but inoffensive, as long as I didn't get

too

hard.

But it was still quite obvious. Well, at least the loose tunic would be draped over it while we were all sitting down to play.

I went out to meet Liz.

---

"Oh my god, Chris! Or should I say,

Cedwin

. Monica, you've outdone yourself." Liz was emphatic as she looked at me, walking around, making me show off the tattoo.

I held out my forearm for her inspection.

I was, admittedly, distracted. "You, uh, look awesome too, Liz..."

Liz was also in costume.

Liz mostly wore loose, flowing dresses, or professional work attire. The occasional pair of jeans with a graphic tee.

Lucia

, apparently, wore skintight black leather leggings. Heeled black leather boots. A strappy top, with a bandolier of small knives, went across her chest; she was wearing a red and gold bandana around her neck. Brown hair, up in a long ponytail, completed the look.

I was finding it difficult not to just follow Liz's ass with my eyes as she walked around me, inspecting at the various details on my costume. God, the way she

filled out

those leggings. I could see her butt flex and shift with every step as she walked around me.

My nerdy childhood friend had evidently been spending some time in the gym.

"Hm?" Liz glanced up at me. "Oh, I guess I wasn't in my costume last time, huh? You like it? I like the knives. And the boots. Monica helped me find the right pair. These are totally badass." She carefully lifted one leg, putting a boot on the table in front of me. I tried to inspect only the boot, did my best to ignore the interesting things that the position did to her butt and thighs.

You're wearing tight pants,

I reminded myself, trying not to have a physical response. Fortunately, Liz's attention was pulled away.

"And Monica,

you

look ravishing!" Liz exclaimed, turning to her. "What character are you? We haven't seen this costume yet!"

Monica gave a small smile; she had moved behind her counter and was making drinks. "Why, none other than the Daughter of Blades stands before you, Lucia."

Liz gave a returning grin, and shifted to her Lucia voice -- huskier. "Well, well. Her reputation precedes her."

The doorbell rang -- Erin, presumably -- and Monica stepped away to let her in.

I took the opportunity to ask Liz a question. "Who's the Daughter of Blades?"

"Lucia is a member of a thieves guild, the Hemlock Sisterhood," she explained. "It's um, wide-ranging -- chapters in each city, a shadowy network of operatives if you need a rare or dangerous item, want someone kidnapped or poisoned, that kind of thing. As the name suggests, it's ladies-only. The Daughter of Blades runs the Ravensgate chapter; she's kind of infamous."

I nodded, uncertainly. "Oh. Think she could help us get some revenge on the Night Queen?"

Liz smiled, and in Lucia's voice -- a smoky purr -- said, "That's what we're gonna find out, handsome."

I had to admit that, like Erin, I

liked

Liz's sexy little Lucia voice.

And -- feeling the stirring in my groin -- I realized that increasingly, I did

not

like my odds of getting through this without giving Liz or Erin a clear eyeful of my hard cock. I slid into my seat, figuring sitting would make it less obvious.

Fortunately, I was rescued as Monica walked back into the room from her front hallway, followed by Erin.

"Erin, that dress is great! You have to let me make some alterations, though. I could totally tweak the hemline and the neck, really lean in to the kind of sexy-woodlands-druid look you've got going," Monica was saying.

"Sure, that sounds awesome! I can leave it with you when we're done," Erin responded. "And Monica, looking like

that

in

your

dress, you'd do

great

if you ever want to go corporate. You just let me know, I know some hiring mangers who'd bring you on in a heartbeat. And what kind of makeup are you using? Your skin is

so

tan, and it's so

even

-- is that just like a bronzer, or self-tanner, or..." Erin kept going. I admittedly stopped listening to the makeup talk.