[Vol. 2 pt. 57]
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After getting everything back to the dungeon, I find myself being pulled in four different directions for attention albeit not so obviously.

Thera is the only one not trying to get my attention. Instead, she’s just standing back and enjoying the sight.

As for the four wanting my attention…

Akorya is very obvious about her intentions as she whines and moans about how she wants to have some fun with me. Lily is right there with her, so I suppose it’s more like I’m being pulled in three directions with Akorya and Lily working together. Though, Lily is just nodding along at Akorya’s words rather than actually trying to convince me herself.

Then there are the other two who are not so obvious about what they want. Anna has taken another bath and keeps on whispering to me about the roleplay, and then there is Lupi who’s just staying close to me no matter what.

So, really, I’m not actually being pulled in four different directions. That was a bad way to describe my current situation. It’s more like Akorya and Lily want me to go have sex with them, Anna wants me to teach her all about the wonderful world of roleplaying, and Lupi seems like she’s going to be curiously butting her head into whatever – or whoever, it is that I end up doing.

Unfortunately for Lily and Akorya, I do have a deal that I need to keep, and I doubt that Anna wants Lupi to watch what we get up to.

“Later, alright? I’ll do whatever you two want me to do to you later,” I tell Akorya and Lily.

Akorya pouts at first, but Lily smiles and nods.

“You’ll just have to keep each other company until I’m ready for you. Alright?”

Lily looks at Akorya and then blushes before looking away. I guess that the thought of doing things with Akorya without me being involved is still embarrassing to her, but Akorya doesn’t seem hesitant at all about it.

“It’s boring without a dick involved, but okay!” Akorya says, grabbing Lily by her wrists to lead her away.

She really didn’t waste any time; Akorya must be pretty horny.

“Lupi, can you go stay with Frederick for a while? I want you two to talk and exchange information so that we can all learn more about each other,” I say.

“What are you going to do with her?” Lupi asks, looking at Anna.

“That’s private.”

“Is it that roleplay thing? I want to know what that is.”

“I’ll explain it later, alright?” I offer, causing Anna to blush and look away.

“Okay,” Lupi answers before heading back into the room where Frederick is, turning around to look at me, and then leaving.

“Such a popular man, darling,” Thera teases.

“Yeah, yeah,” I reply.

“Are you not glad that you do not have to deal with me wanting your attention as well?”

“You know I’d like that.”

“Perhaps another time, darling.”

I smile and shake my head before turning my attention to Anna finally. “Alright. Let’s go over here and have a talk,” I say, pulling her back into the hot springs room.

Anna is already starting to look excited.

“Are you ready?” I ask her.

“For – for the ‘roleplay,’ yes,” she answers.

“Good girl.”

Those words bring a slight curl to her lips.

“Now then,” I pause to step closer to her, “we have to establish the rules. Tell me, and be as open and as honest as you can, what your limits are.”

“My… limits?”

“Oral. Vaginal. Anal. Cumming inside. Slapping. Biting. Spanking. Marking. Choking. Tell me which fetishes you are not comfortable with and that you do not want to happen.”

“Isn’t – isn’t the point of pretending that you will do whatever you want to me regardless of whether I want it or not?”

“That’s what we’re going to be pretending, yes, but I still need to know what you like and don’t like. Consent is important even if we’re pretending that I’m forcing myself onto you.”

“I have only ever pleasured myself… normally, so I do not know if I would like the others, but… n-none of it sounds bad, to pretend, of course.”

“In that case, I’m going to give you two ways of stopping everything and letting me know that you’re uncomfortable. The first is a safeword: coffee. Say it.”

“Coffee?”

“Right. If you say no, beg me to stop, ask for help, or anything else, I’m going to assume that you’re pretending and actually want me to continue. ‘Coffee’ isn’t something that you would accidentally say or anything that could be misunderstood. So, say it and I will stop the instant you do. Understand?”

She’s blushing even more now. “Yes.”

“Say it again.”

“Coffee.”

“Good girl.”

Her lips curl more than before.

“Now,” I continue, “the other method of getting me to stop will be to stick your pinkies straight out while curling in the rest of your fingers. Like this.” I demonstrate by forming two fists and then sticking my pinkies out. “Now, show me.”

She does exactly as I did.

“Good. Now, repeat me to me the two methods of making me stop.”

“I can say ‘coffee’ or I can stick my pinkies out like this,” she says and sticks her pinkies out again.

“Exactly. Now, do you care what form of mine I use? I could be a forest imp, lusticore, gnarled wolf, or cum slime.”

Her eyes widen a bit at the last option and she looks away, but instead of confirming my thoughts, she answers with, “I – I don’t have a preference.”

“Alright. One last thing. I’m going to have you leave the dungeon and walk back toward the wagon. Do you know what you’re going to be doing?”

She shakes her head.

“You’re going to be acting like you’re heading back to the road to return to town. Then, I’m going to ‘attack’ you, and you’re going to fight back. Don’t fight back too seriously, but act like you would if you were actually being attacked. You’ll also know that it’s me attacking you because the first thing that I do to you will be touching behind your right ear. Got it?”

“So… pretend that I’m leaving, and you will attack me at random? And touch me behind my right ear?”

“Right. And remember: coffee or sticking your pinkies out.”

She sticks her pinkies out and says, “Coffee.”

“Perfect.”

“Is – is there anything else that I need to do or know? I’ve never done – pretended to do anything like this with somebody else.”

“You want to pretend that you’re a victim being attacked by a monster, right? Then all you have to do is pretend to be the victim who can’t fight off the monster and who eventually gives in to the unbelievable pleasure that the monster forces onto you. All you have to do is fight back until you don’t want to anymore, and then you let the monster overwhelm you with pleasure far greater than anything you have ever felt before.”

“A-and then?”

“Spoilers.”

She gulps.

“Are you ready to go and play pretend?”

“I… think so. Ju-just remember that this is only pretend! Nothing is actually happening. It’s all fake.”

“Of course. Everything that happens between now and after we’re done is all just pretend. Not a single bit of it is real.”

“I am just making sure you understand that.”

“I understand it completely. Don’t worry.”

“Then… should we start? Do I just… leave?”

“Whenever you’re ready. Just remember: coffee and pinkies.”

“Coffee and pinkies.”

Anna turns around to leave but then stops and looks back at me.

She opens her mouth, closes it, sighs, and then says, “Thanks.”

“Nothing to thank me for.”

She smiles and turns back around to head out of the dungeon.

Alright. It’s been a while since I’ve last done anything like this with anybody. The closest I’ve been to roleplaying some rape was just dominating Lily and Akorya.

Never was a big fan of it if I’m being honest with myself. It’s something that sounds better than it actually is to me. With what I went through with my uncle, roleplaying it with partners when I was younger was great for me overcoming some of that, but… well, I’m not going to worry too much about it. I’ll still enjoy it regardless and it’s what my partner wants. I need to be in a good mental state if I want to make sure that she thoroughly enjoys the experience.

Besides, I doubt that she plans on acting the part of a victim as much as I would. It’s most likely going to end up just being me and her having some kinky sex without any roleplay past the first minute or so of it. I don’t think she’d be a very convincing actress even if she does decide to really try and play it up.

Last girl I was with who wanted to really act the part… yeah, I don’t think any man could go through with her. She was way too damn convincing. Crying and screaming and begging one minute with extremely realistic expressions and body language, and then angry and disappointed the next minute when you won’t shut up about making sure that she’s actually alright.

There wasn’t a single one of us at my old place who could give her what she wanted. She got refunded after every single one of us that she tried out since none of us could make it through her extreme acting.

Even my boss thought she was insane, and my boss was one kinky woman. She told me she’d never seen a girl as extreme as that one in over sixty years.

Damn. My boss was really old now that I think about it. Didn’t look a day over fifty and still acted like a twenty-year-old, though.

Her and Frederick would probably get along. Well, they would if she was here on this world and not retired with her harem of young pool boys.

Even now, I bet she’s fanning herself while one man massages her feet, another feeds her grapes, one rubs her shoulders, and the last one fucks her.

She knew how to live.

I wonder how her fortune is going to get split up once she passes.

I also wonder what life would be like if I would have accepted her offer to join her harem down at some beach south of the equator.

Probably too sandy. Never have been a big fan of sand. It’s coarse, rough, irritating, and it gets everywhere.

Everywhere.

I tried having sex on a beach once.

No matter how many towels you put down to try and avoid sand from getting on and in everything… they just don’t help. Sand will find a way.

Sand always finds a way.

And it will continue finding a way for a week after you leave the beach.

At least it’s not as bad as its more fabulous cousin, glitter. I remember when I had one partner who really loved glitter. She and her boyfriend thought it would be great to have a threesome on a bed covered in glitter for some reason that I was too horny to care about.

Even though it was at their apartment, I was still finding glitter in my own bedroom for a couple of weeks after that.

It must have rode me home and then procreated or something to breed more glitter.

Sand and glitter… I fear what would happen if the two ever decided to work together.

Well, now that I’m reminded of how uncomfortable it was to get sand on my dick and how annoying it was to find glitter on my bed for weeks, I suppose it’s time to get going. Anna should be a good little distance away from the dungeon now, and she should be nervous and wondering when I’m going to go and get her.

I think that my cum slime form would be perfect for this. I was teasing her about tentacles before, it’s been a while since I’ve used this form specifically, and it will let me keep a close eye on her. It might have the smallest body out of all my forms, but I have the most visibility from it since I can turn any point of my slime into an “eye.” Well, even though it doesn’t actually look like there are eyes or anything like that when I do it, I’m still able to see from that part of the slime.

This means that, no matter what position we might be in, I’ll be able to watch out for her hands to see if she gives me the sign to stop at any point.

It’s been a while since I’ve had to actually worry about this. With Lily and Akorya, I’m confident in knowing their bodies and tastes to the point where I strongly doubt I would ever do anything that they wouldn’t like. I still look out, of course, but I know they’ll realistically never use the signs I’ve given them unless I’m overestimating how well we work together. As for Anna, though… well, she’s new to this whole thing and it will be my first time with her. I’ve got a lot to learn.

That’s another reason why my cum slime form is perfect. I can play with her whole body at once with it which means getting to test her in all sorts of different ways.

This will be fun.

“Heading out, boss?” Al Capra asks.

“Yup. Hold the place down for me,” I answer.

“Does it involve the lady who just left?”

“Remember, my goat friend, that we offer discreet services here. No kissing and telling.”

Al Capra leans back and smiles which is kind of weird seeing coming from him. “Got it, boss.”

He knows.

Then again, it’s pretty obvious.

Now to find Anna.

Thankfully, it’s not too difficult. All I have to do is walk along the side of the road rather than on it so that she doesn’t see me approaching.

She’s not even halfway to the road yet, so we’re still a nice distance away. Nobody should hear anything unless she decides to scream pretty damn loud, and my tentacles are going to be taking care of her mouth to make sure that she won’t be doing that.

“Feral Form: Cum Slime.”

My body shrinks down and turns into creamy slime.

Now then. She’s strong and wants to roleplay, so I can’t just obviously approach her or call out to her. I’ve got to ambush her and force myself onto her.

However, I also need to touch her behind her right ear so that she knows it’s me. Seeing as how I can transform into monsters, it wouldn’t be good if a random monster came out of nowhere and decided to try and rape her while she thinks that it’s actually me. The chances of that might be extremely low, sure, but I’d rather not risk it.

Staying safe is one of the key rules of the games, after all.

Fortunately, I think I have an idea on how to approach her. I’ll just have to hope she’s not paying too much attention to her surroundings since she could probably discover me if she does. Or, if she does figure out where I am, she pretends that she doesn’t.

As for how I’m going to reach her… I shrink my body some more to produce one single, long tentacle that reaches up and wraps around a tree branch.

I then shrink my body even more to make another one of these tentacles to grab onto a high-above branch farther ahead.

I should be able to swing from branch to branch this way until I’m directly over her. As long as I’m careful, too, it doesn’t make too much noise.

Branch to branch, I swing above the path as stealthily as I can until I’m directly above her.

Good. She hasn’t reacted at all. That means she’s either not trying hard to notice me or that she’s playing along.

Now, hanging from only a single tentacle, I reach my other – shit.

I completely forgot that I won’t have much time now since I got into the form to approach her. I’ve already wasted a couple of minutes!

I’m going to have to be quick.

I extend a single, thin tentacle down to graze against the back of her right ear.

By the time she turns her head to look up at me, I’m already falling toward her.

Honestly, I let go of the branch I was hanging from as soon as my tentacle was close to her ear. Falling is what dropped it the rest of the way to touch her.

Her eyes widen for a second, but not out of surprise nor arousal.

She looks genuinely pissed at me.

The look goes away as soon as she realizes what’s happening, her eyes softening and lips threatening to smile, but fuck me did that glare scare me for a second.

Most of my slimy body lands on top of her face.

I don’t want to choke her, so I quickly move farther down her body so that I’m resting on her chest while leaving a single tentacle forcing its way into her mouth.

Two more tentacles go for her wrists to restrain them before she has a chance to draw her sword. Though, I don’t think she has any intention of even pretending that she’s going to draw it.

She’s actually… pretty stiff.

Her lips aren’t budging and my tentacle isn’t strong enough to force itself into her mouth on its own, her arms and legs are locked up, and her eyes look excited but at the same time way, way too nervous.

She’s not saying the word or sticking her pinkies out, though.

I don’t think this is going to be too much of a rape roleplay. At this rate, I’m going to have to ease her into things and try to relax her.

Let’s start off with these tits of hers.

Still sitting on top of her chest, I stick several tentacles out from underneath me to slide down into her clothes. Her face turns a brighter shade of red the more she can feel my tentacles wrapping around her tits, but she’s still not saying the safeword nor is she sticking her pinkies out.

The tentacles coil around her breasts and squeeze as the tips go for her nipples, enveloping them in their slime before joining in on the squeezing.

She seems to tense up even more for a few seconds before finally relaxing her shoulders and opening her legs just a bit.

I’m really torn between forcing myself on her and playing the part of her attacker or taking things slow and easy for her sake.

But, she wanted me to “rape” her, and she’s not giving me either of the signs.

She’s trusting me, so I’ll trust her.

Just as several of my tentacles have slipped into her uniform, I slide two more tentacles down the front of her torso until they reach the bottom of her skirt where they then slide up underneath it.

The smaller of the two slides underneath her panties to shrink its tip and absorb her clit into it to gently pulsate and suck while the other, thicker tentacle grinds up against her slit over the fabric.

Her legs open even wider now as a moan escapes her mouth.

The tentacle that has been trying to get into her mouth doesn’t waste any time pushing into her, its tip dripping my cum directly onto her tongue. I feel her pull her tongue away and she doesn’t seem like she knows how to react to the taste of my cum, but… I do know that she’s getting even more aroused. It’s not my slime that is making her as wet as she is right now.

For both of our sakes, I think it’s time that I speed things up now.

I drop to the ground and lift her up, carrying her off of the road to behind a nearby bush where I push her down to the ground with my tendrils.

With her on her back, the tentacles around her breasts pull them out from her uniform before working her tits even harder and rougher than before. Their tips, still enveloping her nipples, suck and tug on them now which forces her back to arch and her voice to moan around the tentacle that I’m pushing deeper into her throat.

I’ve got to admit that if it wasn’t for just how fucking amazing her body is, I’d probably be bored right now. She’s not pretending to fight back, she’s not helping me out at all, her tongue is lying still in her mouth, and the only movement that she is making at all is arching her back whenever I do something that she likes.

It seems like her nipples might be her weak spots since that has been getting the most reactions out of her. In that case, I form several smaller, hair-thin tentacles inside of the tips of the ones around her nipples, wrap them around her nipples, and start pulling. Not only that, but I’m able to vibrate them at the same time.

I can tell that she’s moaning more now going by the vibrations against my tentacle in her throat, but the rest of her… yeah, maybe I’m spoiled, but she has got to be the least active partner I’ve ever had. Even if this is supposed to be roleplay where she’s not supposed to really try and make me feel good or do anything other than try to resist it, she’s just not doing anything.

But, she’s still got an amazing body and it still feels damn good to be inside of her, so it’s not like I won’t be able to cum for her. I just can’t bring myself to really go all-out. This is more like just going through the motions and hoping that she’ll be satisfied with this alone.

She does arch her back and moan even more once I start thrusting one of my tentacles in and out of her pussy, but that’s it.

Her legs stay still, her arms remain wherever I place them with my tentacles around her wrists, and she doesn’t even open her eyes to look at me. She’s just blushing and keeping her eyes shut.

If it wasn’t for the fact that she’s not sticking her pinkies out, and that I can feel how much she’s moaning against my tentacle in her throat, I wouldn’t even be able to tell if she’s enjoying this or not.

I’m half tempted to stop and ask to make sure that she is, but… I’m probably almost out of time anyways.

Squeezing her breasts, sucking and vibrating against her nipples and clit, fucking her mouth, and thrusting into her pussy, my tentacles continue using her body until I feel myself able to cum. While I might normally hold back to try and make myself last a little bit longer, finally being close enough to cum is actually a relief this time.

My tentacles paint the inside of her pussy and throat white with my cum while giving her a nice coating on her tits.

Her pinkies stick out, prompting me to immediately pull out and return to my human form despite being mid-orgasm.

“What’s wrong?” I ask her.

She coughs and spits some cum out before swallowing whatever is left.

“N-nothing,” she answers. “I couldn’t breathe and panicked, but – but it was nice.”

Ah, shit. I’m so used to Lily and Akorya being able to swallow tons of cum without any problem that I’ve slipped up and forgot that Anna might not be able to handle that.

It’s been so long since I’ve last been with a girl like this. I’ve got to admit that I’m kind of feeling like a failure right now.

“Sorry, I should have been more careful,” I tell her.

Anna shakes her head with one hand resting over her abdomen. “Th-that was… you truly lived up to your words. I – I didn’t know it was possible to feel such pleasure.”

Seriously? I couldn’t even get into it and felt like I had no idea how to make her feel good. “I’m uh, glad you enjoyed it.”

She tilts her head and looks up at me. “What’s wrong?”

“Ah, nothing. Don’t—”

“Are you forgetting who you are talking to? I know when something is wrong and when somebody is lying,” she says, sounding more stern rather than like somebody relaxed and pleased post-sex now.

“Sorry.” Ah, damn it. Communication is key, and here I am even failing at that now. I just don’t want to upset her since she seems to think that everything was fine when really… but I need to be honest. “Anna, you’re beautiful with an amazing body, and I love how open you are to try new things, but—”

“I didn’t do enough, did I?”

“Yeah.”

“I was worried about that at first, but once the pleasure began, I was selfish and decided to focus on enjoying it. I am sorry if I was not able to satisfy you in return.”

“No, no, you’re fine. You’re new to this, so starting off with something like rape roleplay probably wasn’t a good idea. That’s more… something that you do when you’ve got experience. Honestly, I’m relieved to know you enjoyed it. I couldn’t even tell if you orgasmed or not.”

“I – I did. Multiple times.”

“Really?”

She blushes some more and looks away.

“Well, I’m glad. All that matters is that you enjoyed it.”

“I will try harder next time we have – we pretend.”

“Oh? Was it so good that you’re already looking forward to the next time?” I tease.

“I already told you that it was. Don’t make me say it again,” she answers, looking up at me with a slight pout. “I just… don’t know what I am supposed to do – how I am supposed to act or say. Should I have fought back? Used my legs somehow?”

She really doesn’t seem to know anything about how to act during sex.

And that gives me an idea.

If she’s a Patience follower, into being forced, and doesn’t know what to do… I could teach her what to do, or I could set up the ultimate session to truly test her patience that wouldn’t require her to do anything at all other than to “suffer” through what I put her through.

I’m going to need some rope and toys for that, though. Though, the downside is that there are no vibrators in this world. Nothing to electrocute her with, either.

Hang on.

Al Capra can do some carpentry, Thera has got me covered when it comes to bindings, and there is Wally who knows electricity magic and how to build things that takes advantage of that.

Alternatively, I could just give Anna to Lephacoda for a few hours.

Back to my original line of thought, though, I think I’ve discovered how I can make the best use out of my strengths while working with Anna’s weaknesses.

Then again, I could just train her to be more active.

“Alright, Anna. Be honest with me. Which would you rather experience: me training you how to be a good, active participant during sex – pretend, or getting to experience even more pleasure than what you felt this time while letting me perform at my best without you having to do a single thing other than letting me do whatever I want to you.”

“Well, when you put it that way… you do make it sound like the latter option is the superior one. I think I would prefer that, but I also want to… I want to learn how to be better myself, too.”

“Then we’ll do both, but next time, we’ll start with the latter one. Alright?”

“The look in your eyes is promising.”

“Do I look that excited?”

“I think this is the most excited I have ever seen you.”

“Then that’s my proof to you that I mean it when I say, next time, you will really experience pleasure and get to see me at my best. I do love some good bondage play and having a toy to do anything I want to, and it’s been a while since I’ve done that kind of play. I just have to set up a room specifically for it and get some tools ready.”

Anna bites her lower lip and squeezes her cum-stained thighs together. “T-tools?”

“I’m not going to soil the surprise. You’re just going to have to be patient and wait to discover what I mean. You can be patient, can’t you?”

Her lips part and she lets out a needy moan.

Damn it, I’m so stupid. Why didn’t I think of this sooner? If there is anybody to go full sadist on with orgasm denial, toys, bondage, and taking my time, it’s going to be Anna, one of the top followers of Patience.

She might be interested in rape roleplay, but I’m confident I can give her a new fetish that makes her completely forget about that.

“I – I can wait,” she says.

“Good girl.”

She lets out another needy breath.

As much as I enjoy my monster forms, I don’t think they’re what she needs. She needs me to take the time to thoroughly tease and abuse every single inch of her body while degrading her and teasing her. Just talking to her like this feels like she’s getting more excited than she was at any point during our play, even if she did orgasm during it.

Alright, Damian. It’s time to be a good, proper dom by setting up the perfect scenario for your partner. I’m not just going to go with the flow of roleplay this time since that just didn’t work at all. Next time, I’m going to have an entire plan set up for her.

Now I’m the one getting excited and hyped up.

Lily and Akorya? We’re compatible enough that we can just do whatever to each other and fully enjoy it. But Anna? She requires more strategizing than that. It’d be nice if I could just do anything with her and fully enjoy it like I can with Lily and Akorya, but not everybody is a flawless match no matter what the circumstances are.

But that doesn’t mean we can’t have a perfect time together. It just means I have to put a bit more thought into it.

I will call this, “Operation: Judge Breaker.”

That’s a stupid name now that I’ve actually thought about it, but it’s good enough.

Anna is a “judge,” and I am going to break her with my experience and planning until she’s drooling, broken mess utterly lost to pleasure.

I’m pretty sure she was expecting something like that from this session of ours anyways, but I couldn’t deliver it to her this way.

Next time… next time is going to be fun.

“Also, thanks,” Anna says.

“Hm? What for?” I ask.

“Stopping when I gave you the sign.”

“Oh, nothing to thank me for. That’s the whole point of the sign. We’re in this together, right?”

“I feel bad. You did so much for me and kept considering me the entire time, but you didn’t get to enjoy it as much as me.”

“Don’t worry. Next time, I’m going to do even more for you and you won’t even be able to do anything for me, and I’m going to enjoy the fuck out of it.”

“How?”

“You’ll see.”

“That sounds even more unfair to you.”

“Trust me. It’s going to be more than fun for me.”

“Then I will look forward to,” Anna shuts her mouth and puffs out her cheeks, placing one hand over her mouth.

She looks like she’s about to cry from embarrassment.

I gently rub the top of her head and say, “Don’t worry about it. Lots of embarrassing, funny, and weird things happen during sex and after it. It’s all part of the show, and the sooner you stop treating it like some super serious and perfect thing, the more you’ll get to enjoy it.”

“It’s – it’s not feminine at all,” she whines.

“I understand why you might be concerned about that. It’s only natural. But, seriously, you don’t have to worry about it. I’m the last person who would ever judge somebody for a natural function of their body.”

Her eyes quiver before looking away, her blush extending up to the tops of her ears at this point.

“Thanks,” she says under her breath.

“No problem,” I say and give her a pat on the back.

That forces the hiccup out of her, causing her to give me that same, scary glare from earlier.

She raises her hand and… taps it against my cheek.

“It took so much effort to hold that back, and then you went and made me do it anyways,” she pouts.

“And do you think I’m judging you for it?” I ask.

She looks me over before sighing and saying, “No.”

“Then there’s no problem. Now, let’s go and get you washed up.”

8