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Chapter 37 - Lissa and Anna - Royal Approval (C)

A glory hole anthology series involving all manner of ladies from all over games, comics, anime, and more, holes in walls, and the dicks poking out of them. Chapters with a (P) were voted on by my Patreon, and chapters with a (C) are commissions.

Chapter 37 - Lissa and Anna - Royal Approval (C)

Chapter 37 - Lissa and Anna - Royal Approval (C)
Commission for SHSL-Despair
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Anna had made it her mission to get glory holes accepted in Ylisse; the money to be made there was absolutely mouth watering, but to do it, she was going to need royal approval, and as she led Lissa into the room, she sought to garner exactly that. She had explained it to Chrom before, but spared the sweet princess any specific details beyond the idea she wanted to show her something for business.

Lissa's curiosity ran wild as she walked into the cramped, poorly lit room. "It's... Something," she said, furrowing her brow and not seeing where in this tiny chamber money was supposed to be. "Oh, what's this hole?" she asked, motioning toward it curiously. Maybe this whole business venture had something to do with that. She leaned down to look through it, seeing nothing and only getting more confused, like her attempts to find answers just left her with more questions. This was strange, but she was willing to indulge the idea that there were answers to these things that might make a lot of sense.

"That hole is the money maker," Anna said happily. "Men will put their cocks through it, and then the women on the other side will suck and get fucked by them." She was bright and eager to give up the details now, watching as terror crept across Lissa's face, realizing just what this was. Seeing the realization dawn on her was an absolute treat, the sort of corruption of the youth that Anna should not have wanted as much as she did, but she couldn't deny that it was a blast to catch someone off guard like that. 

Lissa was about to gasp and squeal and try to make a run for the door, scandalized and amazed by everything she was hearing, but the ringing of a bell stopped her, as did the hoarse, rushed whisper from Anna of, "Don't make a sound," as she stood there, eyes shifting toward the hole. Lissa's shifted to it too, nervousness making her legs shake as she began to drift toward Anna, who may have been trying to lead her to something perverted, but at least she was someone she still knew.

The stillness was broken by a cock pushing through the hole. A very well endowed one, that made Anna's eyebrows perk up even as she clasped her hand over Lissa's mouth, silencing the surprised yell that was about to follow before she could let it out. Everything grew still then, with Lissa staring in greater, deepening worry toward Anna, not sure what to make of what was happening to her as she looked for guidance but only received a wry smirk.

"You have to keep quiet," Anna whispered, keeping one hand over Lissa's mouth as the other hand drifted toward the cock. Anna gripped the impressive shaft confidently and began to stroke it with slow, graceful motions, taking her time with it. "Anyone on the other side might recognize the voice of their princess, and what a scandal it would be if anyone knew that the princess was at a glory hole, sucking a commoner's cock. Wouldn't it be?"

Lissa nodded, eyes drifting back and forth toward Anna's smile and Anna's stroking of the meaty dick pushing through the wall, which made her legs shake for all different reasons as she looked at it. It was impressive, a little bit intimidating actually, but it still made her feel things she wasn't expecting to feel.

"Besides, part of the fun is not knowing who's on the other side. So keep the mystery, Lissa, and don't say a word." Faster Anna stroked, dropping down to her knees before long and sinking into position, a purr rumbling up through her as she leaned in to begin licking at the head. "You can just watch me if you'd like, it's okay. I just need your approval, so stay right there and watch me enjoy this big, hot cock all to myself." Anna was playing too many games at once here, but excitement got the better of her, hand jerking the cock off quickly as she brought her tongue in broad strokes all along the shaft, a bit out of control as she got to work and immediately felt the pleasure building within her, a bubbling thrill she needed to chase harder.

Conflicted and confused, Lissa watched Anna lick all over the cock, feeling a shivering, damp heat building inside of her, fingers tightening at her dress, fretting with it as she wondered what to do and how to handle this. It was a frustration that didn't take long to spiral out of control as she pulled her dress up high and sank a hand down into her panties, stifling some whines as she watched Anna licking all over the dick, surprised and excited all at once by what she saw. She blamed the cock most of all; it was just so impressive and exciting that she couldn't hold it back. Lissa needed to touch herself and embrace the strange sensations bubbling up within.

Anna saw Lissa moving out the corner of her eye, excited and delighted to see the princess hard at work as she leaned forward and sucked it into her mouth a little bit. With eyes on her, Anna felt a bit of pressure to perform more than she might have if it were just her at the glory hole alone. She sucked the cock in, hearing the faint groaning from the other end of the wall and not letting it register as anything too important as she pushed forward, easing into position and welcoming the chance to get down to business when it came to working this lucky man over. Steady bobs back and forth of her eager head sucked the cock down deeper, hand working progressively lower and with more shallow strokes as she sucked down as much as she could. If Lissa knew this cock was a big one, then Lissa would also get to know that Anna could handle every throbbing inch of it.

And she did. Her eyes wide and her lip trembling, Lissa wished she could compliment Anna on her amazing, confident treatment of the dick, amazed to see her work and so happy she got the opportunity to. It was impressive, and she wished she could go as far as to say as much, wished she could push through just a little more and open up like that, but she knew she had to stay quiet, and had too much else to worry about as soft little gasps threatened to reveal her. She could have just stopped fingering herself instead, could have let herself be and been safe, but she was too turned on to stop, almost too deep into fingerfucking herself right in front of a fellow Shepherd that she didn't even think to pull back for her own sake.

Which was precisely how Anna wanted her princess. Aggressively she kept up the pace, sucking and moaning around the cock as she worked her head back and forth, eager and confident about what she was doing and her ability to handle the dick like a pro. Nothing was going to slow her down now as she worked tirelessly at his cock, even taking him down into her throat. She choked a bit on the cock, eyes rolling back in a brief flash of ecstasy as she did so, her head spinning a little bit as she indulged just a tiny bit more into what she was feeling and the raw thrills that came with it. This was precisely where she wanted to be and what she wanted to do with her time.

And what great a time it was! Gagging on the cock, shamelessly corrupting the princess, rocking back and forth and making the most of her budding new business, Anna was having the time of her life, aggressively bobbing along and showing her shameless thrills, sucking on the fat dick without question or hesitation. This was the most primal, indulgent core of what the fun she could have here amounted to, and as she sucked she almost got too caught up in it all, too excited by the raw potential of a glory hole and the good things they could do for her.

In the midst of her heat and confusion, she almost didn't notice Lissa sinking down to her knees beside her, fixated and awestruck, continuing to finger herself as she watched with wide eyes. But Anna could tell what she wanted, what she was too nervous to ask out loud, and even if sucking on the cock was an absolute dream, she was happy to oblige and let Lissa take over. "Do you want to suck him off too?" she asked with the faintest whisper she could, receiving slow nods in response, and she happily shifted over to the side. "Put both hands into it. I've got you."

Lissa was a little reluctant to pull the hand from her panties, where she had faced precisely zero reluctance at all in wanting to lean forward and have her turn sucking some stranger's dick. The realization made her dizzy, but she did as she was guided to do, following Anna's example and grasping the cock with both hands. She stroked it, a bit clumsy, a bit nervous, and it showed in her approach, but she received a groan from the other side of the wall regardless, cheeks burning up as she leaned forward to give some experimental licks along the shaft, having no idea what she was doing or where it all was going to go, but she was eager to find out.

"Mm, that's it, start with the licks," Anna whispered, right up in her ear and patient as she pulled some hair from in front of Lissa's face, caressing and gently urging her on. Everything was going according to plan, and she was happy to play along with the princess, to show her firsthand what fun a glory hole could be. A hands-on approach was the key, and Anna knew Lissa would never have agreed to it if directly asked, but the route of temptation was a potent one, and she had done her job perfectly. "Just let your tongue run all over the cock, learn all about it."

Doing as she was told, Lissa felt like she was growing closer to Anna through this strange and slightly perverse fun. It was something that ignited within her the strangest of sensations, but an undeniable kind of satisfaction ached through her in the process. She was having so much fun doing this, licking her way down the shaft, peppering it with occasional kisses for good measure and lavishing the cock with all the love she could give it. Lissa had never done anything as crazy as this before, sucking a random dick through a hole in the wall, but it felt so good that she couldn't help but keep going, finding out with each bob of her head just how much fun this could really be.

"Now open your mouth and suck on it. You don't need to get it all the way down, and it's not cheating if you use your hands to deal with the rest. Pace yourself, dear." She ran kisses up and down Lissa's cheek as she watched the princess open up and follow her instructions, the redhead unable to hold back a moan as she watched it all go down. She could tell Lissa wasn't a virgin by the way she moved like she had some idea what to do, but she was still clearly out of her depth, and Anna just adored that. "Good girl. Now just keep your mouth on it, for your own safety."

It was an ominous remark that nearly gave Lissa pause, making her stiffen up in worry, but before she could question it, a hand pushed down her panties, and Anna's fingers sank into her needy, even wetter than before twat. She moaned in surprise, but now the cock muffled her, and she was safe to suck without causing any problems, whining and nodding as she pushed forward and gave the dick what it wanted. Steady back and forth motions eased along the cock as she gave the head a nice, thorough sucking, surprised it was coming so easily to her but delighted to feel that it was. She moaned, closing her eyes and sinking down into blissful relief as she gave the dick what it deserved, so happy to feel these sensations almost liberating her.

With fingers pumping in and out of her, the motion was almost instinctual for Lissa, who squirmed and fidgeted, stroking the cock with one hand while her head tried to get down as much as she could, her mouth filling with the thick, throbbing dick and setting her taste buds alight. She was eager to follow through, and did her best to take down as much as she felt comfortable handling. No way it was going in deep enough for her to try deepthroating it, but what she had going here was plenty fine for her.

And for the man on the other side, if his groans were any indication. Lissa could hear the rumbling excitement, the steady, strained sounds of a man enjoying her mouth and her hand. It was enough to make her chest puff out with confidence as she kept up her pace, loving the fact that this was all going so well and that she was able to indulge like this without any worry or fear of upsetting someone. And the fingers inside of her were making this all really rewarding, too! She was thankful for Anna and for the way she took charge, deft fingers lovingly pumping into her and making her shiver with glee, loving everything about this moment and about the pleasure that refused to ease up on her. This was so good that she could barely think straight, and that kept her happily moving along, confident in the knowledge this was all going to come together.

It did, and with perfect synchronicity. Hands thudded onto the wall from the other side as the man gave up to the pleasure, the cock suddenly throbbing within Lissa's mouth and gushing a thick shot of cum. She gasped in surprise, shuddering and holding in tight as she let the spunk fill up her mouth. It was strong, thick, salty, and tasted oddly good, Lissa not sure what to even do with it, and as the fingers brought her over the edge and she gushed all over Anna's hand she didn't even know where to begin thinking about it, just keeping her mouth around the dick above all else to avoid her orgasmic cries tipping anyone off to who she was; her identity had to remain the best kept secret of all.

Finally, the cock withdrew, slowly starting to soften as he left with a content groan, and Lissa waited until she heard a door close on the other side to do anything, frozen and panting, with a mouth still full of cum as she looked at Anna. The merchant threw her mouth forward and kissed Lissa, tongue pushing invasively into her mouth and licking up at the cum she found there, a moaning and excitable mess happily giving in to the chance for illicit thrills as she made out with her. The cum was swapped back and forth as the two shared a moment of sorts. A moment that made Lissa squirm and wriggle, happy and excited, the tingling afterglow of her orgasm leaving her feeling radiant all over.

"What did you think?" Anna asked as she finally pulled back. "Did you enjoy it?"

"I loved it!" Lissa gasped, squealing with excitement. "I'm sorry that I doubted you, Anna. That felt so good, I loved every second of it. You have my approval now, I promise! You only need Chrom's now, right?"

Anna smiled a twisted, bright smirk, eyes shifting over to the hole a moment and purring, "Actually, I think I already have his approval." She didn't reveal the cards she held as she leaned in to kiss Lissa again, piercing through the confusion of her vague remark with affection, burying her implication under the logic that Lissa didn't really need to know. "But that's not important right now; why don't we share the next cock to push through?"

A chipper, excited, eager chirp of "I'd love to!" had Lissa blushing brightly, only for a bell to ring out in the distance and her to place a hand over her mouth in surprise. This was a blast, and Lissa wanted to come back here so much more often, but she was going to need to get better at this whole keeping quiet thing.

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