Riddle Me This

Chapter 1

It was another beautiful day in Fairytale Land. Autumn was beginning to cast its golden glow upon the land, which meant it was time for the village's annual harvest festival. The festival was a week-long affair with an abundance of feasts, celebration, and merry making. The streets were thrumming with energy, the villagers all excitedly planning for the festivities, and Magdalene was caught up in the thrill of it all. She was in charge of the costume booth at the festival, a crowd favorite. Villagers could rent extravagant outfits from the costume booth - anything from royalty to sorcerers to animals - and then prance around the festival with whatever persona they could dream up. Magdalene had hand crafted costumes for the harvest festival for many years, but this was the first time she was in charge of the booth, so she took the responsibility very seriously.

Several weeks had passed since she had lost the riddle game to Jester, and she had dutifully held up her end of the deal by meeting him every week to satisfy their urges. However, with all the flurry of preparing for the festival, Magdalene lost track of time and missed their most recent weekly meeting. When she didn't show, Jester was very disappointed but also curious what caused her absence. A new suitor, perhaps? Jester wouldn't be surprised, Magdalene was incredibly beautiful with the personality to match. Or she could be in danger.. Jester's ego liked to believe that it would take somehing serious to prevent her from coming to him. Since their deal was bound with a magical handshake, Jester could technically use his powers to summon Magdalene to his dungeon without lifting a finger. However, Jester's curiosity got the best of him and he decided to take a little field trip into the village to investigate matters for himself.

Chapter 2

Day one of the harvest festival and everything was going off without a hitch. Magdalene was in her element keeping up with the onrush of villagers coming to her booth for costumes, and loving every second of it. She chuckled with delight as she watched the village's sheep herder set off into the streets in full peacock garb. He was such a quiet and timid man, she never would've nailed him as a peacock guy. But somehow it worked, and that was the magic of the costume booth! A few yards away, pretending to scope out some tonics for sale at a booth nearby, Jester watched Magdalene with amusement. He had arrived into the village that morning and was elated to see there was a festival happening. Jester was always down for a good party, plus it would help him blend in while he looked for Magdalene. It didn't take long for him to find her working away in her booth, and he quickly put two and two together that this was why she had missed their meeting. But now that he was out and about in the village, he decided he might as well have some fun. He whipped up a costume of his own - a wolf, complete with a mask so that Magdalene wouldn't recognize him - and he began plotting his fun for the day.

Chapter 3

"Excuse me, how much for the mermaid?"

Magdalene's back was turned, but at the sound of the customer's voice, she spun and faced the front of the booth. A tall man in a wolf mask stood before her, pointing in the direction of a beautiful mermaid costume on display. Something seemed familiar about the wolf but she couldn't quite put her finger on it. However, she did notice that his costume was very well made, and here she thought she was the best costume maker in town! She figured he must not be from around here. As Magdalene turned to retrieve the mermaid costume, a sudden gust of wind blew through the booth, causing her skirt to blow up around her waist and reveal her lace underclothes for a moment.

"Oh my!" she exclaimed, blushing while she quickly brushed her skirt back down. The wolf politely looked away, pretending like he didn't notice. But behind the mask, Jester was grinning broadly. A brief glimpse of Magdalene's beautiful ass had him lit up. He couldn't wait to see more. Magdalene quickly collected herself as she removed the mermaid costume from its display.

"Great choice! The mermaid is one of my favorites. It's three coppers to rent for the day, or ten for the whole week," Magdalene replied professionally. She eyed Mr. Wolf up and down, appreciating what she could see of his physique. "Are you interested in it for yourself or for someone else? We might have it in your size...". The wolf chuckled and replied,

"It's for a beautiful woman I met recently. I feel this costume would really bring out her best... assets." The wolf growled his reply in a suggestive tone. Magdalene wasn't sure why, but his response made her blush and look down. She wouldn't mind seeing what Mr. Wolf's best assets were.

"In fact," Mr. Wolf continued, "you look very similar in size to this woman. Would you be willing to try it on for me, so I can make sure it's the right choice for her?"

"Well, sure, I don't see why not." Magdalene had never been asked to model a costume before, but she wasn't opposed to it. If it helped her make a sale, it was worth it. And if she was being honest, she had tried on the mermaid costume several times in private, as it was one of her favorites. The tail was a gorgeous tight green skirt that shimmered with her every move, and the top was made of gold fisherman net, designed to stretch tight across her chest with two sea stars strategically placed over her breasts.

"Just give me a few moments while I change!"  Magdalene hurried into the changing room at the back of her booth, drawing the curtain closed behind her. Something about interacting with Mr. Wolf had her feeling flustered, in a good way. She quickly unlaced her dress, letting it drop to the ground and revealing her naked body. Her breasts sprang free and she felt a sexy thrill at knowing Mr. Wolf was just a few feet away from her while she was naked, just one curtain of cloth separating her from view. Little did she know, Jester had quietly maneuvered himself into a position where he could peek at her through a gap in the changing room curtain, and he was thoroughly enjoying the show. His cock had already begun to harden from his limited interactions with Magdalene, especially after being deprived from their weekly meeting, and now seeing her on full display had him throbbing. Magdalene began to don the mermaid costume, so Jester backed away and returned to his spot behind the counter to wait patiently. Moments later, Magdalene swept the curtain aside and sashayed towards the counter.

"Miss mermaid at your service!" she declared with a flare. Jester drooled inside his mask. The mermaid tail fit her hips and thighs just right, and the way those starfish just barely covered her nipples left little to his imagination. He swallowed, taking a moment to collect himself so he could pretend like he was keeping his cool.

"Hmmm.." he mused, as if his erection wasn't about to burst through his pants.

"Can I see the back?" Magdalene complied and gave a slow, seductive spin. She was enjoying the opportunity to show off some of her best work. Jester cleared his throat.

"Yep. That's perfect. I'll take it."

"Wonderful!" Magdalene clapped cheerfully. "I'll get it packaged up for you in no time!"

As she turned to return to the fitting room, Mr. Wolf followed closely behind her, closing the curtain behind them both.

"Why don't you let me help?" he growled seductively. Magdalene began to protest, but at that moment, Jester removed his mask to reveal his true identity. Magdalene gasped.

"Jest-" she began to exclaim, but at the same moment another voice called from the front of the booth, and Jester clapped a hand over her mouth to silence her.

"Magdalene?" someone chimed from behind the counter. "Are you here?" It was the voice of her assistant, Lachlan. Magdalene had sent him out earlier to attract more customers. What was he doing back already?! Magdalene pulled Jester's hand away from her mouth.

"It's my assistant! I have to go out there!" she whispered desperately.

"You can answer him from in here," Jester said evilly. "I'll still help you change."

"Magdalene?!" Lachlan called again. Jester put a finger to his mouth in the "shh" symbol, then moved behind Magdalene while lifting her arms up over her head.

"Hi Lachlan!" Magdalene called out, managing to keep a calm and neutral tone of voice. "I'm back here in the dressing room." Jester had gotten the net top completely off of her and wrapped his arms around her to cup her full breasts in his hands.

"Mmm," he moaned softly in her ear, and began gently rolling her nipples between his thumbs and forefingers. Magdalene's pussy instantly throbbed in response and her breath caught in her throat.

"Oh okay, I'll come chat with you in there!" Lachlan replied cheerfully.

"No!" Magdalene quickly objected. "I - uh - had a split in my dress, so I had to come in here to take it off and repair it in privacy!"

Jester gave another firm pinch to her nipples while she spoke, making it even harder for her to sound normal.

"Ah.. understood," Lachlan's voice sounded a bit embarrassed. "I'll stay out here then."

Jester pulled on Magdalene's nipples harder, causing a soft moan to escape before she could help it. She quickly tried to cover it up with a cough.

"Thanks Lachlan! Why are you back so soon? Is everything okay?" The risk of having Lachlan right outside the dressing room was turning Magdalene on immensely. She could feel her pussy already slick with wetness between her legs. Apparently it had the same effect on Jester, as she could feel him pressing his boner against her from behind. He firmly grabbed her by the waist and began to pull her mermaid skirt down around her hips, revealing that beautiful round ass once again.

"Yeah everything's fine," Lachlan chimed. "I had several villagers ask me for costumes, so I came to gather them!"

"That's great!" Magdalene called out, probably a little too loud, as Jester dipped his fingers deep into her wet pussy. "Help yourself to whichever ones you need!" Jester laughed quietly at her performance, and he began to rub circles over her clit. Magdalene sucked in her breath and arched her back, pressing herself onto Jasper's hand.

"Good girl," he growled in her ear, and began pulling his pants off. He grabbed Magdalene's hand, bringing it to his cock so she could feel how rock hard he had gotten.

"Do you know where the ogre costume is?!" Lachlan called. Magdalene had Jester's cock in her hand and she began jerking it while he continued to rub her clit and brought his other hand back up to one of her nipples. Before she could answer Lachlan, Jester pulled his cock out of her hand, bent her over, and jammed himself deep inside of her pussy. She opened her mouth to scream and he clapped his hand over it once again, quieting her while he stifled his own moan. Once his cock was buried as deep as he could go, his balls pressing against Magdalene's pussy, he held perfectly still, his hands at her hips, not letting her move anywhere. She looked so good bent over, that perfect ass sticking out for him. Magdalene couldn't hold back anymore, she knew the ogre costume was on the shelf in the counter at the front of the booth, but she had to get Lachlan out of there. She pulled Jester's hand away from her mouth and breathlessly called out to Lachlan,

"Actually, I think that one might still be in the storeroom. You know that area where we keep all the extra costumes? It's across the way over by the bakery booth!" Jester began to slowly pull his cock out of her pussy, all the way to the tip, and then very slowly sink it back in. The sensation was enough to drive Magdalene crazy with lust.

"Okay- sounds good!" Lachlan quipped. "I'll go there now! Be back soon for the rest of the costumes!"  And with that, Lachlan exited the booth. Magdalene let out a long exhale. Jester didn't waste any time as he began pumping his cock into her faster and harder.

"Oh my goddddd Jester!!" she moaned quietly, still unable to let loose completely in case any customers walked into the booth. Jester was lost in an ecstatic haze, drunk on how good she felt on him. He pulled his cock out, spinning Magdalene around to face him, and he sat down on the changing room bench.

"Ride me," he demanded. His cock stood at full attention, glistening with her wetness. Magdalene obeyed, quickly straddling Jester as she guided his cock inside her once again.

"What are you doing here?!" she moaned as she began to ride up and down on him, her tits bouncing softly.

"I came to collect my weekly meeting with you," Jester explained plainly. A look of realization, combined with lust, dawned on Magdalene's face.

"Uggghhhh," she moaned with pleasure. "I totally forgot!" Jester firmly grabbed a breast in each hand, guiding one nipple into his mouth, sucking it roughly while he pinched the other. He took her breast out of his mouth only to say,

"I know."

Magdalene arched her back, riding his cock faster as her arousal grew. Jester pressed his hips up, his cock creating a rock hard beam for her to grind on, and he let her ride him exactly how she wanted to. He thoroughly enjoyed seeing her in such ecstasy and he wanted her to cum ASAP. Her breath quickened and she gripped his face to her chest where he continued to hungrily suck and pull on her breasts and nipples, which he had learned always sent her over the edge. Magdalene's hips began to buck in that way that meant she was close. Jester reached one hand around behind her, gripping an ass cheek and spreading her open. The extra sensation did Magdalene in. Immediately her pussy exploded in orgasm, sending shivers throughout her whole body, her nipples hardening more than ever in his mouth.

"Jesus Jester!!!" she quietly exclaimed, her hips bucking softly as the orgasm continued to send waves of pleasure through her, her pussy throbbing on his cock, her wetness spilling down him. Jester allowed a few moments for her to ride it out and enjoy it.

"If you forget again," he muttered softly, "I might not be so understanding." And to demonstrate his abilities, Jester snapped his fingers. The motion created a bizarre sensation in Magdalene's body, and before she knew it, she was involuntarily climbing off his cock and getting onto her knees in front of him. Jester snapped again, releasing the spell. Magdalene looked up at him, and without a word, she took his cock into her mouth. She knew Jester would understand the apology. She took him deep into her mouth right away, tasting her own juices on him.

She loved how he felt in her mouth-- his cock so smooth and perfect. She closed her lips around him, imagining that her throat was a pussy and milking him exactly how she knew he liked it. Jester would've liked to relax and enjoyed the treatment, but he knew that Lachlan would return soon. So instead, he grabbed a handful of hair on each side of Magdalene's head, and held her in place while he began to thrust faster, plunging himself deep into her throat. Magdalene began salivating uncontrollably, drool leaking out around the base of Jester's cock.

Right as she began to gag, Jester could feel himself nearing orgasm. He quickly pulled his cock out of her mouth and pulled her to standing. He grabbed one of her legs up and around his waist, and plunged his cock deep inside her pussy again. She had to bite back a scream yet again, the position causing him to rub on her sensitive g spot. He gripped her tight and fucked her hard and fast, his cock growing to an impossibly hard state as the orgasm approached. Magdalene braced herself, and within moments, Jester was nearly lifting her off the ground and his cock burst inside her pussy. She could feel his hot cum emptying inside of her with every jolt of orgasm, and she wanted every last drop.

"Magdalene? I couldn't find the ogre costume so I'm back. Are you still fixing your dress?" Lachlan's voice came suddenly and unexpectedly from the front of the booth. Still in an orgasmic daze, Magdalene wracked her brain for a response.

"Uh- no! I finished my dress, just helping a customer try something on now!" She quickly gestured for Jester to get his clothes back on while she pulled on her dress and straightened her hair. She emerged from the changing room first, hoping she didn't look like she had just been freshly fucked.

"Oh, here it is!" she said, grabbing the ogre costume from inside the counter. Jester came out from the changing room, his full wolf costume back in place.

"Thanks for showing me that costume," he nodded to Magdalene politely.

"Of course, happy to help!" she replied professionally, as she felt his cum begin to drip down the inside of her thigh.

"Wow, that's a great wolf costume!" Lachlan exclaimed. "Did you make that one, Magdalene?"

"No," Jester interrupted. "This is an original of mine. But I may be back tomorrow to try on another one of these masterpieces." Magdalene could hear the devilish grin in his voice as he said it.

"Always happy to be of service," she replied with a smile. With that, Jester went on his merry way. Until the next meeting...