Derek turned to the crowd and spoke again,

“It’s time now to finish her punishment so we can move on to the next challenge. “She” has a beautiful pussy, but it is only truly perfect when it is completely swollen and leaking cum. Let’s see what we can do to help her with that.”

He knelt in front of her, brought his mouth to her pussy and used the tip of his tongue to lick a straight line directly up between her puffy, pink lips. He found her clit and sucked it in and out of his mouth a few times before leaning back again.

He looked Jessie in the eyes and said softly,

“We need to spank your pussy now. That is your punishment. You get 20 spanks with the crop, and if you can keep from making a sound, that is all you’ll get. If you yelp, cry or moan, you’ll need to have 20 more. Do you understand, baby?”

Jessie nodded. What choice did she have at this point? She braced herself for what was to come and vowed to herself to keep quiet and still.

Holding the crop in the middle for better control he brought the flat leather square down on her swollen pussy lips.

Tap, Tap, Tap, Tap. SLAP.

The strength of the fifth spank caught her off-guard and she bit her lip to keep from crying out.

Derek paused for a moment to let her figure out this pattern and how to prepare herself. He resumed with the second set.

Tap, Tap, Tap, SLAP, SLAP.

“Fuck,” she screamed to herself, “He’s increasing the number of hard slaps with each set!!!!

He paused again to let this new reality sink in. A moment later he continued with two quick taps,

Tap, Tap, followed by a hard SLAP with the crop.

She stifled a yelp and breathed heavily for a moment. Five, long seconds passed before the next SLAP. Ten more agonizingly long seconds before the final SLAP of this set. Jessie was panting and squirming in the leather chair.

Derek stood up, leaned forward and gave her a long, deep kiss. His tongue softly exploring her mouth. He cupped her cheek and said,

“Just one more set baby. You are doing great.”

He then bent down to admire his handiwork. He ran his fingertips gently up and down her puffy, red lips. They were even more swollen now and sensitive to the touch. A pool of her juices collected on the leather chair seat underneath her. Derek traced his fingertips lazily through the puddle before bringing them up and softly rubbing the tips of her nipples with the wetness.

Jessie was sweating now and softly panting as she looked down between her spread legs to see him standing between them holding the crop loosely in his hand. Derek knelt and bringing his face down to her swollen, hot pussy, planted gentle kisses on her labia and clit before pursing his lips and blowing a cool stream of soothing air on them. The cool stream felt good and for a brief moment soothed her. He leaned back and his eyes moved up her body to meet her gaze. He nodded and said softly,

“Last set baby.”

Her eyes jumped from his to the black swatch of leather at the end of the crop. She decided then that it was better for her to close her eyes. Go deep within herself to get through this final set without making a sound. She thought she could do it. She closed her eyes, pressed her lips tightly together and waited. A few moments passed and she felt the first gentle tap, letting her know it had begun. She forced herself to breathe and waited for the slaps to begin.

She heard the “whoosh” of air before she felt the stinging SLAP on her swollen cunt.

The sting jolted her body. She was surprised then to feel the cold, wet edge of an ice cube run up and down her lips. Soothing the sting. After a moment, the ice was taken away. She kept her eyes closed and waited.

Whoosh. SLAP. Whoosh. SLAP.

“Godammit!” she screamed in her head.

He surprised her with two in quick succession. Her pussy throbbed. The good news was that there was only one left. She had this.

She kept her eyes closed and waited.

She then felt the cool leather lightly drag up and down her inner thighs. He was making her wait. She focused on the sensations. She focused on the contrast between the light strokes on her skin and her aching, throbbing cunt. The edge of the crop now was drawing lines up her belly, to her tits, where he rubbed the edge back and forth across her hard, clamped nipples. Sweet agony.

She felt his lips again on her neck and then heard him whisper,

“Last one.”

He pulled away and she braced herself. More moments passed in agonizing silence. She could feel her pulse pounding in her nipples and pussy.

One last “whoosh,” louder than the others came ahead of one, last, stinging SLAP.

Jessie bit hard into her lip, nearly drawing blood, but she stayed silent. She passed the test.

She once again felt the cold chill of a wet ice cube running up and down her swollen, puffy lips. Soothing her. Cool water dripped down and ran over her clenched and exposed asshole, making her shiver.

She looked down in time to see Derek slide his hands softly up and down her thighs and bring his face to her pussy and start to gently lick and lap her soreness away.

After several long minutes of oral soothing, his face buried deep in her pussy, he pushed back from her, his face glistening with her juices, stood up and announced to the guests,

“It’s time for her second challenge. 'She' has shown how well she can handle discomfort. Now it’s time for her to show us all how much she enjoys her pleasure. One of her special gifts is that she is an amazing squirter when she cums. 'She' is a joyous fountain. Tonight she will demonstrate for us in all of her messy glory.”

Derek retrieved the Martini glass from the bar and placed it on the floor 3 feet in front of the chair.

“Her next challenge is the direct opposite of the first one. This time, the goal is to fill the glass. It will require some really powerful contractions, so I will need to help her achieve some really powerful orgasms.”

The guests drew close on each side of her as Derek took his place back between her legs. With all their eyes on him they watched as he brought both hands down to her pussy and used his thumbs to stroke upwards gently on the outside of her swollen lips in slow, easy strokes. He then turned his thumbs inward and repeated the movement just inside of her lips. A thin trickle of cum emerged from the bottom of her pussy and started to drip down to her asshole.

Derek then used one hand to pull back the hood of her clit to expose the hard nub underneath and rubbed slow, wet circles while two fingers of his other hand slipped easily into her cunt. Jessie moaned with the sensation of finally being penetrated. Her hips squirmed on the chair. Derek added a third finger and started thrusting faster, twisting his fingers inside her as they plunged in and out, his knuckles stimulating her from the inside.

He continued to finger fuck her while rubbing her clit as Jessie looked at the masked faces on all sides of her. Their eyes fixed on her aching, swollen, pussy being penetrated and her hard, exposed clit being stroked so expertly. As her eyes darted from guest to guest she looked down to see that one of the men had his pants open and his hard cock being stroked by the masked woman next to him. She stroked him while never taking her eyes off of Jessie’s dripping pussy.

Jessie watched the woman’s hand stroking this man’s cock just inches from her face as she felt Derek’s fingers filling her completely. She felt her orgasm building. All of this stimulation – the sights, the sounds, the exposure - was all too much for her. It was then that Derek shifted his fingers, turning them upward to press deeply into her g-spot.

“Holy Fuck,” she screamed out loud.

“Fuck. Fuck. Fuck. Fuck!”

She was gasping now. Her orgasm building and building within her. His fingers digging so deep. Fucking her so hard. All of the eyes, staring at the scene in front of them. Her cunt, so open, swollen and exposed.

Derek moved to the side slightly while his hand and fingers never lost leverage or momentum. His hands and fingers were literally pulling her orgasm from her. Slamming in and out. Pulling. Compelling.

And then it hit her.

An hour of build-up finally being released. Jessie came so fucking hard. Her pussy contracting around his fingers. A spray of squirt arcing up to rain down on the hardwood floor in front of her. Wave after wave pumping out of her. Jessie’s moans turned to deep, guttural groans before becoming scream as her first orgasm overtook her.

“Fuuuuuuuuuuuuuuuuuuckkkkkk!!!!!”

It seemed to go on forever. Jessie lost track of time. Her head fell back on the chair. She struggled for breath as the aftershocks hit, twisting and contorting her body on the leather chair. As her eyes came back into focus she could see Derek standing there, the Martini glass in his hand.

He shook his head sadly and turned the glass upside down.

She had missed.

The crowd murmured their concern and disapproval at her failure to fill the glass.

But Jessie knew something the rest of them didn’t. That she was only getting warmed up. Her body just beginning to fire on all cylinders. Her face was sweaty and her hair hung limply across her forehead, but her pussy was absolutely on fire. It ached for more stimulation. Penetration.

Derek placed the glass on the floor between her legs yet again and took his position between Jessie’s legs. He could see that her cunt was so incredibly swollen now. Her lips turning a deep shade of red as his fingers played in her cunt and speared inside her. He adjusted her hips, aiming them at the glass and then went to work. Derek’s fingers expertly ran through her glistening folds before plunging deeply within her again. His free hand ran up her taut and sweaty stomach and up to her tits. He tugged the chain sharply as he continued to finger fuck her.

Derek noticed that Jessie had her eyes closed with her head tilted back on the chair. He reached up, grabbed her chin and shook it gently, saying,

“No, no, no baby. Open your eyes. You need to watch everything that is happening to you as well as all of our guests reactions.”

She opened her eyes and took in the scene around her. So many masked faces. So many hungry eyes running all over her body. Devouring her. Consuming her. She looked to the left and saw the big cock still being jacked just inches from her face. She could see the pre-cum dripping from the tip of his cock.

In her near-frenzied state she wanted that cock in her mouth. She needed it in her mouth. She wanted nothing more than to have that hard, warm cock sliding back and forth past her lips. She wanted to suck it. Feel her mouth around it as her own pussy was being fingered and fucked. She leaned forward, bringing her mouth mere inches away from this strangers hard, aching cock.

That’s when she felt a hand slide up the back of her head and pull her hair tightly. She then heard Derek whisper in her ear,

“Is this what you want right now baby? To suck his cock while you cum? Or would you rather wait for me? Your choice. I’ll help you either way. There is no wrong answer here.”

Jessie was in such a state of arousal that she could barely process the question. Reaching out to bring this strange man’s cock into her mouth was nearly a reflex. Derek’s voice brought her back to some semblance of reality.

She looked up into Derek’s eyes and said,

“I’ll wait, but please, not too long.”

Derek smiled as he leaned down to kiss her sweetly on the mouth.

“Good choice baby. You won’t regret it,” he replied as his fingers resumed their thrusting into her hot, swollen pussy.

(To be continued)