Following his directions, she continued to scan the room. Watching the crowd of people – both men and women – as he started to work her cunt again in earnest. Everyone’s attention fixed directly on her. Everyone watching as her cunt was fucked and stretched wide open. Derek now used two hands on her. Three fingers plunging in and out of her, faster and faster, while the fingers of his other hand flew back and forth across her clit. His eyes went from her dripping pussy to the glass on the floor and back again as he gauged the distance and the force of the squirt he was prepared to pull out of her body.

She felt her body tense up again as he pleasured her. The spring winding tighter and tighter until that moment of exquisite release! As she came, another arc of squirt jetted up and out of her, this time most of it splashing into the Martini glass positioned on the floor.

Derek murmured, “Good Girl” as his hands ran soothingly up and down her body.

But Jessie didn’t want to be soothed. Her body was on fire now. She craved more sensation. She wanted to suck. She wanted to be fucked. Hard. Something had been unlocked within her and she felt insatiable.

Derek was acutely attuned to her body language, and without her needing to say a word, sensed this need in her. She looked to the side and saw him reach into his bag yet again. She gasped as she saw him pull out a massive, red dildo. It was impossibly thick. She had never been fucked by anything that size before. But, in that moment, she craved it. She wanted to feel her pussy stretched so wide by this giant, silicone cock.

With practiced ease, Derek squirted some lube into the palm of his hand and coated the thick shaft, working the lube from the base up to the bulbous head. He then took his place between her legs and while stroking her engorged clit with the fingers of one hand, he used the other to rub the tip up of the dildo up and down her slit, pushing inward a bit with each stroke.

Jessie felt the thick head start to stretch her as he worked it in, twisting, turning, pushing. She simultaneously grimaced as the cock pushed her to her limits while also moaning in desire. Craving it. Needing all of it inside her.

The thickest portion of the head finally slid into her hole, and Derek started to slowly work its shaft into her. Slowly, in and out. Fucking her. The lube eliminating all friction, leaving Jessie with just the intense sensation of being so incredibly stretched and full. With the cock worked halfway inside her, he paused a moment and ran his fingertips along the edge of her tautly stretched pussy where it met the dildo, tracing circles around and around her aching hole and lips.

With her pussy stretched so tightly, the small, circular birthmark on the inside of her right pussy lip was exposed to view. A unique marker that only he once knew about, now on display for all the Club’s guests. He used his fingertips to spread the lube up and down her lips and around and around her stretched cunt.

He then turned and nodded to one of the masked guests, who walked over and knelt down to join Derek. The man reached forward with his own fingers and traced the edge of her cunt where it met the dildo, admiring the extreme stretching of her tight hole.

One-by-one, the other men came forward, each in turn, and ran their fingers around her stretched pussy, some taking the opportunity to give quick, gentle strokes to her swollen clit.

Derek stood back and watched this procession with a satisfied smile on his face. He walked toward the back of the chair and looked down at Jessie’s face. Her mouth open. Breathing heavily as she watched the men take their turns stroking her. Eventually, the first man that Derek had summoned came back around and knelt between her legs. With a nod of assent from Derek he grasped the end of the dildo with one hand and started working it in and out of her cunt while strumming her hard, swollen, clit with the fingers of his other hand.

The sheer thickness of the cock and how tight it fit her pussy pushed and pulled her body forward and back on the slick, leather chair as he thrust it in and out of her. She had never felt more full as she watched this stranger fuck her with this massive, lifelike cock.

She turned her head back towards Derek and found him now standing close. His erection made a tent in his light woolen trousers just inches now from her face. She knew then that she needed him in her mouth. She needed his cock to suck on. She reached toward his belt to undo it, but he gently pushed her hands back down.

“Take it out using only your mouth, baby. Lips, teeth and tongue. But don’t bite or scratch me or there will be consequences,” he whispered to her.

Jessie leaned to the side and pressed her face into the soft fabric of his trousers, feeling the hardness of his cock through the wool. She nuzzled it back and forth with her nose, aching to have him in her mouth. She had to figure out first how to get his thick cock out from behind all of these barriers.

First, the zipper. Straining her head forward, she extended her tongue and used the tip to lift the metal tab from where it lay flat against the zipper. It stood out straight and she reached forward again and grabbed the tab between her teeth and started pulling the zipper down.

Given the force of the dildo rocking her body forward and back, the tab slipped out of her mouth a couple times, but she eventually got it down. She used her nose to nudge open the fly as she sought out his cock. She inhaled and could smell the musky scent of his cock and it gave her a jolt of motivation.

She reached in with her tongue and felt the hardness of his shaft through the soft cotton of his boxer briefs. She knew that she had to get that thick cock either OVER his waistband or UNDER the leg band. She decided to go with under. She strained her neck to push her mouth further into his crotch. He wasn’t making it any easier on her. It seemed he reveled in standing barely within reach while running his fingers along the back of her scalp and pulling her hair tightly. Each hard pull distracted her while also sending electric shocks directly to her trapped nipples.

She used her tongue to slip under the leg band so she could grab it with her teeth and pull it up. She could feel the tension on the fabric as his hard prick pushed against it. With one last tug his cock sprung free and slapped up against her chin. She pulled back slowly and felt the tip of his cock drag up her chin until it was at her lips. She saw a bead of clear pre-cum dripping from the tip. She quickly caught it on the tip of her tongue and sucked it into her mouth, relishing the salty tang.

She looked up at Derek now and met his piercing blue eyes with her own deep, azure ones. He smiled and nodded, giving her permission to take him fully into her mouth. He cupped her chin and stroked her cheek as her mouth moved back and forth on his cock. It felt so warm, smooth and thick in her mouth.

Her tongue ring slid along the bottom of his shaft adding an extra sensation. She struggled to take his fat cock as deep down her throat as she could, choking and gagging a little with each thrust. It was just what she needed however and she tried to adjust her sucking motion to align with the dildo pumping with urgency in and out of her swollen cunt.

Jessie could see in her peripheral vision many of the guests positioning themselves for the best views. Some enjoying the view of her mouth licking and sucking Derek’s cock, while others more fixated on watching her sore pussy get stretched and fucked.

Derek continued to hold her face and stroke her cheek. He leaned down and whispered his plan to her,

“I think you have one more good squirt in you to top off the glass, baby and complete your challenge.”

He continued,

“And I have a warm, thick load of cum to pump into your mouth. I want us to show everyone how good we are together. The last part of the challenge is that we will cum at the same time. Can you do that baby? One, hard, last orgasm and squirt as my cum shoots down your throat?”

Jessie didn’t bother to take her mouth off of Derek’s cock to respond. She was too deep in the throes of her sexual hunger. Wanting more. Needing every hole to be filled. With her mouth wrapped around his cock she simply looked up at him and signaled her assent with her eyes.

Derek smiled down at her as his hands grasped her head more firmly to guide her mouth back and forth on his cock.

“Swirl your tongue around the head please,” he directed.

“I want to feel that metal stud circle and circle the head of my cock. Fuck that feels good. I’m going to guide us now baby and tell you exactly when I want you to cum hard for me. We will milk that g-spot and get every last bit of squirt out of you and into the glass. But to pass this challenge, you need to make me cum at the same time. You need to work your mouth, lips and tongue on me well enough that I fill your mouth with my hot, white cum. Are you ready baby?”

In lieu of an answer, and as directed, Jessie swirled her tongue around the head of his hard cock. At the same time, she felt the thick, veiny dildo plunge harder, faster, deeper into her cunt. She applied amazing powers of concentration to please his cock, to pull his cum out of him and into her hungry mouth, while at the same time focusing on letting her own orgasm build. She could feel the ridged corona of the head pulling, tugging sensuously at her g-spot while a set of strange fingers rubbed quickly back and forth over her aching, swollen clit.

She heard Derek speak,

“Good girl, keep sucking. Keep the pressure with your lips. Oh Fuck baby. That feels so good. Suck my cock just like that. Mmmmmm. Just like that.”

Jessie sucked. She used her mouth, lips and tongue with longing and urgency. Hungry for the ribbons of hot cum to spurt into her mouth

“Get ready baby. Its time. I’m so close. Mmmmm. Now, baby. Cum for me. Fucking cum for me!!!”

Jessie felt Derek’s cock spasm between her lips as rope after silky rope of his hot cum filled her mouth. She swallowed and swallowed but it was overwhelming in its volume. The excess dripping from the corners of her mouth and down onto the hardwood floor. His hands held her face steady as he emptied himself into her.

At the same time she felt the dildo pump deeply into her one last time before being yanked quickly out, fingertips whipping back and forth across her clit. Her own orgasm now ripping through her body and her pussy exploding with squirt.

Warm fluid jetted out of her cunt with enough force to reach and top off the glass. The intensity of the orgasm caused her body to jerk on the chair as she lost control of her body. Her jaw muscles twitched as well and with alarm, she felt her teeth drag across his shaft as he pulled his cock out of her mouth.

“No, no, no!” she screamed in her head. “Oh Fuck. What did I do?”

The room was quiet. All eyes went from the full martini glass on the floor, to the sight of Derek, holding his cock in his hand, examining the red, scrape marks on the top and underside of his shaft. He shook his head ruefully and said,

“I’m sorry baby. You came so close to passing this challenge. But rules are rules. It wouldn’t be right to break them now, would it?”

Jessie’s mind whirled in a panic, wondering what new punishment she would face as two of the guests released her leg restraints and helped her shakily to her feet. A female guest brought her a cold glass of water which she drank down eagerly, not realizing how dehydrated she was becoming.

Jessie watched as Derek and two of the male guests lifted the stuffed, leather chair and turned it upside down, the back of the chair now forming a softly sloping wedge. Derek took her by the hand and had her lay on her stomach across the back of the chair, the wedge propping her ass high up into the air. Her legs were spread once more and secured to the corners. This time, her arms were pulled out in front of her and secured to the front of the chair. She was immobilized now. Ready for her punishment.

(To be continued.....)