Jessie was in the shower. She slowly dragged the blade of the cheap, disposable razor over the last bit of shaving cream remaining along side the lips of her pussy, leaving her mound and lips clean and bare. She ran her hand down and over to feel the slippery smoothness, allowing her middle finger to nestle for a moment between the folds of her pussy before sliding up and briefly circling her hooded clit.

She breathed in sharply as she felt that familiar electric thrill shoot through her and her thoughts turned to Derek and wondering what plans he had in store for her that evening.

She had met him online just a few short weeks ago with the intention to engage in a bit of harmless flirtation. In fact, she first discovered him through the “erotica” – oh, who was she kidding – “dirty stories” - that he posted online. He had a way with words that created the most amazing, sexual images that completely pulled her in to his stories. And these stories made her wet.

She upvoted and commented on one of his stories. He messaged her back. He proceeded to seduce her with his words over the next couple of weeks. They made each other cum multiple times online. It was pretty intense. So when Derek told her that he would be in her city on business, Jessie jumped at the opportunity to meet up with him.

He wouldn’t tell her what he had planned for the evening, but in getting prepared, he asked her to make sure that her pussy was completely shaved. Curiously, he said that, “we prefer it that way.”

At the time, Jessie thought his use of the plural “we” was just a harmless slip, or a reference to men in general, but now she wondered.

She rinsed, stepped out of the shower, dried off and slipped into one of her sexiest, black lace thongs. The fabric in front felt nice, softly cradling her lips, while the smooth string between her cheeks rubbed deliciously against her asshole as she pulled the thong in place.

She put on her matching bra and then shimmied into a sexy, little black dress – the kind that every woman has hanging in her closet for nights like this. She gave herself one, final, check in the mirror and liked what she saw. She felt confident and sexy tonight. Ready for whatever Derek might have planned for them. She hoped she was ready anyway.

Her phone chirped and a text popped up from him reading simply, “I’m out front. Come down.”

She walked downstairs and saw him standing out in front of a waiting Uber. She walked out the door and stopped, taking him in.

They had shared intimacies online and knew so much about each other, but this was the first time they encountered each other IRL. He had a confident air about him and a winning smile which put her at ease.

She walked to him. He placed a hand in the small of her back and pulled her closer. He leaned in and kissed her gently on the mouth before pulling back. With a mischievous (evil?) glint in his eye he asked,

“Are you ready for tonight baby? Ready to experience something new?”

Jessie nodded hesitantly. Her mind spun nervously with the possibilities. In the heat of their online playing, he had pushed her to share many of her deepest, darkest fantasies. Things she had never shared with anyone. She wondered if he remembered them and was preparing to put one in play.

Derek helped her into the car and the driver headed uptown. A short time later they pulled up in front of an unassuming brownstone. She didn’t know this particular street that well but it was clean, well kept and quiet. They got out of the Uber. The driver popped the trunk and Derek walked back to take out a small, gray, roller suitcase.

As he set it down on the curb to extract the handle, Jessie heard the rattle and clink of metal objects inside. She knew that this was no basic overnight bag. Derek then took her by the hand and walked her around to the driver side of the car and turned her around to face him, her back toward the driver. He placed his hands on her hips and kissed her deeply, passionately. She kissed him back as she put her arms around his shoulders.

After a moment she felt his fingers on her waist start to pull at the fabric of her dress, lifting it up the back of her legs. She broke the kiss to look at him as her hands came down to rest on his.

She shook her head slightly and mouthed the words, “No. Not here.”

He nodded his head slowly to indicate that this is what he wanted and this is what he would do.

Jessie stood stock still as he kept pulling the dress slowly up until it was over her ass and exposing her to the driver who sat there, speechless, no more than two feet away.

She flushed red in embarrassment and buried her face in Derek’s chest as she could feel the Uber driver's eyes running all over her. She felt another wave of embarrassment wash over her when she heard the quiet hum of the window motor as the driver lowered it to give himself a clearer view.

Derek’s hands ran up and down her cheeks. His fingers turned inward and slid along the crack of her ass and then pulled her cheeks apart exposing the thin strand of her thong laying flat against her tight, puckered asshole.

With one finger, he snagged the strap and pulled it aside, fully exposing her asshole to the lascivious view of the driver. In the quiet of the city night she could hear the driver breathing. Almost feel his hot, horny breath on her skin.

To torment her further, Derek slowly ran his fingertip around and around her tight, little asshole. This is what he gave the driver in lieu of a tip, apparently. After what seemed like an eternity, Derek slid her dress back down over her ass.

He took her hand as they walked together up the steps of the brownstone, rolling his gray suitcase with the other. Jessie didn’t dare turn her head to see the driver pull away, for fear of actually having to meet his gaze and for him to see the humiliation in her eyes.

They reached the door and Derek rang the bell. An attractive woman in a red dress opened it and led them inside. Derek told her his name and she reached behind her and retrieved a tan envelope and handed it to him. Inside were two eye masks. They both were Mardi Gras style with elaborate designs.

He placed one of them over her eyes and secured it around her head before affixing his own. He again took her by the hand and led her through another set of doors and into the main party room. Her heart was still racing from the embarrassing scene in front of the Uber driver. She started to nervously think about just what sort of party this was that required the anonymity afforded by these eye masks

Jessie clung closely to Derek’s arm as she surveyed the room. The walls were a dark mahogany. A large LCD screen was mounted on one wall currently playing an ambient loop of swirling colors. There was a bar in the corner complete with a bartender serving drinks. There were about twenty guests in attendance, give or take a few. It was a mix of women and men, all dressed to the nines. All wearing masks just like the two of them wore.

The guests mingled, not paying much attention to the two of them as they made their way to the bar, but Jessie was sure that she caught several men - as well as a few women - surveying her body and shooting her appreciative looks. Derek ordered them both drinks. A pair of martinis which they took with them as they filtered back through the crowd.

Music was playing now and Jessie had to admit to herself that the room and the guests in it had a cool vibe.

It was 11:00 on the dot when Derek gave a quick wave to the bartender who promptly turned the music down, reached under the bar and brought out a wireless microphone and set it on the bar top. Derek picked it up, turned to the room and said,

“Welcome everyone. I’m really happy you all could make it out tonight. I think this is going to be a very memorable evening. For tonight’s experience, we have just one special guest.”

Jessie looked around the room, expecting to see an exotic dancer or some other sex performer emerge from outside the room, but instead, she saw that all eyes were on her now as she held on to Derek’s hand. She suddenly realized that SHE was the one, special, guest tonight.

Derek had brought her here for the group’s sexual entertainment!

She tried to release his hand and move toward the door. This was too much. She had to get out. But Derek held her hand tightly. He then pulled her to him, wrapped his arms around her and whispered,

“You may not realize it yet baby, but you need this. Trust me. I will take good care of you.”

Jessie was conflicted. She had needs, dark ones, deep within her that she didn’t fully understand. But the thought of being exposed and used for the pleasure of these strangers also made her recoil. She was still struggling with this when her thoughts were interrupted as Derek continued to address the room,

“We are here tonight to work on improving her self control as well as her confidence in new surroundings and stressful situations. You all are here to help us. Let’s start!”

And with that, he slid behind her and smoothly unzipped her black dress. He paused a moment to let what was about to happen sink in. She knew that she was about to be stripped naked in front of this room full of strangers. Jessie trembled both in fear and anticipation. He slid the dress off her shoulders and let it drop to the floor leaving her in just panties and a bra.

He reached around from behind her and unsnapped the front hook of the bra between her breasts and let the cups hang there for a moment, supported only by the friction of the fabric against her skin.

Her eyes scanned the room at all the masked faces staring back at her, expectantly, hungrily. She knew there was no turning back once she was exposed to them. She would need to see this through, wherever he leads it.

She felt his hands lift the straps of her bra off of her shoulders and pull it entirely off of her. Her bare breasts and nipples on display now for this crowd of strangers. Derek’s hands slid around from behind and grasped both of her tits and squeezed firmly. His fingertips then closed around her nipples and started to pinch and pull, making them hard and sending electric shocks directly to her pussy. Jessie felt the familiar trickle start to drip down her thigh that signaled her intense arousal.

Derek opened his gray bag, and felt around briefly until he brought out something silver and shiny. It was a pair of nipple clamps, joined together by a long silver chain. The clips were each in the shape of a plus sign within a circle, with four separate tightening bolts designed to trap her nipples tightly in the center as the posts were screwed down. Jessie’s nipples were already hard and aching. She had never worn clips before and a shiver ran through her as Derek placed the first one around her nipple and started to tighten each post in turn.

She stood still with her eyes closed as he tightened it around her hard nub. What started as pleasurable pressure slowly increased until it became an insistent ache. A groan escaped her lips prompting Derek to step back, grab an ice cube out of a nearby glass on the bar and start to rub it around and around the trapped tip, soothing her a bit.

He repeated the process with her other nipple, soothing it as well with the ice cube afterward. He stepped back again to survey his handiwork before testing the hold of the clips by lifting the chain from between her breasts and pulling firmly but gently.

Jessie moaned in a mixture of pleasure and pain as she felt her nipples pulled outward, toward the crowd gathered there to experience her. Derek moved behind her and whispered,

“We’re almost ready baby. Almost ready to properly present you to my friends.”

She felt his hands move to her hips and slowly start to pull her g-string down over her hips and ass. Jessie felt the damp fabric cling briefly to her wet, swollen lips before peeling off stickily as he let it drop to the floor.

She didn’t move. She stood there, frozen, in the stark realization that for the first time in her life she was amidst a crowd of strangers, completely naked, nipples clamped and her pussy visibly aroused. She took a small amount of solace from the anonymity afforded by the eye mask she was wearing. A small amount anyway.

He moved in front of her, lifted his martini glass off the bar and took a sip, his eyes not leaving her body as he swallowed the chilled gin. He reached between her breasts and picked up the middle of the chain. He tugged gently to indicate that she should walk with him. She stepped out of the damp panties laying on the floor and followed him.

It was this simple act of submission that triggered something in her brain. She knew that she was giving herself over to him now. There really was no turning back and the only question in her mind was about how far he would take this – and how much she could take.

(To be continued)