Through The Watching Glass

My One Hundredth Literotica Story

(excluding the eleven written as

RolloJTomasi

😊

)

🎭 🎭 🎭

This story is my contribution to the:

2024 Literotica Nude Day Competition

🎭 🎭 🎭

Edward held his breath as the curtain between the two rooms slowly moved upwards. The intervening glass panel ran from both wall to wall and floor to ceiling, and the first thing he saw was one beautifully pedicured foot, with scarlet nail polish. The woman in the other room was clearly seated, just like Edward, but with her legs crossed. As the blind slowly receded further, a shapely calf was revealed, and then the other foot. Edward adjusted his mask nervously, and was very conscious of both his own nudity, and the intense throbbing between his legs.

The curtain continued to rise. Now legs, one over the other, as he had surmised. Then a narrow waist, and taut abdomen, punctured by a deep navel. Her skin was alabaster, with a handful of birthmarks merely serving to emphasize how otherwise flawless it was. Edward was dimly aware of an electric motor whirring. He realized that his own abdomen was now most likely fully exposed to the woman, and hoped that she approved, he certainly couldn't be any harder at this point.

The woman was leaning back, looking relaxed. Woman? The profile had said her name was Angel Lover, and that she was twenty-five. Then Edward's username was Brad84, so he didn't put much store in the veracity of her details. He guessed that Angel would have to do. From what he had seen so far, the name was an apt one.

The speed of the curtain's ascent was glacial. All part of the tease. Angel's arms now appeared, crossed below her breasts, which came into view next. They were tiny, even when pushed up slightly by her arms. Tiny and perfect, with stiff, protuberant nipples. The matching algorithm was spot on. Aware that Angel could see, and hoping she viewed it as a compliment, Edward gripped himself and couldn't resist commencing an up and down motion, his excitement was just too much to bear.

The curtain continued upwards, and now traces of chestnut hair, trailing over her shoulders. Then finally Angel's face, or as much of it as was not hidden by her mask. The covering was more Venetian Carnival than superhero, black, lacy, and relatively revealing. Angel's coffee colored eyes sparkled through the two holes, and the symmetry of her features was very evident.

Angel's line of sight was also obvious, and a faint smile crossed her lips. Pleased at this response, Edward moved his knees further apart and somewhat nervously displayed himself, still stroking slowly. Angel blew him an encouraging kiss, unfurled her arms and legs, and mimicked his spreading.

She was immaculately waxed, obviously recently, and with not even a hint of stubble. A trimmed, dark brown triangle hung above her vulva, pointing down to where treasure lay. Angel slowly ran her hands down her abdomen, her long red nails dragging against her skin. Down to between her legs. She pulled her flesh outwards, her sticky lips parting, her opening creamy, slick, and inviting. Edward gasped and squeezed himself hard. Three quick strokes had him twitching, and then he slowed, not wanting to end his arousal so quickly, desperate to extend and savor the moment.

This was Edward's third session at the club, so his trepidation was less than it had been on the first, or even second time. But this was balanced by his excitement about how closely Angel matched his ideal type. You provided detailed feedback after sessions, there was a form in the app, and the algorithm was meant to learn your preferences. The waiver he had signed also allowed the AI to use the multi-angle video that was part of the membership package to assess what worked and what didn't for people. Edward doubted that the software could improve on Angel, he rather wished that there wasn't a one-time only rule in force. It was designed to protect members, to preserve anonymity. But still, he'd be very happy to meet Angel again.

But these thoughts were pushed to one side as Angel dipped a nail into her soft wetness and eased her finger inside up to the first joint. Edward felt the blood surge into him and he increased the frequency of his hand movements, stopping only when the tingling built too much. Angel seemed more than aware of the effect she was having on him. With a broader smile, she held up her glistening digit and then slowly licked it clean.

Edward whimpered softly, and allowed himself two firm strokes. His own fluid was now dripping down and making his hand slimy. Edward stared into Angel's eyes, feeling lost, feeling how much he wanted to be on the other side of the glass with her. He also began to wonder about her. Who was she? Why had she joined the club? Was she as in to this as he was?

The club itself was, as far as Edward could tell, unique. There were places where you could pay to watch a naked sex worker, and even also have her watch you. But this was different. You took out an annual membership, filled out a lengthy questionnaire, and the AI provided you with a list of potentially matching members, ranked by what it viewed as compatibility. A thought crossed Edward's mind, what was it about him that had lined up with Angel's preferences?

Angel seemed to notice Edward's lack of focus. She got off of her chair, and approached the dividing glass. When close to it, she turned away, stood with her legs a foot apart, and slowly bent until her torso was horizontal.

She thrust out her ass, and it was a sight. Angel wiggled her legs and the vibrations resonated in her rubbery butt cheeks, the ripples testimony to the elasticity of youthful flesh. And below her buxom butt, Angel's padded pussy lips peeked out, wet with her secretions, almost begging to be fucked.

Exhibiting great balance, Angel reached back and put a hand on either cheek. First she squeezed, kneading her pliant flesh. Then she pulled her hands slowly to either side and revealed not her tightest opening, but a hexagonal, amethyst-like jewel, bound by silver, and clearly attached to a plug deep in her ass.

There was no wavering in Edward's attention now. His breathing was fitful, his heart pounded against his ribs, and he stroked himself vigorously. So vigorously that familiar pulses suddenly raced up his shaft. Loosing his grip, Edward tensed and tried desperately to hold back. He almost succeeded, but a bead of milky fluid seeped out, and drizzled down his shaft. Edward exhaled deeply, and the sensations abated. He focused on Angel again, thankful that she had not observed his ejaculatory crisis.

Just at that moment, Angel looked back over her shoulder. The twisting movement must have shifted the elastic holding her mask in place, and it rode up. Very briefly, Edward saw half of Angel's face, before she turned away again. It was at an angle and only for a second, not enough to form any conclusion beyond confirming what he already knew, she was very pretty.

Angel adjusted her mask and turned round again, a sheepish look on her face, something that was a little incongruous while presenting her plugged ass. Edward smiled reassuringly, and mouthed, "it's OK, no problem."

A look of relief crossed Angel's face, followed by a smile. Returning to sit on her chair, she spread her legs, and gave Edward the universal mime for a guy jerking off, a questioning look on her features. Edward nodded and took hold of himself. Looking at the clock on the wall, he saw they had fifteen minutes left. This was going to be it. The build up had been fantastic, now he yearned for release.

Angel was a flexible young woman. She lifted her legs and bent them, placing her heels on the front of her seat. Then she let her knees collapse sideways, opening herself to Edward. The purple jewel sparkled a little below her equally glistening interior pinkness. After blowing him another kiss, it was show time. Angel lay back against the rear of her chair and, pulling on one bullet nipple, began to massage her clit.

No sound reached Edward, but he could see that Angel was getting excited quickly, probably moaning. She closed her eyes and rubbed harder and faster. Edward began to jerk, stoking his own fires, but still wanting to synchronize with his session partner.

Angel's face was now turned to the ceiling, her mouth open, obviously panting. Edward thought that she was moving quickly to a crescendo. He assumed that the meeting had been as much of a turn on for her as it had for him, so rapid was the escalation of her emotions.

Edward also began to feel electricity run through him, muscles tensing, preparing to tense harder. He slowed his rhythm, trying to keep pace with Angel. She relinquished her nipple and rammed -- there was no other word for it -- two digits into her now soaking wet opening. She fingered herself hard and flicked the digits of her other hand rapidly across her clitoris.

Edward judged that she was close. He was close too. He knew this was going to be big, but one thing was missing to make it perfect. As if on cue, Angel raised her head and opened her eyes. There was almost a look of panic on her masked face, as if she was overwhelmed by the inferno raging higher and higher inside her, as if she couldn't cope with the sensations rushing through her body.

Their eyes locked, and, as Angel thumped her fingers into her pussy, and stimulated her clit, she mouthed, "cum for me, please."

Edward needed no second invitation, jerking himself with long, fast strokes. Soon he passed the point of no return, and pulled down hard, his head an engorged shade of purple. As the first wave thundered up his shaft, and a jet of translucent liquid arced up from the tip to splash on his stomach, Angel clearly began to scream. She pulled her fingers out and sprayed clear fluid so hard that some droplets made it to the glass pane and began to drip downwards.

Edward was pumping jet after jet, his volume and duration way above normal. And he was delighted to see Angel licking her lips, obviously savoring how he was painting his own body sticky white.

And then a buzzer sounded, and the curtain began to descend, much more rapidly than it had ascended. Edward and Angel had shared so much, and now there was only time for each to blow a kiss, and mouth a, "thank you," before they were both alone again.

Getting his breath back, Edward had one thought. How could he meet with Angel again? It was strictly against the rules, of course.

There was a shower at the rear of his room, and Edward went to wash, knowing that the exit door would not unlock until Angel had already left in one of the cars that took members to and from the club. If any people actually worked at the establishment, they were never seen. The app opened doors, told you which room to go to. Nothing was ever done in person.

The location was also secret. The limos dropped you off and picked you up at the same underground garage, which could have been anywhere. Their rear windows were blacked out, and the front ones heavily tinted, you could see neither landmarks en route, nor even your driver. The club took anonymity and security very seriously.

Edward found his phone, fired up the club app and got a 'Welcome back, Brad84... your videos are being processed and will be available shortly.'

He opened a chat session and the bot asked how it could help. Edward said, "speak to agent." Within ten seconds a silky female voice said, "how may I help, sir?"

Edward said that he understood that multiple meetings weren't allowed, but wondered whether there were ever any exceptions made. He knew the answer before the woman said, "no exceptions, sir, and any attempt to contact other members is likely to result in expulsion from the club, may I help you with anything else?"

Edward said, "no," and got dressed. In the car, his phone beeped and he woke the screen. He had a message waiting, probably about the videos being ready. Well at least that was something. He clicked on the screen.

Hi, Edward. It's Angel here. I want to do that again. I'll be in touch 💋💋💋

Edward? How did she...? What the fuck?

🎭 🎭 🎭

Edward's tryst with Angel had been on Sunday evening. He struggled to sleep that night, tossing and turning, checking his phone for any new messages, wondering what Angel contacting him had meant -- if it was indeed her -- and how she had known his name. There were no answers to these questions and, eventually, he fell into a light and troubled sleep.

The alarm seemed like it went off way too early, and Edward felt like death. Still, he had meetings later and there was no alternative to getting up. In the shower, images of Angel's body flitted across his mind. But the arousal his memories caused was tempered by questions, concerns even. In an Uber, on his way into work, Edward again checked the club app for any messages. He also noticed that Angel's initial one had disappeared. He almost thought that he had imagined the whole thing.

At 7:30, Edward was at his desk, surrounded by monitors. London had been up for hours and the bond market was on the move. Movement, regardless of direction, meant opportunity. As he studied news wires and quantitative reports, his screen froze, then went black. This had happened before, IT were meant to be fixing it. Using a functioning monitor, he pulled up the ticket and wrote a less than complimentary addendum to it.

As soon as he had pressed send, Edward regretted it. He was being a pompous asshole, something he had told himself that he wouldn't let happen. He guessed that the Angel thing was getting to him. There was no way to delete his rather offensive message, so instead he added:

Sorry, having a bad day, didn't mean to take it out on you guys 😬

Then Zach was at the door of his office. Edward supposed that they were friends, though maybe not in the most traditional manner. Their conversations were mostly about work, or which of the female employees Zach was currently perving over. The latter made Edward uncomfortable, but -- not least as he knew no one else in New York -- he played along with it.

Zach asked how Edward's weekend had been. Part of him wanted to say that he'd had the most amazing orgasm of his life while mutually masturbating with a woman behind a glass screen. The sensible part said, "you know, quiet, how about you?"

Immediately, Edward wished he hadn't been polite. Zach launched into a story about a sexual conquest, the accuracy of which Edward very much doubted. While he was in mid-flow, there was a knock on the office door, and a woman was standing there. Her attire immediately marked her out as IT support. Nondescript jeans, a hoodie with some anime character on it -- Edward had enjoyed the genre growing up, but no longer had the time -- and the mandatory EarPods inserted.

Her hair was black and cut short and choppily. Her posture was suggestive of wanting to disappear into the background, and, when she spoke, her voice was quiet and her tone unassuming. She didn't bother to introduce herself. "You got a bad monitor?"

"Yeah, this one here. It's been crashing."

"Sure, I'll take a look."

As tech support examined Edward's screen, Zach recommenced his story, not leaving out any salacious details, totally ignoring the woman's presence. Edward hoped that the girl had turned her earphones up, and rather wished that he had some too.

When he eventually finished, Zach said, "gotta run, lunch?"

"Sure," replied Edward, wishing he was strong enough to say he was busy.

The IT girl was bent over the desk looking at the monitor's wiring, and Zach tapped her ass with his hand on his way out. She startled and then got back to tinkering with the monitor.

Once Zach was out of earshot, Edward said, "I'm so sorry, that was totally inappropriate, as was his story."

The woman shrugged. "I get a lot worse. Still gotta pay the bills. The monitor is fucked, I'm going to order you a new one."

She pulled out a phone and started tapping into it. A look of frustration crossed her face, but she seemed to resolve the problem. "OK, all done. Should be a day or two, OK?"

"Yeah... er... thanks, I guess."

She nodded and made to leave, but then stopped. "Did you hurt your hand?"

"This?" Edward touched the port wine stain on the back of his left hand. "No. Had it since I was a child. People tell me it looks like a map of Texas."

"Yeah, kinda does, cool."

Edward's phone beeped and he scrambled to pick it up. "I'm sorry, I need to get this."

The girl shrugged and left. Edward closed his office door, then settled down to read his new message.

Hi again, Edward. How about Wednesday evening? You should have a new match for someone called Sabrina Goode. Make an appointment. See you later 💋💋💋

Edward opened the match page and, sure enough, there was Sabrina, looking very different to Angel. Blonde hair, larger breasts. He went back to check that he hadn't misread the message, but again it had disappeared.

In two minds, he hesitated.

A new message appeared.

Make a choice, cowboy 😊

Cowboy? Edward made a choice, and made the booking.

🎭 🎭 🎭

Edward had been distracted for the rest of Monday, through all of Tuesday, and up to 7pm on Wednesday when the limo picked him up from his apartment. His monitor had been replaced on Tuesday, but it was a black IT guy who had done the work. Edward hoped that Zach had not made the woman too uncomfortable. Then, he thought, he'd not seen her around before. Rather guiltily, he admitted to himself that none of the back office employees had ever really registered with him. Not until now. It suddenly felt strange that he was thinking about this one.

Wednesday evening, as he walked to the club car, Edward noticed, for the first time, that its license plates were blank. Maybe they rotated in some sort of James Bond homage. Sitting secluded in the rear, he wondered how many times he had checked the club app over the last few days, but there had been no further word from Angel.

Now in the room, a different one to last time, but with the same layout, Edward swiftly got undressed, and hung his clothes in a closet, which was cut into a side wall. Naked he sat and waited.

The clock said another five minutes. It seemed that the second hand was moving through molasses. But, eventually, the electric motor whirred and the curtain began to rise. Edward was even harder than before, but also more nervous. He wasn't quite clear what was going on, or why.

And then he saw a foot. Or rather a single white stiletto, and sheer white hose. As the blind moved up, another foot appeared and it became apparent that Angel, or at least he hoped it was Angel, was wearing thigh highs and a garter belt. The skin was the same, the birthmarks at least similar.

As more and more was revealed, other things checked out. The navel looked familiar. But then, larger breasts, filling a white, lacy bra. Edward was confused. And what was this? Wisps of blonde tresses? Was it Sabrina, or Angel?

Then her mask, identical to the previous one, save for being white. And her eyes, Angel's coffee colored eyes, but now framed by very different hair. It was Angel's face. At least Edward was pretty certain. Although the mask was not extensive, it did make definitive identification difficult. Edward reflected that this was kind of the point.

As these thoughts tore through his mind, the woman blew him a kiss, and now he was sure. The gesture was so her. It was Angel, his Angel. Edward was shocked at his use of the possessive, but he felt what he felt. But the differences, what the fuck was going on?