Working Late- Part 2

This is Part 2 of the story, so if you haven’t yet read “Working Late, Part 1”, you’ll find the story easier to follow if you go back and read it. The story so far: Given a series of envelopes and packages by her Sir, a submissive has gone into her office on a Saturday morning. She has followed the instructions for the first four envelopes and one opened one package, which has found her wearing only her stockings, heels, and a brand new set of elaborate nipple jewelry. She is now preparing to open the fifth envelope.

Her breasts already ached slightly from the unfamiliar weight of the ruby drops hanging from her nipples as she reached for the envelope labeled “Step 5.” What did Sir have planned next for her?

“Tug at the jewelry, feeling how it stretches your nipple. Play with your tits until both your nipples are hard. Take a photo of how nice the jewelry looks on your breasts. Send it to me. Do not remove the jewelry until instructed to do so. Open the envelope labeled ‘Step 6.’”

She sat down into her office chair, grateful for the faux-leather covering. She was so wet now that she knew she would leave a puddle of her juices on the seat. She could wipe it off of leather – but it would be impossible to get the scent out of upholstery.

Leaning back in the seat, she began to play with her breasts, caressing the sensitive flesh, starting with making slow, languid circles around the base. She was already starting to breathe heavily from her excitement, and she could not bear to tease herself for long before she took one ruby-red drop between her fingers and began to gently pull.

Immediately a sharp sensations shot through her nipples, and it felt like it was electrified as the sensation went straight down to her core. She moaned out loud, quite grateful she had the forethought to turn the music on before she started following Sir’s orders. 

It was only the work of a few minutes before her nipples were both hard, encircled in gold wire, which contrasted strongly with the creamy flesh of her breasts. This will make a fantastic photo, she thought as she grabbed her phone, aimed it at her chest, and took another photo. She sent it off to Sir with the caption “Step 5. Thank you, Sir.”

She smiled as she reached for the next envelope, her mind quickly moving off to a state of contented happiness. The ache in her breasts was now a welcome friend, and she took a moment to enjoy how the act of opening the next envelope made the drops pull slightly at her nipples.

There was a moment of hesitation as she read the contents of the Step 6 envelope. “Go to your favorite porn site. Watch ten minutes of porn of your choice, playing with your tits while watching it. Do not touch your cunt. When you finish ten minutes, text me the URL of the video you watched, so I can know what dirty thoughts filled your Slut mind.”

Did he really mean that? He honestly wanted her to watch porn on her office computer? She was fairly certain that the firewall wouldn’t let her do that even if she wanted to. He had to know that. She grabbed her phone, ready to text him. She knew that questioning his instructions would be enough to end the game, but he certainly didn’t want her to get fired, did he?

As her fingers slid across the screen to her texting app, she hesitated, and re-read the note. That was when it occurred to her that the note never told her to use the computer. She had plenty of data on her phone plan.

She smiled as she bounced over to her favorite fetish porn site, and quickly pulled up an old favorite, where a young red-headed woman who resembled what she had looked like a few years earlier was tied up at work, and gang-banged by a group of male co-workers she had insulted earlier. Her pussy was sopping wet by now, and her clit ached with need to be touched, but she knew better than to disobey Sir’s orders, so as she watched the video intently, she kept her free hand on her breasts, tugging at the jewelry periodically.

As the video ended, she noted that the timestamp of that video was 10:07. She couldn’t have gotten much closer to Sir’s intended time if she had tried. As she copied the URL to paste into a text message, she remembered that she had told Sir how much she liked that video. She was certain that he had remembered and chosen the time precisely because of that.

After sending him the URL, she opened the envelope labeled “Step 7”. After a relatively easy request in Step 6, she was a bit nervous about what she might find in the next envelope. She slipped her finger under the edge of the envelope to read the next card… and then breathed a sigh of relief as she read its contents. “You have a small refrigerator in your office, stocked with water. Take out one of the bottles. Excite your nipples with the cold bottle, then take a photo showing them to me, glistening with moisture. Send me the photo, and then drink the bottle of water. Hydration is important.”

Her nipples were still hard, so this wasn’t going to take her long at all. She wheeled her chair across the room to the mini-fridge, and pulled out an icy cold bottle of water. It took only the barest touch of the cold, wet plastic bottle against her breasts to return her nipples to a state of being rock hard, so as soon as she thought they were wet enough from the sweat of the bottle, she took a quick photo and sent it as she proceeded to drain the bottle.

There was a ding from her phone, and she glanced at it to see that Sir had responded to her last photo with a smiling devil emoji. That gave her some pause, but after she tossed the bottle into the trash, she opened the “Step 8” envelope, at which point her smile vanished off her face.

“There were no instructions in ‘Step 6’ or ‘Step 7’ to open the next two envelopes. You disobeyed my orders, and greedy Sluts like you need to be punished. Open the silver foil box. Insert what you find within into your needy ass. Take a photo proving that it is in you in your office chair. Send me the photo. Do not remove this item until instructed to do so. Then, open the envelope labeled ‘Step 9.’”

“I… can’t believe I fell for that…” she said out loud. She glanced at the earlier instructions, and sure enough, Step 6 and Step 7 never directed her to move on to the next envelope. She just assumed… but that was so like him. He was always so precise. She should have known better. His Dedication letter had even told her not to do anything outside of her instructions.

She eyed the silver foil box with trepidation. Cautiously she reached for, almost as if she feared that it might bite her. She opened the foil paper slowly, relatively certain that she knew what would be within. As the paper came away, she saw that it was more or less what she was afraid of. A gleaming silver butt plug was visible in a translucent box that was clearly not the original packaging. There was a shiny red jewel embedded in the base of the plug, and inside the same box there was a bottle of their favorite lube.

“At least he didn’t tell me to shove this in dry,” she said out loud to no one in particular. Although as turned on as she was, she didn’t think she would have a problem lubing it up with her own juices if it called for that.

Sir loved to fuck her ass, and while she had never enjoyed anal before meeting him, she had grown to really appreciate the forcefulness with which he took her that way. She couldn’t come just from anal, but when he let her use a toy at the same time… she shuddered with remembered pleasure.

She looked at the plug with a calculating eye. It was big… but not much wider than Sir himself, and significantly shorter. With lube, it would take a little work to get it in, but it shouldn’t hurt too badly.

“Best to stop delaying,” she said as she opened the box. She slathered the plug with the lube, and then began to spread a liberal amount of the lubricant around her ass. She probed in gently with one finger, feeling the familiar stretch as her anal ring opened itself up to the intruder. After fucking herself with one finger for a few moments, she worked a second finger in, inhaling sharply as her body adjusted to accommodate the probing digits.

Realizing that she was as ready as she would ever be, she took the plug and pressed it against her exposed asshole, gasping for a second as the cold metal touched her. She pushed gently but firmly, and for a moment it felt as though her sphincter would not widen enough to allow the toy within, but then with a sudden “pop” it slid in.

“Ugh…” she groaned as she tried to adjust to the sensation. The cold metal was much less yielding than Sir’s cock was, and she could not help but feel the fullness within her. 

She made her way on to her knees, facing the back of her office chair, and spread her legs wide. She thrust her ass out as she grabbed her phone with one hand and took a picture of the red jewel nestled firmly between the pale cheeks of her ass.

She hit “send” and sat back down gingerly. The plug in her ass and the weights on her nipples made each movement one that was filled with erotic sensation. Some discomfort, yes, absolutely. But she couldn’t remember the last time she was so turned on. She glanced back at the “Step 8” instructions to make sure that she was supposed to proceed, and confirming it was so, she opened the next envelope.

“What does Step 9 have in store for me?” she muttered as she glanced at the note.

“You must be nearly mad with lust by now. Open the gold foil box. Use what you find within to play with yourself. Give yourself as much pleasure as you think you can stand, but do not let yourself cum yet. Take a photo of just your face, expressing how much you want to cum. Send it to me. Do nothing else until I respond to your photo.”

She cocked an inquisitorial eye. What exactly did Sir have in mind? She opened the final package to find a new toy – one of a kind that she had never played with before. It wasn’t a vibrator, but instead had a small circular indention at the top designed to be centered over a woman’s clit where waves of air pressure would create either sucking or blowing sensations.

Each time they had entered an adult toy store, she would eye those toys, but she had never actually told Sir how badly she wanted to try one. It was so like him to notice and remember even without her saying anything.

She hurriedly opened the package, noting that it had already been opened – probably by Sir making sure that it had fresh batteries already inserted. Leaning back in her office chair, she spread her legs, setting her feet on the desk, and positioned the toy directly against her aching clit, and turned it on.

“Oh… God!” she moaned as the toy did its work. The first setting felt like a talented lover sucking right on her clit, and the sensation made her eyes roll back in her head. The hand not holding the toy in place reached up to play with her breasts, taking the ruby red of the jewelry and gently tugging on it, sending delightful pain/pleasure waves over her.

She teased herself in this way for several minutes before she had to stop. She was so close to cumming, anything else would push her over the edge. And as badly as she wanted to, she wanted to be a good Slut and fulfil everything else that Sir had in mind for her.

Dropping the toy to the surface of her desk, she grabbed her phone and set it to take a selfie. She licked her lips, and then on an impulse switched it from photo to video as she recorded a brief message. “Thank you, Sir,” she said. She looked at her image in the photo, seeing how heavily lidded her eyes were with lust, and noting that a few wisps of her strawberry blonde hair had escaped her ponytail and were now plastered to her face with sweat.

She hit “send” and then patiently waited for a response, staring at the remaining three envelopes and the toy. She ached to take the toy and finish herself off, but made herself wait, although one hand idly stroked her wet folds, keeping herself right on the edge.

There was a ding from her phone, and she saw that Sir had sent a response. There was a photo of himself, naked and laying on their bed. His cock was rock hard, glistening with precum. The text read “I have been looking at your photos, and thinking of you. You have pleased me, more than you can know. Open the next envelope now.”

Glowing with lust, pride and pleasure, she ripped the Step 10 envelope open, eager to read its contents. 

“You have a thick black Sharpie on your desk. Turn off the music that I know you turned on in the office to drown out any sounds. Then, use any combination of the toys you found in the packages while fucking yourself with the Sharpie to make yourself cum. Take three photos – one of your pussy after you cum, one of the Sharpie coated in your juices, and one of you licking your own cream off the Sharpie. Send all three photos to me. Then open the envelope labeled ‘Step 11.’”

She paused. He knew. He fucking knew that she would put music on. That insufferable, perfect Master of hers.

Failing to comply was an impossibility at this point, and so she quickly grabbed her mouse to turn off the music playing through her computer as she looked at the Sharpie. It wasn’t quite big enough to be her preferred size for a dildo, but it would do, especially with the clit stimulator buzzing away, and the other erotic sensations that she was already experiencing. Besides that, she was ready to explode.

She grabbed the toy and put it against her clit again, activating it and releasing a low moan as it resumed its assault on her tortured clitoris. Within a minute she could feel her body cresting towards orgasm, and she rode that wave. Just before the orgasm broke over her, she pushed the Sharpie inside her engorged pussy lips. She was so wet that it slid right in, but it pushed her open just enough to add a delicious feeling. She pushed it in deeper, and groaned as it bumped against her g-spot.

One thrust, two, and then as she thrust in a third time, her mouth opened in an involuntary “O” as she felt wave after wave of pleasure shake through her. She was stunned that she wasn’t screaming, but she was so overcome that she couldn’t make a sound. As the pleasure died down, she pulled the toy away from her and slumped down so low in the office chair that she slid right out of it, falling with her bare ass against the ground, an impact which drove the butt plug deeper into her, which sparked a second orgasm to wash over her, leaving her laying on the ground, twitching with pleasure.

After a few moments, she sat back up to her knees, grabbing her phone. She lay back on the floor, legs spread wide to take the first photo, the Sharpie still partially embedded between her pussy lips. She slowly drew it out, the marker now sticky and coated with her cum as she took the second photo. Then, she put the Sharpie to her lips as she licked at it, enjoying the taste of herself almost as much as she did when she sucked her own juices off of Sir’s cock. With her tongue obscenely extended, she took the final photo and sent all three to Sir.

On shaky legs, she stood back up as she reached for the penultimate envelope. It opened easily, and she eagerly read what it contained.

“Replace the Sharpie in the cup on your desk. It will remain there as a reminder of your submission to me, to be seen every day while you work. Do not remove either the butt plug or the jewelry, but get dressed. Put the clit massager in your purse, and all of the opened envelopes and instructions, leaving only the envelope labeled ‘Step 12’ out. Throw away all of the wrapping paper. Stand against your door and take a waist-up selfie, holding the last envelope in your hand. Send the photo to me. Then open the envelope labeled ‘Step 12.’”

This actually scared her. The instructions were easy enough to follow, although she was a little nervous about leaving the Sharpie on her desk where a co-worker might grab it to use, but what she was more scared about was what could Sir have in mind for the final envelope if she was being told to clean up and get dressed?

Mechanically she went through the motions, replacing her clothes, although as tightly as the bra held the jewelry against her nipples, she was tempted to forego it. But the thin cotton of her blouse would make the jewelry apparent to anyone who saw her without a bra, so she slipped it in place. She finished getting dressed, threw away the wrapping paper, and placed everything except for the final envelope back in her purse. Then she walked to her office door, took the final envelope in hand, and sent another selfie to her Sir.

Bracing herself, she opened the final envelope as she stood by the door.

“Get back home, so I can fuck you until you scream. We have dinner plans at 6:30 p.m. and I want use of your body to fulfil all of our sexual desires for at least five hours before then, so don’t delay.”

She grinned wickedly as she looked at her phone. It was only 10:30 in the morning. Even with the twenty minute bus ride, there would be plenty of time.

“Yes, Sir,” she whispered as she let herself out of the office, eager to make it home so she could get back to her favorite job – that of Sir’s Slut. With any luck, there would be plenty of opportunities for her to work very late indeed tonight.

About the Author

Broken Unicorn has been a writer since he was a child, starting off writing decidedly non-erotic stories about superheroes. As he got older, he started writing erotica about superheroes, before eventually discovering his kinky side and writing about people who could live in the real world. He lives in the midwest, and is happy to live in a very full house that includes four humans and two dogs. He can be found under the profile Broken_Unicorn https://fetlife.com/users/8765084