Frustration and Relaxation (Patreon)

Robert's eyes were nearly in the back of his head by this point. The evil nail of his malicious boss swirling sensually around his engorged head felt so overwhelmingly good, but it still wasn't enough to get him over. Instead, each rotation of the naughty digit got him closer and closer to madness. To an orgasm the gorgeous woman was still weighing her options on allowing him to have. All the while the trained masseuse worked her own fingers tirelessly against his nipples.

“NAAAAOOO! PEEAAAHASE! PLEASE! MA’AM PLEASE!” Robert pleaded in sexual agony, but still the sensation’s continued. Neither woman having any care for the young man’s limits.

“Or Robby, just how long do you think we can ‘go around’ like this. You look like a mess. It’s unbecoming.~” the blond woman mocked. Continuing the circling of her nail over and over against his tip. The pre-cum pooling pathetically in the nook of her breasts.

“It’s all part of the process dear.“ The Asian woman behind him tittered. “You’ll feel so much better by the time we’re done. Now be a good boy Robby, or else we’ll get meaner.”

“Yes Robby.<3” The blonde woman mocked again. “Be good for us. Or you’ll find out just how torturous an orgasm can really be. Tickle tickle tickle Robby.~”

——

Robert Lee, a 24 year old aspiring lawyer with a submissive streak that could be seen from space. Especially for his boss Julie, a well established "man-eater" always looking for a new toy to break against her heel. When the shy and oh so cute Robby came into her life looking for an position, it was a match made in hell for the young lad.

The veteran lawyer enjoyed nothing more than bullying her young protégé into blissful submission. Secret pettings during important meetings. Long hours working late kneeling under her desk. Not even mentioning the countless times poor Robby spent stuck inside an elevator with her. Only to come stumbling out floors later covered in kiss marks and left to fix himself.

With all of this though, there was still something to be said with how Julie had outdone herself this November. With it being a “very special month” for “certain kinds of people” his striking female boss was eager to have Robert participate, and didn’t give him much choice in the matter.

“A-a whole month?!” The shy young man gawked. His brown, beautiful eyes were the size of saucers. Surely she had to be joking!

“That’s right Robby. A full month. I’d like you to keep yourself under control for the entirety of November.” She leaned forward, giving him a perfect view of her sizable cleavage. “That wouldn’t be a problem would it?~”

A chill rattled it’s way up the young man’s spine. He knew damn well he couldn’t refuse her. Julie was well skilled in getting what she wanted, especially from submissive men like him. His stomach dropped as the full weight of this challenge weighed down on him.

Still, Julie waited for him to object. Almost daring for him to do so, but he wouldn’t. Poor Robby, doomed to an entire month without a single climax. Her panties grew wet at the thought of it. So help her she was going to make this the most torturous three weeks in the inexperienced young man’s life.

“That wouldn’t be a problem for you, would it Robert?” She asked again, more authority in her tone now. The dominant higher up wanting his verbal consent. She wanted his compliance to his doom to come out from his own mouth.

“Y-yes Ms... Whatever you say...” The protégé pouted. Trapped like a rat for the amusement of the malicious feline sitting in front of him.

———

Staying abstinent for so long was far from an easy task for poor Robert. Each day the dull ache in his balls would get fuller as his unattended lust only built and churned. Threatening to consume him at any moment.

What made it worse was his “challenge” wound up being the talk of the entire office. Nosey female coworkers unable to help themselves but to throw some wood on the fire, teasing and bullying the young man every chance they got.

Lunch breaks, water cooler talks, group meetings. Robby was unable to escape the topic of his darkening balls and raging hard on. How painful it all looked. His world turning into a never ending parade of pronounced tits and asses, dirty talk, and shameless flirting. How unfair it all was, especially with all of them eager to share their own sexual conquests and desires, all while their sorry coworker wasn’t allowed to have any fun for himself.

Day by day Robby’s buttons were pushed, but none did it better then Julie herself. Every late night working with her was like a mixture of heaven and hell. Her body looking amazing, wrapped up in the finest lingerie she could buy while He himself was allowed to wear nothing. Only the bonds keeping him in his seat while the sexy boss sat suggestively on his lap, going over the reports he had spent the day on.

Any behavior seen as unsatisfactory was met with a tempting tickle to his needy cock, or a horrid squeeze to his filling nuts. Julie would practically leave him cross eyed by the time she was willing to let him go.

The poor sub trembled, he begged, he sobbed, but for all of November that cum stayed trapped within him. Much to the delight of not just Julie, but all the women of the office. All of them loving the added spice of a horny young man not being able to do anything about it.

The worst day of all was trying to give Julie the status report she asked for while watching her get railed over her desk by another eager underling. His muttering numbers were drowned out by the shameless moans of his superior, making him repeat himself over and over. To make matters worse, she would repeatably moan his name, each time making Robert’s knees just that much weaker. He was forced again and again to “give it to her” while watching her get just that. By the time the lucky young man was able to take part in the bliss Robert had long so been denied, he had to go ice himself in the bathroom. The memory of his sexy boss’s caramel body gyrating in pleasure teasing him all the way.

———

December 1st came all too fast for Julie, though, she had to assume her underling would tell her different. She was so proud of her pathetic toy, taking all of that teasing for so long? If that wasn’t worth a reward she didn’t know what was.

“Oh Robby. You did so great last month, I’m so very proud..~” Julie purred. Thinking about all the things she would love to do next year to him.

“T-thank you Ma’am...” The protégé muttered, unable to stop his body from shaking. His discomfort not escaping his boss’s eyes.

“Why honey, you look so tense!” Her smile grew. “It’s a good thing I’m giving you the day off. You have a much more important meeting today.”

Robert looked confused as Julie led him out of the building like a trained puppy. He was told nothing about their destination as the cab took him farther and farther from anywhere recognizable. Until they arrived.

It was an extravagant looking parlor. Robert had never seen a place like this in his life, offering all sorts of services, but the one Julie seemed the most interested in was getting a massage.

Being dragged to the front desk Robert was shocked to see that His boss was familiar with the head masseuse of the establishment. Both of them flashing him a knowing smile as they turned around to see what they would be dealing with.

“Well JACKIE, that’s my poor little Robby. November was a hard month for the dear, so I was hoping you would be willing to take care of the poor lad.” Julie motioned to him casually. Referring to his month of sexual anguish as of it was just a rough patch.

Jackie herself was an radiant Asian woman that made the poor young man’s mouth run dry. Her slim body gave way to the most gorgeous ass he has ever seen in his life, an a smile that would make him do backflips. She eyed the frustrated man up and down, almost as if she was analyzing what could be the problem. Suddenly she laughed.

“Ooooh, a ‘hard month’ hun? With you Jules, I’m shocked last month didn’t have the kid end up in the looney bin.” The Asian woman giggled, making the young man blush.

“Mmm, there’s still time for that. What do you say? Could you get us an appointment.” Julie asked again, also laughing.

“Oh without question. Follow me cutie. It’s time to “ring out” all that horrible frustration...~” Jackie teased as she lead him away with Julie behind him. Feeling cornered, he wasn’t given him much choice.

———

Her was demanded to strip for both the eager women’s pleasure once they got to their room. Neither woman would hear any protest as they go things ready. Once Robert slid out of his slacks, his engorged erection pointing straight up at the flirty milfs, resulting in the both of them giggling at his plight.

“You weren’t kidding Julie. He looks as if he’s ready to go off at any minute.” Jacky tittered, lathering up her ready hands with lotion.

“Oops.~” Was the only thing the boss replied. Her tone dripping in mock sympathy.

“Oops is right. Sorry Robby, but I’m not touching you until your tied down nice and tight for me. I’m not getting groped just because you’re one tease away from hosing down the world.” Jackie said matter of factly, pushing the young man on the table with not much effort at all.

“W-what? Really? I-is that really necessary?” Robert baffled.

“If she says that’s how it is, then that’s how it is Robby. Now listen to the woman. You’re not in charge, do you understand?” Julie chastised her underling as she held his wrists in place for the bonds. He could only look up at his goddess as she had him do what was demanded of him.

Before the young man knew it, he was once again helpless. Not just at the mercy of one beautiful older woman, but too. His heart raced as the both of them circled around the massage table like sharks around their pray.

“Poor Robby,” Jackie mocked as she continued to strut around him. Her hands on her slender hips. “All tensed up from going so long without an orgasm.<3”

“Now you have to ask yourself one question, boy.” Julie followed, as she herself started stripping away her alluring suit. Revealing more and more of her perfect skin, until her bare breasts were once more paraded around Robert’s eyes with no way of having them. “Are you going to walk out of here feeling relieved, or will you crawl out begging for mommy?”

“Ma’am p-please! I-I cahahahahahaahaaant!” Before the poor protégé was able to get out any more of his pleas, his nipples were assaulted by Jackie’s talented hands and fingers, while they played and traced around his nubs without mercy.

“Let’s get to work!” Jackie sang in knowing dominance. “Now then. Tell me where you feel the most tension.”

“I think I have a guess..~” Julie cooed, grabbing hold of Robert’s member for herself. Now subjecting him to the never ending tickle torment he would feel as he was bound in her office.

Robert tried his best to keep himself in check, but after November, it was a fools errand. Despite how hard he tried, he would be turned into a moaning wreck at the ends of theses two dominatrix. Begging endlessly for the orgasm he so wanted. Hoping beyond hope for the slightest shred of mercy.

But is given none.

------
Twitter
https://twitter.com/CollaredKid
Shop
https://society6.com/nerve