The Inter-office Bet

By Nikki Ruffles

Mike is just getting settled into his life as the in-house sissy, when he crosses paths with Mrs. Winthrop, the Mistress of the secretaries.

***EXCERPT***
Mike practically tripped over himself as he got up to assist Mistress. His hands were trembling as he grasped the zipper at the back of her skirt. Mistress and Mr. York were too enamored with each notice Mike’s excitement. The front of his panties tented out, and a wet spot began to show through as his clitty began to leak. The metal teeth echoed in Mike’s ears as the zipper slowly exposed Mistress’s sheer panties. The back of Mistress’s panties was also embellished with lace. Mike was drooling just being so close to her. He wanted to lick her to taste her flesh and her panties, but he knew she would never allow him to do that.

*** Included Kinks ***

Blackmail, Sissy, Panties, Humiliation, Gang Bangs, Bukkake, Public Nudity, Sexual Slavery, Golden showers

***** Content Warning *****

This book contains explicit sex, language and blackmail. Story contains strong themes and is not recommended for anyone under the age of 18.

• Language: English
• Publisher: RW Publishing
• Release date: Jul 19, 2022
• ISBN: 9781005168544

Book preview

The Inter-office Bet

A Sissy Mike Adventure

By Nikki Ruffles

Digital Edition

Copywrite 2022 Nikki Ruffles

All Rights Reserved.

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Part 1: Catching up

Standing at his door wearing nothing but a pair of three-inch clear stripper heels and a very thick layer of cum Mike took a moment to catch his breath. He should have done it inside, but he knew what was coming next. Bending down to unlock his door, Mike was surprised at how quickly this new indignity became normal. The only copy Mike had of his apartment key was attached to a metal chocker that was sealed around his neck. And since he was only allowed to kneel if he was sucking a cock he would have to bend at the waist and unlock the door. It had taken a full day with an intern following him around spanking Mike every time he knelt. Spreading his legs, he bent down to unlock the door, the cat tail buttplug firmly inserted inside his backside raised into the air.

As the door clicked closed Mike’s brain screamed for a shower, but his body begged for sleep. After taking two steps toward the bathroom his body won the argument. Stumbling to the bed Mike collapsed. Before he could even comprehend the horror that would be his sheets in the morning; Mike was asleep.

His new position as ‘outside’ in-house auditor wasn’t fake, Mike just didn’t audit the books. Every day started the same, he would arrive to work at eight A.M. and would immediately go to Mr. McCormick’s office. What Mike was wearing didn’t really matter, but per the ‘rules’ it was usually club wear, the sluttier the better. Every morning Mike would open the door and Mr. McCormick would sigh, saying ‘again’

Mike would bite his lip and put his hands behind his back before resisting his morning speech, Please Mr. McCormick, please don’t fire me. I know I am really slutty, but I can be a super big help around the office.

How is that? Mr. McCormick would always reply.

Mike’s answer was supposed to change every day, he was supposed to name a sex act he could do to keep morale up. – ‘I can give hand jobs’ – ‘I can give blow jobs’ – ‘I will let each department use me as a bukkake model’

Then Mr. McCormick would get the script back on point, And how will you prove my ROI.

Return on investment was a huge concern of Mr. McCormick’s. Not just about Mike but everything. Every pitch meeting would end with an ROI. With Mike, he would keep it all written down in his logbook. At the end of his training, Mike had been provided a bright, neon pink notebook. It was covered in pictures of cocks and in the center was a naked Mike covered in cum. Each day he would have to fill in the log with what acts he committed, and with who. Every Friday he would take the logbook around to each person and ask if they were satisfied with Mike. If they were, they would give a checkmark and an initial. If they, unhappy it was an X and initials? A few times Mike had so impressed an employee that they would draw a heart instead of a check. For every one hundred hearts, Mike got he was allowed to go shopping.

On those trips, Mike could purchase work clothes that looked sexy instead of slutty. The flip side of that was X’s for every ten X’s Mike would have to go to an adult video store and proposition ten men. If he could provide proof of satisfying ten men, the X’s did not count against him. The proof was provided in the form of a load of cum deposited in Mike’s panties. Since he was given all day Saturday to complete that Task, he had yet to report back with anything but a thoroughly soaked pair of panties. So far it had only happened once.

Today was Friday, but it was different than all the Fridays before. And it all started on…

Part 2: Monday

Mike was standing on stage wearing a big smile and a black vinyl tube as a dress. A normal person would have worn nothing under the strapless dress, but Mike was a sissy slut. Under the dress, he was wearing a pair of white lace panties with a matching shelf bra. The tops of his stockings were below the hem of the ‘dress’ and the suspenders made visible marks as they ran up his legs to his garter belt. The six-inch heels matched the lingerie, not the dress.

Mr. McCormick was making a speech, but Mike wasn’t listening. He didn’t have to, no one cared what he thought or what he said. Mike was watching the crowd, most of the crowd was watching Mr. McCormick, but a few of them were eyeing Mike like they were stalking prey. Those were the men you never wanted to turn your back on. When his name was mentioned, Mike started paying attention again.

So, Sissy Mike here is going to spend the week getting an idea what kind of sex you like. On Friday, HE Mr. McCormick emphasized he heavily. Will present a report on what gets each team off the most. While he is doing that the executive team and I will decide which proposal we are going to use going forward.

A round of applause filled the room, which Mr. McCormick quitted with a wave of his hands. Now, I know you all will be tired of fucking Sissy Mike here, So the winning team will spend the night fucking… Candy Apple.

The crowd went wild, Candy Apple was a rather famous porn star. Mr. McCormick stepped closer to Mike and gave him a hard slap on the ass, hard enough that it almost knocked him over, Now we are at the tail end of this project. Let’s bring it home for the win.

Mike followed Mr. McCormick off stage as two lower-level managers hopped up and started calling out directions. Mr. McCormick squeezed Mike’s ass as he passed him off to Mr. York. York, explain to the sissy here what he needs to know.

And Mr. McCormick was gone, never once making eye contact with Mike. York looked him up and down licking his lips. Letting out a lecherous breath he said, Follow me, whore boy.

Mike followed Mr. York into the elevator, the two were alone and as soon as the doors closed, Mr. York pulled the back of Mike’s dress up. Twisting his fingers into the waistband of Mike’s white lace panties he pulled them up hard, giving Mike a nasty wedgie. The elevator chimed and Mr. York said, Leave that like it is and meet me in my office.

Mike started to step out of the elevator with Mr. York, but a palm to the face stopped him, I think you would be better off crawling, don’t you?

Yes sir, Mike muttered back to him as he dropped to his knees. Crawling through the executive suite Mike could hear the secretaries snickering at him. They had been the object of pent-up sexual tension until Mike had been brought on board. His presence may have made their lives easier, but they still harassed him every chance they got.

When the pointed tow of a leather shoe slipped between his legs and pressed against the front of his lace panties Mike stopped. A stern older voice boomed through the hallway. It was Mrs. Winthrop. She was brutal and insisted Mike call her Mistress, What are you doing up on this floor?

Before Mike could respond she lifted her foot higher, You know I don’t like the executive secretaries to be distracted.

I know Mistress, Mr. York wants me in his office, Mike muttered his mind on the foot pressing against his crotch.

Does he now. She said as she lowered her foot. Stepping to Mike’s side she lowered herself, her knees bending giving him an amazing view up her skirt, her sheer white panties just barely visible. She clipped a leash to Mike’s collar and lead him to Mr. York’s office. The snickering got even louder, but only after Mistress had passed.

When she reached Mr. York’s door, she gave it a firm knock. A gruff and muffled come-in was the only response. Mistress pushed the door open leading me in. Without looking up from his desk, Mr. York said, Good morning MRS. Winthrop.

He put a heavy emphasis on Mrs. With a jerk of my leash Mistress walked me to his desk and perched herself on the edge. Good morning, Mr. York. So, I hear you have business with this sissy today.

Mr. York nodded his head as his eyes scanned up and down Mistress’s body. That business wouldn’t be servicing that magnificent cock of yours now, would it?

Mr. York set his pen down and leaned back in his chair, a nasty grin spreading across his face, Well as it happens it is work-related. Whore boy needs to do some research, and I need to explain how it is to be set up.

Do you think his little mind can wrap itself around such a stiff, Mistress paused twisting her body and thrusting her breast out, concept?

I hadn’t considered that. Mr. York said as he stood and walked around the desk. The bulge in his slacks was quite evident as stepped up to Mistress pressing his crotch into her thigh. And now on top of that, I now seem to have another problem.

That does seem, pressing, Mistress said reaching up to adjust Mr. York’s tie.

I might have to use whore boy’s services after all. Mr. York said leaning in close to Mistress, breathing in her aroma. Mistress's hand slipped down from his tie, sliding between their bodies she squeezed his cock through his pants.

Now why would you use a whore boy, when you have a goddess right here at your disposal, Mistress whispered into Mr. York’s ear.

What would Mr. Winthrop have to say about that? Mr. York responded his lips desperate to touch her neck.

Removing her hand from his throbbing sex, Mistress slowly and gently started to unbutton her blouse. As her hands worked down the line of buttons Mistress’s bra slowly emerged. First, it was the scalloped edge of the cup, and then the sheer white lace that wrapped around each breast was exposed. Mistress pulled the blouse free of her skirt and let it slide off her shoulders and down her arms. Mr. York leaned down drawn in by her exposed flesh, still, whispering Mistress said, Didn’t you hear? I rid myself of Winthrop the younger. I kept the name though. It was better suited to me than that sad little fool.

Mr. York didn’t reply, instead, he sucked on her right breast. Mistress let out a little moan before gently pushing Mr. York back. Standing she snapped her fingers at Mike, Whore boy. Remove my skirt.

Mike practically tripped over himself as he got up to assist Mistress. His hands were trembling as he grasped the zipper at the back of her skirt. Mistress and Mr. York were too enamored with each notice Mike’s excitement. The front of his panties tented out, and a wet spot began to show through as his clitty began to leak. The metal teeth echoed in Mike’s ears as the zipper slowly exposed Mistress’s sheer panties. The back of Mistress’s panties was also embellished with lace. Mike was drooling just being so close to her. He wanted to lick her to taste her flesh and her panties, but he knew she would never allow him to do that.

Taking hold of the waistband of Mistress’s skirt Mike lowered it down slowly, savoring every bit of flesh as it was revealed. When the first lace hints of her thigh-high stockings were revealed, mike sighed like a school gurl at the sight of her first crush. Mike’s hands took the skirt down, but his eyes moved back up to Mistress’s panties. Even the gusset of her panties was sheer, Just as Mike moved to breathe in her aroma, Mr. York pushed him away.

Make sure her clothes don’t get wrinkled whore boy. He snapped at Mike as his hands cupped Mistress’s ass. Turning his attention to her clothes, Mike gathered up her skirt and her blouse. The blouse he hung on a hanger over Mr. York’s suit coat. The skirt he carefully folded and laid on a side table.

Turning back, he found Mr. York had moved behind Mistress. He cupped each breast as he kissed and nibbled at her neck. She moaned as he rolled her nipples between his fingers. Mike bit his lip desperate for his hands to be Mr. York’s

In between moans, Mistress issued another order, Pull my panties down, SISSY.

Mike reached in front of Mistress and started to roll her panties down. A thick red bush of pubic hair was hiding behind the white panties. As the panties moved down the aroma of her sex filled Mike’s nose. Closing his eyes he saved the moment, and then she said something he wasn’t expecting, That is far enough sissy.

Mistress’s panties were rolled just below her sex when Mike stopped and then she said, Now kiss my cunt.

Mike leaned in and gently kissed her mound, once, twice three times, before she pushed him away. Her voice was sharp as she snapped at Mike. Get Master’s cock ready for me.

Stepping back Mr. York gave Mike room to work. Working quickly Mike undid the man’s belt and then unzipped his fly. The presence of a nearly nude Mistress was affecting Mr. York, his cock was bulging out begging to be freed of his black nylon boxer briefs. Mike pulled them down slowly his mouth watering at the sight of the stiff cock. Gently he kissed the tip before taking it into his mouth, swallowing it whole. Mistress put a hand on Mike’s head, and Mike was in heaven. Sliding the cock in and out of his mouth he slobbered all over it getting it nice and wet for Mr. York to pound away at Mistress. Just as he was getting into his role Mistress pulled him away. Nice try whore boy, but that cock is MINE.

Mistress bent over the desk spreading her legs as wide as her rolled-down panties would allow her to. Her sex opened for Mr. York as he stepped to her placing the tip at her opening and pausing. Looking at Mike with a wicked smile he said, What is about to happen her Whore Boy?

His lip quivering Mike said, "You are about to have