The Tall and Short of It Ch. 02

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Barry blackmails his way into the game.
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Part 2 of the 2 part series

Updated 06/11/2023
Created 12/16/2022
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A couple of weeks of new adventures passed. Both easily slipped in and out of their sexual roles. Rory submitted to the crop when Ronnie felt wicked. The flogger turned him on more and they used it often. The wide-spread stinging warmth made him feel sensual.

They used the internal egg on a walk in a park that enclosed a small lake. Ronnie enjoyed watching him struggling to keep his boner hidden. She ultimately had him masturbate for her, sheltered in a large clump of bushes, as people passed on the walkway.

Rory worked on stretching exercises that led him to being able to autofellate on command. Ronnie would say, 'Suck it, boy.' And he would perform for her. He didn't need the futon anymore. He pushed his biceps under his calves and use his hands to reach around and grab his toes. Using a combination of pulling his legs back and bending forward put his monster member in his mouth. She loved watching his face as he sucked and swallowed a load for her enjoyment.

They were diligent in photographing their fun. Quite a collection was being accumulated. The addition of one of their smart phones on a tripod, coupled with the Canon camera, provided an unobstructed view of all the action. Rory would curate the random pictures and pick the ones admirable of being added to the collection. They played a game of picking the 'Top Ten' sexy shots. Each new batch of action shots were evaluated as to the totally prurient content to determine if they were worthy of replacing one of the existing Top Ten. When one of the new pictures displaced a former top shot, they celebrated by watching each other masturbate.

All workouts at the home gym became naked for him at her insistence. She told him it was 'aesthetically pleasing.' He wore a jock when doing heavy barbell work but enjoyed the freedom nudity afforded the rest of the time. He often stayed hard during his entire workout. She adored watching his 'third leg' wave around wildly.

He cooked and cleaned naked as well. Eventually, he was au naturel most of the time around the house. He gave her back rubs, painted her toenails, and catered to her every need. She loved the attention, and he savored the servitude.

Ronnie traveled more than Rory. She was a Junior Partner and was needed onsite at large clients. She called it 'showing the flag,' making the client feel they were getting special attention. One trip to Detroit was going to last a couple of weeks. The last day before she was scheduled to come home, Rory was missing her and the sex. He decided to take his personal laptop to work. He could look at the collection of pictures, when he wasn't busy.

During the morning, there was a problem with his work computer. He emailed IT about the issue. That also gave him the opportunity to look at the 'New Ideas' folder. He was in between appointments and looking at some of Ronnie and his roleplaying. He was daydreaming, looking at the pictures, when the IT guy walked into his office. Rory slammed his laptop closed like he had been caught looking at porn, which was literally true. With the added problem that he was a featured actor in the smutty pictures.

"I'm sorry, Sir. I thought you were out of the office today."

"My wife is working remotely today... same last name."

"I'm sorry to interrupt you. I can come back later to check out the computer issue."

"No need. I'll just move over to my conference table and work from there. I brought my laptop in today."

"Sir, I need to check something on your personal laptop before I work on the company system."

"Is that really necessary? It contains personal information."

"Yes sir, I do need to check something in the operating system to determine why it works and the company unit does not."

"What? That sounds like techno-speak. Are you sure?"

"I am, sir. But you can stand behind me and watch. It will take me a minute or so and I just need to copy down a very small section of code."

"It's not that I don't trust you, but I am going to watch."

"Absolutely no problem, sir. I understand," he said. He thought, 'That fucker is hiding something interesting.'

Barry, the IT tech was a nineteen-year-old, who looked younger. He graduated from high school and received an AA degree from a local college at the same time, when sixteen-years-old. He had a full academic scholarship to a prestigious university but lost it because of a hacking scandal. Now three years later, he was working tech support and paying his own way at the university. He was slightly shorter than Rory and weighed twenty pounds less.

Rory opened his personal laptop and entered the PIN, while Barry was on the other side of the desk. Then he stood up and allowed Barry access to the computer. He stood behind him and watched as Barry immediately hit the settings button, then 'Network & Internet,' and finally 'Ethernet.' He scrolled down slightly and wrote down a series of numbers.

"Thank you, sir. Here's your computer."

Barry remained at the desk and opened the company laptop. He had a master password, that allowed him access to the system. He worked less than five minutes and then closed the laptop and stood up.

"I fixed your computer issue. There was a code error in the boot loader to the operational system."

"OK, thanks." Rory moved back to his desk, leaving his own laptop running on the conference table.

Barry scurried back to his small office. He had Rory's laptop's IP address and since he managed the company's Wi-Fi network, he could hack in. Whatever it was that he caught Rory looking at would soon be accessible to him. He was scrolling through the documents and pictures on Rory's personal computer in a couple of minutes, clicking through folders trying to find something interesting. Under the Pictures folder, a subfolder was labeled 'New Ideas.' It had two additional subfolders, named 'Online' and 'Private.' He had struck gold.

The online folder had dozens of Femdom pictures, which had been downloaded from different porn sites. Barry liked female domination, particularly giantess fantasies, and often masturbated to videos and pictures of men being subjugated by women. The personal folder blew him away. There were dozens of pictures of Rory and Ronnie, naked and sexually engaged. Ronnie playing the Femdom role, being serviced by Rory.

One near the beginning of the folder caught his eye. It was Rory with his legs spread wide. His asshole clearly visible as a dark, dusky pink knot surrounded by much paler pink butt cheeks. His hands were clasping his ankles, and his nuts were big low-riders. The cock was enormous and clearly dripping. In the foreground was Ronnie and an older woman posed with Rory's asshole between them. Barry got very hard, very quickly.

He jumped up and locked his door. Pulling his pants and underwear down around his ankles, he sat down and stroked his six-inch boner. He fantasized about being the asshole between the two women. He imagined what it would be like to be bear-hugged and carried like a baby by a giantess named Ronnie. In his imagination his face was buried between her huge tits, as she squeezed him tightly and lifted his feet off the ground. He had a quick orgasm, depositing the load on his stomach. He had tissues in a drawer to clean up with, since he masturbated almost every day at work.

Barry was still a virgin, and this situation gave him an idea how he might change his status. He thought about sending an email to blackmail Ronnie. 'That would be stupid because it leaves a trail,' he thought. 'I'll do it face to face with Rory. Then he'll deal with Ronnie.' He took several minutes to work out what he would say. He knew Ronnie would be back in the office Monday, so he needed to talk with Rory today. He would wait until almost 5:00pm, drop it on Rory, and then leave the building.

Later, he tapped on Rory's door and walked in.

"I need a quick word with you, before I leave."

"What? Oh, OK, go ahead, but make it quick. I've still got a lot of work to do before I can head for home."

"I have a proposition to outline. I don't need an answer today. We can talk Monday."

"Look, Barry, I don't mean to be rude, but I'm busy. I don't have time to listen to your proposition... whatever it is."

"OK, I'll get right to the point. I have accessed the personal pictures on your laptop. The ones of you and Ronnie naked are particularly good. There's also the one with Ronnie and another woman smiling with your asshole between them. They made a big deal at employee orientation about how important the company's reputation is. So, I want something in exchange for deleting the pictures."

"You little asshole! I'll have you fired for this."

"I don't think you'll do that. The damage I can do to your career... and Ronnie's isn't worth it. Besides, I am not asking for money."

"What do you want... you miserable little shit?"

"I want to be dominated by Ronnie. I want to be her slave for one evening. That's it. One night and I'll trash the pics."

Rory was enraged. He stood up.

"I'm leaving right now. Just talk to her about it. One night and no more pics."

As Rory began to step around his desk, Barry fled down the hall to the fire escape stairwell. He was gone.

"Oh, fuck me," Rory moaned.

...

"That little prick wants what?!"

Ronnie was livid. She had come straight home from the airport and was waiting when Rory finally got there at 7:00 pm. He quickly revealed the 'proposition' to her.

"I'm sorry, I shouldn't have been looking at them at work."

"It's not your fault. We were sharing personal photos on our personal electronic devices. Damn! I'd like to ring that little bastard's neck!"

"I probably would have, but he ran away."

"We should request a meeting with John, Jr. Explain we were having a private conversation on our own personal..."

"It's not John, Jr. that would be the problem. It's John, Sr. He's such a fuddy-duddy. It would freak him out. It could affect our partner track."

"God damn that little toad! I'm too angry to think about it now. Let's go out for dinner. We need to let it settle some... cool off. Then come up with a way to crush him like the cockroach he is."

They had a quiet Italian dinner at Mama Della's near their home. Between them they finished a bottle of Brunello di Montalcino. Ronnie was quiet on the way home. After they pulled in the garage she told Rory, 'I have a plan.'

"First, I want him to shave all hair below his neck. We tell him we will play with him until he has an orgasm..."

"He's maybe nineteen years old. He might want more than one," Rory suggested.

"OK, ... until he's had two orgasms. We promise not to injure him or draw blood, but he will be subject to discipline for failure to obey. He must do anything I ask him to if he's physically able. We give him a 'safe word,' but if he uses it the night ends."

"I like it." Rory nodded.

"I'll throw him around and find some excuse to blister his butt for disobedience. Would you be OK with me using you as my assistant. You can yell at him about his performance?"

"Yes, that's a great idea. I can see that your orders are carried out... still a sub to you, but a monitor on him... keeping him in the game. Forcing him to honor you... The Mistress."

"I will totally ignore him at work. He is 'beneath' my attention... an unseen minion."

I'll give him your reply first thing Monday morning.

"Excellent."

They didn't discuss it any further that weekend. Ronnie fucked him amazon style that night. On Saturday she sat on his face, and he gave her an amazing 'O.' Afterwards she had him suck himself, while she fingered his rose bud. Sunday, he gave her breakfast in bed. He slowly munched on her love box, while she ate. He kept a low buzz going, until she ordered him to finish. The 'O' was great, but she amazon fucked him again. They went to the nude beach near Kennedy Space Center that afternoon.

...

Monday morning Barry received a message from Rory as soon as he got to work. 'Need to see you immediately.'

Barry felt confident that his terms would be honored. He thought they had little choice but to comply with his wishes. He knocked on Rory's door.

"Come."

He opened the door and confidently walked up to Barry's desk.

"I want..."

"Do not speak, unless spoken to. My Mistress has deigned to accept your offer to serve her, however there are terms."

"Cool! I..."

"I have not asked you a question. Remain silent. Do you understand?"

"Yes, I do."

"These are her terms. First, you will shave all hair from your body, leaving only the hair on your head and eyebrows. Second, you will not speak to Mistress unless she asks you a question. Third, you will appear for service to her this Saturday at exactly 9:00 am. Fourth, you will do anything, and she means that literally, anything she asks. Fifth, you will be allowed two orgasms and then you will delete the pictures and leave her presence. Sixth, Mistress will allow you a 'safe word,' should you not wish to comply with her wishes. However, once used, the evening ends and you delete the pics. Finally, you will not be injured, nor caused to bleed. But outside that she will do anything she wishes. Do you accept these terms?"

He had many questions but realized he was only asked if he 'agreed' to the terms.

"Yes."

"Here is a written agreement between us. The first paragraph is a confession that you illegally used your position at the company to access my private laptop. This protects us from any future attempts at blackmail. Since you have verbally agreed, sign and date at the bottom."

Barry signed the document without reading it.

"Now get out of my office," Rory shouted.

Barry was excited. He believed he was going to see the Goddess Ronnie naked, and they would fuck. He was a bit disappointed that Ronnie and Rory had taken his ingenious way of arranging a three-way so badly. He shrugged off their failure to see his cleverness and mistakenly assumed that Ronnie would like the idea of two slaves once she saw his willingness to serve her.

...

Saturday arrived and Barry shaved his sparse pubic hair. He attempted to denude his balls but missed a half dozen hairs. Finally, he removed the small patch of body hair on his chest. He dressed in regular work clothes, but instead of his tidy whities he wore a pair of black briefs he bought at Walmart. He thought they were quite attractive and certain to win Ronnie's approval. He got hard looking at himself in the mirror, wearing only the briefs and imagining her looking at him lustfully.

He drove over to their house and parked down the street, as requested. He waited outside until 8:59 am, so he could ring the doorbell at exactly nine. No one answered the door. He didn't know whether to ring the bell again or wait. After a long minute, he tapped lightly on the door with one knuckle. He was getting frustrated by the time Rory opened the door. Rory was barefooted, wearing a sleeveless t-shirt and gym shorts. Barry stepped inside. Ronnie was nowhere to be seen.

"Are your ready to serve my Mistress?"

"Yes, I am," replied Barry.

"Strip off all your clothes and put them in this bag," Rory ordered and then walked away.

Barry stripped quickly and bagged his clothing. He was disappointed Ronnie wouldn't see his new briefs. Five minutes later Rory returned.

"Remove your watch and glasses as well."

He complied. Rory cuffed his hands in front and placed a collar around his neck. After attaching a leash to the collar, Rory put a blindfold mask over his eyes. Barry found all of this to be quite exciting and began getting an erection. Rory led him by the leash to a different part of the house.

In the new room, he could smell Ronnie. He had no idea if it was her shampoo or cologne or what. She didn't speak but he knew she was there. He became fully hard.

"Mistress will now inspect you to determine if you are properly shaved."

"Uh, OK. I shaved..."

Rory cut him off. "Shut up you cockroach. Only speak if asked a question. Do you understand?"

"Yep, um, yes Sir!"

Something hit Barry's cock... the palm of a hand? It hurt like hell whatever it was.

"Do not call me Sir."

"I'm sorry, I..."

His cock was swatted again and flew in the opposite direction.

"Shut up, idiot."

Barry remained quiet. He had expected to be under Ronnie's command. He thought Rory would be a slave also and they would be treated the same. He was uncomfortable with the direction this was going.

The scent of Ronnie became stronger. He couldn't see her and dared not reach out to touch her, but she was close. He felt a sharp, stinging pain over his left nipple. It took a moment, but he realized someone had pulled a missed hair out. A couple more were removed on his chest, but he managed not to cry out. Next, they found a few in his groin area. He had shaved carefully but obviously not thoroughly. The removals from his pubic area hurt more than the chest, but he continued to stoically resist verbally expressing his pain.

Someone was handling his balls. He thought, 'Oh shit!' Sure enough a moment later he experienced excruciating pain as a hair was slowly pulled out of his scrotum.

"You were instructed to shave all the hair from your neck down. You have disappointed your Mistress and will be punished." Rory said.

More than a dozen hairs were pulled slowly from various points around his nut sack. He had tears in his eyes from the pain but managed to avoid saying anything. He was groaning and sucking his breath in this agonizingly slow process. Despite the suffering he remained solidly erect.

"Bend over and spread your cheeks," Rory ordered.

'Fuck me,' Barry thought. He hadn't even tried to shave the inside of his ass cheeks. There were a dozen or so removals from this most intimate area, but surprisingly they didn't hurt as much as his nuts. Finally, the depilating was over. Multiple places on his body were still stinging. He thought the pain was over. His blindfold was removed. Ronnie was there! To his disappointment, she was dressed in workout clothing that she might wear to a public gym.

"Lay face down on the bench and hook your handcuffs over the end." Rory commanded.

Barry lay down and put his hands on either side of the end of the bench. Ronnie grabbed his legs and pulled him back, locking his hands under the bench. His nuts rolled up under him uncomfortably. He tried to lift and move forward, but Ronnie held him immobile. Rory walked around and took one of his feet, continuing the backward pull.

"Mistress will now punish you for failure to obey her order to shave yourself."

Ronnie pulled Barry's left leg back and to the left. Rory pulled the other back and to the right. This spread his ass open, but his nuts were still crammed under.

"Lift yourself at the waist," Rory ordered.

When he raised himself slightly, he felt his balls get brushed out by a stick or something. Ronnie dropped his leg and walked to the side. She showed him the crop and slapped it against his shoulder. It stung ferociously.

"Your safe word is 'thief,' as in what you are. A valueless creepy thief. Do you know what a safe word is?"

"Ye, uh, yes, Mistress"

"Do you understand that if you use the safe word, your pain will end immediately? You will delete the pictures and leave."

"Yes, Mistress."

"Excellent," she replied and struck his shoulder again in the same spot. It didn't hurt as much this time because it was still numb from the previous strike.

She moved back behind him and picked up his leg. He felt exposed and humiliated. His nuts and asshole were open to their view and even worse, to her whip thing. She rubbed it against his nuts, and he moaned with pleasure. That quickly turned to a grunt of pain as she slapped down on his jewels. He might have given up if she had struck him there again. Instead, she lashed out at his cheeks and thighs, repeatedly attacking his soft skin with the crop. Bright red whelps were appearing where the crop had been. When she finished, his ass and upper thighs were glowing a purplish red. It hurt like hell, but he was leaking precum.