Brandon's Initiation to M.A.M.A.

Heather leashed Brandon's balls and they began walking down the hallway. They passed through a set of double doors with a sign that said, "Punishment Wing". Each door in this wing was labeled "Punishment Room" followed by a number. As the continued down the hall Brandon could hear muffled noises coming from one of the rooms. The sounds of other males being punished.

"Here we are," said Jillian as she opened the door to Punishment Room 13.

Brandon crawled inside and looked around. The room was pretty large. He had seen rooms like this on internet porn sites. It had all the BDSM equipment you could think of. He looked up at the two beautiful women who were going to punish him. A small part him was aroused by the thought of being punished by them. But not knowing what they plan to do and how harsh they would be made him nervous.

"On your feet Brandon," Jillian commanded

Brandon sprung to his feet. And erection started growing as he checked out Heather's tits.

Heather removed the leash and guided him towards some kind of pillory device. He knelt on a padded bench about two feet off the floor. She attached his ankles to shackles on each side so his feet couldn't move. Then she locked his penis and balls into some sort of stock at waist height to hold him in place. And his wrists were attached to shackles on either side of the stock that locked his junk. His erection was pretty noticeable at this point.

There Brandon was in a kneeling position with his cock and balls trapped, his back side fully exposed, and his feet hung off the edge of the padded bench toes facing the floor.

"He's ready Mistress Jillian," spoke Heather.

Jillian reached into a drawer and pulled out a riding crop and handed it to Heather.

"Ok Brandon. I'm going to list your misbehavior today," said Jillian. "One... You addressed a mistress by her first name only.... Two... You were caught on camera touching your penis twice... And three... You didn't pee with on leg up when using the toilet in your room."

Brandon was a little surprised when he heard the list.

"Do you have anything to say before we begin?" Jillian asked.

Choosing his words carefully Brandon responded. "I didn't mean to touch my penis Mistress. It's just a habit. Please forgive me," he said pausing to think for a second and continued. "Also, I thought I was allowed to sit when using the toilet in my room. Isn't that what you told me?"

"You sit only to do number two," she responded. "That should have been pretty clear."

"Forgive me Mistress. I misunderstood. It won't happen again," he said.

Brandon figured being apologetic was his best bet for some mercy, not knowing what his punishments would be.

"But I don't recall calling any mistress by their first name," he said. "Not since you told me it was against the rules."

"You called me Heather the moment we met remember?" Heather chimed in to say. "Then you corrected yourself."

Brandon recollected that moment and said "I'm sorry for that Mistress Heather. Please punish me."

Brandon found submitting to Heather very arousing. He couldn't believe that a part of him was enjoying this. He was willing to let Heather do anything she wants to him. She was the most beautiful woman he had ever seen.

"Our punishments at M.A.M.A. are standard for each type of offense, but they get harsher when the same offense is committed multiple times," she said. "Heather if you would please read him his sentence."

Heather began to recite Brandon's punishments, "For touching your penis, you will receive 5 hard crop slaps to the head of your penis for each offense...so 10 in total... For sitting on the toilet to pee you will receive 50 hard lashes by a paddle to your ass... And for your disrespect to me, I get to choose any punishment I deem fit."

Brandon's eyes widened as Heather spoke. Not having every experienced any of these things, he wasn't sure exactly how bad it would be. Then suddenly Jillian shoved a ball gag in his mouth and strapped it around his head.

"Ok let's start with his penis" Jillian said. "Heather if you would do the honors."

Heather looked at Brandon's erect cock and gave it a good hard smack with the crop. WHACK

"Mmmph," Brandon yelped into his gag and pulled on his restraints.

WHACK, "Two..." WHACK, "Three...", Heather continued.

Jillian just stood back and watched with a smile on her face, "I hope you're learning your lesson... Do NOT ever touch your penis while here," she said. "Not even if it itches."

WHACK, "Nine..." WHACK, "Ten..." Jillian was finished spanking his dick head.

Brandon's penis head was stinging. His hands and feet shook to the pain. He looked at Heathers pretty face. He somehow found it pleasurable coming from her.

"Ok, now his ass," Jillian said handing Heather a long leather paddle.

Heather walked behind Brandon and started swinging the paddle at his vulnerable ass.

WHACK, "One..." WHACK, "Two..."

Brandon continued to scream into his gag. He tried to shift his ass around to avoid the strikes, but his movement was very limited because his cock and balls were in the pillory.

While Heather was hacking away at Brandon's ass, Jillian walked up in front of him and rubbing his sensitive penis head. "You should be thankful to your parents for having you circumcised," she said.

Brandon continued to yelp with each one of Heathers strikes.

"Dickhead spanking is especially brutal to the uncut males," she continued. "We peel back the foreskin for the punishment. Their heads are much more sensitive. They all end up crying."

A few minutes past. WHACK, "Forty-nine..." WHACK, "Fifty." Heather was finished spanking his ass.

Brandon's ass was beat red, and cock still rock hard.

Jillian turned towards Brandon. "Look at that boner," she said. "Any longer and he would have erupted."

Heather walked in front to see it also.

"You actually enjoyed being punished Brandon," said Jillian grinning. "You can't hide it with a boner like that."

Although the punishments were difficult to bear, Brandon did get a feeling of arousal being helpless with two beautiful women tormenting him. "Am I actually a masochist?" he thought to himself.

"Ok babe," Jillian said speaking to Heather. "What's your punishment going to be?"

Heather really wasn't offended by Brandon accidentally calling her by her name. Afterall he immediately corrected himself and apologized. But she was a sous-mistress in training so she had to do something that would impress her mentor.

She thought for a few seconds looking at Brandon. "I want to squeeze his balls," she said turning towards Jillian.

Brandon's eyes widened in fear as he mumbled into his gag. "No please... Not my balls..."

"Now you're talking," replied Jillian. "For how long?"

Heather thought for a second and started counting with her fingers. "Fifteen seconds nonstop," she said.

"Why only fifteen seconds?" asked Jillian.

"Because that's how many letters are in the name "Mistress Heather"," she explained. "I figured that would be appropriate. Making the punishment fit the crime," she said giggling.

Jillian nodded almost impressed. "Ok, have at it," she said.

Heather walked up to Brandon with his package still trapped in the pillory completely vulnerable and at her mercy. His balls were pushed up to either side of his penis.

Brandon tried pulling at his restraints, but it was useless. He began to breath faster as he braced himself for what was about to happen.

Heather looked into Brandon's pleading eyes and grabbed his testicles with both hands. She felt bad about what she was about to do. M.A.M.A had put her through some femdom basic training when she first started. One of the lessons she was taught how to squeeze a man's balls to inflict the maximum amount of pain without doing any damage or rendering them unconscious.

"Timer is set Heather," said Jillian. "Ready when you are."

Heather nodded and leaned closer to Brandon. She came face to face with him and began squeezing Brandon's balls hard.

"mmmmmppphhh...MMMMMMMPPPPPHHHHHHH," he screamed louder and louder into his gag while pulling on his restraints.

The timer counted the seconds as Heather applied constant pressure without letting up. About ten seconds into the squeeze Brandon's cock erupted, shooting his cum all over Heather's abdomen and thighs. Then the timer beeped. Fifteen seconds had passed, and she immediately released Brandon's balls.

Brandon continued to moan loudly, both from his orgasm and his sore balls.

"Well done," said Jillian grinning at Brandon. "You made him cum during a ball squeeze. And I think that was his fifth time today"

The women quickly unstrapped him, and Brandon immediately fell to the floor grasping his swollen balls. He was looking up at Heather. Even though she caused him extreme pain he still wanted to admire her beauty from the floor.

"I'm sorry mistress," he said apologizing for cumming. "I couldn't control it. Please forgive me."

"Aren't you cute apologizing right away," said Jillian. "Cumming during a prolonged ball squeeze is a common occurrence. We do it all the time for fun. It's amusing for us, not so amusing to you of course. But you won't be punished for it."

Brandon was relieved to hear it.

"Ok but now you have to lick it up," Jillian said looking at Brandon.

Brandon looked at the mess he made all over Heather's beautiful body. He was in no mood to lick up his own cum, but licking Heather was not something he was willing to pass up. He crawled over to her and began lapping up any droplet stuck to her spandex. Some even ran down to her crotch. After it was all cleaned up, he knelt before her.

"There's some on the floor too," said Jillian pointing.

Brandon hesitated a little but licked that up too. He didn't feel like getting zapped. His balls were already hurting enough.

"Ok, it's almost time for dinner. Before we head over do you need a bathroom break Brandon?" asked Jillian.

"Yes mistress," he muttered while slowly lifting himself off the floor onto all fours.

"Heather, you take him" she said. "Remember no sliding on the rules in there. I'll meet you in the cafeteria."

Heather leashed Brandon's aching balls and he slowly crawled out softly groaning with each movement. She guided him to the "doggy" bathroom where he was again successful in not spilling anything. They then continued down to the cafeteria to eat their dinners. Again, on the floor like before.

The time was about 9pm, and Jillian walked Brandon back to his sleeping quarters and unleashed him.

"Be sure to get a goodnight sleep" she said. "Tomorrow will be very eventful for you...he he he! And remember Brandon.... You deserve this right?"

"Yes, Mistress Jillian, I deserve this", he repeated.

Jillian walked out of the room and shut the door. Brandon was all alone. He climbed into the bed and began to reminisce everything he went through today. His balls ached, and his ass and dick were still stinging. It was somewhat brutal but yet he was extremely aroused by all of it. His dick began to get erect as he lay in bed. All he could think about is how great it would be to masturbate to Heather, but he managed to control himself. He couldn't imagine what the punishment for that would be. Instead, he just closed his eyes and went to sleep. This was just the first day!!

TO BE CONTINUED.....