Picture from Depositphotos.com
Picture from Depositphotos.com

Playing online was fun, but now the real world consequences are catching up…

Every week, home-schooled Zacharias receives a massage from his massage therapist. She has been teaching him the more carnal sides to life, like receiving oral pleasure and how to please a woman with a toy. For his twenty-second birthday, she had a special treat planned for him. After this surprise, Zacharias’ mother barged in and kicked him out. Peggy invited him to her place. Peggy and her pregnant friend Sheryl enjoyed their time together with the new housemate, but the arrangement couldn’t last forever. He discovered an online Mistress, but he used his housemate’s creditcard to pay for her services. And then the housemate found out…


Another fifteen minutes later, Peggy entered the living room. She halted when she saw Zacharias in his precarious situation.
“What’s going on here? I thought you didn’t want to play while you were pregnant?” she asked her friend Sheryl.

Sheryl stroked her rounded belly. “I didn’t, but your little housemate here forced me. I had no choice.”

Peggy looked from Sheryl to Zacharias and back. “Him? What did he do?”

Peggy had known him for several months now and couldn’t see what he could have done to her female lover.
“Did he hurt you?”

Sheryl shook her head. “No, nothing physical at least. I suggest you ungag him and let him confess while kneeling.”

“All right.” Peggy frowned as she untied the scarf and helped Zacharias climb off the couch. She raised her eyebrows when she discovered his buttplug and the bondage around his sack.

“Time to confess your sins.”

Zacharias shivered at the words. “I…I only did what you asked me to, Miss Peggy. I went online, and I searched for opportunities.” He studied his trembling hands. “Lady Isabel promised she would help me.”

“Be honest, Zacharias, tell her everything,” Sheryl intervened.

Zacharias was now near to tears. “Lady Isabel, my Mistress, asked for a small compensation, so I gave her some money. But since I don’t have a credit card.” He studied the floor, unwilling to look at Peggy.

“You used mine. Is that what you’re trying to say?”

Tears began to roll down Zacharias’s cheeks. He had never meant to upset Miss Peggy. He just couldn’t find any other way to please his Mistress.

Sheryl nodded. “That’s why I put him in this position.”

“How much, Zacharias?”

“Two fifty.”

“Two Dollar fifty? Oh my God, you don’t mean two hundred fifty? Zach, that’s what I make in a week. How could you be so stupid?”

“I’m sorry, Miss Peggy. I’m so sorry.”

“You’re gonna pay for this, Zach, and you’re gonna pay me back.”
She turned and left the room to return shortly after holding a cane.

“How long has he been in this bondage?” Peggy asked Sheryl.

“Thirty, forty minutes or so.”

“Then he can last a little longer. Get up. Place your hands against the wall.”

He followed her command but winced at the feeling of his restrained cock and ass.

“Those’ll be the least of your problems now, boy.”

“He’s wearing a big plug, Peg,” Sheryl informed her friend with an evil grin.

“That’s good. I was hoping to begin training him so he could receive my strap-on. What better day to start than now? I said, hands against the wall. Spread your legs.”

Zacharias assumed the position. He didn’t wince as the first stroke hit him.

“Didn’t you feel that? I didn’t think I was being kind,” Peggy inquired.

“Momma said I shouldn’t make a sound.”

“Oh, so you’ve been a bad boy before? Guess that means I should try harder to get my point across. Don’t - steal - my - credit-card.” She emphasized each phrase with a hit from the cane.

“No, Miss Peggy, I’m so sorry,” he whimpered while his belly hit the wall from the impact.

Soon his back and ass were decorated with red stripes.

“Three more, Zacharias, intense ones. My arm is getting tired.” Peggy delivered the hits as she had foretold.

At the last one, he did let out a cry of pain.

She roughly turned him around and removed the string that held his penis and balls together. He gasped at the relief.

“Stand in the corner, hands behind your back, and think about what you have done. Also, think about how you are going to repay me.”

“Yes, Miss Peggy,” he replied meekly and did as he was told.

Peggy went over to Sheryl. “Do you want a drink?”

“Yes, some tea would be great.”

“I should have asked him to make it for us, but I guess it’ll have to be me.” Peggy chuckled and went to the kitchen to make the tea.
When she returned to the living room, she found Sheryl next to Zacharias, fondling his striped ass and playing with the butt plug.

“I wish I had been the one to spank him,” she remarked.

“You can do round two tomorrow. I doubt one lesson will be enough to drive this in.”

“Perfect.” Sheryl gave him a sound slap on his ass and joined Peggy.

“What do you think his punishment will be? Buttplug training day and night? Will you fuck him tomorrow wearing your XXL strap on?” She winked to Peggy, making clear this was only to antagonize their subject.

Peggy wiggled her eyebrows. “Hmm, I don’t know. That sounds like a great plan, actually. Maybe he should be naked all day, so you can do that bondage thing around his dick again. Ooh, I know something! We should get some ginger tomorrow and hot sauce and rub that at his most intimate spaces. I bet that’s something his momma never did to him.”

“I’ll get a spatula and whip his dick with it,” Sheryl added happily.

Zacharias whimpered. He couldn’t take it anymore. He ran towards the two women and fell to his knees. “No, please don’t do that. I beg you. I’ll do anything to make it right. I’m so sorry.” Tears were streaming down his face.

“Really, Zacharias?” Peggy took hold of his chin and held up his face. “Because you’ve been a very bad boy.”

“Yes, yes, I promise. Please.”

“How are you going to pay me back for what you stole?”

She knew he had been too focused on their conversation that he hadn’t had time to devise any plans.

“I don’t know, but I’ll come up with something.” He quickly wiped the tears from his eyes.

“How about you go door to door and ask the neighbours if you can wash their cars? Even if only for five dollars, how does that sound?” Peggy suggested.

“Yes, yes, I will! Want me to go now?”

Peggy looked him up and down. “You’d be in a whole lot more trouble if you went out like this. Tomorrow is fine. Now return to your corner. Your penance isn’t over yet.”

“Yes, Miss Peggy, Miss Sheryl.”

He resumed his place in the corner, very much relieved he had prevented those cruel punishments from happening. 

He knew it had been wrong what he had done. Washing the cars of the people in the street and the other roads nearby sounded like a perfect plan. He was good at cleaning, so he knew he was gonna do great. He only had to slip a message to Lady Isabel soon. And that buttplug things inside of him was weird too. He knew it was wrong and should be expelled, but somehow it felt pleasant too? 
He began to see he had indeed been raised in a sheltered lifestyle, but the real world was very confusing so far. Mysterious and intriguing, but by the way his butt felt, pretty painful too. One day he would understand it. And now he would pay Miss Peggy back and please both Miss Peggy and Miss Sheryl in any way they wanted. And Lady Isabel too.


Wicked Wednesday

mmmMondays

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