Leashed man held by a woman in lingerie - Picture from Depositphotos.com
Picture from Depositphotos.com

First steps into the sexy world online – what will he encounter?

Content warning: The following fictional story contains themes of religion. All characters are of legal age and have participated willingly.

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 has 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 things can’t last forever.


“Zacharias, boy, maybe I have been too harsh on you. Why don’t you come back home?” Zacharias’s mother his mother was using her sweetest voice.

Zacharias swallowed, his hands holding the phone were suddenly trembling.

“Oh, mother, I don’t know. I, well…”

“You can come back, dear boy. I’ll make you potato gratin with the grilled chicken you adore. And you can make a pudding for dessert?”

“Mother, I don’t think that…” His voice was slightly louder this time.

“Don’t be foolish. You can’t sleep on the streets for another night. I’m offering you a roof over your head, and I need you to make
breakfast for me.”

“Mother! I haven’t slept on the streets. If that’s what you thought, why call me after a week? I’m staying over at a friend’s, and I’m perfectly happy here.”

Sheryl walked on up to him and kissed him on the cheek. “Do you need help?” she asked.

“Who is that? What harlot are you staying with? I demand you come home right now.”

“That’s my friend Sheryl. I’m staying at her and Peggy’s place, and I feel excellent here. You make your own breakfast. Goodbye, mother.” He disconnected the call.

He giggled nervously as Sheryl pulled him into an embrace.

“Well done, Zach. Glad to see you’ve found your balls.”

“Mama is going to be so mad at me.” His hunched shoulders contradicted his earlier firm words.

“Keeping you all to herself wasn’t fair of her. It’s good you chose for yourself this time.”

“I know, but it’s freaking scary.”

“Welcome to adulthood.”

Zacharias exhaled and returned to the bathroom he had been cleaning. He had never been this insolent to his mother. He thought, guessed, he was doing the right thing, but he was scared to death. An alarm sounded from his phone. He quickly turned it off. It was 12:55, nearly time for his appointment with Lady Isabel, yes, another woman in his life.

After Peggy’s instruction to go online and investigate what he really wanted to do in life, he discovered there were many sex things on the computer. He enjoyed how it made him feel, looking at the pictures of all the pretty ladies and even some videos. The church had always warned him about the devil’s work which was evident on these pages. But the same church had kept real sex things from him too, and he now knew what pleasure they brought. Sinful pleasure, yes, but too delicious to ignore.

Luckily he had found Lady Isabel, who was more than willing to help him find his way. There were so many friendly people in the world. All you had to do was be kind to them, and they would return the favour. Zacharias emptied the bucket and put away the cleaning cloth.
He opened Peggy’s laptop and logged into his account. She had made one for him so he could browse the internet freely. He turned on his webcam. His heart jumped when he saw his online lover.

“You’re late, you worm,” she hissed at him from the screen.

Zacharias lowered his head. “I’m sorry, Lady Isabel.”

“It will cost you. Transfer 150 Dollars to me now, fifty more as punishment for being late.”

“Of course, Lady Isabel.”

Zacharias clicked the link from Lady Isabel’s profile and transferred the requested 150 Dollars. He had saved Peggy’s credit card information and used it to help his online friend. Surely Peggy wouldn’t mind.

He returned to the screen which showed his friend. He copied the transaction receipt in the chat.

A smile formed around the woman’s lips. “I guess there is still some use for you. Show me that puny dick of yours.”

Zacharias lowered his pants and sat back so that his penis was visible on the cam. It was hard as rock already.

“Looks pretty useless to me. Stroke it.”

Zacharias didn’t understand why the woman’s words turned him on so much, but they did. He stroked his sensitive member at her command.

“Could I see yours?” he whispered.

“What was that? You think you’re worthy enough to see me naked? Are you mad or something? I showed you my boobs last time; that was way more than you deserved. Live on that memory, boy; that’s all you’re gonna get.” She chuckled at the impact of her words. “You’re close to cumming, aren’t you?”

Wildly breathing through his mouth, he nodded.

“Stop touching yourself. Right now.”

He dropped his arms to his sides, his dick still pulsing from excitement.

“Don’t you dare orgasm. You haven’t deserved it.”

“Yes, Lady Isabel,” he whispered, trying to deal with the emotions whirling through his body.

“I’ll see you again tomorrow, same time. Don’t touch yourself.”

“Of course, Lady Isabel.”

Her screen went black. Zacharias closed his eyes and tried to steady his breathing. He wanted to continue masturbating and cum so bad, but her intense eyes haunted him even when she wasn’t online. He shouldn’t.

The door burst open, and Sheryl entered the room. “Zacharias, do you know where…oh my” She smiled at the sight of the half-naked man.
Zacharias covered his penis with his hands. “I’m sorry, I didn’t know you would…” he quickly apologized.

“That’s no problem, no problem at all. I should have knocked. I understand a virile man like yourself would want to pleasure himself now and then while looking at…” She looked at the screen. “Lady Isabel? What’s this?”

“Nothing, nothing, she’s just a friend.”

Sheryl looked sceptical. “A friend? With a Venmo? You haven’t sent her any money, have you?”

Even though Zacharias was already red from the earlier online chat, his blush now deepened.

“Oh, Zacharias, how could you? And literally, how could you? I thought you didn’t have a credit card? You didn’t use mine?”

Zacharias shook his head.

“Oh my God, you used Peggy’s? You moron. She’s hard at work, and you squander her money on an online fraud?”

“She’s not a fraud. She’s my mistress!” he exclaimed.

“Oh, you’re looking for a mistress? I didn’t want the hassle in my current state, but I think I’ll need to teach you a lesson. Let’s get you in position before Peggy returns. I’m sure she’ll have some plans for you too when she hears this story.”

Zacharias didn’t know what to say or how to respond. Deep down, he knew using Peggy’s credit card had been wrong. And even deeper down, he was thrilled that Sheryl had discovered and was going to punish him. He didn’t understand why, but the thought alone turned him on immensely.

Fifteen minutes later, he was tied down on the couch, gagged with a scarf, a string restricting his balls and penis while Sheryl lubricated his ass. He mewled as she filled his ass with a medium-sized buttplug. Never before had he felt anything like this. He had always thought only the most debased people would stoop this low, but now it was him. And while he hated it, he secretly loved every minute of it.

With a push and a stretch the buttplug sank in. Zacharias groaned at the intrusion. Sheryl slapped his ass. “This is a good start. Hold on tight until Peggy comes home.”

Zacharias closed his eyes. This was not how he had planned his day. He prayed to God, begging for forgiveness. He knew he had strayed from the path. He understood his current condition was a way of correcting his mistake. But how sinful was it that he remained in a state of arousal?


Wicked Wednesday

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