Chapter 24

Jim woke up to a gentle shake, his eyes fluttering open to the bright sunlight streaming into the room. He blinked a few times, adjusting to the light, and noticed two young women standing by his bedside. One was Dawn, the other had soft, wavy brown hair and a gentle, reassuring demeanor, her name was Mercedes.

“Good morning, sleepyhead,” Dawn, chirped. “It’s graduation day!”

Jim rubbed his eyes and sat up, a sense of excitement mixed with nervousness coursing through him. Graduation day. Mercedes handed him a fresh set of clothes and told him to get dressed.

As Jim dressed, Dawn and Mercedes teased him mercilessly, their eyes twinkling with mischief. They commented on his physique, a product of months of dedication and hard work, and touched him lightly, sending shivers of anticipation down his spine.

Once Jim was dressed and ready, Dawn handed him a shake. “Drink up, big boy,” she said with a wink. “You’re going to need your energy today.”

Jim took the shake and drank it down, feeling a sudden wave of sleepiness wash over him. He looked at Dawn, confused, and she laughed. “Oh, it’s just a little sleeping pill. We have a surprise for you when you wake up.”

Jim’s eyes closed, and he drifted off into a deep sleep.

When Jim woke up again, he found himself restrained on a table, a strange sensation at the base of his erection. He looked down and saw that his erection was larger than ever, bound by a tight band. Dawn and Sam were standing beside him, a mischievous glint in their eyes.

“What’s going on?” Jim asked, his voice tinged with both excitement and apprehension.

Mercedes climbed onto the table, straddling him, and Jim’s heart leaped into his chest. He was about to experience penetration for the first time in almost four months. He watched as she slid down, taking him in completely, but to his dismay, he couldn’t feel her.

Dawn leaned over, her smile never fading. “We administered a local anesthetic while you were asleep. Couldn’t have you enjoying yourself too much, could we?” she said, her voice light and teasing. “We had to give you your diploma, after all.”

Jim watched as Mercedes ground on top of him, unable to feel the pleasure he so desperately craved. Dawn informed him that the anesthetic would wear off soon, and he hoped with all his heart that it would be before the girls finished up.

As Dawn finished with her turn, Jim started to regain sensation. He moaned in frustration, knowing that he would likely be denied the release he so desperately sought. Dawn leaned down and whispered in his ear, “You remember Doug’s rules, right? Sex with two women means two more months of chastity.”

Dawn laughed as Jim let out a frustrated groan, but she wasn’t done with him yet. Sam stepped up between Jim’s legs, and he quickly wished for the numbness to return. Sam was bigger around than Doug, and Jim knew this would be a challenge he had not anticipated.

As Sam began to move, Jim felt an additional pain on his ass cheeks, a sensation he had never experienced before. Dawn explained, showing him a picture. “It’s your diploma,” she said proudly, showing him a tattoo across his cheeks that read “Certified Painslut.”

Jim grimaced, a mix of pride and pain coursing through him. Dawn informed him that the last step was to accept her essence. Jim opened his mouth, and Dawn started to piss, a warm stream entering his mouth. He greedily swallowed, showing his appreciation for her hard work.

Throughout the ordeal, Jim’s mind raced, a flurry of emotions flooding his system. Despite the discomfort and the humiliation, he felt a sense of accomplishment and acceptance. The pain and the restrictions only fueled his desire, pushing his boundaries further than he had ever imagined.

As Dawn finished, she wiped his mouth with a gentle touch before helping him up. “You did well, Jim,” she said softly. “You’re officially graduated. Now let’s get you cleaned up and ready for what’s next.”

Jim nodded, a mix of fatigue and exhilaration settling over him. He knew that his journey was far from over, but the path ahead was filled with new challenges and opportunities for growth. He looked forward to reuniting with Doug and Kris and to the extraordinary moments that lay ahead.