Chapter 26

As January gave way to February, Jim marked the days on his calendar with a mixture of anticipation and frustration. The concept of “international chastity month” wasn’t something he had ever heard of, but Kris had presented it with such conviction that he couldn’t help but comply. The wait was agonizing, but he found solace in the transformations happening to his body. Each day, he stood in front of the mirror, noting the changes—the weight that had once clung to his midsection now redistributed in unexpected ways. His chest was fuller, and his buttocks were surprisingly firm. His nipples, though, were the most striking change; they appeared perpetually swollen and sensitive, a result of Kris’s newfound fascination with her silver bells.

Jim sighed as he examined himself, memories of the Christmas celebration still fresh in his mind. Kris had decorated his nipple rings with heavy silver bells that jingled each time he moved. She then had him crawl to her, enjoying the tinkling of sound that came with each movement. When he got to her she had him stay on all fours so the bells hung from his chest without touching the floor. They were heavy enough to stretch and pull his nipples but were not extremely painful. Kris had then moved behind him and removed the large plug. She had made him keep up the stretching exercises that Dawn had implemented at Thanksgiving and his flexibility had increased tremendously. He was now able to stand flat footed and bend over and place the palm of his hands flat on the floor. The extreme weight loss helped but the daily stretching routine had created flexibility that exceeded what he had had as a child.

Of course Kris had also made him keep up with the anal stretching also. He was now wearing a 6 cm diameter plug full time and his max capacity was up to almost 10 cm. Jim had questioned the need for continued stretching since he was already able to handle Doug easily and had never met anyone larger. Kris had joked that it was not about need, just want, and she wanted to see what he truly could handle. She pointed out that baby’s heads were sometimes as large as 12 cm in diameter so that was her ultimate goal. She also threw in a smartass remark about starting a horse training business and using him as a teasing mare! At least he hoped she was teasing. With his plug removed Kris started toying with his ass using three fingers and quickly switched to four. Jim had handled this so Kris decided to up the ante. She folded her thumb against her palm and pushed in, with a bit of resistance her hand popped inside. She now had her hand completely inside of Jim to her wrist. Kris was a tall woman but not very large boned so Jim was relatively comfortable even with her entire hand in his ass. Kris then started experimenting with how deep she could go. Dawn had reported that he was able to handle 35 cm and after a lot of bell ringing and pushing, she was able to get her arm almost to her elbow. The combination of the sights and sounds caused Kris’ pussy to throb with each ringing of the bell. Jim and Kris had both become Pavlov’s dog, the sound of his bells ringing had become a common occurrence since, each time driving him to the brink with pleasure and pain. He didn’t understand why his body reacted so strongly, but he couldn’t deny the exhilaration it brought.

Meanwhile, Doug watched Jim’s transformation with a mix of admiration and growing desire. As a dominant, he appreciated the subtle changes in Jim’s physique and the increasing surrender in his demeanor. Doug had seen Jim evolve from a timid, overweight man to someone steadily gaining confidence in his own skin. The dynamic between Jim, Kris, and Doug was shifting, becoming more fluid and intertwined. Doug found himself drawn to Jim’s vulnerability and Kris’s emerging dominance, each filling a need he hadn’t known he had.

One afternoon, while Jim was at work, Kris invited Doug over for coffee. They sat in the cozy living room, the winter sun filtering through the curtains, casting a warm glow over everything. Kris poured the coffee and handed a cup to Doug, her eyes meeting his with a playful spark.

“You know, Doug,” she began, “I’ve been thinking about our dynamic, about what we all need and want.”

Doug raised an eyebrow, intrigued. “And what have you been thinking?”

Kris leaned back, a smirk playing on her lips. “I think Jim needs more than just the physical changes. He needs mental stimulation, something that rewards him.”

Doug nodded, sipping his coffee. “I agree. He’s making remarkable progress.”

Kris leaned forward, her voice dropping to a conspiratorial whisper. “I have a plan. Valentine’s Day is coming up, and I want to make it something he’ll never forget.”

Doug felt a thrill run through him. “Tell me more.”

Kris explained her idea, her eyes gleaming with a mix of mischief and desire.

“But,” she added, her voice serious, “it’s crucial that we both are there to be with him.”

Doug nodded, understanding the importance of family. “Of course. Let’s make this something that will strengthen us all.”

As the days ticked closer to Valentine’s Day, Jim found his anticipation growing. He knew Kris and Doug were planning something special, and the uncertainty both excited and terrified him. He trusted them implicitly, but the unknown always held a certain thrill.

On the morning of February 14th, Jim woke up to find a note on his pillow. It was written in Kris’s flowing handwriting, and it simply said, “Be ready by 7 PM. Wear something comfortable.”

Jim spent the day in a state of nervous excitement, his mind racing with possibilities. He prepared as instructed, donning a simple pair of jeans and a comfortable sweater. By 7 PM, he was pacing the living room, his heart pounding in his chest.

Jim paused in front of the full-length mirror, admiring his transformation. The thong and camisole felt surprisingly comfortable, and the skinny jeans and sweater combo gave him a sleek, modern look. Jim could not believe that his normal underclothes were considered women’s lingerie, but they worked. He had switched to thongs after Thanksgiving to reduce irritation on his new tattoo. He also found that they helped keep pressure on his plug which had become a nearly permanent addition to his wardrobe. The camisole was added in the last month. Ever since his nipples began to swell and grow from Kris’s games he had found most shirts were to rough. The silk of the camisole was much more soothing. He adjusted his ankle boots and ran a comb through his neatly trimmed beard. His beard was still full and white, even though most of his hair had fallen out due to the extreme diet. The changes in his appearance over the past few months were monumental, and he could see a newfound confidence sparkling in his eyes.