It was obvious that Jim had money and lots of it, which he used prodigiously to mask his total inadequacy with the opposite sex. Jim's money had come through a vast inheritance and had nothing whatsoever to do with his job skills. In fact, his luck in the boardroom closely matched his fortunes in the bedroom.
So it was that initially, he showered Stephanie with gifts and expensive dinners in his bid to woo her in between the sheets. To his few friends, it appeared his strategy was working when one night, he managed to convince her to come home with him. She remained skeptical, and her suspicions were confirmed when she first caught sight of his pathetic, diminutive penis. To her dismay, she discovered that even with a raging erection, it was no more than three inches and was probably closer to two and a half.
Stephanie didn't know whether to laugh or be angry, given the amount of time she'd wasted so far in this relationship, and after he splashed his ineffectual load across her inner thighs prematurally, she responded by forcefully shoving his head down between her legs to make sure she got some satisfaction for an otherwise wasted night.
The following week, she didn't say a word to Jim, despite the many flowers and baskets he had had delivered to Stephanie's home. He knew he had blown it, and he was desperate to make amends. However, Stephanie was no fool. She finally returned his 20th call and told him they could only continue on as a couple if he agreed to abide by her rules. That meant doing as she said, no matter what and no matter where. She informed him that traditional sex was out of the question but that if he agreed to her terms, she would grant him some occasional sexual privilages.
Stephanie made it clear that she intended to see other men--real men--and that Jim would have to accept his position as her servant. The alternative was for him to stay out of her life forever and never see her again. Crushed by that prospect and ever desperate to get on her good side, Jim quickly agreed to her demeaning terms and he moved into her place later that week.
However, Jim's new life hardly went as he had planned. He soon came to discover that his new life living under Stephanie's thumb would be filled with non-stop humiliation. She started dressing him as a little girl and cut him off from sex completely. And when he asked to be able to kiss her, she responded by telling him he was only allowed to worship her ass.
Jim found his privilages slipping away as he became Stephanie's live-in maid. But living in such close proximity to a beautiful and sexy woman, Jim was constantly horny and whenever he was alone, he'd masturbate furiously while gazing at Stephanie's glossy photo layouts. It was when she came back from work prematurely that she caught him finishing up his assigned chores with goo stains in his panties. Without hesitation, Stephanie yanked him over her lap, flipped up his dress and proceeded to paddle his pantied bottom until Jim was a blubbering mess.
"Since you insist on acting like a baby--I'm just going to have to treat you like one," she informed him sternly.
Over the next week, she converted his room to a baby's nursery and started forcing him to wear diapers and plastic panties under his dresses. Jim wasn't happy about the arrangements but because of his weak-willed nature, he just couldn't stand up to her.
Stephanie kept herself busy seeing other men but she also kept close tabs on Jim, aware that sissies need the strong hand of discipline. After finding more stains in the baby diapers she made him wear, she realized stronger measures would be necessary to prevent him from masturbating. She put in an overnight order for a PICO Birdlocked chastity device and Jim found himself wearing it at his very next diaper change.
Due to it's devilish design, the Birdlocked prevented any kind of erection and with it's silicone spikes discouraging any kind of arousal, the PICO device ensured that Jim would no longer be able to masturbate while wearing his bunny soft, cuddly diapers, no matter how much time he had alone. Much to Jim's dismay, Stephanie kept it locked in place, 24 hours a day.
Now that Jim was fully controlled, Stephanie concluded it was important to take the next step in his humiliation. When she invited her male friends over, Stephanie forced him to serve them drinks while wearing his sissy little girl outfits. The men loved to slap his fat diapered bottom as he went by and they often made lewd comments about his smooth, shaved legs.
And of course, from time to time, they required other services of him and Jim was forced to comply, even when he found it degrading and distasteful.
Occasionally, Jim found it quite a challenge to swallow the huge loads of creamy semen being pumped into his mouth but he also knew the consequences for failing to live up to Stephanie's standards. Stephanie never hesirated to pull him over her lap for a spanking or even let her boyfriends do it if he displeased them.
He became quite adept at cocksucking, although despite his constant pleading, he was still getting zero sexual gratification from Stephanie as she was adamant about keeping his neglected little penis locked up. However, for the sake of his general health, it was decided that he should be milked from time to time. While she insisted he keep his chastity device on, she provided enough anal stimulation with her strap-on to release the built up cum that had accumulated in his purple, swollen balls. Jim couldn't get the pleasurable, explosive release of an orgasm, but at least he felt some measure of relief afterwards.
And just for her amusement, Stephanie would sometimes allow one of her male friends to provide the stimulation.
Jim thought for sure he'd be split in two by some of her hunky boyfriends but he did his best to take it because Stephanie assured him it was for his own good.
Jim's life certainly didn't turn out as he expected. But sometimes, that's the price one pays for being a weak-willed sissy.