PART 10
Gwendolyn interrupted her confused son’s thoughts. With a start, Josh realized his mother had drawn close to his side. Lost in his own head, he hadn’t seen her move. Yet she now held a puffy pink clothes hanger. Of course the hanger itself wasn’t the problem… rather it was what the hanger itself held. Josh stared with dismay at the pink and white item he had especially tried to avoid thinking about. The sinking feeling in his tummy told him that the moment he had dreaded most was now at hand.
Inside the world of his mind, putting on this particular garment would effectively shred what little remained of his “bad boy” act. Somewhat irrationally since he was already wearing panties, the flustered teen felt he was standing on a threshold. Until that moment, he somehow thought his normal life could be clawed back. His eyes darted feverishly around the girlish room, but he saw no escape. Worst of all, he had willingly agreed to this. But maybe there was still a way out…
Sensing a rise in his agitation and perhaps a last shadow of resistance, Gwendolyn delivered another nudge. “Remember Joshy, this is your decision. A big part of this will be learning to follow through on your commitments.“ She continued, “Otherwise… “ she let her voice trail off and cast a studied glance at the Sterncourt uniform still beckoning from the bed.
Increasingly caught in a trap of his own design, and knowing where the other path led, Josh’s spirits plummeted. The brief flicker of rebellion vanished, and his eyes dropped back to the floor. He again took painful note of his sissyish bralette and panties.
With a perfectly manicured index finger, Gwendolyn pushed Josh’s chin up until he was forced to study himself in the mirror. With her other hand, she held the hanger under his chin so that the girly garment was draped across the self-conscious teen’s body. “If this is to really work, you must make an honest effort,” she coaxed. “Take a good look honey, and tell me what you want,” she directed. Her words hung in the air for yet another interminable moment.
Josh peered at his reflection and paused. Then, in a downcast tone of surrender, he said simply, “Ok.” It was all he felt he could muster.
“OK what?” she asked, a tad too impatiently. She cautioned herself that this was a critical moment. She took an almost imperceptible breath.
“Josh, you must be clear about what you are asking,” she continued. “I need to make absolutely sure I know what you want to choose.” The possibility of Sterncourt still lingered like a weight on his chest.
During Gwendolyn’s conversations with Karen, they had concluded Josh needed to choose his new life as much as possible. She felt her role was to “help” him reach the correct choices. As Karen had put it, “Maybe it’s like a casino. It’s quite all right if he has a small victory now and then, but in the end the house always wins!” They had both laughed, but that was the plan. Gwendolyn intended to rig this game so the final outcome was never in doubt. A simple “Ok” just would not do.
“Mom…” he started uncertainly before she interrupted him.
“I think ‘Mommy’ is more appropriate now. It will help you break your old habits,” she continued. Although this was phrased as a suggestion, her firm tone made clear what was expected. “And certainly a ‘please’ is always nice too.”
The dejected teen had not called his mother “Mommy” since he was a small child. The moment overwhelmed him and he exhaled with a shudder. Josh’s next words came with little conscious thought, almost as though the girly boy in the mirror was speaking on his own. In a timid voice, Josh stammered, “Mo… Mo… Mommy, will you help me?” he asked, adding “please” as a hasty afterthought.
With a sweet and confident smile, Gwendolyn prodded her unsettled teenage son, “Will I help you what sweetie? Please tell me what it is you want.”
Josh winced. It wasn’t enough that he was doomed to be turned into a sissy. He had to ask for it? Swallowing hard and thoroughly chastened as his cheeks glowed their brightest red yet, he quietly mumbled his next words. “Mommy, will you please help me put on the dress?”
“Nearly there,” his mother thought with glee. She pressed her agonized son again, “Whose dress is it, honey?”
It was finally clear to Josh what she wanted to hear, and he was ready to say nearly anything to get out of this moment. The teenage boy’s next words were music to Gwendolyn’s ears. She would treasure them for years to come:
“Mommy, will you please help me put on my dress?”
Smiling broadly, Gwendolyn replied “Of course, sweetie! You only had to ask!”
The red-faced teen’s knees weakened as blood rushed to his head. Butterflies flew wildly in his stomach and his little man perked up yet again. His emotions swirled.