Biff was surprised with how fast he could run while pushing the buggy. He was making great time. He was turning a few heads as he ran, mostly men, who were staring at his chest. His pants were extremely tight which was showing his butt off to everyone too.
Jon was enjoying the ride. He was seeing new scenery and was getting some adoring glances from some women and girls that they passed. He felt his diaper growing warm and wet again as the run went on. He barely even noticed it at this point. It had just become another part of his day. He knew Biff would change him when they got home so he quickly forgot about it.
While Biff ran he took some time to reflect on his day. Everyone in work was super nice to him. A few of the men had been a bit flirty with him and most of the women were super nice to him. They had treated him like a member of their club. He had eaten lunch with a few of them, shared bathrooms with them and discussed some of the politics of the office, mostly about the men and how some of them spoke down to the women. He had a new appreciation for how hard women had it in life and had vowed to himself to do anything in his power to help the "other girls." "Other girls," he thought, "Am I really thinking of myself as one of the girls now?" With that thought he looked down at his breasts, held tightly by his sports bra but still jiggling a tiny bit with each step he took. Something had felt off about how he felt in work today. Sure, he was wearing womens clothes and had a big pair of boobs under his blouse. He had wider hips and his butt was bigger and rounder than ever before. But a part of him still felt tlike an imposter and it wasn't the part that was nestled tightly in his panties. He racked his brain trying to figure out what it was when he had a moment of realisation. He thought back to all the "other girls" he had interacted with that day and one major difference stuck out to him. All of them had makeup on, including lipstick and most were also wearing earrings. About half of them also had painted, manicured nails. He was starting to realise that a pair of boobs wasn't enough to make him a woman. Being and presenting as a woman meant a combination of a whole load of to her things too. He wanted to make the most of his new life and try to live it to his maximum potential. He figured, "in for a penny, in for a pound," and decided that tomorrow not only would he dress in women's clothes but he'd also try out some makeup and earrings.
He had soon completed the loop of his run and found himself back home. He pushed the buggy in the front door and released Jon from his seat. He decided to make dinner. He'd shower before bed. Biff again set Jon up with some TV to occupy him while he put dinner on. While dinner was cooking Biff went upstairs to take off his workout clothes. He put them in the laundry and rather than getting dressed again he just took a robe down from the hook on his door and put it on over his bare chest and the panties he still had on. It was just him and Jon at home now so why bother getting fully dressed again. He'd be showering before bed anyway. Biff grabbed a bottle of red nail polish and made his way downstairs to hang out with Jon before dinner. Jon was watching a cartoon and Biff sat on the sofa, smoothing his dressing gown beneath him as he sat. He crossed his legs and as he did the gown had fallen open a bit, showing off the full length of Biff's smooth legs.
Jon glanced back at Biff seeing him in deep concentration, applying nail polish to his fingers. He had his hand spread out in front of him in a very girly manner. Jon was amazed by what he saw. Biff's posture was very feminine. He had his legs crossed high above his knee and the upper leg was bobbing up and down as Biff focused on his hand. He was sitting up very straight and Jon could see his deep cleavage in the barely closed dressing gown.
