Jeff pulled into a parking space in the nice part of town and realized he had no idea what he was supposed to do. He had no errands to run, he doubted his mom had any to run (as she was on vacation), and there was plenty of food in the house. He got out of the car and started walking around aimlessly, marveling at his situation. He couldn't believe he was in a female body, much less his mom's. The two of them were roughly the same height, but she was a little thicker than Jeff, as he was pretty skinny for a guy and she was starting to lose her figure a bit. And, of course, she had the breasts, which jiggled slightly as Jeff walked down the street. He also thought it was so strange that he no longer had a penis; he could just walk around with nothing between his legs at all.
Without any better ideas, he wandered into an ice cream store. It was a nice day, after all, and he didn't have to worry about eating right as he was giving up this body in two weeks anyway. As he licked his chocolate marshmallow cone, he noticed the teenager behind the counter staring at him, and he realized he was viewed very differently by people now. He didn't recognize the guy working there, probably someone who went to another school, but he had never had the feeling before of a random stranger showing sexual attraction to him before. It really was different being a woman. It suddenly occurred to him that he could probably meet that guy after work and hook up with him. He pretty much just had to say the word. It was an odd thought, and he left the store right away.
As Jeff thought about the female body some more, he noticed Victoria's Secret across the street. Before, every time he had walked by he had surreptitiously snuck glances at the glamorous bras and panties in the window, and he had certainly never been inside. This time, he strolled right in.
"Hi, how are you, Mrs. Smith?" asked the bubbly girl behind the counter, who Jeff immediately recognized as Sarah Elliott, a year ahead of him in school. How his mom and Sarah knew each other he had no idea, but they obviously did, so he went along with it. "Great, Sarah, how are you?" he said. "I'm just looking for a few things to change up the wardrobe," he added, and Sarah nodded and said she was there if he needed anything. It was just crazy to Jeff that he could waltz into Victoria's Secret and start openly talking about bras and panties, and it would be totally normal. So he rolled with it. "Say, Sarah, what styles are in these days?" he asked. He didn't really care what she had to say, but she started walking around the store, showing off this bra or these panties and describing all these different aspects of them. She even started talking about her own preferences and at one point actually pulled down her top so that Jeff could see the bra she was wearing. It was one of the coolest things that had ever happened to him.
Eventually, though, another customer came in, so she left Jeff to browse the merchandise on his own. At first it was all too much, and he wondered if he should have paid better attention to her lecture. To keep it simple, he decided he would get one pair of panties and one bra, and he would get something colorful and shiny. Obviously he would have to explain this credit card charge to his mother eventually, but he had this body, so he figured he should go for it. Eventually he found a pair of sky-blue panties that matched the color of his dress really well, and nearby he found a bra that was the same color. He hadn't thought to check his mom's sizes before getting dressed, and for a moment he was stumped. Then he realized that he, like all women, could just take multiple sizes to the dressing room with him. Sarah showed him to the back and the first set of bra and panties that he tried on actually fit pretty well. He looked at himself in the mirror and thought he actually didn't look half bad for someone his age. He took the items off and brought them up to the register, where he used his mom's credit card to make the purchase. "Could I wear these out?" he asked Sarah, who smiled again and said "certainly." So Jeff went back to the dressing room once again, put on the cute blue underwear again, and then put his dress back on before leaving the store. It was funny, even though he didn't look any different, he really did feel better. He felt great, actually.
With the amount of fun he was having, he didn't want to go home quite yet. He kept walking around the shopping district until he came across Casey's Tavern. A bar. He had his mom's ID in his purse, not that he would need it, as she looked easily old enough to drink. Now he could just waltz into a bar like any adult. And why not? Sure, he couldn't drive after having a drink or two, but he could just Uber home that night and come pick up the car in the morning.