Somehow, Drake had made it through his first day, more and more of his memories filling in as the day progressed. By the end of the day, he was completely comfortable with responding to the name Tess, didn't think twice about using the girl's lavatory if the need arouse and when he had been approached by a boy and asked to the upcoming spring dance, who he turned down, he didn't even give another thought to the idea that he was being treated like a teenage girl.
But when Cecilia announced, "Let's go shopping," Drake balked, unsure suddenly.
Seeing his hesitation, Cecilia commented, "Come on, Tess. I need a couple things and you can't wear your normal boxer's underneath the dress my cousin picked out. It just wouldn't look right," and taking Drake's hand, Cecilia added, "Please? For me?"
Feeling like he was possibly getting in over his head, Drake hesitated for a moment, but after a couple seconds told her, "Okay."
As Cecilia showered him with her thanks, Drake thought, "It's not wrong for me to wear girl's underwear? Is it? Especially if I am indeed turning into a teenage girl?" and turning these questions, among others, over in his mind, Drake hitched up his backpack and began to walk with Cecilia down to the city bus stop.
Switching buses at the transit centre, Drake found himself torn between the prospects of wearing girl's underwear. On one hand, he felt that it was right, but on the other, he felt more comfortable wearing boxers and wondered why it was that he couldn't, despite what Cecilia had said about it not looking right. Following his best friend into a store aimed at the selling clothes to the teenage girl, Drake began to peer at the different selections and the longer he looked, the more comfortable he felt as his hesitancy about how perverted it would be to shop for girl's slowly faded.
"I think you'll look cute in these," Cecilia suddenly announced and glancing in the teenager's direction, Drake saw that she was holding up a very tiny pair of panties.
Taking them from her, Drake noted that the waistband that went around was pink, the front and area between the legs was a soft, creamy white colour and the appeared almost translucent in front, while the back consisted of a simple white stretch of white fabric that would fit between the butt cheeks. Understanding that what he was holding was called a thong, Drake sputtered, "I can't wear this," and tried to hand it back to Cecilia, who smiled and told him, "Sure you can. It's your size and you'll look cute in it."
"But what about the part that is supposed to be covering my butt," Drake whispered.
Cecilia started to giggle slightly, and covering her mouth, she whispered back, "It's not supposed to. Trust me," and pushing him gently toward the changing rooms, she said, "Try it on. I'm sure you see how great they look and feel once you have tried wearing them."
Not really wanting to try them on, Drake sputtered out a few more feeble remarks before consenting and allowing Cecilia to pushing him into the stalls for changing. Pushing the door closed, Drake dropped his backpack on the floor and after a thinking about it for a couple minutes, opened the door and pushed it out, asking Cecilia, who was standing on the other side, "Could you watch this for me?" as he did so.
Closing the door again, Drake looked into the mirror, taking in the fact that he still looked like a thirty six year old man, but appeared to be slimmer than the last time he had gazed into a mirror. Sighing, he kicked off his shoes and shrugged off his pants and boxers. Naked from the waist down, he though that something was off about his genitals and after staring for a couple minutes, he realised that the pubic hair that had disappeared from his chest had also disappeared from around his penis and testicles and that the disappearance was slowly working its way down.
As he held up the underwear Cecilia insisted that he try on, noting that there was a strip of paper inside, Drake muttered, "I can't believe I am doing this," and squatting down, making sure that he penis and testicles would up tucked between his legs, he pulled on the panties.
Adjusting them, Drake gazed into the mirror, marvelling at how flat his crotch appeared and how feminine he appeared, but at the same time upset that they sat so low and barely covered anything. Figuring this must be normal, he turned about and peered at his butt in the mirror, finding himself liking how the strip in back hugged the crack between his cheeks and didn't fully enter, knowing that would change probably the moment he sat down.
A knock on the door suddenly brought him out of his reverie and grabbing for his pants, forgetting for the moment he was wearing a pair of underwear that wasn't his, he listened as Cecilia called through the door, "Everything all right?"
"Yeah," he replied and throwing his pants aside, he reached up for the waistband, but stopped when Cecilia asked, "Mind if I take a look?"
A feeling of wanting to pose before the teenage girl swept over Drake and suddenly feeling like a pervert, both for the way he was feeling and for what he was wearing, he hastily called out, "No. It's okay..." but stopped in mid-sentence as he watched the doorknob turn and the door begin to open.
Realising that he had forgotten to lock the door, Drake made a hasty grab for his pants, and missed, as Cecilia quickly stepped into the stall and shut the door behind her. Seeing what Drake was grabbing for, she smiled and commented, "There's no need to do that. Besides. I want to see how you look," and grabbing up his pants, she began to look him over.
Excuse after excuse crept into Drake's mind and after a moment, he asked, "Who's watching over out backpacks?" when it became apparent that Cecilia had neither his nor her pack.
"The clerk up at the front of the store insisted she hold onto them," Cecilia commented in a distracted voice and looking Drake square in the eye, as she handed him his pants, she stated, "Really, Tess. I don't understand why you don't wear panties all the time. Why you wear boxers. You are so cute. You should wear them more often."
Shrugging, unsure what he should say, Drake took the offered garment and dropped it on the seat as he commented, "It's just that I find boxers more comfortable," and reaching for his boxers, he began to pull off the underwear, no longer caring that Cecilia was in the same room with him.
"I'm going to buy these for you," Cecilia said and exiting, she added, "These and a couple other pair that I think you'll look cute in."
As she left, Drake gazed back into the mirror one final time and after a moment's thought, pulled the door closed slightly and lifting up his shirt, he noted that his breasts where more pronounced and had clearly gone from an AA cup to an A cup. Feeling this was pretty normal, Drake dropped his shirt, which brushed against his for extra nipples and caused a shiver to go through him. Wondering about the four extra nipples, and how they hadn't developed, Drake exited the changing room.
"Everything all right?" Cecilia asked as he exited and nodding Drake told her, "I think I am going to need a couple new bras," all without missing a beat as he headed toward the wall and table with the bras.
Going through the various garments, Drake thought about what Cecilia had told him when she had commented how cute he had looked, but the immediately shrugged it off as the feeling of wanting to be naked in front of the teenage girl came over him. Selecting seven different bras, each in his size and without any underwire, Drake took the garments up to the front of the store, slightly amazed at how far his transformation had gone and how he was buying bras and thinking about things the way a teenage girl normally would.
Putting his purchases inside his backpack, he looked about for Cecilia and spying her waiting for him outside the store, he headed toward her. As he approached her, she asked, "Ready?" and nodding, Drake explained, "Just have to go home for a couple of things before I come over for the weekend," as he shifted his backpack so that it was sitting comfortably on his back.