“This can’t be happening,” Miles thought. “I have to wear women’s underwear for a whole week? There’s no way this is real life.”

Liz had Miles follow her upstairs and led him into her room. She went into her closet to search for something, and as she did, Miles looked around the room. It was practically the same as his, except she had a frilly pink bed and a big mirror on top of her desk, which had an array of makeup in front of it. After looking through her closet for a little while, Liz popped out with an unopened pack of panties.

“Luckily, I never had the chance to break into these,” she said. “They should fit, I think we are about the same size. You will need to wear a different one every day, so this variety pack is helpful in this case. Please change into one of the pairs now. I’m going to be inspecting you every morning to make sure you’re wearing them. In this house, we like to be truthful with each other, and I hope that you will do the same.” Miles nodded in response and took the pack out of Liz’s hands. He then went to his room, closing his door behind him.

Before he opened the pack, he looked at everything that was in it. There were 9 pairs of panties, with 3 types of panties ranging over 3 different colors: red, pink, and light blue. Miles couldn’t name the kinds of panties, but they all looking revealing and uncomfortable. He couldn’t really avoid anything that didn’t look girly, which didn’t help his situation. He tore open the pack and took out the least girly pair. Surprisingly, the material was very soft. The pair was blue and probably the closest to his male underwear. The tag said they were called “boyshorts”, which kind of made sense to him.

Miles then stripped so that he was naked from the waist down. Hesitantly, he stepped into the girly underwear and slowly slid them up his legs; it surprisingly felt good. Once he got the underwear in place, things felt a little tight. His penis wasn’t very big to begin with, but it was still getting in the way on wearing this underwear comfortably. He readjusted himself so that Little Miles was in between his legs. Only then did the panties fit well, even though he now had a flat front, with no evidence of a penis in sight. At this point, he was more girl than boy down there, especially with his unmanly figure.

Sighing at his new look, he put on his pants again and went back into the hall. Liz was standing right there, and instantly ordered Miles to turn around. He did, and she slightly pulled down his pants to get a good view of his new underwear. “Nice work. I was hoping you would pick out a thong, but I guess I’ll have to wait on that,” Liz said in a hopeful manner. They both then went downstairs to hang out for a little while. None of the girls teased him about the underwear (if they even noticed), so he was glad that they are at least civil about some things. Who knows what the rest of the week will be like, though, right?

The day is Monday, and classes are starting today. The weekend had come and gone, and Miles had the chance to get to know everyone better, which he was glad about. So far, he has had no issues with wearing the panties. None of the girls even talked about it, except for when Liz had to make sure he was wearing them during her inspections.

He had a 9 AM class, so he was up earlier than he liked to get ready. After he showered and everything, he needed to pick out a new set of underwear. Miles had made the mistake of using up the boyshorts type of underwear during the weekend, and he now had to get through the school week with underwear that could only be seen as women’s. The choice was between a V-shaped pair (what he now knows is bikini) and a thong (as Liz pointed out on Friday). Since he is still not brave enough yet for the thong, he opted for the bikini.

He grabbed the red bikini pair and examined it a little. There was a lace trim along the waistband of the underwear, featuring a nice design of roses on it. The rest of the underwear was made of satin, which felt better than whatever material the boyshorts had. It was undeniably made for women, but it could be a lot worse.

Miles was initially hesitant to put on the pair, but that feeling soon went away once he slipped it up his legs and let the satin embrace him. This underwear was like nothing else he had ever worn before, it felt so damn good. It was erotic, and empowering, to say the least. He had to somewhat tuck himself again for the underwear to fit more snuggly, but it was seemingly perfect nonetheless. Looking in the mirror, he actually smiled a little at what he was wearing, which he instantly felt weird about.

Eventually, he put on his clothes for the day and left his room, going to the kitchen for some breakfast. Surprisingly, all of the girls were up and ready themselves. Most of them had already eaten and were pretty much just talking to each other.

“Do you guys have morning classes, too?” Miles asked.

“Nope,” Maddy said, “we’ve just got to be up early like most girls to get ourselves prepared for the day. Also, we really like to chit-chat before our classes start.”

“By the way, Miles, it’s time for inspection,” Liz chimed in. Miles reluctantly turned around and Liz pulled up the waistband of the panties. “Very good. I knew you had to be out of boyshorts by now.” Miles blushed and got himself a banana to eat.

While he ate, he joined the girls’ conversation on their classes for the semester. The majority of everyone’s classes had to do with their major. Trish had courses related to women in media (movies, literature, etc.). Felicia was taking multiple sciences, even ones unrelated to biology. Liz did hands-on labs, which apparantly dealt with creating things from scratch. Maddy had both math and public speaking courses under her belt. And finally, Miles had classes about relationships, family, and other forms of social interaction, all of which tied into a key theme of diversity.

Noticing that the time was 8:45, Miles excused himself, grabbed his backpack, and headed off to class. Like most colleges, his schedule depends on the day, where he has two classes on Mondays, Wednesdays, and Friday, and two entirely different classes on Tuesdays and Thursdays. Today, his two classes were back-to-back, so, although he had to get up early, he had the entire afternoon to himself.

The first day of classes was mainly about what to expect from the course, which was nothing too interesting. Although Miles originally wasn’t looking forward to the classes today, he seemed to be the only guy in both of them, so he couldn’t really complain about getting to be around a bunch of girls for a couple hours every day. He would soon learn that his Tuesday/Thursday classes were also like this. He didn’t realize this in his first two years, but sociology at this school is not really popular among men, with about 95% of sociology majors being women.

After classes had finished, Miles had a quick bite to eat and headed back to the house. Once Miles stepped foot inside, it dawned on him that he had gone through both classes while wearing the women’s underwear. It’s likely that he was so distracted that the thought never entered his mind. Or maybe it was because he was actually getting used to wearing the panties. Whatever the case, he didn’t really care because nobody even noticed.

Miles decided to spend the rest of the day relaxing in his room. After a while, he looked at the package of underwear, and he wondered what he was going to do the rest of the week. He wanted to avoid the thongs as much as possible, and luckily, he only had to wear 2 (assuming he doesn’t lose the next Dare Poker game). He decided that he would rip off the bandage and do one early in the week. The other would be done on Friday so he could have some courage during game night. He went to sleep thinking about it all, and knew that this was going to be the craziest week he’s ever had.

The week had gone by faster than Miles had expected. He was liking his classes, which had contributed to time flying by for him. He hated to say this, but he got used to wearing the women’s underwear. In the back of his mind, he actually favored this underwear over his male underwear, something that he doesn’t want to admit to himself yet.

Anyways, it was Friday, and tonight, Miles wanted to make sure that he didn’t lose again at Dare Poker. He told himself that, as long as he did not make rash decisions like the last time, then he would do fine. With a red thong on under his clothes and a new attitude, he went downstairs to join everyone for the game. Once he got downstairs, he ran into Felicia.

“Hey, I just wanted to wish you good luck,” Felicia whispered. “I know how much it sucks to lose and have a week-long dare. I’ve had my fair share of them, so don’t feel too bad about one loss.”

“Thanks, Felicia. I needed that encouragement,” Miles whispered back.

“Just be careful out there. All of us are really good at this because we’ve done it for so long, but I know you’ll catch on eventually. See you out there.” Felicia then walked over to the poker table and sat down, with Miles doing the same not long after.

The game started as usual. Miles stuck to his plan and was conservative about his chips. He did not use too many on bad hands, and only raised in minimal amounts with better ones. He had a good strategy, and it was on par with what most poker players do.

Unfortunately, however, Miles was not having the best luck when it came to the cards. As the dares rolled out and his chips depleted, he couldn’t get more than a straight or a three-of-a-kind. Everyone else was doing good and playing normally, while Miles barely had any chips to show for himself.

Once he got down to only a few chips, Miles felt that all hope was lost. But then, the cards were drawn for the next round. He took a look at his cards and saw that he had a full house. This was the best hand he had been given today! Although it wasn’t as great as it could be, he felt confident that this would be his shot at redemption.

Miles was forced put his last remaining chips into the pool and waited for everyone else’s moves. Nobody folded, so it was time to reveal cards. Miles was the first to lay his down, and the girls were surprised at his hand after the awful game he’s been having. Everyone else followed suit with showing their cards. Maddy had a two pair, while Felicia and Trish only had high cards. Seeing the look on Liz’s face, he thought that he had her beat, too. She flipped over her cards and Miles could see everything clear as day: she had 4 jacks. He lost again.

He just couldn’t fathom that he had lost two times in a row. While everyone else kept playing, he worried about what his next dare would be. It was going to be paired with his current dare of wearing women’s underwear, so whatever the dare was, it would likely amplify the embarrassment of that. After about an hour, Liz was deemed the winner again. The other girls were about to huddle up with her, but she stopped them.

“There’s no need for that. I’ve already made my decision on the dare.” Oh boy. Liz continued, “I have decided that, along with his current dare of wearing women’s underwear, Miles must have nail polish on both his fingers and his toes. The nail polish colors will be chosen by me shortly.”

“I have to wear nail polish now? This is insane! How am I supposed to get through this?” Miles thought to himself. He just went numb, unable to comprehend what was going to happen to him.