A boy decides to share a house with four girls while they all are going to college. They play a game called “Dare Poker” every Friday night, but how extreme will things get when the dares start rolling out?
Miles lugged his suitcase through the streets as he headed towards his new residence. He didn’t pack much, but having to walk a mile carrying his luggage was excruciating. If only he had his car, except it was unable to start and is in need of maintenance. The bus had to do for now, where the closest stop was off-campus and very inconvenient.
As he finally arrived to his destination, he was in awe at the size of the house he would be living in for the next year. The two-story building in front of him was huge, taking up almost a quarter of the block. Its magnificent white color made it stand out from the rest of the neighborhood, which was dull to say the least. This place was practically a mansion in a sea of nothingness. He sighed, thinking about how he ended up here.
Miles was in his third year of college. His university allowed students to live in the dorms for the first two years, so he never had to worry about his living situation. But the school kicks everyone out after their second year in favor of the new students, which made him on his own for the rest of his schooling. During the summer, he had applied to multiple fraternities, but he was rejected without reason, although it was probably due to his lack of popularity and extracurriculars. He also looked into getting in an apartment near campus, but the rent was crazy high.
When he thought all was lost, he ran into a student-made advertisement on the school’s website. The ad talked about the availability of a bedroom in an on-campus house, with the cost being the same rate as living in the dorms. Miles immediately replied to the ad, and the person who created it (someone named Felicia) responded in just a few minutes. She said that he would be the perfect addition to their home, and that he could move in at the beginning of the school year.
What wasn’t mentioned in the ad was that all of current residents of the house are college girls, 4 in fact. Apparently, Felicia’s parents own the place, and most of them have been living there since their first year of college. Felicia said that they haven’t had a male roommate before, and are looking forward for Miles to be their first. “I haven’t even made out with a girl, and now I’m going to be living with a bunch of them? This is going to be crazy!” he thought.
Coming back to reality, Miles knocked on the door of the house. In no time, a girl answered and it happened to be Felicia. She was soon hugging him and saying that it was nice to finally meet him. Within the first few minutes, Miles learned that his new roommates were super affectionate as he was also introduced to Madison, Elizabeth, and Trisha, who all greeted him with hugs. They seemed to be very friendly people, and Miles felt that he would enjoy his time here.
The girls gave him a tour of the place. On the first floor, there is a big kitchen, a living room, a dining room, a bathroom, and a couple of office/storage spaces. The second floor is where all of the bedrooms are, and each person has their own individual one. There are also two bathrooms, both with showers, bathtubs, and toilets, which sit in the hallway and are shared by everyone.
Once the tour was over, Felicia said that Miles could get his room set up, and that they could all hang out in a little bit. In his room, there was pretty much just a bed, desk, dresser, and closet, similar to the basic dorm room. Again, Miles didn’t have much on him, but it would be nice to get settled in. He put sheets on his bed, stowed away his clothes, and hung up a poster of his favorite movie. After he had everything finished, he went back downstairs to join the girls. They were all watching TV, and there was some random home renovation show on. Miles sat down on one of the couches and watched with them. During the show, he got to know his new housemates a little more.
Felicia is currently a junior, studying human biology; her parents are rich, which explains their ability to own this house. Madison, aka Maddy, is also a junior who is going towards a business major, and she is a pitcher on the school’s softball team. Elizabeth, aka Liz, is the third junior of the group; she is going to school for engineering and has an internship for a plane-manufacturing company. Trisha, aka Trish, is the only senior of the group, and will be graduating with a gender studies degree; she also runs a social activism group that is associated with the school. Miles didn’t really have much to say for himself, except that he is a junior and is majoring in sociology.
A few hours went by and it was soon almost midnight. Everyone was tired, so they all said goodnight and went to their respective rooms. Miles felt happy about how the day went. He thought that he would be more nervous or shy, but he actually felt comfortable being there. He wondered what the rest of the year would be like…
It was Friday, and classes were starting this upcoming Monday. Miles was hanging around the house when the girls started talked about some game that would be happening that night. When he questioned them about this game night, Liz said that this was something that they did every Friday night. She said that they play poker, but with a little twist of “Truth or Dare”; they called it “Dare Poker”. Since he was an official member of the household, he was invited to play, and he accepted.
The girls decided to have Miles sit out the first round, so that he could get an idea of what the game is like. It was practically just poker in the beginning, with everyone making bets and swapping out cards. When cards were revealed, Maddy beat out everyone with a straight and was deemed the winner of the round. Now, here is where things get interesting. Since Maddy won the round, she got to dare someone else of her choosing. She decided to dare Trish to drink a glass of month-old milk that was still in the fridge. Trish chugged it down like a champ, and she looked like she was about to vomit (but luckily, she never did).
Miles joined in the second round with the same number of chips as everyone else. The girls mentioned something about a surprise for the loser, but he brushed that comment off. Throughout the game, he thought that he was doing pretty well. He was only given one dare, which was to kiss Felicia. He actually enjoyed that, but both he and Felicia blushed afterwards, and it took a little bit before they got comfortable with each other again.
After an hour or so of the game, with no losers yet, Miles ended up with a really great hand: a straight flush. Since he knew that he could only be beaten by a royal flush, he decided to risk it and went all in. Most of the girls folded, but Liz decided to call and also went all in. Miles began to freak out a little, but he was still confident that he had the better hand. It was like slow motion as they laid down their cards for everyone to see. He surveyed Liz’s cards, and was thrown back at the results: a royal flush of hearts. He had officially lost.
The game continued on with everyone else as Miles wondered what his “surprise” was, since he was the loser. He assumed that it might be buying everyone dinner, or something to that effect. He didn’t have to think on that too long, though. It was no shock that Liz won, especially with her stockpile of chips after Miles’ loss. That was when he was told what he had to do.
The basics of the “punishment” is that the loser must take part in a week-long dare, chosen by the last person standing. One week’s dare would normally end after the following week’s Dare Poker game had finished. However, if the same person loses a second week in a row, that person will have a new dare, plus the original one. There is no limit to how many dares can be happening at once, but Trish said that the most anyone has gotten is two. All the non-losers would discuss ideas with each other, but it was ultimately up to the winner to choose the dare.
The girls huddled together to figure out what Miles’ fate would be. To be honest, he was a little nervous. He barely knew these girls, and even though they seemed nice, they could be very different when it comes to this game. After whispering to each other for about a minute, the girls separated and Liz stood up straight.
“After much consideration from the council, I have decided on your dare for the next week. You shall wear women’s panties of my choice until your punishment is over. Instructions will be relayed as soon as possible.”
Miles just stood there, mouth agape. What the hell had he gotten himself into?
“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.
Liz whispered something to Felicia, then said aloud, “Felicia is the one who will do your nails. She has the biggest nail polish collection out of all of us, which is why I figured that it was best for her to do it. She knows the colors I picked out, so you can go with her to her room to get started.” Miles did as told and walked with Felicia to her room.
Felicia’s room was pretty similar to Liz’s in style, except there were a few additional decorations to make the place more lively. She had a string of lights, a few posters, and photos on her mirror. It definitely seemed to fit with her personality.
Felicia told Miles that he could sit on her bed, which would make this process easier. She grabbed a big case out of her closet and opened it up. Inside of it was a bunch of nail polish bottles, each with their own unique color. There was also some tools often used in nail care, like a nail file, toe separators, and other miscellaneous stuff.
First, Felicia took out a nail polish bottle with clear liquid in it. “What I have here is a base coat. It’s just something I’ll be putting on all your nails so that the polish doesn’t stain your nails. It also helps the polish last longer, which I guess doesn’t really matter in your case, but I’m going to use it anyway.” Miles nodded as she had him stick out his hands. She unscrewed the bottle and brushed his fingernails with the shiny liquid, eventually doing the same with his toenails.
While that dried a little, Felicia grabbed the necessary nail polish colors. She had taken 3 bottles out; one was a red polish, one was a pink polish, and last one could not be determined by Miles, as the bottle was not see-through. “Those are probably the worst colors that could’ve been picked for me,” he thought.
Seeing the look on his face, Felicia tried to comfort him. “I know the colors are kind of extreme. Liz sometimes goes too far with these dares, but I think she just likes that there’s someone new to try and embarrass. Hopefully she’ll get tired of it soon enough. I’m glad you’re being a good sport, though. Most guys I know probably would’ve run when Liz mentioned the underwear.” He smiled at that as she prepared everything for the official start of his punishment.
She gave him the toe separators to use for his feet. “You should put these on so that you don’t mess up the polish or get it on your skin.” Miles did as such while Felicia grabbed the pink polish. This pink was very bright, close to a neon type of color. It was definitely a girly color, and it is unlikely that anyone else would see it otherwise.
Felicia screwed the top off of the polish and began to paint Miles’s toenails. One by one, his nails were coated with the pink color as she glided the brush over them. Although he wasn’t happy about the dare, the feeling of the brush going across his nails was an interesting sensation. After Felicia had painted all of his toenails, she went back and did another coat on each of them. Once she was finished, she allowed Miles to get a better look at them.
Miles had to hand it to her: she did a really good job on his toenails. Each nail was perfectly polished with the pink color, and he could not see any of his bare nail at all. It was kind of weird to see polish on his toes, especially since they have only been unpolished his entire life. Although he didn’t pay much attention to what his feet originally looked like, the polish definitely made them look different. He didn’t want to say this out loud, but he actually kind of liked it.
While his toenails dried, Felicia moved on to his fingernails. She grabbed the red polish and had Miles stick out his hands again. After taking out the brush from the nail polish bottle, it didn’t take long for her to start painting his nails with the cherry red color. It was pretty much the same process as the toenails, except this time, Felicia didn’t paint the nails on either of his ring fingers. Miles asked her why she was skipping those nails as she screwed the brush back onto the nail polish bottle.
“Liz told me that she wanted your nails to be as feminine as possible,” Felicia said in a somewhat somber tone. “So, she decided to be a little… creative. I am so sorry about this.”
In that moment, Felicia picked up the mystery bottle and took the brush out. Miles could instantly see what was in it: glitter. It seemed to be a silver-colored polish, except it was almost straight-up covered with glitter. His eyes widened, and he couldn’t believe that this was going to be on his nails. It didn’t take long for Felicia to put the polish on his two bare fingernails, officially making all of his nails painted.
Miles took a look at the nails on his hands; they were definitely a sight to see. Not only were they red, a popular nail color for women, but they also had the glittery accent nail, something that you would never see on a man. Unfortunately for Miles, he hadn’t cut his nails in a while, so the length of them really made things worse. Aside from a little hair on his knuckles, it would be hard to tell that his hands did not belong to a woman.
Miles praised Felicia for a job well-done, which brought a smile to her face. He did not want her to know, though, that her work was almost sending him into a panic attack. He was feeling very stressed on the inside, and had so many questions as to what would happen next. How would he get through classes like this? Will people begin to think he is gay? Can he even go out in public anymore?
Felicia, despite Miles’s attempts to hide his emotions, could definitely tell that something was a little off with him. To help distract him while his nails dried, she decided to get a normal conversation going.
“So, how have your classes been going so far? When you named off what you were taking, they sounded pretty cool.”
“It seems like they will be interesting classes. I’m usually not big on lecture-heavy courses, but once they got into the material they’ll be teaching, I was intrigued. This is probably because I am an only child and have not even had a girlfriend, and I guess learning about certain relationships is the closest I can get to experiencing them.”
“That makes sense. I have a big family, and it’s hard for me to imagine what not having that would be like. I get why you would want to explore that kind of thing, having those relationships is pretty nice.”
After a short pause, Miles inquired, “Can I ask you something? How is Liz so good at Dare Poker? She’s won both games since I’ve been here, and none of us ever came close to beating her.”
“Her dad was like the poker champion of North America or something, so she dominates this game. I don’t think she has lost once, and there have only been a select few where she didn’t get to choose the loser’s fate.”
“Wow, that’s intimidating. I’m surprised you all could get this far without the dares running so thin.”
“Believe it or not, the dares have been pretty good this entire time. Even after the most outlandish of dares, she was still rolling them out every week. Like I said, she can get really creative with this kind of thing.”
After they talked for a little while longer, Felicia checked Miles’s nails and felt that they were dry. She grabbed another bottle of clear polish out of her case and began to put it on all of his nails. “This is called a top coat. It’s just to make sure that your nails don’t get ruined. Hopefully this means that you won’t have to get them repainted, as Liz said they need to be perfect throughout the entire dare.” Once she had put the top coat on his nails, she put everything away and stored her case back in her closet.
Miles thanked Felicia for making him feel more comfortable with the situation. She smiled and said that it was no problem. He got off of her bed and left the room. Looking at his nails one last time, he gathered up the courage to go downstairs in his current state.
The moment he got into the living room, all of the girls asked to see his nails. Each of them gave many comments about how the colors and design looked good on him. They didn’t seem to care that the nails were on him, a guy (which is not very normal in society). He actually kind of liked the attention he was getting in that moment.
After the initial shock of things, the girls went back to watching their movie, as if everything was normal. Miles, along with Felicia, joined them in watching the movie. Once the movie was over, he went to his room and got into bed, falling asleep soon after.
After he showered and got dressed on Saturday morning, Miles realized that he had just put on his last pair of women’s underwear. He needed to do some laundry anyway, so he took his basket of clothes down to the laundry room. He had looked up how to wash the underwear and learned that it had to be separate from all of his other clothes. He stuck the underwear into the washing machine, set the cycle to delicate, and pressed start.
While those were washing, Miles decided to do some of his homework. He already had a paper to write, but luckily, it only needed to be a page long. He sat down at his computer and opened up a new Word document to get started. The topic of the paper is “Gender Roles”, which seemed like an easy thing to write about to him. As he typed on the keyboard, he couldn’t help but get distracted by his new nails. Although he initially didn’t like them, he was starting to become okay with them. His nails have been bare his entire life, and he figured that there’s not much harm in adding a little color for a few days.
After he had written most of the paper, he went to go check on his laundry. His underwear was done, so he put them in the dryer and added the rest of his clothes to the now-empty washer. Upon leaving the laundry room, he noticed that everyone was chatting in the living room now.
“Hey, Miles,” Maddy said, noticing him walk in. “We were just talking about going to the mall on Cedar Drive that just opened up, and we’re going to hang out there and maybe have lunch. You wanna join us?”
Miles thought for a moment, then said, “Sure, that sounds great!” The girls said that they would be leaving soon, so he hurriedly went back to his room to grab his wallet and shoes. That’s when he remembered that he had the nails. “Damn it, I forgot about these!” he said to himself. “I guess I’ll just have to make sure to keep my hands in my pockets the entire time.” He headed downstairs again and they all left in Trish’s car.
As they pulled up to the mall, Miles was feeling a little nervous. Even though he would try his best to keep his hands hidden, he worried that he would slip up and that people would take notice to his nails. He did have a group of girls who could defend him if anything happens, but that still didn’t really help with his confidence. Eventually, though, he sucked it up, stuck his hands into the pockets of his shorts, and walked in with the girls.
The mall was huge. There were over a hundred different stores, varying from fashion to tech to sporting goods. A food court also sat in the middle of everything. The mall at the moment was very busy, likely due to it having just opened. Maybe Miles wouldn’t have to worry so much if he will just blend in with the crowd.
The girls were really interested in going into the clothing stores. Obviously, Miles wasn’t really interested in that, but they dragged him into those stores anyway. They went to at least 5 different stores over the course of a few hours, where the girls tried on shoes, dresses, tops, and a bunch of other things. They continued to ask for Miles’s opinion on what they wore, but he really didn’t know what to say when they asked him that. They even went into a lingerie store at one point, which made him even more uncomfortable.
After they were done with their shopping, they went to the food court to get some lunch. Since there were so many choices of food, each of them split up to get their own stuff. Miles decided on a sandwich place and got a turkey club with a drink. He was the first of everyone to get his food, so he found a spot for everyone to eat at. He specifically chose a more secluded area, as he was still reserved about people seeing his nails. The girls found where he was sitting and they all ate together. They chatted like normal, and Miles really felt like a part of the group at this point.
It wasn’t long before they decided to head back to the house. Nobody had noticed Miles’s nails (at least, nobody mentioned them), which made him relieved. “Hopefully classes will go as smoothly as this experience,” he thought.
Once they arrived at the house, Miles changed out his laundry. After putting his regular clothes in the dryer, he brought the women’s underwear into his room, folded them, and stuck them in his drawer. He then went back to doing his homework, and it didn’t take long for him to finish up his paper, which he promptly submitted online. He browsed the internet while waiting for the rest of his clothes to finish, and upon them finishing, took them out of the dryer and put them away.
For the rest of the day, Miles hung out with the girls downstairs. It was mostly just talking while the TV was playing in the background, but he still enjoyed himself. They pretty much just did that until around 1 AM when they all felt tired. They all wished each other a good night and went to their respective rooms. Miles got changed into his pajamas and slipped into bed.
“Maybe this whole dare thing isn’t as bad as I was imagining it would be,” he thought as he drifted off to sleep.
Miles had to be up early again to get ready for classes. He showered as normal and got dressed, again putting on one of the pairs of panties. He went downstairs to get breakfast and talked a little with the girls, who were of course ready at this time of day. After he had finished eating, he headed off to class.
As he walked to his class, he worried about what people might say about his nails. Since it was college, people probably didn’t care, but Miles was still nervous. He decided to do the same thing that he did in the mall and keep his hands in his pockets as much as possible. But he did have to take notes in his classes, so he couldn’t hide them the entire time. In his classes that day, things went pretty smoothly. Nobody ever made fun of him when he had to have his nails out of his pockets. He actually got a few compliments from some of the girls in his classes, which gave him more of a confidence boost.
Miles was nearing the house when he saw a random car in the driveway. Thinking nothing of it, he walked through the door and into the living room. Before he was able to walk up the stairs, he ran into Felicia. She was standing there with a grown man that he did not know.
“Hey, Miles,” she said, “I’d like to introduce you to Brian Walters, Liz’s father.”
Miles looked at the tall, bearded man, who was holding out his hand. They shook hands, and Brian said, “It’s nice to meet you, Miles.”
Curious as to why he’s here, Miles asked, “So, are you visiting Liz or something?”
Felicia chimed in and said, “Actually, I called him here. After our chat the other day, I realized that I was tired of Liz winning all the time. So, I decided to bring in the expert who taught her, and have him teach us!”
Noticing Miles’s nails, Brian said, “I can already see my little girl has done a number on you. She definitely can get a little competitive, and she brags a lot about winning these games. I’m happy to help the both of you out.”
“That’s great!” Miles exclaimed. “Won’t Liz be mad about this?”
“She still has class for a few hours, so we’ll be able practice the next couple of days without her knowing,” Felicia said.
“I guess we can get started, then!”
With that, they got out the poker set and began training.
Throughout the week, Miles continued going to classes with his nails painted. After his experience on Monday, he began to feel less self-concious about them, so by the end of the week, his hands never went into his pockets. He got more compliments from his classmates, and he even became more talkative in class. He actually made a few friends, something that has been hard for him before. Miles suspects that his new friends think he’s gay for very obvious reasons, but he can correct them if it ever comes up in conversation. If they ever catch a glimpse of his panties, that might be hard to explain away.
Every day that week after classes, Brian went through the entire crash course of poker with Miles and Felicia. Although Trish and Maddy couldn’t be there for the lessons, the information was passed along to them as best as possible. They learned about poker faces, betting wisely, and even getting into analyzing which cards might be left in the deck. It was all very educational, and everyone was excited that they might get a handle on Liz for once. Miles and Felicia bonded during these sessions, whether it was the shared passion to win, or just spending a lot of time together.
On Friday afternoon, before the next Dare Poker game, Brian had just finished that day’s lesson. Although they weren’t experts at the game, this was the best they could do for now. If this didn’t help them get the upper hand, they didn’t know what would. As Brian was leaving, he bid good luck to everyone and started to walk out the door. However, to the surprise of everybody there, Liz was standing the doorway. She had come back early from class, which they later learned was because her professor had a family emergency.
“Dad, what are you doing here?” Liz asked.
“Oh, um… I was just coming by to drop off some stuff from your mom. I didn’t want to disturb you, so I tried to be in and out quickly.” Brian had made a good excuse.
“You could have said something, it wouldn’t have bothered me!” she said, seeming to buy into the lie. “We can go out to dinner or something… wait, are those your poker supplies?” Brian said nothing and stared at her. “You were teaching them, weren’t you? Dad, I told you not to get involved! It’s our game and you’ve intruded like you always do!” She stormed upstairs and slammed her bedroom door closed.
Everyone stood there awkwardly before Brian broke the silence. “Well, I better go. She’ll get over it, she always does.” He jumped into his car quickly, seemingly afraid of Liz, and drove off. Miles and Felicia closed the front door behind him, and they both had a worried look.
“It looks like we’ve been found out,” Miles said. “What do you think’s going to happen?”
Felicia sighed, then said, “We broke no rules of the game, so what we did was just a little unethical. Brian’s right about her anger being temporary, but she’ll still be mad during our game. Who knows what she’s capable of.”
They went upstairs to see if they could apologize to Liz. But as they approached her room, the door was closed and locked. They could hear muffled yelling through the cracks, Liz was obviously pissed. It sounded like she was talking to her mom, something about her childhood and her life being in ruins. Felicia decided it was best not to get involved, and she decided for them to go into her room for the time being. They laid on the floor of Felicia’s room, and they just talked to pass the time. At first, it was about Liz and what might happen at Dare Poker that night. Then, when childhood was mentioned, the conversation spun out of control. They chatted about what their lives were like before college.
Miles’s family was definitely lower class. His parents worked two jobs each to help put him through college, and even before he started school, they still scraped by. He usually had a job in the summer to contribute, and sometimes took on a part-time gig during the school year if he felt that classes were easy. He was grateful for what his parents were doing, as they were getting him towards a better life.
Felicia had a vastly different childhood. Her parents were very wealthy, so it was no wonder that they could afford this house, plus many others. She didn’t really see her parents often, though. They often went on business trips and exotic vacations, while Felicia was watched by one of the many nannies she’s had over the years. Her parents were emotionally distant, and although she is glad that they provided her with luxury, she wanted to actually have a mom and dad active in her life.
All caught up in their chats, time had flown by; it was time for Dare Poker to start. They walked downstairs and went towards the table, where Trish and Maddy were already seated. They sat there for a little bit, wondering if Liz was going to come down. Before Felicia got the chance to go up and check on her, she appeared from the stairway. She seemed to be okay, other than the fact that there was a glint of anger in her eyes. She sat down, and they began to play.
In the beginning, everyone seemed to be close in skill level. Although Liz had a lifetime of poker training under her belt, the recent crash course gave the others a boost this time around. They now had the skills for the competition to at least be somewhat fair. For a while, very few chips were lost from any single player, and nobody was close to losing yet. Everyone saw the frustration that Liz showed, but they tried not to falter in their playing.
After about an hour into the game, everything began to change. With some bad luck, Miles was getting the worst hands. It felt like he was only getting pairs left and right, no matter how hard he tried to avoid it. Any time he got a good hand, one of the girls would have a better hand. His chips began to die away, and there was nothing he could about it. He was able to last a lot longer than he normally did. But, unfortunately for him, he couldn’t hold on, and once again, he was the loser of the night.
There was still some hope left. Miles learned from Brian’s training sessions that Felicia was actually really good at poker. She caught onto things easier than he could, which could also be seen when comparing their class grades. She was the one who won most of the time in their practice games, and Brian had a lot of confidence in her. Since Miles had failed, Felicia was their best hope at ending Liz’s reign of power.
After another hour from Miles losing, nobody else had dropped out of the game. However, after one wrong move, Maddy lost all of her chips and was down for the count. After a few more minutes, Trish was also out. It came down to Felicia and Liz battling one-on-one. The competitors had an even number of chips between them, so it was anyone’s game at this point. For the first couple of hands, Felicia beat Liz’s cards by a landslide. After a few smaller defeats, a fire came into Liz’s eyes, and she stepped her game up. They went back and forth between winning and losing each hand, but Liz was starting to get ahead. Felicia started to look a little bummed, but Miles cheered her on to get her confidence back up. Liz glared at him every time he cheered.
For well into the evening, the match continued on and on. They were still about even in chips at this point, with little change happening. Felicia, along with those who were out, were clearly very tired; however, Liz was still very fired up. In her tired state, Felicia was starting to lose more and more of her chips. However, before all hope was lost, Felicia got a straight flush. Whether this was just because she was tired, or a purposefully risky move on her part, she went all in on this hand. Liz called this bet.
Everyone was practically biting their polished nails as the cards were revealed to each other. Liz, in a stroke of luck, had a royal flush, beating out Felicia’s straight flush. Liz was the victor again. A wave of disappointment flooded the room. The losers looked at each other with sad looks, questioning what was going to happen now. Liz took a deep breath, and began to speak.
“I cannot believe you all, going behind my back like this. My father, the man who taught me all of my poker skills, stepped into this house and secretly taught you, too. We never said this wasn’t allowed, but after all this time together, I figured that we were at a point where we trusted each other. This means not getting our families involved in our lives, especially with this, since Dare Poker is meant to be just for us. However, it is clear we have different boundaries.”
Liz paused for a moment, then continued on. “I have become aware that Felicia was the one who called my dad. I’ll admit, she’s learned well from him, based on this past game. But it is obvious that she is the main conspirator in this ‘protest’ against me, which gives me great disappointment. Since Felicia and Miles have not been very subtle in their feelings for each other, I believe that the best way to punish her is to punish him. So, Miles, as the loser of this game, you will be getting a full treatment at the local beauty salon. This means that you will get a more feminine mani-pedi, your makeup will be done, and worst of all… your whole body will be waxed, top to bottom. And Felicia gets to watch it all happen to you, at each painful second.”
With that, Liz stood up and walked away. Everyone just looked at each other in awe. Miles was so screwed.