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.

Due to the global pandemic, everyone is forced to stay at home until things have died down. This was great news for Jonah and Kelly, because their jobs continued to pay them, even though they can’t work from home. The couple decided to spend more time together, and they were loving it.

After a couple of weeks, though, they had gotten kind of bored. They were caught up on their shows, they had played all their board games multiple times over, and there was only a limited amount of times that they could have sex. Although this was initially a dream come true, that idea faded pretty quickly.

One night, Kelly suggested something out of the blue: Truth or Dare. She apparently loved it as a teen, and wanted to try it out again. Jonah agreed to play, as he hadn’t before and thought it might be fun. They decided that, since they weren’t going to work anytime soon, their dares were going to be more long-lasting than normal. Neither of them really knew what the dares would be, but it made things more exciting.

They started off with some truths, even though they knew mostly everything about each other. After a few rounds, it comes back to Jonah, and he chooses dare. Kelly thinks for a moment, and says, “I dare you to only wear my clothes while in this house, at least until the pandemic is over.” This wouldn’t be hard to do, since Jonah and Kelly were very close in size. Jonah hesitated for a moment, but knew what he had agreed to, so they went to their bedroom to pick out the clothes for him to wear. Kelly grabbed a pair of pink panties and a matching babydoll, handing them over to Jonah. He put it all on, and they went back to the game.

Jonah felt a little embarrassed in what he was wearing, but Kelly didn’t seem to care at all. They played some more rounds, with Kelly being dared to only take cold showers for the rest of the pandemic. It got late at a certain point, so they decided to go to bed. It was weird at first laying in bed in the babydoll, but Jonah got used to it and soon fell asleep.

Jonah was wearing a pink tank top and black miniskirt as he cooked dinner for him and Kelly. The pandemic still raged on, and the couple continued to do their dares from the Truth or Dare game a few weeks back. It took a while for Jonah to get used to his new wardrobe, especially the bras, but he was feeling more comfortable in it with every day that passed.

Kelly, feeling bored again, decided that they should play another round of Truth or Dare. Jonah agrees, so after dinner, they sit on the living room floor and start the game. They didn’t want to do any dares right off the bat, so they start with some minor truths. Kelly asks if Jonah liked his clothes, and he said yes, but didn’t want to appear too happy about it. He then asks her if his dinner tonight was good, and she said, “It could’ve used some more spice, you’re a little weakling when it comes to that.” They both laugh and continue on.

After a few more truths back and forth, Kelly picks dare for herself, and Jonah decides that, since he was wearing her clothes, it would be proper if she also wore his clothes. She agrees and they both go to the bedroom to get her new outfit for the night. Jonah just gave her a pair of boxer briefs and a Metallica t-shirt, since that’s what he normally wore to bed. Kelly changed out of her female clothes and dressed into the male clothes. She still looks hot, Jonah thought as they went back to the living room and kept the game going.

As the night died down, Jonah decides on a dare to end that evening’s game. Kelly is very quick to say, “I dare you to keep your entire body smooth and hairless!” He hesitates, but eventually sees no harm in it, so he agrees to do it. Kelly drags him into their bathroom and gets out all of her hair removal supplies. She spreads wax across every inch of his body, even putting some on his face. Little by little, she rips the hairs of his body out, with Jonah wincing in pain each time. After all was said and done, he practically had no hair on him, except for his eyebrows and on the top of his head.

Kelly then grabs her rose-scented lotion and rubs it all over Jonah. Believe it or not, he got turned on from her doing that, and she definitely noticed. “Oh, you like that?” she cooed. “Get into your pajamas, we’ll make this a little more interesting.” Jonah obliged and puts on a little red nighty that matched with his panties. As he lays on the bed, Kelly comes in with more of the lotion. She begins to rub it into his skin again. She watches his member slowly getting bigger inside his panties. She hikes up his nighty, and plays with his penis through the panties while still rubbing his smooth skin. In no time, Jonah’s eyes roll back and he has an amazing orgasm. They both just lay there in bliss for a few moments.

As they get ready to go to sleep, both of them just think about what this game has done to them, and wonder what will be next.

Another week had passed, and Jonah and Kelly were still playing their little game as the pandemic continued. Jonah was wearing a cute red sundress that day, while Kelly wore some cargo shorts and a flannel shirt. Jonah’s body was still hairless from the waxing, and Kelly made sure that he lotioned himself everyday to keep his skin soft.

Even though they weren’t bored, they chose to play some more Truth or Dare for the fun of it. They had run out of truths at this point, so it was mostly just daring each other to do random stuff, like putting a bunch of marshmallows in their mouths, or sitting and peeing on the toilet backwards.

When they get to their final set of dares, however, that’s when they each bring out the big guns. Jonah dares Kelly to take off her nail polish and to make her nails short. Kelly always wore nail polish and kept her nails really long, so Jonah felt like this would be a tough one for her. Plus, the colors she often chose were not very flattering, so he thought that bare nails would look better. Kelly sighed at this, but agreed to do it. She took out her nail stuff and used the nail polish remover to take the color off of her nails. Then, she used a nail clipper to cut the nails down to a very short length.

Now, it was Jonah’s turn, and he chooses dare, as expected. Since she was feeling a little vengeful, she dared Jonah to paint his nails a different color every week, and to keep his nails long and rounded. Jonah’s nails were already long after not cutting them at all during the pandemic, and apparently, they were going to stay that way. Kelly showed him how to file his nails into the rounded shape that she was asking for. Then, she had him pick a nail polish color from her vast collection. Since he didn’t want any of the unflattering colors that Kelly often wore, all he was left with were ultra-feminine colors. He decided on a pearly white color. Kelly instructed him on the nail painting process, having him put on a base coat, then 2 coats of the color, and a top coat. He did it as best as he could, and soon, both his fingernails and toenails sported the white polish.

While they waited for his polish to dry, the couple decided to watch a few episodes of a TV show that they’ve gotten into during the pandemic. Jonah couldn’t help but keep looking at his nails, as they made his hands and feet look like a woman’s. He kept trying to touch Kelly as they watched, but she kept reminding him to not ruin his nails. After they were done watching TV, they changed into their respective gender-swapped pajamas and went to bed.

---

To be continued…

My name is Leo, and I am going to tell you the story of how I explored my feminine side.

My dad died when I was only 2. I was too young to even understand what happened, so I wasn’t really affected by his death. But my mom and my sister, Jenny, who was 5 at the time of his death, were heartbroken. The summer after my dad’s death, my mom decided that they would go on a girl’s trip for a couple weeks, as they needed a little break from grieving. After this trip, they decided that it would become a tradition to take place every summer. My story starts at the beginning of one of their trips when I was 18.

Day 1

I always love whenever my mom and sister leave for their trip. Having the house to myself is great, even though I don’t really do much. I helped Mom and Jenny put their suitcases in the taxi. They said their goodbyes, and of course, Mom said not to get into trouble, and everything else a mom has to say when leaving her kid home alone. They then got into the taxi and left for the airport.

The day started out like most days did whenever they are gone. I watched TV, played some video games, normal teen stuff. As time passed, I got a little bored, and decided to walk around the house. I was about to pass Jenny’s room, but I suddenly stopped. Jenny never lets me in her room, it’s practically forbidden territory. I hadn’t even thought about it before, and I decided that this was my chance to explore her room.

As I entered, I could tell that it was a very girly room. Pink walls, frilly pink bed sheets, and big closet full of clothes. The whole room was just really big. She even had her own bathroom, a luxury I did not have. I saw that she had a vanity with all of her makeup on it. Glancing at it, I saw her nail polish collection.

Jenny has always been a lover of nail polish. She has her nails painted 24/7, I rarely see her with bare, or even slightly chipped, nails. It always looks nice on her, and I personally think it looks hot on girls.

It was at that moment a thought popped into my head. “What would my nails look like with nail polish on?” I kind of shrugged it off because boys don’t normally wear nail polish, but curiosity got the best of me. It wouldn’t hurt just to see, right? The stuff can be taken off later, and I’ve got two weeks to myself.

Browsing through her collection, there was just so many. She had pinks, reds, blues, purples, you name it. I found a bright red that looked nice and decided on that. I started by taking off my socks to do my toenails. I shook the bottle like I’ve seen Jenny do many times, screwed off the brush, and got to work. Taking the leap into the unknown, I carefully applied the polish to my big toe. As the brush glided across the nail, I just felt a wave rush over me. It felt so good, so right. Once I finished that nail, I continued on and did the rest of my toes.

I observed my handiwork, and it looked amazing. The color was perfect, I didn’t think it would look this good. Every movement of my toes changed the reflection of light off of them, further reminding me of the polish’s presence. For some reason, the polish even made my feet look smaller, almost like a girl’s.

I then moved on to my fingernails. Pretty much the same process as my toes, just different nails. It was harder to paint with my non-dominant hand, but I was able to get the job done. After I finished, I took a look at what I had just done. Just like my toes, the polish looked really nice on my fingernails, and it made my hands seem smaller. The longer nails on my fingers made the nails look even more feminine than they already were. Looking at both my fingers and toes, I just couldn’t believe it. They were practically a woman’s feet and hands, but attached to me!

I soon noticed that my penis had become rock hard throughout the process. I knew what I had to. I checked to make sure my nails were dry and headed to my bedroom. I jumped onto my bed, and then I slid down my shorts and underwear to reveal my throbbing penis. I have masterbated plenty of times since hitting puberty, so this was nothing new to me.

I grabbed my penis with my newly painted nails and it was so hot. It was like getting a handjob from a woman, which I had yet to experience. I started slowly sliding my hand up and down my penis. It was so methodical seeing my feminine hand move that way, grasping my dick like it was taking on more than it could handle. The more I stroked, the harder my penis got, and it was soon standing attention like a flagpole. My eyes began to take notice to my polished toes and I couldn’t take it any longer. I exploded like I never had before, cum continuously squirting on my nails, stomach, and chest.

That was the most intense orgasm I had ever had. I had never experienced anything so mind-numbingly good. “This is definitely something I have to do more often,” I happily thought. I cleaned up after myself and went back to watching TV, nails and all. This was going to be a good couple of weeks.

Day 4

The first few days, I was doing what I normally did while the girls were gone. It was hard to keep my focus sometimes, though, I kept looking back at my nails. Just a glance at them made my dick spring to attention, almost every time. I masterbated so many times to relieve the pressure, but it barely did any good at keeping my penis soft.

This day, I again got bored and went back to Jenny’s room to see what else there was. I looked through some of her drawers and found pairs of panties. I hadn’t seen a pair up close before, I’ve only seen them on women in magazines and on the Internet. I grabbed a light blue pair in my hands, and they felt so soft. Why doesn’t my underwear feel this good? I was about to put them away when I paused. “These might be nice to wear,” I wondered, “but is this going too far? Nail polish is one thing, but panties are another level.” I thought about it, and I figured that I was getting to explore things I had never dreamed of, and when was there a better chance to do it?

I decided to go for it as I took off my shorts and underwear. I slowly stepped into the panties and slid them up my legs. The soft fabric felt so erotic touching my skin. This was like nothing that I had ever experienced before. Once the panties got into place, I noticed that they were a little tight due to my penis. I adjusted my member so that it was held in between my legs. It definitely feels better now.

Looking in my sister’s floor-length mirror, I was a little stunned. The panties looked so good on me. There was some noticeable hair on my legs, but I still looked very feminine below my stomach. The panties accentuated my butt and hips, giving my body some curves. I guess I never noticed the shape of my body since my boy clothes kind of hide it.

I decided to put my shorts back on as I went back to watching TV. Every time I moved, it reminded me that I had panties on. The softness of them was so comfortable, so much better than my normal underwear. The panties kept slipping in between my buttcheeks, and it made me feel so naughty. Once the day ended, I noticed that a little cum had dribbled from my penis onto the panties, and some of it went partially down my leg. I guess I had never realized it, I was too focused on everything else. I made a promise to myself that I would not wear boy underwear for the rest of my time alone, only panties.

Day 6

I went into Jenny’s room to change out “my” panties for the day. Before I did, though, I decided to take a look into Jenny’s bathroom. She had a big shower, definitely bigger than the one I’ve had to use. I looked at all of the products she had. There was the normal stuff, like body wash and shampoo, but with more feminine scents. There was one thing I didn’t recognize, though, and that was a bottle labelled “Nair”. On the bottle, it said that it was a depilatory to remove hair from your body, giving you silky smooth skin.

I’ve always kind of wondered what I would look like without hair on my body. Jenny always had hairless skin, I’ve only ever seen hair on the top of her head. It was a quick decision for me to slather the Nair all over my body. I waited the appropriate amount of time and jumped into Jenny’s shower. As the water came down, it washed all the cream off of me, my body hair going with it. My body felt so smooth, it was like silk, and it was erotic.

While I was in there, I cleaned myself up with Jenny’s body wash. Using her loofah, I washed every inch of my body. The flowery smell was very feminine, no wonder Jenny loves this stuff. I then used the shampoo to clean my somewhat-longer hair, giving it some shine and the same scent as the rest of my body.

Due to the scents and the whole experience, my penis was rock hard. I took my hand and started stroking, again loving how feminine my nails looked around my member. My other hand started feeling the rest of my body, and I got harder the more I touched my silky skin. It was an electrical feeling, stimulating the already sexy experience. My hand wandered up to my chest, and once my fingers grazed over my nipple, my body was jolted back. It felt like my nipple was connected my groin, with every little touch giving me an intense sensation. For a solid two minutes, I kept stroking my penis and tweaking my nipple. I was so desperate for release as the warm water from the shower ran down my back. I finally made one final tug on my nipple and it pushed me over the edge. My back arched and my body began to feel num. Cum erupted from my penis, every squirt flying through the air, with cum soon running down my smooth legs and onto my painted toes. I counted at least 20 individual squirts of cum as my dick got softer and softer. That orgasm was a lot more satisfying and much better than the one I had on the first day.

I made sure all the cum had washed off of me before stepping out of the shower. Jenny had a dressing gown hanging on her door, and I decided to wear that to dry me off while I picked out the panties I would use for today. I found a nice lacey red pair of panties that was a similar color to my nail polish. I slipped them on while still wearing the dressing gown. I loved the way it felt as the panties graced my now smooth legs.

I searched Jenny’s drawers to see if there was anything else to find. In one of the drawers, there was a bunch of bras. Curiosity took over and I decided to try one on. I found a bra that seemed to match the panties, and took off the dressing gown to expose my chest. I put my arms through the straps of the bra. I kind of struggled to connect the hooks in the back, but I was able to get it. Looking in the bra drawer, I saw a pair of something in the back. Picking them up, they felt like jelly, and some memories came back to me.

Jenny had worn these when she was younger. She was in a play before she had boobs, and they required her to have something on her chest to play the part. I had seen her get dressed for the play, so I knew what these were. They were fake breasts!

Since I had the bra on, I decided to see what I would look like with boobs. I inserted the breast forms into the cups of the bra, having to loosen the bra a little to make room for them. I cupped my hands around my new additions, feeling the weight that came with them. They were at least a B cup, maybe even more.

Looking in the mirror, I observed what I looked like. From the neck down, it was hard to tell that this was not a woman’s body. Like before, the panties made my waist and butt look very girly. The bra didn’t do much on its own, but the breast forms helped out there, making it seem as though I had real breasts. My body had no hair whatsoever, and I was probably just as smooth as Jenny normally was. If all of that didn’t make my body look feminine, my bright red nails made the difference.

I put my boy clothes over everything and decided to browse the Internet. I found that there are a lot of boys like me. I kind of thought I was weird for doing all of this, but knowing that I’m not alone made me feel a lot better. I wondered what else I could do to make my experience better…

Day 9

After doing a lot of research, I decided that I would fully embrace my femininity. Today I was going to see what it was like to fully become a girl. I was a little nervous, but I just had to explore my feminine side.

I started out by taking another shower. My body was still smooth from using the Nair the other day, I guess my hair just grows very slowly. I washed myself with the body wash and shampoo, and I really loved the flowery scent that they left on my body. After the shower, I got into the dressing gown again and got to work.

I started by working on my hair. My blonde-ish hair went down to my shoulders, so I had a lot to work with. I took Jenny’s brush and I parted my hair down the middle. I kept brushing my hair until it was completely straight. For the first time, I noticed that my hair looked very luxurious. The shampoo was really making it look nicer. I put some of Jenny’s curlers at the bottom portion of my hair, something I had seen Jenny do a few times. While that dried, I moved on to other things.

I was a little tired of my current nail color, the red got boring after a while. I took off all of the polish, and seeing myself with bare nails felt odd. I looked through Jenny’s collection and found a hot pink that I found to be very sexy. Once all of my nails, fingers and toes, were painted, I smiled as I loved the color.

Next, I decided to do my makeup for the first time. The past couple of days, I had watched a bunch of tutorials, so I was confident in my abilities. I started off with some foundation, which I spread evenly across my face. My sister and I have the same skin tone, so her’s works perfectly. Next, I took some eyeliner and carefully applied it, luckily not hurting my eyes in the process. I then took some mascara and used it on both sets of eyelashes. I looked through Jenny’s eye shadow, and found a blue and a pink that I thought would work well together. I first applied the blue, then blended in the pink to create a gradient effect on my eyes. Finally, I had some pink lipstick, which matched my nails. I took the lipstick and first colored in my lips, then I added a little more around them to make my lips look fuller and more feminine.

Once my hair dried, I took out the curlers. The curls of my hair looked so feminine, and every time I moved my head, they bounced. There was no doubt I had a feminine hairstyle now.

It was time to get dressed. I took off the dressing gown and my penis was standing attention. “I’ll have to do something about that,” I thought. I looked for a matching set of panties and bra to wear, and I found a pink set that looked nice. As I observed the panties, I noticed that there was a small opening in the back, placed right in the middle of my buttcheeks. “I wonder what this is for,” I thought, but I dismissed it, thinking it was some girl thing I don’t know about.

I slid the panties up my legs, getting the same electric feeling I have before. But before I completely got the panties up, I needed to do something about my penis. I had read about tucking online, and I knew that it would help me look the part. Using my pretty fingers, I shoved my balls inside me and used some tape to keep my penis in place. Only then could I fully put on the panties, since now I had a flat front. I took the matching bra, clasped it around my chest, and inserted the breast forms.

I search more of Jenny’s drawers and found what I now know is pantyhose. They felt really soft in my hands, even more soft than the panties. As I rolled the pantyhose up my legs, I felt a similar electric feeling as I did with the panties, but it was so much better, almost orgasmic.

I then moved on to Jenny’s closet to look for the clothes. This was the first time I had been in her big walk-in closet, and I was overwhelmed with how much she had in there. There were dresses, skirts, blouses, shoes, and so much more.

I found a short black skirt that looked nice, so I took it off of the hanger and slipped it on. It was so short that you could see my panties! I looked for a shirt to wear and saw a pink tank top that I’ve seen Jenny wear many times. I carefully slid it over my head as I didn’t want to mess up my makeup. I noticed that the tank top only went above my belly button. I finished the look off with a pair of tan wedges with 2-inch heels. It took a little bit to get used to walking in the heels, but I eventually got the hang of it.

I glanced at myself in Jenny’s mirror and I gasped. I didn’t see my reflection, I only saw a beautiful girl. The girl’s hair was long and elegant, with curls layered down towards her neck. Her makeup was perfect, her eyes standing out with the eye shadow and mascara, while her lips were in a feminine shape and color. Her boobs were very perky, almost popping out of her tank top. She had her luxurious legs encased in nylon, with her heels highlighting that her calves are to die for. Her nails, both fingers and toes, were perfectly painted and matched the rest of her outfit. She was my dream girl.

My penis was trying to break free from its prison as I got hornier and hornier. Oh my god, I was getting turned on by myself! I just couldn’t believe that I was the one in the mirror, and my penis obviously couldn’t tell, either.

I decided to take some pictures of myself. I took my phone and propped it on the floor next to the mirror, having it face Jenny’s bedroom door. I set it so that it would take a picture every few seconds and just let loose. I tried a variety of different poses, mostly ones where I’m laying on the floor. I took most of my clothes off for a few minutes to get sexy poses of me in just a bra and panties.

In one of Jenny’s drawers, I found a nice babydoll that matched my panties and decided to put it on. It had a bra built into it, so I didn’t have to worry about the breast forms falling out.

I posed for a few more pictures before a dirty thought came into my mind. I pulled down my panties a little and undid the tape that was holding my penis in place. I made sure that my member was in full view of the camera and started posing. I took positions of me doing a handjob, a footjob, and even going doggy-style, all with my enlarged penis being the main character. I could only imagine what these pictures looked like, a sexy woman playing with her penis.

Once finished with the pictures, I decided to take a video. I showed off my sexy legs, slowly running my painted nails across my smooth skin to meet similarly-painted toes. I squeezed my fake breasts, and even though I couldn’t feel anything, I arched my back to make it seem as though they were real and sensitive.

I took my penis in my hand and began to stroke it. I kept pumping and pumping for at least 10 minutes waiting for release, but it just wasn’t coming. Looking in the mirror, I could only see a sexy slut, one that was desperate to orgasm, and one that I wanted to fuck so badly. As I licked my lips, the woman in the mirror did the same, and all I could think about was those pretty pink lips sucking my cock, her tongue swirling around my member. It was at that moment I exploded with excitement. Cum flew everywhere, with the mirror, my legs, the babydoll, and even my face getting hit with the warm liquid. I was cumming for at least a minute before it finally stopped. I was shaking for a few minutes afterward, man that was amazing!

I licked a little bit of the cum off of my face as my sexy reflection did the same. It was so hot to look at, but honestly, I wasn’t a big fan of the taste of semen. Maybe it’s an acquired taste? I cleaned off everything of my sister’s that got hit with cum and wondered what I would do next.

I looked at the time, and it was only 12:00. I put my original outfit back on, retucked myself, and decided to grab something to eat. As I drank my water, it left a pretty pink stain on the glass, reminding me that I had lipstick on. I cleaned off my plate and noticed it was nice out. We had a pool, and I thought it would be fun to go for a swim. Our house had a tall wooden fence around it, so I could stay dressed en femme.

I looked through Jenny’s stuff to find some swimming wear. I found a pink two-piece bikini with a thong bottom and put it on. I also found a pair of feminine sunglasses that I might use. From her closet, I took out a set of Jenny’s sandals, which looked sexy on my feet. I grabbed a towel and headed outside.

I set all of my stuff down and jumped into the pool, making sure my hair stayed above the water as not to ruin it. Being in the water was definitely refreshing after the little session I had earlier. Swimming was a little harder to do with breasts, but I soon got used to it. Every kick of my legs made the thong bottoms slide in between my butt cheeks, and I felt giddy every time it happened.

After swimming for about half an hour, I got out, dried off, and relaxed on one of our lounge chairs. I put the sunglasses on as the sun was right in my eyes. I decided to tan myself a little bit, wondering how I would look with bikini tan lines. I flipped over after a while to get my backside, and soon after that I decided to head inside. While changing out of the swim clothes, I looked at my skin, and it was very obvious that I’d had a bikini on, especially around my chest.

I redid my makeup a little, since the pool messed it up. For the rest of the day, I tried on a lot of Jenny’s clothes, taking pictures along the way. She had a bunch of dresses, ranging from long and modest to short and skimpy. I even tried on her light blue prom dress, along with silver heels, and I just couldn’t get over the fact how hot and pretty I looked.

Her shoe collection was amazing, there was so much variety. I started out small, trying on flats, sandals, and flip-flops. Then, I began to wear every pair of shoes one by one, going from minimal heel all the way to seven inches tall. With every increase in heel size, I practiced walking in the shoes for a while, and soon heels became no problem for me.

Time must have flew by for me because it was no sooner time for dinner. After kicking off the shoes I was wearing, I put on some of Jenny’s yoga pants and a sports bra, then headed to the kitchen for a light meal. After eating, I looked up a few yoga videos and exercised for over an hour, similar to what Jenny did every night. I then relaxed on the couch and watched some TV.

A couple hours passed and I was feeling really tired, it was such a long but enjoyable day. I went to Jenny’s room, changed out of my clothes, and put on the same babydoll that I wore during my masturbation session. I decided to sleep in her room because why not? Her satin sheets, along with the babydoll, rubbed against my smooth skin, and it was so erotic. I think I was leaking a large amount cum in my panties, as I noticed a wet spot on them. My dick was soft the whole time, even after I had untucked myself earlier, and I didn’t even know that much cum could come out without being hard. I’ve heard that women get wet without any stimulation down there, I guess this is something similar? I then fell asleep, knowing that this was a perfect end to the best day ever.

Day 13

For the last days of Mom and Jenny’s trip, I had lived as woman, and it was an incredible experience. Now, though, I had to go back to boy mode, as they were coming home the next day.

I first changed into my regular clothes, which kind of felt weird, a little uncomfortable I might add. I looked at my face and did the work to make sure I got every last trace of makeup off. I took the nail polish off of my fingernails, and was going to do my toes, but I figured that I could keep them a secret. I brushed my hair back to its original style, getting rid of my curls. My body hair was starting to grow back; I didn’t have much to begin with, so I figured that a couple more days would bring it back to normal. I noticed my tan had almost gone away, but it could still be seen a little, so until it was completely gone, I could hide it. Finally, I cleaned all of Jenny’s clothes that I had worn, along with making sure her room was exactly how she had left it. I also ended up downloading an app on my phone that requires a passcode to see specific photos and videos, and transferred everything I took over the course of these past two weeks into it.

For the rest of the time I had, I just watched some TV, but it made me reflect on what I had done. Did this mean I was gay? “I don’t think so, I’m definitely still attracted to women, and the thought of having sex with a man sounds gross,” I thought. What about being transgender? Do I fully want to be a woman? “While that might be fun temporarily, I love my penis, and I don’t think I would want a vagina to replace what I have already.”

What does this mean for me, then? I guess I could be described as a crossdresser, but it wasn’t necessarily about looking like a woman: it was the sexual thrill that I felt when being like one. I don’t think there’s a great term to represent my situation, but I don’t really care. All that matters is that it was fun and there was no harm done.

I kicked me feet up onto the coffee table to see my pretty pink toes. I’m kind of sad I have to hide these, but I’ll still get to see them at least once a day. And I have my pictures to look at, so it’s not like this experience is just running around in my brain.

Day 14

Mom and Jenny got out of the cab and we greeted each other with hugs. I helped them unload their stuff and bring everything inside. I asked how their trip was, and they said it was fun. They asked what I did the past two weeks, and of course I lied and said just video games and TV. Mom joked and said that college was going to bite me in the butt come next month.

We ate dinner as they talked about what they did on their trip. They went to beaches, hit up bars, and did a lot of relaxing. I couldn’t help but think what it would be like to go on the trip with them. I guess I would have to be a girl for two weeks, but it’s not like that would be much different than what transpired at the house.

We sat on the couch and watched a few movies together before calling it a night. I almost went to Jenny’s room on instinct, but I stopped myself and made sure that didn’t happen. I entered my room, changed my clothes, and got into bed. As I fell asleep, I was a little disappointed that it would be a while before I could dress up again. But I was still excited for what would happen, and I couldn’t wait for next year.

Last summer was the best experience I had ever had, but it had to end some time. Mom and Jenny surprisingly didn’t catch on to anything that had happened, at least nothing that they mentioned to me. I had decided to go to a college that was close to home, but I wanted to live in the dorms as it was more convenient for me. It was definitely hard being fully on my own, but I was able to get through it.

During my first semester, I met my girlfriend Anna in a class that we shared. We bonded over our love for technology (both of us are Computer Science majors), and we began to date after a couple of months. I lost my virginity to her, and we have had sex a bunch of times since then. We love each other very much.

A couple months prior to the summer, I confessed my secret of crossdressing to her. She was really supportive, and she was actually excited more than anything. She’s bisexual, so maybe that had something to do with it? Either way, I’m really lucky to be with her.

As summer drew closer, Anna talked more and more about how she wanted to see me dressed as a woman. We decided that, once my mom and sister leave for their trip, we would start the process. She wanted to see the transformation happen before her eyes, so I wasn’t to do anything before she got there. While Anna was from out of town, she used the excuse of taking a short summer class to stay on campus, so she was going to be here for most of the summer.

This year, Mom and Jenny decided to go on a longer trip than normal. Jenny had just graduated, so she wanted to have one last hoorah before starting her new job. Mom had some extra vacation time built up, and she figured that this was the best time to use it. They decided on a whole month-long trip! That meant that I had twice as long to enjoy myself and have fun with Anna.

Day 1

Like last time, I helped take the suitcases to the taxi that was in front of our house. Mom and Jenny had a lot more packed this time, so it felt like there were bricks in their luggage. Mom gave me a longer hug than normal, saying she was really going to miss not seeing me for a while. She was a little worried that I would be bored out of my mind and couldn’t handle being alone for that long. I reassured her that I’ve done it before, and that Anna was around to keep me company. “She’ll be doing much more than that,” I thought. We gave our final goodbyes as they got into the cab, and it drove off.

Once the cab turned the corner, that’s when I texted Anna that it was time. “I’ll be there in about 30 minutes,” she texted back. The anticipation was killing me, I didn’t think I could wait that long. But soon, her car pulled up into the driveway. As she got out, I couldn’t help but stare at her. She was so gorgeous with her beautiful legs, sexy clothes, and perfect makeup. I still couldn’t believe I was dating her.

“Are you going to keep looking me over, or are we going to get to work?” she said, snapping me out of my trance. “Sorry, you just look so pretty,” I said. “Aww,” she blushed, giving me a peck on my lips. “Now, come on, I want to see you look pretty, too.” We walked back into the house and closed the door behind us.

We figured that the best way to start off was for me to take a shower. I stripped down and headed for the bathroom. “I’ll pick your clothes out while you’re in there. I guess your sister’s clothes are going to have to do for now until we get your own clothes,” Anna remarked. “My own clothes?” I questioned, but that was soon out of my mind as I got into the shower.

I took the bottle of Nair again and made sure that every inch of my body was covered with the cream. After a little while, I turned on the shower so everything would wash off of me. I touched my skin and it was back to being smooth. I was already getting hard from the erotic sensations, I’ve missed this so much. I cleaned the rest of myself with the feminine soap and shampoo and stepped out of the shower. I looked around the bathroom to see if there was anything that might make Anna happier, and I found a bottle of lotion. I used some of it on my skin and it made me even softer than before! I put on the dressing gown and left the bathroom.

On Jenny’s bed, Anna had just finished laying out the clothes for me to wear. There was a pair of pink panties with a matching bra (different than the set from last time), along with the breast forms. She had also put out a pair of short shorts with a light pink crop top.

Anna turned around and saw me for the first time with hairless skin. She smiled and said, “you look so sexy, especially with that dressing gown.” As I took off the gown, she could see that even the hair around my genitals was gone. “Mmm, I think I like you much better this way. But if we’re going to go all out, we have to something about your penis.” It was rock hard at that point, and tucking would be too difficult with it this way. Anna apparently knew what to do now.

She got on her knees and started playing with my penis. First, she stroked at a slow pace, but increased her speed gradually. Since I was already turned on, it didn’t take long for me to be at peak hardness. I was about ready to cum when she stopped. She waited almost a whole minute before taking my member in her mouth. She bobbed her head back and forth, with me loving the way her lips felt grazing my penis. She used her tongue to continuously heighten the sensations I was feeling, and soon I just couldn’t take it anymore. I cummed in her mouth like there was no tomorrow. She began to suck in order to get every drop of cum that was coming out of me, and my penis kept shrinking until it was just a little nub. That was the first blowjob I’d ever had, and it was amazing. Anna swallowed my cum and smiled. “Now you’ve got your own little clitty.”

Anna helped me tuck my now soft penis and had me slip on the panties. She picked up the breast forms, salthered some glue on them, and stuck them to my chest. She then took the bra and put it on me, easily hooking it behind me. I finished everything off by putting on the shorts and top. Seeing myself in the mirror, I smiled, knowing that this was just the beginning.

Once Anna had fully looked me over, she said, “Damn, you’ve got one hot body. Especially that cute little butt.” She then slapped me on my ass, and I think I blushed a little.

Before we started on hair and makeup, she got her suitcase out and opened it up. She then took out her own set of makeup, saying that it was probably better not to use my sister’s. She also took out a hair dryer, a curling iron, and some scissors.

Anna took the scissors and cut just a little bit off the bottom part of my hair. She used the hair dryer on my hair while she brushed it out a little. Once my hair was dry, she took the curling iron and used it to add a little style to my hair.

She announced that my hair was finished and we started on makeup. She gave me the foundation, mascara, eye shadow, and lipgloss, wanting to see me do it myself. Just like last summer, I took the foundation and applied it evenly to my face. I looked to the eye shadow, and the one Anna had for me was blue and glittery. I closed my eyes one at a time and applied the shadow to my eyelids. I then took the mascara and carefully used it on my eyelashes. Finally, I twisted off the wand of the lipgloss and covered my lips with the red color. I looked at myself, and I was breathtaking.

I then turned around for Anna to see my work, and she was shocked. “Baby, you look so sexy. I’m surprised you did that good of a job. I don’t think I can call you Leo anymore, you need a feminine name.” I thought about it for a little bit and said, “what about Lauren?” “Oh my god, that’s perfect!”

At this point, it was about 4:00 in the afternoon. “What should we do next?” I asked. “Let’s do a slumber party!” she practically blurted out, which is probably what she had planned from the start. So, with that, we moved to the living room.

First, we painted each other’s nails. She started off with painting my toenails in a bright pink color. She took some nail extensions out of her bag and glued them onto my fingertips. She filed them down into an oval shape before painting them with the same pink as my toes. Once my nails had dried, I did the same thing to Anna’s nails. Everything had become harder to do with my longer nails, but I honestly couldn’t complain. Soon enough, we had matching nails.

We felt a little hungry and decided to order a pizza. While we waited, we played truth or dare. I started off and said truth.

“How sexy do you feel right now?” Anna asked.

“Very sexy, a lot more than the last time I dressed up actually.”

Anna also chose truth. “I guess I’ve never asked you this, but when did you find out you were bisexual?”

“I was a little tipsy at a party in high school, and I made out with one of my friends. We then went into one of the bedrooms and did it, and it was the best sex I had ever had.”

“That sounds so hot.”

I then chose dare. “I want you to answer the door to the pizza guy once he gets here.”

“What? I don’t think I can do that.”

“Come on, you look completely like a girl, no one will think you are a boy. All you have to work on is your voice.”

I agreed, and she coached me on how to make me sound more feminine. I eventually got the hang of it. Once she proclaimed that I was ready, the doorbell rang. I hastily got up and answered the door. There was a teenage boy standing there with the pizza in his hands. He kind of stared at me a little before getting out, “Uh, cheese pizza, $7.50.” I hand him the cash and said, “here you go, and keep the change” in my new girly voice. I took the pizza, thanked him, and closed the door.

“Oh my god, Lauren, he was practically drooling over you!”

“If only he knew what I had tucked between my legs,” I said, and we both giggled.

As we ate our pizza, we talked about what the rest of the night looked like. Anna had the idea of watching a movie, but she wasn’t sure which one. I agreed with that idea. I took our plates and cleaned them in the sink.

Anna had gone to her suitcase and grabbed two matching pink babydolls, figuring that we should get comfortable. We both changed into them and snuggled on the couch. We found a chick flick and began to play the movie.

We only got about halfway through the movie before we were making out. The feeling of our lips touching, both of us with lipgloss on, was newly found sensation, and I was loving every minute of it. Once the movie ended, Anna suggested that we move to the bedroom.

I was about to take everything off before Anna stopped me. “I want us to have sex like women, no dick is needed.” I shrugged and we went back to making out, practically jumping onto my bed. I began to rub my pretty nails all over her body. I pinched her nipples, and she let out a moan. I then peaked my head under her babydoll to work on her nipples more. But now, I decided to use my mouth. I started to suck on her nipple and she moaned even louder this time. I swirled my tongue around and kept sucking, her moans being almost melodic. Then she let out a huge scream, and she cummed in her panties.

Knowing her, I knew she wasn’t done yet, so I moved my head down towards her vagina. I pulled down her panties, seeing how wet they had become. Keeping my hands up near her breasts, I began to eat her out. I played with her nipples while my mouth explored her opening. She was moaning even more than earlier. “Oooh, Lauren, I think I’m about to cum again!” Just as she said that, I could feel her spasming as her legs tightened around my body. One last twist of her nipples made cum fly out of her. After multiple spasms, my face was covered. I licked every last drop out of her vagina and went back up to kiss her so she could get a taste of her own juices. We then collapsed on the bed.

“That was amazing. I’m going have to return the favor to you sometime,” Anna exclaimed, still catching her breath.

This was going to be one hell of a month.

Day 4

“Hey Lauren, I think we need to go out and get you your own clothes.”

I wasn’t surprised that she brought this up again. I definitely didn’t want to keep wearing Jenny and Anna’s clothes, but I just didn’t think I could go out like this. I mentioned my concerns to Anna.

“I know this might be going a little fast, but I think you’re ready. You look nothing like a boy, and you’ve mastered your feminine voice. Worst case scenario, you will be seen a woman who’s just a little shy.”

She was right about that, and after a little more begging, I gave in. Soon, we left for the mall, and once we got there, I just felt butterflies in my stomach. This is such a big step, but I felt confident enough to step out of the car and walk inside with Anna. The mall was busy enough that day, so luckily nobody was paying attention to us. First, we went in Victoria’s Secret.

“You should pick out at least 5 matching sets, but there is probably more to get,” Anna told me.

“How much is all of this going to cost?”

“Don’t worry about it. My parents gave me a credit card to buy whatever I want.” I forgot her parents are rich, they own some big company on the east coast.

Since we knew my size, I didn’t have to try anything on (definitely glad about that). Once we were done in there, we had such a variety of items. There was panties (bikini, boyshorts, and thongs), bras (regular and sports), sheer pantyhose, and nightwear (babydolls and a nightgown), all in a range of reds, blues, and pinks.

We then moved on to one of the clothing stores. Anna didn’t say what I should get here, but she definitely veered me towards the more girly items. We soon had skirts, short shorts, frilly tops, and even a couple of dresses. This time, though, she wanted me to try on everything. We both went into one of the dressing rooms and I modeled everything for her. I actually was having fun, all of the nerves were gone at this point.

I got my original clothes back on and Anna said she was a little turned on from seeing me try on the clothes. We opted for a quickie as I pulled down her panties and fucked her with my pretty nails. We had both become extermely turned on from doing it in public, and she cummed twice, while I cummed once. We made sure our hair and makeup was still okay, stepped out of the dressing room, and paid for the clothes.

The shoe store was next, where I tried on too many shoes to count, all in varying heel sizes. We decided that I only needed a pair of sandals, some pumps, and a couple of high-heeled open-toed shoes.

The last store we went into was the beauty store. Anna said that I should choose my own makeup, she didn’t want to make an decisions for me here. I looked around a little and found two shades of lipgloss (red and pink), an eyeshadow palette, and some nice black mascara. Then I went to find some nail polish, which is my favorite thing to wear. I found a bright red, a baby blue, a light pink, a white, and base/top coats. I said that I was finished and we payed.

Before we left the mall, Anna mentioned she wanted to do some shopping on her own, but she wouldn’t be long. I said that was fine, and I would grab us some lunch. I bought a couple of light sandwiches from the food court and found a booth to sit at. After about 10 minutes, Anna came back from her shopping and we started eating.

“How did you feel about today?” she asked.

“It was good. I felt uncomfortable at first because I thought people would catch on to me being a guy. But after a while, I realized that nobody seemed to notice, or they just didn’t even care if they did notice.”

“I told you that you look like a woman, so I’m not surprised there weren’t any issues. But I think what also helped was the way you are moving now.”

“What do you mean?”

“Well, I think this might just be your heels, but you have started to sway your hips while you’re walking. And you have become more delicate when picking up things, probably because of your new nails.”

I guess I never realized it, but she was right. All of the things I was wearing forced me to change my movements, and I’ve been doing it enough for it to become second nature.

We finished up our meals and left the mall. I didn’t ask Anna what she had bought on her own, but she mentioned that it was a little surprise for me later in the week. I obviously didn’t know what that was, but I would soon find out that it was more than I would have ever expected.

I left off the story with me exploring my femininity with my girlfriend, Anna. We had gone to the mall, and Anna had bought a little something special for me…

Day 7

As I woke up, I noticed that Anna was lying awake in my arms. I kissed her and told her good morning, and she did the same. The combination of her closeness and the feeling of my new nightgown was exhilarating. This was definitely the life.

Anna was unfortunately leaving for a week. She was going back to her hometown to visit her family. I really wish she didn’t have to go, but I know how important family is to her.

Before we got up, Anna said that she wanted to give me a little treat for all of the effort I’ve put into becoming a woman. I got very excited as she pulled down my panties. She released my dick from its prison and it sprung to attention. She had me lay down on my back and she got to work.

She started by giving me a handjob. As she rubbed her hands along my member, her long nails would click and sometimes touch my skin. Her pretty nails could have made me cum on their own, but she kept the pace slow so that I didn’t explode too soon. She then took her hands off of me and lowered herself onto my penis. She moved little by little before I was fully inside her. I could feel her wetness with my penis, and it acted as a lubricant for our intimate love-making session. I was getting ready to cum, but she lifted herself off of my member before that could happen. She waited a little bit before she spoke.

“Before I let you cum, you’ve got to beg me for it like the girl you are.”

I was a little confused at first, but I understood. “I wanna cum sooooo bad.”

“I don’t know if that’s girly enough. I want to hear you talk about being a sissy and having your clitty sucked.”

“Please let me cum, my clitty is desperate to be sucked. I’m such a little sissy and need to have some release.”

“That’s better. Now keep saying it while I suck you.”

As she sucked on my dick, I cried out that I was such a sissy for having my clitty played with. I talked about how much of a girl I was and I was such a slut for wanting sex so much. Soon enough, my penis spasmed, and I began to cum in Anna’s mouth. Every little squirt was a wave of pleasure. She used her tongue to make sure that she could make me cum as much as possible. My dick became very small and was the same size as after the last blowjob. Anna, with cum still in her mouth, move up to kiss me. She released all my semen into my mouth and had me swallow. I still wasn’t a big fan of the taste, but in that moment, I did feel like a sissy slut.

Anna got up and grabbed something out of the shopping bag she had from our trip to the mall. Before I even knew what was happening, she took my dick and attached something to it. When I looked down, I saw a pink piece of plastic in place of my penis.

“This is called a chastity cage. It prevents you from getting hard or even touching yourself. I’ve got to make sure you stay a good girl while I’m gone. I’ll have the key with me, so there’s no way you’ll be able to get it off.”

I was a little stunned. Where the hell did this idea come from? I had to admit, it was more comfortable than the tucking, but still. I guess I was under her control at this point, and I just had to live with it.

We spent some of the morning hanging out before Anna had to get to the airport. I decided to drive her there in her car, since I didn’t want her to have to pay for a taxi or parking. Once we got there, we kissed each other goodbye. Before she went in, she mentioned something to me.

“I know you’re kind of disappointed about the little cage you have now, especially since you can’t masterbate like you normally do. But I couldn’t let you suffer, so if you get desperate for some release, I left a few surprises in my bag to help you do that. Bye, baby, I’ll miss you.” With that, she walked through the doors of the airport.

“More surprises,” I thought. “That’s just great. And how can I get release without having Anna and with my penis locked up?” I wondered what I had gotten myself into the whole time I was driving home.

Day 12

The first couple of days without Anna weren’t too bad. My nails had chipped a little, so I repainted them, with a French manicure on my fingers and red on my toes. I also kept practicing doing my makeup, even though I was already good at it. I tried on the clothes we bought last week again, making sure that I still liked them.

After a while, though, things got harder. With all of the feminine activities I was doing, I was getting horny. My penis would constantly try to get hard, so it kept straining against its cage with no luck, making me a little uncomfortable. At this point, I was feeling so hot and bothered that I couldn’t take it any longer.

I went to Anna’s bag to find what her surprises were. There was a bunch of things in the bag, but one of them had a note attached to it. It read:

Lauren,

I knew you would cave at some point, you little sissy slut. Since your penis is useless right now, you need a new way to get pleasure. This bag has many things for you to use, but I want you to start out with the toy this note is taped to. Use it on your virgin pussy, preferably while you’re on your back. There’s some lube in the bag, and I recommend using plenty of it. Have fun!

I looked at the toy and my eyes widened. It was a dildo! “I can’t use this, this is way too far!” I said aloud. But I started to wonder if it wasn’t. I was already completely like a girl in every way. During the past week, the way I looked, moved, and even had sex was in no way like a guy. Does that mean I should try to masterbate like a girl, too? I’ve been curious about what it’s like, and obviously Anna thought that I should try it out.

I was so horny that any worries were out the window. I took the dildo and examined it more. It was about 6 inches long and 1 inch wide. Could this thing really fit inside of me? I guess there is only one way to find out.

I stripped down to just my bra, grabbed the dildo and lube, and layed on my bed. I propped my legs up, with my asshole in full view, and got to work. I squirted some lube into my hand and rubbed it all over the dildo. I also used a little bit around the inside of my opening. I took the dildo and slid it in between my buttcheeks. As it entered my hole, I gasped. It was such a weird and wonderful sensation.

It didn’t take long for the dildo to be completely inside me. I slowly started moving it in and out, trying to mimic how I’ve fucked Anna before. I started to moan, it was almost involuntary. I soon found a spot that made me feel amazing and pumped the dildo so that it would consistently hit that spot. My moans were in line with the movements of the dildo. I kept at this pace for about 30 minutes before my body began to feel tingly. I rode this tingling sensation as it increased, and soon, my entire body was floating on a cloud. After a few more fucks of my opening, I felt a huge wave of pleasure rush over me, and I tensed up as I exploded with enjoyment. It felt almost like an orgasm, but different, and a lot more satisfying.

Laying on my bed, I still felt unbelievable. That was the best orgasm I had ever had, there was no doubt in my mind. Looking at my clitty, I noticed only a few drops of cum came out of me. All that pleasure, and I only cummed a little?

I realized that I still felt horny and decided to go at it again. Over the next hour, that dildo stayed inside me as I wanted to keep fucking myself. I orgasmed three more times over that time period. After the final one, I just collapsed on the bed. The dildo slid out of me on its own, making a distinct popping sound. I definitely had to do this again.

As I was getting up, I decided to see what else was in Anna’s bag. There were multiple dildos of various shapes and sizes, and one even vibrated. She also had an array of butt plugs in different sizes. I decided to see what they felt like and picked up the smallest one. I took a little more lube and squeezed the plug into my opening. “Ooh, that feels nice,” I thought.

I put my clothes back on and just chilled out for the rest of the day. I couldn’t help but tighten my sphincter every now and then, reminding me that the plug was still there. I loved having something inside of me. Anna was definitely right about me being a sissy.

Day 14

I drove to the airport to pick Anna up after her trip. As soon as she walked out, I got out of the car and greeted her. We made out for a little bit before I helped put her suitcase into the back of the car. People were probably a little weirded out seeing a “lesbian” couple kissing each other for so long, but I honestly didn’t care. We got into the car and drove off.

“Did you use any of the surprises I left for you?” Anna asked.

“I did. Actually, I’m using one of the butt plugs right now.”

“Mmm, I can’t wait to get back and see you with it. What about the dildo?”

“All I’ll say is my pussy isn’t a virgin anymore. I fucked myself silly the other day.”

“Oh my god, Lauren, that’s so damn hot. I think I need to fuck you later. I haven’t had any release all week, it was a little hard to do anything with my parents in the next room.”

Once we got to the house, we practically jumped out the car with excitement. After I closed the front door, we began to make out again. We took off each other’s clothes, leaving us in our sexy lingerie as we moved to the bedroom. “I wanna take a look at your pussy,” Anna exclaimed. “I need to know what I’m in for.”

I complied and took off my panties. I layed face down on the bed with my ass in the air. Anna smiled when she saw the butt plug, taking it in her hands and yanking it out. A little squeak came out of me when she did that.

“Before we get to it, I need you to do something. I can’t work with an unclean pussy, it’s unsanitary.” She grabbed something new out of the bag and gave it to me. “I want you to give yourself an enema. Make sure that the liquid that comes out of you is clear before you return to me.” I did as she said and came out with a nice, clean opening. “Now we’re ready.”

Anna had me get on all fours while she prepared herself. She played with my buttcheeks a little before spreading them out. She took some lube, spread it on her fingers, and got to work. She started by teasing the rim of my pussy before inserting one finger. She rhythmically moved her finger in and out of me before adding a second finger. I moaned with pleasure as she finger-fucked me as hard as she could. Once she added a third finger, I was in heaven. That small amount of effort made me orgasm in no time.

Obviously, we were still horny, so we weren’t done yet. Anna turned me on my back and moved her head towards my pussy. She was about to eat me out! She stuck her tongue out and got to work. It started out with just a light licking, but soon her tongue became its own fucking machine. Her tongue explored my pussy, and it consistently hit the sweet spot. I moaned even more than last time as she continued to devour me. This was amazing! I let out one last squeal before I orgasmed again.

“You up for more?”

“I’m still so fucking horny, of course I am!”

Anna got one of the dildos and used an attachment to strap it onto her. Looking at the dildo, it was about 8 inches long and 1 1/2 inches wide. God, that’s so big! “Now, this dildo is a little special, and you’re going to see why in a little bit.”

Staying on my back, I lifted my legs up onto Anna’s shoulders so she could have full access. She took a generous amount of lube and put it on the dildo and my pussy. When she entered me, I let out a little moan. It felt so good having my pussy stretched! She started with a slow pace and was only a couple inches deep. As time went on, she increased the speed a little, progressively getting the dildo further inside of me. Before I knew it, the whole thing was inside me.

I could feel an orgasm start to build up, but knew that it would still be a little while before it happened. I wanted this to be the best orgasm possible, so I said, “Fuck me harder! I want to feel everything!” Anna complied and quickened up the pace. I moaned with pleasure, and my moans began to sound more girly the more she fucked me.

We kept at this for about 10 minutes before I felt like I was going to orgasm again. “Oh god, I think I’m about to cum!” Right before the release, I felt the dildo jerk a little and something warm and sticky shot into my pussy. Whatever it was, it sent me over the edge. This time, as I orgasmed, a huge squirt of cum came out of me and hit Anna in the face. I was a little surprised by that, since I’ve only ever had a few little drops come out of me while locked up. We both collapsed on the bed, with the dildo still inside of me.

“I see you liked the little surprise this dildo had in store,” Anna said. “If you haven’t figured it out, it simulates the male orgasm and shoots out its own version of cum. So, you just got fucked in the most girly way possible.”

I was still catching my breath from that amazing experience. I honestly didn’t care that I practically had a penis cum inside of me. This newfound form of orgasm was life-changing, and I don’t think I ever wanted to go back to having a male orgasm.

Anna and I snuggled together in bed. I wondered what the rest of the month would be like as we fell asleep in each other’s embrace.

To be continued…