This is the story of two college guys that are challenged to slowly add female aspects to their lives by their girlfriends. The gradual changes end up taking them much further than either of them ever expected.

THE CHALLENGE by Nina Adams

IN THE BEGINNING
I do not know where to begin my story. I am sitting here in front of my sister’s vanity mirror looking at myself and cannot believe that the image is actually me. Today, I am going to be Maid of Honor at my sister Sasha's wedding. That would not be so unusual, if it were not for the fact that I was born a boy. In fact, a year ago, I was living the life of a typical college sophomore at the University of Illinois. So much has happened this past year that I don't even know where to begin.

I think it is best to start in high school when all of my friends referred to me by the name of Michael. I was a fairly athletic student with typical male hobbies and activities. I played on the school tennis team and soccer team. Both of these activities kept me in very good shape. I had a girlfriend from the neighborhood named Jana and we were about as close as any boy and girl could be. We had known each other since we were about seven and in the last couple of years had taken our relationship to the next level. We were both good students, and our parents loved the fact that we were going out together.

My mother was divorced and we lived in a big house in Highland Park. She was divorced from my father when I was about five years old. She caught him cheating and kicked him out of the house. Mom came from money and did not have to worry very much about finances when my father and her got divorced. Having only one parent in the house, I was very close with my mother. I rarely kept a secret from her and probably talk to her more than most boys talked with their mothers. She was very protective of me and always wanted the best for me. I always had nice clothes and pretty much anything else I really needed. I wasn’t spoiled, but we lived a pretty good life.

As I mentioned, I have one sister, Sasha. She is two years older than me and was always one of the most popular girls at school and in the neighborhood. We were pretty close too, but because she was older and a girl we did not do a lot of things together. I think I always envied how popular she was, but it wasn’t like I didn’t have any friends. Jana and I were very close with Rita and her boyfriend Nick. The four of us, always hung around together and became quite a foursome. As it would turn out, we all ended up going to the University of Illinois together. Getting into the University was not easy, but since all of us got in, I think the bonds between us became even stronger.

I did not have any tendencies towards girl things other than in the normal way. Or at least I don’t think I did. I can only think of a few, pre-college day dressing activities that really stood out. I remember when I was about seven or eight being a cowgirl for Halloween. I had wanted to be a cowboy, but the only costume we had was my sister Sasha’s cowgirl outfit. My mom thought it would be very cute on me and since it was for Halloween she did not see any harm in it. I really didn’t want to wear it, but after I had it on for a little while it didn’t really bother me. The only real difference was the leather style skirt instead of britches.

My next memory of being in girl’s clothes was when I was about 13 and I got caught in the rain. We were visiting my aunt’s house in Glencoe and my cousins and I got caught in a very heavy rain. My clothes were soaked to the bone. When we got in the house my aunt and my mother insisted that we get on some dry clothes. My aunt, had a son, but he was much smaller than me and there was nothing of his that would fit me. Even his shoes were too small. My aunt didn’t think twice about getting some clothes from my cousin Mindy’s closet for me. I was dressed in a yellow polka dot girl’s jumper with a white nylon shell blouse that had one button at the top in the back as a clasp. I was even made to wear a pair of my cousin’s cotton panties since everything I had was soaked. I was given a pair of Mindy’s Mary Jane shoes to complete the outfit. I was completely decked out in girl’s clothes, but at least I was not made to wear a dress or something even more feminine than this outfit. I ended up wearing this outfit at my Aunt’s house for the rest of the day and was even forced to wear it home that evening. Fortunately we never left the house or the backyard so no one else saw how embarrassed I was. Like my first time as a cowgirl after a while I do not think I noticed what I was wearing. In fact, this outfit actually felt kind of nice but there was no way I was going to let anyone know that.

My only other pre-college dressing experience that I can remember was during my junior year of high school and I was encouraged to do it by my girlfriend Jana. It was during homecoming week and the school was having lots of activities and all sorts of school assembly entertainment skits. She convinced me to join five other boys in dressing up as cheerleaders and to do some campy cheers for the school assembly. It was something that had been done almost every year as part of the school spirit assembly for homecoming. We were all dressed up in cheerleader outfits complete with skirts and sweaters. We were even given pompons to complete our look. My friend Nick was also convinced to join the troupe.

It was all for fun, and at that time I didn’t really think much about it. The only problem with it was both Nick and I ended up being too good at pulling off the cheerleading skits and maybe a little to authentic. The four other boys, looked just like boys dressed in cheerleading outfits. That is, they looked nothing like girls. Nick and I on the other hand, actually looked pretty good in the cheerleading outfits. Jana and Rita borrowed wigs for us and even put some makeup on us to complete our costume. When we were out on the floor doing our routine, I was later told it look like two girls and four boys leading cheers. Nick and I even got wolf whistled at by some of the guys in the audience. I think they were trying to make us feel even more awkward than we already felt at the time. A couple of the real cheerleaders came over to us after our routine and asked Nick and I if we would like to do a few cheers with them. It was a little more than we could take and we declined their offer. I could tell that Jana and Rita were very much enjoying our little embarrassment.

I WAS DRESSED AS A CHEERLEADER

Fortunately, that was our last experience as cheerleaders or any other gender bending high school escapade. Jana managed to take a few photos of us while dressed as cheerleaders, I guess she did it so we would never forget that moment. Or at least never let us forget that moment. Looking back today, I am sure that seeing us dressed as cheerleaders had in some way influenced Jana and Rita’s encouragement of our current situation.

The four of us were very close, but we were also very competitive. We would bet on just about anything we could. Most of the bets were just for pride with very little monetary gain for the winners. Sometimes we would bet for something like movie tickets or dinner at the mall, but it was usually just for fun. Some of these bets, included sports like tennis, and also included card games, trivia games and especially games with dares. Sometimes these games of dares would get a little out of hand. None of us drank or did drugs or had any other really bad habits. But as I said, some of these games would get a little out of hand. A couple of these games dared the other couple to cross the line a little bit. It was one of these games, when I had my first beer. I was 16 and I didn’t like it at all. It was the only beer I drank before I went off to college. Most of these games were fun and usually not too weird.

Our freshman year at the University was pretty non-eventful. I was a Liberal Arts major, because I still did not know what I really wanted to do with the rest of my life. Jana on the other hand was enrolled in pre-med even as a freshman, she new she wanted to be a doctor someday. Nick was also in the liberal arts school and was thinking about majoring in theater or the arts. Rita was planning to major in psychology or sociology. She was very good with people and wanted to take advantage of that in her major. As freshmen, most of the courses we all took were pretty generic. We all had to take basic math, rhetoric and sciences. We were all very focused on our classes and studying, and doing pretty well with our grades. Our adjustment to college life had gone pretty smoothly.

We all lived in the same dorm, which was coed and located on the southern part of the campus. Boys and girls could not share rooms but at least we were allowed to live on the same floor. Nick and I roomed together and Jana and Rita roomed together down the hall. The arrangements at the school were pretty good, but the food in the cafeteria was horrible. I think during my freshman year I lost close to 15 pounds and I think Nick may have lost about 10. It wasn’t like we were that big to begin with but now we were pretty thin and almost wispy. I was about 5’8” and down to about 135 pounds. Nick was only about 5’7” and probably didn’t weigh anymore than me. Back in high school we were both much more athletic, but now in college we were much more focused on our academics.

Jana and Rita looked as good as ever. Both were about 5’6” to 5’7” tall and weighed about 125 pounds. We were very lucky to have such beautiful girlfriends. I think sometimes because we had been together so long we took our relationship for granted. Still I don’t think there was anything that the two of us wouldn’t do for Jana and Rita. It was probably that amazing relationship that was partially responsible for our unusual journey that began our sophomore year.

The summer between our freshman and sophomore years was very good one. I worked part-time in the concession stand at the movie theater at the mall. My Uncle was the general manager of the theater. It was actually kind of fun, because I got to see a lot of my old high school friends. I worked five days a week, but it was never for more than about four or five hours on any shift. Nick worked at the Borders bookstore in downtown Highland Park. The girls both worked as summer camp counselors through the park district. We all had plenty of downtime to hang out over the summer. By the time the summer was over, all of our batteries were recharged and we were ready to get started with our second year of college.

It was during new student week prior to the beginning of classes that was the start of the strange events that would follow. We were all just hanging out on the quad just laughing and having a really good time, when we started debating all sorts of odd issues. One of the strangest conversations we had, was who had the most friends that were gay. I am not sure what got us on this topic or what difference it made, but we started listing all of the friends we knew that were gay. There were a couple of friends that we thought might be gay, but no one knew for sure.

From that strange topic we somehow made our way over to feminism. The girls contended that we hardly knew anything about feminism. We strongly disagreed, and said we were very sensitive to the many issues that feminists faced. The girls laughed and Jana said we didn’t know the first thing about what it was like to be a woman. Nick and I laughed, and shot back they were making too big a deal out of it. We probably should’ve kept their mouth shut on this topic and then maybe we would not have gotten ourselves into such deep trouble. Jana and Rita almost immediately took on a much more serious tone. I could sense, that we had picked a bad subject to debate.
Jana and Rita decided to go for a little walk. They said they wanted to think about some of the things we had said and would finish the discussion later. I think we had hit a very sensitive chord with them. We hoped that after a little time to cool down, maybe the subject would just blow over. Nick and I just hung out listening to our iPods and napping. Nearly 2 hours had passed before the girls showed up to greet us. They seem to be in a much better mood and even gave us very affectionate kisses upon their return. As it turns out, they had not forgotten the conversation even if we had.

We all left to get a bite to eat. It was over a slice of pizza, that the challenge was made. The girls thought that a little education on feminism would be good for us. They also thought that knocking us down a couple of pegs would probably be good for our egos. They wanted to find out how far we would go to learn a little bit about feminism. Would we be willing to experience even a little about what it felt like to be a woman. We weren’t even sure how this was possible, seeing as we were red-blooded American males. The girls had other ideas. They had thought this through quite a bit and had come up with a most unusual challenge.

Rita laid out the challenge, and while we were listening we weren’t sure if she was joking or not. I am also not sure, if they really expected us to truly consider the proposal. The challenge was basically as follows. For each weekend throughout the school year we would be given one new aspect of femininity that we would have to make as part of our daily life. It would only be for the weekends, but each weekend they would add one challenge to the past weekends challenges. We were very confused by what they meant at first, until they laid out the first couple of challenges. The idea of the challenge would be to gradually add feminine aspects to our otherwise male existence. I think they thought by doing it slowly we would be more likely to give up, then if they asked us to bite the bullet and put up with all of their challenges for just one weekend.

They said that they would have a new challenge every weekend, which would run from Saturday morning until we went off to classes the following Monday. We were still a little confused, until they told us about the first two challenges. The challenges were meant to be very subtle, but over time we would certainly feel the effects. The first challenge, which would begin in two days on Saturday, was that we would have to wear panties under our clothes. Cotton briefs would be acceptable, but they had to be girl’s panties and could not be basic white. So as not to embarrass us too much, the girls said they would volunteer do the` shopping. They said we could do our own shopping it if we wanted to, but they would be willing to do it for us.

Just so that we understood where this was all going, they let us know what the second week’s challenge would be if we made it through the first weekend. The second weekend, we would have to shave our legs. Not that we had much hair on our legs, but the light hairs would have to be gone that Saturday morning. They also threw an extra twist, that we could not get a haircut or clip our nails without their permission. Both Nick and I had moderately long hair, but nothing really that unusual. My hair was light brown and covered my ears, but only down to about my neck. I probably could’ve used a haircut, but my hair was really not that long and pretty typical of students at the University. Nick’s hair was a dirty blond shade and was probably just a little bit shorter than my hair. The girls had obviously thought this thing through and really wanted to find out if we had the guts to go through with it.

As soon as they had laid out the challenge, I asked them what’s in it for us. The girl’s first answer was that it would be good for us. We laughed, saying being embarrassed is never good. On that point, I think the girls agreed with us. Most of our past bets have never really been about the prize for winning, it was usually simply about the thrill of winning and rubbing it into the noses of the losers. This strange challenge, was something a little bit more. If we were going to take their challenge, Nick and I were going to have to do all of he hard stuff. If we went through with it and met their weekly challenges, we felt the girls would have to do something for us. We were not even sure how long this challenge might last or how crazy it might get. The girls suggested, that we would run the challenge for the first semester of school and if we could make it to winter break, we would be entitled to some form of payback. If both of us could not make it to winter break, we would have to do something for the girls.

The girls really wanted to make sure that the two of us were in this together and therefore made all of the challenges dependent on both of us completing each step. If somehow we made it to winter break having completed all of their challenges, the girls thought that we could devise a new challenge for the spring. Frankly, we were not thinking that far ahead. After much debate, it was decided if we took their challenge that the losers would have to do all laundry for the winners during the following semester and would have to pay for dinners every Saturday night throughout that semester. Nick and I were given one day to decide if we were up for the challenge. We rarely backed down from challenges, but this one was quite unusual and deserved some overnight consideration.

When Nick and I got back to our dorm room that night we sort of looked to each other for guidance. We were not sure where to start the conversation. Clearly we were both very uncomfortable with what would be ahead if we were to accept the challenge from our girl friends. If we wimped out, the girls would win and forever remind us of that. If we took their challenge, God only knows what we would have to endure over the coming weeks. Nick was the first one to open his mouth, “How bad could it be?’’ I responded, “You know the girls, this could get pretty serious.’’

When we thought about it, we realized we knew very little about what could be in store. We really didn’t know much about girl stuff and therefore very little about what the girls might ask us to do. In a way, we were sort of admitting that they were right in the first place. The last thing we wanted to do was admit that, or at the very least let them know that. We knew the girls really loved us, so anything they might force us to do, probably would not hurt us. The girls would probably want to have a little fun with us, but hopefully in a sort of loving way. When we thought about it that way it made us a little less scared of accepting the challenge. We decided to sleep on it and make the decision in the morning.

I remember having some very weird dreams that night. Dreams are sometimes hard to remember, but I do remember being a girl in my dreams. I was walking around trying to convince everyone that I was not a girl and I was their old friend Michael. Everyone was laughing including Jana, Rita, and my mother. I think I remember crying and I don’t remember what happened after that. When I woke up the following morning I was more than a little restless.

Nick told me about some of his strange dreams as well. In his dreams he was a cheerleader again, but this time he was part of the real girls team. He was doing cheers with the other girls on the cheerleading squad. He said his dream even went further, and that he had a boyfriend on the football team. He was more than a little embarrassed relating his dream to me, but under the circumstances we were both more than a little freaked out by this challenge. Based upon how uneasy we both were that morning, we should’ve called it quits right then. After we had a little breakfast and a venti Starbucks, our uneasiness had drifted away.

Nick and I had one final discussion on the subject, and decided that if we were going to go ahead with this the girls had to throw in a little bit more. Since we were the ones that were being challenged, the girls had to do something for us along the way. First, we did not want to do anything that we did not think the girls would not also do, if we asked them. That way we could be assured that the girls wouldn't do anything really Goofy or way over the top. Secondly, the girls would have to take us out to dinner every Saturday night as long as we continued the charade. We figured that was the least they could do, while we were jumping through their hoops. Finally, so that we wouldn't be too embarrassed, we would make them promise not to tell any of our friends or their friends what we were doing. With these assurances, Nick and I would be willing to take their challenge.

That afternoon we met up with the girls at the Quad like the previous day and made our proposal. The girls acted only a little surprised that we had considered their proposition. As I look back at it now, somehow I think the girls expected us to take their challenge. They considered our modifications to their original proposition and were not completely happy by all of them, but reluctantly agreed to them. I am not sure to whom they would've wanted to tell or if they had any strange requests that now they could not make us do, but they seem content to go along with it. In fact, the Saturday night requirement that they would have to take us out to dinner, seemed to please them. They even said as a requirement of the bet, that every Saturday night we would go out to a place of their choosing and that we would be treated. If the girls didn't take us out, they lose the bet or if we didn't go with them, we lose the bet. It was agreed and the bet was on!!!

To our surprise before we headed back to the dorm that night the girls gave us each our first present. We were given a three pack of girl’s cotton panties. The package included one pink pair, one yellow pair and one blue pair. Since we had been with the girls all afternoon since the agreement, the girls must have bought these panties prior to us agreeing. When they handed them to us they both laughed a little bit saying that they would have just returned them had we not agreed. But they were pretty sure that they wouldn't have to return them. After they gave them to us, they said that there would be an inspection the next day. There was no turning back now.

They gave us a kiss on the cheek and then welcomed us to the girls club. For the rest of the year every weekend we would be honorary girls. They said they planned to treat us more like girlfriends than boyfriends on the weekends for the rest of the year. We did not like the sound of that, but we were assured that it was only a part of the game. The last little surprise twist that they dropped on us had to do with our names. As honorary girls, our names, Nick in Michael would not do. On the weekends, Nick would be referred to as Nicole or Nikki. Jana told me that on the weekends from this day forward I would be known as Michelle. Nick complained, saying this was going too far, but the girl said that we had to feel completely as girls in order to understand feminism. Truthfully, we had already forgotten what had caused this challenge to be proposed in the first pace and at this point were too talked out to debate. I guess their was some logic to their argument anyway. At this point it really was not that big a deal, but it seemed that their purpose in giving us those names was just to humiliate us a little bit more.

Nick and I headed back to our room feeling dejected, like we had already lost a little bit of our pride. This whole thing had gone much further than we expected it to, and that it hadn't even really begun. We were already nervous about what would happen in the weeks ahead. Neither of us said anything else about the whole subject until we got up the following morning. Living in a dorm is not like living in an apartment where you get a lot more privacy. We would have to be very careful, so that no one else would see that we were wearing the panties or anything else that might come our way. Fortunately, we had closets that locked. We would just have to be a little extra careful when some of our floor friends were around. On Saturday morning after taking our morning shower we experienced our first part of the challenge. Nick chose to wear a yellow pair from his package and I selected a blue one from mine. We slipped them up our legs and commented that they didn't feel all that bad. They were actually softer than our jockeys and fit us pretty well. There was no fly for us to use, but that was no big deal. The panties were made by Haynes, which also made men's underwear. These were clearly not men's briefs, but unless somebody saw us with our pants down, no one would know. The first challenge was pretty easy, and truthfully felt pretty good. Nick even commented, “That they should make men's briefs out of the same soft type of cotton.”

When we met the girls for lunch on Saturday the first thing they did was greet us with our new names Michelle and Nicole. I think that was to get us into the mood and to let us know what might be ahead. The girls took a peek at our waistbands to make sure we were wearing our new briefs. Satisfied that we were wearing our girl’s panties they congratulated us on our first step towards understanding feminism. The rest of the day was pretty relaxed and the girls took us out for veggie burgers and salads. We wanted regular burgers and fries, but the girls insisted that we order a veggie burger and a house salad because we needed to watch our figures. We didn’t make a big deal and enjoyed watching them pay the check. When Sunday rolled around, it was no big deal putting on a fresh pair of panties.

That Monday was the beginning of the new semester of classes. The focus shifted from having lots of free time and the challenge to getting back into academics. The week flew by until Friday evening when our girlfriends handed us each a Lady Bic razor. We were told that our legs had to be hairless from the tip of our toes all the way up to our privates. We didn’t have to shave our little triangle area, but our legs had to be completely free of hair. They said if we preferred we could use a product like Nair but for now shaving our legs seemed like the best way to get the job done. Rita explained, “It’s a ritual that all girls have to do at some point or another.” As much as they wanted our legs to be free of hair, I think the experience of shaving them was part of the challenge.

We didn’t want any one from the dorm to see us shaving our legs. If we did get caught shaving our legs, we planned to just explain it off by saying that we’re planning on doing a lot of biking and many bikers like to have their legs free of hairs. It was a pretty lame excuse and I’m not sure how well that might have worked. We slipped into the shower area late Friday night, when we didn’t think there would be as many people in the bathroom. I think we both learned to appreciate what women go through to shave their legs. It took longer than we expected and was not that easy. I even nicked myself down near my ankle. Neither of us had that many hairs to begin with, but it felt a little strange not to have any hairs after we were done shaving our legs. Though people probably wouldn’t even notice that we had shaved legs, they certainly felt different to us.

The girls commented how nice our legs looked and even mentioned how great they would look with a nice pair of high heels. We gave them a dirty look and just let their comment pass. It was already mid-September, and the fall weather was already starting to lose some of its summer warmth. We wouldn’t be wearing shorts much longer, so having to shaved legs was not going to be a very big concern. It was kind of strange, just like having worn cotton panties for the first time, having smooth legs really was not all that bad. So far, the two challenges actually felt kind of good and more importantly, no one else could tell. Nick and I both were a little concerned about what was a head, but we decided not to talk about it very much so we wouldn’t raise our anxiety level. Much like on the previous Saturday night dinner, the girls treated us to a healthy and very light dinner. They were paying the tab, so we chose again not to complain.

School was going very well and we are all studying very hard. Despite the strange challenge that was going on between us, my relationship with Jana was never better. We were together as much as possible and had a great sex life. She seemed to enjoy seeing me naked with only my panties on. It was probably a little kinky, but we both had a lot of fun with it. She particularly liked to cuddle with me more.

Week three brought us our first surprise. We had no idea what the girls were planning for us but knew we would find out on Friday evening. The weekly challenges were supposed to be very subtle, so we tried not to be too scared. On Friday evening we were the recipients of our first manicure. The girls gave us each a very basic manicure that cleaned up our nails and gave them a slightly more oval curve. Our nails were not very long, because Nick and I were smart enough to clip our nails before the challenge began. It didn't leave the girls that much to work with. When they were done filing our nails, they gave us a double coat of clear polish. The girls told us that lots of guys have had their nails done and wore clear polish. That did not make us feel any better and our nails would be very obvious to anyone who really looked closely. This was the first challenge that we really didn't enjoy.

All week long in class I couldn't help but stare at my hands. I guess my hands looked nicer, but only if I was a girl. It felt strange when I looked at my hands, because it felt like I was looking at someone else's hands. It really wasn't too bad, but whenever I took notes in class I would find it a little distracting. Nick told me he felt the same way and found he kept his hands in his pockets more then he would have otherwise. All week long, the girls had to keep telling us to take our hands out of our pockets. They told us we should be walking with our elbows in, and our hands out. When we tried that, we realized it was a much more feminine way of holding our arms. We would sometimes hold them like that when we were with the girls, but most of the rest of the time we would hold our arms like we normally did. It's kind of funny, as guys, he never really thought about how our arms were positioned, but as girls we were much more conscious of how our arms hung from our shoulders. The girls suggested that down the road maybe we should go in for a more professional manicure. That Saturday, we went out to a very romantic French restaurant. The only twist on dinner that night was that Jana had made the reservation under the name Michelle. When we checked in, I told them that my name was Michelle. When the maá®tre d’ gave me a strange look, I told him my parents were French. He smiled at me and that was the end of it.

Week four brought us our first challenge that could not so easily be explained. Again it was something subtle, but also very girly to us. The girls gave our feet a manicure, but this time they painted our toes a bright red. We were pretty much done wearing sandals for the season, but anyone who saw our feet would probably have a good laugh at our expense. We would have to be very careful when we took a shower at the dorm, so that no one could see our feet. We wore closed toed slippers to the shower and made sure we didn’t go in when it was too crowded. Seeing our shaved legs and pretty toes was starting to make me a little odd. It had been about two weeks since I had last shaved my legs so I had to do that again. These female rituals were starting to affect my psyche. Technically, we could have taken the polish off Sunday evening but then we would have had to put it back on ourselves again the following Saturday morning. It just seemed easier to leave it on and try not to have anybody see it.

The girls were clearly having fun with all of this. They kept asking us how we enjoyed our pretty hands and pretty feet. They said it was like teaching a young girl to be a woman. They also said that we were very good students. Up until this point we had been a little bit apprehensive about the challenges, but had never really considered backing down. The next week’s challenge was the first one that we really complained about. We even said it wasn’t fair, because it was sort of permanent. Week five brought us to the mall to get our ears pierced. A lot of our friends had the one pierced ear, usually the left one. But the girls insisted that we get both of our ears pierced. Again, they told us that lots of guys do it, and if we didn’t like having pierced ears that the holes would fill in slowly when the challenge was over. That didn’t make us feel any better. We put up quite a stink until we got to the store. When we got into the store we meekly let them pierce our ears, so that the clerks did not think that the girls were forcing us to have our ears pierced. The girls bought us each a couple of pairs of earrings. The first one had a very basic gold stud, which we would wear for the first week or two. The second pair was clearly more feminine with a small silver hoop. Our hair had been growing pretty long, so we were hopeful that nobody would really notice our ears peaking out from under our hair.

I felt like I had been branded a girl. This challenge now felt like something that wouldn’t just wear off. It was not something you would do to someone for a quick laugh over the weekend. It was something that would be with you for a long long time. Back then I wondered why the girls would want to do something so permanent. They commented how wonderful we looked and that they really liked them on us. Instead of telling us how handsome we looked with them, they told us how pretty we looked. It was around this time that we noticed the girls were starting to call us by our female names a lot more. When we were in the store, Jana said to me “Michelle, Do you see any other pairs that you would like?” I wanted to just disappear.

We were now about six weeks into the semester and my appearance was really beginning to change. I had dropped at least a couple more pounds and my hair was getting fairly long. Combine that with my polished nails and earrings and I was starting to take on a somewhat feminine look. I really wanted to get a haircut so that some of the other changes would not seem so dramatic. Nick was feeling the same way and I had to admit he was looking more and more girlish. Clearly, our appearances were beginning to change. The girls were being very careful watching what we ate and trying to teach us more girlish manners. They were working on both our physical looks and our psyche.

The week six challenge was an easy one. We were already shaving our legs, so the girls insisted now that we remove the rest of our hair on our body except on the top of our head and around our private area. We gladly accepted this challenge because we assumed at this point that it would be no big deal. This meant that we had to remove the hair from our arms, chest, under our arms and anywhere else we had stray hairs popping up. Neither of us was very hairy to begin with, so it would be easy to comply with. This was a pretty easy challenge since no one would notice unless of course they saw us completely naked. Friday night I slept in Jana’s room with her, while Rita slept back in my room with Nick. Jana and I made love that night like never before. She told me she was so turned on by my smooth body that it was driving her crazy. How could I complain when we were having such passionate fun.

Being smooth all over actually gave me a rush. My clothes somehow felt different and I was much more sensitive to the different materials I was wearing. I remember rolling over in my bed and wrapping my body in my soft sheets. I had the sheets tightly encasing my hairless body and thinking how wonderful it felt. The experience was so arousing that I found myself having an accident on my bed. I could not believe it but I was getting turned on by some of the sensations of this challenge. As much as I enjoyed the feeling, I was not going to let Jana or even Nick know what I was feeling. I didn’t know what was happening to me and I was feeling a little guilty.

The week was moving along quickly with some midterm exams in calculus and biology. When Friday rolled around I was exhausted from all the studying and from the near all night study session on Thursday evening. I knew that we would be learning our next hurdle on Friday and was really almost too tired to care. We met up with the girls at five o’clock in the union building cafeteria. I was not in the best mood, mostly from being so tired. I got both Jana and Rita upset when I snapped, “what hellish torture do you have in store for us this week?” The girls were pissed off by my tone and the nasty content of my complaint.

Rita shot back “that they had been easy on us and that we seem to all have enjoyed the experience so far.”

Jana was noticeably upset and piled on “if it was such hell that we could just quit and go back to being chauvinistic pigs.”

A few more barbs were exchanged, before Nick cut in and told everyone to take a chill pill. Nick broke the painful tension by comparing the discussion to a catfight between four girls. It was just enough to cool all of our jets and bring a small smile to our faces.

I took the temporary silence is an opportunity to apologize to Jana. I explained my remark off, by telling her how tired I was. I said, “The only thing I really wanted to do is go home and hit the sack… the sooner the better.”

Janus smiled back at me with a very sincere, yet mischievous look. I looked at her and said “what?” She smiled back and replied, “then you will be able to take advantage of your next treat even sooner than we planned.” The girls reached into their backpacks pulled out gifts for us. We each were handed a thin white box from someplace called Sonoma. The boxes had a small bow and some pale yellow ribbon on them.

“What’s this?” I quickly responded.

“This will help you sleep a little better.” Said Jana

“Open it, open it!” An excited Rita chimed in.

Nick and I wasted no time opening the boxes to see our new gifts. When I saw what was inside I was a little confused and somewhat startled. Nick was first to pull his full-length black satin nightgown from the box.

He laughed and said “he could not wait to head back to the dorm and see Rita in it.”

Rita just smirked and slyly quipped “yeah right, you know that is for you not us.”

Nick looked like a deer in the headlights. He carefully put it down and then back in the box.

“You don’t really expect us to wear these, do you?” Shot Nick.

“We would look like total dorks in these.” Nick continued.

Jana cut in “you will love the way they feel on your smooth bodies. You should be thrilled for the opportunity, besides only the four of us will probably ever see you in them.”

“Probably?” Screamed Nick.

I had said very little throughout the crazy scene. I looked at the nightgown and thought about the evening earlier in the week when I was wrapped up in my bed sheet.

About the only thing I said was “if we have to…”

The girls said they had also gotten matching ones for themselves in red. Rita said “we could exchange ours for red if we preferred.” Neither of us responded to the comment.

The girls were meeting up with a few of their classmates for a girls night out and left the two of us to our own new treasures and fates. We knew it was way too late to turn back and like most of the other challenges maybe we were making too big a deal of the most recent hurdle. Psychologically it might be hard to wear the nightgowns, but then again, no one besides us would know.

I was planning on heading back to the room and going straight to bed. Under the circumstances, I suggested we go out and have a bite. Dinner led to a couple of drinks and it was after 11 before we made it back to the room.

When we got back to our room we both showered to get and to get the bar smell off of our skin and prepared ourselves for bed. Knowing that we would be wearing our new gift we took our time getting cleaned up, probably not too unlike what a girl would go through getting ready for bed. We were both very slow and very methodical.

It was time to crash, so we locked our doors and checked it twice. We slipped into our new nightgowns almost effortlessly. I was not sure if I should have worn my panties under it, so I decided to wear nothing but the gown. It tickled my smooth skin all the way down. It took me less than a heartbeat to get aroused by the feeling. My obvious state did not go unnoticed, and I was not the only one to feel the effect.

When I saw Nick in his nightgown I was stunned. Throughout this experience I had never really thought of him in a really girlish way. However seeing him with his gown hanging over his slim body he actually looked quite pretty and delicate. For the first time I saw his blond hair brushing his neckline and from behind I would almost certainly have assumed he was a real girl. That thought sent strange chills down my spine. I was too scared to look at myself in the full-length mirror that hung from the back of my closet door.

Nick turned around and started staring at me. His look was creeping me out. I asked him “what are you thinking?”

He looked at me and said “hey Michelle are you dating anyone these days?” He chuckled a couple of times and felt compelled to mutter, “just kidding.”

He mentioned how absolutely amazed he was that I looked so fabulous in the gown. I told him I felt the same way about him and his gown. Were both in such a shocked state that I’m not even sure who flicked the lights off.
As tired as I was, I still think it took me over an hour to fall asleep. My body was going crazy all over because of the silky sensations. As a result, I had a hard on that just wouldn’t go away. With no privacy in a shared dorm room, I just laid there until I finally passed out.

The next morning I headed over to the library to study and meet up with Jana. At about 11 o’clock she showed up with a big grin on her face. She smiled at me and asked how I slept. I lied and told her it was a restless night. She said she couldn’t wait to see me in my gown later that night. I was not so sure, but said I wanted her to wear her new nightgown as well. She smiled at me and said it would be so much fun.

Saturday night we went out for stir-fry food and a movie. The girls took us to a chick flick called Maid of Honor. It was about a guy that was the maid of honor at his true love’s wedding. It had a lot of gender jokes, but nothing like what we were going through. Jana joked that Nick and I would have made much better bridesmaids than Patrick Dempsey did in the movie. “We would have been much more believable and a lot prettier,” quipped Rita. The girls were definitely trying to play with us. It probably was not too difficult either, because I found myself thinking about being a maid of honor throughout the film. As silly as the movie’s premise was, my psyche was quite fragile.

After the movie we had a nightcap at the pub next to the theater and then retreated back to the dorm. Jana ordered me to shower, shave all over, and bring the nightgown back to her room when I came. Nick received similar marching orders from Rita.

When I got to her room, I assumed we were going to just hit the sack. I was excited for that, even if it meant modeling the new gown. Instead when I got to her room, she said we need some girl time together. She had me slip on my black nightgown and gave me a sweet but short kiss after I put it on. Over the next hour or so we redid each other’s nails and she spent a good 10 minutes brushing and playing with my hair. We talk about mostly girl stuff like fashion, gossip, and our feelings.

By the time we made our way to the bed I was very relaxed and feeling pretty good. Jana looked gorgeous and quite sexy in her red gown. We embraced and fell to the bed. It was a sea of satin and I was ready to explode way too soon. She could see how turned on I was and tried to slow me down. She had suggested that before I could enter her that I should satisfy her like a woman. She spread her legs and pulled her gown up to her waist. With my head between her legs she had me bring her to an orgasm twice. Only then did she turn to satisfy my hunger. She rolled over on top of me and pretended much like she was making love to another Woman. She kept whispering “Michelle, oh Michelle!” finally she moved down to my legs and sucked me until I exploded. When I did, I squealed much like she did. I had never entered her, but it was still very passionate sex. Were curled up together and fell asleep in each other’s arms.

I was not sure what was happening to me, but with each challenge, I seemed to be changing more. Each time a challenge was proposed, I accepted it with much reluctance. But with each challenge, I seem to be enjoying them more and more. I would have thought something was wrong with me, but in each case, Nick seemed to be enjoying it also. It was for this reason that I didn’t think anything was seriously wrong with me, and I felt less guilty about the whole thing. Jana certainly was having fun with it and I knew she knew I was sort of enjoying it as well. I never came right out and said that, but because of some of my lack of resistance, she must have picked up on. To this point, it seemed like just some kinky fun. It was mostly something between us, sort of our little secret.

Nick and I only had to wear our nightgowns over the weekend. On Monday through Thursday we could go back to wearing whatever we wanted. On Monday, I wore an old pair of flannel pajamas, like I usually had. I remember going to bed and commenting to Nick that they felt fairly rough on my skin. With no hair on my body, the course material of flannel, felt sort of rough. Nick agreed, but said very little other than that.

On Tuesday evening, I turned in a little earlier than Nick. When it was time to get undressed I was torn as to which pajamas I was going to wear. I could not believe that I was actually considering wearing a nightgown on a night when I didn’t have to. I really enjoyed how it felt on my smooth skin. I quickly put on the nightgown and turn the lights off. I slipped under my blankets as if I was hiding from Nick and the world. Nick came back to the room before I was asleep and could see the top of my nightgown slightly sticking out from under the blankets.

“What’s with the nightgown buddy?” Said Nick not caring if I was sleeping or not. I really didn’t have a great answer for him, but I said something to the effect that with no hair on my body, my regular PJs felt uncomfortable. He either bought it, or didn’t care. He did not wear his nightgown that evening, but a couple of nights later, Nick had his on. I wasn’t going to change back, but I felt less guilty knowing that Nick had followed my lead.

That Friday, Jana and I went out to dinner alone. She asked me how I had been doing and if I was holding up okay. I did not like keeping any secrets from Jana, so I told her some of my true feelings. I held back a little, so as not to seem, like I was having too great a time with it. But I did tell her, that it had been sort of fun and that some of the girl stuff actually felt kind of good. She said, she could see some changes in Nick and I, and for the most part, that they were very good. She said she also liked the subtle changes in our personalities. I asked her what she meant, but she couldn’t put her finger on it, other than to say she felt closer to me.
Over the past weeks, the girls had unveiled the new challenges when they were ready to. For some reason, maybe curiosity, I inquired early Friday evening, what the new one would be. Jana said “that since I had apparently enjoyed the evening gown so much, that I needed something to remind me of that softness all day.” She pulled out of her backpack a couple of bags and placed them on the table. One was from Macy’s and the other from Victoria’s Secret. She explained that it was time for Nick and I to upgrade our underwear to lingerie. We needed to feel even more girly under our daily clothes.

I do not understand, we are already been wearing cotton panties.”

“That is a good start, but you both are special girls and needed to experience some nicer undergarments”.
In the bag from Victoria’s secrets, were three matching sets of panties and camisoles. Unlike our cotton panties, these were silky smooth, just like the nightgowns. At their top and along the edges of the panties were some very dainty lace edgings. She told me that a camisole was much like an undershirt only infinitely sexier. And in the bag from Macy’s were a whole bunch of different types of leggings. There were a couple of pairs of waist high nylons, a couple of knee high pairs, some very femininely styled socks, and a pair of tights that ended at the ankles. I asked her about those immediately, and she said they were very stylish. Even more so than wearing just panties, this ensemble would be a constant reminder of our gender bending ways.

She told me how proud she was that I had been cooperating so nicely. I remembered that the one time I complained, she almost bit my head off. The girls had obviously been giving each of these steps great thought. Each one was just a gradual addition to the previous week’s challenge. Had they jumped ahead a couple of weeks, we might have balked. But the way they had been staging the challenge seemed to make it go with less resistance. I accepted the two bags from Jana and thanked her. I do not think I had thanked her for any of the previous gifts or should I say challenges. They had obviously spent a fair amount of time picking out the items for the two of us. She knew what sizes to get, and always seemed to pick out things that I might have selected, if I had been picking out things for her.

I was concerned that with the new camisoles that they may be visible through my shirts. She did not seem too concerned, and said that was part of the fun of it anyway. She then added, “Maybe it’s time to get you a few new shirts.” I was pretty sure I knew what she meant, and told her I was in no rush. She smiled at me and said, “ I think we will all know when the Michelle is ready to look a little nicer.”

The weather had definitely turned cooler and most of the time I was wearing heavier clothes, which fortunately would cover my new fineries. She wanted me to go into the bathroom and put on the items right then and there, but I told her it could wait till we got back to our rooms. Jana was a little disappointed, but still very excited that I had taken her gift and not complained even one little bit.

Throughout the challenge I had wondered if the girls really felt we would go through with the whole thing. At the beginning, the whole thing seemed quite outlandish. With each step and each new wrinkle, we had been digging ourselves into a deeper and deeper hole. The whole thing could have put a wedge between us, but it seemed to be drawing us closer and closer together. Some of that bonding was clearly sexual, but some of it was more like just friendship bonding or should I say girlfriend bonding. Jana and I had a great thing going. I did however wonder, what would possess a girl to turn her boyfriend into more of a girlfriend. Maybe Jana and Rita were Bi. Someone once told me that all girls are Bi to at least some extent. At the time, I blew off that notion. I was now feeling maybe there was a little truth to that. Whatever was their motivation, they certainly were enjoying seeing us experience a little girlhood.

I was clearly losing a little bit of my male mojo. The moment I put on my new lingerie I became aroused. Jana had me model it for her that night and giggled as soon as she saw my erection. She walked up to me and gave me the most passionate kiss I had ever experienced. She hugged me and dragged me over to my bed. We fell over onto the bed like a fallen tree. I think she kissed just about every part of my body before relieving my throbbing organ. We were having so much fun together, that she knew I would do almost anything for her.

There was only about two weeks left in the semester prior to Thanksgiving break. We would all be going home to spend the holiday with our families. I was a little concerned that some of the subtle changes in me might be too obvious. It was all for fun, but the family might think it was a little weird. Even if I could cover up some of the externally obvious changes, like longer hair, my hairless body, the long polished nails, and of course the pierced ears, someone could still notice my new undergarments. I was going to have to come up with a strategy for Thanksgiving, but so far, I hadn’t figured it out yet.
Nick was going through much of the same internal conflict that I was going through. We had not discussed it that much, but he was clearly becoming more and more feminine. His hair was much longer and now seemed at least as long as mine. Both of us were in desperate need of a haircut. There were of course the obvious changes in clothing and female hygiene that we were both experiencing, but beyond that, he seemed to be much less masculine. His posture seemed to be different and for some reason he seemed to be moving a little different. Maybe I was doing the same thing, but it was easier to see that with my friend Nick. His relationship with Rita seemed very strong and they hung out as much as possible. During our freshman year and earlier in the semester Nick and I spent most of our free time together. More recently, Nick would spend his free time with Rita and I would spend my free time with Jana. This was okay, but I did enjoy my time with Nick whenever we had it.

During the middle of the week I expressed my concern to Jana about the Thanksgiving holiday coming up. Maybe I was looking for a little sympathy or possibly some idea how to get through Thanksgiving with a minimum of fanfare. She said she would discuss it with Rita and give it some thought. She told me not to worry and that everything would be fine. I trusted her implicitly, but had no idea what to expect. She said every challenge had been subtle when compared to the previous week’s challenge and future ones would be no different. It was only two weeks to Thanksgiving, so not to worry. I would have been worried, even if there had been no new challenges, and I am sure that Jana could read that on my face.

“Only two more challenges before we go home and only six more weeks and we win the semester bet,” I related to Nick on Thursday morning before we went off to classes. He said he wasn’t sure if he could make it to the end of the semester, let alone Thanksgiving. I told him we were in this together and would somehow survived together. He was scared about going home for the holiday, because he was not sure how his family might react to seeing the way he looked now. I was planning on going home that Friday right after classes ended, but he said he was not going to go home until the Monday before Thanksgiving. He was going to use the excuse that he had a lot of work to get done, but the truth is, he wanted to put it off as long as possible before his family saw him. I certainly understood where he was coming from, but I really wanted to see my family and needed a break from campus.

We were still getting together every Saturday night as we had laid out in the challenge. This coming Saturday, would be our last dinner together, prior to break. The two Saturdays over the break would be the only weekends that the girls would not have to take us out. So we planned to have a nice celebration together on Saturday. The girls were going to take us out to our favorite Italian restaurant and we would go dancing afterwards at our favorite club called “Chances R.’ With the holiday right around the corner.
On Friday afternoon all four of us were hanging out at the union building after classes. Rather than wait till the evening, the girls thought it would be a great time to layout our next challenge. The girls felt obliged to discuss the next challenge prior to telling us what it was. They said we had been good sports all along and they knew that the holiday was around the corner. They didn’t want to ruin the holiday for us, so for the holiday they did not want to do anything that was too far out there. We were relieved to hear this, but a little skeptical. They reminded us how in our first challenge we wore panties and could barely tell the difference. They explained that a lot of girl’s clothes are really no different than boy’s clothes. Sometimes the sizing is different, sometimes the fabric is different, and of course sometimes the styles look a little different. They went on to say, so much of what we wear is really uni-sexual. We were not sure where this was leading.

It was then, that the girls said, that we needed to start upgrading our wardrobe. We really did not like the sound of that and asked in what way?

Rita was very quick to say, “In a very subtle way.”

“In what way?’ I asked.

Janet took this opportunity to cut in “you guys have lost so much weight, that your pants are practically falling off. We thought, that this would be a great time to buy you some new pants and slacks.”

Rita chimed in “pants are pants and the ones we picked out for you will clearly fit better than the ones you are wearing right now.”

They were probably right about the pants we were wearing. They were pretty worn, and probably at least a couple of sizes too big. I’m not sure how much in total weight we had lost, but a few of our pants were nearly falling off. As it pertained to our current pants, we would have had a hard time arguing. We were more concerned with what they had picked out for us. Until now, all of our new apparel was for under our clothes or only to be worn at night. Now they were suggesting that we wear girl’s clothes on the outside. We thought this was very unfair, especially with the holiday right around the corner.

Jana said they had bought us each three pairs of new pants and that on two of them they claimed most people would be very hard-pressed to know that they were not boy’s pants. On the third pair, she added that they were only a little bit more feminine and also not obvious to everyone.

The first pair were new Blue Jeans. My pair was a size 8 and came from the Guess store. That had some sort of squiggly design on the back pocket, but otherwise looked a lot like jeans I normally wore. The second pair of pants also was very jeans like, but was black and made of a more stretchy type of denim. Jana expressed “that since we were so skinny, these were our skinny jeans.”
The last pair of slacks was a lot dressier and also black. These slacks were much fuller in the legs and made of a much softer material. They were not made of the same satin like material that we had become accustomed to with our undergarments, but in their own way they also were very smooth and silk like. They seem to have more material than they really needed in the legs and I could see no pockets on them. Rita pointed out that they were very comfortable and the legs hung straight down from our waste. She said they were a little dressy, and would be perfect for going out Saturday night.

I lifted them up and they almost seem like a long skirt. I did not see how they could be mistaken in any way for boy’s pants. Janet told us we would love them and reminded us that it each step of the way we eventually enjoyed their little challenges. The other pants she pointed out would not look or feel any different than our old pants, but only fit us better. Over Thanksgiving, they said we would not have to wear the dressier slacks. This did not make us feel that much better. Rita even said that since the regular pants were hardly a challenge, then at least we could give it a try and wear the dressier pair once for them. I somehow hoped that they would not fit, but so far during the challenge, the girls managed to get our sizes perfectly.

Nick and I looked at each other and said we would do our best. The girls seemed to perk up and said we would all have a great time on Saturday. We are not so sure, but then, we were not so sure many times previously during the semester.

They asked us to go into the men’s room put on our new blue jeans. Nick and I were in no mood for arguing so we meekly complied. We came out with our fancy new duds on and the girls gave us a very quiet applause. The jeans fit us almost perfectly. We didn’t want to admit it, but they looked much better than the pants we had on before. It was almost as if they had been made for us. We thanked them and headed back to the dorm.

The girls walked ahead, which gave us a chance to chat a little bit. We both agreed that these pants were not so bad and if we could make it through Saturday, we would only had one more challenge prior to Thanksgiving. We were resting a little bit easier knowing that there was only one more surprise before we headed home for the holiday.

When we got back to the dorm the four of us had a quick bite in the cafeteria. The food was, as usual, very bland, but at least it was free. After eating we all went up to the girls room to hang out. The girls had some wine spritzers in the fridge, so we planned to just relax and kick back. Rita popped her iPhone into the sound-deck to create a little atmosphere in the room.

It was nice doing nothing for a change. We had all gone through midterms and all were grateful for some R. and R. We shot the breeze complaining about classes, the cafeteria, and any other crap we had on our minds. After a couple of drinks the girls turn the subject to fashion. They started probing us as to our likes and dislikes. The focus was totally on the female side of the clothing ledger. They wanted to know what we thought was pretty and were indirectly trying to educate us on women’s clothes. They pulled some of their clothes out of the closet as if they were doing a show and tell presentation. Since we were all so relaxed, the learning experience seemed so unforced.

The evening took a most unexpected turn. All four of us ended up spending the night in their room. We all wore our nightgowns and stayed up very late. It was kind of like an all girl slumber party. There was no sex play, but we were all very snuggly and often curled up together. The strangest thing was that I found myself at one point lying next to Nick. When Rita got up to get some water it was just the two of us in the bed and Nick’s body was clearly plastered against mine. When I first noticed the change of partners I was a little shaken, but after a momentary flash of fear, I felt oddly okay with it.

Nick was lying behind me and we were both on our sides. We were pretty tightly pressed up against each other, partially because the bed was only a twin and also because their were so many pillows on it. Nick’s arm was resting on my shoulder. I thought the booze and the girl’s night experience had desensitized me to the obvious unexpected turn of events. I had never even considered my good friend as anything other than a best friend. However, here I was curled up with him on a bed in a girl’s dorm room. When Rita returned, with a bottle of water she slipped into the other bed with Jana. Nothing was said between us about the twist of circumstances, but we were all aware of the change of bedfellows. There was very little additional conversation before we all drifted off to sleep. Nick and I ended up sharing the bed for the night. No real advances had occurred between us, but I would never have imagined that I might share a bed with another guy.

When I woke the following morning I was laying directly up against Nick, face forward. We were not hugging, but each of us had an arm over the other in an affectionate embrace. I was staring at my friend and trying not to move a muscle. I could not figure out how I got here and what if anything it meant. I looked over at Nick and at this moment he looked to me to be more girl than boy. It was more than just the physical ambiguity, but also the way he was responding. I lied awake for a few minutes, just staring and thinking about the crazy situation. As I stared at Nick, I kept visualizing him as being a girl. It was during one of my spacey dream states that Nick opened his eyes. He saw me just staring at him with my arm around him. He paused for a few seconds, then a small smile formed and he gave me a small peck on the cheek. It caught me by surprise, however I did not recoil. Almost instinctively, I asked Nick how he slept. I was talking to him not unlike I would have spoken to Jana after spending a night together.

Jana and Rita seemed to still be sleeping across in the other bed. I thought this would be a good time to exit. I slowly began to unravel myself from Nick. Neither of us seemed overly anxious to separate. Just before I got up I looked down on my friend and stared into his eyes and gave him a soft kiss across his lips. I had not thought it through, but at the moment it felt just right. As crazed as my action was, Nick clearly enjoyed my advancement. When I started pulling away, he put his free hand gently around my neck, and pulled me back to him to give me a slightly longer and more passionate kiss.

I quietly slid myself out of the bed. When I sat up I heard the girls finally waking with some morning groans. I said I was going to shower and head back to my own room. I slipped on my clothes from the previous night and glided out of the room. I felt almost like I had a mild morning hangover even though I really had not drank that much. I think it was the sensory overload my mind and body had experienced that was causing my impaired mental state. I took an extra long shower time to get my head back on straight. I just stared down at my red toes not really caring if anyone might notice. This whole game had taken me places I never expected and if anyone had commented about my painted toes it would've seemed almost insignificant.

I brushed my teeth and hair and then made my way back to my room. I put on my new black jeans, which fit me much closer up and down my legs. They were stretchier and clung to the shape of my legs. Other than being somewhat tight in the crotch area, they felt okay. I didn't give much thought to how they might actually look on me. My mind was still racing from the seemingly surreal events, so I was not completely thinking straight and not focused on my appearance.

I went down by myself to the cafeteria and had some toast and some bitter coffee. When I returned to the room Nick was in there changing. He looked at me with a sideways grin, but no direct eye contact. Our conversation was very muted and skirted the real substance of what was on both of our minds. I told him he could meet up with me at the library if he wanted to. I then texted to Jana where I would be heading. I was in no frame of mind for any deep conversation. She texted me back, "Catch up with you later… love Jana."

I spent the whole morning at the library alone with not even a peep from my friends. It was about 12:30 PM when I went back to the dorm to have some lunch and see if anyone was around.

I dropped my backpack in my empty room and walked down to the girl's room. Jana was in there alone working on a paper. She was genuinely excited to see me and after opening her door gave me a big hug. She said she did not come to the library, because she thought I might like a little personal time. I accepted her answer and went inside to be with her.

She was careful what she said, but asked me basically how I was doing. Without admitting that I was slightly mixed up, I gave her a rhetorical answer "fine." She shot back, “If I don't want to talk then what was I doing in her room?”

I was going to say something I might have regretted, before I caught myself and told her I was not myself. I told her that cumulative weekly effect of the challenge had started to make me feel different. I could not put a finger on it, but then I was trying to figure out what was really happening to me. She was sympathetic to my turmoil, but said I should just relax and go with the flow. She said that I was so lucky to be experiencing things most men never have the opportunity to and that it would make me a better person.

I told her that I was okay, but that I was getting emotional about the recent events. I did not say anything about the kiss, but I really didn't have to, since Nick and I had basically slept together.

She sat next to me giving me a short but sweet kiss. She rubbed my shoulders and explained to me that she knew that somewhere along the way Nick and I would hit that point that we might feel overwhelmed by conflicting emotions. She told me to accept the feeling without guilt. It was easier for her to say, than for me to do.

I told her that while I enjoyed the opportunity to experience some decidedly female times, I was having trouble being my old self the rest of the time. She told me to forget my old self and accept the new more rounded person I had become. I was not sure what I really wanted, but for sake of discussion I said I would try.

We went to have some lunch and then went back to the library to study. Before we left for the library she had me put on her UGG boots. She said they went much better with my nice jeans. The jeans actually had to be worn inside the booths since the pants were so snug. The boots were probably a size too small, but felt pretty soft inside. We were planning on meeting up with Nick and Rita later in the day for our fancy dinner out.

We had a productive afternoon at the library and before we headed back, Jana asked if we could stop in town for a few minutes. Our stop was really a stop for me. Our first stop was at the shoe outlet. She picked out a pair of UGGs for me. They looked much like her pair that I had been wearing, but they had a white furry band at the top. I was not expecting this additional challenge, but she said I really needed them for the winter. She then turned to a dressier section of the store to find a low-rise black leather boot to wear for the evening. She picked out a black leather pair with a 2-inch heel and a zipper on the side. They only rose slightly above the ankle, but she said she really liked them because they could be worn with almost anything. She asked me my opinion of the shoes and I said I thought they were pretty and a good choice. She then grabbed the box and said I should try them on before I bought them. Until then, I thought they were for her and only then realized the truth. I momentarily balked at the suggestion, saying that I didn’t need another new pair of dressier shoes. She was adamant, explaining that they would go great with my new slacks. She said I needed some nicer shoes for the evening. I gave her an “I give up” pout and then reached for the box and tried on the shoes. They were a little narrower than my other shoes, but the sizing was fine. I paid for the two new pairs of shoes and wore the new UGGs out of the store.

We made one last stop before heading back. We dashed into the Walgreens and bought a set of hair scrunchies and a couple of small berets. Jana said that my hair was getting so long that it needed to be controlled more. I was silent as she made the selection and paid for them at the cashier. We were finally done shopping and on our way back to the dorm.

It was nearly 5 when we got back. I told her I was going to relax in the room for a while before dinner. She told me that would be okay, but I should shower and wash my hair and meet up with her in her room by six o’clock. She planned for us to get ready together. She asked that I bring my new slacks, shoes, and the silver-grey sweater that she had bought me for my birthday the previous March. I told her I would oblige and see her later.

I returned to my room where I found Nick brushing his hair. He had already showered and was sitting at his desk stroking his hair with a new hairbrush. He was told by Rita that he needed to take care of his hair better and brushing it at least 100 times would make it look better. When I walked by him I could tell he smelled different. He must have been wearing a new cologne or more likely perfume. I liked the smell and the scent smelled fresh and slightly sweet. It was a nice smell, but I chose not to comment on it. If Nick had experienced a day anything like mine, he was probably not in a sharing mood. Nick was certainly forging ahead with the challenge. I wondered how our little moment together might have affected him.

I told him my plan to meet up with Jana in her room. He informed me that Rita would be coming over to our room around the same time to get them ready. Obviously, the girls had coordinated the evening’s plans. I decided to rest for a short while before showering. While I lay on my bed I could not stop watching Nick stroke his hair over and over. Two months back, I would never have expected to ever see that sight. He looked very relaxed doing it, and ever so often cocked his head to the side to see how his hair was flowing. His hair looked much shinier than normal.

Just before six I made my way down to Jana’s room. When I knocked, Rita opened the door and said “goodbye” to Jana. She had a bag full of stuff in her hand when she disappeared down the hall. Jana told me to make myself comfortable at her desk while she finished putting on some makeup. She was glad my hair was still damp. She mentioned that she wanted to blow dry it and give it little more shape and more body. I was somewhat apprehensive having her work on my hair and help me get ready, but I knew Nick was experiencing a similar ordeal.

She had me dress in my new slacks with my laciest lingerie. She also had me wear nylons, which until this night I had avoided. She even had to show me how to properly put them on.

When she saw how the lingerie and nylons looked on me she had a small frown on her face. She spouted, “That just will not do.”

I asked her “what’s wrong?’

“My penis was ruining the effect!”

“It doesn’t detach and despite her best efforts would have to stay.”

She then instructed me to remove the panties and nylons and lay on my back. This suggestion may be nervous but I complied. She slid a black thong like item up my leg to my thighs. She then pushed my penis back between my legs while carefully and gently tucking my testicles up into my body cavity. She then slid the thong down to hold everything in place. She then instructed me to put everything back on.

My groin area now resembled Jana’s. It felt strange walking around the room and looking at myself in the mirror. She said that she bought the gaffe off Amazon and was not sure when she was going to give it to me. She said it would provide me a little “cleaner” look. With it on I found myself walking with a shorter stride, which Jana thought looked more feminine. She then had me put on my slacks, sweater and new shoes. Maybe it was the way the heels changed my posture, but from the neck down I looked pretty feminine. If I had even small breasts, the look would be all girl. I was relieved at the challenge never included that item. I felt that at least in a dark restaurant, I could still pass for a boy.

She told me to sit down at her desk so she could work on my hair. My hair had grown quite a bit since the beginning of the semester. I was having a hard time keeping it out of my face, especially when it was windy out. I probably would have worn it in a ponytail if not for the fact that I was wearing earrings. I like having some of my hair covering my ears to avoid comments.

Jana started working on my hair with a brush and a blow dryer. She seemed to be having fun brushing my hair in every direction. After a while, she started mainly brushing my hair from underneath while using the dryer. It felt like she was pulling down on my hair as she curled the brush. She did this on my sides and in the back. This process went on for about 15 minutes. Before I had a chance to see myself, she changed my earrings to something she said were more appropriate for the evening. They were a pair of her earrings and I could tell they weighed more than the studs I was wearing before.

When she was finished, she let me walk over to the full-length mirror to see the effect. When I saw myself in the mirror my heart started racing. The person staring back at me looked almost foreign to me. She had parted my hair down the middle and gave me a giant wave that curled under all the way around my head. Whereas before, my hair had very little body, now it looked almost rounded with much more fullness. It certainly looked like I had more hair than before. Even with my hair covering my ears I could still make out the new earrings, which were dangling sterling Silver teardrops.

The combined effect of the new hairdo and the clothes that I was wearing would certainly make it hard for me to pass for male. At best, I might be considered androgynous, but more to the girl's side of the ledger. I stared at myself in the mirror while turning my body and head a few times to convince myself it was me. The clothing and hair adorned my thin frame and made me look almost attractive. The hairstyle seemed to frame my face nicely. I was amazed, how much differently my face looked with the new style. I was not wearing any makeup, but my face looked so much more delicate. I was very confused looking at myself, because I found the image appealing.

Here I was getting myself ready to go out to dinner looking nothing like myself. This would be the first time, venturing out into the real world, where the challenge would be with me with every stride. The changes were not about just feeling different, now it was about looking different as well. I was scared that I might receive some ridicule from someone who might think I was strange. Jana seemed unconcerned; she said the only thing I would have to worry about is how I would react to a complement. I had gotten dry lips from looking at myself and thinking about what was ahead. Jana gave me some Chap Stick that was cherry flavored. I spread some on my lips, only to discover that it also had a clear shimmer to it. At least it didn’t have any color. This was all a very big step and I don’t think I could’ve taken on anything more.

Jana suggested that I take the Chap Stick with, incase I got dry lips while we were out. I took the stick, but I didn’t have any place to put it. I asked Shana if she could carry it for me, but she suggested something else. She gave me a small purse so that I could put my Chap Stick, wallet, and keys inside. I didn’t like the idea of carrying a purse, but I did not have anywhere else to put my things.

Jana said it was time to go and we should walk down to pick up Nicole and Rita. Just before we left the room she gave me a small sprits of perfume. It was just a couple of drops from her Chanel, but it was very distinguishable. I always liked the Chanel on her, so she thought I might like it on myself. I prayed that I would not see any close friends while going back to my room or during the evening. I had not thought through any logical explanation so I planned to just hang close to Jana.

I unlocked my dorm room without knocking. I did not want to hang out in the hall any longer than necessary. When I walked in, Nick turned around in a somewhat startled way. He was probably on eggshells just like me. I was stunned to see my friend looking so pretty. His hair had been combed out in a way only a girl would wear it. It was parted down the middle, but it had an uneven part almost as if it had been braded down the top. He was wearing an off-white sweater that had an oval neckline. The sleeves only went down about three quarters of the length of his arms. On his right wrist were about five or six gold wire bracelets. Nick was also wearing a new pair of shoes. They were wedging in design and probably no more than about 2 inches in the heel. What stood out most about the shoes is they appeared to be patent leather. They were very shiny and had an almost pointed toe.

The two of us had endured the almost complete erasure of our masculinity. I would never have imagined that this challenge would ever have gotten to this point. Here we were going out to dinner looking so ultra feminine. Depending on how we walked and talked we would probably most certainly be mistaken for girls. I was not sure whether would be better to be mistaken for a girl and blend in or to try and act like my old self.

We grabbed a cab and headed to downtown. When we arrived at the restaurant the maá®tre d' asked, "Ladies would you like a booth or a table?" Rita asked for a table, she said later, that it was because it would be better for showing off our new looks. The girls were certainly enjoying themselves and giving us as many pointers on how to act and to carry ourselves. Jana even explained how we should look at men. If we wanted to flirt, we should look at them one way and if we were just checking them out, we should look at them a different way. I didn't understand why she was explaining that to us, but she said it was part of being a girl. After she said that, I was sure some guys at the bar were checking us all out. As a guy, I never remember anyone ever checking me out. Now on my first evening out dressed primarily as a girl, I was getting the once over.

Dinner was good considering the bizarre activities we were participating in. Most of the conversation was between the girls and us and not between Nick and myself. We probably looked at each other 1000 times or more, but we rarely engaged in conversation. I really wanted to know how he felt, but this just wasn't the right place to inquire. We both really looked the part and listened very intently when the girls gave us advice. Early on in the challenge, we were more resistant to their comments, but now it seemed like a game plan for getting through the experience.

We finished up dinner and the girls asked us if we were ready for dancing. I could not imagine being in a dance club looking like we did. Jana said we would have a great time and we would not be out late. The dance club was only two blocks away so we chose to walk there. We ended up taking a longer route to the club, because the girls wanted to work on the way we moved. They made us walk in a much more ladylike way with 1 foot in front of the other and a slight sway of the hips. They reminded us how we should hold our arms with either our wrists slightly bent or our thumbs pointing slightly outward. They had us keep our posture upright and our hips slightly forward. After finally getting the hang of it we headed into the club.

I told Jana that I definitely needed a drink, preferably something strong. She went up to the bar and ordered four cosmopolitans. So here I was looking so girlish, sipping on a cosmopolitan, on the edge of the dance floor. Jana wasted no time pulling me out onto the dance floor. Even dancing in girl style cloths felt different. I tried to mimic the way Jana danced and I found myself copying other girls out on the dance floor. It really wasn't that hard, but it was a new learning experience. We danced a couple of songs and I saw Rita and Nick out there as well. Earlier in the evening I built up a lot of nervous tension, but being out on the dance floor seemed to make me feel more relieved. Something about being on the dance floor let’s you loosen up a bit.

We took a little break from dancing and made our way back to our bar stools. I think it was the first time in a while that I laughed. I was finally enjoying the evening and not focused on the circumstances. It was nice having a drink, listening to some good music and just letting loose a little. Rita and Nick worked their way back to us and also were clearly enjoying the club. After a while we did some more dancing and I even went dancing with Nick. That seemed pretty harmless, since there is really nothing that odd about two girls dancing together. Nick and I returned to our drinks and waited for the girls to finish up their dancing.

Nick and I were just hanging out sipping our drinks when two guys approached us. They asked us our names and I nearly choked on my response. Before answering I looked around the room for Jana and Rita. In a faint voice, I said my name was Michelle and this was my friend Nicole. The guys tried to be charming, but we kept looking around for help. They asked us to dance and since we had obviously just been dancing, we really didn't know how to tell them no. So there we were out on the dance floor with two other guys. I was grateful that the song had a pretty good beat so that we would not have to dance together too closely. It felt so strange to be the object of some other man's desires. In a way it was a complement, but it still felt very awkward.

I saw the girls returned to our area, so as soon as the song ended we told the guys that we had to get back to our friends. We told them that we had promised to hang together and that we would be leaving shortly. We thanked them for the dance and scurried back to our girlfriends. Both girls were smiling from ear to ear. Jana asked me, “How does it feel to have your first conquest?”

I gave her a dirty look and said “what were we supposed to do?’

Rita asked "do you two want to invite them over to the table?"

"I think it's time to get the check, I've had enough fun for one evening" Said Nick.

The girls didn't push it and agreed it would be a good time to go. They knew that there was only so much we could absorb in one day. The challenge was meant to be a gradual and subtle adjustments and if they push too hard, it would not be any fun for anyone. This seemed to be a good place to end the fun for one day. We quickly went back to the dorm. I ended up spending the night with Jana, while our two friends slept together back in Nick’s and my room.

That evening clearly marked a shift from some playful small challenges to a desire by the girls to see how truly feminine they could push us. It wasn't enough for us to have some girly characteristics, but they really wanted us to experience life on the other side of the fence. I kept thinking it was all part of the game and things would get back to normal when it was over.

I do not think Jana ever really treated me much like a true boyfriend again. That is, she still treated me with love and caring, but the shift was to that of a girlfriend. We still were lovers, but the sex was more woman-to woman than man-to-woman. We had great passion together, but the style and nature of the activities certainly had shifted.

On Sunday morning Jana had me put my hair in a ponytail. A lot of guys wore ponytails, but mine was put up higher on the back of my head and with a black scrunchy. For effect, Jana also pulled out a few strands of my hair in front to hang down on both sides of my head. When she was done she stepped back, smiled, and said I looked ‘cute’. I exhaled a little extra after her remark.

I wore my skinny jeans and one of Jana’s blue T-shirts over my Vicky's underwear and I made my way back to my room. I needed my backpack and books to do some studying. Rita had left the room before I got there and Nick was just getting dressed.

I noticed when Nick greeted me that he had a little remnant of lipstick on. I would normally have assumed it was Rita’s, but it was not the same shade she had worn the previous evening. Before we left the room I held my finger up to the corner of my mouth, so Nick would know that he had something on his lips. He glanced at the mirror and quickly wiped his mouth clean with a tissue. He said, “thanks.”

We skipped the cafeteria and stopped at Starbucks on the way to study. Nick complemented me on my hair, which caught me by surprise. Did he really think it looked good, or was he just trying to make me feel better? Either way, it made me more aware of how I looked. The turnabout evening was over, but we were still both looking and acting different. Even the way we walked had changed. Our sway may not have been as pronounced as the previous night, but our gate was much clearly more ladylike.

Nick and I made our way to the union building. There was a room in the back that had a few tables and a bunch of vending machines. We thought this would be a good place to study, because it was not our regular study place. With the way we look, we really didn't want to run into people that we were familiar with. In the vending room we would just be a couple of students that probably nobody knew.

Nick looked so much more demure than the friend I grew up with. My old friend was an outgoing and somewhat aggressive lad. The friend sitting across from me at the table seemed almost shy and more introverted. His hair was beautifully brushed and on one side pushed back behind his ear. His gold studded earring almost glistened as I scanned his face. He still had a small scent of Rita’s Chanel perfume emanating from his body. He was wearing one of Rita’s white turtleneck blouses that had a small zipper in the back at the top. If I did not already know his true sex I might have been confused.

We talked about classes and the school football team, and even world events. After chatting for a while we started talking about girls. It wasn't your typical guy talk about girls though. Instead of talking about how hot certain girls were or babes we would love to get into the sack with, it was more about how they dressed or looked. Nick commented about a girl two tables over and her hair. She had her hair perfectly parted with a braided section in the back. Parts of each side were pulled up over her head and clasped with some sort of butterfly clasp. Parts of her hair hung down to the sides. Nick seemed fascinated by her hair. He asked me how long I thought it took her to put her hair up like that each day. I had no idea and never really had given it any thought.

I found myself making comments about what some of the girls in the vending room were wearing. It was as if we were critiquing the girls in the room. We hung out there for about three or four hours and finished up the work we needed for Monday. There was a guy sitting alone at the table near the door who kept looking at me. I didn't know who he was so I assume he didn't know who I was or at least hoped he didn't. One time I looked over in his direction and he gave me a small smile. I was a little freaked out by it. I wondered whether he was interested in me or just thought I looked a little bizarre. I felt a little like I did dancing at the club with those strange men. I was sure he was going to come over and introduced himself so I asked Nick if we could leave.

We only had a few days left of school before we would be heading home for Thanksgiving. I would be leaving after school on Friday and Nick was still planning on holding out till Monday. The events of the weekend made me think a lot about how Thanksgiving might go. Some of my changes would not be easily masked. The girls we're going to give us one last challenge before we left. It would be tough enough getting through the holiday without some new challenge to overcome. Much like the previous week I spent a lot of time with Jana and not so much with Nick. She seems so intent on perfecting my mannerisms and posture. On Tuesday she even started working on my voice inflection. She had me slowing down my speech and trying to adjust my tone and pitch. I was spending so much time with her that I rarely had time to act like my old self. It was almost like a crash course before heading home.

Friday arrived and we were all excited about having a week off from school. We all had morning classes that day, but would be free for the whole afternoon. It was decided that we would all go out to lunch for one last meal together. At lunch, we would learn of our last challenge prior to break. The girls had been so careful with our diet all semester long that if nothing else our families would be commenting on how much weight we had lost. For our last meal we went to a contemporary restaurant that had a great salad bar. We had managed to develop appetites that were better suited for girls.

We noticed that when we went to lunch the girls did not have any backpacks or packages with them. Only Jana had a purse and it wasn’t really that large. We figured whatever the challenge might be it would hopefully be small. After eating I prodded them to give us the news. The girls told us we would be grateful for this newest challenge, as there would be nothing obvious about it. They even said it would be our easiest challenge so far. They picked this weekend for us, since we would be going home and they wanted it to be easy for us this week. We were getting very curious and impatient.

The girls opened up Jana’s purse and handed each of us a flat container and said “open wide.” We took the containers and opened them. Inside, laid out in row were 28 pink pills.

“What are these?” I asked

“They are for your complexion and to help slow down the growth of your body hair.” Jana answered

“In a way they are vitamins made for women. Rita and I, take one every day and think the two of you ought to also. They will make all the other things you have been doing a little easier.”

Nick asked, “What’s in them?”

The girls did not want to lie to us, so they came right out and told us what they were.

I was stunned, “You want us to take birth control pills?”

We were told that they would help us look a little softer and slow down the growth of our body hair. The other effects would not be that great unless we stayed on the pills indefinitely.

Rita interjected, “The pills may even make us feel more comfortable in our new clothes. After a while, some of them may even fit better.”

I was not sure I liked the sound of that, but we only had a few weeks to go before winter break anyway.

Nick and I excused ourselves to go to the bathroom. It was a trick the girls often pulled on us. We needed a moment to discuss this newest challenge without the girls present. Fortunately we were the only two guys in the bathroom so we had some privacy to chat. Neither of us liked the thought of taking something that might lead to some physical changes as a result. We were not into drugs so putting something foreign into our bodies was not something that we would normally want to do. We were happy that the week’s challenge was not something that would be noticeable (at least now), so it would be an easy thing to do over the break. If we chose not to do this and asked for something else, maybe they would pick something that would be more difficult for us to hide when we went home. It was not an easy choice and something we were not completely comfortable with. We figured, if we could just make it through to Christmas the pills could not have that much of an impact on us.

When we returned to the table, we reluctantly agreed to take the pills. The girls told us to take the pill at the same time every day. They suggested it would be a good idea to take it in the morning in case we forgot. They told us to open wide and take our first pill now. We did and put the container into our pockets. What have we done… was all I could think.