Boy Wakes Up To Find He’s Turning Into A Girl 💅 (Crossdressing Stories) PART 1

hey there you're looking kind of cute please consider subscribing and check out our patreon for more enjoy the video Jean knew he would lose everything he couldn't pass the math final no matter how much he crammed or prayed boxwood Academy had withstood the anxiety of teens for over 100 years situated on a hill overlooking a river town and taught both the sons of wealthy people and the smartest boys as long as they were boys if you were a smart young woman or the wealthy daughter of a rich family you could go to boxwood School in

the valley next door boxwood took a Libertarian approach but had a conservative way of thinking he emphasized Independence and being yourself the young men were not told what to do only what was expected of them if they were rude to other people their peers asked them to leave Jean did well in school and came from a wealthy family but he couldn't get trigonometry out of his head he fell into the Trap of people with quick intelligence and never learned how to master something that didn't come naturally to him so he didn't study at all this

session even though 80 percent of his grade was on the final and he had failed the first two tests he still had one more hour until before he could go to bed the test was set for 10 in the morning he looked over at the people sleeping in his room Roman was softly snoring and when he moved his bed springs squeaked Norman was completely out he worked so hard at sports that he always slept like he had just been turned off this was their third year in the same triple room they were one of the

few groups that had been together since they were freshmen they were different enough that they didn't compete with each other Jean fell asleep in his chair at last in that strange way that the mind of a teen Works Gene's head was full of thoughts about the universe life and death and the rest of his life he would not even try to think about what would happen to him if he failed this test now people think that the Universe might just be a switchboard for human consciousness where you plug into one reality for a while turn

it off and then plug into another every time you lose all your memories and have to start over even if you're only there for a second it will feel like you've been there forever what a dream huh Gene knew that Roman was shaking him awake when he woke up he just didn't want Roman to feel good about an easy win Gene get up the test is today come on it's time to start making breakfast Roman thought that everyone would react to the idea of breakfast the same way he did which was to get up and

get some food no matter how much sleep they had had Gene didn't like breakfast until it was time for lunch except that he liked coffee more and more these days in the common area Norman was doing stretching exercises his six foot three inch frame was strong but not too strong if Norman could just choose one sport he was probably going to win an Olympic gold medal he loved all of them Norman stood out because he was the only one who wasn't a jock he played Sports against himself as a standard and while he could work

as part of a team when he had to he wasn't a team player in other ways he liked and stuck with his few old friends one good thing about boxwood was that the rooms were great each boy had his own room with a bathroom and the common area was big there was a TV but it only worked after 8 pm and it only got two channels after that yes they had a DVD player and the different computers they shared gave them access to almost any kind of entertainment but the boxwood curriculum took up a lot

of their time during class only those who didn't pass watched much TV boxwood made up for the busy schedule by only running sessions for six weeks then taking three weeks off during class time the students did two things study and work out sleeping and eating were luxuries that they didn't have to do Roman pulled Jean out of his chair and put him in a position that was close to standing up Roman was a bit fat in fact Roman was big not too fat though he was big enough for everyone to notice but he was a

loyal friend who would cover your back lie to your parents and do all the other things the guys needed he was also a kid who got a scholarship because of his skills and grades Jean fell into the shower and stood under the running water trying to get some rest that way for about 20 seconds it worked he was the most normal looking of the three he was 5 feet 11 inches tall and weighed 170 pounds he had short brown hair and no scars tattoos body piercings or glass eyes he also had the standard number of

arms legs fingers and toes he wasn't pretty ugly or handsome his mother called him cute but jean didn't remember many people agreeing with her he liked sports but he wasn't very good at them he liked girls but he didn't get them very often he liked school and he always did well enough without trying too hard up until now at least boxwood didn't think that people should wear uniforms instead they had an unspoken dress code that hadn't changed much in the last 10 years it seemed to change about every 7 to 10 years the current one

was made up of casual pants dress shirts and sneakers which wasn't too different from what lawyers or Bankers wear when they're not at work Gene put on his clothes even though he was still tired from not getting enough sleep he couldn't get his shirt buttons done right it was like he had no reflexes at all Gene for the love of God wake up allow me to help you Norman said as he put Jean's shirt back together the three of them went down to the dining hall for breakfast this was a central area that connected the

four dorms in the middle as they went by in line Mrs Fredericks who was in charge of the boys was there to greet them Jean was always interested in where she came from people thought she was either a retired hired Hitman or a professional dancer or she could have been a librarian no one had ever seen Mr Fredericks but word got around that he was either overseas or passed away because she sometimes referred to him as the colonel even though she was older she still looked great Jean thought she might be like 40 or something

she wore a skirted suit with a white blouse which was her standard uniform as headmistress Jean are you ready to learn about trigonometry today ma'am I hope so it's not simple Jean replied Mrs Fredericks always seemed honest so she deserved an honest answer Jean best of luck she looked at the boy in front of her the three people who shared a room sat in a corner to eat let me help Gene we have about 30 minutes to go over what we've learned Roman proposed I know that Roman is smart but 30 minutes I need a

whole day look at it this way Gene I'm sure I can help you answer at least one question correctly more than you would if we didn't do it Roman told us Roman thinks but I'm going to take a nap until the test Gene didn't go to his first class and went back to his room he had about an hour to rest before the test and he couldn't decide if he should study or go to sleep sleep one but everything went wrong when he figured out what was wrong when Jean tried to take off his shirt

he found that the buttons were on the wrong side the side Woman clothes normally have why is this happening he spoke out loud he went to his closet and looked at his other shirts all of them were done from left to right Norms were too and Roman Gene knew about blouses for women when he was home alone he had borrowed clothes from his mother more than once dressing up in women's clothes had become a part of his dreams but he rarely did it in real life he was very careful because he was so afraid no

one knew his secret and so far he hasn't felt the need to do it at school so now Jean had the first strange thing it would not be the last time when he saw what time it was he knew he had to get to the test he ran as fast as he could across the campus to get to the exam room he didn't understand the first question I didn't think of anything the next one was just as bad 90 minutes had never felt so long to Jean he walked back to his room in a complete

days after the test he was surrounded by a magnetic field of defeat he managed to find his bed fell into it and let sleep take him away Jean knew Roman was shaking him awake when he did Gene get up the test is today come on it's time to start making breakfast Roman told us he stood up straight what do you mean the final was yesterday calm down Gene today is the last day you must have gone to sleep last night while studying Roman stood back up he walked into the room Jean looked at them and

closed his eyes they wore dress shirts and casual pants and were ready for breakfast it was just that each of them was wearing long earrings with jewels that hung down then he saw the necklaces rings and bracelets he also noticed that the buttons on the shirt went from left to right what are those earrings for Jean asked both of them at the same time they belonged to my dad this year for Christmas he gave them to me Gene you knew that because you had borrowed them twice Norman said Gene you don't need hours you have

a Tiffany store in your case Roman gave a grin Jean stood up and took a shower his watch which had been a big chronometer but was now a thin gold case with diamonds told him it was the day of the test and he did have a large jewelry case in his bathroom it was on a vanity he saw gold posts in his ears when he looked in the mirror Jean started shaking he stood there in a towel which was still wet as he shook drops of water fell from his body Gene Move Along make sure

to bring your lucky bracelets Roman put his hand up he chose a shirt and pants and dressed himself sitting at his vanity he combed his hair and chose his jewelry out of instinct or habit he took out his posts earrings and put in some Emerald Bangles and a necklace that went with them he grabbed a handful of worn out bracelets that had been broken in a few places his good luck charms he saw that his dress shirts only had three-quarters sleeves Jean's mind was going very fast while this was going on he knew this was

wrong and not how things should be he had also watched enough science fiction shows especially that old series from the 1950s to know that he should keep his mouth shut and act like he didn't know what was going on people who didn't follow along when they were suddenly somewhere else always got in trouble in the mirror he looked at himself he thought it was funny and normal they went to eat breakfast Gene are you ready to learn about trigonometry today Mrs Fredericks asked dressed like Jean always remembered her to be ma'am I hope so it's

not simple Jean replied Jean best of luck she looked at the boy in front of her the three people who shared a room sat in a corner to eat everyone in the room including the boys was wearing a lot of jewelry Gene I'll help you with your math we have about 30 minutes to go over what we've learned Roman proposed I know that Roman is smart but 30 minutes I need a whole day look at it this way Gene I'm sure I can help you answer at least one question correctly more than you would if

we didn't do it Roman told us Roman thanks but I'm going to take a nap until the test Jean returned to his room he looked at Roman and Norman's rooms and found that the only thing that was different was their jewelry cases he also noticed that Norman's swimsuit calendar had not changed and that the girls were just as they should be when he saw what time it was he knew he had to get to the test he ran as fast as he could across the campus to get to the exam room he didn't understand the

first question I didn't think of anything the next one was just as bad 90 minutes had never felt so long to Jean he walked back to his room in a complete days after the test he was surrounded by a magnetic field of defeat he managed to find his bed fell into it and let sleep take him away Jean knew that Roman was shaking him awake when he woke up Gene get up the test is today come on it's time to start making breakfast Roman told us Roman was standing there with a girdle up to his

waist and black nylons today or yesterday or whenever this was his earrings were big Hoops aside from that everything else seemed fine Jean you asked me to shave your back today but you haven't even showered or shaved your legs and armpits yet Norman walked in wearing a pair of nylons with garter belts attached to them over a pair of satin pants Jean noticed that he was almost bald which made him look very different from the Norman he knew with his curly black hair on his chest and back Norman looked like he was part bear or

sheep Gene hurry up we only have 20 minutes to eat before they won't let us Jean jumped into the shower and washed his hair and body in a hurry he noticed the strange shaving cream and razor with a curved handle when he picked it up his legs were shaved by their own bodies as he went back to his room Jean thought about what to wear the clothes in his drawer had changed he now had three drawers for starters as he looked for something to wear he grabbed a bunch of satiny garter belts and nylons in

one drawer he found a variety of what his mother called Foundation garments such as Roman style girdles waist cinchers and things that looked like old-fashioned corsets but were made of modern materials Jean decided to go without figure support today because he didn't think he was fat not skinny and chiseled like Norm but also not at all like Roman he picked up a shirt and saw that many of them were sleeveless and had necklines there was almost nothing they could do he thought well at least it wouldn't be too hot outside after fighting with the garter

belt over the undies he was fumbling with a pair of sheer black nylons he thought that if Roman was wearing them he could probably get away with how they looked the clothes reminded him of the few times he had actually tried to be a woman they fit perfectly and felt a lot like the pants he wore back then so Jean went out wearing a sleeveless top over casual pants and necklaces hoop ear earrings and bracelets that clanked the pants didn't seem to have changed much maybe the fabric was a bit softer he found some shoes

and decided to wear black loafers instead of his usual sneakers because they looked better with the nylons Jean are you ready to learn about trigonometry today Mrs Fredericks asked ma'am I hope so it's not simple Jean replied Jean best of luck she looked at the boy in front of her the three people who shared a room sat in a corner to eat Jean's clothes went well with everyone else's Roman looked much better when his belly was held in and Jean could see that Roman wasn't the only one who looked slimmer Jean I'll help you with

your math we have about 30 minutes to go over what we've learned Roman proposed I know that Roman is smart but 30 minutes I need a whole day look at it this way Jean I'm sure I can help you answer at least one question correctly more than you would if we didn't do it Roman told us Roman thanks but I'm going to take a nap until the test Jean returned to his room he looked in Romans and Norman's rooms and found that their closets had been changed just like his when he saw what time it

was he knew he had to get to the test he ran as fast as he could across the campus to get to the exam room he didn't understand the first question I didn't think of anything the next one was just as bad 90 minutes had never felt so long to Jean he walked back to his room in a complete days after the test he was surrounded by a magnetic field of defeat he managed to find his bed fell into it and let sleep take him away Jean knew Roman was shaking him awake when he woke

up get up the test is today come on it's time to start making breakfast Roman told us Roman was standing there in a girdle that went up to his waist and was tied to a pair of sheer brown nylons today or yesterday or whenever this was his ear studs were big pieces of jewelry his hair which used to be short had grown out and was now pinned up on the back of his head Jean didn't know how long it had been aside from that everything else seemed fine Norman walked in wearing a pair of black

nylons with garter belts attached to them over his satin pants today he went with Hoops Jean noticed that he still didn't have any hair on his torso but he was more interested in the blonde wig on his head Geno hurry up we only have 20 minutes to eat before they won't let us he said Norman Jean jumped into the shower and washed his hair and body in a hurry he didn't think about what he was doing and just used shampoos and conditioners that seemed natural to him he had a wide range of choices he picked

up the razor and his legs started shaving themselves he could shave his face and underarms because the mirror didn't fog up Roman wore a red-haired version of Norman's wig which was pinned up dry your hair and get dressed for goodness sake after what seemed like an eternity he just let his hands do the work of putting his hair up and then he turned to his 20 wigs which were all on forms his bathroom and dressing room seemed to have gotten three times bigger he saw that some of the wigs were in clear packages with tickets

that said Fred's wig service we pick up and drop off jean thought about what to wear aside from the pants not much has changed they didn't have any pockets and fit closer around his backside and thighs Jean saw a bunch of purses one of them seemed to have his wallet comb keys and what he thought was an atomizer for cologne he smelled it and it smelled like his aftershave but stronger he chose emeralds once more he finally figured out where to put the garter belt and chose a pair of sheer hose with a diamond pattern

many of his shoes were now sandals with open toes so he chose the simplest pair he could find so Jean went into the common room where Roman made fun of him get up you fool two years ago we finally got those old stuffy guys to change the dress code so we could wear wigs now you're trying to start a counter Revolution do you want to be in charge of how your hair looks we had no other choice as you know Roman went on still laughing Norman gave a grin sorry guys I'm not awake yet Jean

went back to his room to rest Jean chose a page boy wig that was black and put it on his head he didn't think about it but his hands reached for bobby pins he let them do what they wanted he was learning to calm down and let his body and reflexes take care of things the three people on board went to eat breakfast Jean are you ready to learn about trigonometry today Mrs Fredericks asked ma'am I hope so it's not simple Jean replied Jean best of luck she looked at the boy in front of her

the three people who shared a room sat in a corner to eat Jean's clothes went well with everyone else's the wigs added a lot of color to the room with their many different shades some of the boys chose blues and purples Jean I'll help you with your math we have about 30 minutes to go over what we've learned Roman proposed I know that Roman is smart but 30 minutes I need a whole day look at it this way Gene I'm sure I can help you answer at least one question correctly more than you would if

we didn't do it Roman told us thanks Roman but I need you to pay attention to something Gene tried to explain what was going on like how the world was changing every day but the same things kept happening Roman was not only smart but he also thought in a unique way he also knew the truth when Jean told it Norman was also worried but he did not say anything so Gene you want us to believe that you keep waking up and living the same day over and over again and that the only thing that changes

is what people wear and you mess up your final and then pass out so you can start over now I'd say that you just woke up from some kind of anxiety attack and that everything will be fine tomorrow but you seem worried so here's what I can do I'm going to write down some words that mean something to me but not to anyone else remember them and then give me the paper back if the next time you wake up and we all turned girly then explain this to me again and tell me the phrase but

only say it to me so that no one else can hear now forget about this calm down and go do your best on the final I told you I'd help you with your math homework thanks for watching check out patreon if you want to have early access to the other parts if not it will be online in a couple of days