When Beth Helped Part 1 by occwe
Summary:

Lucy convinces James to dress up for the first time.


Categories: Fiction Characters: None
Age Group: Teenager 13-18
Categories: Femdom/Authoritarian
Genre: Fantasy
Keywords: School Girl
Story Universe: None
Challenges: None
Series: None
Chapters: 5 Completed: Yes Word count: 15794 Read: 77824 Published: 12 Jan 2012 Updated: 01 Mar 2013

1. Part 1. Day 1. When Beth Helped by occwe

2. Chapter 2 by occwe

3. Chapter 3 by occwe

4. Chapter 4 by occwe

5. Chapter 5 by occwe

Part 1. Day 1. When Beth Helped by occwe

It was a couple of years ago. Well almost a couple of years ago. But who cares about exactly when. I was 16, just, and my exams for GCSEs were over. My time at secondary school was over, in September I was moving to the school where my sister had completed her A levels. I was looking forward to a long summer holiday, chilling, playing on the playstation, watching DVDs and not doing much at all. My name is James. And this is what happened when my sister decided she wanted to write an essay to submit with her uni application. She was just about to embark on a gap year before studying psychology at university, but she had not yet applied, and she wanted to stand out from the crowd.

She knew about me dressing up for the likes of halloween for fun etc. and I had worn my girlfriends clothes on the last day of school, but that was it. I never took dressing up in girls clothes seriously, and I never wanted people to believe that I was a girl. Her idea was simple, place me in a school as a girl, a year younger than me for the last few weeks of school, get the school involved in a social experiment and see how things panned out. She approached the school before she approached me, got them on board.

It was a Thursday. I had just got home after spending a few days at the girlfriends house. I got home and went to my room, there were a few Marks & Spencer bags on my bed, but I just thought that perhaps either Mum has bought some things that she wanted to keep out of view of my Dad, or my sister had bought some stuff she wanted to keep hidden from my parents. I just shouted to Lucy to come and get rid of the bags, if they were Mum’s she would just shout that. But she didn’t respond. She was home. I think she was in her bedroom, the room right next door to mine.

Anyway, I turned my TV on and just watched TV for an hour or so, she didn’t come and get the bags so I began to think that perhaps they were Mum’s. Curiosity got the better of me after a while, so I opened up the smallest bag and saw a couple of pairs of black trousers and a couple of packs of white shirts. I figured they were my sisters, and not my Mum’s because the clothing was just too small to be my Mum’s. At the time I had no idea how sizing worked for women, I had never been involved with it, I’d only heard about the size 0 model thing and alike from the press. But lets just put it this way, both myself and Lucy took after our Dad’s small frame, we weren’t particularly a tall family either, anyway, I digress.

I left the bags there and went out to meet up with some mates. After hanging out for a couple of hours, kicking a football around, I headed home. Both my parents were away at a funeral that day, they wouldn’t get back until late, so it was up to me to feed myself. I got back home and Lucy was in the kitchen, cooking far too much food for just her. She explained how she was going to cook for both of us. I thought that was weird at the time, but now it makes perfect sense. She wanted me on her side, and she knew that through my stomach would be the best way to do it.

Dinner was delicious, far better than I was expecting. I helped Lucy clean up and went back to my room. Expecting the shopping that was in my room to be gone, I turned on the playstation and played some Call of Duty. I had barely started the first game when Lucy came into my room and stood in front of the tele.

“I have something I want your help with” she said, her hands on her hips. She looked like a strong willed business woman stood there, dominant, powerful. I’d never seen her like this, perhaps it was the fact she wasn’t wearing jeans and a t-shirt like normal, but the suit trousers and shirt really made her look powerful. “I want to write an essay to send with my uni apps, I want it to be a social experiment on peoples perceptions and believes. I want to put a goat amongst sheep and make the flock believe the goat is in fact a sheep”.

“Are you crazy?” I shouted, “What the bloody hell are you talking about?”

She grabbed the bag that I hadn’t looked in, grabbed something out of it and chucked it at me. “Put it on” she demanded. No emotion in her eye, no joy or anything. A command. Do it. Get on with it.

“What the hell? It’s a skirt. What do you want me to put a skirt on for?” I questioned, throwing it back at her.

She took a different angle with everything now. She sat on the bed, the skirt in her left hand, the bag in her right. “Look, James, I want to stand out from the crowd” she explained, “I want to hand in an essay that makes me seem like the best student the uni could possibly have.”

“You want me to wear a skirt, and that’s going to get a uni thinking that you are the best of the best?” I said, my voice still raised, I sounded girly looking back at it, I was hardly the manliest of men, remember I was only 16! But yea, I think she took a liking to the fact that I had a high pitched voice because she smiled. I cleared my throat and continued in a deeper, forced tone, “I don’t see how me wearing girls clothes, and a school uniform at that, is going to help you write an essay.”

“It’s simple. I’m going to put you into a school. As a girl”, she smiled.

“ARE YOU INSANE?” I shouted, again, quite a high pitched voice. I just looked at her, dumb founded.

“No. It’s simple. I transform you into a girl, a believable one. You start school 3 weeks before the end of term, so in two weeks time, I record everything on this”, she got out a dictaphone with what looked like a single headphone. “And I write an essay on how your personality changes around a different social group in those 3 weeks and how people react to you. You will look, act, walk and talk like any normal 15 year old girl.”

“You are insane. There is no way that I would pass, even if I did agree” I replied. There was a familiar knock on the front door. I went and answered it, leaving Lucy in my room. Probably the biggest mistake of the day. Things may have turned out differently.

I wasn’t surprised when I saw Beth at the door, she always knocked a door in the same way. Sorry, Beth was my girlfriend at the time. “What is it you wanted to talk about?” she asked.

“I have no idea what you are talking about.” I questioned, and then Lucy ran down the stairs.

“Hey Beth, sorry, I sent the text from James’ phone. I want your opinion on something, and if you agree then I could really do with your help”, Lucy explained.

I went to my room, hoping that Lucy would have just given up, but no. Laid out on my bed was a white shirt, ¾ length sleeves, a black skirt, it was a fashionable drop waist pleated skirt, a pack of tights, a pair of black shoes, a black jumper with the secondary school in the neighbouring town’s logo and a tie, also belonging to the “other” secondary school.

“LUCY” I shouted. “I SAID NO”.

Lucy and Beth were already in my doorway as I turned around shouting. I didn’t have a clue what to do. They both looked at me. “Come on babe, we know you can do it, just a little bit of effort and you’d look great. I’m right behind you, besides it’s to help Lucy get into a good uni. Surely you want to get rid of her sooner than later” Beth exclaimed. For some reason it made perfect sense, the better the uni Lucy went the better a job she would get, the better a chance at her not coming home as often would be.

“I’ll put the uniform on.” I said.

“Good! Thank you! I have a wig for you too, and I have bought some light makeup to start with too.” Lucy said as she left the room. I thought I would be able to get out of the experiment she had planned if I just simply dressed up.

Beth got everything out of the bags, there was a black bra, black lace knickers and other things. Turns out two of those “other things” were breast forms. It appeared that Lucy had planned this too well on a whim that the school would accept a boy in drag as a student, and she must have been convinced that I would agree. Oh how wrong she was.

“Take your top off J” said Beth, with a smile on her face.

I obliged, who wouldn’t take their top off if their pretty girlfriend told them too? She grabbed the bra and asked me to turn around. She put bra on and did it up. I turned around and just looked at her. It was uncomfortable and felt really weird, it was hanging off my chest. What the hell was the point in wearing a bra? I didn’t have boobs! That’s when she grabbed the rubbery “things” and put one in each cup of the bra, they were cold on my skin but the bra felt less uncomfortable now. Not that it was comfortable, but you get my point.
She chucked me the shirt and said “You can handle a shirt right?”, smiling. Could I heck! The buttons were the wrong way around, but the hell was that all about? A minute or so later I had the shirt buttoned up, what was really weird was how well it fit my body, it hugged my waist and arms, it was tight against my “breasts” but not to a point where the shirt looked too small. It was weird how well Lucy had managed to get everything fitting perfectly so far.

“Got that much right then” said Lucy as she walked back into my room with a vanity bag on her hip, it was a pretty big one, and a bag of a few other things in, I could see a wig in the top of the bag. She smiled and sat on the chair next to my desk. “Don’t worry about putting the knickers on, you will need to get used to hiding a bulge 4 out of 5 school days so you have a couple of weeks to get used to them. Put the tights and skirt on.”

I took my jeans and socks off. I’d worn a skirt before, so the feeling was going to be the same, only the last time I wore a skirt I ended up having sex with my girlfriend whilst wearing it, but the last time I didn’t have the chest of a 15 year old girl! I put a hole in the first pair of tights I got my hands on so Beth helped me put them on, her touching my leg excited me but I couldn’t tell if it was the feeling of tights or the feeling of her gentle touch on my skin.

I didn’t want to get my growing bulge seen by my sister so I put the skirt on pretty quick and sat back down on the bed. “There she is” said Lucy, with a smile on her face. “You know you have great legs! And quite a cute figure. Now, let’s get a little makeup on you and this wig and see how passable you are. If you still look like a boy then I was wrong, I’ll take the clothes back and we can forget this ever happened”

I was jumping for joy inside, I knew then that I would not be doing her stupid experiment.

We moved to Lucy’s room, she brought everything with her, she wanted me to see the transformation take place rather than just do the makeup then put a small mirror in front of me. She started off with foundation, it didn’t even look like there was anything on my face to start with. I didn’t know if that was a good thing or a bad thing. She put a little bit of blusher on so now my cheeks looked a little redder than before. No major difference really, clearer skin and redder cheeks, big deal. Then came the eye liner and mascara. Now I looked weird. My eyes looked bigger, bluer than before. And finally Beth put some lip gloss on my lips.

“I didn’t think they allowed this makeup at school?” I asked.

“They don’t. But if you look like a girl now then we can dumb the makeup down a little and still achieve it, besides, the only thing they will not allow is the lip gloss, every girl wears this amount of makeup to school now anyway.” Beth said, clearly she was enjoying the fact that I was just powerless.

The wig was next, it was blonde, fairly long, but not overly. I asked if it was real hair, it was, Lucy had bought it for herself a couple of years back for New Years Eve, I remember it quite well. My new blonde hair was perfectly straight. But Lucy wanted to make me “cute”, as she called it. First she put it in a low pony tail, then a high pony tail. Neither looked anything special. Then she went for standard cliche schoolgirl hair, pigtails. I hardly recognised myself looking back at in the mirror.

In fact, there was a pretty girl sat where I was sat. She had blonde hair, big blue eyes, and looked really cute. I guess that is when my opinion of the whole thing started to change.

“Get used to the clothes, let me know if you still don’t want to do it tomorrow. Mum called when you were out, her and Dad are staying over at a Travelodge for the night so won’t be back until tomorrow evening now. So you have no fear of them ‘catching’ you like this. Go have some fun, watch tele, walk about in the flats. If you want put the knickers on, but you will need to put the gaff on - it’s the ‘weird’ looking thong type thing, it’ll hide your bits. If you could try the trousers on, they should be tight on your ass and crotch but not overly tight anywhere else. That is if I have bought the right size for you.” Lucy said, with a smile on her face.

I stood up and she sprayed me with perfume. Now not only did I look like a 15 year old girl, I now smelt like one. Beth appeared to be enjoying this more than I was.

Beth and I went back to my room. “You have a wiggle in your walk” Beth said, slightly giggling as I walked in front of her.

“What?” I asked.

“You wiggle like a girl when you walk. Your skirt moves just like it would if I was wearing it. Only I naturally walk like that. I’ve never noticed you walk like that before. It’s cute” she said, smiling, she put her hands on my waist and kissed my lip gloss coated lips lightly. She playfully pushed me back, turned me around, slapped my ass and walked into my room in front of me, playfully turning around with a grin on her face.

It felt weird. I stood there. In my doorway, I looked down the hallway at the mirror at the end. All I saw looking back as a cute blonde schoolgirl. That was when I started to change my mind about this even more.

“James, are you going to stand there all night checking yourself out?” Beth shouted from my room. I didn’t respond to start with, I was mesmerised by my reflection. “JAMES!” She shouted.

I jumped and walked straight into my room. She was sat on my bed. Her hands in her lap. With a smile on her face. “I can’t get over how cute you are, what shall we do?” she asked.

I shrugged and sat next to her, I hadn’t felt nervous around Beth since I can remember, I have always felt comfortable in her presence, but now I was shaking when she put her hand on my knee. “Shall I dress up too? We could role play?” she suggested. I had never done role play before. But I agreed, I figured the night couldn’t get much more weird.

Beth grabbed her bag and vanished. She came back about 5 minutes later, she was wearing similar to me, only her skirt wasn’t pleated, and she wasn’t wearing tights. And her shirt was short sleeved. But that’s not the point. I hadn’t seen Beth in school uniform for weeks, ever since before exams started over a month prior to this. I always loved it when she wore a skirt to school, it was not her preferred attire, she chose to wear tight trousers. But in a skirt, she always got me hot.

My phone went off. “Beth looks cute, you need to come up with a girls name babe.” the message from Lucy shocked me. She wanted me to enjoy this, she wanted me to get this in my head to be a good thing.

“Lucy just text me, she wants” I started saying.

“To come up with a girls name” Beth interupted, “I know, she told me earlier. I have been thinking. I was going to suggest Jenny, but actually I think Jess would suit you more. It’s more flirty, and looking like that you could break any guys heart”

I felt hot. Not heat hot. I felt gorgeous. I felt girly. As soon as she said I would break any guys heart things seemed to click, I felt comfortable as Jess.

“Jess is fine” I said, she looked at me funnily.

“You don’t sound like a Jess.” She turned around and bent over, getting something out of her bag. She turned around and a flash went off. I was not expecting to have a photo taken of me like this. “You need to sort your” the flash went off again “voice out if you are going to go ahead with his”

“Jess is fine” I said, in a higher pitch than before. Beth looked at me, threw her camera back into the bag and walked up to me. She grabbed my hands and pulled me off the bed. She put her hands on my skirt clad ass as I stood up and held me close. I held her around her waist, not noticing how I was stood I looked at her and smiled.

“Am I really going to be able to pass as a girl for 3 weeks? I’ve never played hockey before, or netball or whatever else you girls do in PE. I have no idea on any of that side of it. What if a boy gets a crush on me? What if someone finds out?” I let go of her and crossed my arms, she took a step back and looked me up and down.

“You are standing like a girl you fool. You are already acting like a girl. You are minicking every thing you have ever seen a girl do. It’s fascinating. But I don’t care about that. I’m here, you’re here. I love you so much. And I want to have some fun with my new girlfriend Jess” she said so strongly.

I kissed her softly on the lips “I love you too baby”.

End Notes:

This is my first time writing any form of fiction. Hope you like

Chapter 2 by occwe
Author's Notes:

Jess' first schoolgirl crush! This is when everything changed for her.

The previous night was an experience, to say the least. I wasn’t sure what was going on if I am honest. I had a really fun night after myself and Beth were alone in my room, I never thought I would actually giggle like a girl, but I guess dressing like one changes a guy.

I lay in bed, looking straight at Beth who was still sound asleep. I was no longer wearing the blonde wig. I still had the black lace bra on, but one of the breast forms was out. That was the only bit of clothing I still had on.

I gently got out of bed, I didn’t want to disturb Beth. I sat at my desk and picked up the mirror that Lucy brought into the room when Beth and I were watching “Mean Girls”. Apart from the lack of feminine hair and a little bit of smudged makeup, my eyes were still really big and blue. I still looked girly. I wasn’t sure what Lucy had planned for me today, so I put on a pair of jeans and a t-shirt, rubbed off the makeup as much as I could and went downstairs.

Lucy was sat at the dining room table, reading an old magazine. “Morning Jess” she said. A little smirk on her face made me respond as I did.

“Not sure if you have lost your mind, but I’m James. Your younger brother. Jess isn’t here”, My response wasn’t angry or happy, or in fact anything other than normal conversation. I wanted to forget that I was wearing jeans and a t-shirt, I wanted to be wearing something more girly, deep down, I wasn’t too sure at that moment that those were the feelings I had. All I knew was that I didn’t feel “normal”. Lucy just sat there, continuing to read her old magazine.

I grabbed a half empty orange juice container from the fridge and went back upstairs. I didn’t really want any, I just wanted to see if Lucy was up or not. I got back into my room and grabbed all the various items of clothing I was wearing the previous night and put them on the chair next to my desk. Then I got to the skirt. I held it up, it looked shorter than I thought it was, or maybe that was just my perception of it now that I wasn’t feeling so excited. Either way, I couldn’t quite understand what I was feeling right then.

There were still a couple of bags that I hadn’t explored the previous night, a few items of clothing that Lucy had bought for me, inside one of the Marks & Spencers bags was a New Look bag and a Primark bag. Nothing spectacular, I thought, so I just emptied it all out on my floor to see what was there. The New Look bag contained a couple of tops with sale tags on, and the Primark bag had some leggings, tees and a few bits of cheap jewellery. I put it all back in the bags and chucked the bags under the chair. The next bag was all M&S stuff, couple of pairs of trousers, another black skirt and a pair of denim shorts. I guess Lucy was wanting me to dress up casual at some point. I put that bag behind the door.

So there I was, sat cross legged on my bedroom floor with 4 bags in total with girls school uniform and casual girls clothing in. This was all really weird. But I didn’t want to let anyone down now. I sat there, just staring into space. Not looking at anything in particular, not thinking about anything in particular. I didn’t notice Beth was now sat up in my bed looking at me. I didn’t notice her get out of bed either.

I jumped out of my skin when she kissed me on my neck from behind. Her hands on my shoulders. Shivers ran down my spine to start with. It was like total role reversal from the norm. You see, before last night, I was the big strong man, all being the little strong man. I wasn’t a jock, I wasn’t a geek. I had friends in every friendship group, not that I was popular. I played Rugby and Football, it was good fun to have girls screaming my name when I played well. But here I was, a partially macho 16 year old, sat on a floor, with a gorgeous girl behind me, quivering as if she was a big burly man and I was a petite little girl being touched for the first time.

What was going on?

For the rest of the day I stayed in my Jeans and T-Shirt. Secretly hoping that Lucy would come up and say “Hey, put the shorts, leggings, and one of those tops on - let’s go shopping”. But no, it was as if nothing had happened the night before.

6pm came around, a few texts from my Mum saying where they were on the journey home had arrived throughout the day and we were expecting her to be home, along with my Dad, in about an hour or so.

“JAMES!” I heard Lucy shouting from her room. I was playing on the PlayStation again. I ignored it at first. Kept on playing. Clearly she was annoyed.

My bedroom door slammed open. “For fuck sake James!” she shouted, throwing the blonde wig at me. “Why the fuck aren’t you answering my texts?”

“What texts?” I looked at her, my phone hadn’t gone off for about 2 hours. Beth was out with her friends watching some crappy film that I had no interest in what so ever, something about shiny vampires. I checked my phone. There were the texts. 3 in fact.

“Mum thinks you are staying at Beth’s tonight. She also thinks that a friend called Jess is staying over” was the first one.

“The more you ignore these the worse this is going to be. I am NOT covering for you ignoring me.” was the second.

The third was simple. “Mum and Dad will be home in 45 minutes. Get your ass in my room now.”

There was no way I could dress as Jess in front of my parents. How the hell would they even believe that I was anything other than their son in drag? They’d recognise me, ok so my Mum would recognise me, Dad would just be oblivious. That would be where I get my huge attention span from.

“No way Luce. Not a way in hell. I’d never pass for one. And I don’t think I can go through with this at all. I really don’t. What if someone recognises me? What if I fuck it all up?”, I tried to reason, Lucy was not having any of it. She left me in my room. The wig was on my lap. There were plenty of girls clothes in my room to wear as Jess. And considering that it didn’t take long to put makeup on last night, why would it now? I put the wig on, the pigtails from last night were still styled nicely. I got off the bed and checked myself in Lucy’s mirror, I could see Jess there already. I took my jeans off, took the boxers off, put the gaff and black lace knickers on. Pulled the leggings on and put the denim shorts on.

I tied my slightly over-sized t-shirt to my right hand side so I could see how the shorts looked. They were tight on my ass, made it look so feminine. Not short enough to look slutty, but stylish. “I must be out of my mind” I said to myself. I couldn’t decide if I should go ahead with it or not. Would Lucy agree to playing it off as a joke if the parents guessed it was me? Surely they would see the funny side.

“Luce! Can you call Mum and find out where they are?” I shouted. I didn’t want her to come into my room and see that I was getting changed. I put the bra on, and grabbed one of Beth’s shirts, it was red and blue checked. She left it behind a few weeks back after a friends house party that ended up with us staying at her place. I figured if girls can wear it with a denim skirt it would look fine with shorts too. I didn’t put the breast forms in, I was going to leave them til last. So here I was, stood in my room, with Blonde hair, wearing a girls shirt, shorts and leggings. I was just 2 steps away from being Jess again.

I wanted to see if I looked ok, the only place, other than the hallway and Lucy’s room, that had a full length mirror was my parents bedroom. How on earth was I going to get to my parents room like this? I grabbed my jeans, pulled them on over the shorts and put a hoody on over the shirt. I took the wig off and went for it. I had only taken a few steps before Lucy opened her door.

“Alright Missy? Mum and Dad stopped at services, lucky you eh? They are going to be another hour or so.” She said, leaning on her door frame. She almost smirked, but I think she wanted to make me feel like she was on my side, make me feel more comfortable.

“I am not becoming Jess in front of our parents Luce. No way. They’ll have me locked up!”, I said, I walked into the bathroom. There wasn’t a full length mirror, but if I stood on the bath I could see pretty much most of me. So I did, I completely forgot to take off the guys clothes covering my secret, it was silly. I took the clothes off and stood back on the bath.

I couldn’t see my face. I didn’t have breasts. But that ass! I didn’t bother putting the hoody and jeans back on, it was time to just admit it, I wanted to try it and why the heck not? I was 90% sure that Lucy would agree to play it off as a prank if the parents recognised me. I got to my room, closed the door, no sign of Lucy, her bedroom door was closed so she was probably in there. I put the wig back on, took the pigtails out and messed the hair up a little bit. I undid a few more buttons on the shirt and slipped the breast forms into the bra cups. I did a couple of buttons up and walked out into the hall. There was a makeup free Jess stood in the hallway, she looked like she was set for a day shopping with the girls.

I knocked on Lucy’s door in a similar way to how Beth knocks our front door, just thought I would make my own version up see if she noticed it. I popped my head around and in my feminine voice said “Can I get your help with my makeup again? I want it to look right.”

Lucy just stood up, and hugged me, and said “Welcome back little sis. Of course I will. Take a seat.”

It was not even 10 minutes later, I was made up as Jess once more.

“I like the shirt on you, but I think you need to wear a vest top underneath it, just because it’s fitted and it shows a bit of skin around your side. And you’re a little hairy too! The vest will be a little longer, but won’t cover your ass too much.”, She said, the advice was warming in a way, I took off the shirt and took the white vest off of Lucy and put it on.

She took a few photos of me posing, she took some on my phone and sent one to Beth. I was sure she would approve.

“Lucy, look, I will go and get changed if you don’t agree to this. I want to play this off as if it’s a prank if either of our parents recognise me as being James.”, I stated, I wanted to be firm, but was still putting on Jess’ voice. It seemed to work. “I don’t care if they see me like this, they saw me at Halloween so it’s not like it’s a new thing as such. But this is much more of an effort than ever before.”

“Jess, that’s fine. Of course, I understand. Look, you are doing me a massive favour doing this, I am not forgetting that. I knew you would help me if I pushed you a little bit, but I didn’t want to push you too hard. You have to be 100% sure that you want to help me out if that is what you want. If you aren’t 100% then you are gonna fail, be recognised as a boy and totally destroy my chances of writing a decent essay” ,she said, “I love you too bits. I know you can do this for me”. Her hand on my shoulder reassured me.

“Thank you” I said, smiling. I knew she meant it. I could see it in her eyes.

Time flew by, Lucy and I were sat in the living room watching tele and eating chocolate. Laughing at stupid things when the parents walked in, “Hey girls!”, Mum shouted as she walked into the kitchen. “Lucy, thanks for keeping the house clean. Has James been in today? He hasn’t been replying to his phone much. Hope he isn’t getting into any trouble with that girlfriend of his”.

Standard Mum talk, Dad didn’t say much, just sat in the arm chair, sighed and complained about the rubbish on the TV. We stayed for another half hour or so, until Mum piped up, “So Jess, haven’t seen you around before, you new to the area?”

Lucy and I made up a story off the top of our heads, and just kept going with it for a bit. We decided to go out. Why stay in with the parents? We met up with Beth and her friends after the film finished and went to the bowling alley and chatted. Time flew and the day was almost over. I went home with Lucy and slept on the inflatable mattress on the floor of Lucy’s room. When I woke up in the morning I freaked out to find Lucy had gone. I checked the makeup, it was smudged all over the place and I looked a mess.
I didn’t have any PJs or anything! What the heck was I supposed to do. I improvised and went to find Lucy wearing just the vest top and leggings. It was a gamble, but it played off. My parents didn’t recognise me, and they never said a thing all day. I left as Jess around midday, and this was the easiest part. Lucy came with me, I used the new look bag to take my guy clothes with me and took the Primark bag. We got to Beth’s, I changed back to James. And headed home, carrying a Primark bag containing Jess’ things.

The next few days went along OK, Jess didn’t make an appearance and Lucy didn’t mention it. I couldn’t stop thinking about her though. She was always with me, because she was me. I was thinking of her as a real person already. I spent a couple of hours every day researching various things. I wanted to educate myself, so I spent more and more time on my laptop. Practicing mannerisms in my room and such like. It was simply learning.

Lucy had arranged for me to visit the school I would be going to as Jess, she gave me no notice at all, well, she gave me 14 hours notice. She didn’t want Jess to go to the visit. I was going as a new Sixth Form student. But with a special drop in to the head Mistress. Not sure why, but I had decided before I went to sleep that night that I would wear my girly underwear and leggings under my male clothes to the school, the idea of it felt exciting. I didn’t tell Lucy of my plans.

We toured the school, visited all the departments that I would be involved in as a Sixth Former, and ate lunch with a few other prospective students. After lunch our visit was over, well, future sixth form students visit was over, I headed to the head’s office.

“James, I have been looking forward to meeting you for the past week since Lucy first mentioned the idea to me”, she said, shaking my hand and smiling. “I want you to know now that the only other person that knows about this is the head of administration and admissions. You are perfectly safe, no other member of staff will know who you are. When you start everyone will know you as Jess.”

“Thank you, I haven’t decided if I want to go through with it 100% just yet, I wanted to see how I could fit in with the school.”, I responded, “I’m 80% sure that I’m cool with it. But I have to make sure.”

“I understand, I completely understand. My specialism is Psychology so Lucy’s experiment intrigues me more than it would with other heads in the area. Maybe you could visit the school for a tour as Jess some time soon? Maybe a few days before you start? So it seems like you are like any other mid-term transfer student”.

The conversation continued, we made arrangements for me to drop in at the end of next week. For the next week myself and Lucy sorted everything out. The parents were told, they knew it was all about getting Lucy’s essay completed. And they were right behind me. The background story was that the whole family were moving to the area, Lucy was not a relation, I was an only child. As far as the story we were going to tell was at least. The school sent letters confirming Lucy as my personal mentor, it was all really official. The day came when I was to visit the school that I would be attending for 3 full weeks. The story we were to use was that I currently lived a few hours away, and I was visiting the tale end of the day. I was wearing my “current school’s uniform” - It was Beth’s cardigan, tie and blazer that I wore, I wore my skirt, my tights, my shirt and my shoes. My hair was in a low pony tail, and I wore subtle makeup that I applied myself. Nobody blinked an eye, nobody suspected that I was a boy, the afternoon went very quickly.

That weekend was really tense, Lucy, Beth and myself went shopping for clothes, mainly for some extra things, we also got some PE kit. I was all set.

The first two days of school were uneventful, I made a couple of friends and we got on quite well. They wanted to add me on Facebook and that’s where it hit me - I needed a proper back story. It needed to be in depth. We used photos of my cousin to create a few “old” pictures. I claimed to not have a Facebook set up because my parents were really strict. It payed off, and I set one up that evening.

The third day was when I met Matt. Matt is a popular boy. He was on the schools rugby team, and all the other girls loved him to bits. I thought he was a bit of a jerk to start with. That was before I worked with him on a poetry thing in English. I saw a side to him that cared. That was lovely. I guess you could say Matt was Jess’ very first schoolgirl crush.

I had to work really hard at all of this now. I didn’t want to get emotionally involved with anyone, but if I didn’t get involved at all people would get suspicious. I forgot that this was all a social experiment. And I did end up getting emotionally involved with a couple of the girls in a few of my classes.

We hung out after school on the Wednesday of week 1, and they ripped it out of me for having a thing for Matt. The girly voice that I was putting on worked well, nobody could guess at all. We talked about the weekend and our plans, I said that I had none and they invited me to join them on their shopping trip. I was scared, I’ve heard about Beth’s shopping trips - her friends shared changing rooms! I couldn’t do that! How on earth would I do that.

Luckily it didn’t happen, I didn’t share any changing rooms. I did, however, spend far too much money. I bought a couple of skirts for school, different styles to what Lucy originally bought me. I bought a hoody, three pairs of shoes and about £80 on makeup in Boots. Why? I have no idea! I only had 2 weeks left of this malarkey, I guess I wanted to fit in. Would look weird if I didn’t buy anything, right?

Monday came around too soon, I woke up at 7 and had a shower. The hairs on my legs had grown back a little already, and so I had to shave them because I had PE that morning. Mixed rounders in fact. We played rounders with the boys. Last week was horribly cold so I got away with wearing tracksuit bottoms, but today was promising to be one of the hottest days of July in a long time. Today it was game skirt or shorts. The shorts were too small for me, Lucy probably got them too small on purpose!

I wore one of the new skirts I bought on Saturday to school that day. This one had less pleats than the other pleated skirt I had, it also came with a black ribbon tie belt. I fell in love when I saw it, it was cute and flirty all at the same time. I wore tights, but not the same ones as last weeks, these had a diamond pattern. I put a blue ribbon in my hair that day too, I wanted to try some of the things I had been reading about. When I went downstairs Lucy squeaked. I have never heard her squeak before! I already had my bag packed with my PE kit in, and my school bag was packed up too. I was ready to go.

“You look so cute Jess! Is that what you bought on Saturday?”, looking at my new skirt, she said “You look so so cute! I do hope you haven’t got your tracksuit bottoms in there!”

I put my hand in and grabbed the games skirt, chucked it at her. She caught it, beamed and threw it back. “You know this is going so well. I can’t wait to start writing this stuff up!” she said. I left and met up with Bex, Effy and Charlie and walked to school. Matt was about 12 paces behind us from about half way to school. He was going to be playing rounders this morning. I so hoped we would be on opposite teams.

I hadn’t really noticed what was happening to me, I was acting like a girl because I had to. Or so I thought. Here I was, in the second of three weeks. Dressed in girls clothes, day dreaming about a boy. Wanting his attention. I didn’t snap out of it all day. I flirted. I got his number. He wanted to go see a movie together. I don’t know why I agreed. Doing the being a girl thing in school was fairly easy. Shopping with a few girls wasn’t that difficult at all. But being alone with a boy. What if he tried it on. What if he found out I wasn’t really a girl.
Chapter 3 by occwe
School was over for the day, I hung around with Effy for a bit after school. Beth was working until 5:30, so I decided to get the later bus back. Effy and I were in the local coffee shop, she had a crush on the barista there and wanted to show her face, again. She goes in pretty much every day that he works. Obsessive or what?

We were heading out of the coffee shop, she wanted to show me what she was going to buy her older sister’s baby for his 2nd birthday so it was off to the toy shop, when Matt walked in. When I say he walked in, what he actually did was incredibly goofy. Effy opened the door as he was walking in, he put his arm out to hold the door open but put it in front of her. To start with I thought he wanted to stop us from leaving, but no, he was just being a goon! He stumbled about for a couple of seconds, but it probably felt like an age to him, before he moved out of the way and held the door open for us. I put on the cutest voice I could manage and just said “Hey you! Thank you for holding the door open, you gentleman you!”, I did a sort of twirl as I walked passed him, Effy was watching him as I walked away.

“You minx. He watched you walk away! He checked you out big time! He so wants you”, she said, as we walked around the corner from the coffee shop and she linked arms with me. I blushed a little and could feel a stir in my groin. I was glad I was wearing a gaff, without it the front of my skirt would have lifted up for sure.

Myself and Effy went window shopping after the toy shop, mainly killing time, my bus was due to leave 20 minutes before hers, so we looked around in most of the clothes shops. She bought a couple of tops in Primark. She was trying to get me to buy something to wear for my date with Matt, but I had no money, and I didn’t want to use my card, or should I say James’ card, in New Look or River Island. I pretty much made my mind up about what I was going to wear, with Effy’s help. We found the tights first, they were an electric blue colour. I found a dark blue top with flowers on, it had an almost exact electric blue in the flowers too, so I figured it would work quite well with the tights. After ages looking around at skirts, I turned to Effy with a fed up look on my face.

“I might as well just wear that black tube skirt I bought on Saturday, the one that would be ALMOST too short for school, but could get away with it with tights”, I said, surprised that the choosing of an outfit was going so well. Effy agreed.

“Yea, and you could get away with wearing it shorter than you would to school too, pull it up a bit, it’ll pull in your waist even more and the top will sit over it. Nicely. Put the top on now, you’ll get a good idea of how you will look.”, She wasn’t condescending, as much is it sounds it now, looking back, she really wasn’t. It was sound advice, which I really appreciated. We went back to where we found the top, I took my cardigan, tie and shirt off without even thinking about what you could see! The black top I wore under my shirt that day covered me enough to not see the breast forms. I pulled the top over my head and flicked my hair out.

“How does it look?”, I said to Effy, who put her hands on the waist band of my skirt and pulled it up. I jumped a little, “Right, look in the mirror. I think that should be how long the skirt should be. Imagine your black tights are blue. What do you think?”

“I think this is perfect”, I said, smiling at my reflection. It looked perfect. The skirt wasn’t ‘right’ as such, but I could see the length that would work well with the tube skirt. I put the top back on the rail and put my shirt back on, not buttoning it up as much as normal, and I just pulled the tie up until it sat just about where my cleavage should start. We headed off to the bus station after that, I had about 10 minutes before my bus left, so I didn’t want to see anything else that I may or may not end up buying.

I got home, Beth was still going to be working for about half an hour, so I decided to get changed back into James before meeting up with her. I hadn’t seen her without wearing my new school uniform in just over a week. So I wanted a change as much as anything.

“JESS!”, Lucy shouted. She stood mid-walk just staring at me.

“What?”, I asked in a brattish tone. I had no idea where it came from.

“You look like a tramp! Have you warn your uniform like that all day? You looked cute when you left this morning, and now you look like a slut!”, she never complained about anything I had worn before, I wasn’t sure what she was going on about.

“It’s just one button more undone than normal, that’s all”, I said, thinking that is what she was talking about.

“And what about the fact that your skirt barely covers your arse?”, she sounded angry still.

I went to grab where the hem would normally be. “Shit” was the only word that came into my head. The hem was at least 2 inches higher than it was before Effy pulled it up. It would have been fine if the skirt wasn’t pleated, but the skirt lifted slightly as I walked anyway, so who knows what people saw in between me leaving Top Shop and getting home. I explained everything to Lucy and she just shook her head.

I had a shower, removed the smell of girl and covered myself in body spray. I don’t think I had smelt like a boy for 2 weeks to be honest. It felt unusual. And I was lucky to find the deodorant that I sprayed on me every day up until a couple of weeks ago! I got dressed and sat down at my desk, and put the headwrap on to keep my hair out of my face. I put on a layer of foundation and was about to start to apply some blusher when I realised what I was doing. I was on auto-pilot, it was my standard routine after putting clothes now. It wasn’t the first time I had made the same mistake.

After washing the makeup off, I decided I would take Jess with me. Just in case Beth wanted her to come. I packed the tube skirt I was intending to wear on my date with Matt, a tee from Primark that Lucy had bought for me on day 1, and the superdry hoody that I bought on my shopping trip with the girls. I didn’t have space to put Lucy’s ugg boots that I had now claimed as my own, temporarily, so I went with the pink flats that I bought to go with the hoody. Underwear, wig and breast forms in and my bag was pretty much full. I just managed to fit my small makeup bag that I take to school with me, just in case I need to touch up my makeup during the day, in my rucksack.

“Just about to finish work babes, looking forward to seeing you! I’ve found a job you may be interested in. Meet you in 10? xxxx” read the text that Beth sent to me. A job... Ok, I knew I should get a summer job, but where had Beth found? I guess I would find out soon enough.

I rushed down stairs.

“JAMES!!”, Lucy shouted as I opened the front door.

“WHAT?!”, I shouted at her, pissed off that she stopped me once more.

“James, seriously. What are you doing?”, she said, “I can only assume you want to get caught out.”

I had no idea what she was going on about. I just stood there, my left hand on my hip, my right hand holding onto the strap of my rucksack. I quickly adjusted my posture to more of a manly stance.

“James, I know you have spent the past week or so as Jess, but if you’re going to go out with no makeup and no wig, you could at least make sure that you were wearing boys jeans.”, She said. Her voice was calm, and sympathetic.

“What do you...”, I then realised, I felt the draft. I hadn’t put on my jeans! I had my boxers on, I didn’t have a bra on, I was wearing a green t-shirt and a baggy black zip up hoody. But instead of me putting on my jeans, I had involuntarily put my school skirt back on, and I was wearing Lucy’s uggs. I must have just put the uggs on because I was thinking about taking them with me. “Oh shit it.”, I said in a hushed voice as I dropped my bag to the floor and rushed back up to my room.

10 minutes later I had my arms around my gorgeous girlfriend. I kissed her as if I hadn’t seen her for an age. She was in her work uniform so she wanted to drop home and get changed. She worked in a pub as a waitress, so she wore a black top and either a skirt or trousers. Today, she was wearing a black shirt and a shortish tube skirt with what looked like 50 denier tights. She was wearing a black strappy top under he shirt to cover more of her cleavage. The work shirts she wore were really tight around the bust. It wasn’t lust that made me attracted to her today, it was the fact that I wanted to be wearing what she was, she looked pretty and sexy. I think the spending time chatting to girls was changing the way I thought more and more. The lines between James and Jess were being rubbed out.

“You’re mincing”, Beth stated as she stopped in front of me, her hands on my chest, “If you are going to keep walking like a girl and checking out men’s bulges I am going to get annoyed. Snap out of it will you. Please.”

She sounded annoyed, she looked upset. Was it jealousy or was she scared that I was becoming attracted to men, not that I was, I was just comparing other guys to Matt. Wait. What was I thinking? The fact that she mentioned the men’s bulges frightened me a little, was it that obvious?

“I’m sorry. I really am. I’ve just been so used to having to be able to comment with the rest of the girls and be quick. It’s so tough. I won’t do it again.”, I said, kissing her on the forehead. She put her arms around me and squeezed me tightly, then grabbed my hand and dragged me into the charity shop we were stood outside.

“Look at that outfit!” She said, excited, pointing at this dress, it had white tights and a blue headband on the hanger with it, “You would look so cute in...”. I was so glad there was nobody else in earshot!

“Are you actually serious Beth? You’re going to have a go at me and then this?” I asked, confused.

“Come on baby, I want my Jessy Wessy to jump through the rabit hole and be my Alice”, She whispered into my ear. I felt a stir in my pants. I was excited, wouldn’t anyone be?

“I’m not sure Beth, I said. Will it fit well?”, I said, knowing that it would fit me if it fit her, her waist was just a little smaller than mine and she was about an inch shorter than me. She knew what I meant.

“Tried it on whilst I was waiting for you, I finished work early, I saw it here on my way to work this morning and wanted to see if it was still here. I told them that I wanted you to say if you liked it or not before I did. They put the sold, awaiting collection tag on it for me so it would still be here. “, Beth explained, I didn’t know what to think. I didn’t have a suitable bra to wear with it, and Beth’s bras were all bigger than mine. Why I worried about having a matching bra I do not know, but clearly it was important.

“I need to get a strapless bra for this, you wanna come with or are you gonna wait somewhere for me?”, she asked, I opted for the waiting somewhere for her, I just sat on a bench just up the road. Everywhere was just about to close so I couldn’t be bothered to go anywhere.

We got back to Beth’s just as her parents were leaving for a dinner party. “I haven’t prepared anything for you to eat guys”, her mum said as she walked past, “Is that an Alice dress?”, she said, looking at the bag in Beth’s hand.

“Yea, it was a tenner, it fits, so I figured, why the hell not?”, Beth said, her mum looked at me.

“This your Halloween costume for this year is it James?”, Tracy, that’s Beth’s mum, said to me with a grin on her face.

“Nah, I’ve decided I would probably suit a St. Trinians to be honest”, I said, not realising I was talking in Jess’ voice.

“Well you sertainly have the, erm, frame to pull it off”, Tracy replied, you could tell she wanted to comment on the voice she had just heard. She left us, Beth looking at me with an expression of “Why on earth would you do that infront of my mum?” on her face.

So here we were, home alone, Beth went to her room, I followed her as per the norm. I sat on her bed whilst she took her hair out of the tight ponytail she had it up in.

She turned around and pushed me back on her bed. She was fairly spoilt, so her king size bed was enough to make anyone feel small. She straddled me, her crotch touching mine. Her hands on my stomach. I felt like the petite little girl again.

“So, this job. Theres a waiting staff job going at work. We can spend more time together over the summer if you take the job”, she said, as she rolled off me, snuggling up next to me.

“Oh cool, that sounds like a good idea. Just waiting? Or do they expect me to be a dish pig as well?”, I asked, knowing for well that they made her do the washing up sometimes, purely because she never made a fuss, she just got on with it.

“They’ll make James do the washing up”, she said looking straight up to the ceiling. She didn’t say anything else.

It sunk in.

“You told them you have a friend called Jess who has just moved into the area and want’s a job didn’t you?” I asked, she jumped off her bed and went to her wardrobe.

“Strip. Get your underwear out of your bag Jess.”, Beth ordered, as she got opened both the doors to her huge wardrobe. She chucked a black tank top at me. I pulled on the gaff and knickers at the same time, I’d gotten the tucking perfect now, so on went the bra and breast forms. I put the tank top on and grabbed my wig. By the time the wig was on Beth had gotten a shirt and some tights out for me. She also got a pair of her old school trousers.

I say old school trousers, because these were particularly tight, they were boot-cut, but they hugged the skin from waist to knee, they accented the arse, hips and yea, you get the picture. Beth wore baggy trousers to work now.

I grabbed the trousers and put my feet in them. “Wait.”, Beth interupted. She chucked a skirt at me, it looked way too long for anyone that worked with her to wear. I chucked it back at her.

“No way am I putting that on! I’d look like a twat.”, I said calmy. I grabbed my long blonde hair and put it over my left shoulder as I bent down to grab my little tube skirt out of my bag.

“Here we go. This will do won’t it?” I said as I pulled the tights over my knees. Beth walked out of the room and so I adjusted myself and started putting makeup on. I was just guessing that she wanted me to go the whole hog.

A couple of minutes later and she came back, she had a pair of shoes in each hand. She got down on her knees and spun the computer chair that I was sat on, she put the first pair on my feet. They were black with a small heal, probably about 3 inches. This was the first time I had worn heels since this whole thing started. She told me to stand up and look in the mirror. My legs looked so long, way longer than ever before. I had put a hair band around my wrist whilst doing my makeup, so I quickly worked my hair into a low pony tail just to see how I would look like if I did embark on a summer as Waitress Jess.

Beth came and put her arms around my waist from behind, leaning out to the side and looking at me through the mirror. She smiled, and I copied.

“I love you so much Jess, I’ve missed you baby.” She said in a really soft voice, she had never looked at me like this before, it was lustful and guilty all at the same time. She went on tip toes and kissed me on my neck. I turned around and looked at her, I knew that I looked like a girl who was about to embark on her first contact with another girl. Ok, so about a month ago I had a night of fun with her, but that was before I felt like a girl. Yea, that’s right, I felt like a real girl now.

We fondled a little bit, we played with each other, she never touched my crotch, it was is if she was avoiding my cock, as if she was imagining that it didn’t even exist. She opened her bedside cabinet’s top drawer. I knew exactly what it was in her hand without even looking. She put it in front of my face and looked at me with eyes that told me exactly what to do. I opened my mouth slightly and push my head towards it, I poked my tongue out a little, it made contact first with the silky soft texture of the fake pink phallus that had been presented to me.

Beth didn’t force it on me, she just held it in the same place. I pushed my mouth over it, my lips holding it tightly, I pulled my head back and forth for a little. Then, I pulled away, the slurp noise I made was familiar from the porn movies I had seen in the past, and from the couple of occasions that Beth had given me head. I blushed as Beth giggled.

She put the dildo back in her drawer, I never saw it again. She was just teasing me, testing me. We kissed a bit but nothing more, I hadn’t made plans to do anything or go anywhere but Beth had. We went to the cinema, after I changed out of the potential future work wear and back into my male clothes. The film was average, I walked Beth home and went back to mine. It was fairly late, nobody else was still up, so I went to bed.
Chapter 4 by occwe
I didn’t sleep too great that night. The incident with Beth’s dildo played on my mind. A lot. I couldn’t understand what I was doing. Why was I doing this? I was a boy, who was pretending to be a girl so my sister could monitor peoples changes in behaviour depending on their environment, and how others around that person perceived them. I was acting. That’s all.

I showered, Underwear on, the new bra that Beth had bought for me would be tested out well today, put tights on but wore trousers instead of a skirt. I was scared, what it someone saw me last night looking like a total slut? I chucked on some makeup, a little bit more eye liner than normal, but hey, I figured why the heck not. I didn’t bother with a vest top under my shirt, it was too warm for that. Besides, the new bra was white so it wouldn’t show through my tight white shirt, which was tighter than normal since the new bra made my boobs bigger than before.

I put the wig on last, as normal, and put it into a plaited it. It didn’t feel right. So I took the the plaits out and and sat there. What on earth could I do with it today. Time was running out so I grabbed a blue headband that my Mum had bought for me because it ‘works well with your eyes, and it’s cute’. That worked well. It had small pink flowers on, so I wiped the light blue eye shadow I had applied and replaced it with a really light shade of pink, you couldn’t notice that it was there unless you knew it was there, which was pretty cool. I grabbed a baby blue hair tie and put my hair into a loose ponytail.

I grabbed my rucksack, grabbed the small makeup bag, put the pink eye shadow in it and then chucked it into my school bag. I didn’t know whether I should take a skirt with me just in case I changed my mind about wearing trousers. And then which one? The one that Lucy bought me was simple, it folded down quite small, but then so did the other ones. It was either the same one from the day before or the tube skirt. I was going to miss the bus if I didn’t get my ass in gear, so I chucked the tube skirt in my school bag and left for school. Grabbing the pink phone case, I’d swap the black one for it when I got on the bus.

The day went by fairly quickly, up until lunch. Charlie linked arms with me and dragged me to the loos after leaving Maths.

“So, what are you going to wear?”, she asked. “Effy said you were going to buy some new clothes for your date with Matt tomorrow. Go on, what you chosen?”

“Come with me after school, you can see the outfit in full”, I said, grabbing the skirt out of my bag. “I brought this one with me so I could get a feel for exactly what it would look like”

“You should so wear that this afternoon! We have English with Matt this afternoon, you should give him a preview”, Charlie rushed to get the words out, I think she was more excited that I was.

I got changed into the skirt, as I put my trousers in my bag my phone vibrated.

“Beth told me about your date on Wednesday with that Rugby boy...”, It read, it was from Lucy.

I replied with “And?” and chucked the phone in my bag. Charlie and I went to grab some food, I wasn’t hungry so just bought a small orange juice carton. We were walking to meet the rest of the girls who were in a different Maths group to us when I heard someone shouting “JESS!”, it was Lucy. She made some stuff up about talking to her about the issue I had with Biology, I had no idea what she was talking about, but agreed to find her before next lesson.

Me and the girls chatted like me normally did, giggling at stupid things and talking about what we were going to do this summer. I told them how a friend from back home had found me a job in a pub as a waitress. Time flew, and it was time to find Lucy.

“You need to sort your hair out”, she said, “It hasn’t changed, grown or anything in the past couple of weeks. I’ve spoken to Tammy, she said she will cut it and whatever tonight after she has closed.”

Tammy was an old friend of Lucy’s who had started working in a salon a few months back, she did Lucy’s hair and always did a good job of it.

“What do you mean? Sort it out? It’s a wig, surely it’s fine?”, I asked, not quite getting what she wanted me to do.

“Look, I think you should get it dyed, layered and just improved. Most girls your age are doing it, and your hair just looks too natural. Here”, she passed me a torn out page of a magazine, it had a woman with a hairstyle very similar to mine.

“That’s the same as mine you muppet. There isn’t any difference.” I said.

“Turn it over, look at what the stylist did.” Lucy responded.

The other side of the page had the same woman, but she looked much more sophisticated. Her hair was just a little shorter than before, but layered, it had been died a dark brown apart from the top few layers. It looked pretty cool. The large photo was inset with the hair in different styles, in a high pony tail, in two plaits - one each side of her head. It looked good, I could easily pull it off.

“Will the wig stand being died, cut, tugged and what ever else?” I asked. Lucy didn’t even bother talking, she just nodded. As the bell rang for the next lesson to start I agreed to go get my hair cut.

English wasn’t anything special, Matt wasn’t there so wearing the little skirt just got me in trouble with the teacher. Never mind.

I went shopping with Charlie and Effy after school, grabbed the clothes that I had seen the previous day and went for a coffee before catching the bus home.

Lucy took me to Tammy’s salon, and showed her the magazine page she had shown me. A couple of hours later and we left the salon. My new hair made me look a lot older, more like I was 20 rather than the just 16 year old that I was pretending to be. I loved the pampering, even if it wasn’t my own hair.

Wednesday flew by, before I knew it I was at home, getting changed ready to meet Matt at the cinema. Lucy was going to drop be in and then pick me up again. As we got into her car she passed me a small pink box with a purple heart on the front of it. It read ‘Vera Wang Princess’.

“You are a princess, so no reason why you should not smell like one”, Lucy said.

“Thank you so much Luce”, I said, as I hugged my big sister. I took the purple heart shaped bottle out of the box and sprayed a little on my neck and arms.

Lucy dropped me off a little way away from the cinema so she didn’t embarrass me, and I walked to the cinema. Matt was waiting outside for me, he saw me coming which was helpful. I had been trying to think of what I would say to him to start a conversation and couldn’t come up with anything.

Matt complimented my new hair, that was the first things he said after “Hey”, we went into the screen and sat just down from the back row. About 10 minutes in he tried the stereotypical arm stretch. I didn’t budge. I ignored it. He gave up. I got really comfortable in his presence though. I hadn’t noticed my own body language, I was leaning towards him by the time we were halfway through the film. He tried the arm stretch again. I turn around and whispered “if you want to cuddle then just ask me! I wouldn’t have agreed to come on this date if I didn’t like you Matt”. I don’t know why I said what I said. Or where it even came from. I don’t think he quite knew how to react. So I lifted the arm rest that was in between us, and leaned into him, he wrapped his arm around my waist and tickled me side. I squirmed and sat around, looking at him. He smiled. He looked so damn cute with a cheeky grin on this face.

I couldn’t resist, I had to see what it was like. I looked down and back up, I wasn’t checking him out, I wanted him to attempt to kiss me. I wasn’t going to give in this time around, I wanted him to have the idea in his head, see how he did after sitting there with his arm around me for a little bit. A further 10 minutes or so into the film I put my hand in his knee. I was running with things that Beth had done on a date with James once. I snapped out of being Jess for a bit, I hope he didn’t notice me pulling my hand off his knee so quickly. I made up for it by linking my fingers with his. That’s when I lent back a little and looked up at him. I was letting instinct take over, the fluttering of my eyelashes worked. He leaned in and kissed me. I went squidgy all over. Matt kissed me. The Matt kissed me! He didn’t know my secret. He couldn’t work it out. I kissed him back and sat up, put my arms around his neck and kissed him a bit more. His hand was on my thigh, I hadn’t noticed to start with, but when it reached my crotch I noticed big time. I pushed him away gently. “Too soon Matt. I’m sorry hun. Just too soon”

It most certainly was not too soon. I would have let him play with every part of me there and then, I was loving it so much. I decided I would try playing with him a little. I moved my left hand from his knee to his groin. I didn’t move my hand, I left it there. I could feel him grow in my palm. I rubbed him a little, not to hard, just a bit of a tease. The film was soon over. He asked if he could walk me home. I said that was fine, but his house was on the way to mine, so we went for a walk around the local park, took a seat and looked up at the stars together.

We kissed a few times, he never tried touching my groin, he didn’t force me to go anywhere near his, but I did anyway. I played more this time, we had nobody near us. It was deadly silent out and I wanted to see what it was like. His cock was so hard by this point I asked him if he knew anywhere more private. I don’t know why. Something was making me want so much more. We walked for about 5 minutes, he jumped over a wall and opened a gate from the inside. He had obviously been here before. I didn’t care. I closed the gate and threw my arms around him, he picked me up and carried me across the private garden and gently put me down. He rolled off of me and held my hand, I rolled over, my hand on his chest, I looked into his eyes and just got lost.

Before I knew it my fingers with pretty painted nails were wrapped around his hard member. I was on auto pilot. I didn’t want things to end anytime soon. He didn’t force me. He didn’t act weird. He just let me go. I let go of his cock, I kissed him again and said “I’ve never done this before” in the softest voice I could manage. He smiled, “you are doing just fine, by all means keep going, I’m enjoying your touch. Stop when ever you want. No pressure at all.”

I stopped for a bit. “People have you wrong, you’re one of the nicest guys I have ever met Matt. You really are a true gent.” I kissed him on the cheek, moved my hand from his chest down to cock again, and started slow again. I’d got the pre-cum on my hand, and I have no idea why, but I couldn’t stop myself from licking it off my hand. I was acting like a total slut. It was if I was personifying what I had wanted Beth to be like, what I saw porn stars being. It didn’t matter, I was in the moment. The taste was different. I’d never tasted anything like it, so I just kept going. I stood up and faced him. At that point I didn’t know if I should pull him up and get him on his feet and go down on my knees or kneel down straddling his legs and go from there. I went for the latter.

I was on my knees, straddling his legs, I put my left hand around his cock, and I moved my head down. As his hard cock touched my lips I opened my mouth just a little and moved my tongue over the head of it. I looked up at him and he was just looking at the stars. I felt so horny at that point.

It wasn't long before Matt came. I got a little on my chin as I pulled off of his now limping penis, but that was fine, I didn't care. I contemplated spitting it out, but decided i’d swallow his load. I lay next to him, we cuddled for a bit before my phone went off. Lucy wanted to know where I was. We made a quick escape, not before making out one last time. He walked me to Lucy’s car, gave me a hug and then kissed me on the cheek before I climb in and left.

“Did he actually kiss you then?”, Lucy gasped.

“Yea. And we made out in the cinema. And...”, I told her.

“I don’t want to know, what happened on your date stays between you and him. He’s cute by the way”, Lucy said, a little smirk on her face.

“I know right? He’s not as much of a jock as he looks. He didn’t ask me to be his girlfriend though”, I said, not realising what I just said.

“James, I love how you are taking this all so seriously and taking lots of steps to make this real for everyone around you, but you do realise that this is just an experiment. It’s going to be over by the end of next week.”, Lucy stopped, her smirk had vanished, she looked serious.

“Who’s James?”, I said, with a confused look on my face. I was just pretending. I knew what I was doing. I did want to see Matt, as Jess, for a bit though. Up until the end of school or maybe the end of the summer. After all, I would be attending sixth form as James, Jess wouldn’t exist then.

“I love you James. Can we spend some time together this weekend”, my phone read, it was a text from Beth. She knew about the date, she was fine with it, I promised that I would do no more than kiss Matt, she was cool with it. The rest of the date would remain secret. I agreed to meet her and told her that I was going to get an early night.

“I would love to see you again Jess. See you in English tomorrow? Matt xx”, a second text came through soon after I had replied to Beth’s message, I didn’t reply to it until I got home. Once home I replied and we ended up texting for quite a while, it was almost 1am by the time I fell asleep.

When I woke up at 7:30am the next morning I had a spring in my step. I was still on cloud nine from the date that I had the previous night. I had a shower, got dressed, chose to stick with the skirt I wore on Monday. In fact, I was pretty much wearing exactly the same as I was on Monday, normal black tights, no pattern and no vest top because I had proper cleavage.

Beth called me when I was on the bus into school, her boss wanted to know if I wanted to have a tryout this weekend. Bang went the time with Beth as James. She gave me his number so I knew who it was when he text me.

English was interesting that day. Matt wasn’t off with me, but he most certainly wasn’t on. For the whole lesson he didn’t really make any form of eye contact. I was devistated. What had I done wrong? Was I too soon with my actions? My mind filled with all sorts. The lesson was over and I left the room alone, ignoring Effy & Charlie. I was quiet for most of the morning.

At lunch Matt turned up to where me and my girls hung out, he hugged me from behind and asked if we could talk. I melted. What was he going to talk about? I agreed and went for a walk with him, we walked to one of the quietest parts of the school, it was so rare to see anyone outside of lessons here.

“I really like you Jess”, Matt said, as he took hold of both of my hands.

We talked for a while, within 5 minutes I had my first boyfriend. We kissed and then walked back to my friends, holding hands. Bex saw me first, I saw her nudge Effy, who was sat next to her and then saw Effy kick Charlie who was opposite her. They all looked at the same time, jaw dropped and then massive smiles.

The rest of the day went by, I had a text from Beth’s boss, his name was Tom by the way. I had agreed to go and say “hello” after school. But Matt wanted to hang out. Naturally I stuck around with Matt for longer than I should have, I caught a bus back home and dropped into the pub when Beth was working. I was still in my school uniform and Tom seemed to take a shine to me sooner than I was expecting. He offered me the job there and then, I asked how much I would be paid and how often pay day came around. I was asked to start on Saturday lunch.

“Wear either black trousers or a skirt and tights on Saturday. Wear a black top, You can grab a work shirt when you get here.” He told me, before I left.

I was about to embark on a whole summer of being Jess. Something that I wasn’t planning, but getting a job as Jess was a hell of a lot easier than it was when I was James. I had tried, nobody wanted a geeky waiter.

Matt text me all night, I was gutted about not being in the same town as him. We sexted a little, but I fell asleep early that night.

Thursday was a boring day in school, nothing much happened, Matt hung around with me and the girls at lunch, but that was about it. I had arranged to have Lucy pick me up from Matt’s house after school so I could spend more time with him.

Matt and I had the house to ourselves. I’m not going to go into too much detail, but he found out my secret. It was a mistake. He didn’t over react at all really. He wasn’t upset, or angry.

"I asked you out on a date because of the way you make me feel. Because of the way you are. You are the girl that every guy wants to be with and every girl wants to be like. I was never in a million years expecting you to not be 100% female. You had me fooled. But I wasn't going to stop you, I wanted to see what you were like. What you wanted to do. Your touch has made me feel happier than I ever have before. And that's all after I found out about your secret.", he said, blushing.

“You’re cool with this?”, I asked him, my hand on his chest.

“Yea, totally”, he hesitated, “I can’t say that I will be playing with your cock. But I enjoy your company as my girlfriend. I’m going to find it difficult to adjust, I think. But yea, I’m cool with it”. He smiled, we kissed, and lay on his bed watching TV.

Over the next half hour we messed around. We kissed. But that was all.

Lucy picked me up, and I told her about his reaction to finding out my secret. She didn’t respond, she changed the subject.

Friday was mostly good. Matt was a nice guy, he didn’t tell anyone my secret. He did ask to go out on Saturday night, I agreed, forgetting about my promise to Beth. I was on the phone to Beth about Matt asking to spend time with me on Saturday that even, she suggested that all 3 of us went out together. I was hesitant. I called Matt and explained to him, he got angry and hung up the phone. I left him alone and called Beth back. She laughed and reassured that I would get a text from him in no time at all.

She was right, about 30 minutes later I got a text from him, “I’m sorry Jess, I’m just confused. wouldn’t it be weird?”, it read. I called him, reassured him that it wouldn’t be a problem. We made plans for all 3 of us to spend some time together. I would be Jess, James would not make an appearance.
Chapter 5 by occwe
I slept like a baby that night, woke up nice and early, got changed for work and went to Beth’s place. Work was great fun, I enjoyed the light flirting with the customers and the heavier flirting with the other staff. It went really quickly, and I enjoyed it a lot better than I thought I would. Beth and I headed back to mine, we had a couple of hours before we were to meet up with Matt. I took my hair out of the ponytail, swapped my skirt for a pair of skinny red jeans and swapped my work shirt and black tank top for a white tank top and a white hoody that I had bought on eBay. I topped up my makeup and put Lucy’s UGGs on.

Beth and I headed over to hers and she got changed. We messed around for a bit and then headed off to meet up with Matt. We had arranged to go grab some food and then catch a film and then see what happened after that. Matt and Beth hit it off quite well, which was kind of weird. We all headed to the quiet area where Matt and I went on our first date. I was never in a million years expecting what happened next to happen. And I am not going to go into too much detail, let’s just say it was the first time I had experienced a threesome of sorts.

The next week at school was a wind down, over summer homework was set by some teachers and a few fun things to do. I had worked a couple of nights after school at the pub, spent time with Matt, spent time with Beth both as James and as Jess. My double life that week seemed to be rather manageable. Friday was the last day of school and we finished early, Matt and I went back to his and spent some time alone.

For the next couple of weeks I was working at the pub with Beth, spending a couple of nights with Matt, and the rest with Beth as either Jess or James. Then it all came crashing down. Matt had decided it wasn’t what he wanted, he couldn’t cope with knowing the truth and pretending, I was kind of gutted, but I figured I still had Beth and she was the one the mattered most.

The rest of the summer holidays was just work work work, I saved up all my money apart from the bits and bobs I bought to keep Jess alive for those precious few weeks. And then it was all over. It was time to become James again and head off to Sixth Form. Beth and I stayed together and I would go as far as saying that Jess made our relationship a lot stronger. I would occasionally dress up as Jess for the fun of it, but there was no real reason to do it.

AS level work took precedent and I was learning to drive so the money I had made as Jess was soon spent on that and a crappy car. I needed to get a job, I found job in the corner shop just down the road from where I lived, it was only weekend work, but that was all I needed to pay for the fuel for my little red Nissan Micra.

So, I guess I should reveal how Lucy got on with her Uni application, she got in, not only did she get in, but she got into the best Uni she could have hoped for. And I should probably reveal that I haven’t been as honest as I should have been. Jess made more of an appearance than I have made out. In fact, I never stopped wearing the gaff that Lucy had bought me, I got so used to the feeling of it I kept it on. I occasionally wore girls clothes under hoodys, and I generally wore girls underwear. I was never caught out, I was always careful. Not even Beth noticed.

After I started driving I had a little bit more freedom, so when Beth wasn’t able to spend time with me on a weekend I would get in my car and go for a drive, I would stop somewhere with public loos and get dressed up as Jess, I’d then go off and go shopping or what ever. I loved the thrill of it, I could pass as a Jess easily, so why shouldn’t I go and do it? I joined some online groups for cross-dressers, and met a few of them over the next few months. I even went out on nights out, and I was regularly mistaken for a real girl amongst the others.

Over the first summer of Sixth Form things really changed. I had been growing my hair since first becoming Jess, but it always remained boyish. Then I talked to Beth about how I was missing being Jess, how I missed being pretty, and how I missed the clothes. We spent hours and hours over the first few weeks of summer talking through things and what I could do. I was confused, scared and even more scared that I could end up alone if Beth got freaked.

I had to make a choice, was I James or was I Jess? I fitted in as Jess more than I fitted in the world as James. I phoned up Lucy in tears.

“Luce, I really need your help and...”, I couldn’t continue, I just blubbered down the phone.

“James, what is wrong? Come on.”, Lucy replied in a tone that reassured me a little.

“I’m confused. I’m really confused.’, I continued, “I miss being Jess. I really miss it. I miss the clothes, the makeup, the flirting with boys, the attention, all of it. I don’t know what to do”

“You could just become her”, Lucy’s reply was very short.

Neither of us said anything for a few seconds, but it felt like hours.

“What do you...?”, I replied

“I mean exactly that James.”, Lucy continued, “You could go to the Drs, you could talk to them about the possibilities of going on hormones and becoming Jess for real. Look, I was never expecting you to adjust to the experiment as much as you did. I most certainly didn’t expect you to become attracted to guys.”

“I’m more attracted to girls.”, I made clear to Lucy.

“Yea, ok, whatever. Look, what I am saying is you can become as real as a woman as you like you know? It’s not unheard of.”

Our conversation lasted about half an hour. We talked about the pros and cons, and in the end I agreed to try the talking to my GP.

So here I am, at the end of sixth form, about to start my final exams. I’ve been on hormones for the past 8 months. I’m still living as James most of the time, only I have to wear baggy hoodies and jeans to cover my new physique. Beth and I are still together, she has been the rock I have needed. We have booked a little trip away once our exams are over and the summer holidays have started. James won’t be around, I will spend the entire trip away as Jess. Beth seems more excited about it than me.

I found a small handwritten letter from Beth a couple of days ago, here it is:

<blockquote>“Dear J,
I love you very much, but there are a few things that have obviously changed in the past few years. Don’t take this letter the wrong way, really there is nothing but positive in here and I will try to keep things as simple as possible.

The more time I spend with Jess the more time I want to spend less time with James. I think everything that has happened with us has made me fall for Jess more and more in love with her than I ever was with James.

You really have made the best decision, and I love you very much.

B xxx

PS. So looking forward to the fun times on holiday ;)”
</blockquote>

When we come back from our trip away, James will no longer be around. Beth and I will be girlfriends, and I will be living full time as a girl.

After everything that I have gone through, I have my dearest sister to thank. I have never felt so happy.

I will make a few updates as things go on.
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