Blackmailing Biscuit
Chapter 1 of 4

© 2013 D.L.

I rolled the stockings up my hairless legs, making sure that the seams were straight. I attached them to the black suspenders that I fed through underneath the lacy French knickers so that they could be removed without disturbing the stockings. I was actually wearing two layers of underwear, as I had an extra pair of plain knickers underneath the extremely frilly lacy pair on top.

I tucked myself, but not tightly. Unlike the numerous other times I have cross-dressed, this time I didn’t have to worry about trying to pass. As everybody at school would know I’m male, it’s not important if I have a slight bulge. In fact, it may be odd if I don’t. The one thing I could guarantee was that my underwear would be on show. The skirt of the school dress is exceedingly short, only a couple of inches below the top of my suspenders and barely reaching halfway down to my knees.

I fastened the blue and white diagonal striped tie around my neck, adjusting the collar of my white blouse and tucking the tie into the top of the dark grey dress. The dress was slightly tight round the bust due to the overly large bags of birdseed that I positioned in my bra. I am going for the Barbara Windsor look concerning my proportions.

Leaning forward into the mirror, I applied my lipstick, bright red of course. I had already overdone my eyes with mascara and blue eye shadow. I drop my makeup into my school bag in case I need to touch it up later. Giving one final look in the mirror to make sure that none of the clips from the hair extensions were visible; I slipped my shoes on my feet and headed for the door. I have styled my false hair so that it is in two braids that cover my shoulders and hang down to my breasts. My actual hair is a lot shorter and only just reaches my shoulders. I usually wear it in a low boy ponytail.

I descended the stairs with my school bag and walked into the kitchen where my mother and friend, Stacy, were waiting.

“Holy cow!” Stacy exclaimed at my entrance.

My mother spun round and gave me a long look. “That skirt is too short, and you look ridiculous with that amount of makeup on your face,” she stated, before smiling and adding, “Perfect!”

I giggled in a very schoolgirl like fashion, and took a seat, being careful not to flash my knickers too much.

Stacy is in equally bazaar attire. She was wearing a fluffy towelling dressing gown over the top of satin pyjamas and a pair of moccasins on her feet.

“Are you sure you want to go ahead with this?” my mother asked, “This is the last opportunity to back out.”

“Having spent most weekends and all of the school holidays for the last three years living as a girl, I don’t think one extra day is going to faze me,” I replied.

“This is different and you know it. This will be the first time dressed in front of your peers. Even Stacy has only ever seen photos,” my mother responded with caution. “I’m still worried that this might not come across as a joke. You play the part too well.”

“I’ve already discussed this with the doc. I’ve been over the discovery scenarios and consequences many times. If my blackmailer really wants to expose me, then I would rather it happen on my terms,” I answer.

I was diagnosed with Gender Dysphoria shortly before by twelfth birthday. I’m currently fourteen. I openly admitted being transgender after my grandmother decided to buy me girl’s clothes for Christmas. It came as quite a shock but it served as the kick up the backside I needed to come into the open, at least to my family.

My ultimate aim is to transition and live as a woman. However, I’m in no rush and I’m not yet certain surgery is the solution. The thought of being chopped up doesn’t appeal, although neither does living as a man. I’m on hormone blockers to block puberty.

I spend around half my time living as a girl. I stay at my grandmothers during the holidays and I effectively keep my two lives separate. Those who know me here only see me as a boy, and I live as a girl when staying with my grandmother, so those living nearby never see me as a boy.

With the exception of family members, everybody else I know only sees one of my two modes. Only a select few know my secret. I’m able to live in both roles without detection, but I’m happier and seem more natural with a feminine presentation.

Unfortunately, one of the people at school has found evidence of me dressed as a girl, and is threatening to expose me. I have thought on many occasions about this scenario. I have kept my activities secret for fear of ridicule. I am a private person and don’t want the attention. However, there is no way I am giving in to blackmail. I would rather expose myself than give in.

I can be stubborn like that when I want to be. It was my stubbornness to wear the dress that Nan got me that exposed my desires in the first place.

Picking up our school bags, Stacy and I proceeded outside and climbed into my mother’s car for the drive to school. The reason for our unusual attire is that the school is allowing us to come in fancy dress in order to raise money for charity. It is the last Friday before half-term and normal lessons are going to end at lunchtime.

We have a normal school uniform, which for today only you can buy yourself out of wearing. If you are willing to pay double, then you can come in costume instead of plain clothes. Given that Halloween is next Thursday, I suspect a large proportion of any costumes may be based around that occasion. The only restrictions are that any costumes must be sensible and not interfere with your ability to participate in lessons. Mr Blobby costumes are banned.

I will be one of several St. Trinians pupils attending. I won’t be the only cross-dressed boy. The rugby team are apparently coming as American cheerleaders. Quite where a bunch large rugged blokes are going to find delicate looking outfits I’m not sure, but apparently they have.

I won’t even be the only boy in my class in a skirt. Scotty is coming in full highland regalia, including kilt. However, if anyone teases him about wearing a skirt, then they’re likely to receive a Glasgow kiss (that’s a head-butt if you are not familiar with the term).

Pulling up at the drop off point, Stacy and I got out and started walking into the school. I get a few wolf whistles as I walk past some of the boys. They are not people I know, and I smiled to myself as I wondered whether they realise I usually attend as a boy.

About a third of the pupils are in civvies, the rest are in fancy dress. I can’t see anybody not taking the opportunity to forgo the uniform. The current fashion seems to be to come dressed in nightwear, at least amongst the girls. Vampires seem to be a popular theme, and several of the smaller kids are in skeleton costumes. Most of the shops only supply costumes in little-kid sizes, so not many of my fellow students use shop-bought outfits. Halloween is less than a week away, so that has influenced a lot, but not all, of the costumes. It’s Friday the 25th with Halloween next Thursday. It’s the last day before the half-term break.

Our headmaster, Mr Faraday, was stood in the entrance with several other teachers, inspecting outfits to make sure that nobody has gone too far. We have already been warned that anybody going over the top will be asked to change, and anybody using this as an excuse to be sent home will end up in detention. Turning up as a Teletubby would not be tolerated. All the male teachers are also in fancy dress, mimicking stereotypical Victorian schoolteachers complete with mortarboards and canes.

“Good morning ladies, what have we here? Stacy, I see you got up late this morning, don’t panic you’re not the only one,” Mr Faraday said smiling. He doesn’t do much in the way of teaching, but we do have him for one lesson a week for general studies.

I know him on a more familiar basis than my classmates as he is one of only two staff members, the other being the school nurse, who knows about my medical status. I don’t fancy the stress of transitioning while at school, but if my secret should leak out, then I may change my plans. It is already getting to the point where it is becoming increasingly difficult to hide the physical changes, or lack thereof, of not going through male puberty.

“And an exchange student from St. Trinians,” Mr Faraday continued, “I don’t believe we’ve met, I’m the headmaster, Mr Faraday, and who might you be?”

I can see he’s trying to place my face, obviously recognising me to a certain extent, but unable to figure out my identity.

“I’m Emily, Sir. Emily Bridges. You may know my cousin Nathan,” I say with a wink and watch as his draw drops for a moment as he works out who I am. He knows I live part time as a girl, but has never seen me en femme.

He quickly recovered, “well welcome to Lakeside High, I hope you have a good day. Your skirt is shorter than regulation length, but as it’s your first day, I will let it slide once. Good day ladies.”

He then excused himself to go intercept a student arriving in a full suit of armour. I know Steve and he was talking about coming clad as a knight in shining armour. I happen to know the costume he has on is only to wind up the teachers. There is no way he can possibly sit down in what he is currently wearing. He has a tamer version consisting of chainmail that he’ll be dressed in for the rest of the day.

Heading inside to registration, I got a few more wolf whistles as I walked the corridors. I get a few raised eyebrows and double takes from a few people who know me. Only a select few people knew I was planning this, and only Stacy knows the true reasons, so it’s a surprise to most.

To confuse our classmates, I swapped seats with Jessica. She came dressed in Jedi robes and had her head covered in a hood. We have the same hair colour, so we decided to see how long it would take everybody to notice.

We took our seats at the front of the class. We were some of the first to arrive and everybody filed in behind us. I kept my back to everybody, hiding my identity. Stacy sat on a table facing backwards and gave me a commentary of what was happening behind me.

Mr Jones, our form teacher, came in and took his place up front. Everybody settled down and he started to call the register.

“Jessica Anderson,” he asked, looking in my direction. I had my head down looking at the desk, so he doesn’t have a direct sight of my face.

“Here, Sir,” Jessica called from my usual spot, dropping her hood in the process. This caught everybody off guard, as they had all assumed I was sitting in my usual seat. I could hear some murmurs, and Mr Jones immediately called for silence.

“Nathan Bridges?” he asked, looking back in my direction in puzzlement.

I smile and answer, “Here, Sir,” in the most sexy voice I can manage. I blew him a kiss. The room erupted into a mixture of laughter and wolf whistles.

“Dude, you are so gay!” Robert calls out to me.

“One hundred percent lesbian and proud of it,” I replied, smiling.

Technically we are pushing the boundaries of the schools zero tolerance approach to homophobia and bulling. However, it is widely known that Robert lives with his gay farther and his partner. They were the first couple in our town to take advantage of civil partnerships when they were brought in. Given his home circumstances, he is one of the few people who can get away with such a comment in jest.

He is also dressed as a fairy, complete with home-made magic wand. He had on a white lacy dress with and a pair of wings fashioned out of paper and garden wire. Robert is very tall, almost six feet, but also skinny. It looks the dress is probably one of his little sisters old party dresses as it appears to be made for a six year old. The dress, which looks to be designed to be loose, is very tight on him, but does fit. It is however nowhere near long enough and the bottom of what is presumably supposed to be an ankle length skirt barely covers his hips.

Our teacher got everything rapidly back under control, and after congratulating me on my costume, continued with the register.

We have just finished when the speakers in the ceiling crackled and Mr Faraday’s voice filled the room. “Good morning students, and welcome to a fun packed freaky Friday. I hope you are all in the mood for raising some money for Children in Need."

We are a bit early in our fundraising events as the main televised event isn't for another three weeks. However, it was decided the last day before the break was the less disruptive time to stage the fundraising.

"I have a few announcements to go through. Firstly, there are a number of students today who are cross-dressed, both boys dressed as girls and a few girls with fake beards pretending to be boys. As this could cause confusion and embarrassment, the two bathrooms opposite the music room have been designated unisex for today. Any student can therefore use either bathroom, irrespective of their actual gender. So if you decide to use these bathrooms, please bear this in mind.”

I smile at this announcement. I wasn’t sure going into the girls bathroom would be a good idea, and I was worried that I might get a bit of opposition from boys not realising I’m male. What I’m wearing would make using the urinals awkward, not that I ever use them anyway, preferring to sit. Normally in girl mode I wouldn’t think twice about using the female facilities, but there is a high chance of being spotted by someone who knows I’m male, although I doubt anybody else would notice.

“This was requested by the Rugby team as they are all dressed in mini-skirts and tights and felt it would be easier not to have to use the urinals,” our headmaster continued. “Speaking of which, and I never thought I would ever have to make such an announcement, I have been asked to tell you that any adventurous girls who would like to try out using the urinals are welcome to do so and that sixth former Mary Brown will be outside the music room selling aides to facilitate this. For those of you who don’t know her, she will be dressed as Florence Nightingale in a Victorian style nurses uniform.”

This causes a few murmurs to go round the room. I know several girls who are extroverted enough to take that option, even if there are boys stood beside them. I think I will be using the girl’s unisex bathroom if the need arises.

“Lessons will progress as normal until lunch time. After afternoon registration, there will be the elections for the student councillors. I hope that all nominations have been made, seconded and accepted. There will be opportunity for short presentations by candidates, in the form of a debate, before voting will take place,” the tannoy crackled as he continued to speak.

This is where my day could get interesting. Somebody is trying to blackmail me into standing down from the election. I do not intend to do so. Therefore, I will wait and see what happens.

“This will be followed by a number of charity related activities instead of normal lessons, although I will warn you they are designed to be education,” a groan went round the room as the headmaster announced this. “Please study hard this morning, and then have fun this afternoon. That is all, thank you.”

Mr Jones came round the class collecting the uniform buyout money, finishing shortly before the bell rung for the first lesson.

The morning progressed as normal, despite everybody being in weird clothing. I get some strange looks by my classmates, and teachers, but nothing too nasty. I’m accused of being girly and a sissy, which I simply acknowledge and agree with. After all, as I am cross-dressed in a miniskirt, both statements can be considered accurate.

At break time, I find my classmates in the canteen. I know Stacy is conspiring with some of the girls to drag me into a very feminine discussion on the pretence of trying to embarrass me. We both know it won’t, but instead it will be an opportunity for me to simply fit in as a girl, even if for a short time.

A couple of the girls, Charlotte and Mary, attempt to embarrass me by discussing feminine hygiene, but I don’t take the bait. Instead, having an idea this might happen, I have a couple of questions to hand that turned the situation around. The conversation was quickly moved onto safer grounds, much to my and Stacey’s amusement.

We end up discussing makeup, and in particular how the style I’m wearing would work well for me if it was toned down to less extreme measures. I did the job myself, but don’t take credit, saying that I had help from my mother.

Half way through the twenty minute break period, I tell the other girls I need to visit the bathroom, and get up to go to the girls toilets near the music room that have been designated unisex. What surprises me is that some of them decide to tag along and also use the same toilets.

I’m not surprised at Stacy, as she partially sees me as a girl anyway, even though I haven’t dressed as myself in front of her. It is Jessica and Janet who catch me off guard and it is a somewhat surreal experience carrying on our conversation as we relieve ourselves in adjacent cubicles.

This isn’t a new experience for me, as I have used female bathrooms on a number of occasions, including several times with girls my own age. My friend Jennifer saw to that.

Jennifer lives next door to my grandmother, and we became friends when I stayed over the summer while my parents both worked. This was one of the first times I was truly able to let my usual guard down and be myself instead of hiding.

My grandmother had told me that a girl had moved in next door, and I had seen her arrive home from my bedroom window while unpacking the afternoon I arrived.

Each day I would take a book and sit in the small park down the road. After a fortnight of seeing me come and go, she came into the park with a couple of her friends. Jennifer introduced herself, saying she had seen me leave my grandmothers, and assuming correctly that I must be staying with her over the summer and I probably didn’t have any friends here with which to socialise. I deliberately introduced myself by the gender neutral nickname of Biscuit, and refused giving my name saying it was embarrassing.

I didn’t try and deceive them, but neither did I correct their assumption that I was another girl. I had grown my hair as long as I dared, and had put in a ponytail, slightly too high for a guy, but not quite as high up as a girl. Combined with the white t-shirt, khaki shorts, white sports socks, and white trainers, I looked more like a tomboy than a male, but not enough, at least I thought, to raise suspicion in my grandmother.

I had spent most of the day with them, and for that short time I was fully accepted as one of the girls. Luckily on that occasion, I didn’t need to use public facilities, as we ended up back at Lucy’s house for lunch, and ended up playing twister in her back garden.

I was so relaxed by this point that I didn’t even consider the dangers of close body contact combined with the possibility of someone looking up my shorts, given the unusual angles we were contorting ourselves into. Not that they would have seen much, as I was wearing plain white tight underwear that did a good job of holding me in. It wasn’t until we all landed laughing in a heap on top of each other and Natalie’s elbow ended up perilously close to my crotch did I realise how dangerous the situation was getting. I very much doubted the girls would have knowingly let a boy have such close contact.

That sobered me up and made me realise I needed to extract myself from the situation very carefully. Unfortunately, I didn’t have the opportunity. Half an hour later, Jennifer’s mother, Juliette, came to collect the two of us, and regrettably, my grandmother came along for the ride. I had phoned her to let her know where I was, and obviously on learning I was with Jennifer, had spoken with her neighbour.

I knew as soon as I saw them step out into the back garden I was in deep trouble.

“Sorry to break up the fun girls and boys, but it’s time for Nathan and Jennifer to leave,” Juliette stated, looking round in puzzlement trying to spot a boy amongst the girls in front of her.

Any hope of keeping my secret vanished in a puff of smoke, as all eyes fell on me. All the other girls knew each other, so as the only newcomer, I was the logical candidate, especially as I had refused to tell them my real name.

I tried to act nonchalantly, replying lamely, “well I did say I have an embarrassing name.” I couldn’t look the girls in the face and, and despite the warm late afternoon sun, there was a distinct frostiness in the air.

Jennifer quickly said farewell to her friends, while I tried to sink into the shadows. We travelled the short five minute drive back home in silence.

The next few days I spent moping about the house in a state of depression, angry with myself for being so stupid. While I could potentially ignore the other girls, it was difficult to avoid Jennifer as she lived next door. She eventually dragged me outside again and I ended up spending time with her and the other girls, but the initial magic had gone.

They continued to call me Biscuit, but now that they knew I was a boy, they were a lot more reserved in their behaviour towards me. The conversation steered clear of any feminine topics, and there were no activities suggested that would end up with further close physical contact. I also withdrew back to my shyer introverted male persona.

It was Jennifer who brought me back out of my shell, although I didn’t realise it at the time. While the others seemed to distance themselves from me, she continued to treat me as a girl, and openly talked about subjects her friends seemed reluctant to include me in.

Gradually, I had started to feel more at ease with myself, and by the time the holidays were up, the other girls were starting to warm to me.

I didn’t become aware how good a friend she was until Christmas time. She spent a lot of time with my Grandmother, and did her garden for her during the autumn, taking over from me after I went home. She also helped her learn how to use the computer she had bought. It was while helping to recover some lost files that Jennifer found out my grandmother was researching transgenderism. She looked in the browser cache to find a file my grandmother had attempted to save, and found some of the pages she had visited on the subject.

The two of them then discussed my girlishness and conspired together to try and bring me out of my shell. Jennifer helped my grandmother pick out a dress as my Christmas present, setting me up for a shock on Christmas day, and the catalyst for coming out.

I started to live part time as a girl, when staying with my Grandmother. I didn’t have the confidence to dress in public as a girl near home. I was so much happier presenting as a girl, and I was soon included back into her circle of friends as a girl. Only a select few knew my secret, basically the ones who were present that first day. The rest of the girls I met never knew or realised what I was.

I ended up going on many shopping trips with them, and using public restrooms, both with girls that knew about me and ones who didn’t. The last time I spent with Jennifer and Lucy was a couple of weekends ago, picking out the very outfit I am now wearing.

I never thought that I would be sharing bathroom facilities with the girls at school, as I never intended any of them to see me en-femme.

I don’t have many close friends, having always been an outcast. The closest friend at school is Stacy, and that is mainly because we live next door to one another. We have been close friends since were toddlers, and she is the one person who I have always let my guard down around.

I only started to form a protective shield around myself after starting school. I was picked on by some of the kids for being girly. I never really considered my gender until primary school. I knew I was a boy, and that boys and girls where physically different, but only started to learn about the social norms of what girls and boys should like when going to school. It was then that I started to realise I didn't quite fit in with what was expected.

I soon realised it was a bad thing to advertise my girlishness, so learned to put on a masculine charade around other people. Over the years we had remained friends, but we had drifted apart slightly due to peer pressure.

Stacy was a popular girl, and although she didn’t really take notice of my gender, other girls did. They weren’t comfortable having a boy around, and I didn’t want to make Stacy feel awkward by forcing her to choose between her other friends and me. I therefore withdrew myself further into my shell, only daring to let myself out when alone with her, something that happened less and less as the years went by.

I hadn’t realised how depressed and isolated I had become until I came out. The more I opened up, the more I found it hard to present as male. However, I was still too scared to be myself at home, except on special occasions. Too many teens in my neighbourhood go to my school, and although I wouldn’t have a problem with Stacy knowing, some of the other girls nearby I can only describe as spiteful little bitches, and I have no intention of letting them make my life hell.

After my initial coming out, we kept my problems in the family, and it was the difficulty that my parents had not to slip and use the wrong name or pronoun that made me decide to separate my lives in two. Jennifer and her circle of friends, although they know I’m Nathan, they’ve never used that name, and for the most part, hardly ever used male pronouns. I was always Biscuit or Emily round them. It’s therefore very unlikely that they would be likely to slip up, so I could be myself without too much risk.

I didn’t want to risk my secret being revealed, and although I trust Stacy, I had to be sure that she wouldn’t accidentally out me.

I had come to an agreement with my parents to use my nickname for the most part, as this was gender neutral, and wouldn’t cause problems. Stacy picked up on my new nickname, having explained it was given to me when staying with my grandmother, but not going into details. At my request, she started to refer to me by that name, but it took her several weeks to get used to calling me Biscuit rather than Nathan.

For safety I decided not to tell her my feminine name, under the principle that if she doesn’t know it, she can’t accidentally use it.

Unfortunately I made a complete balls-up of keeping my lives separate, accidentally bringing Stacy in on the secret.

About four months ago, we were both sat working on some homework in the dining room at my house. Although we spend time in each other’s houses, we don’t tend to go into each other’s rooms. It’s not so much our parents are worried what we might get up to, it’s that I don’t want Stacy in my bedroom where she could accidentally see some of my girl clothes. Although I tend to only wear unisex or male cut clothing, I do have a few feminine items at home.

As Stacey doesn’t come into my room, I don’t tend to go into her room if I can avoid it.

We were both working on laptops. Both our houses have wireless internet, and the properties are close enough together that we can both use our own broadband connections. I needed to send some files across to Stacy, and the easiest method was via email.

As I have two identities, I have two email accounts. Needless to say, I managed to accidentally open the wrong one, and it wasn’t until Stacey asked why the email she had just received was from someone called Emily, did I realise what I had done.

In retrospect, I might have been able to talk my way out of the situation if I hadn’t spent the next few minutes swearing and banging my head against the desk. That clued Stacy in to the fact I’m deliberately maintaining two online identities.

At first I told her to ignore it and forget about it. However, Stacey wouldn’t take that for an answer, and every time she thought she could get away with it when nobody was listening, would call me Emily, even when at school.

After a week of nagging, I caved in and admitted I live part time as a girl and possibly spend the rest of my life as one.