Boys Will Be Gurls 2.0

Please note this chapter largely builds the world and Harriet's journey, I still think its worth a read. But Harriet's adventures will continue in further chapters

***

I woke up the next morning a little groggy, I hadn't had much exposure to alcohol before and wasn't enjoying the after effects. For a second I didn't remember what had happened the night before, then it all hit me in a rush.

I had dressed up like a girl to be my best friend, Will's, date for the dinner, one of the other boys, Charlie, had flirted with me and we had danced together. We had ended up grinding on the dancefloor and had both got excited, running off to the gardens where we had kissed. But the pièce de résistance was that I had wanked him off, letting him cum on me before he raced off back to the dinner.

I lay back on the bed, the most surprising thing about it was that I didn't care, in fact I had enjoyed it and was oddly proud of having made Charlie cum. I vividly remembered the sensation of his hard cock in my hand, the feeling of it pulsing when he came, the sight, the smell and taste of his cum.

I was starting to get excited, my own dick stirring in my cum stained panties, I chuckled, oh yeah, and at some point during all of that I had been so turned on I had cum without even touching myself.

I ran my hands down my body, and began gently rubbing myself through my panties, not wanking, not yet, working up to it, slowly. Unlike with poor Charlie, I wanted to take my time. I laughed to myself, poor Charlie, he had cum like a geyser even if he hadn't lasted long, maybe next time...

I stopped, there wouldn't be a next time, Charlie had gone to the garden with Harriet not Harry. And Harriet didn't exist, not really. That might be the only time I got to be Harriet, the only time I would do THAT...

It was just as well, I had stopped touching myself, because the door to my room swung open and Will barged in, red eyed and pale, he plonked himself down on the bed next to me as I quickly rearranged the covers to hide my panties and my erect cock.

"Oh man, I feel rough? Do you remember what happened last night? I woke up on a bench downstairs."

Not waiting for me to reply, Will levered himself up and started going through my bedside table.

"Have you got any headache tablets? I think I'm dying"

I lay back, Will was such a dick sometimes.

"Yeah, second draw I think."

He found them, downing a handful with a swig from the glass on the table before lying back on the bed, next to me, but on top of the covers. He looked around the room, surveying the devastation, there were clothes everywhere and in the corner my vintage green dress, even from across the room I could see the stains on the front, hopefully Will wouldn't notice.

"So did it work?"

He wasn't even looking at me, he was laid back with his eyes closed, probably nursing the mother of all hangovers.

"Seems so, though I'm not surprised you don't remember."

He didn't answer for a second. "I'm guessing I got really drunk and was a complete dick."

I uh-huh'd

He sighed, "Sorry dude, I know you really... what you did, I'm really grateful, sorry I wasn't more appreciative."

I smiled, "You're welcome... dickhead"

We both chuckled.

"Harry?"

"Will."

"Were you wearing panties when I came in?"

I coughed, "Yeah, I was too smashed to take them off last night."

Will chuckled, "That's so gay."

I hit him with a pillow.

***

The next couple of days were surprisingly normal, back to the routine of before. I went to class, hung out with Will, went to the various clubs I was a member of. In drama the teacher asked me if I'd seen a wig that had gone missing, a brunette one with a short pixie cut. I had, it was still in my room, but I couldn't tell him that so I lied.

Then the dinner caught up with me, I was given a message in Math class, I had to go and see my housemaster, Mr Stepleton.

Mr Stepleton had intercepted a parcel I had ordered, it had contained my bra and panties, but I had paid for it with Will's card so it had been addressed to him. When Mr Stepleton had spoken to Will about it, he had dumped it on me, saying I had borrowed the card and he didn't know what was in the parcel.

I was stood outside his office waiting for him, understandably nervous, was i going to be suspended? Expelled? Would he call my parents?

He came up the hall, carrying a pile of papers, he was a tall man, probably around 6', he towered over me, he was a big man, quite fit he coached the school rugby team, but was carrying a little extra weight, he shaved his head to hide the fact he was going bald and always seemed to have a 5 o'clock shadow. He had rolled his sleeves up, but still had on a tie, he looked like he should have been a farmer rather than a professor.

However, the most noticeable thing about Mr Stepleton was his voice, it was deep and he spoke with a slow yorkshire drawl, it was a calm voice.

"Mr Cabot"

My name is Cabot, Harry Cabot and at my school everyone is a Mr.

I stood up straighter "Morning Sir"

"Settle down, you're not in trouble, just let me get in my office and we can get started."

He juggled his pile of papers so he could get his key and open the door, leaving it open he dumped the papers on his desk, gesturing to a chair as he made his way round to sit in his own.

"Now Harry, this is... well it's..." he looked up, directly at me "a bit fucking awkward."

All the boys like Mr Stepleton, he treated us like adults, he could be hard but was fair, it was odd that one of the strictest teachers was also one of the most popular.

I nodded, not wanting to speak in case I incriminated myself.

"I expect Mr Hythe" that was Will "has informed you I checked a parcel addressed to him the other day, that apparently contained items for you."

"According to Mr Hythe you ordered the items with his card, with his permission."

He was looking straight at me

"Is this true."

I didn't answer straight away, I couldn't think of what to say.

"I'll rephrase, is Mr Hythe selling me a pack of lies and should I be dragging him in front of the Head?"

I swallowed, my mouth suddenly dry "No, Sir."

He raised a hand, "You're not in trouble, the... items aren't prohibited, they are just... unusual."

I hung my head, not wanting to look at him

"Harry look up." I raised my head but couldn't look at him "Harry, I want to be having this conversation as much as you."

I managed to raise my gaze to look at him, he wasn't angry or disgusted just a little embarrassed.

"I just need to know if you are ok?"

I nodded and he smiled "There, progress. Do you mind if I ask you some questions?"

I gulped slightly but nodded.

"I'm assuming from your reaction to all this that the items are for you."

I nodded.

"How long have you been wearing women's clothing?"

I didn't know what would be the best thing to say, so I was honest.

"They were the first things I got Sir."

He nodded as if that made sense, "Okay, and forget the Sir for now. Why did you use Mr Hythe's card? Does he know?"

I thought about it for a second "I didn't have any money on mine so Will lent it to me but he doesn't know what I used it for."

He made a scribble on a piece of paper "Ok Harry, I'm just going to come out and say it, I'm a little worried about you and I have no idea what to do. I don't feel telling your parents would help anything."

I nearly leapt out of my seat, "So, I'm not going to tell them, but I want to make a deal with you."

I settled back in my chair and nodded, I felt like I had been nodding a lot. "I want you to talk to someone, let them know how you are feeling?"

I nodded again, "OK."

"You can talk to whomever you want, if you want to talk to a member of faculty I can set it up for you."

I piped up "Can I talk to you?"

He seemed taken aback, but he nodded. After a moment he spoke.

"So Harry, how have you been feeling?"

And I told him, I started off talking about dressing up, how it made me feel, how much I enjoyed it, then I told him about the dinner, I didn't tell him why I had gone with Will and he didn't ask, but I told him about Charlie, though I didn't use his name. I told him about the feelings of shame and how they had stopped.

He didn't interrupt, he just sat there listening all the way through. I talked for ever, I hadn't realised how much I had needed to share, to unburden myself of all that had happened. We arranged that we would have regular meetings and I would keep him up to date. When I was leaving, he asked me on question.

"Are you wearing panties now?"

I nodded.

***

My chat with Mr Stepleton had made me feel much better and I resolved that while Harriet couldn't come out and play, I could dress in private.

Because I was part of the drama club, I had a key to the drama room, so I moved most of my supplies in there, I put my stained green dress in with a load of costumes so it wouldn't look odd and took them to the laundry room.

I had thought about throwing it away, but in the end I couldn't. I couldn't wear it, the rooms didn't have locks and privacy was a pretty foreign concept, there was always someone, probably Will, would walk in, but the drama room had a lock and was deserted most nights. So I started going there to dress, even doing my makeup and wearing a wig. It became a routine over the next few days, always ending the same way, with me cumming thinking about Charlie and the garden.

I saw Charlie around school, the first time I felt myself go bright red and I was terrified he would recognise me. But after a couple of days of trying to avoid him I got over it.

He barely knew who I was and it was a small school, I couldn't avoid him. That and I was so preoccupied with sneaking around trying to avoid him, I had turned a corner and walked straight into him.

I had frozen waiting for the flash of recognition, for him to realise, but he didn't and I felt pretty safe he wouldn't.

While I had been avoiding Charlie, Will had been avoiding me.

That was probably a bit harsh but he was suddenly a lot busier now, actually producing a "girlfriend" had catapulted him to near celebrity status.

For someone who was so bothered about what everyone else thought of him, he was finally getting to live his dream of being popular.

Nothing really changed for a couple of weeks, I would still chill with Harry sometimes, but spent time whenever I could alone in the drama room. But one evening, I was with Harry, playing on the xbox. One of the lower years was using the drama room and I was a bit frustrated at the break in my new routine, not really focusing on the game.

"Did you hear about what happened with Sean?"

Sean was a boy in our year, he had been at the dinner, but I hadn't really noticed him other than he was one of the few boys that had brought a date.

"No, what happened?"

"At the dinner, he got caught in the garden by a teacher."

My ears pricked up, apparently I hadn't been the only one to use the garden.

"Caught doing what?"

Will shrugged, paying more attention to the xbox than the conversation.

"Don't know, but he was with his date."

Will is a gossip but I'm not normally interested, except this was different, the idea of another couple doing what Charlie and I had done aroused my curiosity.

"Tom said she was sucking his dick, when they were caught". Will carried on

It sounded like they had gone further than me, and I couldn't help imagining what it would be like to have a penis in his mouth. I had thought about it a few times since that night, during my sessions in the drama room.

I waited for him to carry on. This was pretty big as far as school gossip went.

"So?" I prompted

"So, what?"

It turned out, Will didn't know anymore. Except Sean is a lucky SOB and he wished he had a girlfriend to suck his dick.

A little bit of me was jealous, like me giving Charlie a hand job had been upstaged by Sean.

In truth I wasn't sure who I thought was luckier, Sean or his date and I wondered what it was like to give a blowjob...

***

The next day at lunch, I sat with some of the athletics team after practice, unsurprisingly, conversation turned to the newest gossip and just what Sean had been up to. Most agreed that he had been getting head, some called bullshit on the entire thing, or said they were probably just making out and the conversation moved on, to the "fittest" girl at the dance. I was only half listening, pre-occupied by my memories of the night, until I heard my name, except not MY name, Harriet's.

"Tell you what, I'd pick that Harriet, Will Hythe's date. She was nice."

Tony, one of the sprinter's chimed in, followed by one of his friends, guffawing

"Nice?!"

Tony grinned, saying "well she had a nice arse and blowjob lips."

Everyone laughed, but I was stunned, he was talking about me, about my arse, my lips. I was so preoccupied I missed my name being called.

"Cabot?" I came to, Tony looking at me, "You're mates with Will, you know Harriet?"

I shook my head, hoping I wasn't going too red, "Not really, I've only seen her a couple of times."

The conversation moved on again, with me sinking into the background. After a few minutes I made my excuses and left, most of my food still on my plate.

I was shocked, I know Charlie and I had messed around but I hadn't exactly thought of myself, even as Harriet as an object of sexual desire.

That night I stood in my room, looking at myself in the mirror.

I did have full lips and I'd always had strong legs from athletics but I'd never really thought about my bum.

***

That night I went to the drama room, and I looked at myself in the mirror, I did have full lips, and I knew I had strong legs but I had never really noticed my bum. I got dressed and did my makeup, putting lipstick on my "blowjob lips" and admiring my "nice arse" in my dress.

It was a rush, knowing that I, even if it wasn't really me, was desired and that people lusted after me. I hiked my dress up, feeling how hard I was in my panties, rubbing myself through the soft fabric, my lips parting as a slight moan escaped.

I closed my eyes, imagining the dinner again, but this time everyone watched me, lust in their eyes, their gazes devouring me, following my every movement as I danced, first with one, then another, wanted by everyone.

I pulled myself out of the panties, gently moving my hand up and down my shaft, imagining as each new dance partner got closer and closer, touching me, caressing me, grabbing me. Until I was in the garden, kissing and being kissed, my hand moving faster now as I imagined, it touching him, first through his trousers, then bold, drawing him out, his impressive hardness bobbing in the air.

I grasped him, moving my hand to and fro, slowly, exciting him, pleasing him until I could feel him pushing me down, not forceful but insistent, as I fell to my knees, staring at his cock as it throbbed in front of my eyes, pausing only for a second before taking him in my mouth.

In the drama room, my hand moved faster, my other hand moving up without conscious volition, my mouth opening as I gently slid two fingers into my mouth, my imaginary man, my tongue dancing around him as I imagined.

I could feel his warmth in my mouth, even as I felt his hand on the back of my head, encouraging me. I knew he couldn't last long, he was too excited, too turned on, so I picked up speed, moaning softly.

I came with a spurt, just as in my mind he thrust forward, exploding in my mouth, afterwards, I lay spent, my chest heaving slightly as I breathed, my heartbeat fluttering. I brought my hand, still covered in my own semen to my mouth, and licked it off, imagining the liquid in my mouth had come from someone else.

Every time I came to the drama room I imagined it was Charlie, just like that night, but tonight it wasn't, it was Tony, my teammate, who fancied Harriet. I wondered what that meant, but was too tired to care. I carefully removed my makeup and got changed back into my normal clothes, slowly walking back to my room and fell asleep dreaming of Harriet.