DWB

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E.W. finds herself where she least expects it.
69.1k words
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Part 1 of the 4 part series

Updated 06/10/2023
Created 03/11/2021
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A starlet's descent on her own terms. Becomes what she thought she hates, and learns to love it.

This story wrote itself. I just happened to type it out.

There are a number of things you'll have to suspend disbelief for...and depending on the degree to which you might focus on such things include anachronistic technology, some timeline issues in terms of films, and the wrong haircut for the age of the starlet in this story. But fuck it, it's my fantasy, and apparently that includes easy casting of images to the telly, and short hair. Also, I am not English and as such may be out on describing a few things -- drinking laws, school, Black Cabs etc. My apologies to the Queen and her subjects.

Lastly, to the actual person in question, please consider this as an expression of, albeit misguided, admiration. Apologies if needed. No offence intended. Genuinely.

Other than that, enjoy, if this is what you're into.

Chapter 1 (of 10). Endorphins.

The day after my 18th birthday saw me lying in bed nursing a truly epic hangover. The kind that wipes out not just the morning after, but the rest of the weekend. For I had been out on the town the night before with friends as we celebrated my entry to official legal drinking age.

As I lay in bed with an encroaching thunderous headache, I tried to recall the previous night's events. They were a haze of shots, beer and, worse of all, cigarettes. Simply put, I was one ill-advised move away from bringing my guts up.

As a standard-issue male I had awoken with the usual morning erection and was lying on my stomach with it pressing into the mattress, finding solace in the mild pleasure it elicited, trying to get it to overwhelm the otherwise awful feeling permeating my poisoned body. I kicked off my boxers and rolled onto my side, and grasped at it to heighten the useful sensation. In all my not so many years I had learned that the best hangover cure, if only temporarily, was to be as turned on as possible, for as long as possible. Endorphins are the world's true painkillers. And I had nowhere else to be that I could think of...

I rolled onto my side and grasped and stroked my cock slowly, hazily thinking of all things erotic, and trying to zero in on whatever thing it might be this time that would get me to where I wanted, no, needed, to be.

We all have that Rolodex of sexual fantasies mixed with wistful memories to file through. The girl at school with the cutest smile, the female actor that is somehow more beautiful than all the others, the porn video that is so erotic, or fucked up, that it's beyond your prior comprehension. I licked my hand to give my dick some slickness as I filed through all these images in my mind's eye. Sorting, re-sorting, combining and finding new variations on the theme, which was basically them doing anything and everything with my cock, and me doing anything and everything with their every orifice. Don't pretend as though you are any different!

I considered for a moment whether or not I shouldn't get my laptop and get some real images to work with, but my hungover state told me 'this is all you can manage right now fella'. So I closed my eyes and focussed intently on the task at (in) hand.

At some point I was slightly pulled from my masturbatory reverie when I heard sounds outside my door. Clearly the rest of the house inhabitants were awake and going about their day. I assumed absentmindedly that they would leave me be, given they knew very well how big my night last night had been.

But I assumed wrong it would seem, because at that moment I heard the door to my bedroom fly open.

'Hey B. How you feeling?!' Came the voice from the other side of the room. It was M.

The first word about M. This was her house. Her family's I mean. I was just staying here. Although I had been for almost a year now. I was a family friend that had come to London from the Midlands to finish my schooling, at a much better school than the one in my home town. M and I were in the same year, but rarely had any classes together. Nor did we share friend groups, and so we didn't really see much of each other it must be said, for reasons that will soon become clear. The point is that our relationship up until that point was purely, and entirely, platonic. That's right. Look it up. It's an actual thing, despite all supposed evidence on this site to the contrary.

Now as to the B...my name's Will, but in our years growing up together that has variously included nicknames such as Willy, Billy, Bill and one particularly annoying summer, when The Black Eyed Peas were big, W.U.R. as in Will.I.Am made into Will.You.Are. M liked playing with words you see. It was rarely welcome, and only sometimes clever enough to tolerate. Anyway she settled eventually on B, I think because Billy was an especially not favourite of mine. That and in the family I was sometimes referred to as the 'Other Brother'. Which one of those she had in mind when she said 'B', to be honest these days I wasn't quite sure.

I just called her M.

'Better than that big grimace on your dial I hope!' she continued, rubbing it in.

My eyes opening blearily was all the reaction I could manage. I was on my side and under the covers so I knew it would not be obvious what I was doing under there. I hoped the vague smell of my wanking was similarly contained.

Obviously she was feeling much more chipper, despite her having also attended the night before. In a strange coincidence, it was her birthday today, not that I'd quite twigged to that fact quite yet. Fortunately the local pub hadn't made a fuss over a day or so. Not for her anyway.

I rolled over and groaned in frustration, not at all happy at the intrusion.

'Not great. You?' Was all I could manage.

'Me? Oh I'm fine.' She replied cruelly. 'But you look like death warmed up. Hope it was worth it.'

'I'm not sure it was' I replied. 'Death would be a welcome reprieve.'

'I'm sure it would.' She replied, apparently indifferent.

'But we have a big day planned B, and you need to get up!' And with that she yanked my bed sheets straight off of me.

Fuck. I hadn't even had time to take my hand off my cock.

'Holy shit B, you could have warned a girl!' She hissed at seeing her 'Other Brother' lying prostrate, half naked, with his dick in his hand.

The angle was such that she couldn't actually see all of me, I was on my side and she was on the backside, as it were, but there was no hiding what I was doing, and in fact my hand was the only thing hiding anything!

Now exposed, I slowly realised that I couldn't seem to find the energy to even attempt to cover what I had been doing. I did try to pull my t-shirt down, but it really didn't go low enough to do anything useful.

'Fuck M.' I said in annoyance. 'Put it back. And sorry but it helps with the hangover. Endorphins.'

'Does it now?' She replied suspiciously. Not much of a drinker old, just now of age, M. Probably had never made that particular discovery.

'You could put the covers back, or look away you know.' I suggested. 'Or leave..'

'I suppose I could' She replied, 'But what's done is done....I've seen it all now. And time's a wasting...

'Come on upsy-daisy!' She said pulling on my foot, possibly exposing more of me in the process.

I resisted, meekly kicking her away, but instead merely managed to summon enough energy to roll over on my stomach.

'Oh you've decided to hide that now have you...Better late than never I guess'. M allowed generously.

'Still doesn't cover up everything though now does it.' She added, referring presumably to my bare arse.

I reached out in a feeble attempt to grab for the covers, M however, pulled them further away.

'Oh no.' She said, 'You're not going back to sleep, or whatever it was that you were doing under there...it's my day today and we've gots lots of things to do..!'

All I could do was groan in response. A moment passed and I imagined for a moment that she might have let me be. My brain went with this unlikely scenario and the old horny instinct kicked in and my hips thrust forward into the bed.

'Oh my.' Came the commentary from M. 'Quite the view from up here B.'

I just lay there, in my pathetic prostrate state.

A further word about M. She was an elfin young thing. Skinny, fine featured, beautiful really, not that I'd really thought about such things.

But you have.

You see it just so happened that M was none other than Emma Watson. Yes, that Emma Watson. No need to say anything more really, except to again stress that up until that fateful moment our relationship had been the epitome of normal. We were friendly, but not that close. She was busier than anyone else on the planet, and I was content enough living my comparatively normal life. We fought, and kidded and laughed at and with each other, almost as if we were actually siblings. Besides, while we may have gone to the same school, most of the time she was off filming and thus getting privately tutored.

Fame is a funny thing really. It's really not that impressive up close. In fact most of the time I was outright glad that I never had to deal with any of the shit that she had to. Of course as a male, I suppose at least some of the more dirty aspects of the overwhelming adulation would have been a bit more welcome. But all in all, I think I pitied her more than envied.

Anyway, back to the issue, at...hand.

My severely post-drunken state meant that I lacked the ability to move, so I turned my head slightly and finally looked up at her. What met my bleary eyes was the sneaky little shit M, holding her phone and thus camera in front of her. I heard the shutter sound go.

'That's going straight on the mantlepiece.' She giggled. She was a mischievous young thing when the mood took her. What I heard next was worse. The filming tone sounded. Evidently, she had begun filming my faintly thrusting arse.

'Come on M. Turn it off. And delete.' I commanded wearily, pleadingly.

'Not on your willy, Willy.' She replied. Word games.

'Nice bum by the way. All those sports are paying off B...my gal friends will love this.'

'Give me that.' I mumbled irritably and with meek desperation.

'Oh no I don't think so.' She replied gleefully. 'This is the best present I could hope for...think of the things you'll do for me now I have this on video!'

I didn't really know what to think of that. Again, just to reiterate, M and I weren't really that close. I was outgoing and sporty, she was more the bookish type (yes really), with a few close friends that tended to stay in more than attend all the various childish drunken parties I went to. Even last night as I held court at the bar, she was squirrelled away in a corner booth, watching on quietly.

'M, I just need another half an hour ok?' I pleaded.

'So you can finish what you'd started when I came in?' She replied. 'That's too long I'm afraid.'

'M I'm too hungover.' I pleaded again, 'Why don't you go start your day and whatever you've got planned and I'll catch you all up.'

'Sorry B, you're crucial to my plans I'm afraid. You sure don't look great though.'

'Thanks a lot.' I replied, slightly offended.

'I meant your complexion little miss sensitive. You're almost as white as your sheets.'

'I just need a few more...years sleep.'

'You weren't sleeping when I came in.' That, I could hardly deny.

'Endorphins.' I repeated my excuse.

'So you say...' she replied curiously. I could hear the cogs in her mind whirring.

'Alright B. I am a practical gal, when it's called for...I have a suggestion, a request if you will. One that benefits us both. You can finish what you started, and I can get you moving so we can start what is supposed to be my special day after all.'

I managed a vaguely curious groan in response.

'You need to...erm, cum...and quickly, and I, being a curious-minded individual, would rather like to see how that all works...'

That got my attention. Firstly, that I'd certainly never heard her say the word 'cum'. And secondly what on earth was she talking about I thought, getting a little impatient with this intrusion into my very exclusive hangover.

'What?' Was my rather curt, disbelieving reply. 'Come on M can you just leave me be please?'

Now given that you know who this girl was or is, you might think it mad that I would say and feel such a thing at this point. But you need to remember that I had, up until now, perfectly normal 'other brother' relations with this person. We didn't talk about sex, there was no undercurrent of sexual awkwardness, we respected each other's privacy and so on and so forth. So for her to be seeing me naked was already too much, and for her to suggest watching me wank was frankly, quite beyond the pale, of my bare white English arse cheeks.

Unfortunately for me though, even on my best day, she was smarter than me, and today she had all the possible angles covered it would seem. Pun intended.

'Oh you need convincing?' She said, her argumentative prowess rising to the challenge.

'Alright then. Firstly, I'm still filming. I have photos, and footage of you naked, and with your...cock in your hand.'

Cock! Another first.

'Now I could keep this, and, carefully edited, share this with anyone I wanted. Anonymously even. And everyone would see. Or, if you do what I am suggesting then I could delete it and your pitiful hungover little wankathon would just be our little secret.'

So it was blackmail then.

It was at that moment, as if to heighten the point I heard my wall mounted telly turn on. I looked over at it and saw a, my, half naked form lying on a bed, from her perspective. She was chromecasting the fucking thing!

'Check out that framing!' she remarked cheekily, my butt cheeks front and centre.

'Aw come on M, turn it off...what if your 'rents come in?' I said feebly.

'Good point.' she said, and I heard the lock on my door turn. Wish I'd thought of that earlier.

'And secondly...' She continued, 'and don't take this wrong way, but... I would like to see, not because it turns me on or anything, you're my OB for Pete's sake. But I am curious to see something new. That's all. I'm eighteen now B, and my experience in this area is depressingly lacking. I've only ever kissed a boy on screen, and this is the first naked male form I've seen in real life. You must know how hard that part of life is for me B. I can't trust anyone. They all just want me for Her...'

By Her of course she meant H.G. Her other persona and the fantasy of nearly every (hopefully age-appropriate) male on the planet. I knew very well that more than once she'd found herself being courted by some guy, only for them to let slip that they were only interested in her because of her role as H.G. She'd definitely been reduced to tears quite a few times because of it.

And so now it was emotional blackmail too.

'And lastly, it's my birthday. So whatever I say goes!' She said in chipper closing, with the kind of knowing finality that made her so well cast and thus cursed as H.G.

I didn't say anything. What could I? So instead I resigned myself to my embarrassing fate...I was desperate for the awful feeling coursing through my body to go away, even if only temporarily. And so, with a reasonable amount of shame at my situation, slowly thrust my dick into the bed, half-heartedly resuming where I'd left off.

'Atta boy Willy' she said, with more than a hint of glee it must be said.

I tried to ignore her as I tried to get my mind back to thinking of all the things that turn me on. I did really need to cum you must understand. This was the hangover to end all hangovers and I would have done just about anything for any relief whatsoever. So here I was doing anything.

Finally I tucked my hand under my stomach to take hold of my half hard dick. I was getting a little more into it but it felt weird to know I was being watched, and filmed, by M just a few feet away.

'Sure you don't want to roll over? Can't really see much from up here.' I heard her ask, breaking my concentration again. I ignored her. I wasn't going to put on a full show for her. I was doing this for me and my hangover, not her.

'Focus Will', I thought to myself determinedly. I pulled my hand out and gave it a lick and returned to slowly stroking my dick. I lifted my stomach up a little to give myself a better angle, in doing so I suppose giving her and that damn camera a better view. She probably thought I was heeding her suggestion. I wasn't.

'Hey B. Why'd you lick your hand? For lubrication? Does it make it feel better?' She then asked, as if this was a science class or something.

'You're not making this any easier M.' Was all I replied.

'Sorry.' She replied, seemingly admonished.

I kept going, trying to focus my mind on my usual wank bank topics, but it was hard to knowing she was there. I groaned a little in frustration.

'Are you close?' She then whispered to me, belying a level of ignorance on the topic at hand; I was not and just groaned in annoyance.

'Is there anything that would help?' She asked tentatively before hurriedly adding 'You know, to hurry you along.'

'Just be quiet for a sec ok? I can't focus like this.' I pleaded.

As if to heighten my frustration, at that moment a loud voice came bellowing from down the hall.

'You all alright in there?'

It was M's Dad.

'All good Dad. He's just a little worse for wear. We'll be down in a sec.' Came the quick as a flash reply from M.

I sighed loudly and stopped wanking altogether. This wasn't going to work. I felt my hangover come coursing back through me.

'Come on B. You need to hurry up, not bloody well stop.' M whispered to me urgently, seemingly now somehow as invested in this lewd act as I was.

And so at that moment, never to be forgotten for as long as I live, I felt the faint but distinct sensation of fingers as they drifted over my arse cheeks.

Now, it doesn't really matter how bad a hangover you might have, the shock of having a set of fingers that don't belong to you running over your bum will wake you up, at least briefly.

'M! What are you doing?' I hissed to no reply.

I pulled in my legs and came fully up on to all fours, and in doing somehow managed to just thrust my bum further into M's hand. My eyes opened wide when I realised that, instead of pulling her hand away, she hadn't done anything, and she now seemed to be cupping my balls with her fingers.

And more miraculously, and terrifyingly, her thumb was resting gently on my arsehole.

M gasped, I groaned. We both froze. And my previously wilting cock hardened immediately. A foreign hand, no matter where nor whose it is, will do that to a teenage boy.

'M what are you doing?' I whispered fiercely.

'I have absolutely no idea' came the fiercely whispered candid response...'I've never even seen any of this before...let alone, you know, touched...'

'...nuts.' I finished her sentence.

'Indeed' she confirmed.

'And your thumb...on my bum.'

'So it would seem.' She replied, stating the obvious, and then mused;

'Cupped nuts, thumbed bum.'

As I said, she likes wordplay, but I wasn't in the mood to play along.

'You can let go anytime you want you know' I suggested.

'No doubt.' She replied. 'And yet...'

M and I might not have been close, but I knew when she was thinking.

'Out with it M.' I said through gritted teeth. Also seemingly not willing to either end, or further the situation.

'Well here I am, staring at, and cupping your, as you say nuts, and my thumb appears to be in an even more compromising position. Meanwhile, from where I'm sitting I can see that the rest of you down there is now rather excited.'

My cock was throbbing with hardness every few seconds. I said nothing.