Escapism: The Modern Man

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Escapism can be a wonderful thing.
2.9k words
4.52
12.7k
11

Part 2 of the 2 part series

Updated 08/30/2017
Created 02/07/2017
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*Synopsis:

25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.*

ESCAPISM: The Modern Man

'Fuck yes! Yes Daddy! Fuck me like a little bitch!' I scream into the pillow. My arched back allowing my partner full access to my greedy asshole. He slams harder in response.

One leg bent, pointing a pink glossy stiletto heel towards the ceiling, bouncing against my stocking clad legs.

Straightening my long caramel blonde wig, I run my hands against my partner's sturdy thigh, reiterating the approval of my girlish screams. My high pitched, fake American, best attempt at a porn star. In my mind right now I am the star of the best porn flick anyone has ever watched.

My lover grunts, slaps my pert ass. His encouragement less vocal, less dramatic. 'Fuck. Yeh. Take that dick.'

I pinch my nipples through the silk of the pink satin teddy that clings to my smooth, hairless body. The dress riding up my back, the thong panties pushed to one side, as the massive cock pumps in and out of my ass.

If you've never been fucked, it's hard to explain the feeling. It's a sensation that hurts like hell at first, but then slams through your body with pure ecstasy. You feel like you're on the end of a battering ram, and each blow sends a wave of pleasure throughout your body. Your dick throbs and oozes precum. There's a sharp warmness somewhere deep inside your ass that seems to reach the tips of your fingers. Your cock is harder than it's ever been. Each time you scream like a girl you feel a little part of your masculinity die. A new girlish wave of drunkenness clouds your mind.

Then the dick pops out and leaves me empty, incomplete.

'Turn' an imperative grunt commands.

I flip over on to my stomach, knowing that the climax is on its way. Knowing that my reward is waiting. I stare up lovingly in to my partner's eyes. His face a grimace, his beard glistening with perspiration dripping on to his firm pecks. He looks at me in pure lust. He wants me. I will send him over the edge.

I began to lick at the tip of his massive cock. It's salty to the taste, but not unpleasant. He tugs at it furiously, as I try to look as sexy as possible, try to play the part I was born to star in.

'Cum for me Daddy!' I whisper, brattish and impatient. Although this is a moment I savour, I'm in no actual rush.

'I want your cum in my mouth!' I pout. Eyelashes flutter.

His face scrunches. His body tenses. Anticipation overwhelms me.

'Ughhhh nfffff' undecipherable pleasure escapes his lips.

As wave after wave of thick gloopy semen splats against my lip-gloss covered mouth, I giggle, I gargle, I lick my lips. The cum runs down my chin. I swallow most, savouring its rich sourness.

I look up in to my partner's eyes. Almost seeing from his perspective as he looks down at me. I grin, knowing that I must look fucking terrific right now. I smile at how much has changed, how far I've come, how right this feels.

It wasn't always this way. Escapism is a wonderful thing.

-

The Modern Man is a hair-slicked-back, lumberjack shirt wearing, Spartan beard grooming, gym membership owning, generic attempt at mirroring the latest cover image of GQ magazine – even though nobody has actually seen, let alone bought, this image. It is an image burned into the sub-conscious of a generation who aren't exactly sure how it got there in the first place. It is a class of men who, to varying degrees, are happy to proclaim their own grooming – 'manscaping' – routine and how they use as much fake tan as their bronze-varnish-faced girlfriends.

Sure, he Tweets – a Modern Man has a firm opinion on everything. Trump, Rooney, Bowie. His irrelevant, politically-correct dogma is spewed out at regular intervals to an audience too self-absorbed to give two fucks. He Instagrams his meals, he Facebooks the most mind-blowing or gut-wrenchingly funny videos doing the rounds on the World Wide Web. Like dogs barking and yelping in to the echoing night time, just hoping some other desperate fool out there gives a single shit. Hoping they aren't alone.

See, the Modern Man has very few close personal friends. The lads meet up at semi-regular intervals: football, nights out, gigs, stag dos. They spend more time with their girlfriend's friends, taggers-on, work colleagues. Work is a grey area. This can vary between Modern Men depending on area of expertise and social demographic. You don't have to work at Innocent-fucking-Smoothies to be a Modern Man. You can work as a plasterer, a fitness coach, a butcher's assistant. Your position is not important, it is the representation of the self. You can lie, cheat, steal, borrow and beg: it doesn't matter, as long as you present the correct image to rest of the world. It doesn't matter what the food at the restaurant tastes like, as long as the triple-cooked-chips are in a stainless steel basket, the frozen beef burger placed delicately between a brioche bun, served on a slate tile, the buildings wall's distressed, the fittings rural or industrial, high TripAdvisor rating.

This is a generation born out of Lad Culture, and although their own fathers may not have gone through this rebirth of the white working class, they certainly grew up through it. They were too young to realise, but the classic Adidas trainers, Baddiel and Skinner, Oasis, chain pubs, tubthumping of the 90s has left a stain that ultimately shaped their current lives in some way.

This, in fact, is a return to Yuppie Culture of the eighties, minus the shoulder pads and ill-fitting clothes. The fashion may have changed, but the importance of the self is firm. It is Partick Bateman without the bank balance. Having internet access from an early age has weakened their morals and beliefs. Pornography has encouraged niche fetishes and a lack of respect for women. The mask of online anonymity has developed hatred. Text messages and group chats replace real friendships.

But that's alright, because the Modern Man looks good. His aftershave smells expensive. His trainers are box fresh. His teeth are pearly white. His biceps bulge against his skinny fit designer t-shit.

He looks happy.

-

This is a bold brush stroke.

Not every man in Western Civilisation falls in to this demographic.

Not every Modern Man adheres to all of these principles.

Let's face it, if you're reading this story, and you have read this far, you either A: like to dress up like a girl, B: want to fuck a man who dresses up like a girl, or reside in category C: the confused region in between, where in fact it's probably both. In recent popular surveys by trashy online publications, crossdressing ranked at number 8 of 'common fetishes that aren't actually that unusual', while Shemale porn grows more and more popular each year, making up for 18% of the total consumption of all online fap sources. Now, these are the questions you have to ask yourself: is this one of those Modern Man fetishes? Or are you escaping that tag entirely, fed up with your social surroundings? Seeking something more?

It is out of rejection of being a Modern Man that I became a sissy.

Escapism is a wonderful thing.

-

It all started when I shaved my legs. Well, it probably started as a child wearing my Mum's knickers, eventually escalating in to flashes of crossdressing obsession. But that's a story for another time.

When I first shaved my legs, it was a physical rejection of the person I had become.

I was bored, tired and ultimately pretty depressed. I was 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. My boss always questioning my punctuality and disappearance around deadlines. Sick of weekends consisting of some shit night out to another shit club. Sick of drinking through a lack of anything else to do. Sick of trying to pull the hottest girl in the bar, and ultimately settling for whoever falls for my shit lines. Sick to the back teeth of following a football team that never wins. Sick of my friends and everything we did together.

I needed a drastic change. Some people may have committed to hobbies, explored the arts, moved countries. Fuck, some people may have even found God.

I shaved my legs.

The dark night already drawing in, the grey darkness clouding the apartment as I arrived home from work. Another grey, mundane day. January is the worst. The light from the fridge illuminated my face as I scanned its contents. Half a carton of orange juice. A half consumed block of cheese. I sighed, knowing I'd have to make a trip to the shop. These excursions regular and erratic, never buying enough food to last more than a day or two.

I slung my suit jacket over the dining table and began undressing. Most media jobs don't involve wearing a suit, but our office lives and dies by the beliefs of the older generations. Fucking 70s work ethics. I seemed to be the only person in there that had to take work home with them, everyone else clocked in, logged on and fucked off home at 5:30. I couldn't just produce my writing to that deadline. When inspiration struck, it didn't give a shit about the 'working day'.

Today was no different, I'd tried to scrape the words together for an article entitled 'The Modern Man', some vague idea that had been forming at the back of my mind for some time. But ultimately I'd got nowhere with it. I felt observed and scrutinised in that office. A heavy weight attached the chain-like tie around my neck. Apparently January 20th was 'National Fetish Day', and, as my editor kept reminding me, I had to produce something by the end of the week to coincide with this.

Lazy journalism is awash all over the internet in 2017. Websites and publishers care more about hits and ad revenues than actual content. They treat their audience with a distain that almost says 'I know you clicked on this out of pure boredom – probably while taking a shit'. It's not why I got into the profession. And yet on that night I began producing my laziest piece of work to date. It might just have happened to change my life. Maybe even saved it?

I slouched in to my office chair, began googling 'fetish' in the hope of finding something quick and easy to plagiarise. Keep the work wolves at bay tomorrow. Stumbling across the all too familiar top 10s, top 17s, 5 things you didn't know type nonsense, my idea formed. A quick easy list 'common fetishes that aren't actually that unusual'. Easy. Then I'll go buy food and veg out in front of the TV. I was simply going to copy a few of their results, change the order, and add a few words. Done.

I placed a few of the weirder fetishes in the top ranks – apparently adult babies are a thing now, so is tentacle porn and strapons. I began filling out the others entries with some more obvious vanilla choices: feet worship, leather, rubber, role play, crossdressing.

I stopped at that last entry.

For some reason it made my heart race a little faster.

I don't why, I guess it caught me off guard. As a teenager this was something I did. Regularly. Usually with my Mum's clothes, masturbating furiously in front of the bedroom mirror. I'd written it off as some kind of weird phase, an illness almost. I'd weaned myself away from it like a drug addiction – convinced that it was something too fucked up to continue participating in. I'd never spoken about it, shared it, or analysed it.

I searched through a couple of similar articles, and, low and behold, most of these sites had crossdressing listed in a similar position. Number 8. Number 6. Apparently it was a thing. People did this in 2017. My dick began to stiffen at the thought. Fuck, I'd completely not thought about wearing women's clothes for a long time. The self-inflicted rehab had worked. The addiction was cured. At least that's what I thought.

An hour of internet research later, and a short trip to the supermarket, I found myself stood in the women's clothing section. The Lingerie section. Mainly aimed at older women, conservative and plain in their choices, but there were a few more adventurous choices – reds, blacks, neon pinks. The kinky ones who buy a little something for the weekend while buying cereal and toilet rolls. Hands trembling, two voices began running through my mind.

One, loud and clear screaming: 'This is fucking madness! What are you doing? What if someone you know walks in? What will they think at the till?'

The other less prominent, but more persuasive, warming and exciting: 'Who cares? It'll be fun. Self-service checkout. Remember how good it used to feel?'

I bet you know which one won the argument.

I returned from the store with a handful of lingerie, stockings, a dress and a tube of cheap unbranded lipstick. Fuck. The adrenaline pumping through my body was intoxicating. I felt more awake and alive than I had done in a long time. Feverishly I tore through the packaging, laying it all out on the wrinkled covers of my bed. I'd guessed at sizes, gone for somewhere between crazy huge and medium fit.

I remember gulping, before I took the plunge.

I tugged at a pair of black lace panties, adjusting the elastic around my waste, rearranging the pink frills which detailed the hem.

Wow.

My dick sprang to attention. My hairs stood on end. I rubbed the front of the lace, the texture and pattern evoking a familiar feeling of my youth. This is what you've been missing.

Wriggling into the bra, adjusting the straps, cupping my chest. I don't why – and I suppose none of us ever do – it was exciting.

I stood in front of the mirror, the pastel coloured floral dress – too tight – clung to my body in a way that would have looked ridiculous to an onlooker. But the sensation of it, this breaking the rules feeling, made me feel light headed. It felt liberating. I felt different. Less tense. Relaxed, almost – aside from the raging hardon tenting the front of the dress. I decided right then and there that I was committing to this. This was my thing and I was going to explore it. Fuck it, what did I have to lose?

10 minutes later, I shaved my legs in the shower. Off came the beard – the Modern Man taking a blow to the face as his mask began to slip.

I stood in front of the bedroom mirror, pouting. Rubbing my smooth legs through the electricity of the stockings. Pulling at their tops and feeling them snap back into place. I caressed my rock hard member through its lacy confines. It begged to be freed, it begged to stand proud. It didn't take long before the panties began to moisten, masses of pre-cum gushing into the lace, an inevitable sticky wet patch forming.

A moan escaped my mouth. A guttural yet high pitched feminine sound. It was like it was always there. Always wanting to be released.

I erupted into the panties. The longest and most intense orgasm I had ever had. It was like all of the moisture in my body had just been shot out of the end of my dick. The panties sodden, sticky and ruined.

When the heat of the climax had finally died down, I just stood in silence. Completely shocked by what had come over me. It felt brilliant. And I wanted more of it.

I slept that night like a massive weight had been lifted from my shoulders. Something had changed. A fog had been lifted.

Escapism can be a wonderful thing.

-

I scrunch my arms around Sal's neck as he embraces me before leaving. I stand on my tiptoes as he squeezes the bare cheeks of my ass. We kiss goodnight, our tongues deep, exploring, caressing.

'See ya, sexy' he whispers.

'Night, baby' I purr.

'You call me tomorrow?' he enquires, half turned, ready to leave.

'Of course'

He leaves and I'm alone. Cum stained and violated. Completely satisfied. I totter back to the living room and remove my heels. I inspect my nails, one of them missing, laying somewhere in the bedroom, the debris of our love making. I feel warm and fulfilled. The warm late July night is slowly ebbing away, birds are beginning to sing, as I undress and slip into a sheer silk nightie. Removing my makeup and the glittering cum slicks off my chin, I clamber into bed, my knees marked, my asshole sore and spent. I feel truly content, as I drift off into a deep reverie - thoughts of how this all began spinning through my mind.

-

(Thanks, for reading. If you enjoyed this in the slightest, let me know that you are out there and let me know what you think. Even if you thought it was rubbish! As fun as it is to write these stories, it definitely helps knowing someone has taken the time to read them. )

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AnonymousAnonymousabout 3 years ago
Sissy

After a year of turning myself in to the women i am now.Long hair breast firm ass hairless body.Now the next step sex but could i do it and with who were and how.I found a couple who will help me.I dressed black corset thong black stockings heels dress.Fixed my hair eyes red lips and nails and face make up.I met the couple he is a cross dresser she loves spandex and laytex..He started by sucking my cock and swallowing my load.She followed by sucking my cock and milking me dry.Then it was my turn to suck his cock.I was supprised at the size of his cock 7''2 1/2 '' round.I dropped to my knees opened wide and in went his cock deep down my throat .I felt her lifting my dress moving my thong and pushing a monster horse cock strap on deep in my ass all 12'' 3'' round.Soon the cum was flooding my mouth and filling my belly.

AnonymousAnonymousabout 5 years ago
Odd timing to find this great piece!

I literally just fell back into crossdressing about 2 weeks ago after a long hiatus and i feel like this story summed up my feelings the same way. Work and all other things are easier...difference is that ive not made the leap to involving other people yet!

AnonymousAnonymousabout 7 years ago
Accurate, insightful, and erotic

How true that so many of us "girls" hide behind beards ...

Thank you for such a wonderful telling of your tale. I know I would love to hear more of your journey, as I'm sure so many of your readers would.

striker_1909striker_1909about 7 years ago
great description of receiving anal

I felt the same in anal sex as described here.

AnonymousAnonymousabout 7 years ago
Nice and different

Will love to read more...

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