Killer Heels

01 Emily

IT’S FRIDAY NIGHT, and the start of the weekend, so I’m having a glass or two of Pinotage as I apply makeup, put finishing touches to lippy, and slide into silk panties. A suspender belt and stockings quickly follows, and then a bra padded out by fake tits, skirt, low-cut top to show off cleavage, and finally my killer heels. Black, shiny patent leather Fuck Me stilettos with four-inch spikes. I’m not sure if I should wear a wig tonight or go au naturel. I have a healthy head of ash-blonde hair down to my shoulders, but occasionally, if the mood takes me, I can be a redhead or a Goth with black Raven’s wings tresses - a shimmer of blue tints under certain lighting. Sexy, I think.

On the fourth Friday of every month, our local sauna hosts a dedicated t-girl night, which is a great place to meet other like-minded individuals, swap gossip, makeup techniques and, of course, bodily fluids. There’s usually a good crowd, and it’s a safe, clean environment in which to let my hair down, mix and, if I’m lucky, maybe pick up a guy. I prefer the Trans Nights, because I can attend fully dressed. The management are snotty about that on what they call standard days, or worse, naked days. I mean, I’m okay with the notion that the sauna is for predominantly gay or bi-sexual men to hook up, and have uninhibited sex in various parts of the club, but being told I have to be naked, or wear a towel, kind of puts a damper on things. On naked days, I’m allowed to wear shoes, spectacles - oh, wow, how fucking cool is that? I can wear a wig, and carry a handbag, but at other times, they’ll allow lingerie, knickers and a bra. Jesus, it definitely puts a dent in my style. I love to be dressed. I spend a lot of time pampering my flesh to ensure a convincing appearance. Waxing and shaving, exfoliating and moisturising regularly earns me compliments, and lovers. Spending cash on decent outfits that accentuate my assets is viewed as an investment, and not a luxury. I adore looking good, being well-dressed, and smelling alluring, so I won’t buy any shit perfumes or crap clothes. I take one last look in the mirror, drain the dregs from the glass, clippety-clop out onto the street, hail a passing cab, and off I go. It’s a ten-minute ride.

The sauna isn’t as full as I’ve seen it in the past, but there’s a decent crowd, and I spot a few familiar faces. I meet a girl who’s been cross-dressing since before I was born, so God knows how old she is. I settle next to her in a secluded corner, and we’re soon busy chit-chatting, you know; taking a stroll down Memory Lane? The sofa is comfortable and the wine is flowing, and she looks at me over the rim of her glass, and says,

I envy you young people. You have it all on a plate these days, sweetheart, what with the internet and such like. What did you say your name was again, lovey?

Emily, I respond half-heartedly, wondering why she bothers asking my name when she calls me sweetheart all the time, but I’m intrigued, and start thinking. At twenty-two, I’ve grown up with the internet. I’m used to using computers, social media, and mobile phones, so I start trying imagine what life was like without them, and I’m baffled. It’s a mystery.

How’d you mean? I ask, leaning forward.

Well, in my day, being a transvestite wasn’t the done thing in public, sweetheart, see? It was dangerous. You had to be careful where you went and who you spoke to, if you didn’t want the shit kicked out of you, that is.

"Really?" I say, and I’m genuinely surprised.

Oh-ho, yes, sweetheart, she says, taking another sip of wine, I was in my 30’s during the 1980’s, and it was a fabulous time.

I’m doing the mental arithmetic, and can’t believe the cross-dresser sitting next to me is almost seventy.

I could still pass for a gay boy in his mid-twenties, but my Trans side was harder to suppress. There was a lot of drugs and sex as well, and I was a pretty promiscuous cross-dresser.

Well, I don’t have a problem with promiscuity at all. I like being promiscuous, see little or nothing wrong with putting it about, and enjoy a healthy sex life. Oh, I know there’s the scare-mongering about sexually transmitted infections and such like, but I have regular check-ups, so I don’t see the problem.

I’m Doris, by the way, sweetheart, she leers, as if this is some kind of private joke, "but I prefer to use the online moniker of Tiny Tears."

So, I say, ignoring the useless information, did you ever think about going the whole hog and transitioning?

She shakes her head, and laughs,

No. I was a skinny punk bisexual freak surrounded by transphobic bigots, and judgmental psychiatrists, and I was afraid of being alone forever. I dreaded electrolysis, knew I’d never pass for a prim and proper straight girl, and there was no internet to research that shit, see?

Right, I say, realizing why she’s bitter, and maybe envious of me and my generation. I too have had my fill of judgmental psychiatrists, but I want to explore this further, have a longer conversation about it, and gain an insight as to what it was like back then. Then a hunky guy approaches our table, and our minds are suddenly on other things. I’m squirming in a seat to make my skirt ride up enough to show off stockings-tops and thighs, maybe a glimpse of silk panties too but, as I toss my mane of long hair, pout glossy lips, and give him my best Come Hither smile, he makes it plain he’s in the market for an older model. Doris pats my thigh in consolation,

Many a good tune played on an old violin, lovey.

I’m absolutely incensed, to be honest. My regulars all tell me how drop-dead gorgeous I am, how convincing I look, yet, this old bag gets to pull, and I’m left gawping at empty air. Fuck me gently, Jesus.

02 Emily

THE FOLLOWING TUESDAY morning, I rise early and, if I’m honest, I’m still stinging after last Friday night. Talk about being shown up? Oh, well, I tell myself, at least I have the internet on my side. She may have pulled the rug from under me, and pulled the guy too, but I have an army of guys at my fingertips. A few clicks of the keypad, and I can summon up whoever I fancy. The thing about modern technology is that it’s so quick. Mobile phones to take a selfie - no matter what the content - and it’s on the web in a matter of minutes. Dating sites that cost nothing to join, and often cost nothing to send messages to others either. Okay, a lot of the guys on there are total fuck-ups. They’ll waste your time telling you how horny they are, or how much they need sex, but often they just collect pictures to wank over. Well, my profile page is a wanker’s paradise, let me tell you. I spent a lot of time, and put a shed load of effort into making it look classy - or my version of classy. There are some real scumbags out there too; t-girls who make us all seem cheap or slutty, with profile names that always include the words whore, slut or sissy. Hey, I love to fuck, but I’m neither whore nor slut, and just because I dress doesn’t make me a sissy either. I’m a gay guy who loves to wear women’s clothing, meet other guys, and get down to some good old-fashioned sex. I don’t care if the guys are gay or straight - yeah, ha-fucking-ha. If a guy has my cock in his mouth, he can think what he likes, call himself an ostrich for all I care, but he isn’t straight. If he takes it up the cat-flap to get his jollies he’s not straight. He’s just as gay as I am, but daren’t admit it; to himself or his wife.

I have a hot shower, wax legs, balls and crack, fire up the lappy and log in. I have a hotlist of regulars, but none of them are online or looking, so I eat breakfast, watch a bit of news, then dress. My wardrobe is eclectic, suitable for a wide range of sexual appetites and fetishes, and I’m spoilt for choice. I select a tight black skirt and matching satin top, slip the fake boobs into cups of a lace bra and panties, roll on the stockings. I love this part the most. I feel really horny, but definitely feminine with stockings on. A dark brown bob wig on top, black patent high heels below, and Emily’s ready for action.

The trouble is, no-one seems ready for me. It’s one of those days when there are fish around but none are biting.

By 9:30, I’ve decided I’m wasting my time, and I’m about to log off, power down, when a message hits my inbox.

Hey sexy R U free 2 meet?

Call me a snob, but I hate text speak. I know it makes things easier if you’re on a phone, but to me it smacks of laziness, ignorance or a lack of education. I have degrees in engineering and computer science, and an ‘A’ Level in English, so I always use proper punctuated English, even on a phone. Okay, it may take a little longer to compose, but even predictive text suggests proper nouns, verbs and adverbs, so there’s no excuse for abbreviated bollocks. I overlook bad grammar in favor of groin. This guy never disappoints.

Yes, I’m home and dressed. Five minutes?

He doesn’t reply, so I know the car will be in front of my place within five minutes, and his engine is bound to be revving too. He’ll be firing on all six inches. He waves as he climbs out of a shabby grey Ford Escort, and I blow him a kiss before pulling curtains together. He opens the front door, and I hear his rhythmic footfalls on the stairs, setting my heart beating faster in a mixture of excitement and fear, or maybe just anticipation.

He walks through the bedroom door with a broad grin on his chops, arms open wide, and an obvious lump at the front of his jeans. I let him embrace me, press hardness against me, and seal my mouth with his. My palm slides to his crotch, and he whispers my name. I don’t know his. To me he’s just TVAdmirer77, (42), and as far as he’s concerned, I’m Emily. I think he might be married but I don’t care. He’s tall, exercises to stay in shape, and smells good. He also fucks like a shunting train. His jeans and shorts are soon around his ankles, and I’ve a mouthful of throbbing cock. It isn’t massive, but hot, hard and rigid is playing my favourite song. Yummy.

Let me suck you, hun, he gasps.

Another perk of the job? Too right. Cocks in frocks never turn down the chance of being blown. Why would we? He’s on his knees, tugs my panties aside and laps my limp noodle, which rises to the occasion. I’m surprised by this, because I don’t normally manage to become hard in girlie mode, well, not often. Today’s a bonus, so we climb onto a bed for a sixty-nine, me deep-throating as he licks, sucks and teases my painful erection. I’m so big I can’t believe it. I’ve never been so hard. It fucking hurts, and I want to cum. I roll onto my back, let his fingers and lips work their magic, pushing me higher, as a slippery finger snakes into my crack, and up my hole.

Well, that’s it; that’s the trigger. My magma chamber is at critical mass, and it erupts in a molten fury, spurting and squirting a spiraling knotted rope of cum. It flies up my skirt, my top, over my head in a graceful arc to spatter the wall and headboard. Oh, fucking wow!

I’m squirming in ecstasy. He sucks the shaft to drain me of every last drop of jizz,

Oh, yeah, babe, I tell him, that’s great, so fucking great. Fancy fucking me now?

That dirty grin is still wide on his face as I roll onto all fours, arse in the air, and ready for a doggy-style bit of action. I always prefer fucking this way, mainly so I don’t have to see Cum Face, you know? I can’t stand the crazy faces guys pull when they shoot their shot, and it usually makes me laugh - which isn’t a great confidence booster at that particular moment. To save embarrassment or damaged egos, I insist on having my back to them. It’s often good to feel them shoot cum over my arse, and back too. He’s up to his balls in me, ploughing a furrow, deep and hard, and my back arches in pleasure as he rubs onto my prostate. I know what’s coming next, even before he says a word. I know he’ll say it, and he does,

Come on, baby, beg me for it; talk dirty, and tell me how bad you want it.

It’s not really hard work, or lying.

Oh, yeah, Daddy, I’m a filthy whore, but I love it. I want it deep inside me. Fuck me. Pump me full of it.

That’s it, bitch, fucking beg.

Oh, please, Daddy, pretty please, fuck me.

Yes, I know it’s like the script of some cheap shitty porn movie, and I should laugh at it, but it gets him from A to B with as little fuss as possible on my part.

Yes, I question the incestuous overtones involved. I can never get my head around this Daddy shit. I mean, I know there are some sick bastards out there who do like that sort of depravity, but, touch wood, I’ve never met a real live pedophile yet, well, except Stephanie’s dad. I try not to think about that these days.

Anyway, it works. Dirty cum-slut is on the receiving end of a fresh delivery of hot juicy jizz and, like a good girl, I moan my appreciation, wriggle my arse, and wait for him to deflate, slide from my sloppy hole, and use a dishcloth to wipe away the mess before he showers.

I make coffee, and we chat for half-an-hour, but then he does his usual glance at a wristwatch,

Christ, is that the time? he gasps.

He twirls car keys, kisses my cheek, and he’s off.

My turn to shower again, and then I eat a light lunch. I might go shopping for new stockings this afternoon.

03 Alice

WEDNESDAY MORNINGS are always reserved for special fun with Alice. We do cam work on Wednesdays, to tease our followers and admirers, and I’m willing to bet that if we set up as a proper online business, we could make a real killing. We could make a fucking mint letting people watch us do what we like to do anyway in private. Makes sense to me, but Alice’s all prissy about it. Exploitation is mentioned, but I wonder, who would be the exploited in the equation? Probably the chimps paying, I reckon. She always turns up at ten, dressed to the nines, and looking a million dollars. If there really is such a thing as love, then I think I’ve got it bad for her. We’ll have to put up with the usual rigmarole before she arrives, I suppose. It’s a ritual that always precedes Alice’s arrival, like foreplay, I suppose you could say, although most of the fucking idiots I’ve met think that taking their socks off is classed as foreplay. Some don’t even shower. Well, no wash, no fuck is my golden rule; always.

Standing in front of the full-length mirror, naked, I go through all the psycho-babble I was subject to in therapy. I’m narcissistic, in love with myself, but because I can’t fuck myself, I have to let others do it by proxy. I dress as a female to pander to my femme side, but don’t want to be female. I simply want my male side to adore me as a girl to complete a self-love desire cycle. It’s complicated, doesn’t make much sense, but I think Alice understands it more than I do. I remember the term Gender Dysphoria being stuck in there somewhere, or was it Incongruence? Fuck knows.

I put on her music, letting images fill my mind as it seeps into my soul. It’s the same song every time; Strange Little Girl. It was originally recorded by a band called The Stranglers, but Alice prefers the Tori Amos version. I’m humming along, eyes closed. Clips from the promotional video repeat in my head of a dark-haired girl running in a field of corn, followed by a wolf. Red thunderhead skies, and a tiny Alice in Wonderland house, where dimensions distort, and the girl transforms into a giant. She picks up the wolf, and puts it into a matchbox, but then the wolf is Tori Amos. It’s obviously symbolism for something but I don’t get it. I set the song to repeat on the Boombox on a dresser in the corner of my bedroom, waiting for Alice.

Doctor Jacobs, who I mentally refer to now as Doctor Jekyll, was supposed to help me sorting my head out, but he was just too fucking nosey, you know? All the time; questions, questions and more questions about shit that I don’t think is the least bit relevant to me wanting to be a girl. Do I lie to make things go smoother; true or false? I rarely connect emotionally with others; true or false? I’ve no problem with lying to get what I want; true or false? On and on he went, and I finally became so bored with it that I stopped seeing him. He’s a fucking quack. Alice agrees. What does he know? I aced his stupid test too, and scored thirty-six, but all he could do was frown, and moan about it, looking glum, and start asking even more stupid questions. The final straw is when he tells me not to listen to Alice’s advice, not to trust her. Fuck him. I stop going and move away. I love Alice more than I love him.

I feel warm arms embracing me; open my eyes to see her smiling through the glass. God, she’s gorgeous today. She has that epic Goth-style look, you know? Really dark eye-shadow and thick mascara smeared around sparkling hazel eyes, black glossy lips and hair the colour of night; impenetrable black, like a Raven’s wings; stunning. I’m mesmerised by her eyes; so vivid, piercing, like mirrors to her soul, and want to fall deep into the lakes of darkness, drown in her lusty glory.

On the bed, a hand closes around my erection, slowly and inexorably taking me higher, forcing me to gasp her name, hear it echo from the walls as pleasure increases.

‘Oh, Alice, Alice, Alice, yes,’ I hiss.

My heels dig deeper into the softness of a mattress as my buttocks and hips rise in response to that teasing hand, balls aching for release. A fierce throbbing pain, more so than yesterday, is threatening to tear me apart, expanding, spreading outward through my entire being. As I reach a point of no return, her hand releases me, leaves my rock hardness pointing proud and erect up my abdomen. I can hold back no longer, screaming filthy exhortations to her, fingers digging into a duvet, as my cock pumps, squirting projectile cum into my face. Alice’s so dirty, so naughty, but knows exactly what I like. I love her so much. I fall asleep in her embrace and, when I awaken from a sated slumber, she’s gone.

After a shower and a light lunch, I fire up the laptop, and cruise the net to see if I can land another fish for this evening. Alice always brings out a raging hunger for sex in me.

04 Emily

TINY TEARS, (57), the old tranny from last Friday night is online, and cruising for some action. Her profile claims she’s a fifty-seven year-old, unconvincing cross-dresser with a passion for the younger guys. Well, I’ll agree that she’s unconvincing, but she definitely isn’t fifty-seven. She looks like an old bloke in drag; a really old bloke in drag. You know those pantomime dames? She looks like one of those, only uglier. She’s been rated quite highly by a list of former acquaintances, and I note that the latest of these is the guy at the sauna. He was mightily impressed by her, says he’s going to arrange another session, but I piss my pants laughing at his last comment,

She never fails to disappoint me.

The stupid bastard; typical of the chimps on here. He either means she never fails to please, or that she never disappoints, not a combination of both. I really do despair of the poor levels of literacy and command of English on here. A message pings my Inbox from the old girl. I’m in two minds whether or not to read it, but the temptation is almost as great as that of Pandora’s, and I have to. I let the evil out, forgetting that Hope always remained trapped at the bottom; silly me. Well, Hope’s not a bad thing.

Within an hour, I’m at her door, nervous, but eager to play; to satisfy a craving aroused by Alice. Doris likes to be dominant with other t-girls, but I don’t mind that at all. I often need what they euphemistically call a firm hand to guide me, although I draw the line at any physical force being used to control me. She’s wearing a curly auburn wig, almost as crinkly as her puckered, withered smoker’s lips and craggy face. Pale pink lippy and mauve eye-shadow clashes with the green satin of a dress, and blue high heels. She reminds me of a kiddie let loose in a dressing-up box at nursery.

Come in, sweetheart, she murmurs, silhouetted in a doorway, a hand on the jamb, the other extended in what she thinks is a welcoming gesture. I squeeze past, feel an erection against my buttock, and know she’s horny and up for it. She leads me upstairs to a back bedroom, curtains drawn tightly shut. Low-level light from a bedside lamp sends shadows dancing over walls covered in lurid floral patterned paper. She’s grinning across a bed, reaching around to her back, and unzipping the dress, letting it fall, and stepping out of it.

Come here, sweetheart, let me have a closer look at you, eh?

I don’t mind. After all, at least I’ve made an effort to look good in a matching grey ensemble; a short, business-style jacket, cream blouse, grey skirt and heels. I’ve put on a suspender belt and black silk stockings, but without a seam up the rear. Legs don’t have seams, so I could never get my head around wearing seamed hosiery. It’s daft. I stand, compliant and obedient for her appraisal, letting glittering piggish eyes roam my body, tip to toe,

Hmm, you look lovely, sweetheart, let’s begin, she whispers, tongue licking ancient lips, fingers fumbling at the single button of the jacket. That’s the third time she’s called me sweetheart in as many minutes, and I hate it. My mouth is dry as the blouse is unbuttoned, pulled over my shoulders, and discarded by the foot of the bed. Then she’s sliding the zipper of the skirt, tugging it over hips and down to ankles, crouching with her face opposite my crotch. As I step out of it she caresses my groin,

Not in the mood, sweetie? she asks.

I never get hard in girlie gear, I explain, although I know that’s a lie now. I don’t really care anyway.

Not to worry, honey, I do - always. Feel—

I don’t actually need to feel the front of her panties to know she’s rock hard; I can see it tenting fabric, eager to be unleashed. It’s not impressive, but I have to stress, I’m not a size queen. Big cock’s usually belong to a small IQ, and have a cunt on the other end of them.

I sit on the edge of the bed, slide the elasticated band of panties down to let her prod free of confinement; uncut in a sea of curly grey pubic hair. Christ! At least trim the fucker now and again, you dirty old bitch. Suppressing nausea and distaste, I take her dribbling dong onto my tongue, let salty pre-cum slake my uvula, and fondle her balls with fingertips. Her hands are on my head, holding it as she face-fucks me; sliding cock in and out, moaning what a sweetheart I am.

That’s it, that’s it, ooh, yes, I like that, sweetheart.

I don’t know if she wants to face-fuck to completion, but I hope not. I’m not big on swallowing jizz, sometimes gagging on it, and I hate facials. There’s nothing worse in the world than cum spraying your chin, nose, and in your eyes; fucking revolting, to be honest. Some girls believe it’s good for the complexion, but then I’ve heard of them rubbing puppy piss on their faces too. Urgh!

There now, she sighs, pulling free, and letting go of my head, I’m ready for a fuck, sweetheart, are you?

Yes, Mistress, I say, knowing that’s what the cunt wants to hear.

Good girl. Stand up for me.

I rise, expecting sagging puckered lips to try to kiss me, so I turn away quickly, adopt a position on all fours on the edge of the bed, arse in the air, waiting.

Hmm, someone’s keen, she giggles, and I hear foil rip as she unwraps a condom, rolls rubber over the shaft, and then slakes my crack in cold lube. Fingers probe my hole, worming deeper inside, making me slick.

Oh, Mistress, I coo, that’s lovely.

A hand unexpectedly slaps my buttocks hard, and I gasp through clenched teeth.

Be quiet, you little slut, she hisses, slaps me again, and then pushes her cock against my sphincter. Here we go, I tell myself, get ready for it.

Now, beg for it, you dirty whore. Tell me you want it. Come on, let me hear it—

I told you. I knew it would come. Okay, here goes,

Oh, please, Mistress, fuck your wanton whore.

Another slap.

Again, bitch!

Please, please, pretty-please, Mistress.

That’s it, she says, pushing deep into me, ramming a rigid hotrod home; a piston sliding into my cleft. Faster and faster, breathing hard, almost asthmatic, in time to the pelvic thrusts, and her mantra begins,

Oh, yes, bitch, oh yes. Oh God, yes, bitch, that’s it.

She’s not going to last long at all, not that I care. My feelings of self-loathing are surfacing for allowing this to happen, and a voice in my head is taunting me.

"You never learn, do you, Emily? Never learn. No matter how many times I tell you, you never listen to me."

I know Alice’s not here, but I can hear her, chiding, disappointed in me, like a nagging twin sister I never had. I’m going to be in trouble with her again. I can tell. The bedroom wall is back in focus, a croaking at my rear,

Oh, yes, bitch, oh yes. Oh God, yes, you slut, that’s it. That’s fucking it, now. There you go. Ah, yes, lovely.

She slips from me, deflated, slimy condom slithering out moments after the head, pendulous with spent juices, and hanging from the bell-end; disgusting. She pats my buttocks, knots the rubber, and wraps it in a tissue,

Get dressed now, sweetheart, I’m done. I’ll just get rid of this.

She disappears from the room and, as I’m pulling on