crossdressers first time with a guy
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Crossdressers Rush free porn video
If you have a fixed aversion to cross-dressing sissies, you may wish to go elsewhere.
However, my story isn’t about that, although it provides the protagonist vehicle.
It’s about control… self-control, losing control, being controlled and everything out of control.
I hope you enjoy my style …..
p.s. If my humble contribution offends or annoys any readers, I sincerely apologize.
My intent was merely to provide a brief moment of stimulating entertainment.
Comment and ask for the saga to continue, if you liked reading about my first "adventure".
………………………………..
CROSSDRESSERS RUSH … I TAKE THE OLD CAR FOR A SPIN.
I don’t know exactly where my fascination with cross-dressing came from, but I can see many of you
knowingly nod your head when I say I was the only child of a single Mom. When I was 8, Mom was
48, and unfortunately a widow, which somehow made my home-life different from all my school-
friends. I was all she had, and she mollycoddled me. That’s old fashioned speak for saying she
treated me like a precious little jewel, and most of my teachers and many of my peers seemed to
notice and treat me the same. In truth, I understood her situation and consciously quashed my
masculine bravado and the urge for dare-devil antics so as not to give her cause for concern. I went
along with her little games, and played the part of being her meek and docile little boy far longer and
more profoundly than I should. So, having consciously restrained my boisterous and bold
masculinity, I exited my adolescent years being what could be described as an introverted,
Mommas-boy wimp.
But, as the old saying goes, there is someone for everyone, and a few years later I married the
most wonderful woman you could imagine. She isn’t a huge breasted bimbo super-model. But she is
pretty, intelligent, articulate and loyal, and has produced three fine female offspring who all display
the same traits. We are a happy family, and live a comfortable life in suburbia. What’s not to love?
Well, me. Or more precisely, my obsession. I secretly cross-dress.
Ever since I turned 40 a couple of years ago, my obsession has crept further and further into
unchartered and dangerous waters. I’d realised I wanted more than the satisfaction of
looking in the mirror and seeing a fair semblance of a cheap, easy slut looking back.
I began to wonder what would happen if other people saw me.
Would they assume I was what I’d dressed up to be?
It grew into a disturbing and soul-searching muse ……..
What if I went to an underground bar in my hottest attire and full make-up?
What would I do if I piqued a man’s interest, and he came over and started to flirt?
What if his will and claiming insistence took our tryst to a dark corner table?
What if he plied me with heady red wine, which secured me to guest his apartment?
What if he said I’d aroused his desire, and came on strong with determining foreplay?
What if I protest, “Oh no! Please no! Oh, no, not that!”…. yet succumbed to the call of his bed?
What if his ardor held reigning intention, with subversion to commence at my mouth?
What if I opened with heedless abandon, and was held ‘till I tasted his seed?
What if I thrilled to his forced imposition, sealing fate as I swallowed it down?
To be surely then charged that I bend hand and knee, no longer being rated a man?
Would I obey and be his for the taking, and allow him to be my first owner?
What if he then used his total advantage to take all he would at his will?
And what if he took, and dealt evermore taking, ‘til I’d dance to his every demand?
A slave to his will ‘til I begged my release. And what if that just suited me fine?
…… HOWEVER ……..
What if my abandon was captured on camera, and my “date” was a cruel, vicious pimp?
Were I then hooked on the sharp barbs of blackmail, and my shame held me skewered in place?
To be randomly beaten for no reasoned occasion. A reminder of who’s whip-hand held sway.
Then blatantly touted as spineless demeanor. The drag-fag of his sick, twisted stable.
Another bond whore under his jurisdiction. A cheap treat to be loaned out at will.
Sent out to serve with no set precondition. “Anything goes” when hard cash buys you in.
…………………………………….
It was musing the fortunes of exposure and degrading mistreatment which had become my biggest
turn-on. And I just couldn’t stop myself. Time went by, and I remained inside my safe but ever
increasingly unwholesome dark muses. Yet the more sickening and masochistic they became, the
more intoxicating and hypnotic they were. I knew that going outside the house whilst harboring
such dark thoughts would be chancing a perilously thin flimsy limb. So I swore I must never, ever
lose my sense of reason and recklessly dress up and go out and tempt such a fate.
Besides, I was never handed free opportune, so my muse was all that I had.
… until ….
A few months ago my wife and 3 daughters went up-state for a couple of weeks during the school
holidays. My wife’s sister was on the verge of giving birth. Being married to a huge, macho ex-rugby
player, she has always been able to see right through me. Hence we have never been on good
terms, so it was easy for me to excuse myself from the visit. A couple of weeks at home all alone to
indulge in my secret passion… yey!
It was only natural my wife took our fairly new SUV. We have another car. An old tin box we virtually
never use, but I kept it road legal just in case. Well, you know, for whatever…
The free opportune which I’d been relieved to avoid had just fallen slap bang into my lap.
A test for my mettle. A dare for my boundaries. A sail for those unchartered waters.
To dress up, then have a quick cruise around the suburbs at night. I knew I’d swore to myself I
must never go out to tempt the whims of fate, but it would be an unbelievably spine-tingling, nerve
jangling, erotic rush, and result in some of the most intense masturbation sessions ever…… Oh boy!
…..
So the day after they left, and having confirmed their safe up-state arrival, I unearthed my suitcase
of slutty clothes and gaudy make-up from the depths of the garage and headed for the bathroom.
……….
Wow, did I look good. Well, I suppose I would look good to someone who had $50 in their pocket
and was on the prowl for a cheap, easy lay. A female lay, that is. Not some-ones husband.
I felt at ease and comfortable in my outfit. I paraded and strutted around the house, but I couldn’t
resist gravitating back to the full-length mirror in the bathroom. I really did admire the foxy piece of
tail looking back. I did slow seductive twirls to take in the sight.
I could just about see my rosy red toe-nails through my shiny black silk stockings. If I twirled
quickly, my bright red pleated mini-skirt would flick out just far enough to reveal my lace-patterned
stocking tops. If I lifted the hem of my skirt, I could tease a glimpse of my silky, frilly orange panties.
My hands were trembling when in tandem they stroked up and down over the twin false humps at
the front of my rose-patterned, ruby red top, which was doing a lousy job of hiding my
overtly prominent false nipples. I pouted my lips, which flaunted a gloss ruby-red, and my eyelids
fluttered a sexy light blue. I raised my fore-finger and seductively entwined it in the side strands of
my long blonde wig as I practiced my lip pouting and pursing. Just the mere act of teasing myself was
causing an improper stir. When my right hand lowered to the front of my silk orange panties and my
palm gave a few firm rubs, my legs almost gave way. But despite all the attention I was giving myself,
I had only provoked the mere hint of an erection. I’d gone so far down the road of cross-dressing, it
was only the rush from the thought of going out and putting myself at the risk of exposure and
exploitation which turned the key in that particular lock.
Dark muses started to parade across my mind.
Visions of sinister happenings which may befall me if I went out for a drive.
My cock began swelling. I plucked out a large roll of fabric from my secret suitcase.
I unwrapped the long, hard, truncheon-like contents and flicked its switch to test the batteries.
“Oh no!”, I begged as I headed for the bedroom…. “Please don’t do this to yourself…..”
Afterwards, I fell asleep.
……….
It was full-on dark now. A warm, summers Saturday late evening. I freshen my make-up, reset my curly blonde wig and
gird my neck with a long, orange silk scarf. I put on a pair of flat sandals, and without thinking due
reason, picked up the pair of black high-heels which had been on the kitchen table all afternoon.
In the garage, I almost keeled over I was feeling so giddy, and had to place my free hand on the car
roof above the drivers’ door as I took a few deep breaths.
“Do you really want to do this? Stray outside of your safe, secure zone? Into the great unknown?
This could all go horribly wrong.”
As random dark thoughts again flickered before my last-minute hesitation, I felt a stir in my loins.
“Yes, you do want to do this, don’t you? … you dirty, dirty slut.”
Another unwholesome stir. I got in the car and fired her up.
“But remember .. you promised you should never to do this. Please don’t push it too far.”
…………
The first two miles were a very slow meander through my local suburban streets. It was just as well I
was navigating familiar empty roads. Focus was in short supply. Every now and then I’d reach over
to touch the high-heels which were riding shot-gun. I couldn’t stop thinking about the rush it
would be to go somewhere secluded, put them on and have a quick walk around outside the car.
I dry swallowed.
“Are you insane?” I said to my-self. “That, my dumb, slutty friend, would be a bridge too far.”
But my thoughts kept weighing up the various assortment of isolated, dark places near-by. Those
of unfrequented passage and cloistered seclusion where my first venture would go undisturbed.
“Canrich Weir”, I blurted. Being the first words I’d spoken out loud for several hours, I startled
myself. “No, no, no…far too dangerous,” I continued to mumble at the windshield as I shook my
head. “Young couples used to go there to make out. But I’ve heard it’s now the haunt of drug dealers
and criminals and all sorts of low life scum. Don’t even think about it, you self-destructive moron.
Just keep away.”
My car started heading towards Canrich Weir.
I white-knuckle gripped hard on the wheel, as my foot remained glued to the throttle.
“Please don’t take me there, please, no! I’m begging. Please don’t,” I whimpered.
The car turned down the dark, tree-lined lane-way marked "Canrich Weir - no through road".
…………
I pulled into the small car-park at the end of the long, bumpy, pot-holed track. There was no-one
there. I exhaled a deep sigh of relief. I sat motionless for a full five minutes until my pulse-rate
settled down, and my heart wasn’t trying to burst out of my chest. I dry swallowed again and bent
forwards and started removing my flat heeled sandals. If I was going to do this, I was going to do it
right. I wriggled around and finally had my black high heels in place. I sat there for another two
minutes. Mainly to compose myself, but also to satisfy my frazzled nervous system there was
definitely no-one around.
I opened the car door into the nights’ dark seclusion, and was immediately almost blinded by the
bright courtesy light, which seemed to turn the car interior and most of the car-park into day.
“Oh, crap!” as I immediately slumped back into my seat and jabbed the door shut with a loud bang.
Talk about keeping a low profile! I didn’t want that to happen again, so in a state of unnerved
paranoia, I located the fuse-box under the dash and ripped out 3 or 4 fuses.
I opened the door again, more slowly this time, and remained in reassuring darkness. I was taking
short, nervous, light breaths as I stepped out into the moon-lit oasis of the parking lot. I cautiously
stood upright on the uneven roughness of its crude construction. My high heels felt precarious. I
slowly walked a full circle around the car, with one hand tracing the reassuring stability of its steel
shell. Having practiced, I tottered and cautiously ventured further, through the shadows of the
moon-lit trees, towards the small path which leads to the weir itself. I could hear the gentle swish of
water cascading over the weir top. I felt calm. I felt safe. I was a woman alone in the night, and
there was no-one around to threaten or harm me.
I felt a sense of release. I felt complete.
I started down the dim moon-lit path, drawn by the mesmeric tinkle of flowing water.
…………..
Halfway down the path, I was shaken from my serenity by the flicker of headlights through the
spindly tree trunks. They were heading this way. I turned and did a frantic shuffle run, and flung
myself into the drivers’ seat and slammed the door shut in the nick of time. I was positive they
hadn’t seen me. Positive.
The other car parked at the far side of the small lot, thankfully about 100 feet away. I crouched in my seat
with my chest heaving to catch my breath and my heart pounding like a bass drum.
I wasn’t calm now. I felt sick, to be honest. My clothes were in a mess and I was in a panic. I had
to get out of there. My trembling fingers found the key in the ignition, gave it a turn, and….. nothing.
No dash lights, no clicking, and certainly no engine cranking.
Oh, crap, double crap, crap, crap. This definitely wasn’t part of the plan.
I sat there with my brain in such meltdown it didn’t occur to me how this could have happened.
I tried to weigh up my very limited options, occasionally twisting the key to no avail. Eventually I
stopped trying.
After several minutes of blankly staring out through the windshield into the darkness, my despair
and stupor were broken by activity at the other car. Its rear door had opened, and what was
obviously a manly figure stood to water the trees, then strode across in my direction.
“Sorry to bother you, bro,” he assumed at my enclosed black sanctuary. “Have you got a couple of
spare condoms I could beg off you? You know how it is.”
“Sorry, bud,” I replied in the best macho voice I could muster. “I don’t need to use them.”
But he took a step closer, and the bright arc of a powerful flash-light shone in my face. My man face,
with its make-up and long blonde wig. The light then panned down my body to highlight what was
still my dishevelled state, with my red mini-skirt almost around my waist, and my stocking tops and
orange panties on show. The torchlight investigated my empty seats, and thankfully then went out.
“Ah, I see”, said this unknown interloper. He then turned and sauntered back from whence he came.
I twisted the key in the ignition a couple more times, but .. nothing.
Then the front and back doors of the other car opened and a couple of masculine figures strode over
to my door, lit me up with a torch, and knocked on the window, which I had no intention of opening.
“Listen up, fella,” a rather gruff and assertive voice started, “we’ve had a talk, and we reckon that
you of all people would be packing ‘doms, hear what I’m saying?”
“I’m sorry, but honestly, I’m not.”
“Well it’s like this, see,” he persisted through my rolled-up window, “We’ve got a couple of wired
-up chicks over there raring to go, but they’ll only dance on rubber, know what I’m saying?”
“I sympathize with your plight, I tru…”
“Don’t fuck us about, fag”, he snapped. “Open the fucking door, or else we’re coming in bleeding
from glass, yeah?”
This was not looking good. I made one last stab at the ignition key, but when they saw my sly action,
the torch started a determined beat on my window. So with my heart in my boots, I reluctantly
wound down my glass draw-bridge.
A hand reached round and flipped the lock to the rear, and before I knew it, there was one at my
side and one sat behind. Mr. Front rifled through my glove box, and Mr. Back gripped his hands on
my shoulders.
“We can do this the easy way, or the hard way,” says the one in front, having drawn a blank in the
glove compartment. “Where are they?”
“I don’t have any condoms. I’m not that sort of, you know… I don’t do that.”
“All fags have condoms, for when they take it up the ass. Or do you like it bare-back, you fag queer?”
“Look, fellas. I’m not a fag. I’m not a queer and I don’t have any condoms, all right?”
I sigh as a female voice then enters the fray.
“What’s going on, Pell?”
“We’ve found a fag queer spying on us and he won’t give us any money or condoms.”
“What? Spying on us! Give him a slap, Pell, the dirty perv.”
I don’t know which one is “Pell”, but the one behind uses the scarf around my neck to pull me back
hard into my seat, half strangling me, and causing my hands to raise up to try relieve some
pressure.
“String him up, that’s what we should do. Take him in the woods and string him up.”
And with that, the female owner of this instruction reaches in and unexpectedly delivers a quite hard
and a certain bruise-making karate chop to the top of my thigh, causing my loud blurt, “Ow, fuck!”
“Would be a waste of good rope,” a different female voice chimes in. “Stick a log of wood up his ass
and chuck him in the river, that’s what I say. I wouldn’t mind his clothes before you do, though,” as,
with torch lights flashing, she reached in and tugged at the scrunched-up hem of my skirt.
“Oh my god,” she yelled. “I think he’s got a hard on.”
With that, I was summarily dragged out of the car, given a few slaps, and with my arms hoisted back
over my head, I was pulled backwards over the hood in such a way my pantied loins were thrust out
for all to see. The torches flashed and highlighted my plight. I was indeed sporting a half bloated
cock inside my panties. I felt two hands pull sharply at the waist-band and loop it under my balls,
show-casing my cock’s semi-hardness.
“He obviously likes it rough,” a male voice taunted. “I wonder how rough. Wanna see, girls?”
“Hell, yeah,” said the voice who’d delivered a sure bruise to my leg. “Go find a big chunk of wood
and stick it up his ass, Pell. Make the fag scream.” her tone in a horrifyingly genuine request.
“It’s all dressed up like a whore,” remarked a male voice, “maybe we should fuck it first.”
“You fuck it,” offers the other male. “You’re the one who’ll fuck anything that moves. Go on, I dare
ya.”
“I’m not into that gay queer shit. But this thing, it’s dressed up like a tart. It’s just begging.”
“Whadya say girls?” the other male voice throws down the challenge.
“Fuck it, fuck it, fuck it…” I hear two female voices start to chant in tandem, with a frighteningly
frenzied sense of purpose.
“Yeah, just look at it. It deserves my cock up its ass. OK, I’ll do it. Come on then. Flip it over and hold
it down. My cock is gunna go in.”
His words were effected bravado to impress the two girls, but his veiled fervour hadn’t fooled me.
He’d implied he was repulsed by “that queer shit”, but had jumped at the chance to go at me. The
pretext that I was due some kind of violation was bullshit. He’d been presented with what he
perceived to be a slut whore and, a penis in my panties or no, he was hell bent on fucking my ass.
And when the two girls would surely chant egg him on,,, well,,, I could see it would give him more
reason to try bang my brains out. I knew that when he got in there and set things right, he’d let rip
like a run-away jack-hammer.
All through their exchanges my cock had remained semi-engorged, despite the ominous thread of
their words. I was still being held with my arms back over my head, my back on the hood, my
exposed loins thrust outwards, and my heels barely touching the ground.
I was rasping with uneven low groans. Audible, guttural, throat-vibrating, moans.
Like a desperate man on the trap-door of gallows, who’d been stitched up by a kangaroo court.
I’d been cornered and conquered, charged and convicted, and sentenced to outrageous misuse.
I realised any protest to these scumbags would sound ridiculous and pathetic from my bone-dry
mouth and awkward posture, and most likely back-fire in a very disturbing and unhealthy way.
It was bad enough it appeared I was about to be broken-in and ridden by a demented, venge-crazed
mad-man who seemed to be half my age.
And as I mentally scrolled through what was probably going to be a humiliating, degenerate, possibly
protracted and an almost certainly very painful chain of events, my scarf masked my dry gulps, the
night hid my flush, and I fought my angst-riddled tremors.
But I couldn’t hide my cock and its lewd pulsing dance as it savored my impending ordeal.
Conditioned by dark muse it flagged its endorsement, and was bursting with mindless acceptance.
To my deep shame it was oozing with greed as it stood high in majestic erection.
“Just look at that …”, I heard a voice say. “I told you he’d come here hoping to find a cock for his ass”
“Nooo!” I groaned, in a weak, pathetic moan.
“Oh, yes, yes” I heard a voice hiss, as a hand slapped my face so hard I saw blinding white stars……
Several hands then seemed to be grabbing and twisting me all at the same time. I didn’t know
whether to lash out, resist, try throw myself to the ground or what to do. They really were like a
frenzied lynch-mob. At that moment, if one of them had said “I’ll go get the rope for after”,
I think I would have fainted.
Then a male voice called out, “Look!” and by reflex they all turned to the direction of his fixed gaze.
A vehicle was coming, or at least headlights were. It was like time stood still, and everyone froze in
mid pull, or push or whatever they were doing. I looked across too, stunned and open-mouthed.
Oh, crap! What now? I was already up to my neck in seriously deep quicksand.
Would I be saved from these feral, sick scumbags, or would my plight take a turn for the worse?
If these new hands were malicious and vindictive…. I was a sitting duck for any barbaric sport they
may decide to dish out.
Would I be “persuaded” to star in some kind of humiliating and degrading spectacle?
Would I become a bent-over captive for sordid amusement, as some took turns at my ass?
Would they jeer and mock as it became more sloppy and gaped with each painful and slimy
injection?
Would I be spit-roasted like a pig on a stick, and be forced to gulp down vile cum?
Would they leave me hog-tied and dressed like a whore for more torment by others who found me?
And what if these too started using my ass? It would end up like a big sloppy sinkhole.
As I helplessly envisioned these sickening scenes, I remained in blatant arousal.
My erection was mocking any claim to having self-respect as it broadcast the unconscionable truth.
I’d dressed myself up like a cheap easy slut and gone out with no phone and no backup.
I’d deliberately strayed onto notorious turf, and paraded my ass in the open.
I’d become overtly aroused when found out and captured, even more so when roughly manhandled.
My straining hard cock, now weeping with lust, knew exactly what I dressed and gone out for.
::--
To indulge in the rush of deep moral danger, flaunting my impulses outside the boundaries of safety.
But my hateful, sick demons hadn’t left it to chance when they consigned me to front Canrich Weir.
This seedy dark quarter was now a magnet of badness, A hell-hole with a grim reputation.
This once sinister cesspit was now the heartland of evil. So lawless, now a no-go for cops.
Oh, my demons chose well when they appointed my fate, and knew exactly what I’d be in for.
“Go to Canrich Weir,” my sick demons had told me, fully knowing what reception I’d find there.
My long due appointment. My most hellish of nightmares. The hosts of my abject defilement.
Sadistic cruel thugs who would treat me like shit. Evil scumbags who would beat me and rape me. -->
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