A Night Drive

Story Info
A crossdresser goes for a night drive. He's soon interrupted.
2k words
3.84
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13

Part 1 of the 2 part series

Updated 06/09/2023
Created 09/27/2018
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My heart was pounding; my parents had finally, finally, left. On date night, they might be out of the house for four hours, maybe more. It was more than enough time for what I had planned. They were standing by the curb, smiling as I waved to them from the veranda. As they took off and drove, my body quivered with the thought of what I'd do next.

The second their car was out of sight, I was racing to the garage. The least visited part of the house and the best place to hide my contraband. The grey black darkness of the place enveloped me as I pushed the shutter door open. The place used to be big enough to fit a car, but now worked as a storage place, filled with piles of old memorabilia and furniture we hardly used. Inside I rummaged for my gear, hidden in a compartment in an old wardrobe. There was so much of it, they had to be stored in several plastic bags. I carried them all upstairs feeling giddy.

I ran past the bathroom, my parents' room and the carpeted dining area, and dumped all the bags onto my bed and began pulling out the clothes. Today I was going all out. Out first came the lingerie, a pair of flesh-coloured panties and bra. I was nearly shaking as I slid them on, savouring their feel on my body. A pair of breast forms, a modest C cup, appeared from another bag and I pushed them into place, letting them sag against the bra material. A pair of white stockings were used to cover my ugly leg hair, and a white boned over bust corset, feminine and layered with ribbons, constricted my body until all I could take were short breaths. The steel jutted above my fake boobs beautifully.

Next on my oh-so-important list were my clothes for the night. I'd picked them out online several months ago, and only now was I getting to try them on. The day they had arrived I almost blew my load thinking about what I would do in them. The first piece was a satin, white crepe blouse with long sleeves and a shiny jewel in the neckline. It was silky smooth, and I put it on and marvelled at the way it made my body feel. Even with just a blouse, my top half was already looking deliciously feminine and soft.

The next item pulled out of the plastic bags was my favourite. It was a hobble skirt, so long it reached down to the end of my calf, with an inherent tightness that hugged my curves. It zipped into place easily and had a black and shiny aesthetic that came from being made of suiting twill. The hem at the bottom was so tight, that when I tried to walk in it, it constricted my steps into the shortest of dainty hobbles.

The rest of my outfit was quite typical. First was a pair of leather patent thick-high ankle boots, with stiletto heels and hardly any platform, which required me unzipping and hitching my skirt up to get on. A long blonde wig from the bags kept any sense of my male hair hidden, and, instead of shaving, a pair of white latex opera gloves were used to conceal any hair not covered by the sleeves of my blouse. Then, not wanting to waste time, I rushed into the bathroom and pulled several packages of makeup from the drawers and used them to target my face with puffs of blush and concealer. Finally, eyeshadow and thick strokes of mascara were applied to highlight my eyes. By the end I looked almost passably feminine.

Before going out, I had an urge to admire myself. I stared at the bathroom mirror, swishing and twirling my body for the view. The cute girl in front of me looked like the perfect little secretary!

The face in the mirror smiled, then sighed. Crossdressing was my biggest fetish, one that could only be pursed when my parents were gone for their cushy date night, but bondage was my end goal. I had always wanted to be tied up, to moan and struggle as the helpless damsel captured by the bad guys on television. It was a shame I'd done nothing to follow the dream. A poor social upbringing kept me from joining a kink group, and having never been good with ropes, I hadn't ordered any self bondage toys online.

It was a happy thought, but an unfeasible one, so it was abandoned. Knowing everything was ready, I headed for the front door and opened it. Outside, it was dark enough that walking to the blue Subaru wouldn't identify me, but light enough that my silhouette might. As hastily as I could manage, taking short steps thanks to my hobble skirt and the ridiculous height of the heels, I fumbled in the night in search of the car doors and ended up in the driver's seat after ten minutes.

I was ready to enjoy my night drive.

----

My drive began pleasantly. For the first ten minutes, I cruised around the beach-side roads, watching the sea. Some men and women remained on the sand long after dark, walking together or prancing and splashing around in the ocean.

I kept going, loving the drive and all the freedom I felt it gave me. I checked the mirrors again, which were tilted more towards me than to the dangers of the road and smiled. The makeup had not drained out, or left my face parched, and I still looked sexier than I'd ever imagined.

But it had been just too good to last. I had been forced to park at the curb and remained there stewing in anger knowing my drive was over. It was ridiculous that a breath test had been set up this close to home.

Attempting to remain calm, my fingers jittered against the wheel as the Police Officer found time to get out of his vehicle and approach me. Through the view from the rear mirror, he looked to be in his thirties, with a chiselled face and brown hair, with a uniform that packed out his figure nicely. At this hour, there was no one else visible on the road.

As I unrolled the window, he raised a brow, like he'd come to a decision. 'Do you know my I pulled you over, Sir?' He said curtly, and my face wilted when he saw so easily through my hour-long preparation to cross dress.

'Was I speeding, officer?' I asked, attempting the most feminine voice I could muster. It ended up sounding like a choir tenor.

'Not at all.' he said, rather quickly, as if he knew I'd been cruising at fourty kilometres the whole drive. 'Are you currently on female hormones?

I shook my head. 'No Sir, I was about to start in a couple of weeks.'

The officer signed. 'Then I'll use your preferred pronouns. You see Ma'am, non-transitional crossdressing has been illegal for the past two years. Please step out of the car.'

For a moment, I hesitated, still shocked at his use of Ma'am. Then, with my head kept thoroughly visible, I followed the officer's instructions. My heels clicked as I stepped onto the asphalt.

'Please place your hands above the car door, Ma'am.' He said more gently. Still surprised by his use of Ma'am, I placed my latex-gloved hands above the car door and waited. Abruptly, he began to touch me, to feel my body, sliding his hands across my satin-covered back.

'Do you have any contraband on you? Any illegal substances or knives?' He said, sliding his hands across my chest. He began caressing me, slathering his hands over my hips and my groin and my fake breasts. After a moment he pinched my tits, then reached for my bum and squeezed that.

'No, officer, not at all.' I said, surrendering any attempt at a female tone.

After a moment, the man stopped, and grunted. 'Now please keep your hands above your head.' Doing as commanded, my hands were soon brought to the small of my back and held there. There was a pause, one that felt far too long, before hard metal graced my wrists and I heard a euphoric click tighten against my latex gloves. My cock began to form a tent under my skirt as I struggled instinctively against the cuffs. Forcefully, the officer adjusted the cuffs further down my wrists and tightened them.

I tried one more buck at the cuffs, but they were too secure. At least the soft satin and latex from my long-sleeved blouse and gloves kept them from biting my wrists too much.

Thinking it the end of my trouble, I turned towards the police van, when suddenly my arresting officer brought up his hand. 'I'm sorry Ma'am, but I'm not finished.' He said, then walked back to his vehicle.

To my surprise, the officer didn't bring back forms to sign or deal with, but a long cord of nylon rope. 'All crossdressers are to be effectively restrained during transport.' He stated before I could ask what its purpose was.

A loop of chord was tied across my wrists below the handcuffs, then wound tight and tied off. By the end, its strength was severe, and I struggled to move my arms more than an inch. Another knot was fastened below my elbows, pulling my arms together in a stringent tightness more powerful than an armbinder. More rope was looped around my chest, placed above and below my breasts, making my cleavage push and protrude against the satin of my blouse.

As a finishing touch, the handcuffs were removed, and another lashing of rope was fastened over the last of my gloved wrists. There mustn't have been a single part of my gloves not wrapped in rope.

In a daze, my wrists and elbows securely bound, and my ankles already constricted by the hobble skirt, I was led to the back of the police cruiser. The Policeman was patient, motioning me forward at a gentle pace as the hobble skirt forced me into petite and dainty steps, and when we came to the car door, he generously helped into my seat. I muttered a 'Thank you' as he adjusted the folds of my skirt.

Just when I thought it was over, the officer didn't start driving, but instead brought out another chord of rope from the boot. 'For your ankles.' He explained.

It seemed ridiculous to insist on tying my ankles when I wore a hobble skirt, high heels, and was already secure in the police cruiser, but by now I was resigned to my bondage, and soon the policeman was tying my shiny black boots together in a complicated knot. He cut it off, cinching it, and my boots were fastened so tight together there wasn't a centimetre of slack.

Unable to move even half an inch on my seat at that point, I was confused when the officer brought out one final chord of rope.

'Officer, what's that for?' I asked.

'Your final restraints, Ma'am.' He answered. 'Please lie down on the seat.'

I fumbled downwards, constricted like a tied pig already, but with help from the officer, I was lying on the car seat chest-first, and after some more work, lay with my ankles tied to my wrists in a perfect hogtie. No part of me could move, and, satisfied with his procedure, my arresting Officer took the driver's seat.

Then the driver's door shut, and the engine started.

Totally trussed up and left alone, I began to panic. The rational part of me feared what were they going to tell my family, encouraged me to consider how much trouble I was in, how were they going to sentence me, but another side was delighted. Here I was, bound like a Christmas present in a position I'd never be able to achieve alone, dressed as the woman I'd always wanted to be. Instead of worrying about what I couldn't possibly control, I let the temporary nature of my situation take over, fought playfully and fruitlessly against my bonds, all struggle cushioned by the leather seat padding and the softness of my clothes.

I was only aroused more and more as we drove on, heading towards the station to be taken into custody.

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AnonymousAnonymousabout 4 years ago
night drives

I am a married closet crossdresser. My wife is often away visiting her family. It's my opportunity to get fully dressed as a female and venture out. I love saying goodnight to her on the phone with thw thrill of her not knowing she is talking to a fully made up transvestite . Once the call is over I finish getting ready and head out in the car. I do not take any male clothes which I did the first couple of times. I enjoy going for strolls daring myself how far to walk. I have parked in a number of towns and done some window shopping. I have never had close contact with anyone, but I do have fantasies like the one in this story

BrendaNWBrendaNWover 5 years ago
very good start

Intriguing story so far .. please continue

MarieJoanneMarieJoanneover 5 years ago
Hot

A gorgeous, terrifying predicament. I too have driven crossdressed. A sensational experience xxx

AnonymousAnonymousover 5 years ago
In lingerie

I began wearing women lingerie and clothes when I was 13.because lingerie is made from a different material guy and looked down on for wearing women lingerie.I'm proud to say I enjoy wearing women's lingerie and clothing.I'm married and straight so till you have trued wearing women's lingerie don't put us down for doing it

AnonymousAnonymousover 5 years ago
To short

Was a nice start. Needed more though. Hopefully this is just a first chapter

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