Be A Lady Tonight By Virgomars

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Warning! This story might contain activities that might not be suitable in selfbondage. Please play safe.

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Frankly, I was scared.

 

I've long had this thing about wearing sexy women's clothes (why can't people design really sexy clothes for men, like the 16th century doublet, hose and codpiece?) but I'd never dared venture out in public dressed as a female. Tonight, come what may, I was going to do it.

 

The problem is, I'm over six foot tall.

 

The rest's not bad though, particularly the legs. The legs are great, if perhaps a trifle over-muscled. The waist is pretty good too, just 32 inches round and not a trace of beer gut. But the hips are too narrow and dimpled to be truly feminine and the chest - well, you wouldn't expect much there, would you?

 

Just now my wife is away in France for a couple of days, so I'm on my own. I had a few weeks notice, enough time to hatch the plan, check the details and decide on an outfit. Now I was standing, nervous and naked, in front of the long mirror. The days had boiled away. Tonight was the night I would be a lady.

 

OK, start the reconstruction. The first task was a shave, as close as possible so it had to be a new blade. Then the enema douche, for reasons which will become clearer later. Next, opaque black open-crotch tights, with bum and hip padding formed out of carefully-shaped layers of thin foam glued together to give an impressive arse. 'Swell' is the word that comes to mind!

 

The boobs were next. I chose a fairly standard 38C white bra notable only for the fact that it has no seams across the cups and filled it with my patent boobs. These are made from water-filled condoms with the addition of a small hazelnut tied off in the teat end with thread. Then you pour in about a cupful of boiled water with a pinch of instant coffee to add colour and tie off tightly leaving no air inside. Cut off the spare latex and you have a flesh-coloured tit that moulds itself satisfactorily to any bra, has weight and bounce and a nipple that shows up well. Drop them in a basin of hot water for a few minutes to bring them up to body temperature.

 

At this point I broke off dressing and headed for the bathroom with a selection of buttplugs. One of the hazards of having a long lead-time on a scene is that you tend to keep adding things. I had fantasised about going out wearing my largest plug with a few tiny bells hanging from the chain in its base, so of course I had to go through with it (a decision I came seriously to regret). I like to work up through about three plugs stretching the arse in easy stages, and finally the big one was in place. It hurt like hell, but experience shows that the pain simmers down quite soon. I walked back to the mirror, tinkling gently.

 

And now for clothes. First, a pale grey figure-hugging high-necked sleeveless top and a necklace, then a black waspie corset to force the waist in another four inches (aaargh) and finally a black leather-look miniskirt tucked under the lower edges of the corset. No panties, you notice. My male equipment is rather on the large size and gives an obvious bulge in the front of a tight skirt like this one if confined in a thong, so I let it all hang out. Down, anyway. An additional thrill is that the skirt only just covers the end of my dick, so the slightest ride-up of the skirt (or expansion of the dick) would have me criminally exposed.

 

Boots next. Not quite stilettos this time, but a three-inch heel nevertheless. The heels are essential despite adding to my height since few men can walk like a woman without them. Perhaps even more importantly you sound like a woman from a distance, which programmes people to expect you to be one.

 

Finally the lipstick, eyeliner, eyebrow pencil and the big black wig. I was ready. I looked at the finished article in the mirror and was frankly unimpressed. The chin was too heavy, the nose too pronounced, the arms too long, the shoulders too wide and the ghost of a beard still just visible. It wasn't an attractive woman who looked back at me it was just me, in silly clothes.

 

That was rather a blow. Somehow I'd expected a small miracle of transformation to take place. It didn't help my confidence any, which was a pity as it was nearly time to go out.

 

The weather was cool and dry and already getting dark. I put on a short open-fronted jacket, picked up a shoulder bag and the car keys and set off.

 

The place I'd chosen for my walk was a small historic market town about half an hour's drive away, on the Welsh border. There was a single High Street of closely-packed shops with a crossroad at each end. Of the two side roads to the north, one was a long residential cul-de-sac and the other a more formal street containing Town Hall and some shops at the High Street end, a pub, a small hotel, some grand houses and the church, then smaller houses and cottages tapering off into open country. The two side roads were joined by a path through the churchyard. The plan was to park the car in this road near the church, cut through the churchyard, walk up the other road to the High Street, along the High Street and back down the first road to the car; the whole circuit about three quarters of a mile.

 

Although I expected the town to be fairly empty in an autumn evening I reckoned there was bound to be someone on the High Street. I wanted to see if I had the nerve to walk casually past some complete stranger, and note their reaction. Would they accept the disguise or stop, stare and laugh? What would happen if I was sussed by a gang of rowdy youths on their way to the pub?

 

I'd practised driving in heeled boots and found it was quite easy. I hadn't practised driving with a monster buttplug up my arse, and found it damned uncomfortable.

 

Just outside the town I stopped the car on a quiet stretch of road, fished a tight cockstrap out of my bag and clipped it on. This was another of those 'improvements' which seem like great ideas at the time but are probably ill-advised. Getting an erection would of course be disastrous, but the way I felt at that moment it seemed pretty unlikely. I was nervous as the proverbial kitten. I climbed out of the car pulling at my skirt which had risen almost to my waist and teetered up and down the empty road until I felt calmer.

 

Very soon after that I came to the edge of town and rolled the car slowly in past scruffy housing, betting shops, Police Station (!) and a municipal car park with public toilets. If I needed to go to the loo, would I dare to use the Ladies? The corset and the nerves together were making it seem a possibility! I drove on, found the first crossroad and turned north. It was about eight o'clock at night and there were a few people about. The street lighting was a lot more efficient than I'd imagined, too.

 

The first thing that went wrong was that there wasn't a parking space near the church. The only space I passed was just a little way along this street, quite near to a late-opening general store which was still doing desultory business. I turned the car, slipped into this space and switched off the engine. Immediately the interior lights came on revealing me tugging at the front of my tiny skirt.

 

I waited in the car until the light had gone down and the street was empty again, then quickly climbed out, adjusted my clothing under cover of the car door, locked up and set off in what I hoped was a normal manner towards the church. Tap-tinkle, tap-tinkle, tap-tinkle. The light grey curve of my boobs with their pronounced nipples showed up startlingly against the other dark clothes.

 

There were a few lights on inside the church, and an electrician's van parked on the path by the big gothic porch. I slipped past on the grass, trying to make as little noise as possible. The churchyard seemed to go on for ever and the lighting was terrible but I wasn't complaining about that except when I nearly twisted my ankle.

 

The next road looked eerily deserted when I got there, so I started off up it. The old houses here were built up to the back of the narrow pavement so I was walking right past their ground-floor windows. Several were lit, some not yet curtained. I was getting more and more jittery and my arse was getting more and more sore with every step. Also one of the toes in my right boot was chafing and I could feel the strain in my leg and bum muscles - I'd never walked so far in heels before. And my midriff was being slowly strangled. I had to force myself to go on.

 

There was a corner ahead where a side road joined, with a little triangle of paving and a bench under a tree. I thought I'd just go as far as that bench and then perhaps turn back.

 

Sitting on the bench to rest my legs gave me a moment to think properly. Here I was in the middle of a strange town miles from home, dressed up like a tuppeny tart in high heels and miniskirt without a stitch of male clothing and with no money, no panties and no sense. What on earth did I think I was doing?

 

Here I was, nevertheless, and from where I was sitting I could see up much of the remainder of the street. Nobody was about. So, very cautiously, I went on. Don't panic, don't even think, just keep putting one foot in front of the other. Tap-tinkle. My heels seemed to make an incredible noise in that silent street.

 

After only a few yards I thought I heard voices behind me, coming from the side road. I froze, but whoever it was never appeared. I was conscious that people might be watching from behind their curtains, or at least listening, so I resumed the walk.

 

I slowed as I came up to the High Street to look around, then stopped dead. A woman on the other side of the road had started walking straight towards me! Panic! I pretended I'd come to the wrong place, looked around, turned away and slowly ambled back down the way I'd come, trying to look casual, hearing her footsteps closing behind me. I walked a little quicker. The pursuit suddenly stopped and I heard a car door slam. For the first time I ventured a quick look back, to catch a glimpse of her car driving away. It hadn't been anything to do with me after all!

 

I'm not very proud of what happened next, but the terror of nearly meeting that woman face to face had finally destroyed my shattered nerves. I just went on walking as fast as I could - back down the road, back past the bench at the side-street, back through the gloomy churchyard and out into the brightly-lit road where my car was parked.

 

And there was a man with a dog walking down the pavement in my direction! The car was quite a way beyond him and I was already walking briskly (tap-tinkle tap-tinkle) so it would have looked wrong suddenly to stop and retreat. Besides, he was probably taking the dog into the churchyard. There was no escape this time. I crossed the road so as not to tower over him as we passed, hoping I would look more in scale at a little distance. He glanced at me once, then went on watching the dog. No frown, no puzzled stare, no curiosity. For him, I was just a woman walking up the other side of the street.

 

So you might say the plan had finally succeeded. I was quite elated as I dropped into the driving seat, then gasped in pain as my weight came onto the buttplug. The drive home was agony.