Ok I was board - hotel alone, and the chance to dress. So I decided to spice up the night I would go out in my car for a ride dressed. Always wanted to try it and my sense of adventure gave me the confidence. So on with the black lacy top hold ups , lacy black panties, bra, my black dress and a pair of jeans and my long coat just so as I could get past hotel reception without being noticed.
When I got in my car I squeezed out of my jeans, and headed of, and as soon as I found somewhere to pull over, I got my wig on and applied some makeup and lots of thick red lippy. Popped on my flats to drive in, and had my heels on the chair in case I decided to go for a walk. Handbag by my side and of I went.
I had no idea where I was heading so just drove off into the night. It felt so good to be out dressed; I kept catching a glimpse of my face in the mirror and enjoyed this slice of freedom. I looked down to see my legs, raising my skirt so I could just see my stocking tops and I kept catching a glimpse of my face in the mirror and I felt free, fem, and it was a good feeling.
The layby was empty, so I pulled up and switched of the engine. I had never tried dogging before, and to be honest I am not sure it was for me – liked the idea – but the reality of meeting strangers our dressed was scary. I loved to dress, and had many fantasies about meeting with men, but that's as far as I got. So, I sat in the car and just as I was about to head of back and call it a night, I thought - why not try a walk. Whilst is had been raining, it was showers so I could chance it, and there was no one about. This is my chance; just to try it and see how it feels outside in the cool night air. What it would be like, walking outside in my heels, short skirt, and wind blowing across my stocking clad legs? Shall I.. Shall I go for a walk. Shall I get out my car dressed as a woman. What the hell. - spur of the moment and before I knew it I was outside, pulling on my heels.
I reached for my handbag and there was an umbrella in the boot of the car, as it was drizzling I thought I best get it . I had my car keys in my hand, the handbag in the other hand, so I went to the boot and at the time for whatever reason I placed the car keys in the boot as I picked up the brolly and yes , you guessed it. I shut the boot and locked my car keys in the boot of the car. And yes like a fucking idiot, I locked myself out of my car. I must have locked the doors with the fob by accident whilst the boot was open. Shit,, shit,, shit,, what now. I froze, panic, shit no - A second ago I was safe in the warm car having a day dream about going for a walk, and now I was stuck outside my car, dressed and faced with a dilemma. Walk back to the hotel, change, and ring the RAC. But it was at least 10 Miles away and I was in heels - and I had no idea where I was.
I had my cigs in the handbag so decided to have a fag and think about how I was going to get out of this situation. This was a company car. I had a business meeting first thing and I was stuck dressed like a tart in the middle of nowhere locked out my car. How would I explain this one. - and I suppose to anyone driving passed all they would see is a woman smoking a fag with a brolly in the rain stood by a car. I finished the first fag and no further forward with a plan, I felt like crying.
The lights from the truck almost blinded me - and I was stood starring - shit - shall I hide - walk away - I crept round the front of my car and like an idiot ducked down . The trucks engine rumbled to a halt and I just sat there, crouched down hoping it would just pull away.
"Are you ok love" - he shouted - should I answer - "err yes " - I heard the cab door shut and footsteps approached - ok - here goes I thought – yes – a plausible excuse … I am coming back from a fancy dress night and have locked my keys on the car boot - perfect - I stood up and he
approached me. He was a big guy and smiled at me as I approached - "what’s the problem" - I explained my situation - and he just looked at me smiling. Ok he said, don't worry, I understand, look it’s simple – you’re a tranny, and may I say you’re not bad, better than some I have met here over the years. Is it your first time, I know you’re looking for cock - so why not just forget the bull shit and let me sort you out. Come on, round the side of the cab. Come on, NOW- he shouted at me, almost ordering me .. I hesitated - get your ass round her now he shouted. I followed him, and he stood by the side of his lorry. As I approached, he was unbuttoning his flies. Ok - get on your knees love. Sort me out - and I will help you out. "what do you mean" I asked - - " look" he said, " get on your knees and if you do a good job I will get your boot open for you so you can get your keys - I used to work for the AA and know how to get the mechanism open going in from the back lights - will damage a light - but will avoid more embarrassment for you - come on he said, the quicker you empty my balls, the quicker I get you back in your car – or whatever the fantasy is ….
" So - I walked towards him, lowered myself onto my knees, and placed my bag on the wet floor to kneel on. His cock was already out, and he was working it in his hand - at least 7 inches .. So before I knew it I was sucking on his cock like a slut - and I felt like a cheap whore - in the drizzly rain sucking and slurping on a cock. I was enjoying it as well. "Ok bitch" he said - "here I cum"... he pushed hard and emptied himself into my mouth, working his cock hard with his hand to make sure I got all his cum, and there was a lot.. "Jesus" he said, "you are good, and I needed that"... I felt the warm sticky cum hit the back of my throat, my first time and it felt good, but tasted horrible…
As soon as I felt him release his warm jet of cum inside my throat he pulled out his cock and did not even hang round to tuck it back into his trousers before he was climbing back into his cab. He turned and just smiled – thanks for that love – really needed it, and of he went. No “road side assistance”, not even a kiss goodnight – I could not believe it, what a fucking idiot I was – he has just conned me into a blow job, fucked my face and now he is fucking of.
So here I am, same situation but with a mouthful of lorry drivers cum. As he pulled away, I thought I best get up, as did not look to good on my knees dressed like this now the lorry was not hiding me from the road side. I stood up, brushed myself down, picked up my handbag and toddled back to my car, and tried the doors again in the vain hope that it would suddenly open... but no, still locked. I could see my wallet and phone on the car – how annoying.
I went through the options again – I could try and find a cab and play the fancy dress card again to avoid any undue assumptions, or just put a brick through my passenger window and open the boot from the button in the car. Not sure if it would work, or would the alarm go of – who knows – or maybe I could try and get the window down slightly and get a stick and try and push the unlock button – yes – that seemed to be a good idea – why the hell did I not think about that before sucking the big man off in the lorry … However – one catch – I was dressed in a short skirt, wearing heels and it was starting to rain now. Anyway – not wanting to waste any time I walked across to the edge of the layby and started looking in the bushes to see if I could find a suitable stick.
After a lot of fumbling in the bushes I came across a suitable “tool” and went to the car and started to try and force down the window. Not much luck there – now it looked like I was trying to break into a car. Just as I thought I was getting somewhere a car pulled up behind me in the layby. That’s all I need. Shit… This time, two young lads got out the car and as quick as a flash they were approaching me on foot asking if I needed a hand. Their headlights were on and I was dazzled and had to put my hand over my eyes to see them as I watched them approach... It won’t take them long to realise that I am not a “damsel in distress” – and then what. So I opted for the fancy dress story and as soon as they got close with my deepest voice I started to explain the “you won’t believe this but” story and boy were they disappointed. Fuck me, you look good for a bloke in a dress one of them laughed, we only stopped because we thought you were a tart. He laughed, - nice... I thought,
The other guy was not so put off either and he pulled out his phone and took a picture of me. You seem to have made a lot of effort for a fancy dress party he said, make up, heels – is that your own hare darling.. , you look like you have done this before – very convincing – I was flattered – thanks I replied, now any chance you could give me a hand – or at least can I borrow your phone to ring the RAC. What’s in it for me, he replied. Sorry, I said, what do you mean, … look he said – if we help you out, what’s in it for us ? – us now,, look I said, just leave it- if you can’t help me then you may as well drive off – I have no money on me, but happy to give you a few quid for your trouble once I retrieve my wallet – hey have you any idea how to break into a car. What you think we are car thieves now he replied, this time he was not laughing. They both just turned back and walked of their car. They did not pull away, they were just sitting. I was starting to get a little unnerved now – what where they doing – probably posting the picture of me now on some internet site .. Then a thought struck me, I hope this is not some dogging layby – that would just be my luck. On a different day I suppose it could be quite exciting, but I am now not in the mood for anything other than getting out of this fucking mess.
Whilst they were young, maybe about 18 or 19, they were 2 and they looked like trouble and I was wearing a dress with heels. I could possibly handle one of them in a fight but not both together, and who am I talking, I had never had a fight since I was at school !!...
I returned to the task of trying to get the stick and just kept on with it, and soon I managed to get the window down slightly. At last I am getting somewhere, then some more, and then I could just about reach in. I was filly immersed with the task in hand, now oblivious to the 2 young men in the car when I felt someone grab my arm from behind. I panicked, but before I could do anything, he had both my arms locked behind me and was pulling me over towards the boot of my car. Jesus he was strong. Listen love, just do as we say and this will be over quickly. You’re too good an opportunity to miss. We know you want it, else why would you be here and also dressed like a slut. Too much of a coincidence. Before I could say anything in return, he had a rope round my face and had me gagged. And then he tied my hands tight and pushed me face down over the boot of my car.
Within seconds the other lad had a rope round my left ankle and was busy securing it round the car and onto my right ankle, and then he managed to get some more rope round my arms, through the rope he had already tied round my head and was pulling that over the car so I was literally strapped spread eagled to the boot of my car, and it was pulled very tight. Shit, I was fucked now, what the hell .. And before I could come to terms with my situation, the other lad was parking his car to the side to obscure me from the view of the main road. This is like some kind of rehearsed military exercise. Then I felt the cool night air against my panties as he roughly pushed my skirt up and over my back, and he started to slap my ass with his hand. Do you like that love, he laughed. Shall we give you a spanking first.. You are a naughty girl , coming out dressed like this. Then something cold between my legs and he had a knife, shit, he had a fucking knife, and was using it up rip open my panties. Hurry up, one of them shouted, let’s make this quick – I will film it on my phone – you can go first.
I could not even scream with the rope tight across my mouth, and I felt him pushing his hard cock against my hole, he spat down to lubricated himself, and proceeded to drive his hard cock inside my exposed ass, and he just fucked me very hard, quickly - I tried my best to move away – it was no use and it felt like he was fucking me bare. It was now raining hard, and I was in pain, as he pushed himself deep into me. I had never been fucked before – mind you I had often fantasised about it, but this was not how the fantasy went (not in the rain lol) He came quickly and I could feel the warm sticky cum seeping out of my hole. The other lad passed him the phone as he got into positon. Now you will feel it he said, john is much bigger than me, but at least I have lubed you up well sweetheart.. John was much bigger than him, fuck me it hurt, but I as he fucked me, I my cock was starting to pulse against the car boot as he forced himself inside me and soon I felt like I was going to cum as my cock rubbed against the coldness of the boot of the car. Look John, I think she is enjoying it.
John pulled out and exploded all over my ass and roughly rubbed his spent cock against my ass cheeks.
They both retreated and just stood and looked at me.. What now, I could hear them saying. Then one of them walked round to the driver’s window that was now partially open. Look let’s take his wallet – and the bastard reached in, grabbed my wallet and started leafing through the various credit cards etc. ..
Look, here is the deal, we will let you go and you get your wallet back. We will un tie you, and you will , on film thank us for fucking you, give our cocks a final suck and then we will drive of and promise to throw your wallet out of the car. We will take the cash as payment – and they laughed. What choice did I have.
Soon I was staggering of the bonnet of my car. My ass was sore, cum dripping down my stockings. My own cock was now visible as my panties were gone. I tried to arrange my dress – but then one of them shouted – we want your dress off … take it off, NOW… but it’s raining – We don’t care – we want you on your knees in just your bra and stockings – come on bitch – time to suck our cocks. I had no choice but to agree – and to be honest I was now past caring. I needed my wallet back, and needed this to end. They were both stood behind their cars with cocks out waiting for me. Hurry up bitch …. I staggered towards them, pulled my dress over my head and shivered in the cold and soon felt the rain on my naked flesh. I got on my knees, this time not caring about putting my bag down first, I just wanted this over. I proceeded to suck them of, one at a time, cocks were soon hard and I was sucking and gagging as they face fucked me furiously in the rain. I could taste the rancid mixture of salty cum and my own shit from my ass that they had just fucked. The first one deposited his cum inside my mouth and it went deep to the back of my throat and whilst I tried to spit it out, it just dribbled down my mouth as I was quickly filled by the next cock which did not take long to unload as he had be wanking it while he waited.
10 minutes later I was running up the road chasing their car in a bra and stockings. I had taken my heels of, and my wig had already gone the journey when john pulled my hair in the heat of his orgasm as he was cuming in my mouth. They both went into hysterics, and the other lad was filing the whole episode on his phone. The wig was just chucked away and was by now lying in a pool of water by the road side. They were true to their word and did chuck my wallet out of the window, but unfortunately they decided have even more fun with me first. They drove of very slowly and enjoyed the spectacle of me chasing after them. They would stop and let me catch up and then pull off again. Luckily there was no other traffic as by now it must have been around 2am in the morning. Finally they stopped the car and the one called john got out and had my wallet in his hand. Come on love – here you are .. He held it out and I ran towards him. He dropped it on the road and got back into his car and then sped off into the night.
That’s when things took a turn for the worse……..
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