One Earned Night

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The story of a well earned evening.
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Ever since my escorting had taken off I had been lucky to meet some really nice guys who had not only paid good money for my time and attention but had treated me to not only great sex in some cases but gifts and money as presents helping me get the lifestyle I wanted.

Now I guess I had been lucky after hearing many horror stories, I had heard of girls like me being hurt, raped or worse but for me I had one very special guy as a back up. I had always used a taxi company in town calling themselves Pink Cars they catered mainly for the gay community and only ever advertised themselves to the gay community which made them perfect for me.

On several occasions I had ordered my taxi and my driver had been a really cute guy called Matt who had not only made sure I was always safe but always hinted at the fact he liked me, to be honest having a guy tell me he kind of fancied me was different. Over time Matt and me had become good friends and the last time I had seen him he had given me his mobile number in case I ever ran into trouble with a client.

Of course the guys I met I had always checked out and made sure I was going to be safe with them but it was nice to know that Matt would be there if I needed help, in fact on my last appointment I passed my client Matt's card and got him to call my taxi via Matt's own mobile number. After all I had promised him a date and as I still felt hot and horny I decided tonight would be Matt's lucky night.

Minutes after my taxi was called the phone rang on my clients desk and as he sat by my side I said hadn't you better answer that, reluctantly he stood and walked over to his desk and first checked the caller id before answering the call, I guessed he wanted to check it wasn't his wife or partner. Lifting the handset he didn't say a word before placing the phone back into its cradle and saying to me its been a beautiful evening Lisa I do hope we can meet again but right now Matt is downstairs waiting for you and with that he escorted me back to the lifts before kissing me gently and politely on the cheek.

Soon I found myself stepping out into the dark and cold of the night slightly concerned of whether anyone could be around but as I took my first few steps I saw Matt, he looked as good as ever in a nice smart pair of black trousers and a obviously freshly ironed shirt with his muscular torso evident even through his clothes.

As we met Matt turned so I could take his arm and as I did he asked so how is my favourite girl, simply but politely I said im fine thank you.

As we reached the taxi a normal saloon car type Matt released my arm and held open the back door for me but as he did I quickly asked can I ride up front tonight and with that he didn't say a word as he pushed the back door closed and opened the passenger front door for me. As I went to step in I brushed my outstretched hand across his side and as my fingers met his hard torso he went to speak but I stopped him by just saying thank you sexy.

As he pushed the door closed he turned to walk round the car but as he did I noticed what seamed to be him considering what I had just said. Eventually his door swung open and he took his seat not saying a word to me as he inserted the car key and started up the engine with a diesel clattering noise, at last Matt said to me so where are you headed and again I caught him off guard as I said how about your place.

I half expected Matt to be thrilled at my suggestion but as he pulled on his seatbelt he looked over to me and said how's about a drink first, accepting his idea I told him I wanted to go home first so I could grab a few bits and make myself look at my best if we were going to a bar. Besides I wanted to make sure Matt got what he wanted.

Soon we pulled up at my place and as I stepped out I jokingly said leave the meter running Matt I will pay in kind later, I was glad to see him chuckle at my comments and as he put the window down to reply he said do you mind if I come in.

Slightly taken aback at his suggestion I thought why the hell not and quickly agreed and as soon as I said yes his door was open and there stood all 6 feet 2 of handsome ex soldier with a body to die for. As he stepped toward me I headed up the steps to my front door and fumbled in my purse for my keys but as I did I felt Matt's hands clamp round my waist and then his body tight against my back and a nice bulge eager to be released pushing at my more than willing butt.

Now I knew he wanted it as bad as I did and I knew exactly what to do as I swung the front door open I swung myself round on my stilettos and faced Matt looking deep into his eyes, reading his every move and thought as his eyes ran across my body. Within seconds his hands locked onto my waist again but this time I pushed my body against his letting him feel my semi hard cock in my panties rubbing against his thigh as I kissed him gently on the lips before breaking away and stepping inside.

As I wandered into my lounge and kicked off my stiletto heels Matt made a move for me again and like any girl I let him catch me in his muscular arms but this time as he went to kiss me I placed a finger across his lips and said wait here for me.

Telling Matt to make himself comfortable I snuck off to my boudoir and peeled off my almost skin tight mini dress and all my lingerie till I was butt naked and looking a little more flabby without my fully boned corset on, as I relaxed I removed my wig and sat and removed all my makeup with cleansing wipes before heading off to get a hot shower.

The shower felt fantastic after having a slightly over weight and controlling guy using my body for his pleasure and my financial gain, but now I was clean and now it was time for my pleasure to begin.

Stepping from the shower and heading out of my en suite back into my room I knew exactly what I was going to wear already and quickly removed a steel boned black satin corset and lace panties with lace top seamed vintage stockings from my drawers, slipping into my silky feeling stockings and lingerie already had me panting with pleasure and as I picked out my dress a deep purple coloured clingy satin mini dress I was well aware of my girly cock hard in my lace panties

Sitting in front of my dressing table I carefully applied my layers of make up and foundation making each stoke of the brush perfect and wiping off anything less as I wanted to look at my very best.

Soon my makeup was applied and my mascara perfect with my long eye lashes giving me a rather androgynous look as I sat dressed with no wig on. Stepping from my stool I went over to my big wardrobes and slid back a door where I kept my selection of wigs all pre brushed, styled and ready to wear and after a moments though I took out one of my favourites a raven black shoulder length number that fell away just over one eye making me look very convincing.

Now there was one last piece to complete my outfit and that would be my heels, now like a lot of genetic girls I had a selection of around 30 pairs of stiletto heels and high heeled sandals along with some Pvc thigh boots for kinky sessions or when I just wanted to be fucked senseless. Finally I decided on a pair of black satin peep toe stilettos with a 4 ½ inch heel that I knew would be not only comfortable but very sexy with my outfit and even better with my corset and stockings for later on.

As I made my way back into my lounge I swung open the door and stood myself in the door way and as Matt looked round at me I just said im ready lets go shall we. Obviously Matt didn't need a second invitation as within a split second he was by my side once again escorting me to his car and holding the door for me like a perfect gentleman.

As I sat waiting for him to get into the drivers seat I noticed he had left the meter running and as he took his seat I jokingly said well that's enough for a whole night of fun and with that he pressed a button and blanked the display setting it back to zero. Jokingly he turned to me and said well I hope I can keep you up all night especially looking as good as you do, blushing I thanked him and once again the clatter of the diesel engine stammered into life and we were on our way.

As the journey went on I started to become worried as I noticed Matt was definitely not heading into the town centre and the gay district as I had expected, soon enough we pulled up at a gate to industrial looking building and Matt got onto the taxi cab radio to who I presumed was an operator and as he did the gate swung open. Slowly the car rolled forward into a dark and deserted looking yard and Matt pulled up and switched off the engine.

Right now I didn't know whether I could trust him or not and I had to guess he realized as he turned to me and said you sit here for 5 minutes while I go sign out for the night, suddenly I realised this is where Pink Cars operated from and then Matt was gone.

As I sat in the quiet and dark of the yard I was still scared of this place, it definitely didn't look like the kind of place you wanted to spend much time alone. As I sat there I decided to take out my mobile and go through some emails just to pass the time but as I got into reading a new mail from another client there was a knock on my window that made me jump in my seat, looking round Matt was stood there waiting and as I pulled the door handle he opened up the door and helped me out.

As my eyes adjusted to the dark I saw another person someone I hadn't seen before stood behind him but as Matt saw me looking past him and trying to figure out who this other character was he said this is my mate Sally she is going to take us into town so I can have a drink as well, quickly Sally stepped forward and reached out her hand saying hi so you are Lisa.

Taking her hand and shaking it gently she almost crushed my fake long finger nails with her grip and looking her over with her shaved head and next to no bust at all I quickly assumed she was the typical butch gay girl. As Sally led us to her car she blatantly ignored me but said to Matt you were right she is stunning and that was the last words she spoke until she asked where we wanted to go.

I had no idea where Matt even lived so I decided I would leave it up to him where we went and with that Matt said drop us at Bar 61 please Sal and with that we were being whisked through the back streets at speed back into the town centre, I was glad I had never had Sally drive me before as to be honest her driving made me uncomfortable along with her lack of communication skills she wasn't exactly a people person.

As Sally dropped us off and we stepped out I thanked her and she replied yeah ok and with that I closed the door and Sally sped off like she was in some kind of race. Taking Matt's arm I said Sally doesn't like me or my type does she, and he simply replied ignore sally she is always a miserable old cow to be honest and no body is going to change that but she is my boss im afraid to say so I have to put up with her bad attitude on a daily basis.

As Matt lead me into the bar I was well aware it wasn't a gay venue and in fact it was one of towns more expensive wine come champagne bars and as we made the entrance a member of staff greeted us and Matt simply said a table for 2 and with that we were led inside. The bar was beautiful with lavish furnishings and fittings making me all the more nervous despite visiting some of the areas better venues to meet clients I suddenly felt like everyone was watching my every move as Matt escorted me to my seat.

As we sat chatting Matt ordered a nice white wine with glasses, I sat trying to adjust to my setting and looking around all I could see was towns wealthier clientele one or two of which I had the pleasure of meeting on a professional basis. Looking to Matt I said I didn't expect you to bring me here I kind of thought we would do a gay bar or two and then maybe a nightclub, for some reason Matt looked surprised at my comment and quickly said to me you are worth it looking as amazing as you do.

I tried my hardest to enjoy my evening out but as Matt went off to the toilet a guy who I had recognised approached me and said do you remember me Lisa, nodding and smiling I said of course I do Paul. Paul was a well off business man who lived the penthouse life in the town and we had met via my escorting a few weeks back and had mind blowing sex on his balcony over looking the beaches and sea.

I wasn't sure if he was here with someone but before I could ask Paul said to me so Lisa are you free this evening to come and join me, maybe a little something more later on. As carefully and politely as I could I said sorry Paul I already have a date and with that Matt was suddenly back beside me and as he put an arm round me Paul said well lets speak soon Lisa, I do hope I see you again soon and with that he went off back across the bar and well out of sight so I could once again concentrate on Matt.

Like a jealous boyfriend Matt asked me who was the guy you were chatting to and as he looked me in the eye I said to him just an old client who recognises me, in fact one of the two guys in here I have had sex with. Taking his seat Matt said to me now I know why you have been so twitchy since we got here and I understand if you want to leave.

Of course I didn't want to ruin Matt's night but I didn't want to stay much longer especially with people who knew I was secretly a transvestite all be it a convincing one. Carefully I said to Matt I do want to go but I don't want to go alone and with that Matt lent over to me and kissed me gently before breaking away and saying I had no plans of letting you leave alone.

Soon we had finished up our drinks and I knew exactly where I wanted to go and as I suggested it to Matt he had no problem with it so heading back up the hill we finally made it to what I would call a proper bar, the Exchange was a full on gay bar with loads of hunky guys and a packed dance floor any night of the week but it was also accepting of the local trans girls and as I walked in I instantly recognised two Tgirls I knew from various nights out.

Dragging Matt to the bar we instantly lined up a couple of shots of aftershock and then ordered a couple of well chilled glasses of white wine and just stood around chatting at the bar, soon one of the other girls I knew made her presence felt as she staggered our way obviously drunk already and hitting on anyone still standing. As she flopped toward the bar and me she instantly clocked Matt and whispered to me take him home and fuck him before I do before screaming abuse at the barman till he came to serve her yet another glass of whatever her poison was.

Being a Tgirl was always difficult as even though I was with Matt there were so many fit men I would of loved more attention from but this was a proper gay bar and most of the guys had no interest in blokes dressed as birds as they put it. Matt however was getting plenty of attention and it was obvious to me he now felt out of his comfort zone so I decided to drag him upstairs where it was quieter so we could chat.

As we found a couch in a quiet corner I soon snuggled up by Matt's side and as I did I felt his hand start to rub at my stocking clad legs and up to my thigh sending shivers through my body and soon I found myself repeating his moves and finding a solid bulge in his trousers. Shifting myself even closer I knew what to do and as Matt lent in and our lips met first softly then more and more passionately I lowered his flies and slid in my fingers and wrapped them round his veiny thick cock and began to massage him slowly as my hand slid back and forth up and down his thick length.

As our tongues met and I could feel his breath deep in my mouth and his throbbing cock in my hand I knew I wanted his cock deep inside me and soon, all of a sudden Matt almost froze and as I felt his cock pulse hard in my hand he fired his first shot of spunk all over my fingers and his briefs. Instantly he apologized saying I didn't mean to do that you are just so fucking hot, you really got me going.

Chuckling I pulled my hand from his now dripping flaccid cock and licked my fingers clean while he sat looking shocked at my actions, as I finished I said you didn't realise just how dirty I can be did you. Matt just sat looking slightly uncomfortable which made me think I had gone too far but as I asked him if he was alright he said im fine but my briefs are full of spunk.

Getting to my feet I walked to the bar and got chatting to the barman who I knew from visits I had here before and asked his permission to pop out back, looking past me to Matt who was still sat in the corner he said go for it babe blow him good. Tottering back on my stiletto heels I dragged Matt to his feet and led him off through a door marked staff only and up a flight of stairs to a maze of run down rooms where the landlord used to live before the place had become past repair.

Dragging Matt down the dimly lit corridor I knew exactly where I was going and as we reached the end I swung open a green painted door with a hole kicked in it and dragged him inside, as I crossed the room I pointed Matt to a sink in the corner of the room and said that's for after. Looking confused Matt stood in front of me and as he went to wrap his hands round my waist I lowered myself to my knees on the old floor boards and undid his belt then flies and lowered his trousers.

As soon as I had his smart trousers round his ankles I said now you take them off followed by your briefs, Matt wasted no time in pulling off his trousers and as he dropped his briefs I got the first look at his cock and to be honest I felt slightly disappointed at what I saw. For such a gorgeous muscular guy he had barely 6 inches but as I took his bell end in hand and slowly started to massage his cock again he started to stiffen but not grow at least not in length.

Soon I had a nice thick exceptionally veiny cock staring me in the face and without hesitation I flicked my experienced tongue across his piss slit tasting the remains of his spunk from his bell end then as he moaned a little with my tongue wrapping round his bell end I slowly started to suck deeper and longer while I fondled his shaved balls.

Soon I began to build some speed up but managed to take all of his cock deep into my mouth as I blew him hard and long enjoying the taste of his spunk and pre cum dribbling into my mouth as he got more and more excited, I had no idea what Matt had done before and who he had done it with but soon he told me please stop Lisa I need to fuck you babe. Taking one last long bob of my wet horny mouth Matt throbbed hard and as he did he filled my mouth with a second hot load of thick creamy spunk that I swallowed as much as I could as he followed up with another thick shot into the back of my throat.

As he cock fell flaccid again I stood and licked my lips clean before he pulled me against him and kissed me hard and deep as I shared the last of his spunk with him letting him taste his own slightly salty spunk. As he broke away from me to go and clean himself up at the sink I called after him I wasn't going to let you fuck me here, its disgusting up here but I knew you needed some attention just to help you relax.

As Matt pulled back on his trousers he left his spunky briefs in the sink like a present for some perverted punter into crusty spunky pants, and with that we headed back downstairs and ordered another aftershock followed by a large glass of white wine and returned to the couch we were sat on before.

Now I had sampled what he had for me I wasn't really fussy whether he fucked me or not as normally I preferred a bigger cock in me purely for my pleasure but I knew Matt wanted to fuck me and I decided I wouldn't let him down. Finally we got chatting properly and I found out Matt was bisexual and had always fancied fucking a passable Tgirl but after a few rough girls and playing with other guys he had given up on finding someone till the night I first slid onto the backseat of his taxi.

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