After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the minute I got home from work every single day; a mini dress, heels and stockings were what I craved so desperately. I had been living alone now for a couple of years and would have thought he urge would have sated by now but I still hungered to be feminine at every moment.
I am five foot six, small round face with short blond hair and blue eyes, size 12 for clothes and with size 6 feet, so pass generally quite well but am not as perfect as some of the gorgeous transexuals I have seen in some clubs.I have had numerous face and body hair removal laser sessions which have helped enormously. I just adore dressing up and it brings me such great pleasure to do so; I buy clothes and shoes impulsively. I must have over a hundred pairs of high heels and as many pairs of stockings and also so many dresses and items of underwear, I have lost count. I also enjoy another pleasure that comes with being a skinny,attractive, smooth transvestite..... sex with men.
A few months ago, on a Friday night, I was in a well known gay bar in Chelmsford, Essex, UK. I had a call from a friend earlier in the day inviting me along to a mutual aquaintance's birthday drinks, so not to miss an opportunity to glam up and go out, I sliped into a little black dress and went along. Whilst I was at the bar getting a drink, I started chatting to a fit looking older guy at the bar. He seemed quite nice, was attractive, about six foot tall with grey-ish hair and the most piercing blue eyes. He was about fifty five years old I guess. He was asking what I was doing there and did I go there often etc etc. His best friend was getting married for the third time and they were on his stag night, trawling the local bars. Then he started asking me about work and was very interested in my current job and any IT experience, he ended up inviting me to interview for a part time role for his business supplying plastic moulded parts for the car industry.
I explained that I already had a full time job but a few evenings or a few weekends would be usefull to earn some extra money, the job would basically mean updating his web sites for him. Besides a bit of extra cash, going to work dressed would be really exciting! We swapped numbers and cheekily I gave him my Flickr page address, for him to see some pics of me. He smiled and said he would love too, we carried on chatting for a while and then he left with his friends.
The next morning about nine am, I got a call from him. Somewhat hung over from the night before and it being rather early, I said that I did remember him and was very interested if the job was still available. I explained that I would love the opportunity to work dressed and he was really positive, telling me that he thought I was beautiful and having me work there would brighten up the place! He invited me to come along to his office on Wednesday midday to introduce me to the other staff and show me around and then a bite to eat to discuss further.
I couldn't beleive it really, the thought of going to a job interview dressed excited me so much and it was something that I had never done before, let alone going to work dressed as that would be fabulous, so not to miss the opportunity I took the week off work, as I was owed some time and went along on Wednesday for an interview. I agonised for ages over what to wear, spent the whole morning trying on so many different outfits but finally reached a decision, sexy secretarial look was a must. I wore my dark blue tight fitting suit with a very short skirt, with matching patent dark blue high heels, dark blue suspender belt and bra with sheer tan stockings.
I left my house and jumped in my little car, I was so excited yet nervous and when I arrived I could see him through the glass front of the reception area waiting for me, looking very smart in a suit. I parked in a small car park opposite, got out and delighted in tottering accross the busy road in my suit and heels with my very short skirt just showing a hint of stocking top as I walked. He seemed really happy to see me and was eyeing me up and down as I walked in.
"You look stunning!" he said.
"Thank you," I replied. He showed me round, it was a small business with about ten guys working for him and I felt very self conscious as all the workers stared at me so much, most were scruffy looking guys in the warehouse and they could't take their eyes off me. I could here them giggling and commenting amoungst themselves but I just loved the thrill of tottering along in my heels with them all staring at me. I think that I am turning into a serious exhibitionist!
Anyway, I spent an hour being shown around and then went to lunch with him in a pub just around the corner. I sat next to him and we chatted away for well over an hour, we ate a light lunch and then much to my surprise he offered me job there and then. It was to be two evenings a week and Saturday mornings. I was delighted and for some reason I leant forward to hug him. We hugged and he put his big strong arms around me and I felt so excited, he released me and then put his hand on my knee and began gently stroking it.
I smiled, leaned forward and kissed him gently on the lips. A little shocked at how forward I was, I blushed but he slipped his hand up my thigh and was stroking my stocking top and smiled as he looked deep into my eyes.
"I won't lie to you Tara but I find you very attractive and am delighted you have accepted to come and work for me but I must admit I was desperate to see you again."
He said thoughts of me had been whirling around in his head since he met me and he had been masturbating over my photos on my Flickr page! I leant across and kissed him again passionately and was shaking a little when I said that I too had fantasised over what might happen and was very excited that he had masturbated looking at pics of me. He said that he wanted me and had always fantasied about sex with a transvestite, he had met a few but most were just cocks in frocks whereas he thought that there was something very feminine about me and he was very glad to have finally met a t-girl he wanted to explorer his fantasies with.
"Lets go somewhere quiet for a while," he said.
I was so excited and told him that I had hoped he would say that.
He went to the bar and paid for our meal while I touched up my make up. We left the pub and crossed the road to the adjacent car park and both got into my little Peugeot car.
"Where shall we go', I asked.
'I know a place,' he said.
We drove for about 20 minutes out of Chelmsford to a country park and headed to the rear descreet section of the car park. We got out and he came round to my side of the car and he me pulled me close and we kissed passionately, I was rubbing his swelling cock with my hand through his trousers. His hands were stroking the top of my stockings and slid up the front of my skirt and pulled my panties to one side and was playing with my tiny cock. He then pulled my knickers down and they fell to the floor around my ankles.
I unzipped his trousers and pulled his hot fleshy, hardening cock through the fly hole, sank to my knees and swallowed it whole, slurping the base of it as the tip touched the back of my throat. I trust my mouth down hard on it several times and was wanking myself, high on the taste and manly aroma of his stiff, thick throbbing shaft. I was going to cum too quickly so I stood up to kiss him again. He pulled a condom and sachet of lube from his pocket and slipped the condom over his thick hard cock and he pushed me forward over the bonnet of my car, my arse protruding out in the air. I could feel the cool lube being spread on my hole, then he pushed his stiff cock deep into me,with him grabbing my suspender straps with his hands, pulling them as he thrust into me and I gasped with the thickness of his length. I felt deliciously slutty with my strong, sexy older man taking me as his stocking wearing slut. My cock was so hard, it ached.
He thrust into me numerous times then pulled out. I lifted myself from the bonnet and turned round and kissed him again, out hard cocks touching each other as we pressed ourselves together. We pulled apart and he sank to his knees and took my small, thin cock in his mouth and lovingly and gently sucked and licked the swelled cherry coloured end. I was moaning and breathing heavily and rapidly approaching cumming and then he stood up, pushed me backwards onto the car bonnet. I lifted my legs and he grasped my stocking glad ankles and navy blue stilletto heels up in the air and thrust his stiff, delicious hot cock deep into me again. I could stand no more, grabbed my cock and wanked it as he fucked me and thick spurts of sticky cum exploded out of my cock and sprayed up my tummy over my suspender belt and belly ring.
The sight of me cumming so hard and his cock being thrusting into me, I could tell he was ready and as he gave one huge,deep thrust into me then pulled his cock back out, ripped the condom off and wanked and sprayed hot juicy cum all over my tiny cock, suspender belt and tan lacy stocking tops.
It was the most exciting sex of my life and as we composed ourselves and I put my knickers on, we couldn't take our eyes of each other. I pulled my skirt down over my cum covered body and hugged and kissed him again. We got back into the car and I smoked a cigarette, I straightend my hair and touched up my make up. We chatted for an hour, saying what an amazing experience it was and how he had fantasised for years about it but never fancied any t-girls he had met before but was instantly drawn to me.
I was so flattered and thanked him profusely. I drove back to the car park opposite the pub and dropped him off, he promised to call that evening and was looking forward to me starting on Saturday. He kissed me and we said goodbye and I drove home. He phoned as planned and we chatted for what seemed like hours, he was telling me that he was obsessed with the sexy t-girl secretary experience earlier that day, he was desperate to see me again and ask if I would go to his place tomorrow night. Of course I would, I agreed, and told him that I will really look forward to it.
The next day soon arrived and I began to prepare as requested, a tiny black short skirt suit, very high patent stilletos, seamed black stockings and black lace basque, bright red lip gloss, looking every inch the slutty secretary fantasy for him.I followed the direction he gave me the previous night on the phone and pulled up outside a large detached house.I parked and tottered up to the door and rang the bell. He opened the door and let me in. He commented on how sexy I looked and I hugged him and kissed him on the lips.
He looked so sexy,crisp white shirt with silver cuff links, tight fitting smart black trousers and delicious smelling after shave, my heart fluttered. I was shown into the lounge and I sat on the sofa flashing my stocking tops and smiling a lot, he offered me a drink and brought me over a large brandy, which I sipped as he came and sat down next to me and started stroking my my stockinged legs.
We started kissing passionately and he asked me to undress, I stood up in front of him and unzipped my skift and took off my suit jacket. Standing before him in just my basque, stockings and heels, he asked me to follow him upstairs. We went into his bed room and he pulled me onto the bed with him. Before I knew it, I had his cock in my mouth, I was slurping all over the end of it, smearing it with red lipgloss, he pulled away and stood up, asked me to get on all fours, he then put on a condom and a blob of lube and slid his cock into me and he fucked me really deep and cum hard inside me.
I felt really sexy and I wanked whilst he fucked me , I sprayed cum every where!! He pulled out of me and he collapsed on the bed beside me and cuddled up to me. We laid there for about an hour and then he said he wanted to take me out. I got up, re-applied my make up and straightened my seams and then we went out to the gay bar where we first met. We drank and danced the night away then back to his house and he fucked my mouth and arse again.
I stayed the night at his place and slept in his bed, just in my stockings and suspenders. We woke up early the next morning, we cuddled and played about and he sucked me off for a bit and then wanked my little cock and put one of his thick fingers up my arse, I had a massive orgasm and cum in big hot spurts all over his big strong hands and hairy forearms. He pulled my skinny body towards him and hugged and kissed me passontely on the mouth, we then cuddled up and fell asleep again.
I left mid-day Friday after coffee and toast.
He emailed and phoned me loads of times that day. He was worried that I wouldn't show up for work on Saturday but I reassured him I would. Why wouldn't I? He's a sexy older guy who uses me like his personal stocking wearing slut and I was loving every minute of it!
I went to his office on Saturday morning to do a couple of hours as agreed, he was waiting in reception for me with a bunch of flowers. I went in wearing a shortish charcoal grey shift dress, tight fitting with nearly black sheer stockings and black leather high heels. I thanked him for the flowers and he showed up to the office where I could work. I worked for a couple of hours and he appeared at the office door and said that was enough for one day, time for lunch. We went back to the pub we were in on Wednesday and sat and chatted for ages. He said that he wants me to bring a big bag of lingerie, stockings and high heels and do a modelling show for him. I am not sure who will get a hard on first, me getting over excited modelling for him or him getting turned on watching me model, so will really look forward to that. He certainly has a thing about stockings and suspenders that's for sure but then again, so have I.
He also asked about the lease on my flat. I said that it was due for renewal and he asked me if I wanted to move into his spare room and see how we get on.... I was really shocked to hear him say that but of course, I said, 'yes'!
It's been six months now and I'm not in the spare room any more.
For the first time, I am truly happy and I think..........
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