My First Ever Internet Meet

It's been a while since I've posted anything on this blog so I thought I'd finish the year with the story of what sent me on this wild journey of discovery that I've been on for the past decade.

I discovered the internet around ten years ago when a workmate asked me round to see his new PC. Whilst there he fired up his dial up internet connection and then asked me if I wanted to see some crazy stuff. Of course I did. Who wouldn't? Anyway, he types in an address and within minutes he's showing me loads of half clothed females with their tits and bits hanging out. What really got me though was the amount of TV's on display on the same site! He had no interest in them but I certainly did!

Within a few months I had my own PC and had discovered various sites which specialised in my kind of kinky. Geocities and eventually Yahoo Groups provided many hours of entertainment for me. Through one of these sites I noticed a message asking for TV's to attend a party that an admirer was hosting in a hotel room in my area! My heart immediately leaped into my mouth at the thought of this and it was with trembling fingers that I began typing my reply.

The next day he had replied to me and continued our communication through emails and eventually texts. He was intending to have around 3 or 4 TV's meet in a hotel room with him where we could all relax in each others company. I was intoxicated with this idea and agreed to meet him ASAP so I could meet some others who shared my interests. Bear in mind that up to this point the closest I had come to being feminised in front of another male was when I wore a dress in front of a schoolfriend once!

As the day approached he kept in touch with me with all the details. The hotel, the date, the time had all been arranged. All that was required was our presence. However, the day before he emailed me to say the other girls had dropped out. My heart raced. Was he lying? Was he planning to ambush me and rape me with others? Could I go through with it? To tell the truth I had been so excited and horny in the preceding weeks that there was no way I was going to miss it. That says something about my desire to take risks I'm sure?

Come the day I was up nice and early. I showered and completely shaved myself removing every trace of hair from my body. Afterwards, I rubbed fragranced moisturising lotion all over myself and then sprayed myself with Impulse so that I smelled as feminine as possible. I had been shopping a couple of days earlier and had bought new flesh coloured sheer hold up stockings all ready to wear for my new friend. I wanted to feel as sexy as possible when with him and I always find the feel of new stockings a huge turn on. I had loads of nice pretty underwear to choose from as well as a brand new pair of beautiful high heeled shoes to help complement my long shaven legs . I chose my clothing carefully and packed all my make up and wig into my rucksack before heading off. The fact that I also packed condoms and lube
showed that I also had other intentions in mind!

The hotel that had been chosen was relatively close to my flat and I was soon walking up the drive towards the car park. He had told me his type of car and that the room key would be waiting for me on top of his front wheel and he was true to his word. I let myself into his room and began my transformation from male to pretty young female. I wore sheer black panties and matching bra stuffed with water filled balloons which I found gave me the shape and feel of real breasts. My footwear was to be my strapped high heels which I found simply irresistible when I first saw them in the shop. I had also chosen a short tartan skirt and white blouse for this meeting as I wanted to look as young, sexy and appealing as possible to my new found friend. To help achieve this look I also added some knee length white socks. The bottom of my skirt barely covered the tops of my stockings and I just knew this look would be a winner. Once fully dressed I sat in front of the dressing table and completed my transformation by applying my make up - matte foundation, dark eye liner and eye shadow, thick black mascara, light blusher, powder and ruby red lipstick - and favourite dark shoulder length wig along with a new pair of dangly clip on earrings. As a finishing touch I liberally sprayed some Dior perfume over my sexy outfit.

I sat back in the chair with my heart pounding and texted him that I was ready. There was no going back now. He had been having a quiet drink in the hotel bar while I got ready and soon after my text had been sent he was knocking at the door. I put on my best feminine voice and told him to come in. He was around 50, quite tall, grey haired with a big bushy moustache. He was dressed in a dark business suit which gave him an air of some authority I thought. He told me his name was Roy and that he was delighted to finally meet me to which I smiled and muttered something about being pleased that someone had actually turned up. He came over to me and politely offered me a glass of wine from the bottle of white which he had brought back to the room with him.

Soon we were sitting together sipping wine and discussing our past. He worked for a newspaper which sent him all over the country on assignments which allowed him to meet TV's from other areas. I told him that I was new to the scene and he complimented me on my look and my convincing femininity. Within minutes his hand was on my leg as we talked and his long fingers began stroking up and down my long nyloned legs. I found it very hard to concentrate on the conversation when he did that as I could feel my cock growing in my panties. Eventually his hands wandered further and slid underneath my rapidly rising skirt. He announced that maybe we should become better acquainted with each other and I nodded my head at this which led to him leaning forward and kissing me. He then broke off, lifted me up and carried me over to the bed.

We embraced and kissed harder than ever. Our tongues mingled together and my mind raced with all kinds of thoughts. Was I now gay? How far would I go today? Where would this end? Was I really kissing a man with a moustache! His hands soon freed my cock from their pantied prison and he teased me by pushing me back onto the bed and playing with my cock roughly. I sighed and moaned as he used me as his tranny plaything with his hands pulling and peeling me as we kissed passionately on top of the duvet.

After a little while my head was guided down towards his crotch where I was soon unzipping his trousers and fishing around for his stiff cock. It was around 6" long, uncut and not too thick. Inwardly I was pleased with it's size and shape as I wasn't wanting a huge cock ruining my cute virgin hole! I licked it all over and knew exactly what was expected of me so after a small amount of manipulation I clasped my lips around it and began bobbing my head up and down. This small act was another big step for me as I was doing exactly what I knew I should be doing - and wanted to be doing - when I was dressed up. For years I had fantasised about doing just this - wearing my sexiest girly clothing and sucking a man's stiff cock at the same time! I couldn't even guess the amounts of times I'd ran through various scenarios with it happening.

Roy pulled my black panties off then manoeuvred me into a better position where he could suck me at the same time and which also allowed him easy access to my tightly puckered boy pussy. As I worked my head up and down on his swollen cock I could feel one of his fingers gently circling my anus, teasing me as he did so. I was lost in the moment and was pushing and grinding my hips as he continued to toy with me. I could feel his finger slowly enter me and my hole tightly gripped his finger as he worked it deeper inside me. I gasped in delight as he slowly finger fucked me as I lay spread eagled below him with my stiff clitty in his mouth. Little by little he stretched my boypussy and I knew he would soon be mounting me...

"Please.... it's my first time" I whimpered....

"That's okay Fiona. I know just how to treat you" He replied.....

Roy then asked me if I was ready to become a woman? I knew what was coming and broke off from my cock sucking to position myself further up the bed. I lay head down on the bed with my arse raised towards him ready for him to finally take my sissy virginity from me. Roy stripped off, came towards me his cock glistening from my oral assault and pulled a condom onto it. He gripped my hips and began probing at my hole with his cock. I had never been in this position before and was worried that my tightness would put him off. I needn't have worried though. Slowly and gently he eased himself inside me setting my mind at rest before he began his slow gentle rhythm.

In and out he went holding me tightly all the way through his act. He told me how beautiful I looked and that he'd love for me to accompany him on a night out sometime. I lay beneath him moaning and feeling my tight hole stretch as he worked in and out of me. The feeling of his hairy balls banging against me was one that I loved as it was this that made me feel so womanly. My clitty had lost its hardness but Roy occasionally reached between my legs and pulled it to keep me excited. Being filled to the hilt and having his big balls slam against me was absolutely fantastic. I could feel him fill me up then withdraw to the point where he nearly popped out.... before ramming it in again! Roy was getting faster with each thrust and I knew that he was approaching his climax by the frantic sound of his voice. He called me his little slut, his sissy tart, his tranny whore, his fucktoy.... and then gripped me tightly round the waist and exploded deeply inside me....

It was done. I had finally managed to dump my inhibitions and lose my virginity while dressed as a woman. My journey - which had started at the tender age of 7 with me trying on my mother's tights - had taken a new course. No longer was I content to continue on a solitary voyage. Instead I knew that my fantasies had the potential to become reality and that nothing would ever be the same again. Funnily enough, there was no way that I could have known just how twisted and sordid my fantasies would become in the years to come!