More captions..... what do you think?
Saturday, 7 August 2010
Toys for a Sissy.
This is just the kind of equipment that every sissy should have tucked away for a fun night in...
Plenty of dildos and plugs of various sizes and a good supply of lube. Small plugs to get started with then bigger ones to use as the night progresses. A vibrating moulded vagina\anus is always handy I find when some release is required. I find them very humiliating to use when being watched on cam.
An enema kit also adds to the spectacle and can double as a good way to aid intoxication. A mixture of wine, water, and ecstasy can bring out the slut in the most chaste of sissies.
The only thing that's required is a dominant Master or Mistress to administer their use in real life.
Plenty of dildos and plugs of various sizes and a good supply of lube. Small plugs to get started with then bigger ones to use as the night progresses. A vibrating moulded vagina\anus is always handy I find when some release is required. I find them very humiliating to use when being watched on cam.
An enema kit also adds to the spectacle and can double as a good way to aid intoxication. A mixture of wine, water, and ecstasy can bring out the slut in the most chaste of sissies.
The only thing that's required is a dominant Master or Mistress to administer their use in real life.
Saturday, 15 May 2010
Naughty line up
These naughty girls have a sissy in their ranks. Can you guess which one she is? I'm told she had a very good time in the clubs after this pic was taken!
Saturday, 16 January 2010
Friday's Fun
Guess who was out fully femmed last night? Yip, you're right, me! I took the opportunity to try on some of my new clothes that I bought in the sales and find an outfit that I was happy with. I'm glad to say I found some great stuff to wear including a beautiful checked blouse. Not too outrageous, but still sparkling with feminity! I wore a pair of my black 10 denier tights, my new 3" strappy stiletto's, PVC trousers, a black roll neck top, a combat style jacket and her corduroy bag. I looked very trendy and fashionable indeed, a good mix of "young lady about town" and "sexy woman"!
I finished the lot off with loads of make up and a bobbed wig of mine. Once it's brushed and set it's not too bad I suppose, but I still want a new one at some point. I left the flat around 8.15 and headed along the road and came out onto the main thoroughfare. From there I went straight up and along. I passed a roundabout and walked along the length of the Main St. I'd a couple of notable incidents, the best one being when I was stopped at a bus stop allegedly waiting for a bus! I'd spotted a couple of young women, early 30's approaching so I took a seat and stretched my legs out balancing my heel on the spiky stiletto. As one of the women passed me she smiled at me and said hello! Wow! I thanked her back but inside I was really excited by her talking to me.
I also asked a older woman on what the time was, and waved at a pair of drunk teenager girls on a bus as it waited at traffic lights. The both of them waved back but were definitely confused as to who I was! I then made my way down the road and home again giving myself plenty of time to have a good wank about my adventures afterwards! I was home by 10 and my poor feet were in agony with those shoes but it was well worth it.
Friday, 1 January 2010
A Day of Delights
Through a TV site I met a local dominant Master early last month and arranged for us to meet prior to a meeting where we would go shopping for women's clothing for me to wear on a day out with him. We met beforehand in a bar and halfway through our talk he took me to the toilets and checked that I was smooth shaven as I had told him and also willing to undertake the tasks that he would set me. He also had me sign a contract agreeing to obey his commands and undertake that I should become more feminine for his enjoyment. On the day, I agreed to wear a light foundation and some eye liner and mascara so that on close inspection I would be clearly evident as a sissy. As well as the make up I was also instructed to wear a silver necklace and a small jewelled stud in each ear. Before he left I had to kiss his hand in public and promise to obey his commands on the day.
We met outside Matalan first thing on a Sunday morning and I headed inside the store whilst he waited outside in his car. I had a shopping list of items he had compiled that I had to collect. This included the highest heeled shoes I could find, a ladies business suit, knee high boots, two full sets of underwear, two pairs of stockings (barely black and nude) and a white blouse. I also picked up some false nails and light pink lipstick on impulse as I made my way round the store. I quickly collected the items avoiding eye contact with the other shoppers as much as I could before I approached the counter to pay for them. The young girl on duty smiled at me as she slowly put each item through the till, piling them all in a neat bundle before putting the lot into two bags. I knew that she knew exactly why these things were being bought as did probably the two women in the queue behind me! I had glanced round and caught them both whispering and glancing towards me. I had been instructed to pay by credit card so that my name was also known to the assistant on duty so I handed that over to her and waited, blushing furiously.
After this mild humiliation I was then driven to a nearby Boots superstore where I had to go in and approach the make up counter to buy a selection of make up for to use on myself. He emphasised that I had to make sure that the salesgirl knew that each item was for my use and just to make sure of that he had me apply my new lipstick and another coat of mascara to my lashes before I went in. I was trembling as I approached the counter knowing full well that I was quite visibly wearing make up and about to ask for advice from a young woman on what products to buy. The woman on duty was very pretty, petite, long blonde hair tied back in a ponytail, mid 20's with perfect make up on. She smiled at me as I approached her.
Launching straight into a story to try in an attempt to try and hide my embarrassment, I told her that I needed a selection of make up products for myself so that I could look as feminine as possible. To her credit she stood there expressionless as I spoke before she led me to the display. She tried out a couple of skin colours on me before telling me which kind of foundation to buy. Face powder, mascara, ruby red lipstick, blusher, eye shadow, a lip liner, eye liner and red nail polish quickly followed this as I began to settle into my role. By the time she had finished I had filled a small basket with her choices so she took me back to the cosmetics counter to pay. Another young pretty assistant had joined her by this time and she also smiled at me listening intently as her colleague jovially asked me to return if I needed further advice. I thanked her as she scanned it and put it into a bag for me. She also reminded me to return if I ever needed any more products, especially in the next couple of weeks as a 2 for 1 offer was about to start in the store. I thanked her again for her help and walked away content with how things had turned out and as I exited the store I looked back and saw the two women watching me leave, no doubt about to have a deep conversation about the young tranny they had just served.
Master had me tell him exactly what had happened in the store and I felt my clitty stiffen with excitement as I told him the details. We then drove to his flat where I was told to go get showered, dressed, and apply my make up and wig before we left for our outing. As I did this he took a few snaps of me with his camera - for his collection he told me. I was photographed coming out of his shower, drying myself and whilst dressing. I was very confident in my make up abilities and didn't take too long with my transformation so we were soon off on our travels.
We drove to a nearby park where I had to hold Master's hand as we walked around the grounds. I found this simple act really brought out the submissive in me. Holding his hand emphasised the fact that I was his exclusive property. It was just after midday and the park was filling up with people out for an afternoon stroll making me feel slightly nervous with the whole experience but at the same time making me very excited with my new role. I felt so feminine with my new boots, stockings and skirt on and could feel myself stiffen slightly as we walked about.I told my Master how I was feeling and he smiled at me. He then looked around to make sure that no one was looking then told me to sit on a bench, spread my legs and hike my skirt up. I quickly did this before anyone disturbed me in the process. I sat myself down and quickly pulled up my skirt exposing my stocking tops and he took a picture before instructing me to take my stiff clit out as well! I immediately complied and he took some pics of me with my hard clit in my hands.
We walked around a bit more, hand in hand before I was told to visit the ladies toilets and bring myself off into my hand and take it back for him to see. He waited outside for me while I did this - the state I was in it never took too long - then he told me to lick my mess up before we left and went back to his. His eyes lit up as I lapped up my girly pool from my palm! On our return I was bent over his couch and severely spanked both by hand and paddle for becoming too excited on our outing before having a butt plug inserted inside me. I had to spend the rest of the day plugged. He had me clean and hoover his flat while he sat watching tranny porn on his telly. Occasionally he would call me over and have me suck his cock for a while but stop me before he actually came. He enjoyed me telling him my feelings about my shopping trip and outdoor excursion as I worked. I told him how excited being humiliated in front of those women had made me especially because they knew that I was a TV. Master told me that that was good. He then bent me over gave me another severe hand spanking before I had to attend to him making sure that he finally spent his load into my mouth and swallowed every drop he gave me. I was then told to tidy up my make up and clothing. Next, I was told what he wanted for his tea and had to cook this for him. He drove me home a couple of hours afterwards still completely feminised in my new outfit and dropped me off at the end of my road to walk the rest of the way in my sexy suit and heels.
Before he left me though he told me that the next time we meet he is going to drop me off at the harbour area in town where I can stand and wait for him coming back for me! I know exactly what this area is used for and am very excited of the thought of being left there amongst local prostitutes with punters frequently driving by. I know that I look feminine and should not worry unduly but I'm still apprehensive about going down there. He has also told me that I shall be returning to my friendly make up assistant to stock up on some more items before our next excursion. He wants to see how I cope with meeting her when I'm totally feminised and has told me that he wants me in high heels and a skirt for my next meeting with her! He wants to see how good her reaction will be this time when confronted with me dressed in more feminine clothing. I'm both eager to please my Master but scared of the reception I might receive from the assistant if I do go in like that! I do trust this Master and don't think that we'll be visiting these places at busy times of the day. At least not at this early stage of our relationship anyway!
We met outside Matalan first thing on a Sunday morning and I headed inside the store whilst he waited outside in his car. I had a shopping list of items he had compiled that I had to collect. This included the highest heeled shoes I could find, a ladies business suit, knee high boots, two full sets of underwear, two pairs of stockings (barely black and nude) and a white blouse. I also picked up some false nails and light pink lipstick on impulse as I made my way round the store. I quickly collected the items avoiding eye contact with the other shoppers as much as I could before I approached the counter to pay for them. The young girl on duty smiled at me as she slowly put each item through the till, piling them all in a neat bundle before putting the lot into two bags. I knew that she knew exactly why these things were being bought as did probably the two women in the queue behind me! I had glanced round and caught them both whispering and glancing towards me. I had been instructed to pay by credit card so that my name was also known to the assistant on duty so I handed that over to her and waited, blushing furiously.
After this mild humiliation I was then driven to a nearby Boots superstore where I had to go in and approach the make up counter to buy a selection of make up for to use on myself. He emphasised that I had to make sure that the salesgirl knew that each item was for my use and just to make sure of that he had me apply my new lipstick and another coat of mascara to my lashes before I went in. I was trembling as I approached the counter knowing full well that I was quite visibly wearing make up and about to ask for advice from a young woman on what products to buy. The woman on duty was very pretty, petite, long blonde hair tied back in a ponytail, mid 20's with perfect make up on. She smiled at me as I approached her.
Launching straight into a story to try in an attempt to try and hide my embarrassment, I told her that I needed a selection of make up products for myself so that I could look as feminine as possible. To her credit she stood there expressionless as I spoke before she led me to the display. She tried out a couple of skin colours on me before telling me which kind of foundation to buy. Face powder, mascara, ruby red lipstick, blusher, eye shadow, a lip liner, eye liner and red nail polish quickly followed this as I began to settle into my role. By the time she had finished I had filled a small basket with her choices so she took me back to the cosmetics counter to pay. Another young pretty assistant had joined her by this time and she also smiled at me listening intently as her colleague jovially asked me to return if I needed further advice. I thanked her as she scanned it and put it into a bag for me. She also reminded me to return if I ever needed any more products, especially in the next couple of weeks as a 2 for 1 offer was about to start in the store. I thanked her again for her help and walked away content with how things had turned out and as I exited the store I looked back and saw the two women watching me leave, no doubt about to have a deep conversation about the young tranny they had just served.
Master had me tell him exactly what had happened in the store and I felt my clitty stiffen with excitement as I told him the details. We then drove to his flat where I was told to go get showered, dressed, and apply my make up and wig before we left for our outing. As I did this he took a few snaps of me with his camera - for his collection he told me. I was photographed coming out of his shower, drying myself and whilst dressing. I was very confident in my make up abilities and didn't take too long with my transformation so we were soon off on our travels.
We drove to a nearby park where I had to hold Master's hand as we walked around the grounds. I found this simple act really brought out the submissive in me. Holding his hand emphasised the fact that I was his exclusive property. It was just after midday and the park was filling up with people out for an afternoon stroll making me feel slightly nervous with the whole experience but at the same time making me very excited with my new role. I felt so feminine with my new boots, stockings and skirt on and could feel myself stiffen slightly as we walked about.I told my Master how I was feeling and he smiled at me. He then looked around to make sure that no one was looking then told me to sit on a bench, spread my legs and hike my skirt up. I quickly did this before anyone disturbed me in the process. I sat myself down and quickly pulled up my skirt exposing my stocking tops and he took a picture before instructing me to take my stiff clit out as well! I immediately complied and he took some pics of me with my hard clit in my hands.
We walked around a bit more, hand in hand before I was told to visit the ladies toilets and bring myself off into my hand and take it back for him to see. He waited outside for me while I did this - the state I was in it never took too long - then he told me to lick my mess up before we left and went back to his. His eyes lit up as I lapped up my girly pool from my palm! On our return I was bent over his couch and severely spanked both by hand and paddle for becoming too excited on our outing before having a butt plug inserted inside me. I had to spend the rest of the day plugged. He had me clean and hoover his flat while he sat watching tranny porn on his telly. Occasionally he would call me over and have me suck his cock for a while but stop me before he actually came. He enjoyed me telling him my feelings about my shopping trip and outdoor excursion as I worked. I told him how excited being humiliated in front of those women had made me especially because they knew that I was a TV. Master told me that that was good. He then bent me over gave me another severe hand spanking before I had to attend to him making sure that he finally spent his load into my mouth and swallowed every drop he gave me. I was then told to tidy up my make up and clothing. Next, I was told what he wanted for his tea and had to cook this for him. He drove me home a couple of hours afterwards still completely feminised in my new outfit and dropped me off at the end of my road to walk the rest of the way in my sexy suit and heels.
Before he left me though he told me that the next time we meet he is going to drop me off at the harbour area in town where I can stand and wait for him coming back for me! I know exactly what this area is used for and am very excited of the thought of being left there amongst local prostitutes with punters frequently driving by. I know that I look feminine and should not worry unduly but I'm still apprehensive about going down there. He has also told me that I shall be returning to my friendly make up assistant to stock up on some more items before our next excursion. He wants to see how I cope with meeting her when I'm totally feminised and has told me that he wants me in high heels and a skirt for my next meeting with her! He wants to see how good her reaction will be this time when confronted with me dressed in more feminine clothing. I'm both eager to please my Master but scared of the reception I might receive from the assistant if I do go in like that! I do trust this Master and don't think that we'll be visiting these places at busy times of the day. At least not at this early stage of our relationship anyway!
Sunday, 27 December 2009
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!
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!
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