Written by Jennylonger

14 Dec 2011

Well if I knew what I do now would I still have gone ahead? The probability is no I would not, Am I pleased I did? Well maybe I am, after all I do enjoy the liberty it has brought me, and in parts the actual weekend was fun, though parts were to be frank scary.

It is six years ago June just gone, I was living on my own at the time, and getting back into being a transvestite. I have always cross-dressed and from quite young, 14, to be exact, but the tales from then are for a different story. Being a transvestite for me is that extra step of making an effort to be as feminine as possible, not easy when you are six feet tall. Still I try and the result is something sexy if not perfect, smooth legs, good hair and make-up help. Well it makes me feel comfortable about meeting in private at least, though going out to anywhere but clubs of the right type at that point would be a different matter.

So there I was dressing again and looking to meet for sex, which occurred often enough to keep me satisfied, as well as few regular partners who enjoyed having a willing mouth about. Besides just dressing girly, one pleasure is to dress as a maid and be subjected to punishment and humiliation, something you would think easy to achieve. The reality is that it is not, it is a rare man who has the bottle and imagination to take a girl like me and use her in a way that takes her out of herself. Yes you get the spankers, the bondage guys, and the name callers, guys who want to come and use you some who even bring a friend. Each is good in their own way, and it is fun just the same, but a true master type is not easy to come across.

That is where John got my interest, I had been chatting to him on a site at odd times, discussing what I had been up to and bemoaning the lack of effort people put in. In these conversations, at least as far as I recall he never mentioned that he was experienced in having a slave, or even that he met TV,s though the latter was something I guessed he had an interest in. So I was very frank about what I thought I would enjoy, and how I would like my boundaries opened up.

It came therefore as a bit of a surprise when he told me that him and some friends where going up to Yorkshire for a weekend in a cottage they had rented, and that he would like me to come. After a little persuading, well quite a bit actually I said yes, that another TV would be going is what swung it for me. That and the promise of much teasing and humiliation.

They were driving up from oxford so I had plenty of time to pack and be ready for when John and Sarah, the other TV got there. I was waxed smooth and case by the door when they knocked, I opened the door to my first surprise, Sarah was stood there in a pink maids uniform pink stockings and heels, I was living on a terraced road so there was not even the privacy of a drive to obstruct the view of this admittedly very sexy looking, to my eyes at least, vision of pink sissyness from the whole street. My colour must have shown my demeanour and embarrassment, as john said I think Jenny would like us to go in. The second thing that struck me was how close the way Sarah was dressed to the way I looked when I acted the sissy maid, in fact the dress was the same , her black hair was different and her shoes were open toed heels. Do you like asked John smiling, I took note when you where telling me about your purchase and thought it would be fun to have two maids together. It was a turn on the idea of us both being able to tease the guys, our little skirts far to short to be decent, that thought leading me back to how that would look to the neighbours. Still I gave Sarah the once over again and thought it was not so bad she looked very feminine if a little OTT.

It was johns next words that shook me more if that could be possible, “well we had best get you dressed then”. I was ready to go as far as I was concerned; t-shirt and jeans, my frocks, undies, wig and make-up safely packed in a bag. I told him I planned to travel as I was, to which he replied not a chance, if you are coming then you will dress like Sarah. This I was not ready for, humiliation yes but in private. As I said I lived in a row of terraces, it was a pleasant summer evening, not the late and dark that I had occasionally dared to go out under the cover of. I was to say the least in a dilemma, Sarah asked if I had packed my maids uniform, which I confirmed I had. ‘well honey she said lets put you in and take it from there no commitment, if you do not want to come fair enough we can have a bit of fun before we set off’. Yeah said John at least put on a show for me with Sarah, I can film it for the guys to watch.

Well I fell for the trap, Sarah helped me dress and believe me I was keen, she looked hot and I knew with a bit off help with my make-up I would look an image of girly delight too. The dresses we were wearing while being of a maid style wear totally sissified, pink in colour, with ribbons and bows and layers of underskirts. They were also far too short for anything other than wearing in private, which was why I had been shocked to find someone on my door step in one, they screamed come fuck me.

By time I was dressed, hair and make-up done, my modest cock was stiff in the pink lacy panties I wore. I looked in the mirror, to see a vision of girly pink, my long legs in pink stockings finished at the end with pink mary jane heels, that had taken me an age to learn to walk in. My nails were painted pink to match my dress and Sarah bless her, had even got the little pink hand bag for me that matched the dress, but sold for a silly price on the sissy wear site the dress had come from. It was one of those weird occasions when you look in a mirror and do not recognise yourself! I looked like a sissy cum slut, it made me feel weak at the knees, and I wanted to stay like it forever. Sarah came over and said one finishing touch, putting a pink ribbon in my hair.

She kissed me then and stroked her hand against my cock, it made me tremble, are you coming then she asked, I think she knew the answer, even before it came out in a whisper, because she was already taking my hand to lead me out. Well it was not till the hall that reality hit me, no way was I going out that door like this, yet everything in me wanted to. John who had been waiting in the lounge, came through, and the look of wanting me was plain, he said wow and meant it. ‘I think she may be a bit shy’ said Sarah talking about me as if I was not there, which in some ways I was not. ‘Come on hon’ said John, ‘think fancy dress’. I think I just shook my head and said no, but in truth it is a blur. He had got me though, in past conversations on the net I had said to him how one day I planned to go out or dolled up and pretend it was fancy dress. ‘Come on he urged, think it will explain Sarah to, both of you going to some crazy do together.

My mind raced, was it possible, could I pull it off, he opened the front door, Sarah took my hand again, and like some unthinking automaton I took the steps I needed to pass out the front door. John pulled it shut behind us, I heard the latch click, at the precise moment the breeze lifted my little skirt. The dream was broke, the sounds of the outside world came rushing back to me, traffic passing, the sound of a car door slamming shut, and worse still footsteps and voices. You know those dreams where you find yourself naked; this was a real version of that. The chatting stopped, replaced by an oh, if Sarah had not got me by the hand, firmly pulling me to keep moving then blind panic would have set in leaving me no doubt scrabbling undignified looking for a key, that I was not sure I even had.

The thought that came to head was get to the car, if anyone asks deny all knowledge, me in a dress don’t be daft I convinced myself I would say. That walk was a long one, it felt like it took an age, it was certainly longer than it needed to be. They had parked a good distance from my house yet at that time there was plenty of spaces virtually on the door step. The last embarrassment was saved till last, I was just getting to the car, which John not tottering on heels had got to first door open and ready, when a front door opened and bursting out as they are want to do, came a group of teenage lads, there was a chorus of whistles and one cry of do you take it up the shitter. I did not know Sarah, but was shocked when she boldly walked towards one and lent in as if to kiss him. The result was bizarre, while he backed away; his mates chided him as if he had bottled a chance kiss of some sexy girl. Even John got a ‘you’ve got your hands full with those two’ comment, with no hint of sarcasm.

John smiled, lent in and kissed me, we had pulled up at the services, John took my hand and helped me step out. We had talked on the way up and he confessed he had bet they would never get me out the house. I was not sure how I had done it myself but deep down knew I was pleased I had, at least once the shakes had gone, it weird how the body reacts.

Well said john ‘time you met your master for the weekend’, the shocks were not over then! I had assumed John would be having control of me, and had felt quite comfortable with the idea. ‘Don’t worry I have briefed him on your fantasies, I kept a careful note’ he added almost breezily. It dawned on me that I had been groomed for this outing; john had obviously been playing the long game with our little chats. It also dawned on me how depraved some of those fantasies had been, never in a million years thinking they would possibly see the light of day.

We had parked away from the buildings, but it was holiday time and the car park was busy even at that distance. I leaned against the back of the car out of site of people, going about their business, I would have stayed in the car but my bladder was letting me down. My plan was to nip over the service road and pee in some bushes, reality was this would seriously draw attention, and a trial on the verge brought home the problems of heels on soft ground. I was saved by a guy in the next car down; he came round to put something in the boot, his eyes virtually falling out of his head when he saw me. Who couloured up most it is hard to say, but my make up cut down on my glare I should think. His eyes strayed to the bare flesh, where my skirts finished and my stocking tops started, only the line of pink suspender, covering it. The lust in his eyes at that point was beyond anything I had previously encountered, though I realised I must have looked at Sarah that way only a few hours before. Some kind of photo shoot he muttered, I just nodded, he nodded back and went scurrying to get in his car. I realised I had just passed a milestone, here where I was unknown I had passed as a girl, in broad daylight, and a clearly straight guy had desired me. To be continued