~ Saskia's Transvestite Affectations~: May 2018

I almost subconsciously started
to play for a (possible)audience

The man across the street....

As long as I can remember people had remarked how with my pretty face, slight build and general demeanor I should have been a girl. After my parents had died in a car accident, I now lived with my glamorous young aunt Charlotte who was a business woman who owned a chain of upscale fashion boutiques. Now, being a hormonal 16 year old adolescent, I was fascinated by her totally glamorous and sexualized way of dressing. Always wearing the highest of heels possible, tight satin dresses, always perfectly made up and with fabulous hair, she was a teenager's wet dream personified. I kinda idolized her. In hindsight I should say that my sentiment was somewhere between lust and 'wanting to be like her' but I didn't quite realize that untill much later.

Which brings me to my one small vice. You see, after being told how much I looked like a girl so often, one day I decided to see for myself. So after my aunt went out one evening, I snuck into her room to try on some of my beautifull aunty's gorgeous clothes. I was instantly overwhelmed by the sensuous feel of silk, satin, nylon, and lace caressing my body. But the biggest surprise came when I looked at myself. I wasn't stunning, but I did look like a girl, probably even a rather pretty one. So, after that revelation I got hooked on the concept and started dressing up whenever I could, every time getting a bit better at looking and acting like a real young miss.

Sometimes I'd dress all out in one of aunty's formal gowns, do my hair and make-up, and eventually make myself cum in my pretty panties as I pretended to wait for my masculine boyfriend to take me to the dance.

But how can I explain all the sensations that brought me to where I now was?

Once I get dressed I have to be sure I act as a lady completely, only feminine movements , actions and (even)motivations were allowed. I'm acutely conscious of my false lashes every time I blink or flutter and I am absolutely shure I always have to walk elegantly in the highest heels possible. There is this authorative inner voice that makes me take all this as far as I possibly can. The voice that seems to find an almost sadistic pleasure in destroying all that is left of the boy in me. It's also the delightful silky feel of the clothes, the feminine fabrics, and how they feel when I walk and move and how they slip and slide against each other under my dresses. And how the garter straps pull the stocking tops tight, and how tight the girdle is and how they smooth me into a feminine shape. And how the nylons shine and how slippery and silky they feel on my smooth legs and how you can hear that zipping sound with each step as my calves and thighs rub together. These feelings I can only try to explain to someone who hasn't experienced such sensations him/herself.

My body totally smooth now, shaved from just below my perfectly shaped eyebrows to the tips of my gloss red pedicured toes. Everything I now wore was made of nylon, silks, satin and taffeta. I wore in a tight six strap garter belt that held fully fashioned nylon stockings tight and taut high on my smooth hairless thighs, the tight sheer fabric caressing my legs with each mincing step . The sensation of being deprived of wearing even a single stitch of masculine clothing by my own free will was mesmerizing.

So meanwhile I had continued to indulge myself in my increasingly elaborate and detailed dress-up sessions at home. As aunty often left the place to me when she was away on business for a few days, I had all the opportunity to so. Over past few months I had bought quite a few items of ladies apparel of my own and had aquaired a few beautiful wigs. And so in the evenings, when I had the place to myself, I'd get dressed up in one of aunty's prettiest party-dresses, of course complete with fabulous make-up, hair and all the trimmings, fantasizing about me as my beautifull aunt's very glamorous young niece having a quiet night in, lounging around savouring the very erotic sensations of the sensual materials enveloping my body and more and more often there were thoughts mixed in about being lusted after by and being forced to make out passionately with masculine older men. I'm not shure where that idea had come from (probably my'evil' inner voice again) but for some reason the thought excited me to no end.

The whole idea of being seen and lusted after as a pretty girl seemed to amplify all the sensations of this already disturbing game. And then one night when I was once again dressed up to the nines, I noticed that in the house across the street there was someone standing in the window looking out. I wondered if he, as it obviously looked like a man, could see me from there? The thought grew on me and from that moment I almost subconsciently started to play for a (possible)audience.

The whole idea of being seen and lusted after
as a pretty girl seemed to amplify all the
sensations of this already disturbing game.

I positioned myself so the onlooker would have best possible view when I let my skirt accidentally ride up and mercilessly taunted the viewer with the coquettish poses and mannerisms I had been practicing in front of the mirror. I had of course put on my make-up more extreme than any decent young miss would ever have worn in public. My perfectly applied eye-liner and false lashes made me look very seductive and glamorous and my lipstick was so glossy it was almost obscene. My earrings were outrageous too, in shimmering silver and rhinestones that flashed and sparkeled with the least movement of my head and my platinumblonde hair. A very classy wig, of course. I felt deliciously wicked and wanton, a true teenage vamp, and it excited me deeply. The house across the street belonged to old mr.Blenkinsop who was the retired librarian of the local highschool of whom it was rumoured that he was a bit of a Don Juan. And although I knew that there was no way someone would clock me as anything but a very pretty girl once dressed up, he may of course still make the link with the fair boy across the street who lived with his glamorous aunt. For some reason that didn't alarm me a bit so when my 'admirer' once again appeared in view the next night, I just continued my little 'show' for him. I was dressed in the beautifull designer cocktailgown I had bought online a few weeks ago. It was in a gorgeous peach satin and the flaring petticoated skirt was about kneelength. It was the first dress I'd ever owned myself. He must have stood there for at least ten minutes before he moved away from the window. I now saw the light behind his front door come on and I suddenly remembered that it must be around 10.30 ,the time when mr.Blenkinsop usually walks his dog. I was right because there, in the doorway, was mr.Blenkinsop with his prize poodle. Still looking in my direction obviously. It's not that he goes for long walks, it's usually to the end of the street on his side and than back on our side of the street. This does mean that in a few minutes he would be passing our place up close and in my little depraved mind I found myself looking forward to the opportunities that created. Would I really dare to? And how far would I let this take me? As I moved up to look out on the street the man was just across the street and looked straight at me before his doggie urged him on his way. I had almost blown him a kiss there and then but that was probably a bit more forward than I dared to be at that moment. Instead I then poured myself glass of whine and nervously waited for my'beau' to return from his walk, elegantly moving around the room to the soft tones of 'The Love Unlimited Orchestra'. By now in such a state of anticipation and sexual excitement that it actually caused my tightly tucked away boy-genitals to slowly ooze fluids that made me wet my pretty silky panties in an almost girly manner. Of course I kept an eye on the street to see if was coming and when he appeared infront of the house next door I positioned myself close to the window in a way that looked completely natural and as if I was only casually interested in the whole thing. It's one of those ladylike mannerisms one pics up when studying to become a teen-vamp. The mischievous smile on my face would be saying something different though. Even when he was still in front of the neighbour's house I noticed he was furtively looking my way(probably without much success at that angle). I was standing next to a curtain from where I could give him a perfect almost close-up view of his ídol'. So when he appeared and looked straight at me, I was gently rockin' from side to side, gyrating my delicate body to the sound of Barry and his orchestra, casually adjusting a strand of hair and taking a ladylike sip of my drink. My naughty expression was there, I knew that, but I still didn't look him straight in the face untill he gave the impression he was moving onward. Thinking I had lost the moment I smiled my sexiest gurly smile at the already departing gentleman and when he looked over his shoulder one more time before returning home, I actually blew him a kiss. And although he looked back at our place once more, I saw him and the dog go inside and the doorlight went out. I was a bit disappointed but also relieved as I also had no idea how to react as the older man had actually pursued this fantasy..I shivered, and then the doorlight went on again and out stepped my admirer, this time without dog and wearing a jacket and tie. And when he starting to walk over towards our house I almost panicked and I wanted to hide. What the hell did I think? At that point my devious inner voice took over once again so when I heard the doorbel ring, it was like I was in a trance of some sort and I calmly went to answer it . Although almost frightened to death by my own courage, my wicked inner voice actually made me open the front door and there in the doorway was our neighbour, mr. Blenkinsop! He unashamedly stared at me and I stared back, petrified actually. I couldn't speak, I didn't quite know what to say.

I was still completely out of it when he smiled and asked "Well hello there. And who do we have here? What do you call yourself , young lady?"

"Delicia" I stammered. "That's a very pretty name for a very sexy girl, honey " He said with a wicked smile on his face.

He then stepped forward and put his hands on my waist, holding me rather firmly while he was breathing heavily. I knew something was going to happen that was beyond my control. He pushed me back against the wall leaning his body against mine. His vainy wrinkly hands holding me were strong, and his manly strength was strangely exciting to me.

"Oh Mr Blenkinsop!" I mumbled innocently, almost as if in horror, but to him it must have sounded like a sign of arousal as he pressed himself even closer against me. I was almost trembling with both fear and anticipation, and yet I really didn't want to fight it. I was still highly excited and his masculine body against my slim almost girly frame just felt so right, despite my feigned horror. It was really just what I had always wanted to feel, a real man's body against me, his strength virtually overpowering me. I was completely torn, part of me dying to see my fantasies realised, and part of me shocked and almost ashamed that I would ever let something like this happen to me for real.

And I saw the hungry gleam in his eyes when he pushed his quite obviously rigid manhood against me. The thought that I was able to turn a mature manly man like him on so much gave me an intense thrill that melted my last doubts completely, and when his lips came down on mine , I eagerly opened my mouth to let his thick muscular tongue slip in.

Amazingly, my fantasy was actually happening and it was every bit as exciting as I'd imagined it would be. Mr. Blenkinsop was so very much older and the fact that he was almost old enough to be my grandfather was making this all so deliciously wrong. After passionately making out in the doorway for what felt like ages, I nervously invited him in. I couldn't think straight and my heart was pounding . I dizzily led him into the livingroom where he sat down on the sofa whilst I poured him a drink before I sat myself down very close beside him. And when I turned towards him, mr. Blenkinsop caught me once again in a deep and passionate kiss, driving all rational thought from my mind. The helpless feeling of the situation flooded me with wild desire to be taken, and I moaned shamelessly as his tongue explored my mouth. His hands were everywhere but when he then caressed my smooth stockinged legs under my skirt and petticoats, I felt like I was losing my virginity there and then. The ones out there who have experienced it, know what a deliciously intimate sensation that is....

Of course the night didn't quite end there but a 'lady'has to keep some things to herself as I'm trying to keep away from the realms of pornography. Needless to say that my 'boyfriend' went home with a big smile on his face later that night....

It thrilled me to no end to think that I could inspire such passion in a mature man. I'm totally convinced he never saw a schoolboy in a pretty dress when he looked at me. He saw a young and very desirable teenage seductress, even when he knew about my little deception. In the end ladies like us tend to dicover that the men who are willing to go with a great illusion over a mediocre reality may outnumber the others. I've been there.