A crossdressers first time fantasy
Im not an author in any way but I would like to tell you about my latest crossdressing adventures. I have been crossdressing for many years but maybe only twice in a year when the mood took my fancy and only ever indoors, the feel off nylon on my legs would get me very aroused and looking at my self in the mirror wearing high heels and a very short skirt had my cock pumping and I always had an intense orgasm, but over the last few years it has became more frequent and not confined to indoors and also where as before I never thought about men my curiosity started working overtime, I started to think about touching a guys hard cock, the thought of me being able to turn a guy on while dressed as a slut still drives me crazy, Fuck my cock is throbbing right now and pushing its head out from beneath my skirt with the mere thought of it.
I am by no means a convincing crossdresser but from the waist down I can look like a right sexy tart, so anyway I decided to start going out dressed from the waste down, normally black pantyhose a red thong and a very short flimsy skirt and off course high heels to accentuate my long legs, I would drive to a quiet car park find what I though would be a good spot, near to a path and near woods if possible, I would check out other cars parked around and look for the guy sitting in his car alone ( they are always out there )
Once in position I would slide my boots and joggy bottoms off and put my heels on, depending on where my intended voyeurs car was parked I would either bring my nylon glad knee up above the steering wheel so it would be visible to anyone outside, or I would partially open my door and rest my foot on the ground.
The thrill when my victim gets out his car and casually strolls around the car park pretending to be on his phone and gets him self close enough to have a better look but still being very discreet. Its usually at this point I swing my door open and get out my car very un lady like making sure he gets
up my skirt, by this time my adrenalin is pumping and my cock is trying to escape my thong, I either open the back door of the car or the boot and bend over to rummage around knowing that my mini skirt has rode up at the back and that my ass is on view with my red thong digging into the crack off my ass.
When I feel ive put on a good show I straighten up and turn around to see what effect ive had on my voyeur, obviously the crotch area is the first place I look, fuck to I love to see a hard bulge straining a guys trousers, even better if he already has his cock out and in his hand and stroking it.
Now this is where my first real adventure gets very boring, the most that has ever happened at one of these outings is I let a guy come up to my window and wank till he came while I also wanked but i came after about 15 seconds as I was so aroused and the whole experience was overwhelming, I do wish now I had been braver and reached out and touched his cock and helped him cum. That night I promised my self I wont pass up an opportunity again.
The window cleaner.
I have over the last few years built up quite a collection of female clothing, almost all mini skirts as I only really dress from the waist down, I have a few red thongs as I just love the contrast of red on top of black pantyhose. I buy all my clothes from charity shops and just love looking at and choosing mini skirts and get quite exited after a purchase and cant wait to get home and try them on and parade around the house.
Since Craigslist stopped the personal ads ive not been out and about much as I used to place an ad
requesting voyeurs to spy on me in my car and text back the replies I received and make some kind of arrangement, I would say where I would be and what I wanted from them, im always cautious.
So it had been a while since I had been lusted over and was horny as hell and still hadn’t played with a strangers hard cock yet.
So I had been into town in the morning and purchased some sexy skirts and a few pairs of black pantyhose from Azda, these bloody pantyhose are always getting ripped.
I was wearing a baggy T shirt, black tights a very short red tartan pleated mini skirt, red thong and a pair of red ankle staps 4 inch wedge shoes. I was just going around the house cleaning up and doing mundane everyday chores and feeling very sexy and slutty when I heard the clatter of aluminium ladders coming round the side of my house in to back garden, I froze with fear and panicked and then hobbled out of the kitchen and into the hall, my heart was racing had James my window cleaner seen me !
I suppose you could say James is quite a handsome guy he is around 40 years old, shaved head maybe 6ft tall and quite muscly, I had never thought about him before as anything but my window cleaner but now im thinking could I take the risk and do a little teasing and see if I get a reaction, risky I know but he comes round every two weeks cleans the windows puts a card through the door and collects his money on the following Friday.
Ok I can do this I thought, I walked back into the kitchen the double patio doors with the curtains open eight feet in front of me with only the dining table in-between, I could see the ladders in the centre of the patio doors so obviously James is cleaning the upstairs window first.
I quickly picked up a duster and an aerosol of polish and moved to the other side of the table nearest the patio doors, with my back to the doors I started to polish the table, I heard the creaking
of the ladders and knew any second now he will see me semi bent over the table, too late now fuck it carry on I thought. I just kept polishing the table stretching over it and knowing he must be able to see right up my skirt my ass cheeks peeking out the bottom of my skirt.
I heard his cloth start to soap the window so I started to move around the table still polishing it I had to see his reaction so I sneaked a peak out the corner of my eye, he was wiping away the soapy suds from the glass but seemed to be oblivious to me, Fuck ive messed up here I thought, now ive lost a widow cleaner and the neighbours will probably hear about this, what a disaster.
I turned round and walked out into the hall and up into my bedroom and closed the curtains and just thought I will wait ten minutes till he is gone.
A few minutes later I hear the back door being knocked, fuck he never comes to the door till the Friday and I know he has seen me, whats he going to say to me, I better go face the music and get it over and done with.
I went down stairs im still dressed like a slut and open the back door just a couple of inches and peek round, hi he says ive just cleaned your windows and I seen that you were at home and just wondered if I could use your bathroom. my heart was pounding and I felt my cock growing trying to push out of my thong, off course I said, come in
Its just through here and I walked in front of him through into the hall, I pointed up stairs and told him first on the right.
I went back into the kitchen and waited on him coming back down, what the fuck is going to happen now I was thinking. within a few minutes he walked back into the kitchen and was just looking down at my legs but his hand was at his crotch adjusting a huge bulge, can I do anything else for you while you are here I said and at the same time reached out and felt that bulge, I then
loosened his belt and undid the buttons on his jeans, I had to put my hand inside his jeans to release his huge thick hard cock, my first cock im thinking and what a fucking cock it is, I started to wank him slowly I could feel the pre cum already moistening my palm, am I doing ok hunni I said as I started to jerk him harder and harder, he then reached out and slid his hand up my skirt and very roughly pulled the front of my pantyhose and thong down at the front and started to fondle my cock and gently squeeze my balls, then I don’t know what came over me, this was me touching and jerking a strangers cock for the first time in my life and now I wanted it in my mouth.
I dropped to my knees and started licking his thick pulsating shaft while squeezing and caressing his balls I then opened wide and took his cock into his mouth sucking long as slow and then faster and faster until his body jerked all of a sudden and he pulled his cock out of my mouth, the next thing I know I have hot stick cum all over my face.
He will be over on Friday to collect his window cleaning money.