A man see me in panties became an obsession

In a first essay I recounted my earliest awakenings of interest in womens' clothes and how that progressed to yearning to expose myself in panties to a man , hoping he would fuck me ;and how that endeavor failed .

You only know me through my words - which if I am to hold your attention will have to arouse you . Which I will try to do . provided there is a bargain between us . Being that my words also bring me arousal – but only by them being expressions of real things that happened . Which forces my writing to be of what I remember - and truth is tricky ; nuanced ; biased – but ultimately recognizable as truth .Your side is simply to accept that what I write was real even if sometimes there was disappointment .

I am unattractive . I am stocky , balding and plain featured . Big drawbacks when your desire is to present yourself as physically desirable to other men .

Not that that stops men totally . Men have to calm their need for an addiction so even an unpassable crossdresser will 'get lucky ' sometimes .

This realisation came to me over time when I took to ' cruising ' in progressively more feminine garb . Men who were only there because their need for orgasm was greater than than their fear of discovery or disease would nonetheless recoil from my blatant presentation of myself as a damsel in heat . Responses to my flirty hiking of my skirt in the bushes were roughly one third unresponsive passes , one third mild disgust , and the rest a mixed collection of engagement . It is the third segment you will want to hear of – and they were a pleasingly teasningly mixture of strangers for whom I have grateful memories .

By late twenties I had moved to Canada , wife and children in tow . Exploring the local area with the kids is how I came upon a 'stroll ' . 

I saw a man loitering on a rail line . He was close enough for his clothing - which was limited to an undergarment - to be studied . They might have been mens underpants , if of an unusual green colour ; or possibly swimming trunks . They were ambiguous and the wearer or a disposed observer could assume them to be suitable for a woman . Seeing us he walked away into an overgrown hollow . It seemed to me that where there was one man in knickers there might be more and when free to explore this possibility my curiosity brought me back .

Readers : many of you may have used or been aware of ' strolls ' ; some may have wanted to use one but dissuaded for various reasons ; and perhaps some unaware of them ( if so you are likely new to the excitements of crossdressing and new to sites such as this ). Allow me to describe the particular one of this story .

The hollow would fit within a soccer pitch . It was cordoned by a highway , a railway and a cemetery with access ( with some difficulty ) from all three . It was an easy walk or cycle ride from the city - and to avoid the possibility of a car being identified I left my bike in the cemetery and climbed the mesh fence to enter the triangle . At which point was steeply sloped with tall trees . Descending into the hollow the vegetation changed to bushes and grass with worn paths .

Although on my first visit I did not absorb the significance of other features , the area between the slope and the railway was at a lower elevation . The railway was the hypotenuse of the triangle and overlooked the bush area – and was a ' runway' for anyone wishing to demonstrate their presence to the triangle . The main worn path roughly followed the perimeter of the triangle . At either end of it's railway section it expanded into room sized recesses overhung by branches .

Multiple smaller shielded recesses were present where small paths diverted from the main one . Flattened grass floored them .

On my first visit the impression was of a considerable population - maybe seven men in total scattered along the paths .Their absence of communicating was notable – they mainly stayed in one spot and if encountering another they would neither speak nor give acknowledgement . There was one exception - an alcoholic had made his summer home in a recess - he joyously told me “ there are more of them ( meaning waiting homosexuals ) over there .”

In the weeks that followed I day dreamed about a visit . But what if I was recognized ? ( a possibilty that later almost occurred when an aquaintance was laying flowers on her mother's grave . And how did contact start , and proceed ?

Almost surely you know the irresistible draw of sexual anticipation and forsee that I made a visit . If like me you read these stories to get aroused you may want me to get on with the good bits . I will , but want to explain that these sexual encounters were usually very short and if the telling of them follows the pattern I find in many descriptions where exchanges seem to precipitate explicit language and heavy emphasis on huge penises and dominated sissies I think I can do better by being more nuanced and giving room for your imaginations to play .

Canadian weather should make cruising seasonal - though ( post coupling ) with a man who unlike most was prepared to talk I asked what ' guys did in winter ?' . He told me ' I've seen guys out here in the snow ' . And they do , but I since have thought cruising in a car likely is the answer ( more on that later ) .

My plunge was in summer where hot humid days make for light clothing . My ride to the cemetery in shorts , a singlet and a baseball cap would not stand out - but that concern was blanket suppressed by the high all round anxiety I was feeling . 

The anxiety was intermittently eased by awareness of the goal of the outing and how the one piece of clothing I was wearing that was not visible to the world would connect to that goal . But at the destination my heart was racing as i descended from the fence and made my way down to the main path . I took off the singlet ( too manly ) and made my shorts – fairly short to begin with - even shorter by infolding the waist so the leg rode higher . I did this more than once and throwing caution to the wind I checked what I couldn't see without a mirror - was the scalloped elastic hem of my underwear now peeping out from under my shorts ? 

Touching it I could feel that it was and that put me in an instant condition of heat that vanished all caution . So ,panting with need I went looking .

As on the scouting visit there were men lurking . Or perhaps not as I did not have to go far and the first man I saw proved the only man I needed ; and after our engagement I fled . Ashamed but with expanded knowledge .

That knowledge being that the stroll did indeed fulfill its promise of delivering an orgasm . And like opiate addiction ( which may share the mechanism of compulsion that is seen in sex ) the experience gained made future visits inevitable .

Rounding a corner of the path the view opened onto the lower margin of the slope where the trees gave way to bushes and where there were some open grassed parts . He was sitting in plain view on the sloping grass . He would be in his fifties , tall almost gangling .

His pants front was undone and as I came upon him he pulled his underpants down sufficiently far to expose himself .

This being a common signal and hardly requiring the addition ( none the less frequently seen) of frotting one's crotch – usually before undoing one's clothing - 'though in his case he now had his underpants below the field .

He languidly stretched himself by the tip . I have a distinct remembrance that it looked long and narrow – but it may well have been a temporary condition as my arrival had been sudden and anticipation had insufficient time to engorge him . ( When cruising I am in a constant ' hot ' condition and used to try to force my erection out of sight , thinking it un-feminine and off-putting to potential partners – which I have since learned is not at all the case ) .

My pre-visit worries on how to approach a man now had no basis ( with experience I have become bolder and very direct ) and without hesitation I sat down by his side .

In a heavy dutch accent he said “ A nice day to be out and about . Can I help you with anything ? “

Even now I am astonished at how I was able to respond - not only was I a complete virgin with respect to intimacy with a man ut this was my first outing ( other than the pavilion episode ) - it confirms that in sexual need there is no action or risk I will not take . 

“ Can I sit on your lap ? “

“ Be my guest “ - accompanied by a wave of the hand above his crotch .

Clambering across him so as to be sitting on him raised difficulties . The steepness of the slope and slipperiness of the grass required him and me to support ourselves which deprived either of us from using our hands - in his case I assume he would have directed himself to be able to penetrate me . In my case I wanted to take off my shorts - still seized with the wish to be seen in my panties .

It would have made sense for him to suggest we relocate to a flatter ( and more private - 'though he might find a thrill , as I do , in third parties watching ) place . But he didn't - possibly because as quivering with lust as me , or possibly not wishing to lose this new catch ( I was young fresh meat compared to the stroll average ) .

So we made do – him handless as he resisted sliding down the slope with me now on his lap . And me one handedly pulling down the waistband of my shorts - for which my exhibitionism had them rolled up ,so I could only disengage one leg at a time - switching supporting hands then eventually able to wriggle and toe them off completely .

Which left me in my long dreamed of state of being in front (– literally – ) of a man whilst wearing womens' panties - black nylon ' high rise ' ones - I would chose different ones if reliving that moment now .

No doubt he could see them on me - if just the portion where they covered the sides of buttock and thigh before disappearing from his view around my front . Also probable is that he would have no interest in them - other than that my wearing them confirmed what he already new- that I was a sissy homosexual who wanted to ' catch ' . And as a youngish specimen I would likely feel good. Certainly his thoughts were in the right direction in that respect – as I could tell from the warm and definitely bigger protrusion I could feel indenting my panties when I lowered myself down on his lap .

I don't think I had thought this through well enough . Being a virgin I did not know that being buggered without preliminary play and lubrication is painful – a cruising sissy needs to carry Kleenex wipes , gel , and be wearing an anal dilator close to the time of penetration . None of which I had - but I was well aware that the warm probe's proper destination was between the cheeks of my bottom then thrusting inside me .- And I would love to have made myself it's home ( sensing a man's desire and submitting are  the major elements of sissy psychology ) but in view of what would likely have been a bad first experience it is as well that I was so close to final release that stroking myself ( through nylon is so nice ! ) I ejaculated frenziedly .

With the selfishness of that relief the flood of shame and worry returned . Instead of doing what a generous partner ought to do – place my face to provide him with a warm wet simulacrum of a vagina - I did what almost all of these stranger on stranger encounters end with – mute separation .

But not before he commented :

“I could have done that for you .”

So , quickly back to retrieve my bike and a sticky ride home , to hand wash the guilty panties .

Since then the stroll – and not just that one – has called me many times .

Some ventures have been treasured , others disappointing . I intend describing them - doing so is a nice sex thing for me – and I hope for you too . Some feedback would also be nice - sexy is good but I'm also interested if my keep-the-explicitness-low style works , or not .