Trust Ch. 01

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Is this the ultimate plimsoll fetish sex fantasy?
4k words
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Part 1 of the 13 part series

Updated 10/31/2022
Created 06/07/2009
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Chapter 1 -- Rite of Passage

"I've got to do something about my love life, Pete," I groaned.

He rolled his eyes and grimaced as he set down my pint on the table in front of me. He'd heard it all before, far too many times.

"How long is it since that skinny tight-arse bird of yours went to Australia?" he asked as he sat down opposite me and took a long sip from his own pint. The first of what I knew from long experience would be quite a few more that evening, it being a Friday.

Was it really almost a year since Joanna had exploded the bombshell that as the next stage of her life plan she was heading off to Melbourne? After a year and a half together I had really thought we were on course. It was the first I knew that she had such a thing as a life plan, and that I was no longer included in it. She had made token noises about me visiting her when things had settled down, blah, blah, blah; but I wasn't about to be fooled any more than I already had been.

I had met other girls since then but nothing worthwhile had come out of any of the liaisons. They were all of a type, the type I was bound to meet working as I do in international private equity services: professional, polished, focussed on achieving their personal and career goals -- working towards the next stage of their life plan.

I wanted something different.

Pete seemed to read my mind. "Your trouble is you keep doing the same old same old and meeting the same birds all the time. Forget all the professional crap. You've got to spread your net a bit wider. All you want at the end of the day is big tits and a tight box."

"And her own pub," I added and he laughed with me. I didn't entirely agree with his cogent analysis of my needs -- however nice they were in their own right I wanted a great deal more than just 'big tits and a tight box' -- but I knew he was spot on about me needing to spread my net a bit wider. After another pint with him I left him to fulfil his quota for the evening and headed off to get my bus home.

I sat by a window on the back seat on top deck of the bus and gazed out. It was early spring and the days were beginning to lengthen so there was a still a little light in the sky not yet swallowed up by nightfall. I idly watched the stop-start panorama of the streets as the bus made its intermittent progress between stops through traffic lights and slow lines of traffic. But my mind was elsewhere, searching for the answer to the question that had taken hold of my conscious thought and refused to let go: 'What did I really want in a woman?' I had to find the answer but I didn't know where to begin.

Just as I was beginning to despair at my lack of inspiration, the bus stopped at one of the main stops on the route. A line of bus stands all had long queues lining the pavement edge and throngs of people milling around. Out of all that mass of humanity my vision was suddenly arrested by one figure that stood out magnificently from the surrounding crowd. She was statuesquely tall and slender; Mediterranean-looking with dark skin; handsomely beautiful rather than merely pretty, surveying all around her with an imperious and almost hawk-like expression in her dark eyes. Her long dark hair was piled up on top of her proud head within a brightly patterned headscarf. Large gold hoop earrings swayed with the movements of her head while a diamond stud in her magnificently sculptured roman nose glittered as it reflected the street lighting. She wore a battered leather jacket over an equally well-worn grey roll-neck knitted fisherman's sweater, old black leggings fading to grey, grey knitted socks and, to my great delight, black slip-on plimsolls with smooth rubber toe caps. A knitted bag with a design that suggested it had come from South America completed her ensemble.

I willed for her to get on my bus and miraculously appear on the now empty seat beside me, but she waiting for another bus. I carried on watching her and wished my bus would suddenly break down. I had almost decided to get off when it suddenly started off again an the last person to get on, a large lady with a couple of shopping bags, plonked herself down next to me with a barely audible whispered 'Sorry' and blocked my exit. I continued to watch the girl for as long as I could until she was lost to my view forever.

I couldn't stop thinking about her for the rest of the journey, and thinking how fantastic it would be to have a girlfriend like her. She was nothing like the polished, professional girls I usually met; she must have been a student or perhaps in art or design; a free spirit, independent, determined to be an individual and express her identity in her own way and on her own terms. Her black slip-on plimsolls had somehow seemed to encapsulate and symbolise all of that which was about her. I was excited by that thought. Maybe I was onto something?

I felt much happier when I alighted at my stop. It was dark by now. The lights shining from the pub on the corner were warm and welcoming and I didn't feel like going home just then so I went in for another pint. Having bought one, I carried it in a zig-zag through a scattering of standing customers to an empty corner table, sat down to face the bar, and almost knocked over my glass in delight at what I saw.

In the time it had taken for me to navigate to my table, a gorgeous Chinese or Japanese-looking girl had perched herself on a bar stool and was ordering a drink. She was very smartly dressed and her dark bobbed hair, make-up, very fashionable spectacles and her accessories were all immaculately stylish and obviously expensive. She wore a smart navy blue blazer over a yachting-style blue and white striped sweater, light blue straight-leg jeans ending at a perfect length just above her bare and exquisitely tiny ankles and, most wonderful of all, on her gorgeous feet she wore spotlessly gleaming white Keds lace-up plimsolls that contrasted beautifully with the warm golden honey tone of her bare feet.

I couldn't take my eyes off her she was so lovely. She gave the barman a beautiful beaming smile as he served her with a whisky and soda and I watched admiringly and longingly as her slender fingers with their beautifully manicured and polished nails caressed her glass and her beautiful white-plimsolled feet flexed, arched and turned little circles around her ankles as she sipped her drink, checked her mobile phone and attended to her make-up. I decided to act. Although I had been wearing my suit all day I still looked pretty presentable. I stood up to approach her and ask if she'd like another drink.

But just at that moment a tall, well-built man with polished, public school good looks and dressed in smart casual jacket, rugby shirt, corduroys and brown leather deck shoes appeared at her side. The long, affectionate kiss they shared made their relationship obvious. I felt totally deflated in that instant. Of course a fantastic girl like her would be snapped up straight away. In other circumstances I would certainly have stayed to enjoy the sight of her for as long as possible; but now I just wanted to go home.

As I headed homeward I felt disappointed; but I now knew for certain what I wanted and what I was determined to find: a girl who shared my love of plimsolls, or who at least liked wearing them and was comfortable with, or prepared to accommodate, the idea of a boyfriend with a plimsoll fetish.

I've loved plimsolls ever since I first wore black slip-ons for primary school PE lessons. Something about the appearance, feel and smell of them really does something to my senses when I wear them, especially when I wear them with women's white ankle socks, leggings or tights, or with women's underwear or with ballet clothing or tight-fitting sports gear. And I just can't get enough of beautiful girls wearing plimsolls, they look so pretty, feminine and desirable.

Until now, none of my girlfriends had worn plimsolls or had shown any interest in them. They now personified and belonged to a past that I had repudiated from this moment. Finding a girl who loved plimsolls as much as I do would be the beginning of a new and better chapter of my life.

While I had been on the bus I had been feeling increasingly uncomfortable and constricted in my clothes and wanting to be free of them, especially from the feeling of my crotch being under close confinement within my underpants and trousers. I had been able to ignore the feeling in the pub at first because of my excitement over seeing the lovely girl in plimsolls. Now the feeling intensified as I walked home and by the time I shut the front door of my flat behind me I couldn't wait to get naked.

I stripped off as quickly as I could and dumped my clothes on the sofa before taking a refreshing and reviving shower with water just on the warm side of lukewarm, giving my crotch plenty of attention with a very soapy flannel that soothed and glided over my skin. I towelled myself dry and tidied my clothes -- I also have a bit of a tidiness obsession -- and then I was ready to enjoy what I had been looking forward to.

The weekend was going to be a busy one: a cricket club pre-season social on Saturday evening and cycling out to Windsor with some mates on Sunday; but I had tonight all to myself to enjoy my plimsoll passion.

In my spare bedroom is a collection of women's clothing containing lots of things that look pretty and feminine when I wear them together with my plimsolls or my ballet slippers (ballet and ballet shoes are my other great passion): pretty summer dresses and shorts, sexy short skirts and skimpy tops, skinny straight-leg jeans, leotards and legwarmers, swimwear, tights, leggings, ankle socks and knee socks.

And the neat thing is that they are there quite openly with no need to hide them away. That's because they belong to my twin sister, Bryony, who in terms of overall proportions (although distributed a bit differently) and features is practically a female version of me except that her feet are slightly narrower than mine, which is only a slight problem when I sometimes wear her ballerina satin pointe shoes with the lovely feel of their satin ribbons wrapped and tied tight around my ankles.

She trained as a ballerina and spent two years with an American ballet company before an injury ended her career as a dancer. Being the very clever girl that she is and having a good eye for fashion and design, she soon made a new career with one of the New York fashion houses. She always stays with me on her regular visits to London and it works very nicely for both of us for her to keep some of her stuff here. It's seems a little ironic when I think about it that, given my transvestite tendencies, it was she out of the two of us who turned out to be gay.

She keeps here several pairs of her pointe shoes in various colours -- pink, white, black and red -- because although she no longer dances professionally she still likes to go to ballet classes to keep up her technique and to keep herself fit, now presumably mainly for Laurelle's benefit.

I enjoyed a few minutes deciding what to put on and then got to work. I put on a pair of my sister's black satin briefs, enjoying the feel of them sliding up my legs and over and around my crotch. I added a matching black satin bra, having first filled the cups with a pair of prosthetic breasts such as women who have had mastectomies use. I followed up by pulling on a pair of black stay-up stockings with lacy tops that circled my thighs. I loved the feeling of pulling them on up my legs and settling my feet into them but that was eclipsed by the fabulous feeling of putting on over them a pair of brand new white Keds lace-ups. Putting on new plimsolls for the first time is just the most fantastic feeling ever apart from sex, and I always have several new pairs in their boxes ready for when I need it. The sight of the brilliant white of my Keds contrasting with the deep black of Bryony's stockings sent me into ecstasy for a moment as I flexed and twirled my feet in delight.

I carefully put on one of my wigs: dark hair in a fashionable bob, and then spent a few minutes putting on make-up and painting my nails, which I keep very neat and just slightly longer than normal for a man, and I was done.

Now you could be forgiven for imagining that I looked a right sight at this point; but if you saw me you might think that I didn't look all that bad, quite reasonable in fact. I keep myself fit and trim by working out and doing various sports. I've got long and well proportioned legs that actually look OK in tights. I'm light-framed and agile and carry myself well and I'm not excessively hairy. In fact I remove all my body hair, using the excuse that I'm a competitive swimmer, which is partly true because I used to swim at county level when I was at school.

It's not that I'm into cross-dressing as such, which I know sounds like a ridiculous statement after what I've just been describing; it's all because I love trying to share as much as I am able to in the experience and the feeling and the look of wearing plimsolls -- and ballet shoes -- in the way that girls do. Without my plimsolls and ballet shoes fetishes I would never have had the slightest interest in cross-dressing per se.

I spent half an hour or so taking photos of my self in various sensual and provocative poses that I knew from experience would show my legs and feet to best advantage, and then transferred them to my PC to enjoy watching later. Then feeling slightly floaty with sensual pleasure, I enjoyed a quick evening meal of pasta and a glass or two of Chianti. After a quick tidy up I was onto the Internet for my main purpose of the evening. I had decided that if I was going to spread my net wider, Internet dating agencies would be a good place to start, on the principle that whatever you were looking for there would be somewhere that would cater for it.

A few minutes' surfing brought me to a site that looked as if it might be what I was looking for.

'FindYourFetishFriend.com -- Find The One who shares your passion -- whatever it is.'

For a second or two I was worried that I was just a pathetic, perverted loser to be doing this, but my fears were instantly forgotten as I clicked on the link and saw the first of the 'new members' profiles on the home page. Shelly from Southend-on-Sea was a statuesque beauty with masses of wavy hair falling to her shoulders. She looked fabulous in a tight and very revealing running vest, tiny cut-away shorts showing a generous expanse of very fit thigh and chunky running socks and even chunkier running shoes. From her description of herself it was obvious that running was her passion in more ways than one.

'...If getting hot and sweaty in a tight vest and skimpy shorts is your thing then call me today and we can pound the leather together...'

'Well,' I thought, 'if a fantastic woman like her is advertising herself here what's there for me to worry about?' So I got to work. I'm not a great one for witticisms when it comes to writing so I decided to write about myself in a way that I hoped would come across as straightforward and friendly. After a few moments of editing I came up with,

'Hello, my name's Chas and I would love to make friends with a girl who enjoys life to the full and the fine things in life. I'm artistic and sporty and up for all kinds of adventures. If you're wondering why I'm here it's because I love wearing plimsolls and ballet shoes and I love to see beautiful women wearing them too. So if you are a friendly, fun, ballet-loving, white-plimsolls-and-ankle-socks-kind of girl, I would love to meet you. Please call me on .....'

I completed my profile by uploading a photo of myself wearing plimsolls with casual clothes and chose an option for secure call forwarding, so that any callers would dial a number on the website and then be put through to my real mobile number without them knowing the number. With everything done, I paid for a monthly subscription with automatic renewal and then logged out.

I felt a real sense of achievement: I had worked out what I really wanted in my life and I had done something positive towards fulfilling my desire. After completing the main business of the evening I was now going to bring the day to a satisfying conclusion by pleasuring myself senseless.

I went into my bedroom, took off Bryony's bra and lay back on my bed. I began to run the palm and the fingers of my right hand over and around my bulge, which felt fantastic through the close, smooth satin hug of her briefs. 'I'd love to watch her girlfriend doing this to her,' I thought to myself, and the image in my mind of Bryony and Laurelle entwined on their bed together while both wearing just their panties and feeling each other through them intensified my erection until my genitals felt like they were in a vice. At the same time I flexed and stretched my legs so I could stroke each foot, ankle, calf and thigh with my other white plimsolled foot, which felt equally fabulous through the silky smooth sheerness of Bryony's black stockings.

I enjoyed the blissful feeling of release around my crotch as I slid my sister's panties down my legs and off over my white plimsolls. Then I gasped with deep pleasure at the first feel of my fingers on my stiff, swollen shaft. On the table next to the bed was a jar of virgin olive oil and a small soft haired paint brush. With these I slowly and carefully painted my bulging head and the entire throbbing length of my shaft until it was smooth and glistening in the soft warm light of my bedside lamp. Every touch of the soft bristles on my stretched and hypersensitised skin felt absolutely delicious.

My heavy breath harmonised with the steady pounding beat of my heart as I lifted my legs up and over so that the tips of my plimsolls rested on my pillow on either side of my head. I delighted in breathing deeply in the heady mixed aroma of clean, new canvas and rubber. As I continued to stroke my erection, my swollen head with the wide open eye of my hole now staring directly into my eyes, I painted my anus with olive oil -- giving me another exhilarating feeling -- and then slowly and carefully inserted the tapered and round ended handle of the brush deep into my fundament.

I was groaning in delight now as I stroked my throbbing manhood and contracted the softly pulsating ring of my sphincter on the unyielding firmness of the paintbrush handle buried deep in my fundament. The image of Bryony lying on her back, naked; her long and slender ballerina legs wide apart and her beautiful feet in her snow white plimsolls pointed as if she wore ballet shoes as Laurelle, the black canvas of her Keds almost merging into her skin, with all the grace and power of a black panther pinning its prey to the ground, lay on top her and pleasured her with a strap-on dildo; further intensified the racing of my heartbeat and the pump, pump, pumping of blood through my tight grip on my most sensitive parts.

Then in my fevered imagination appeared Shelley from Southend, glorious in the Amazonian magnificence of her nakedness, straddling me with her statuesque thighs and sculpted knees like crouching lions. The chunky Nike running shoes that had previously shod her powerful feet were now exchanged for the slightly incongruously delicate beauty of dainty soft pink satin ballet slippers. Her hair cascading in great golden clouds around her Herculean shoulders and her fabulous breasts with their spearhead like nipples rose and fell in a rhythm almost like that of great rolling waves advancing and breaking on a wide expanse of glistening sand as she rode my manhood standing up sentinel-straight within the enveloping, roseate glory of her vulva.

On my left side appeared the tall dark beauty of the girl I had seen at the bus stop, now lithe and long-limbed in her nakedness. Her mass of dark hair tumbling to her shoulders and down her back was perfectly matched by her dark bush of pubic hair that spread between her outstretched legs that flexed with swarthy muscular beauty as she rubbed my body with her long and slenderly beautiful feet in her black slip-on plimsolls with their shiny smooth black rubber toe caps.

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