The Players

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Sparks fly when cross-dresser Keith buys a pretty new dress.
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MsTrina
MsTrina
89 Followers

1.

His one previous marriage failed early, but at least Keith now possessed first-hand knowledge of the fairer sex. In particular, he was familiar with their anatomy, their scents and make-up, what they wore, and of course, their kind and loving disposition.

In short, he knew about women. This was convenient, because most of his waking hours he fantasised that he was one.

Only in private would he indulge in actual dressing up, sitting, or walking like a woman, and most significantly, when easily achieving a sexual climax via self abuse. After which, he would normally revert back to unremarkable everyday men's attire, pursuing everyday men's interests, like sport, and technical stuff.

His female persona was further divided between dominant and submissive. He was not gay, though he respected people of all persuasions and even had long term friends who were gay. Neither did he actively chase female romantic liaisons. He was already spoken for - he loved his own female persona. Weird.

The new dress hung particularly well. The gathered ruffle caressed the neck without being too constricting. The bishop sleeves with ribbed cuffs provided an airy freedom for the arms and the gradual low hem complemented the ensemble with its joyful flounce. A string belt tie round the midriff allowed the material to hug the top of the hips, reassuring the wearer of their feminine lower body shape. Lined, and made from silky floral print polyester, it exuded a luxurious feel for both the wearer and whosoever may have been lucky enough to be fondling the wearer at the time! It had been altogether a very satisfactory purchase.

Keith looked once more into the mirror, reassuring himself of his desirability, especially now adorned in his sumptuous new frock. In heels, with tummy out and swaying his hips, he then strode purposefully back to the party, over to an empty sofa to await the inevitable attention of some keen new admirer.

Except that there were no keen admirers. In fact, there were no admirers, keen or otherwise. Or any other people at all, come to that. None that existed outside the realm of Keith's imagination, anyway. The sofa was his own bed-sitting-room two-seater. However, the other seat did, inevitably, get taken by Keith's new virtual 'amore' - a handsome, though naïve (and imaginary) adult man. Another lover to take to the limit of sexual arousal and beyond? Yes, Karla confidently predicted - Karla being Keith's female alter-ego, in a pretty new floral print polyester dress.

Let's be clear. Keith was male, of course, and heterosexual, his vast picture library of provocatively dressed females was testament to this. However, his track record in terms of sexually fulfilling any woman's dreams and desires was woefully lacking. In the company of the opposite sex, albeit an infrequent happening since his doomed marriage, his natural tendency was to be submissive, and especially so if the person of that particular gender was of a dominant persuasion herself, and perhaps with exciting leanings towards the darker side of erotic power play. Keith's expensive experiences with professional ladies was clear evidence of this.

But right now, Karla was calling the shots. And a handsome, though naïve (and imaginary) adult man was falling for Karla's beguiling charms. Her hand on his thigh, lip-sticked lips that pouted, perfect breasts which pushed out unsupported, and our susceptible latest flame was more than ready to have his shorts pulled down and be over Karla's lap, to sample the pleasure of her crop, paddle or cane on his bare bottom, depending on her deliciously cruel whim. Cut to scene two, where Karla is now lying on her bed, on her back, knees raised and legs apart. Our latest conquest, now in the form of a rolled up duvet, lies atop our demanding sexy dominatrix. A double tissue is folded around a stiffening penis. Some serious frottery begins and Karla orders her lover to show her how much he loves her. And as the humping gets harder, and the legs tighten their grip around the duvet, our besotted lover might utter a silent 'Yes Miss', or 'Of course Mistress' or 'I adore you Goddess'. An intensely exquisite climax of spewing semen quickly fills the tissue, which after a minute or two when Karla has calmed herself, is removed, destined for the waste disposal. Weird? Yes, I know.

Variety is the spice of life, and Karla was well aware of this. On other occasions, the scenario roles might be reversed, with Karla finding herself in a predicament, having fallen foul of lustful male disciplinarians. After a cruel flogging she would be on her back, down to her pretty feminine underwear, satin and lace bra and panties, and fishnet stockings. With wrists tied to bedposts and open legs constricted by a home-made spreader-bar (Keith's carpentry skills were endless), and a tight ball gag, she could only await nervously the testosterone-crazed gang members each to have their wicked way with her - the rolled-up duvet again proving itself to be a fine actor. If it is possible to orgasm while tied and gagged and after you have been beaten with whips and suffered a succession of sex-crazed heavies inserting their hard willies into your vagina, then Karla surely found the way. And more semen-soaked tissues found their way to the bin. Weirder and weirder...

All in all, Keith led a pretty satisfactory do-it-yourself sex life. Over the years he had amassed a large collection of ladies underwear, dresses, skirts, maid's uniforms and even raincoats. Most materials fell somewhere within his fetish range (satin, nylon, leather, PVC, vinyl, etc) and if they did, he would possess them. And let's not forget a luxurious floral print polyester dress with bishop sleeves and a gathered ruffle! In addition, his armoury of tools included restraints, chastisement implements such as whips and floggers, though finding them too unwieldy to apply effectively to himself, and various 'sex aids' including ones that vibrated, ones that were inflatable, and ones intended to be inserted into places where things ordinarily would not be inserted. Given such an excess of artifacts at his disposal, one may be excused for assuming Keith was perfectly satisfied with his sex life. But one would be mistaken for doing so.

It is a truth universally acknowledged, that a single man in possession of a good fortune, must be in want of a wife. So said Jane Austen, who wrote stories, so could conceivably have just made it up. In Keith's case it was certainly not true - the last thing he wanted was a wife, and the last thing any wife would want is a husband with a built-in lover/mistress alter-ego for excess baggage. But it was human interaction that Keith inwardly yearned for, and finding a living being sympathetic towards Keith's cravings was never going to be easy. In such circumstances, it is quite common that an opportunity will arise quite by accident, leading if not exactly down the road to Blissville, Tennessee, but to a new variant lifestyle which turns out just as good, if not better than the existing one. Or worse. Trust me. 'Blues Night' at the snooker club was one such catalyst. "Do you play?" she said.

2.

The R&B band was churning out "I heard it through the grapevine". They were good. Mesmerisingly good. And it was an extended version exploiting the hypnotic underlying repeated rhythm section riff. Keith was stood by the bar, with a beer, alone and deep in a heady mix of thought about his life plans and appreciation of the band. The very eccentric and seriously overweight woman manager of the bar had trespassed into Keith's body space. He was just a casual club member. She was known by allcomers, who ridiculed her size, her dress sense, and her bossy style of management. Hitherto, Keith merely knew her by sight, and her overbearing personality and reputation. "Sorry?" he said, suddenly realising she was actually addressing him rather than one of the usual crowd of badly behaved and rude male customers. "I said do you play," she repeated.

"Oh, er..." Keith muttered, being a little taken back that such a big personality (and not just 'big' physically, but confident and outgoing despite an unpromising appearance) had deigned to converse with him. "Yes, a little," he replied. "Not very good though, struggle to make a twenty break, I'm afraid."

"Not snooker," she said dismissively. "Do you play?" The accent was on the 'play'.

"Oh sorry, er, no. Used to play a bit of guitar, but never really kept it up. The band are very good aren't they?"

The woman sighed. "No. Do you PLAY? You are wearing lipstick."

Being 'outed' can be a big deal, a life game-changer. Keith felt himself reddening in the face - a face he had hurriedly washed before coming to the club. Could there still be traces of Christian Dior on his lips? Karla had certainly been pouting provocatively earlier that day. How should Keith react? Dismiss the suggestion? Invent some explanation, like a sloppy welcome kiss from a lady acquaintance? A blood stain after nicking himself shaving? He was between a rock and a hard place. He wiped his mouth, as if to challenge the accusation. A slight trace, yes. How could the woman have spotted that?

"Mostly came off on your beer glass," she said, matter-of-factly. "Just interested, that's all."

An awkward silence ensued. Keith was unsure how to react. He was genuinely tempted to spill out there and then the entire definition of his lifestyle. But was discretion a safer option? Somehow, he felt a certain empathy for the woman, who herself openly wore pinstripe trousers and a man's waistcoat. The dying strains of Marvin Gaye gave way to some appreciative applause. Keith decided it would be a good time to quietly slip away. He smiled politely at the manageress, then turned towards the exit.

"Keith," she called after him. She would have known his name from his club membership card. She stepped towards him and popped her own card in his top jacket pocket. "I'm having a little soiree Wednesday evening. Why don't you come round for a drink. The address is on the card. About sevenish? You seem a nice quiet boi. Well behaved. Meet some interesting people. Have some fun."

'Dress optional' said the pre-printed invitation card. In itself, that didn't actually define very clearly what one should come wearing. Keith was not comfortable about cross-dressing in public, if that indeed was what was expected of him, even if the taxi driver would be the only public witness. In truth, Keith was not comfortable about anything, and he cursed the fact that he couldn't make a decision. Did he play? What did she mean? A more conventional quandary also nagged him: 'Should I bring a bottle?'

A more practical consideration might have been 'Should I bring a condom?' but he was confused enough already. Eventually he calmed down and determined he would attend, see what it was all about, go home. No drama. Simple. Oh, and take some appropriate attire in case he was expected to present himself as Karla the party animal.

The card also mentioned some link to a fetish-oriented social media group. Our bossy bar manageress was apparently Mistress Xienna, and she had quite some number of followers. The address was a large Victorian-age detached house on the outskirts of town. Dwellings from that era tend to lend themselves well to murder mysteries, ghost stories and devil worship, mainly due to the dark brickwork, tall chimneys, high ceilings and the pointy tops of gables and furniture - and several creaky door-hinges. Wednesday arrived.

3.

"Hello, I'm Keith, I hope I'm not too early." The girl looked him up and down quizzically. She was barely out of her teens, Keith estimated. Certainly attractive, with long blonde hair tied in a tight large bun resting on the back of her neck. She wore a long-sleeved purple satin blouse, buttoned to the neck, with a knee-length pleated skirt and a wide elasticated belt. Black tights adorned long legs, finishing with what looked like six-inch stiletto heels. Wow. "Wait moment," she said, and scurried (if that's ever possible in six inch heels) back somewhere for instructions for what to do next.

"Very strange," Keith thought. Seemed like she was not quite with it. But the young girl soon returned and demanded Keith follow her to the reception room. And down the corridor they strode, Keith fixated by the sight of killer heels transporting the wiggling bundle of energy leading him on. He couldn't perceive any music or party sounds anywhere. They arrived at a spacious lounge. It was not exactly throbbing with chattering guests.

"Ah Keith," our hostess loudly announced. "So glad you could make it. Do come along and meet people. I am Mistress Xienna. Just call me 'Mistress' and we'll get along fine. You must have a nice stage name yourself?"

"Karla," Keith replied without hesitation. There was a moment's silence. "....Mistress," he quickly added, being well aware of protocol in these matters.

"Beautiful," Mistress Xienna replied. "And your meeter and greeter was the lovely Didi. She's a total lezzer, so don't get any ideas. Aren't you sweetie?" she added, raising her tone slightly and looking towards the stiletto-heeled one. With a false smile, Didi feigned a blush, and nodded.

Mistress Xienna herself presented quite a different persona to the droll bar manageress that was her day job. Her attire this particular evening presented an eye-poppingly exciting dominatrix figure, a leopard print low-cut blouse showing off enormous boobs trying desperately to fall out of a tight front-zipped wet-look bustier corset. A short black leather skirt showed off a lot of thigh. An awful lot.

"And this," she triumphally announced, turning to the only player left in the house, "is Quentin, or Quentina as she likes to be known when in special company. Quentina is lovely and friendly and cuddly and sexy, and I just know you two will hit it off. Isn't that right, darling Quentina?"

Quentin was an experienced 'player'. He knew and loved all Mistress Xienna's idiosyncrasies. "Of course, Mistress," he replied. "Perhaps I should show Karla to the dressing room? I see she has come prepared with some specially nice pieces to wear."

"Good idea, sweetie," Mistress agreed. "Why don't you both run along and get thoroughly acquainted?"

Keith and Karla's domestic dreamworld was beginning to seem tame and uninspiring. These were real people, and real things were going to be happening. Keith didn't know exactly what, but he did suspect something was coming along which may cause a sharp shock to his system. "Karla. That's a nice name," said Quentina, as the two partygoers began sorting out their respective outfits.

"Thanks," replied Keith, determined to make friends with his new acquaintance. "Forgive me if I am a bit slow, but this is quite a new experience for me. Didi seems a little strange doesn't she?"

"She is a nice girl," Quentina replied. "And hot. Though, as you say, perhaps not quite the ticket. East European refugee I believe. Mistress took her in some time ago after everyone else disowned her."

The idea that Mistress Xienna was actually a benevolent soul who housed and fed life's homeless misfits was hard to take on board, but heart-warming just the same.

"Don't worry," explained Quentina. "Nothing bad is going to happen. I suspect Mistress has devised a little game for us. I can say right away it probably won't involve any anal play. Personally, I am more than amenable to it and I am comfortable with a butt plug, but that's unlikely to be an issue this evening since we don't know each other yet. My guess is that Mistress will want the two of us to be intimate in other ways. Are you ok with kissing, and some oral, say?"

"I, er... of course," Keith agreed. By now, he was in a decisive state of mind where he would probably agree to anything.

"And genital contact," Quentina continued. "Mutual frotteurism may well be on the agenda. Mistress thinks it is a sweet game for friends to play - she jokingly calls it a jousting match, and I think she may have us lined up for it. She has a whacky sense of fun, don't you think?"

"Yes, indeed. Sounds, er... exciting." Keith, now Karla, was on autopilot..

"The winner, or loser, is decided on some arbitrary whim of Xienna's," Quentina continued. "They get to worship Mistress however she sees fit. The loser gets a good thrashing from our athletic young lesbian friend. Don't worry, I am a total pain slut - a congenital out-and-out masochist, so who is deemed winner and who is deemed loser has probably been decided already. It should result in a pleasant outcome for each of us."

The two new friends had somehow suddenly become bosom buddies. They began dressing, exchanging views on styles, fashion accessories and make-up, as women do. Karla had brought a shopping bag full of options, choosing pretty black satin M&S undies - panties, a padded bra, suspender belt and black stockings, and Karla's favourite shoes - open toe heeled sandals. Her ensemble was topped of course, by a flouncy new floral print polyester dress with bishop sleeves and rib cuffs.

"Lovely," Quentina gushed, genuinely appreciatively. "Such a beautiful free flowing feminine look. For future reference, if I may, I would highly recommend you get a granule-filled falsie bra. They give you that exact weight that makes you feel like a real full breasted woman. Your tits can then swing, and they feel that much more realistic for yourself or the lucky admirer who is groping you. Just a suggestion."

"Thanks for that," Karla responded, realising suddenly just how naff lightweight foam rubber filled cups were, despite them regularly being de rigueur accompaniments during her home-made fantasies.

"And you just have to, I mean have to, have some nice big hoop earrings. Did you bring any? I see you're not pierced. I can lend you some clip-ons. They make such a statement."

"You are so kind," Karla said. "Yes please, I had overlooked earrings altogether."

Quentina immediately affixed the dangly sparklers to Karla's lobes - the two men's faces coming alarmingly close together. Exactly like couples suddenly falling in love in the movies, there was a momentary pause while they looked into each other's eyes. Who moved first was not clear, but the result was that faces came together, and they kissed on the lips, full on - a sweet and tender real life kiss that Keith, for one, had never even remotely imagined could happen during his lifetime of arbitrary sexual taboos.

The excited happy couple, arm in arm, minced confidently back into the drawing room, where Mistress Xienna now sat in a stately high-backed solid oak armchair - the nearest thing you could possibly get to a throne in the great hall of some monarchical palace. Didi, alert and fidgety, occupied a less grand chair to the side of her mistress. "Oh, look!" Mistress cried. "How sweet! Our girlie lovers have finally re-joined us for some fun and games. What have you naughty people been up to in that back room. Hmmm..?"

"Sorry, Goddess," volunteered Quentina. "I was having trouble fixing my make-up. Karla kindly helped me to get it right. Sorry if I caused a delay for everyone."

Karla suspected that his new-found pain-craving sweetheart was simply inventing an excuse to be subjected to a whipping. He wondered therefore, what the enigmatic leather-clad scene director Xienna had in store for Karla herself. Earlier, Quentin had suggested some frottery game. Perhaps this would occur at a later time. Karla certainly hoped so - their brief clinch when they kissed had brought their bodies together, and, though separated by the material of Quentina's skirt and Karla's dress, respective genitalia had rubbed together... and had come alive!

"Being sorry is not enough," Mistress announced. "You know I hate being kept waiting. Didi has been practising, and is anxious to show off her new skills." Then turning to Didi, "Aren't you dear?"

MsTrina
MsTrina
89 Followers
12