Lessons Learned

In the way of a warning: There is no category for 'bisexual' here, so I hope the tags help. Although this piece starts with a cross-dressing sissy/femdom scene, a lot of the later parts of the story is MMM, with the female character only turning up at the very end. It's not *forced* bi either.

*****

The woman next to him at the bar lit a cigarette, a long, thin, brown one, and inhaled deeply, luxuriating in the smoke. Everybody here seemed to be joyfully flouting the smoking ban, including the beautiful, golden-haired, pink-shirted boy behind the bar.

He had arrived this afternoon, jet-lagged and tired and as instructed took a taxi to the Rembrandt Plein, the very center of the most picturesque old Amsterdam, and where so many of the bars and clubs flying the rainbow flag were concentrated. He found this place, called Mix Cafe, easily, on the long quay facing the Amstel, full of cheerfully drinking crowd despite it being a Tuesday and fairly early.

There were people all around him, who by their sheer presence here, in this small, brightly lit and shamelessly kitschy bar overlooking the Amstel, with trashy Euro-pop pouring out of the speakers, declared if not their own sexuality then the fact that they were comfortable with men who fuck men, and women fuck women. He could probably score here, if he wished - there were men already here eyeing him, close to hitting on him - and he shivered involuntarily, imagining being taken straight to the bar's toilets, or maybe to its back room, his cock hardening in the silk panties at the very thought.

Neil suspected that directing him to this relaxed Euro-trash place, as un-scary as they went, unlike many other gay bars and clubs that were dotted around the area, was a test for him. She had not forbidden sex of any kind, but he sensed that it wasn't really on the cards.

He looked nervously at his watch. It was almost 8.30 and this was the time he was supposed to wait until.

His phone pinged on the dot of 8.30. "Walk across the Amstel. You have a room booked in the Amsterdam House hotel. Your own name. More there."

Neil got up from his chair and walked out of the bar. It wasn't a long walk to the bridge. The small hotel occupied one of the old town-houses along the river. The woman at the reception, a tall, curly-haired fifty-something, gave him a big smile as he checked in. Her English was excellent, as so many people's here. Just as he was to turn around and walk up the narrow staircase upstairs, she called out to him.

'Mr Hanson? There is a letter for you also,' she handed him a white envelope. 'The lady who booked the room left it,' she added, with what seemed a mischievous smile.

He climbed up to the second floor, resisting the urge to open the letter immediately, there and then.

He didn't know what was in it - he didn't know what was going to happen the next day, the next hour, the next minute. For the moment, his life was completely out of his control.

This submission, this relinquishing of control, larger - more real - then ever before - was incredibly exciting. His mind, free from taking responsibility, free from having to make choices, was left to wander, to luxuriate in the fantasies and shiver at the fear of what was to come.

His body was both relaxed, floating, and at the same time taut, electrified, more alive than he felt for years, maybe ever: a blank canvas to be written upon, a pile of rubble to be raked through and rebuilt into a structure of her choosing.

He opened the door to his room, a smallish, shabby but a comfortable one, with a double bed and old-fashioned furniture, including a round table and two armchairs.

He placed his case in the wardrobe and sat down in one of the chairs. His hands trembled when he opened the envelope. Inside, a page of paper, covered in large, messy script in purple pen. He raised the page to his face. It smelled, faintly, of the scent he learned to associate with her gifts.

'Good evening, fucktoy,

I hope you arrived safely (obviously you had if you are reading this), after an uneventful journey.

I also hope you behaved yourself in the Mix Cafe. I am sure you did.

Please strip, shower and shave now.

Then put your underwear on. I trust the black silk knickers were already in use, as requested, and that you brought the other items with you.

Put on the cami, the garters and of course the stockings. I am sure by now you know very well how.

Lovely.

I know from the photo you sent me that your butt is smoothly waxed and your nails are ready to get pretty too. You will have a visitor around 9pm. She will help you move on with these.

I suppose you should wear a dressing gown during her visit. If you have not brought one, you will find one hanging on the bathroom door.

More anon.'

He walked out of the shower with soft knees, his mind reeling with the expectation and anxiety. He had no idea who the mysterious visitor was supposed to be, and he certainly didn't bring a dressing gown. The prospect of facing anybody in the clothes she requested him to wear was terrifying - much more so than the waxing and manicure had been - after all, normal men did those things, even if it hinted uncomfortably at mockable metro-sexuality.

This was different.

He couldn't stop now, though. With shaking hands he pulled on the panties, his semi-erect cock encased in black silk with the palest pink ruffles.

He unzipped his bag - mercifully unsearched by the customs or the security - and pulled out the red silk cami and the long, lace topped black fishnet stockings she had sent him. The garters were his own online purchase.

He pulled the cami on, the sumptuous feel of the silk satin sending cascading shivers of excitement all over his body. He run his hands over his hips, extending fingers towards the back , where the edge of the chemise skirted his now cleanly waxed ass. It felt smooth, slick, strange and yet natural.

The black silk panties she had sent him weeks ago, now carefully washed after he had luxuriated in their taste and scent so many times, were covering his ass and holding his semi-erect cock in a tight,

electrifying bind.

He sat in one of the chairs and slowly pulled on the stockings. His legs were unshaven, just as she said hers normally were. The stretchy fabric enveloped them comfortably. He fastened the garters quickly - it was easy now after so much practice and adjusted them so the fabric didn't bunch up.

He got up and walked to the mirror fixed onto the side of the wardrobe.

There was something utterly laughable, pathetic even about the view that confronted him: a cross-dressing guy in ill-fitting female underwear, his obvious cock straining against a thin fabric of silk woman's panties. He would keel over in shame if any of the people he knew in what she referred to as RL, the Real Life, could see him like that.

And yet, however humiliating even the idea of it was, it felt utterly right. With every step he took, with every order fulfilled, with every corner she took him around, the walls surrounding his identity were crumbling further, breaking, falling apart to reveal something else, not entirely different from the Neil that lived in the RL, but a more complete version of him.

It felt sexy, naughty, slutty, wanton, deliciously perverted. It felt dirty and yet incredibly good, so much that his whole skin was wired up, burning, glowing hot with raw desire.

He turned away from the mirror and checked the bathroom for the dressing gown. It was a dark, iridescent purple, heavy silk garment of not-quite specified gender. He could imagine it on a sophisticated Viennese or Parisian woman of a certain age, or on a middle-age sleazy playboy type. He put it on, grateful for the coverage of most of his body, and tied the belt tightly around his waist, placing folds of the material so they concealed his burgeoning erection.

The knock on the door startled him, and it was a few seconds before he felt capable of saying 'Enter,' in a shaky voice.

The woman - or a girl rather - that came in was nothing like what he expected. A short, skinny, bouncy twenty-something with a wide smile of a wide mouth and Pippi-Langstrumpf red pigtails, she was carrying a large case which she placed on the table and then looked at him expectantly.

'Hi,' he stammered, because there was little more he could say.

She smiled. 'I'm Ana,' she said. 'Don't worry. Madame told me everything I need to know,' her accent was hard to place - not Dutch, and not a native speaker's one, possibly Middle European or

Scandinavian. That the 'Madame' came out naturally from her mouth, without mockery or a smirk, suggested maybe French, but the look didn't quite fit. Or maybe it was just the pigtails.

She directed him to the desk chair, and threw a hairdresser-type wrap over his shoulders.

'Stay still while I make you pretty,' she giggled.

He inhaled deeply, his body tensing, his cock twitching under the dressing gown.

'It will be a little like TV make up... only a bit more of it,' she explained while she worked on his face. '...but not as much as for the stage,' she continued.

She started with his eyes. He could feel lines drawn, presumably in Kohl, around them, then eye shadow applied, mascara on his lashes and some unclear manipulation on his eyebrows.

'Very nice. Very new-wave,' she mumbled admiring her own work before she moved to his cheeks, just lightly touched, and then his lips. She took more time here, starting with a pencil, or a brush that outlined his mouth with something.

'This is so it doesn't feather,' she explained, though he didn't quite understand what she meant.

'Now the lip-liner,' she continued, the sharper but still creamy sensation around his lips.

'And now, I believe we need to use Urban Decay, Revolution. I had specific instructions,' the girl said, in the same slightly giggly tone.

Neil shivered. She had sent him the Urban Decay lipstick. He played with it a little, tried to carefully outline his mouth to make it vivid, pliant, pouting, but it never worked quite right. And of course he never wore it in public.

'And a touch of lip venom to finish,' Ana said, dabbing something fragrant and slightly stinging on his lips before stepping back and looking at her work.

She took a mirror out of her bag and placed it in front of his face. The transformation was startling. He looked... he looked good, actually. He still looked like a man in drag, but he also looked edgy,

glamorous, and yes, attractive. His eyes were outlined in dark, thick Kohl, the shimmery eye-shadow and over-the-top mascara adding to the effect. His face was just lightly powdered, much more like camera make-up than anything else. And his mouth was wonderful, with luscious red lips that opened slightly, puffed up with the ''lip venom''.

It was a mouth he wanted to fuck, these were lips he wanted to cover with cum exploding from his now fully erect cock. He groaned, then laughed to hide his arousal and embarrassment.

'Hands now,' the make up girl said, placing a little cushion on the table and pulling out a bottle of dark-red nail polish.

'Dior's Rouge Noir, as per the orders,' explained Ana as she gave each of his nails, manicured only a week ago in a session of gut-wrenching embarrassment despite a matter-of-fact attitude of the aesthetician who did it - a quick file to then proceed to cover them with layers or dark red, almost purple varnish. She did the other hand and then warned him to wait for at least ten minutes to let the varnish dry.

While he sat with his hands extended, she pulled a cloth bag out of her case and from it shook out a wig, a glorious mane of dark brown, honey-highlighted hair which looked incredibly natural. 'Real,' she confirmed briefly and having placed it on his head, adjusted carefully.

The mirror went up again, with a quick 'Ta-da!' from Ana and Neil gasped.

Now it was hardly possible to say whether he was a man or a woman. The jaw, the Adam's apple, the whole outline of his features were male, but the heavy, dark make up of his eyes and the convincingly feminine lips turned him into a creature of undetermined sex, neither a male or a female, maybe something in between, maybe both, a person simply, a being of potential to be either.

'Thank you,' he stammered in response.

She packed her kit back into the case and left, with a little cheerful wave, leaving another envelope on the table next to his freshly varnished nails.

'Thank you,' he repeated.

He waited until the varnish dried, and then cautiously picked the envelope.

"I think you will find that despite her youthful looks and bouncy demeanor, Ana is an excellent make-up artist.

I was quite specific in my instructions. No "sissy prettiness", that would be too easy, too silly, too tawdry. To fucking American, and we are not in Kansas any more. No closet-queen (though you should, of course, wear the scent, as usual). Just you, or is it her? - emerging.

Take the dressing gown off now, Toy. Open the table drawer now, and use what you find there.

Sit in the chair and wait. Don't move unless instructed.

It won't be long."

The drawer contained a wide, velvety scarf and he put it on with trembling hands.

It wasn't long indeed.

The door opened, without knocking. Somebody came into the room, maybe more than one person. He strained his hearing, trying to assess what was happening from the sounds that surrounded him, but it wasn't clear. Whoever it was, was moving quietly.

He heard the door lock turn and then felt steps moving towards him. Somebody stopped just in front of him. He felt he was looked at, assessed, ogled. He felt burning embarrassment, remembering his shameful attire and his cock, almost fully erect and already leaking small drops of pre-cum, staining the silk of the panties he was wearing.

He felt a hand, running along his chest, a finger tracing the line of his sternum, then a nail edge circling each of his nipples. His body tensed up under this touch, electrified. His cock filled up, painfully.

He felt a nail, tracing the curve of his mouth, but at a distance safe enough not to smear the lipstick. He moaned, a soft, involuntary sound escaping his mouth as it fell slightly open.

'Beautiful,' whispered a female voice. It was hard to try to determine her accent, he expected her to be British but now he wasn't sure what the accent was, some kind of Euro-mixture was all he could detect.

Then he smelled her, the combination of scents that her notes and gifts were always redolent of. He could detect the one he was wearing himself, the one she had sent him in one of her packages, the ''Delicious Closet Queen'', oh so appropriate, he always thought. Underneath this was the other one - the scary one that she delighted in but he didn't quite dare to wear in public, instantly recognizable for its striking, metallic accords of blood and milk, almost sickeningly gagging and yet narcotically compelling.

She smelled like sex incarnate.

Neil couldn't believe that he was so tantalizingly close to her, at last. He could reach with his hand and touch her. He could pull off the blindfold and see her. He wanted her so much that it felt like his cock was going to explode without being touched, as if he was a nervous schoolboy faced with his first willing body.

He didn't move, though.

Presently, a rustle of fabric was audible and a sound of something dropping on the floor. Then, hands on his knees: strong, decisive hands which could be small male ones or large female ones; touching, squeezing, then pushing them apart. His cock was rampant and he was desperate to free it from the confines of the panties now, but he sensed that this would only happen if he was allowed to.

She was now between his knees, he guessed she was kneeling as he could feel shoulders and arms touching his legs. Her hands traveled up his stockinged legs, slowly, maddeningly.

'What a dirty, dirty whore you are, fuckboy,' she murmured. His cock twitched, more pre-cum leaking and staining the black silk.

He could feel her breath on his thighs, then on his pulsing erection, her hands above the stocking edges, then sliding down towards his groin. Fingers brushed his balls lightly. He was panting now, burning, unable to even believe that the level of arousal he was experiencing could be withstood without a release.

She pushed his legs wider, then up onto the armrests of the chair. He was spread out, like a whore indeed, exposing herself to a client, but one that does the work as much for money as to satisfy her own ravenous desires.

His butt was sliding down, but this was soon remedied by a small cushion being pushed under his ass.

'I could cuff you, pet. But there is no need for this, is there? You won't move unless you are told to, will you?' she said.

He shook his head in silent confirmation.

'And I could use one of those, oh, cock-cages on you,' she continued reflexively, with a note of distaste in her voice. 'But there is no need for that either. You will cum when I let you, and no sooner,' she stated rather than asked.

He nodded again, not trusting his voice to come out articulate.

Her hands moved closer to his cock again, but didn't touch it. They moved down his groin, around the base of his penis and past his balls, to slide under the material of the panties he was wearing. Her fingers were now probing his ass, slowly, gently, unbearably. His cock was throbbing so intensely that the pre-cum leaking out became a thin, continuous trickle of semen, as if he had already started to climax but without actually exploding.

The longing for orgasm turned into pleasure of its own. He remembered her saying once that it was like that for women, sometimes: the frustrated need for a major release becoming so intense that it turns into a series of continuous micro-orgasms.

For the umpteenth time he wondered, as much as his mind, floating in the fuzzily opalescent space of submissive arousal, was capable of wondering, what it was really like to be a woman, with a wet pussy and delicious curves, with her own fetishes and desires, with her own way of experiencing pleasure.

He felt just then, being so prettily dressed and made up, and so intimately and yet gently touched, and so tantalizingly near to her, that he was closer to this knowledge than ever before. He wasn't just near her, he was becoming her, or somebody very much like her.

He felt one of the hands withdraw, although the other was still caressing his smooth ass, and then there were fingers between his lips, slippery, sticky, salty, and spicy, and delicious. He recognized her taste and smell, he knew it from the lingerie drenched in her pleasure that she had sent him, but the fresh moisture on her fingers, in his mouth, was infinitely more enthralling. He moaned in response and greedily sucked on the fingers.

She withdrew them slowly. There was a gap then, a movement and sound indicating that she was maybe putting gloves on, a click of a cap of a bottle - lube maybe - and then the hand returned to his groin. It felt rougher, cooler, and he realized her fingers were clad in leather and indeed lubed up; slipped into his ass easily, and she was now finger-fucking him with slow strokes.

'Do you like it, Toy? Does it feel good to be fingered like that? I love it myself, those deep-probing, skillful fingers inside my ass... your ass, inside my pussy... your pussy,' she whispered in a low, hoarse, deep-breathing voice.

'Are you hard for me, pretty thing? Are you hot and dripping wet? Can you feel your g-spot about to explode?'

Th fingers went deeper, stretching him, penetrating, curving up, making him almost black out with arousal and pleasure.