Sunday, March 7, 2021

Awakened

Awakened

What do you do when you are awakened from a dream? Awakened suddenly. Awakened to realize you've been betrayed by that dream. Betrayed despite how wonderful that dream was. Was the dream a lie? Was the dream a truth that you actually wanted? If so, what do you do about it all once you've been awakened?

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I had a lot of fun writing this one.  It's relatively brief but it touches on a whole lot of fantasies for me.  For whatever reason the "office setting" is powerfully attractive as it can combine power dynamics of employer and employee as well as a more elegant sorts of attire.  Men in suits and women in dresses - and feminized men in dresses serving those sharply dressed superiors in the office - that all can make for a lot of erotic tension.

Throw in some kinky senior partners in a firm with a "hapless" man at their mercy and it can light a lot erotic fires!

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He heard the door opening and realized he was trapped.

He wasn’t supposed to be where he was.  The Executive Washroom was for, executives.  And William Herrara was many things but an executive with Wilkins, Cortez, Simpson and Dawes wasn’t one of them.  It wasn’t a job ending offense but it wasn’t something the regular employees of the firm were supposed to do.  William did take liberties in sneaking into the washroom because he was the personal assistant to Mrs. Bianca Cortez and because he wanted the privacy of the Executive Washroom to clean himself up and repair what “damage” Mrs. Cortez did to him each Monday morning at 11:00 AM.

That was when he would report to her and she would inspect his outfit for the day.  The outfit wouldn’t ever be a surprise to her as she’d have laid it out for him in the morning before she left for the gym.  He would change out of his nightie, clean himself up, make sure to thoroughly douche himself, dress in the shirt and slacks she’d specified and then scurry himself in to work.  She would then inspect not only his outerwear but also the lingerie she’d also specified for him to wear under that corporate wear shirt and pants.  The inspections always left him frightfully turned on and he would also leak through the chastity cage she’d locked his cock away in.  The wet spot in his panties was always something she’d comment on.

 

He was never perfect in those inspections and was soon over her lap for a proper admonishment.  It was one which reddened his pert ass cheeks and made him squirm all the more.  With his rear end still stinging he would promise his Mistress to do better the next time and she would open her legs to him.  He loved serving her that way and felt he’d let her down if he hadn’t managed to bring her to at least three climaxes with his tongue before she’d pull him away from her glorious pussy.

 

But, pull him away she would and then she’d bend him over her desk and pull out her strap-on.  Being plowed by his boss and mistress over her desk while he was in his sexiest frillies was always a stupendous turn on for William.  And of late, an enormous source of frustration.  It had been well over a month since she’d granted him a release from that chastity cage.  Instead, she edged him relentlessly during those weeks.  Even the regular prostate milkings didn’t help.  They just added to the frustration as her relentless physical domination of him combined with the mental domination that such milkings entailed.  True, it relieved the physical pressure of too much cum building up in the poor man’s balls but the fact that she controlled him even to the level of forcing him to express the cum without any sexual climax just turned him on even more so.  He felt so wonderfully powerless in her grasp and under her control.

 

William, as the personal assistant to the firm’s senior executives, had access to the daily calendars of each of the executives and was responsible for scheduling their meetings and such.  Under Ms. Cortez’s guidance, William carefully scheduled time in Ms. Cortez’s daily meeting for her to have him in her office and bent over her desk.  Just as carefully, he then also scheduled time for himself to run into the Executive Washroom and “put himself back together” after his mistress had fucked him silly.  He scheduled meetings and events for the other executives such that he could be assured of having the Executive Washroom to himself as he cleaned himself up.  Mainly this meant combing out his hair and washing his face clean of Bianca’s juices. She liked smearing his face with them as he licked her to climax after climax.  Plus he would inspect his shirt and pants to be sure no lube or anything else had stained them from when she had him bent over her desk and pegged his ass.  Finally, he would gargle and brush his teeth so that Mistress Cortez’s scent was only still in his mind and not also his breath.  He was a professional in a professional office environment and thus such discretion was professionally appropriate.

 

So, William was pretty confident that he would always have uninterrupted time in that Washroom after each time his mistress had used him and had her way with him.  And also whenever Terri Simpson took him in the same fashion.  Being the “pussy boy toy” for two powerful dominant women was a dream come true for William.  It was Ms. Cortez who found him, roped him and reeled him in as her submissive.  She found she wanted to keep him around all the time so that she truly could overwhelm him with her dominance and keep him overwhelmed.  Thus she soon had him submitting to her by moving in with her to be her personal maid and body servant.  And to keep her house in order.  To further things, she then arranged to hire him as her personal assistant at work.  This not only allowed her to have him service her at work but also for her to share him with her friend, Terri.  She had similar tastes in dominating and controlling her men and William quickly found himself without a moment’s rest as he was passed back and forth between the two women.  When he wasn’t bent over Bianca’s desk at work he was bent over Terri’s.  When he wasn’t scurrying off at day’s end to rush home and prepare dinner for Bianca he was rushing over to Terri’s home to prepare dinner for her and serve her throughout the evening.  The two dominatrixes alternated weekends in having William be their house maid and body servant at their homes.  Thus, for the past year William hadn’t had a moment to himself.  It was all becoming a blur to the man.  A lovely, sex charged, dominance imbued, chastity inducing frustration filled year.  And he loved it all.

 

So as William had just finished drying off his face after washing his mistress’s juices from it, the last thing he expected was for the Executive Washroom door to be opened.  A flash of panic burst through him.  His hands flew to his shirt as he feverishly made sure it was buttoned up enough to high the lacy teddy he was wearing underneath it.  Luckily for William, he found all his buttons buttoned so he brought his hands up to his collar and began adjusting his tie.  His mind reeled in trying to come up with appropriate excuses for his being where he shouldn’t be.  If it was Mr. Wilkins, the firm’s owner, he could probably get away with some earnest apologies for his transgression.  The man was in his eighties and seemed more concerned setting up “T” times at the various golf courses than anything else.  But it couldn’t be Mr. Wilkins as William was sure he was already out of the office for a “working golf game” session.  And it couldn’t be his mistress nor Ms. Simpson as they both were at the same meeting.  That left only… Mr. Dawes.

 

William wasn’t sure what to make of Mike Dawes.  The man was about the living embodiment of what an “alpha male” should be.  At least in the legal field.  He was in his forties, powerfully built, handsome, and had an air about him that just reeked of confidence, capability, and aggression.  William had heard enough chatter from the girls in the office that he knew every one of them would be only too willing if Mr. Dawes “put the moves” on them.  William had watched as Mr. Dawes happily flirted right back at the girls in the office.  And how the man wasn’t at all subtle in admiring when an attractive woman wandered past his gaze.  He wasn’t subtle but nor was he leering.  Of late, William had caught himself feeling somewhat put out when it wasn’t him who caught the eye of Mr. Dawes like that.

 

Which was even more confusing and troubling for William because William was straight.  He rationalized to himself that his feelings were only because Ms. Cortez and Ms. Simpson always and only used him in a feminine role.  And he was always wearing such wonderfully feminine things underneath his corporate attire.  It troubled him still though.  He consoled himself that it was just due to his being somewhat over emotional during the past several months.  And that, he was assured by the doctor Ms. Cortez had sent him to, was simply due to his being so overworked.  He’d started giving William regular shots to help him “maintain a more even emotional state” and also to “help with his energy level.”

 

If those shots were supposed to help, they hadn’t.  William was now even more emotional of late.  He never had time to rest, really, unless it was after being well and truly fucked out by his mistress Bianca or Terri and thus able to get some sleep in their bed.  He’d still have the chastity cage on and they always put his hands in bondage mitts but at least he could get some sleep.

 

William was a bundle of nerves as Mr. Dawes stepped into the Executive Washroom and closed the door behind him, locking it as he did so.  He didn’t seem either surprised or upset to find William in the Washroom either.

 

“I thought I saw you slinking in here” Mr. Dawes said, pleasantly, as he strode over to stand next to William at the sinks.  Right next to him, William noticed.  Not at the end of the three sinks but right next to the one William was standing in front of.  William felt a wave of heat flush through his body and he began to stammer an excuse to Mr. Dawes.

 

“That’s alright, no need to make excuses there, William.  I know that Bianca can be quite demanding of you.  Thus it’s quite alright for you take a few minutes after her morning meetings with you to catch your breath.” He said, smilingly, as he waved aside William’s attempt at excusing himself.  William felt himself blush when he realized Mr. Dawes seemed to know just exactly how “demanding” Ms. Cortez, his mistress as well as his boss, was in those meetings.  “Or was it just his turn of phrase?” William wondered, trying to not overthink what Mr. Dawes had said to him.  Mr. Dawes gave him no further time to ponder his comments as he moved even closer to William.

 

“You having some difficulty with that tie there?” he asked.  “Here, let me help you with that.” He continued, not giving William the chance to make any objection before he stepped behind William and wrapped his arms around him to reach his tie.  “I find it easier to tie these things when I’m looking at them in a mirror myself.  Trying to get the knot right when looking directly at them doesn’t work for me.” He beamed at William. 

 

William felt himself start to sweat at how close Mr. Dawes suddenly was.  Even though Mr. Dawes was just an inch or so taller than him, William felt small with the way that Mr. Dawes had suddenly taken control of him.  Mr. Dawes was quickly and assuredly getting the knot on William’s tie straightened out and he leaned forward to see it more clearly in the mirror, audibly inhaling through his nose as he did so.

 

“Mmm… that’s an interesting scent there, William” he commented as he worked the knot and sniffed next to William’s cheek.  “That’s not cologne, and that’s not perfume either” he observed.  William blushed more furiously.  “I’ve always wondered what Bianca smelled like.  Now I know.”  Mr. Dawes said, contentedly.  William once again started to stammer an explanation but, once again, Mr. Dawes would have none of it and deftly switched the subject before William could get his words in edgewise.

 

“You know, William, shirts like yours really aren’t meant to be worn with ties.  Particularly not women’s blouses like this.”  Mr. Dawes casually observed.

 

“Women’s?  No.. sir… No, Mr. Dawes, this isn’t a woman’s shirt”  William objected.

 

“Really?”  Mr. Dawes dryly replied.  “Then why are the buttons on the wrong side?  That’s a woman’s blouse you have on there, William.”  Mr. Dawes continued as he let his hands trail down William’s torso after he’d finished knotting the man’s tie.  Mr. Dawes trailed his fingers along the side of William’s pants and around his backside.  William was frozen in place as the sensations were coursing through him and the realization of the fact that Mr. Dawes was essentially feeling him up.

 

“Hmm… and these aren’t men’s pants either.” Mr. Dawes, again, observed.  “The material’s too light, the buttons are on the wrong side again as well.” He continued.  Then, as his fingers trailed along William’s flanks, “Hmm… garters too, I see.  One, two, three, four, five… oh my, that’s quite a lot of garter straps there you have on William.  Ten?  Is that a vintage garter belt you’re wearing?  I admire such taste.  Don’t worry, they don’t show.  Much.  You would really have to know what to look for under pants – even ones as otherwise sheer as these – to see the traces of them.”

 

William’s head was spinning.  He’d no idea his lingerie had been so obvious to anyone.  Especially to someone like one of the senior executives of his firm.  He was trying to come up with something to say to Mr. Dawes but the man kept touching William and his comments kept William too off balance, mentally, for him to say anything other than half-hearted attempts at excuses.  Excuses which Mr. Dawes never allowed William the time or the space to truly make.  Mr. Dawes then trailed his hands up the sides of Williams body and brought them up to William’s chest.

 

“And I wouldn’t worry about the lingerie you’re wearing under this blouse.  The straps aren’t making enough of an indentation in your shoulders to show.  And the blouse material is thick enough that you can’t see whatever it is you’ve on under it.  But, that shirt isn’t doing enough to hide these…” he finished as his hands came to rest on William’s nipples.  Even through the material of his shirt, Mr. Dawes’ touching his nipples sent waves of pleasure through William that made him pant.  He barely managed to stifle the moan that emanated from his core.

 

William too had noticed how much more sensitive his nipples were of late.  So too had his mistresses and they’d made relentless use of that sensitivity.  When William had asked Bianca if she thought his nipples and the flesh around them looked swollen she dismissed his concerns.  She’d said it was all due to the “nipple torture” play she liked “inflicting” on him and the effects of the little pumping cylinders she had him use to enlarge his nipples.  She told him she thought large nipples on a man were sexy so he should use the nipple pump set she given him to make his nipples bigger.  That it wasn’t just the nipples themselves which were getting swollen didn’t seem to bother her.  And she kept William too busy otherwise – and could bring him to his knees just playing with those nipples – for him to have much time to worry about his “puffy and flabby” chest.  But now with Mr. Dawes cupping those lumps on his chest, William’s worries came back with force.

 

“They’re just swollen from my… my playing with them.  They’re very… sensit… oooo” William’s lustful moan managed to escape his mouth this time as Mr. Dawes smoothly worked the man’s engorged nipples.  William tried not to writhe under Mr. Dawes’ touch and then the man took his fingers off of the nipples and, instead, cupped the mounds William’s nipples were attached to.

 

“Nipple play?  Sorry, William, nipple play doesn’t create these” Mr. Dawes said confidently as he cupped and jiggled the handfuls of swollen pleasure that stuck out from William’s torso.  “I’d say these are now at least a full A cup – if not actually B’s” Mr. Dawes mused.  “I’ve been watching you change for months now.  Your shirts – your blouses – are usually loose enough that they don’t stand out too much but they’re getting harder and harder not to notice.  You didn’t have these when you started a year ago.”  Mr. Dawes concluded as he began rubbing his thumb over the protruding nipples atop William’s fleshy mounds.  Even through the material of his blouse, the sensation was electric to him.  William had to brace himself on the sink countertop as Mr. Dawes continued to overwhelm him.  William felt Mr. Dawes step fully into him and press his hips into the countertop with his own hips.  When William felt Mr. Dawes’s hardon press itself between his cheeks he let out a cry of surprise.  And his eyes fluttered as Mr. Dawes slowly ground his pants covered cock into William’s ass.

 

“So, what’s your dosage?  Which ones are you on?  Lupron?  Estradiol?  Something else?” Mr. Dawes asked in an almost breathless voice as he brought his face close to William’s throat.  William shivered as he felt the man’s hot breath on his neck.  Mr. Dawes’ touch was so sensual but so powerful.  William felt weak and helpless and out of control and was burning for more it.  Even as his lust was becoming all consuming, William also recognized how completely wrong it all was.  He was a man!  He wasn’t gay.  He was only interested in women.  Yes, he was wearing women’s lingerie and he loved when women bent him over and put their fake penises into him and fucked him like he was the girl.  But… he was straight.

 

In a voice drenched with lust, Mr. Dawes purred into William’s ear, “For weeks now - a month or two, actually – I’ve been expecting you to show up at work in a skirt and heels.  I’ve been expecting you to publicly make known that you’re “transitioning” and that you’re now to be treated as a woman.  You realize I know how to treat a woman very, very well.  Don’t you?  Don’t you, ‘William?’”

 

Mr. Dawes took one of his hands away from the mounds on William’s chest – leaving his other hand there to continue pleasuring the cross dressed man who was whimpering in lust before him – and brought it down to the front of William’s groin, pushing him away from the countertop and harder against Mr. Dawes’ rampant cock.  His fingers sought and found the expected thing between William’s legs and he was soon tapping out a rhythm upon it.

 

“As I thought, she has you caged.”  William could practically see the smirk on Mr. Dawes’s face even as he had his eyes squeezed shut and was trying to concentrate on anything other than then waves of pleasure Mr. Dawes was intent on washing away his resistance with.  “Tell me, pretty boy, does it still work?  Or have you doused yourself with so much of those hormones it’s just become a limp little thing between your legs?  Just there to look pretty?  Are you going to go all the way and have it turned inside out to make yourself a little pussy?  When’s the last time she let you out of that cage?”

 

The questions were coming too fast for William to even coherently follow let alone respond to.  The sensations Mr. Dawes was now rapping onto his trapped cock was even more erotic and distracting.  Mr. Dawes wrapping his arms around William so commandingly and his so sensuously breathing onto William’s bared throat was all almost overwhelming to him.  Mr. Dawes took his one hand away from tweaking William’s nipples and quickly popped open several of the buttons on his blouse.  Mr. Dawes deftly pushed the shirt out of the way and resumed his overwhelming William’s nipples.

 

William finally squeezed his eyes shut even tighter and drew in a deep breath to compose himself even if for but a moment and then blurted out his denial in the seconds he knew he had before he’d completely lose himself to Mr. Dawes’s overwhelming touch and embrace.

 

“No!  I’m… I’m not on any… anything.  I’m not on any hormones… I’m not!  I’m… I… They’re… They’re just energy shots… not hormones.  And…. They’re not hormones…. It’s just temporary swelling…  It’s just…” he was almost begging in his tone.  Begging for Mr. Dawes to believe him.

 

“So, do you cum when she fucks with her plastic cock?”  Mr. Dawes continued his overwhelming of the lust consumed man.  “Have you ever had a real cock inside you?  The cock of a real man?  A man who knows how to treat a girl like you?  You know there’s no comparison between a real cock and those pieces of silicon and plastic, right?  The heat of a real cock as it fills you is so very, very different.  I bet you’d be cumming, helplessly, the moment a real man’s cock pushed its way into your cute little ass…”

 

William had to squeeze his legs together as the thought of being so thoroughly possessed and filled by an actual cock caused his own trapped penis to throb even more painfully in its tight little chastity cage.  He recognized then that he’d have to do something – do something immediately – or else he’d utterly lose all control to this man overwhelming him so wonderfully.

 

Quickly then, William released his grip on the countertop and pulled Mr. Dawes’ hand off his nipple and his trapped penis.  He opened his eyes and looked at Mr. Dawes in the mirror in front of them both.  He took several more deep breaths and fought to compose himself even as the image before him threatened to undo it all.

 

What he saw was a handsome, powerful man with his arms being held away from a lovely, pretty, soft, and achingly effeminate man.  A “pretty, pretty boy” as William’s mistress kept calling him.  A man who’s hair was styled so prettily in an androgynous cut that only emphasized how feminine his features had become.  He stared at himself and the contrast between that pretty, pretty boy and the absolutely alpha male standing behind him and overwhelming him in such an irresistible and masculine a manner.

 

William’s eyes grew wide as he suddenly understood what he was seeing.  The mounds on his chest weren’t just swellings they were… breasts.  Small ones but, clearly, breasts.  And his hips, they’d become wider.  Wider, not thinner, due to all the leg work Ms. Cortez insisted he concentrate on with the personal trainer she had him go to.  “We’ll get to your upper body once we’ve got that weight situation under control” she’d told him.  But now his upper body had thinned out while his legs had toned up and his ass had become wonderfully pert and tight.  And looked so good in panties and garters and thongs and with the way she would touch him there.  With the way Mr. Dawes was touching him there….

 

“No… No..” William said to himself as the realization finally came through to him.  A realization as if he were just awakening from a dream.  A lovely, wonderful, erotic, happy dream.  But, it was only a dream – until he finally opened his eyes and awakened himself fully.

 

“No?” Mr. Dawes asked, amusedly.  “No, what?  That you’ve never been made love to be a man?  That you’ve never cum while wearing that cage?  That you’re not a pretty girly boy?  Well, you are very pretty one.  And if you’ve never had a man make love to you, William, then you’re doing a very good job of hiding how little you want one to.” He concluded with a smile.

 

“No… I’m… I’m straight.  And… I’m not on any hormones…. No, I never… I’m… a man… not a girl.  I don’t want to be a… No…  I’m straight… Please…  Please stop.”  William blurted out in a voice clearly sincere.

 

Mr. Dawes looked more deeply into William’s eyes through the mirror’s reflection and then lightly pulled his hands away and out of William’s grasp.  Standing back from William as he did so.  He then placed his hands on William’s shoulders and gently turned him around to face Mr. Dawes directly.  He gathered William’s hands in his own and brought them up to his lips.  Looking William square in the eyes, Mr. Dawes lightly kissed William’s hands and spoke to him once more.

 

“William, I’m not sure what is going on here.  You are a beautiful man who clearly is on the verge of becoming a beautiful woman.  I find that a wonderful thing and very attractive one as well.  I find you attractive.  But, if for whatever reason you don’t wish to proceed then, that is your choice and I will respect that.  And I will respect you whatever your decision.” He said, earnestly and then brought one hand up under William’s chin to raise the man’s face to his own.  “Just remember, that if you change your mind I will be delighted to be that man to make love to you.”  Mr. Dawes then leaned forward and gently kissed William on his forehead.  Then he turned and strode out of the Executive Washroom.  Leaving William standing at the side of the countertop to contemplate just what, exactly, he’d awaken himself to.

 

William turned and looked at himself in the mirror again.  The red haze of lust which had been such a constant cloud to his vision over the past many months now seemed to have finally dissipated.  Perhaps not entirely but enough for him to clearly see what he had become.  He stepped over to the Washroom door and locked it.  Then he took off the tie that Mr. Dawes had so carefully knotted and then he removed his blouse and the teddy underneath it.  He examined the mounds on his chest.  They were, undeniably, breasts.  He turned to the side and looked at his reflection in the mirror, arching his back as he did so.  He’d seen smaller breasted women – actual women – who he thought had look beautiful and sexy.  He turned fully back to the mirror and lost himself in thought as his feminized form filled his vision.

 

He’d fantasized about being forcibly feminized.  He’d read plenty of tales about it.  But he’d never thought to actually do it to himself.  And he certainly hadn’t consented to it being done to him.  But, despite that, here he was.  Here he was: a feminized man.  His skin was smooth and soft and hairless.  His frame had thinned out considerably since Ms. Cortez took him under her control.  He was thinner but… he had some curves to that thinness.  Curves that could look even more feminine and even sexier if he filled them out a bit more.  A vision of himself in a skirt raced through his mind.  A skirt.  A sexy skirt.  A nicely appropriate just above the knees skirt.  A skirt like that flipped up over his pert rounded ass cheeks.  A skirt like that flipped out of the way as his mistress drove her strap-on into that willing and eager ass.  A skirt like that flipped out of the way… by a man… By a man who’s rampant cock pressed into him instead his mistress’s fake one.  William felt his nipples harden again and a flush blossom through his body.

 

He opened his eyes again.  He realized he could do that.  He could do that vision he’d just had.  He could make that fantasy a reality.  He could now.  He was now that close.  He could become the feminine creature of his vision.  Not an actual woman.  He didn’t want to lose that much of himself.  But he could become… he could become… different.  He could become… more.  William stood there, looking at himself in the mirror and let his mind race contemplating who he was, what he was, and what he could do about it all.

 

Some time later, William was outside Ms. Cortez’s office.  He’d checked her calendar and cleared an hour on it after she’d returned from her meeting.  Normally, this would have been impudent of him to have cleared such time without clearing it through her first.  But he needed the time with his mistress.  He needed the time to confront her for what she had done.

 

He was a storm of emotions as he entered her office.  She was somewhat surprised to see him there as she hadn’t beckoned him to her side.  She was even more surprised when William turned and locked the door to her office and then strode deliberately around her desk to come next to her chair.  She turned to rein her uppity pretty, pretty boy in but William sank to his knees before her and grasped her hands in his as he brought his face to her knees.  Looking up from that position he spoke to her in a voice wracked with emotion.

 

“I’m awake now.  I’ve been sleep walking for months but, I’m awake now.  I see what you’ve done to me.  Why?  Why didn’t you ask me first?” he said to his mistress as his voice finally broke and his tears began flowing.

 

Ms. Bianca Cortez started to speak, then stopped.  Then she thought to say something else to the man kneeling at her feet.  The man supplicating himself to her.  The man weeping at how she had betrayed his trust in her.  Ms. Bianca Cortez felt her own tears begin to flow as she realize how wrong she had been.  And how badly she had wronged William.  She had failed him.  She had gone too far.  She had failed as a worthy dominant and violated the trust and the power her submissive had gifted her with.

 

Bianca moved her hands to William’s face, cradled it with them and, finally spoke to her man.

 

“I’m sorry.  I was wrong.  I was too… full of myself.  I was too sure of myself.  I… I doubted you.  I… I didn’t think you would be strong enough to do this on your own.  I.. I thought you would run away from me.  And I didn’t want to lose you.  I don’t want to lose you.”  she spoke earnestly and sorrowfully to him.  “I love you, William.  Dearly.  Fully.  I want you to be mine.  I want you to be my lover.  I want you to be my submissive.  I want you to be…”

 

“To be your what?” William interrupted in frustration and anguish. “To be your what – your man?  Or to be your girl?  You didn’t ask.  You never asked.  Why didn’t you ask?”

 

The two, submissive and mistress, supplicant and dominant, lover and lover, sat there in silence as their tears flowed.

 

“I am sorry William.  I am truly sorry.  I love you.  I want you with me.  I want you to be mine.” Bianca responded softly as she stroked the man’s hair from his face as he knelt between her legs.  “I want you to be my pretty, pretty boy.  I want you to… to stay mine.  Please?  I love you.  I should have trusted you.  I… My love… I’m sorry.  So sorry.  I should have… I…  My love…  William… I’ll make things right.  I’ll make…  William… I’m asking you now… what do you want?  How can I make this up to you?”

 

William hugged himself around his lover’s legs more tightly and through tear soaked eyes looked up her.  It took him some time to find his voice again before he could answer her.

 

Four months later, the personal assistant of Ms. Bianca Cortez was once again violating company policy by using the Executive Washroom.  This time however, it was not William Herrara looking at himself in the Washroom’s mirror as he made sure to clean his mistress’s juices from his face and freshen his breath.  Instead it was Simone Cortez Esperanza reflected in the mirror.  She’d not only just washed Bianca’s juices from her face but had now just finished reapplying her makeup.  She’d become quite good at that over those four months.  Recovering from the breast implant surgery and facial feminization surgeries had left her with little else to do but practice “the feminine arts” and with each passing day that practice put her life as William Herrara further and further behind her.

After four months the bruises were gone, the swelling had receded, and her skin had regained enough of its suppleness such that she once again had full range of motion when she moved her head to and fro.  The hormone treatment continued at its moderate level and Simone had finally felt ready enough to once again serve her lover, her mistress and her employer by going back to work at the firm.  If anything, Simone’s arrival at Wilkins, Cortez, Simpson and Dawes that Monday was something of an anticlimax.  The place was busy as usual and the other girls in the girls in the office were welcoming, in a professional way, and the men in the office were just as polite as previously but no more so.  Everyone seemed to understand that Simone was Ms. Cortez’s special employee and thus pretty much off limits otherwise. 

 

That first day had been busy for Simone.  She actually missed being at work.  She liked being busy.  She liked serving, professionally, the needs of Ms. Cortez and Ms. Simpson.  She truly needed to serve.  Doing so fulfilled her in some very deep ways.

 

Simone looked herself over in the mirror once more.  Her hair was perfect, her makeup was perfect, her lipstick was perfectly glistening.  Her skirt was perfectly just above her knees.  She looked at her watch, a delicate thing about her wrist, noted the time and then unbuttoned the top three buttons of her fitted blouse, thus barely revealing the cleavage of her wonderful new breasts.  Simone smiled at the image in the mirror and then turned on her four inch stiletto heels to stride out of the Washroom and on to the meeting she’d scheduled.

 

A moment later she was knocking on the door to Mr. Dawes’ office.  Beckoned in, Simone took a firm grip on the door handle and an even firmer one on her emotions.  She opened the door to Mr. Dawes’s office and stepped inside.  This was the first time that either of them had to actually see each other since she’d returned to work the previous day.  Before he could say anything, Simone turned and locked his office door.  Turning back, she announced;

 

“Good morning Mr. Dawes.  I have some forms here which need your review.” She spoke in as soft and feminine a voice as her practice and the trachea shave allowed.  Mr. Dawes smiled and cocked his head to one side, wondering just what Bianca’s personal assistant was up to.  He did enjoy the vision gliding toward him on those stiletto heels.  They were too high, really, for regular corporate wear but they looked fabulous on Simone’s legs.  Even without seeing their back, he guessed that her nylons were seamed and Cuban heeled, most likely.  The black skirt hugged her hips deliciously and even though it ended appropriately just above her knees he thought it was sexy as hell.  Mr. Dawes also hadn’t failed to notice both how nicely fitted her blouse was but also how the opened buttons gave him a wonderful glimpse into the new girl’s new breasts as they nicely bounced and swayed with each of Simone’s high heeled steps.  The new girl in the office was a vision of corporate sexual appeal and he savored it all.  Even as he was somewhat surprised at how crisp and professional Simone was in addressing him and how she strode around the side of his desk to park herself immediately next to him.

 

Keeping her face in a suitably neutral cast, Simone opened the folio she was carrying, bent slowly at the waist and placed two sheets of paper in front of Mr. Dawes.  She made sure to lean closer to the seated executive as she did so.  She knew her position was giving him an excellent view of her pert ass cheeks in her skirt as well as giving Mr. Dawes an ample view of how well her cleavage fill out that fitted blouse.  With her hands on his desk, Simone turned her head and looked across her shoulder and back at Mr. Dawes.

 

“The first of these forms, sir, is the memo from HR noting the change in my legal gender.  I am now Ms. Simone Cortez Esperanza and, per the gender non-discrimination policy in effect here at Wilkins, Cortez, Simpson and Dawes, I shall be treated as such.”  She paused as she looked more intensely at Mr. Dawes.  “In our last… conversation… Mr. Dawes, I recall you mentioning that you knew how ‘treat a woman,’ yes?  Well, per our company’s policy you are now legally obligated to do so with me.” Simone smiled at Mr. Dawes and ran the tip of her tongue along her teeth, just behind her lips.

 

Mr. Dawes smiled more widely and sat up straighter.  This was not the hesitant and confused William Herrara before him but someone entirely different.  A difference he liked.  Mr. Dawes then leaned forward and placed his right elbow on his desk and began looking over the forms Simone had placed before him.  His other hand found itself resting on Simone’s curvaceous ass.  That she didn’t flinch or push it away was even more encouraging to him.

 

“And now to the second form that needs your attention” Simone continued quite professionally as she shifted the next piece of paper over to Mr. Dawes.  “This memo addresses the changes to my roles and responsibilities here at Wilkins, Cortez, Simpson and Dawes since my… status… has changed.  Paragraph 3 is the most immediately relevant change that you need to now be aware of.”

 

Mr. Dawes shifted a bit closer to the desk to read the memo and began drawing his hand from Simone’s lovely ass but she reached out quickly with her own hand and stopped him.  She then read on as she began moving his hand down her taut cheeks.

 

“Paragraph 3 clearly states that I am now the Personal Assistant to all of the senior executives here at Wilkins, Cortez, Simpson and Dawes.  That it is now my responsibility to attend to all of their needs and make myself useful to them however they see fit.”  As she finished reading that paragraph she’d moved Mr. Dawes’ hand to and then under the hem of her skirt and pressed it against the flesh his fingers found there.  She sighed with pleasure as his fingers touched her smooth soft skin and began exploring on their own.

 

“All their needs?”  Mr. Dawes asked amusedly.  “All the senior staff?  Including Mr. Wilkins?  His needs as well?”

 

Simone breathed in, relishing how Mr. Dawes was feeling her supple flesh and running his fingertips across the garters they found under her skirt.

 

“Yes sir, ALL their needs.  Of course, the needs of each of the senior staff here at Wilkins, Cortez, Simpson and Dawes will be as different as the individuals involved.  I don’t think Mr. Wilkins will be requiring quite the same sort of personal assistance as does Ms. Cortez or Ms. Simpson.”  Simone paused, quite obviously, and turned to look at the handsome man who hand was wrapped around her ass cheek under her skirt.  She shifted that lovely ass closer to him and used her own hand to gently guide Mr. Dawes’ fingers down to the top of the nylon hose on her left leg and then around to its side.  His exploring fingers traced the top of the hose and the garter snaps and then felt something unexpected.

 

The crinkling the material made as his fingers encountered it, tucked into the top of the hose, and its shape brought an even wider smile to his face.  Simone purred with lust as she felt Mr. Dawes retrieve the “prize” she’d tucked into her nylons for him.

 

“So, Mr. Dawes, how can I be useful to you?  What sort of ‘personal services’ would you like me to provide you?” Simone smiled at Mr. Dawes and did so with a wicked gleam in her eyes.

 

Mr. Dawes sat back in his chair as he brought her prize up before him.  The condom packet was quite the shiny thing as he played it back and forth in his fingers.

 

“How should I make use of you?” he asked her with an equally wicked gleam in his eyes.  “What sort of ‘personal services’ do I want from you?  To be brutally frank, I do not want to make ‘use’ of you at all.  And nor do I want any ‘services’ from you either.” He said, calmly. 

 

Before Simone could draw back, Mr. Dawes continued.

 

“Instead, I would rather make love to the beautiful woman who clearly wants me to bend her over my desk and put to good use this condom she just gave me.” He concluded warmly.

 

Simone felt a blush warming her face as she also felt her nipples harden at the import of what Mr. Dawes had just said.  The man truly did know how to treat a woman.

 

“First however, my beautiful dear girl I need you here in my lap so that I can kiss you properly” Mr. Dawes said lustfully as he reached out and drew the very happy and very willing personal assistant into his lap and into his embrace.  An embrace Simone melted into even deeper as Mr. Dawes began kissing her as only a man can kiss a woman.

 

Simone truly loved her job as a personal assistant at Wilkins, Cortez, Simpson and Dawes.  She loved it even if it had taken her so long to awaken to her proper role there.


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