Discovery
of
Whimsy
genre
bisexual
Michael heard that Nic wanted to see him with some trepidation. Never a particularly brave individual, and being new to working in Nic’s company, he had become aware quite quickly of Nic’s reputation for being demanding and unforgiving. This was countenanced by Nic’s physical presence - both tall and muscular, with a deep and gravelly voice, it was not uncommon for his staff to stay out of his way.
Michael, for his part could not be more different. Only 19, married and a parent too early, of slight frame and with a slightly nervous disposition - it was imperative that he retain this job. And so he approached Nic’s office fearfully, sitting quietly in the reception as instructed. Susan, Nic’s PA seemed to have a knowing look on her face, but gave Michael no indication of why he was there.
Eventually he was directed into Nic’s office and the door was shut behind him. Nic - speaking abrasively into the phone - gestured for Michael to sit in the office chair facing him, leaving Michael to wait, again while Nic concluded his discussion. The wait was not relieved when the call finished either, as Nic then took some time making notes on his laptop.
When he did turn his attention to Michael the conversation seemed unpredictable. Nic sat back in his chair and, without greetings or preliminaries asked: “How long have you worked here Michael?”
Michael leaned forward and answered hesitantly, “Three months, sir.”
“Hmm. Susan tells me you are only 19 years old. You do look very young.”
Michael shrugged, “Yes sir. Thank you sir.”
“And yet you are both married and with a child on the way?”
“Yes sir. Where I come from that is generally how it works.”
Nic paused before his next question: “You’ve come into our accounts department. Did you ever study computing before joining the company?”
“No sir. I went to a pretty small school you know. I grew up in a quiet rural area.”
“I believe it.” Nic leaned forward. “So you don’t have much experience of the internet I would imagine.”
Michael felt the first churning of fear in his gut. “No sir. A little.”
“Here’s the problem Michael. You probably don’t realise that we track your behaviour online. It’s in your contract. We monitor what you do on our computers. Did you read your contract before signing it?”
Michael sat silent, transfixed now in fear.
“I know what you’ve been looking at Michael. Websites with boys in girls clothing, pleasing men. Explicit websites. Three or four times a week. Do you deny it?”
Michael wanted to run, fear and shame washing over him, hands trembling slightly, heart pounding, face visibly flushed. The words to respond wouldn’t come.
After a moment of silence Nic continued: “It doesn’t matter if you do. I have the evidence. And I wonder what your wife would say if she knew. Your parents. Your church members. I understand you attend quite regularly?”
Michael finally responded: “I do, sir.”
“You see, I know a little bit about these matters. You’re young. To be blunt you are a bit effeminate. I’d put money on it that you see yourself as those boys, dressing up. That you have probably done it yourself. Am I right?”
Michael felt ambushed now, aware that tears of frustration were probably visible to Nic. He remained unable to answer.
“You can stay quiet if you want, or we can have an honest conversation. Trust me, it will be better for you if we do.” After a brief pause Nic continued: “You see I don’t care what you do in your free time, but when you do it here I have some say. Your employment here is something I control. Do you understand?”
Finally Michael spoke, terrified that his employment and reputation may be at risk. “Yes sir.”
“You like dressing up, don’t you?”
Michael nodded.
“Your mother’s clothes? A sister? Your wife’s?”
“When I was younger, my mother’s clothes. Sometimes my wife now, when she’s out.”
“Nobody knows?”
Michael shook his head.
“Just panties? Full outfit? Makeup?”
Michael felt humiliated and puzzled by the intensity of this interrogation. “Sometimes a full outfit, if I have the time. Sometimes just … panties.”
“You pose in the mirror? Imagine being in public, being watched?”
Michael stayed silent, ashamed as these secrets were exposed so brutally to this torturer.
“You imagine men watching you, maybe doing more than watching, don’t you Michael?”
Michael had long stopped looking Nic in the eyes. He nodded with his head lowered meekly.
“Have you ever done it in front of anyone Michael?”
Michael shook his head.
“I’m a firm believer in the principle of knowing oneself Michael. A firm believer. It’s time you did this in front of a man or you will always be hiding.”
Michael shook his head feverishly, not looking directly at Nic. “I can’t. That’s not who I am.”
Nic turned his attention to his laptop, typed briefly. The gravity of his situation, the fear of losing his job, of exposure to his family had rendered Michael helpless, visibly trembling now. Nic turned back to the younger man:” I don’t give a fuck how you do it Michael. Next Friday you will bring a set of the most erotic clothing in your wife’s cupboard. You and I will go to a hotel, where you are going to show me what you do. Do you understand?”
Michael was almost whispering now: “I can’t. I can’t do that.”
“It’s your call Michael. Be honest with yourself and me, or face exposure and lose your job. I know which I would prefer but you must decide.”
Michael said nothing, eyes darting around the carpet.
“You’re a fucking sissy Michael. Embrace it. Deal with it. Stop hiding. Next Friday is non negotiable. Understand that. Do you have anything to say?”
Michael shook his head.
“Then fuck off and go work. I’m busy.”
The ignominy of this treatment continued as Michael almost stumbled through the door, anxious to be away from this situation as quickly as possible. Susan turned and looked at him with a wry, knowing smile and he wondered, horror stricken how much she knew. After all, the intercom between the offices could easily have been on.
Couldn’t it?
—-
As the week progressed there was no further communication from Nic and there were brief moments of respite when it seemed as if none of this was real, that Michael was safe. But day by day Friday approached, relentlessly, looming more ominously into vision. Michael cursed his own stupidity, and Nic’s dismissive, uncaring control of Michael’s life.
By Tuesday he reached the conclusion, in the lonely, dark, sleepless early hours that he could plan this; do it carefully to evade discovery; then put it behind him and return to an ordinary life. Never dress up again. Focus on his marriage, family and friends.
Planning carefully meant deliberate action. On Wednesday his wife went shopping for baby clothes. He begged off and as soon as the car turned into the road he went into his wife’s closet. He wanted to select the outfit without rushing, or risk of discovery.
Of course he knew what he found most erotic: he had done this repeatedly after all. Petticoat-pink matching brassiere and panties with a pseudo embroidery rose pattern at the top hem; light grey sheen thigh high pantyhose, elasticised at the top; satin white blouse with pseudo maritime gold buttons; a too flouncy dark grey pleated skirt to just above the knee, as a schoolgirl would wear; too-high red heels embellishing the apparently conservative ensemble, a string of pearls to underpin the housewife look. Was it necessary to add the red lipstick, the mascara, the clip-on matching pearl earrings? He unconsciously set it all aside, folding it carefully into a gym bag which he hid in a spare closet, ready for Friday.
The preparation brought him relief for it was not only the act of exposing his fantasy; it was also the duplicity towards his wife he had to overcome. He slept soundly on Wednesday for the first time in days, comforted that he ran almost no risk of discovery at home.
But Thursday night he seemed to barely sleep, and kept waking, knowing he had to move the gym bag to the car secretly without being discovered. He was up before his alarm, quietly placing the incriminating evidence in his car then consuming coffee in a vain effort to sweep away the tension and exhaustion he felt. It barely lifted through his interminable drive to work, or his efforts to work through his pedestrian daily activities.
By late morning his mood was starting to lift: perhaps Nic had forgotten; perhaps it was a joke; perhaps he was just too busy - until, just after 11 he received a terse call from Susan: “Nic says to meet him in the basement for the afternoon meeting”.
Michael walked down the stairs with his heart aflutter, eyes darting nervously. Coming into the basement he saw Nic leaning calmly on Nic’s car. As he approached, Nic addressed him in a completely different tone. “Hello Michael. Did you bring an outfit as I asked?”
“Hello sir. I did. It’s in the boot of my car.”
“Get in and we’ll drive across.”
The short drive passed in silence, as did the transfer of the gym bag; but once on the open road Nic opened the conversation: “I know you feel threatened by me. I don’t blame you; but give me…” (pausing) “… obedience and this may be a day you remember fondly always. Trust me.”
“I do feel threatened. Trapped, actually. I know that you could destroy me, you know?”
“I could, yes. But that’s not something I would do lightly. There is an element of blackmail of course; but I am also helping you find a truth about yourself. You do see that, don’t you?”
“Maybe I don’t want to explore this. Maybe I want to just keep this secret!”
“Secrets and lies stunt us Michael. If you expend all your energy in hiding, how do you grow? How do you ever find peace?” He reached across and touched Michael briefly on the arm. “You don’t believe this but I am not here to hurt you. Not for a moment.”
The car pulled in to the basement of an upmarket residential hotel. Nic led the way to the elevator which opened directly into a luxurious suite. Without ceremony Nic walked to the small bar and poured two drinks while Michael, in unfamiliar surroundings waited to receive instructions.
Nic brought Michael a heavy glass with neat whiskey on ice, then downed his immediately. “Drink up Michael - there’s far more in the bar. It may help you.”
Michael seldom drank whiskey and he tentatively sipped at the lip of the glass, but Nic placed one finger below it and lifted it to force the strong golden liquid between Michael’s lips. Then, smiling, he delivered the coup de grace: “There’s a bedroom to your left. I’m going to have another whiskey while you dress. When you come out I expect to see Michelle, not Michael. Don’t disappoint me.”
—-
Every duplicitous act requires the Rubicon moment, when the protagonist determines his own fate. Michael stood before a full length mirror in the bedroom. To proceed any further would forever mark him as a participant, not a victim. Whatever choice he now made held indelible consequences - either for his current life, or his self-image and sexuality.
When he started unbuttoning his shirt he was almost unaware of the act, so lost was he in thought. But as he progressed to transform from the slightly effeminate man to the imperfect woman he embraced that side to himself that he had hidden for so long. It felt natural, comforting even to slide the panties up his legs, to sit and draw the pantyhose carefully upwards, to adjust the skirt, wishing momentarily that he had more derrière to fill it out; then finally to apply the makeup and step uncomfortably into the heels. And more, standing before the mirror he relived the moments he had stood like this previously, feeling the temptation of the satin under the skirt, the twitching that threatened to escape from the panties and change the line of his skirt. He had no wig, of course; but many women kept their hair short and it did not detract from what he had become.
He opened the door timidly, not walking through immediately; but Nic had been waiting and watched his every move. “Come here when I can see you Michelle.”
The heels caused Michael to walk carefully, occasionally having to catch himself from twisting an ankle. Nic watched every movement with, surprisingly a momentarily tender expression which suggested he found this struggle endearing.
Finally Michael had crossed the floor to stand in front of the man that brought him to this point. Nic took a sip from his glass then twirled a finger: “Turn around and show me everything.”
Michael gingerly turned about, aware that Nic was examining all of his appearance. He had never felt so insecure, simultaneously obedient while caught up in the realisation of his own fantasy; the tension between the trapped victim and the woman longing for approval. And now it began in earnest: “Michelle - lift your skirt to show me your bottom.”
Michael closed his eyes, reached down, drew up the hem. “Higher Michelle. Higher. A little more. Ah - such beautiful panties. God. Bend forward. More. God I love when panties are pulled tight across a bottom like that. So so sexy.”
As Michael bent he felt the softest touch against the material of the panties. He closed his eyes, aware now that his emotions were being dictated by the longings of his body, his pounding heart, dry mouth and growing erection; his desire to be this woman with this strong man; his consuming need to realise this part of himself. The hand on his panties had slid between his legs, found the tension of his erection, so gently running up its length. “Do you know how beautiful you are Michelle? How I wanted this from the first moment you walked into my office, so scared; so defiant about who you are. Denying your need to be a sissy. God.”
Nic found Michael’s hand and pulled him backwards onto the settee alongside him. Michael continued staring ahead, but Nic placed a hand on his cheek and turned his face until they looked into each other’s eyes. “I know what you want, do you see? You’re a sissy. You want to be a woman. You want a man to adore you, to worship you, to treat you like a woman, to fuck you like a slut. You can’t escape it. And as much as you struggle against it, I am that man. Whoever you are elsewhere, here you are Michelle. My Michelle. My princess and my slut. “
Nic paused, as if waiting for a response. When none came he lowered his hand, still staring intently into Michael’s eyes. “I blackmailed you to be here; but you can leave and I will do nothing to stop you. I won’t hurt you in any way. You can go back to your life without any concerns.
“I leave it to you - but if you walk away you will never know, will you? This entire part of yourself will be lived in secret. Is that what you want? “
Michael’s conflict was written all over his face, but finally he spoke. “What does that mean? I can’t destroy my life for this.”
“You can live two lives Michelle - respectable family man on one side and … Michelle for me. I will respect your privacy and you respect mine. And this will be our time. “
The question hung between them for an eternity, Michael’s struggle etched on his face until he reached a decision and leaned across to softly, as a woman would, kiss Nic on the lips, sliding a tongue tip forwards.
—-
The first kiss is an exploration, and for Michelle the discovery of her womanhood. Lost in the strength of Nic‘s arms she willingly abandoned herself to her feminine desires, the joy of surrender.
Nic whispered urgently: “I must see all of you”, pulling up her skirt until her panties were exposed, engorged clitoris straining the material. He could no longer contain himself, sliding his hand into Michelle’s panties, hearing her breathing change as he gently freed her, arching her back, opening her legs and pressing herself into his hand, rock hard now, softly whimpering as she moved forward and back against him. “Gently my princess.”
In the throws of abandon, Michelle reached across, undid her lover’s trousers and exposed his equally engorged cock. “I need you in my mouth daddy.” She wanted the submissiveness she had imagined so often, getting onto her knees in front of him and finally, finally, finally after years of want, placing painted lips on his tip, then absorbing him into her mouth. He filled her, too large to take at once, obediently licking and sucking, all the while looking into her daddy’s eyes, everything she imagined. Suddenly, hands pulling her forward, she felt his cock beginning to pump as he exploded. She knew better than to pull away, hearing him call her name as she drained his want, giving her lover release as a woman should, kissing him as he softened in tender intimacy. He kept moving his hips slowly as Michelle held him gently in her mouth, swallowing everything he expelled.
Finally Nic placed a hand against her cheek. “You haven’t come yet, princess.”
“It’s alright daddy. It’s enough that you did.”
But he pulled her up, strong enough to treat her like a doll, pulling her onto his lap facing away, her legs held open by his, whispering into her ear as he gently, then firmly milked her clitoris until she could no longer contain herself and cried out, pumping into the skirt held up across her belly.
—-
Afterwards she turned and nestled into his shoulder, kissing his neck, both experiencing the calm after the release. The intimacy was complete, Michelle seamlessly surrendering to her feminine self.
“Daddy?”, running a finger slowly down his chest.
“Yes princess?”
“This is what you wanted all along, isn’t it? You were never going to expose me, were you?”
“No. At first I was going to discipline you, but something in you made me want this more. And I thought that you would only do this if you felt you had no choice. I would never hurt you like that.”
“People in the company are so scared of you. And here you are so tender and giving.”
“People think you’re a family man, and here you’re a wanton slut, a sissy finding herself.”
He paused. “We are never just one thing Michelle. Life is often too complex for that. Our desires expand to overwhelm the expectations others have of us, and if we are truthful we embrace them.”
They kissed gently, her tongue teasing his. “You’re my slut, aren’t you Michelle?”
“For as long as you want me, daddy.”
Nic reached up her skirt, cupped her bottom then ran a finger towards her anus, pressing in gently. She tensed, unfamiliar with this invasion, closing her eyes.
“You still have so much to experience princess.” His finger was on her anus now, rotating as she stiffened. Nic’s voice was deep and firm: “And I’m going to teach you every. Fucking. Thing. My sissy slut princess is going to learn all there is to know about pleasing men. Many men.”
Michelle looked, startled, into his eyes.
“Your journey is only beginning Michelle.” He slapped her bottom hard and she jerked up with a surprised cry. “It’s only the beginning.”
Michael, for his part could not be more different. Only 19, married and a parent too early, of slight frame and with a slightly nervous disposition - it was imperative that he retain this job. And so he approached Nic’s office fearfully, sitting quietly in the reception as instructed. Susan, Nic’s PA seemed to have a knowing look on her face, but gave Michael no indication of why he was there.
Eventually he was directed into Nic’s office and the door was shut behind him. Nic - speaking abrasively into the phone - gestured for Michael to sit in the office chair facing him, leaving Michael to wait, again while Nic concluded his discussion. The wait was not relieved when the call finished either, as Nic then took some time making notes on his laptop.
When he did turn his attention to Michael the conversation seemed unpredictable. Nic sat back in his chair and, without greetings or preliminaries asked: “How long have you worked here Michael?”
Michael leaned forward and answered hesitantly, “Three months, sir.”
“Hmm. Susan tells me you are only 19 years old. You do look very young.”
Michael shrugged, “Yes sir. Thank you sir.”
“And yet you are both married and with a child on the way?”
“Yes sir. Where I come from that is generally how it works.”
Nic paused before his next question: “You’ve come into our accounts department. Did you ever study computing before joining the company?”
“No sir. I went to a pretty small school you know. I grew up in a quiet rural area.”
“I believe it.” Nic leaned forward. “So you don’t have much experience of the internet I would imagine.”
Michael felt the first churning of fear in his gut. “No sir. A little.”
“Here’s the problem Michael. You probably don’t realise that we track your behaviour online. It’s in your contract. We monitor what you do on our computers. Did you read your contract before signing it?”
Michael sat silent, transfixed now in fear.
“I know what you’ve been looking at Michael. Websites with boys in girls clothing, pleasing men. Explicit websites. Three or four times a week. Do you deny it?”
Michael wanted to run, fear and shame washing over him, hands trembling slightly, heart pounding, face visibly flushed. The words to respond wouldn’t come.
After a moment of silence Nic continued: “It doesn’t matter if you do. I have the evidence. And I wonder what your wife would say if she knew. Your parents. Your church members. I understand you attend quite regularly?”
Michael finally responded: “I do, sir.”
“You see, I know a little bit about these matters. You’re young. To be blunt you are a bit effeminate. I’d put money on it that you see yourself as those boys, dressing up. That you have probably done it yourself. Am I right?”
Michael felt ambushed now, aware that tears of frustration were probably visible to Nic. He remained unable to answer.
“You can stay quiet if you want, or we can have an honest conversation. Trust me, it will be better for you if we do.” After a brief pause Nic continued: “You see I don’t care what you do in your free time, but when you do it here I have some say. Your employment here is something I control. Do you understand?”
Finally Michael spoke, terrified that his employment and reputation may be at risk. “Yes sir.”
“You like dressing up, don’t you?”
Michael nodded.
“Your mother’s clothes? A sister? Your wife’s?”
“When I was younger, my mother’s clothes. Sometimes my wife now, when she’s out.”
“Nobody knows?”
Michael shook his head.
“Just panties? Full outfit? Makeup?”
Michael felt humiliated and puzzled by the intensity of this interrogation. “Sometimes a full outfit, if I have the time. Sometimes just … panties.”
“You pose in the mirror? Imagine being in public, being watched?”
Michael stayed silent, ashamed as these secrets were exposed so brutally to this torturer.
“You imagine men watching you, maybe doing more than watching, don’t you Michael?”
Michael had long stopped looking Nic in the eyes. He nodded with his head lowered meekly.
“Have you ever done it in front of anyone Michael?”
Michael shook his head.
“I’m a firm believer in the principle of knowing oneself Michael. A firm believer. It’s time you did this in front of a man or you will always be hiding.”
Michael shook his head feverishly, not looking directly at Nic. “I can’t. That’s not who I am.”
Nic turned his attention to his laptop, typed briefly. The gravity of his situation, the fear of losing his job, of exposure to his family had rendered Michael helpless, visibly trembling now. Nic turned back to the younger man:” I don’t give a fuck how you do it Michael. Next Friday you will bring a set of the most erotic clothing in your wife’s cupboard. You and I will go to a hotel, where you are going to show me what you do. Do you understand?”
Michael was almost whispering now: “I can’t. I can’t do that.”
“It’s your call Michael. Be honest with yourself and me, or face exposure and lose your job. I know which I would prefer but you must decide.”
Michael said nothing, eyes darting around the carpet.
“You’re a fucking sissy Michael. Embrace it. Deal with it. Stop hiding. Next Friday is non negotiable. Understand that. Do you have anything to say?”
Michael shook his head.
“Then fuck off and go work. I’m busy.”
The ignominy of this treatment continued as Michael almost stumbled through the door, anxious to be away from this situation as quickly as possible. Susan turned and looked at him with a wry, knowing smile and he wondered, horror stricken how much she knew. After all, the intercom between the offices could easily have been on.
Couldn’t it?
—-
As the week progressed there was no further communication from Nic and there were brief moments of respite when it seemed as if none of this was real, that Michael was safe. But day by day Friday approached, relentlessly, looming more ominously into vision. Michael cursed his own stupidity, and Nic’s dismissive, uncaring control of Michael’s life.
By Tuesday he reached the conclusion, in the lonely, dark, sleepless early hours that he could plan this; do it carefully to evade discovery; then put it behind him and return to an ordinary life. Never dress up again. Focus on his marriage, family and friends.
Planning carefully meant deliberate action. On Wednesday his wife went shopping for baby clothes. He begged off and as soon as the car turned into the road he went into his wife’s closet. He wanted to select the outfit without rushing, or risk of discovery.
Of course he knew what he found most erotic: he had done this repeatedly after all. Petticoat-pink matching brassiere and panties with a pseudo embroidery rose pattern at the top hem; light grey sheen thigh high pantyhose, elasticised at the top; satin white blouse with pseudo maritime gold buttons; a too flouncy dark grey pleated skirt to just above the knee, as a schoolgirl would wear; too-high red heels embellishing the apparently conservative ensemble, a string of pearls to underpin the housewife look. Was it necessary to add the red lipstick, the mascara, the clip-on matching pearl earrings? He unconsciously set it all aside, folding it carefully into a gym bag which he hid in a spare closet, ready for Friday.
The preparation brought him relief for it was not only the act of exposing his fantasy; it was also the duplicity towards his wife he had to overcome. He slept soundly on Wednesday for the first time in days, comforted that he ran almost no risk of discovery at home.
But Thursday night he seemed to barely sleep, and kept waking, knowing he had to move the gym bag to the car secretly without being discovered. He was up before his alarm, quietly placing the incriminating evidence in his car then consuming coffee in a vain effort to sweep away the tension and exhaustion he felt. It barely lifted through his interminable drive to work, or his efforts to work through his pedestrian daily activities.
By late morning his mood was starting to lift: perhaps Nic had forgotten; perhaps it was a joke; perhaps he was just too busy - until, just after 11 he received a terse call from Susan: “Nic says to meet him in the basement for the afternoon meeting”.
Michael walked down the stairs with his heart aflutter, eyes darting nervously. Coming into the basement he saw Nic leaning calmly on Nic’s car. As he approached, Nic addressed him in a completely different tone. “Hello Michael. Did you bring an outfit as I asked?”
“Hello sir. I did. It’s in the boot of my car.”
“Get in and we’ll drive across.”
The short drive passed in silence, as did the transfer of the gym bag; but once on the open road Nic opened the conversation: “I know you feel threatened by me. I don’t blame you; but give me…” (pausing) “… obedience and this may be a day you remember fondly always. Trust me.”
“I do feel threatened. Trapped, actually. I know that you could destroy me, you know?”
“I could, yes. But that’s not something I would do lightly. There is an element of blackmail of course; but I am also helping you find a truth about yourself. You do see that, don’t you?”
“Maybe I don’t want to explore this. Maybe I want to just keep this secret!”
“Secrets and lies stunt us Michael. If you expend all your energy in hiding, how do you grow? How do you ever find peace?” He reached across and touched Michael briefly on the arm. “You don’t believe this but I am not here to hurt you. Not for a moment.”
The car pulled in to the basement of an upmarket residential hotel. Nic led the way to the elevator which opened directly into a luxurious suite. Without ceremony Nic walked to the small bar and poured two drinks while Michael, in unfamiliar surroundings waited to receive instructions.
Nic brought Michael a heavy glass with neat whiskey on ice, then downed his immediately. “Drink up Michael - there’s far more in the bar. It may help you.”
Michael seldom drank whiskey and he tentatively sipped at the lip of the glass, but Nic placed one finger below it and lifted it to force the strong golden liquid between Michael’s lips. Then, smiling, he delivered the coup de grace: “There’s a bedroom to your left. I’m going to have another whiskey while you dress. When you come out I expect to see Michelle, not Michael. Don’t disappoint me.”
—-
Every duplicitous act requires the Rubicon moment, when the protagonist determines his own fate. Michael stood before a full length mirror in the bedroom. To proceed any further would forever mark him as a participant, not a victim. Whatever choice he now made held indelible consequences - either for his current life, or his self-image and sexuality.
When he started unbuttoning his shirt he was almost unaware of the act, so lost was he in thought. But as he progressed to transform from the slightly effeminate man to the imperfect woman he embraced that side to himself that he had hidden for so long. It felt natural, comforting even to slide the panties up his legs, to sit and draw the pantyhose carefully upwards, to adjust the skirt, wishing momentarily that he had more derrière to fill it out; then finally to apply the makeup and step uncomfortably into the heels. And more, standing before the mirror he relived the moments he had stood like this previously, feeling the temptation of the satin under the skirt, the twitching that threatened to escape from the panties and change the line of his skirt. He had no wig, of course; but many women kept their hair short and it did not detract from what he had become.
He opened the door timidly, not walking through immediately; but Nic had been waiting and watched his every move. “Come here when I can see you Michelle.”
The heels caused Michael to walk carefully, occasionally having to catch himself from twisting an ankle. Nic watched every movement with, surprisingly a momentarily tender expression which suggested he found this struggle endearing.
Finally Michael had crossed the floor to stand in front of the man that brought him to this point. Nic took a sip from his glass then twirled a finger: “Turn around and show me everything.”
Michael gingerly turned about, aware that Nic was examining all of his appearance. He had never felt so insecure, simultaneously obedient while caught up in the realisation of his own fantasy; the tension between the trapped victim and the woman longing for approval. And now it began in earnest: “Michelle - lift your skirt to show me your bottom.”
Michael closed his eyes, reached down, drew up the hem. “Higher Michelle. Higher. A little more. Ah - such beautiful panties. God. Bend forward. More. God I love when panties are pulled tight across a bottom like that. So so sexy.”
As Michael bent he felt the softest touch against the material of the panties. He closed his eyes, aware now that his emotions were being dictated by the longings of his body, his pounding heart, dry mouth and growing erection; his desire to be this woman with this strong man; his consuming need to realise this part of himself. The hand on his panties had slid between his legs, found the tension of his erection, so gently running up its length. “Do you know how beautiful you are Michelle? How I wanted this from the first moment you walked into my office, so scared; so defiant about who you are. Denying your need to be a sissy. God.”
Nic found Michael’s hand and pulled him backwards onto the settee alongside him. Michael continued staring ahead, but Nic placed a hand on his cheek and turned his face until they looked into each other’s eyes. “I know what you want, do you see? You’re a sissy. You want to be a woman. You want a man to adore you, to worship you, to treat you like a woman, to fuck you like a slut. You can’t escape it. And as much as you struggle against it, I am that man. Whoever you are elsewhere, here you are Michelle. My Michelle. My princess and my slut. “
Nic paused, as if waiting for a response. When none came he lowered his hand, still staring intently into Michael’s eyes. “I blackmailed you to be here; but you can leave and I will do nothing to stop you. I won’t hurt you in any way. You can go back to your life without any concerns.
“I leave it to you - but if you walk away you will never know, will you? This entire part of yourself will be lived in secret. Is that what you want? “
Michael’s conflict was written all over his face, but finally he spoke. “What does that mean? I can’t destroy my life for this.”
“You can live two lives Michelle - respectable family man on one side and … Michelle for me. I will respect your privacy and you respect mine. And this will be our time. “
The question hung between them for an eternity, Michael’s struggle etched on his face until he reached a decision and leaned across to softly, as a woman would, kiss Nic on the lips, sliding a tongue tip forwards.
—-
The first kiss is an exploration, and for Michelle the discovery of her womanhood. Lost in the strength of Nic‘s arms she willingly abandoned herself to her feminine desires, the joy of surrender.
Nic whispered urgently: “I must see all of you”, pulling up her skirt until her panties were exposed, engorged clitoris straining the material. He could no longer contain himself, sliding his hand into Michelle’s panties, hearing her breathing change as he gently freed her, arching her back, opening her legs and pressing herself into his hand, rock hard now, softly whimpering as she moved forward and back against him. “Gently my princess.”
In the throws of abandon, Michelle reached across, undid her lover’s trousers and exposed his equally engorged cock. “I need you in my mouth daddy.” She wanted the submissiveness she had imagined so often, getting onto her knees in front of him and finally, finally, finally after years of want, placing painted lips on his tip, then absorbing him into her mouth. He filled her, too large to take at once, obediently licking and sucking, all the while looking into her daddy’s eyes, everything she imagined. Suddenly, hands pulling her forward, she felt his cock beginning to pump as he exploded. She knew better than to pull away, hearing him call her name as she drained his want, giving her lover release as a woman should, kissing him as he softened in tender intimacy. He kept moving his hips slowly as Michelle held him gently in her mouth, swallowing everything he expelled.
Finally Nic placed a hand against her cheek. “You haven’t come yet, princess.”
“It’s alright daddy. It’s enough that you did.”
But he pulled her up, strong enough to treat her like a doll, pulling her onto his lap facing away, her legs held open by his, whispering into her ear as he gently, then firmly milked her clitoris until she could no longer contain herself and cried out, pumping into the skirt held up across her belly.
—-
Afterwards she turned and nestled into his shoulder, kissing his neck, both experiencing the calm after the release. The intimacy was complete, Michelle seamlessly surrendering to her feminine self.
“Daddy?”, running a finger slowly down his chest.
“Yes princess?”
“This is what you wanted all along, isn’t it? You were never going to expose me, were you?”
“No. At first I was going to discipline you, but something in you made me want this more. And I thought that you would only do this if you felt you had no choice. I would never hurt you like that.”
“People in the company are so scared of you. And here you are so tender and giving.”
“People think you’re a family man, and here you’re a wanton slut, a sissy finding herself.”
He paused. “We are never just one thing Michelle. Life is often too complex for that. Our desires expand to overwhelm the expectations others have of us, and if we are truthful we embrace them.”
They kissed gently, her tongue teasing his. “You’re my slut, aren’t you Michelle?”
“For as long as you want me, daddy.”
Nic reached up her skirt, cupped her bottom then ran a finger towards her anus, pressing in gently. She tensed, unfamiliar with this invasion, closing her eyes.
“You still have so much to experience princess.” His finger was on her anus now, rotating as she stiffened. Nic’s voice was deep and firm: “And I’m going to teach you every. Fucking. Thing. My sissy slut princess is going to learn all there is to know about pleasing men. Many men.”
Michelle looked, startled, into his eyes.
“Your journey is only beginning Michelle.” He slapped her bottom hard and she jerked up with a surprised cry. “It’s only the beginning.”
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