*****
Diary Excerpt One:
“Following the threat of a sexual harassment lawsuit, the second such threat levied against me by two separate Personal Assistants the suits in HR, in light of my skills and results, decided to give me one last chance before they would be forced to take additional disciplinary actions. In an effort to reduce the likelihood of a repeat scenario they decided to assign me a PA that they assumed, correctly, would not be to my tastes. However, they did not take into account how much to his tastes I would be.”
*****
Ayesha drummed her fingers irritably against the corner of her desk as the representative from HR vacated her office, like a zebra fleeing from a lion it’d just asked politely to stop eating its herd, leaving her with a storm hanging over her head. Susan, her most recent PA, had been perfect, tight little body, perfectly presented, meek and shy. Just the kind of girl Ayesha had lusted after.
One fateful office party and a few too many victory shots and, as had happened with her previous, previous PA, Ayesha had gotten ‘a little flirty’. At least that been her wording, it sounded better at the tribunal compared to the wording Susan had presented, ‘cornered, pinned and forced into a deep kiss’. Ayesha had thought Susan had been into it up until a point. That point being when Ayesha had woken up the following morning with a migraine, a sore nutsack from a swift knee and three missed calls from HR.
However, Ayesha was fortunate, she was so damn good at her job that they couldn’t afford to get rid of her. At the end of the day, the fact was that the out of court settlements the two claimants had cost her company amounted to less than it would if they lost her and were forced to re-recruit for her position. Despite this, they had told her that a third such lawsuit and they would be forced to drop her anyway, lest news started leaking out about her antics. While she was unsure if they would genuinely hold to their three strikes policy in this regards, she didn’t fancy her chances if she pushed them.
And so she sat, brooding and waiting for her new personal assistant to arrive. The scourge of her life, both professionally and personally. A man.
Alex stood in one of the office's bathrooms, eying himself over in the mirror, drawing in a few deep breaths as he calmed himself. He knew of Ayesha, or Ms Jones, as he would have to refer to her as. Her escapades and constant involvement with HR had become somewhat of an office legend, though personally it only made him jealous, as he had moved about the office in his role as PA to one of the other directors he had always made the extra effort to steal a glance at her whenever he could.
Though he had to admit to himself, there couldn’t be any more of a contrast between them.
He stood at a modest five foot eight, compared to her towering six two. He had a slender, though not toned body. She was a little heavier set, a curvy woman with a softness to her form that enticed him, her breasts, hips and butt substantially larger than that of virtually any of the predominantly skinny woman in the organisation and certainly, at least to him, the most attractive. Where his skin was light, hers was dark, where his hair was fair, hers was black. Where he was shy and introspective she was forward and outgoing.
But nevertheless, despite all their differences, without even knowing his name she had set up residence in his heart, which made him feel at odds with himself. He knew she was interested in women and he knew that was something he’d never be. Despite any suppressed desires he might have floating around in his mind.
All this meant that today wasn’t just the start of a new job and a new work day for Alex, but of an opportunity. While there might not be any chance of romance with her, he would at least be by her side for hours each day, helping her with her work, able to speak to her, get to know her, maybe let her get to know him. If he was lucky and he played his cards right, maybe the two of them could grow to be friends. At the very least, she would, he knew, value him as an assistant. He wasn’t a proud person by any stretch, but he knew he was good at what he did.
He ran a hand through his short blonde hair, ensuring it was as smart as could be before applying his warmest of professional smiles, trying to radiate confidence as he adjusted his suit, leaving the bathroom and making for the fabled office of Ms Jones.
Ayesha glanced up from her laptop as a young man knocked on the door to her office before pushing open the door, smiling warmly at her as he stepped forward to her desk with a professional gait, every step and movement measured.
“Ms Jones? I’m Alex, I’ve been assigned as your new PA. I hope I can prove myself valuable to you.” he said, warm and friendly, standing with his hands clasped behind him, almost as if at attention as he presented himself to her for inspection.
She eyed him over with a critical eye, while she couldn’t deny there was a certain femininity to the youthful man, there was far too little of it to catch her full attention.
She let out a soft sigh, already missing the dainty girls she had driven away and nodded, putting on a slight, tired smile. “Yeah yeah, it’s good to meet you Alex.” she said, trying to hide her disappointment in her voice, adopting a professional tone, “I’m sure we’ll get along.. Great.” she nodded a little, though her voice was still noticeably uncertain.
With the tribunal, the meetings with HR and now a new PA that failed to provide her with the eye candy that she was sure was half the point of having a PA, for morale purposes, of course, she felt more than a little drained.
Alex drank in the view of her with a quick glance before smiling as he stepped away from her desk, “I’ll just set myself up on the desk just outside your door Ms Jones, if you need anything you’ve only to ask.”
She nodded plaintively and mumbled a half hearted thank you before watching him retreat to the door. His ass was okay, she supposed. But nothing to write home about.
As he shut the door leaving her in her office alone she leaned back in her seat and pulled up his personnel file, brief and CV, she felt if she was going to have to work with him she should at least see what he was about. Because of the misfortune of his gender, he wouldn’t have been her first choice, in truth he hadn’t even of been her tenth, Ayesha would’ve picked a wholly incompetent female PA over a man, but those days were past her now so she had to judge him on merits other than that. Fortunately, his file seemed to come with glowing recommendations.
She read through the notes on him, trying to assess what level of work she could start him off on to get him out of her hair and let him settle into his new role.
Parts of his file seemed to read like a corporate buzzword conference. Motivated, passionate, driven, proactive.
She couldn’t help but smirk at that last one. A proactive PA? What did that even mean? It wasn’t like a PA could do Ayesha’s work before she had given it to him.
As she shook her head, reading through the list and starting to believe that the entirety of this man's career had been built on Buzzword Bingo he knocked on her door, pushing it open.
She blinked and looked up from her laptop, brow furrowing, surprised to see him so soon without having asked him to come back in. She parted her lips to speak, then closed them, noticing the large white mug he carried in his hand, steam curling off of it.
He walked over towards Ayesha, smiling politely as he set it down beside her, not so much saying a word before turning to leave.
As he got to the door she spoke, her voice suspicious, “Coffee, milk, two sugars?..”
He looked over his shoulder, tilting his head slightly, one hand holding the door, “Yes Ms Jones?”
She hesitated, eying the mug and then him in turn. “..How did you know how I took it? How did you know I wanted one?”
He smiled then, a bright, infectious smile that she almost found herself sending back his way. “Oh.. Lucky guess?” he shrugged, “If you need me for anything…” he nodded some leaving the rest unsaid and shut the door behind him, leaving her once more to his file and her coffee.
Ayesha picked up the steaming mug in her hands and felt the heat seep through to her fingers, her full lips forming a smile as she let the scent of the coffee fill her mind. “Mm.. A proactive personal assistant.. This could be interesting..”
*****
Diary Excerpt Two:
“Alex’s skill, dedication and devotion impressed me to no end during his first few weeks working alongside me. It didn’t take me long to realise his obvious attraction for me, which was frankly adorable in itself if only for how hard he tried to hide it, but the way it manifested certainly caught my attention. In all my years working I’d never had a PA so willing to go the extra mile, so ready to help me and so quick as to supply me with what I needed before I had the sense to ask for it. While professionally our partnership was having an obvious impact on my work output and quality, personally I had to admit a growing fondness for him. Though still not to my tastes sexually, I couldn’t recall the last time someone had been so happy just to see me and so eager to please. It was just my luck that Alex had a loose thread in his life that would lead to what I wanted, and I just couldn’t help but pull on it.”
*****
“No. No no no no, fuck! No!” Ayesha swore with increasing desperation as she stared at the rotating little circle in the centre of her greyed out screen. She could see the words written on it still, one page of forty on her seemingly frozen laptop.
She grit her teeth and glanced around helplessly, her laptop had done this once or twice before, always resulting in her losing whatever she had been in the middle of. She hadn’t thought much of it before, it had cost her a few small email drafts but it was just more of an inconvenience than anything major, and one her IT department had assured her they had resolved.
And yet, here she sat, on the verge of losing near enough a day's worth of work, due tomorrow, to the void that was a PC crash. Yes, she was guilty of working from home and yes, she was guilty of working past office hours, but she had to be to keep ahead of the game and in her haste, she had neglected to make saves often.
“Fuck fuck fuck fuck..” She repeated, eying the laptop severely, unable to sit still as her panic started to settle in.
She pulled out her phone and glanced at the time, eleven pm. The last techie would’ve left the office hours ago, she was dead in the water and she knew it, a sinking feeling settling in on her chest.
Ayesha bit her lip and opened her contacts list, desperate and without thought, just needing rescue, there, prominently displayed at the top, was Alex.
Over the last few weeks he had proved himself resourceful and helpful in every situation she had thrown his way, if anyone could help her, she was genuinely certain it would be him.
Alex let out a low groan as his phone buzzed beside him on his bedside table. Blinking wearily he scooped up the phone, swiping right with his finger to answer as he lazily smushed the phone into the side of his face.
“Mm..Alex yes hi.”
“Alex?! It’s Ayesha!”
Her voice and the tone she held pulled him quickly from sleep, the panic in her voice was barely controlled “A-Ayesha? Whats wrong?”
“It’s my laptop, it’s crashed and I haven’t saved that document I’ve been working on all day, is there any way I can get it back?”
Alex sat up some in his bed, rubbing his head, trying to get his thoughts in order, “I uhh.. I mean.. Yeah? Probably but I couldn’t really talk you through it.. If um.. You give me like an hour I can meet you at the office?..”
“Too long, I’ve got your address, I’ll be there in twenty minutes.”
Alex opened his mouth to respond but the phone clicked silent, she had hung up.
He blinked and moved his phone, staring down at the screen, noticing the time, he’d only been in bed for an hour or so before she’d rang, but still, she was coming here? Now?
He swung his legs out of bed and rubbed at his sandy blonde hair, standing up wearily and moving to pull on a pair of shorts as he looked around his room, he would have to tidy up a bit before she arrived. Despite the cleanliness of his apartment, there were items laying around of a more personal nature that he couldn’t afford her to see.
Ayesha made better time than she had expected, throwing her car through the streets towards Alex and his apartment, she had based her estimate of how long it was going to take for her to get there on her usual travel times and she had neither taken into account her own anxiety or the lack of traffic on the late night streets.
She felt akin to an ambulance driver, referring to the laws of the road as more of guidelines with a vital, hopefully not terminal patient in the seat beside her, little circle spinning ominously as she chewed her full dark lip.
It was due to her speed that Alex had only managed a cursory sweep of his apartment by the time he heard a not so polite knock on his door, raising his eyebrows at a clock on the wall as he noted how quickly she had gotten here. He approached the door and briefly checked the peephole, confirming it was Ayesha before letting the door swing open.
“Ayesha, that was fast, I-..” He blinked as she pushed a laptop into his hands, the taller woman standing over him, them both sharing a moment as they assessed one another.
She stood tall and dark in the light of his apartment, her usually pristine office suit unkempt, her long black hair more than a little dishevelled and free of its usual ponytail.
He too looked far from the usual scope of the professional neatness he strived to maintain in her presence, his hair mussed from his pillow, his eyes heavy with sleep and in his rush to clear things away, merely wearing a pair of plain grey boxer shorts, displaying his slender body and warm white skin.
Even in Alex’s sleep deprived state, he had gotten to know Ayesha well. “..There’s a bottle of whiskey on the cabinet, glasses above. Leave this with me.” he nodded, trying to smile reassuringly and was rewarded with a relieved smile of Ayesha’s own, exhausted but grateful.
He watched her retreat into his kitchen his eyes momentarily glued Ayesha’s wide hips swaying her thick ass enticingly at him as she walked, a hand running through her hair as she let out a long sigh. H
e looked down at the laptop in his hands, biting his own lip as he observed the little circle. He moved to take a seat on his sofa, tucking his legs up comfortably under himself, still only in his grey boxers but not too bothered by it, he knew she wouldn’t be.
Ayesha stepped into the kitchen and leaned on the counter, staring at the bottle of whiskey as she tried to re gather her thoughts and calm her anxieties. Her laptop was in Alex’s capable hands, he hadn’t failed her yet and she had faith in him.
She took a glass and poured herself a hefty measure, swigging it back before pouring another.
In fact, if he couldn’t retrieve the file she was sure it wouldn’t have been recoverable. Not his fault, nor her fault, save for the forgetting to save the file. It would just have to be chalked up to a very unfortunate accident, one, doubtless, she would be paying for over the next few weeks at work. But such was work sometimes. And even in that worst case scenario, she would have Alex by her side, helping her out of the hole she had dug herself in.
As that thought helped her relax she took the opportunity, taking a more delicate sip from the whiskey this time, actually noting the flavours and spices instead of just throwing it back, to observe Alex’s home now her attention was freed from the panic of getting her laptop to him, finding herself innately curious about him and how he lived outside of work.
She was frankly, stunned. She had expected a bachelor's pad given his young age and single status. But to her surprise, her personal assistant’s kitchen was pretty spotless. She would’ve suspected, under different circumstances, that had he had prior knowledge to her arriving that he would’ve deep cleaned the entire apartment for her benefit, but she had arrived with little to no warning. The dishes were clean, the surfaces spotless, everything was beautifully decorated with a beautiful array of pastel colours that complemented one another.
Swallowing back another mouthful of whiskey she moved over to the tall fridge, her curiosity still driving her as she pulled it open, glancing inside.
It was fully stocked, and not just with microwavable meals and snacks like her own, no, genuine produce. Meats, dairies, fruits and vegetables.
Judging by a couple of boxes of leftovers which she spied, he seemed more than capable of cooking with the medley of ingredients. She raised her eyebrows peering inside one of the boxes revealing a selection of cookies. It seemed he baked too, no less.
The picture of the Alex she had in her head, the modest, kind, well presented young man at work who she assumed lived off of takeaways and spent evenings binging on Netflix and browsing the web was quietly reforming in her mind into something completely different.
Pursing her lips she closed the fridge and topped up her glass, walking back through to his living room and with another deep sigh sat herself down on one of the chairs, it’s frame creaking slightly, reminding her, to her chagrin, that her diet wasn’t going as well as she had hoped it would, as it never did.
He didn’t look away from her laptop as she entered, his brow furrowed slightly as he worked on the machine, giving her an opportunity to relax in his chair, enjoy his whiskey and eye him over again in this new light.
She had often dismissed his looks, he was clean, well presented and professional at work, as she would expect from a PA, but seeing him as he was now she could see those roots delved a lot deeper.
His fingernails, for example, were always clean, cut and managed, as she would expect. However so too, she could see, were his toenails, implying he didn’t manage them as a part of his uniform or for anyone's benefit other than his own.
He was, as always, cleanly shaven, again as she would expect from a PA. But this was eleven PM. Unless he shaved before bed, which she doubted, she guessed he just didn’t grow facial hair. She noted from what she could see, that the rest of his body too was without hair, giving his slender body a more feminine look to it.
She frowned a little at her own thoughts. She was attracted to women, that much she knew for a fact. But what was it exactly about women that attracted her? As she sat there, cradling her whiskey and watching him she realised that many of the aspects she looked for in a partner were present in Alex.
His body, while flat chested, narrow hipped and short of anything she would describe as a booty, was slender and smooth with flawless skin, his face while sporting some masculine aspects was attractive nevertheless, with his bright eyes, light hair and full lips.
She sipped her whiskey. He was cute, and took care of her, and could clearly take care of himself.
She glanced down into the honey warm colours of her whiskey, eyeing it with suspicion. The last two times she had drank in the company of her PA’s she had lost an edge of control and ultimately, lost both PA’s as a result of her subsequent actions.
She wondered whether that was that all this was, alcohol again fueling her to make moves on someone she usually wouldn’t. She looked up at him once more and found herself staring, her thoughts conflicting. He was a he, but looking past that, she saw something she liked.
After a few minutes she felt a rise of another sort, clearing her throat a little awkwardly to break their silence, “Er.. May I use the bathroom?” she asked, looking up and across at him, sat with his legs tucked under him, a notably feminine pose she noted.
“Oh um, second door on the left.” He said, indicating the direction a polite wave of his hand, not looking up from her screen.
She nodded some and placed her whiskey down, standing and moving the way he had indicated.
She stepped into the bathroom and locked the door behind her, lifting the seat to his toilet and freeing her flaccid member, hefting it in one hand and started to relieve herself.
She glanced around as she did, hoping for more clues about who was seeming to be a budding metrosexual.
He had a whole range of soaps, most of which sporting decidedly fruity titles and she noticed she had never picked up on him wearing any sort of cologne or aftershave, further reinforcing her theory that he had no need to shave.
The bath and shower unit had the curtain pulled back, obscuring it and she found her curiosity again rising, wondering whether he would he have bath bombs too, or maybe a line of scented candles lining the wall.
She finished relieving herself and tucked herself away, flushing the toilet to mask the sound of her drawing back the shower curtain.
Ayesha blinked. Frozen in surprise, her full lips pursing as her eyebrows raised.
She had expected a few things, but she hadn’t expected a silicone cock to be suction cupped to the wall, an item that in Alex’s cursory sweep he had failed to remember was stuck in place. Casually and without comment or even thought she moved the shower curtain back to where it had been, washing her hands and leaving the bathroom.
Alex glanced up as Ayesha walked back from the bathroom, sitting back in her place and looking across to him. Her expression was hard to read, a heady mix of many emotions it seemed, he tried to give her another reassuring smile but her expression was unchanged.
She continued to stare at him even as he looked back to her laptop, trying, once again, to figure out what to make of him since her second illusion of who he was had been shattered.
She observed him for several minutes, her mind turning over all the information she had gleaned about him. His mannerisms, his presentation, his lifestyle, his actions, poses, choices of words. She was forming a more complete picture of him now in her mind.
“New shorts?” She asked, casually.
He looked up, surprised not only to hear her making conversation but at the opener she had apparently decided to take.
“Er.. Yes. First time on.”
She eyed him plainly, seeing him now for who he was. She leaned forward, putting her elbows on her knees, adopting an almost corporate position. She knew now who Alex was and she knew now what it was she wanted. She hadn’t gotten to where she was by letting opportunities slip through her fingers, after all.
“I guess you usually wear ladies underwear, right?” she asked, lightly.
He paused in his work, looking up at her with wide eyes, like a deer caught in the headlights. She could see him trying to assess her, trying to figure out if she was just joking.
“I..”
“You do though, don't you?” she pressed, having no time for the excuses she was sure he was concocting.
He flushed with colour, embarrassment and shame. All the answer she needed, really.
“Excellent.” She said, sounding relieved as she leaned back in her chair, adopting a relaxed pose.
“W-what?” The look of confusion on his face as he spoke made her smirk.
“Excellent!” she repeated, “For a second there I was getting worried I was starting to fall for a real man.” She smiled, finishing her whiskey and setting down the empty glass.
“I… I think I need you to explain what you mean..” Alex responded, looking more than a little lost, his embarrassment, confusion and shame evidenced by his expression pose and voice. He was certainly no poker player.
She smiled at him, warm and genuine, her eyes bright. “Let me take you out to dinner, tomorrow night. You and me, not work, just.. Us.”
“W-where has this come from?” His look of bewilderment caused her smirk to widen.
“You aren’t interested?”
“Of course I am!” He said, then cleared his throat, trying to rein in his eagerness, a blush creeping onto his cheeks, “Err, I am, yes, but.. Why?”
“You get me. You know? I don’t just mean at work, you aren’t just doing the work I’m telling you to.. If I have a tough report, you’ll not only help me however you can with it, but you’ll bring me a drink, you’ll make me smile to keep my spirits. You’ll make me feel better about it, and myself. That and I don't really get people looking at me like you do.”
He bit his lip, looking her over, she looked more disheveled than she often did, sure, but she was Ayesha. Tall, dark, beautiful.
“Like I do?..” he asked, uncertain.
“Like you want to see me without my clothes on.” she teased.
His blushed deepened but confusion still dominated his expression “I thought you were.. You know?..” He asked, tentatively, but was only met with silence, forcing him to continue, “Well, you know.. A lesbian.”
She let out a little laugh, “I guess that's no secret with my record huh.. Well, sexuality isn’t black and white. You of all people should know that.. And I’m sure I can still be a lesbian, sort of, since deep down you want to be a woman.” she said, she was sure she was right, but it was still a gamble.
“W-what on earth makes you think that.” he asked, defensive, ashamed.
She pursed her lips and put on a gentle tone, “Just a combination of lots of little things.. You know, how you live, how you dress, how you act, how you present yourself. You seem to delight in femininity and shun the masculine.”
“That could mean anything, I might just like to keep things clean and tidy,” he protested. “I could be completely straight!”
“Then there's the dildo stuck to your shower wall..” she eyed him with a playful smirk.
“.....Oh.. Well.. I”
“Yeah. Oh.” She laughed.
He stayed silent for a few long moments, trying to figure out a way to deny it all, to save himself, but saw none. Everything she had said was true and by her confident expression, she knew it.
He tried instead to work things over in his head, tried to understand the complexities of a relationship with Ayesha. He found her attractive and doted on her every whim, this was in a sense a dream come true for him, but he couldn’t help but question it. He could never provide her with the woman she wanted sexually and he knew she couldn’t provide him with the part he desired sexually. They couldn’t have been more incompatible in that respect. But she wanted him all the same. And he couldn’t let it slip away.
“You aren’t put off by.. All that stuff you just said?” he asked tentatively.
She shook her head, “The opposite, it means I’m interested.” she said, which only served to confuse him further, “I think there's a real opportunity between you and me.. So how about it? Want to date your boss?”
He swallowed some and nodded, a genuine, albeit tentative smile forming. “I do, yes, if you’ll have me.”
They looked at one another for a few long moments, unsure how to proceed.
“Oh,” He bit his lip and closed the laptop, holding it out to her. “I got the file, I emailed it to you and backed up a copy.”
Ayesha grinned broadly then, this evening had been flawless, “Well if that isn’t the second best news I've heard all day.”
*****
Diary Excerpt Three:
“Alex has really opened up with me the last few weeks since our first fateful date. He was so cute, so shy and reserved, looking around the restaurant the entire evening like a meerkat as if we would be discovered at any moment. A few more dates and many more encounters in and out of work and he has almost become my shadow, sticking by my side all through the day at work and dwelling in my arms all night. I’d have thought he’d get sick of me, of my attitude and by the lack of anything physical outside of cuddling but he only seems more and more attached to me with each passing day. I know the lack of sex bothers him. He has been very open and honest about his desires and fantasies, going so far as to talk about strap-ons and his willingness to please me as best he can, but I keep putting it off. He doesn’t even know the truth about me yet, something I’ve really struggled to hide. I want to do so much with him, but before I can let him realise what I really am, I have to help him realise what he really is.”
*****
As he often did Alex sat curled up on the lush expensive sofa of Ayesha’s home, his head resting on the fullness of her chest as he cuddled her, one arm draped across her stomach, enjoying the softness of her form under him as she caressed him through his clothes with an idle hand, the two of them enjoying a show on Netflix having just finished between them a delicious meal Alex had prepared in Ayesha’s now spotless home.
She had been incredibly anxious the first time he had come over, worried that he would be put off with how she had lived, with little piles of messes, dishes always to be done, a seemingly constant stream of takeaway boxes passing through the door, but he had just settled in naturally, her home having transformed from the bachelor pad she had assumed his would’ve looked like to the spotless and well-presented home he had expected of her.
“You know..” she said softly, giving him a light squeeze, “I’ve been thinking..”
“Uh oh..” he smirked a little, leaning up and kissing her on the lips, soft and gentle, loving. “Should I be worried?”
She kissed him back, enjoying the brief intimate moment as she grinned, “Oh haha.. Seriously though, I have, about us.”
“Mm?”
“Have you noticed yourself changing these last few weeks?” she asked, curious.
“No?” he tilted his head.
“Just the way you act, the way you behave.”
He shook his head, obviously oblivious.
“When it’s just you and me, especially at home, you’ve been acting.. Well.. Like a girl. More softly spoken, more giggles, more sway in your step.”
He shrugged a little, looking up at her. “When it’s just me and you and I can be more.. Me.”
“So when we’re at work, who are you?”
He shrugged again, looking away, “Who I need to be to not get funny looks, I suppose.”
She bit her lip and tilted his head to look at her again, “I don’t like that. I want you to be who you are, all the time.”
He shook his head, looking a little resigned. “I can’t, you know that. People at work would judge me, my friends would leave me if I… Did that.”
“If your friends left you for being who you actually are, then they weren’t really your friends were they? And don't worry about the work people. I can see to that.”
“I mean.. But I still couldn’t.” he sighed.
“Why?”
He didn’t answer.
“Be my girlfriend, Alex. Forget what I want, you know it’s what you want.”
He still didn’t answer, his gaze distant.
“What's wrong?..” she asked gently, her hand caressing him reassuringly, biting her full lip as she noticed a tear on his face.
“You know I want to... But I just can't...” He said, voice tiny, “I can’t just take that first step, I’ve been trying all my life.. But..” he shook his head, tears falling to his shirt as he tried to control himself, “But every time I think I can, I get too scared, I back off, I just.. Just push it back deep down inside of me.” he said, releasing a shaky sigh, feeling the tears fall down his cheeks as he spoke, “I can’t live my life as a woman…”
“Don’t push it down anymore Alex. Don’t you see how much happier you are when you’re not pretending to be someone you aren’t? Just, be who you want to be. Isn’t it that easy?” She said, voice soft.
He sniffed some, using the back of his hand to wipe at his reddened eyes, letting out a despairing little laugh. “That's easy for you to say, being normal..”
She bit her lip a little. She could’ve revealed herself now, used her tool as a tool to sway his judgement, but she wanted him to take this step for himself, not for her.
“Alex.. You’ve done so much for me, so, so much. You’ve made me realise there's a life outside of work worth living, and I want to live that with you. The real you. The giggly, hip-swaying doting girl you know you really are…” she explained, looking down at him with a warm gaze.
He looked up at her, the conflict obvious, his voice shaky and broken, “I.. I’m scared to, Ayesha.”
She smiled and gave him a soft squeeze, her arm around him now, holding him to her curvy form. “I know you are.. But I promise, swear even, that I’ll be here for you. I’ll help you every step of the way, you can become who you really are and you can do it as my girlfriend.” she bit her lip, feeling her own heart strings pulling a little, “Let me spend my life with you, Alexis.”
He swallowed some and remained silent for several long, tense moments, looking up into her dark eyes, searchingly.
Finally, he looked down, his cheeks blushing gently and he shook his head.
Ayesha felt her heart sink, he mustn't be ready yet, she thought.
“Not Alexis... Alexa.. I think it’s prettier.. Suits me a little better, don't… Don't you think?” he said, softly.
She felt her heart skip a beat and her expression warmed significantly, her arms tightening around him.
“I love it.. And I love you, Alexa.”
Alexa blushed brightly and pressed his face to Ayesha’s bust, holding her tight and squeezing as she hugged him tightly. “I love you too.”
Ayesha smiled and held him close, caressing his hair lightly, holding him comfortingly to her body. “So what do you want to do first?..” Ayesha asked, querying.
“I.. I don't know where I should start. Could… Could you show me?” He asked, looking up.
Ayesha pursed her lips some as she thought, “Mm… Short term? Tomorrow we’ll get you a makeover.. New wardrobe, new hairstyle, makeup, shoes..” she grinned, excitement growing, “Long term, hormones.. We’ll talk about that soon enough.”
Alexa nodded softly, smiling some, while the worry of the changes to come was still written across his face, Ayesha knew with her by his side, he would be committed to the path that now lay before him.
*****
Diary Except Four:
“His first makeover couldn’t have gone any better, I think. Not only did it make him look simply stunning, but it gave him his first day out in the world as Alexa. I gave him the day off of work and had him picked up by an image consultant I had worked with early in my career whom I had stayed in contact with. I consider her to be a close and personal friend and I knew she would be the one to help Alexa remove the cracked mask of masculinity he was so used to wearing. I knew that by the time I returned home that evening from work the real Alexa would be waiting for me and I knew he would be anxious. I assumed it would be a difficult moment, that he would be flighty, afraid even and looking for excuses to backtrack, how wrong I was. I had wanted to show him that embracing who he was would be rewarded, and I knew how to reward him, with a gift he didn’t know I could give. While he didn’t need that persuading, it hadn’t stopped me from sharing.”
*****
Ayesha bit her lip as she fumbled with the keys in the lock of her door, she had had a difficult day at work without her PA on hand, evidence of her absolute reliance on her beloved partner, but it had been made all the worse by the impatience permeating her every thought.
She knew that when she got home Alexa would be there for her for the first time. She had received texts throughout the day from her friend, reporting on his progress, asking Ayesha to text Alexa little snippets of encouragement whenever the consultant felt it was needed.
Ayesha took a deep breath and pushed open the door to her home, stepping inside and looking around. She was met with a light but pleasant air of perfume that floated through her apartment, a new scent she didn’t recognise but that instantly got her attention.
While the absence of sex between the two of them had been the only point of tension in an otherwise perfect relationship, If the last message she had received from her friend was anything to go off of, ‘So perfect’, all that would change tonight.
“Alexa? Love?” she asked as she looked around her home, feeling butterflies in her stomach at the expectation, despite asking her friend a few times throughout the day for pictures displaying Alexa’s transformation as it happened, none had been forthcoming, her friend believing it would be best if she just saw the end result in person.
“Um.. Hi..”
Ayesha turned towards the bedroom, her eyes going wide as her heart skipped a beat, standing in the doorway before her was an image of her dreams given form, the person she had grown to love combined with the look of the women of her fantasies.
Standing in the doorway, a little anxious as he leaned against the frame stood Alexa, her Alexa, but like she had never seen him before, a true trap.
Ayesha had expected her friend to have accentuated Alexa’s femininity with clothing, but he wore only a simple pale pink silken negligee, it served to make him look smaller and weaker than he was, more vulnerable. The fragile look certainly did the trick, seeming to make him look all the softer and more girlish.
The major changes were elsewhere, he had the most flawless and complimentary makeup on that Ayesha had ever seen, drawing attention away from the more masculine edges the shape of his face had to offer and towards his more womanly aspects. His lips, for example, were a bright, ruby red, a gorgeous shade that stood out on his otherwise light skin.
His hair too had been lengthened, it was still the lovely light blonde that Aye loved and she couldn’t tell whether it was a wig or extensions, but either way, it was simply divine, shoulder length and full of bounce, framing his face and falling about his cheeks in an attractive way.
The most noticeable change, however, was Alexa’s demeanour. Despite his anxiety and fears, everything about her body language screamed femininity. His stance showing off his hips, one arm up against the door, an expression of desire across his features, where Ayesha had expected Alexa to have spent the day clothes shopping it seemed he had spent most of it being tutored on the art of being a woman.
Ayesha swallowed, staring thoughtlessly for a few long moments and knew tonight would be the first night of their true future together. This was the person she loved and by the end of the night they would both know who they really were underneath all the pretending.
Alexa must’ve recognised something in Ayesha’s expression, some hint that things had changed, he had never been pushy towards Ayesha, but he knew everything was different now.
He tilted his head and smirked a little, playful even as he blushed, “..Wanna fuck?..”
Ayesha blinked and nodded, stepping forward towards Alexa and circling her hands around the smaller boys body, tracing her fingertips across the warm silk of his lingerie as she leaned into kiss him, warm and passionate, their bodies pressing together as Alexa felt the taller woman's breasts and curves, warm full and enticing against him.
“Come on..” Ayesha said, taking Alexa by the hand. “You’ve shown me you.. It’s time I show you the real me..”
Alexa bit his lip, heart racing as he was pulled into the bedroom alongside Ayesha, looking up at her with a curious expression.
“The real you?..” Alexa asked, tentative.
“Mmhm..”
Ayesha smirked some as they stood before the base of her bed, her back to it and Alexa before her. “Undress me..” she said, simply.
Alexa bit his lip but nodded, excited and curious as he stepped forward, helping Ayesha shrug her jacket off and began to unbutton her white shirt, revealing more and more of the woman's dark skin, her full breasts pressed together and up by her half cup bra, the softness of her orbs spilling out over the top as they were freed from the shirt.
Ayesha smirked as Alexa helped her off with her shirt and got to work on the front of her pants, already Ayesha could feel her own arousal. Something she had spent so long denying and forcing back, to hide the truth from Alexa, would finally be not only set free but, she was sure, sated, at last.
Alexa’s brow furrowed as she worked on the belt, hook and zip of Ayesha’s work pants, feeling the bulge and clearly, judging by his expression, not figuring it out, as his hands worked, however, Ayesha knew he would discover the truth soon enough.
In anticipation of this very moment, before leaving the office, she had made her way to the bathrooms and removed her underwear, going commando. It wasn’t as comfortable, but it would, Ayesha knew, make for a more dramatic reveal.
Alexa bit his lip as he finally finished fighting the buttons, looking up at Ayesha with a questioning expression as he tugged the pants down eager and curious.
Everything Alexa had been waiting for was instantly rewarded as the thick, dark shaft all but sprang free of its confines, already hard, it all but fell into his hand causing him to gasp in surprise as the warmth hit him.
He instinctively closed his hand around the thick shaft but took a half step back just from the shock of it, his mouth agape as he stared down at her free member, in all its glory.
“O-oh my god.. You.. You have a..” He breathed, hardly able to believe it, unable to piece the full implications together in his mind.
“Didn’t I tell you we were perfect for each other?” She smirked slightly, taking a half step forward and reaching down, placing her hand on his, urging it back and forwards as she let her pants fall to the floor, making him stroke her hard cock, letting him feel and explore it.
“Your first one?” she asked, though she suspected from his expression she knew the answer.
He nodded, confirming her suspicions as he was quick to follow her physical instructions, his hand moving up and down her cock, stroking her steely length, eyes wide with wonder as he felt her, explored her.
“Kneel..” Ayesha said after a few moments had passed, biting her lip as she watched him, without hesitation, sink to his knees in an almost dreamlike trance, his eyes fixated on her length.
She released his hand, moving her hands to gently work over the soft curves of her own body, enjoying the sensation of being free from from the confines of her work clothes and further enjoying the knowledge that before her knelt the person she loved, who, at her reveal, wasn’t in the least put off. If anything, she knew, this only served to drive and multiply Alexa’s interests in her.
Alexa had never been shy about his fantasies and desires, there hadn’t been much point in that given that Ayesha had seen a thick dildo stuck to his shower wall the first time she had shown a returned interest in him. So Ayesha knew with a certainty that the reveal that she had a cock would be a massive boon for the two of them, the assumed barrier of sexual incompatibility he held melting between them in an instant.
Part of Ayesha wished, as she watched Alexa stroke and feel her cock, small delicate fingers tracing over her skin, feeling the texture, the warmth, the reality of it, that she had done this that first night, but that would’ve been too soon, it would’ve made, then Alex, just another victim of her prevailing arousal. By waiting she hadn’t just secured herself a gorgeous, long-term fucktoy, but a lover.
“What do you want me to do?..” He asked, blushing as he looked up at her, his uncertainty simply adorable as she caressed his hair.
“Take a wild guess sweetheart.” she said, a teasing edge to her tone as she smirked, caressing him.
He blushed and nodded understanding, from his position it couldn’t really have been made more obvious for him.
He leaned forward and raised her cock with one hand, leaning down under the hefty shaft to kiss at her dark, smooth balls, letting his tongue wash out from between red lips to glide over the cum-filled orbs.
They both moaned in unison at the action, her head tilting back at the pleasure of finally having him go to work on her, him at the lewdness of what he was doing, his tongue exploring every inch of her soon to be glistening nutsack, lifting each of the heavy orbs on his tongue, as if weighing them before kissing them, leaving red little lipstick marks on her ebony skin.
Slowly he began to kiss up her shaft, though one hand still tenderly caressed her balls, the boy had skills, he doubtless had enough practice on toys and she was curious to see how well that would translate into playing with the real thing.
As his tongue slid up under the sensitive head of her cock, his lips parting and her engorged tip sinking into the hot, wet heat of his mouth she bit her full lip. It translated well.
He closed his eyes and focused solely on the actions at hand, his mind a white haze of lust and desire as he set about sating so many of his own fantasies and wants, even as his own throbbing shaft went ignored, as he knew going forward, it often would. Their dynamic, after all, was not about the pleasure of his cock, but the pleasure of hers, and how he could fulfil its needs.
He started to bob his head on her cock, sucking as he moved, his full, lush and vibrant lips travelling along the increasingly wet length of her ebony shaft as he, for the first of many times to come, began to worship her length with his mouth, giving her his first blowjob.
“My god Alexa.. That feels so good.. You have no idea how long I waited for this..” she purred, biting her lip as she looked down over the full swell of her breasts and the curve of her body to watch as he went down on her, his hands resting in his lap, his little negligee tenting visibly, though he was so focused on her own cock she noticed he didn’t even seem to care that his own was neglected.
He looked up at her as he wrapped one hand around the base of her cock, stroking her off into his warm wet mouth, the tip of her cock help between his lips, doting on it with his eager tongue as he met her gaze. He wanted to impress her, wanted to help her realise just how good he would be to her in the coming days, months and he hoped, years.
He braced himself and took a deep breath, moving his hands across the smooth skin of her soft thighs to grope and squeeze at her thick, rear, enjoying the feeling of the doughy cheeks between his fingertips.
He leaned forward and pulled on her, feeling the hot, hard length of her cock completely fill his mouth and slide across his tongue, his lips stretching around her girth, but he refused to stop there.
Ayesha let out a gasp as she watched, in one long, slow movement he took her cock into his throat, she watched as his lips pressed down to the very base of her veiny shaft, hilting her hard member inside him entirely.
She couldn’t help but move her hands to grip his head, grinding her hips forward, feeling his face press into the softness of her curvy body and her heavy balls pressing into his chin as she felt his tongue, even depressed as it was by her thick pole filling him, lick out between his lips to probe at her balls.
She held him there, grinding into his face for a few long moments, lost in the pleasure of his actions until his squeezing hands, groping and fondling her thick ass began to pat against her, a universal sign that he was running low on precious air.
“You can’t breathe dick?..” she said, her voice heavy with amusement and lust as she held him for a few moments longer before releasing his head.
He leaned back and gasped, the gleaming cock popping free from his plush lips as he panted hard, recapturing his breath and giving her a naughty grin, triumphantly seeing a ring of red lipstick around the base of her cock, “A-ah.. I could.. Show you a trick.. Or two..” he panted softly.
She smirked playfully and helped him to his feet, capturing him in a hot, needy embrace, their bodies pressing together, her cock rubbing against his thigh as she caught him up in a kiss, her tongue delving into his mouth, tasting herself on him, but not caring.
They shared a deep, passionate kiss, his hands caressing over the thickness of her dark body as they made out, tongues dancing in unison before she broke the kiss, smirking playfully too.
“Mm.. I’m sure you could.. But with such a skillfully lubed cock like this is would be impolite not to make love to you..” She winked then turned, pulling him towards and past her, laying him gently down on the bed as she stood at the edge, hands moving around behind her to unhook her bra, tossing it aside.
Alexa bit his lip and swallowed, eying the full heavy breasts of his love with desire as they spilled free of the bra, each heavy orb proud and full on her chest, tipped by a darker, hard nipple. As he stared he scooted up the bed, giving her room to join him.
She didn’t need more invitation than that. Kicking the rest of her clothes free of her body she crawled forward onto the bed, her full breasts gliding up over the skin of his stomach as she moved over on top of him, his legs spreading for her.
She caught him in another kiss, one hand supporting her, holding herself up as the other gripped the base of her lipstick stained and spit coated cock, feeding it between his pale white cheeks, seeking her target.
Ayesha was keen and knew he wouldn’t need any prepping, given the toys he usually took, while he technically was a virgin, her size wouldn’t be a new barrier for them to face.
He moaned into the kiss as he felt the thick mushroom tip bump up against his star. He expected her to go slow, but the urgency and lust dominating her mind had given her other plans.
She leaned forward, resting more of her weight onto him as her cock spread his star, her slick length starting to fill him as his moans intensified, his back arching and his hands gripping the sheets of the bed as the pleasure filled him.
She broke the kiss, both their lips parted as they panted, each lost in the new sensations dominating their little worlds, Ayesha lost in the sensations of the beautiful deviant beneath her, accepting, and becoming with each passing day more and more her perfect woman, Alexa of the dominant, controlling and perfect Ayesha, his boss, his lover, his savior from the lie he had been living. It was so perfect for them both.
It might not have been new for Alexa, to have a thick shaft sliding deep into his little love hole, but having a dildo press into him was an entirely different, and an entirely inferior experience to having a real cock, attached to a real person fill him.
Ayesha spared no quarter as she urged her hips forward, not slowing her conquest until every last inch of her hungering shaft was buried to the hilt inside the squirming Alexa, their eyes meeting as they joined for the first time.
She held herself deep inside him, remaining still for a few long moments, experiencing the sensations of his body wrapped around her thick dark cock, squeezing and milking her with its tight heat.
Alexa, however, squirmed desperately, his heart hammering in her chest as he looked up at her, eyes half lidded, face flushed, his long blonde hair splayed across her pillows, his voice coming out soft but desperate, impatient, “P-please, fuck me?”
She panted softly, his words all the encouragement she needed. She bit her lip and moved to kneel between his legs, a dark hand on each of his soft milky thighs, gripping them as she looked down at him, still in his beautiful negligee, his own smaller cock hard against his stomach as she adjusted herself, starting to move herself forward and backward, gliding her huge shaft in and out of his boy-pussy.
“A-ah, ah, ah!” he started to gasp, the sensations not merely limited to his ass as had been with his dildos but to his whole body which bounced with each thrust, his whole world shaking as she started to fuck him.
She looked down at him, his expression one of unmistakable pleasure as she slammed her cock into him, again and again, her own full breasts bouncing and jiggling enticingly with each movement of her body.
They coupled together, their thoughts and concerns, anxieties and fantasies melting away as all rational thought deserted them, their actions being reduced solely to base instincts, each passing moment making their physicality more heated and frantic.
In a sudden shift she took his legs, pulling them up and over her shoulders, relying on his flexibility as she leaned forward, her heavy breasts grazing against his chest as her hands gripped his wrists, serving to both support her and pin him as she settled into a fast and frantic pace, the length of her ebony cock powering into and out of his ass as she fucked him, her full balls slapping time and time again into his raised ass as pleasure coursed through her body, beginning to rise and overwhelm her.
She wanted the experience to last, but it had been so long and the build up to great, no matter how much she wanted to hold back and make their first experience longer, she knew there would be many, many more such opportunities to come.
They stared into each other's eyes as her breath began to noticeably quicken, her thrusts becoming shorter, sharper and more desperate.
“A-alexa..” she gasped, her voice betraying just how close she was.
“P-please!” he begged between feminine gasps, not needing to expand, they both knew what he wanted, it was what they both wanted.
She grunted, beads of sweat forming on her skin as she hilted herself, grinding herself balls deep inside her lover's sweet ass as her cock throbbed and pulsed, the pleasure peaking and pushing her to the first of many orgasms with her darling Alexa.
They both gasped, lips locking in a hot and messy kiss as her cock pulsed, sending rope after rope of hot, sticky seed deep into his body.
He moaned into the kiss, feeling the sensations of a cock climax inside of him for the first time, Ayesha marking him as her own, and him knowing it was true. He took her cock and cum with glee, feeling for the first time in his life that he truly belonged.
She was the only person in the world for him, she would make him who he was destined to be, make Alexa into a reality. He would service and love her, take care of her as she would take care of him. Together, in their moment of shared ecstasy, they knew they completed one another.
She let his legs once more fall to the bed beside her so she could better lay on him, resting her soft body atop his as they kissed, her cock still pulsing inside of him, depositing every last drop of seed she had to offer.
Even as they reluctantly broke the kiss they didn’t speak, they didn’t need words, it had been perfect for them both and as Ayesha’s cock began to soften, their hands lovingly caressing one another she knew this was the beginning of the rest of their lives.
*****
Diary Except: Five
“It had been several months since my last entry and things couldn’t have been more different, or better. Alexa, my love had almost completed her transition, she still worked as my PA and, to mixed reactions from HR, was open about our ongoing relationship. While I still got involved in office scandals, it was no longer a case of HR receiving complaints of my sexual harassment, but more often than not, noise complaints coming from my office. I really should’ve invested sooner in a gag for Alexa, she was and is a very vocal lover, just because we were at work seldom meant we could keep our hands off one another. Even after all those months had passed our relationship was nothing short of absolute perfection.
*****
“You working on a report?” Came a soft feminine voice from the doorway and Ayesha looked up, smiling.
In the doorway stood her lover, her partner, her girlfriend. Alexa. Pale skinned, her long natural blonde hair was loose and curled, her makeup, as always, modest and on point, a soft smile on her girlish features as she stood clasping a clipboard in her delicate hands to her very real C-cup breasts, her perfect nails painted a beautiful red, her body more slender, but more showing at the hips.
“Sort of..” Ayesha admitted, looking at her latest diary entry, “I’m just writing some stuff down, for posterity sake, you know?”
Alexa nodded, clearly only half listening as she shut the door to the office behind her and casually clicked the lock shut, her high heels making a similar clicking as she walked over towards Ayesha, smirking a full lipped smile as she put her clipboard on the desk, her thumbs hooking up under her mini skirt to work a pair of black lace panties down her thighs, letting them drop to the floor, she eyed Ayesha with a smirk.
Ayesha bit her own lip and felt a very familiar swelling in pants. “Subtle as ever, love..”
Alexa smirked and unbuttoned the top few buttons on her shirt, letting her pale cleavage go on show for Ayesha, slowly moving to step around the desk, casually swinging a leg over Ayesha to straddle her, arms lacing gently around her lover's neck. “I know what you need before you do..” she replied, a sultry tone to her voice.
Ayesha grinned playfully, knowing Alexa was right, as always. “Well.. We best get to work then, hm? Time is money after all..”