Work Diaries

"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.