quibble1992
"
*****
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.."
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