Fateful Kiss Pt. 03

The sound of an unfamiliar alarm clock. Where was I? As the mists of sleep dissipated, my memories cleared: I was at Allison's. I shook the disbelief from my mind as I came to terms with the fact that I had slept with her, with a woman I'd been fantasising about for years. Additionally, I quickly came to the realisation that waking up in a silk nightgown feels even better than going to sleep in one. My bedmate rose up and interrupted my reveries by reminding me that we needed to get to work.

No time to enjoy our sleepwear, even less so each other. We showered together. The thought of shower sex had not escaped me, but Allison read my mind and reminded me, once again, that there was no time.

I had already planned my outfit whilst shopping yesterday, so it took little time for me to gather everything: a new pink bra and panties set, a pink blouse with black polka dots and a tight black skirt with pink lacing down the sides. All in satin, of course. Black pumps with stiletto heels, pink lining and a pink sole completed the look.

Allison was wearing a more traditional outfit: a grey pencil skirt and a plain blue satin blouse. Yet, underneath her rather conservative outfit, she was wearing the same panties and bra as me, having bought a matching set whilst I was in the fitting room. She, too, wore black pumps.

We did our makeup side by side, after which Allison helped me correct my slight mistakes.

I was about to get into my car when she told me to get in hers. It seems I was coming back to her place tonight. Arriving at work, we drew some stares. Was it because of my appearance, or the fact that we had come in together? Neither of us particularly cared either way. Let them gossip.

The morning was mostly uneventful, until I ran into Alex. He started rather openly mocking me in front of a few colleagues, seemingly having prepared material during the weekend. I did not respond. Surprisingly, I did not need to, as the rest of the group quickly turned on him, berating his unprofessional and rude behaviour. They were used to his arrogant attitude and occasional barb, but a full tirade of hatred was unusual, even for him. Several decided to bear witness of what had just happened to HR. It took a few weeks, but this incident, adding to a pile of prior complaints, would lead to his dismissal.

Allison had a lunchtime meeting, so I looked for friendly faces. Spotting a table with Anna, Mary and Olivia, I went to join them. At the very least, I knew Anna was supportive of my new clothing inclinations.

Indeed, I had barely sat that she remarked: "I love your outfit, Damian!"

Mary instantly piped up: "Yes, you have a great fashion sense. Or should I say Allison does?"

The connection between my change of clothing and Allison and I being seen with each other more often than usual had not escaped her.

"Thank you both. To answer your question, Allison did start me on the path of femininity, and she's been a wonderful guide as I walked it, from timid and reluctant steps to bolder and more enthusiastic ones, but I picked my own outfit today."

"So, are Allison and you a couple now?" she pursued, asking rather bluntly what she had just hinted at. Allison and I had decided not to keep our relationship a secret, so I could respond freely: "well, it's early days, but we have been seeing each other outside of work, to my unmitigated delight."

"She's in love!" blurted Olivia, blushing and immediately correcting herself: "sorry, he."

"Don't apologise for a compliment, Olivia," I softly reassured her. "And yes, I am. Very much so."

Eventually, the conversation moved on from my clothing and romantic relationship. Emboldened by my reaction to Olivia's mistake, the women were now casually referring to me in the feminine.

I felt a weight of pressure being lifted from my shoulders during that lunch. For once, I could just have a light conversation with colleagues without constantly worrying about everyone's perceptions, judgments and expectations. To them, it seems I had quickly become "one of the girls", and I owe them a debt of gratitude for their prompt acceptance.

The afternoon went without a hitch and Allison and I were soon back in her car. Finally, it was time to implement the mischievous plan I had been thinking of all day. It was my turn to innocently place a hand on her leg and slowly creep towards her skirt until it was in a position to strike. I slipped my hand under her skirt and started caressing her labia through her panties. She was getting aroused, her panties damper and damper. I moved them aside and gently inserted a finger in her inviting snatch. As I kept manually pleasuring her, she slowed her driving. As soon as we arrived at her place, we rushed inside, to the bedroom. She removed her panties, tossed them aside, got on the bed and I dove between her legs, frantically lapping at her genitalia with little control or thought about technique. She pushed my head down hard, as if to shove it all inside her. I did not mind. It did not take long for her to orgasm, my head still firmly locked between her thighs.

Whilst she took a moment to recover, I stood up, removed my panties and lay flat on the bed. I then invited her to straddle my face and, after admiring the view or her whole body above me, started eating her slit again. She did not remain motionless for long, rolling her hips back and forth, as if to facefuck me with her pussy. By the time she reached her second orgasm, I had long stained my skirt, without my penis ever being touched by either of us. Our clothes were now in dire need of laundry, so we changed into our nighties. Mine was the short pink one I had tried first in the shop. Hers was a purple number that plunged to reveal much of her breasts, teasing the rest of them. We had barely donned them that she lead me back to the bedroom, lay on her bed and spread her legs. I wasted no time lifting my nightie and penetrating her. Her legs clamped around me and we started making love. We were both so horny that it didn't take long until we both reached another climax. We spent the rest of the evening snuggling while watching TV. It was then that we decided to move in together. We'd only been dating for a very short time, but neither of us could conjure up a reason not to. Her place being closer to work than mine (and, quite frankly, nicer), it was selected.

On Tuesday, we therefore took both cars. After another relatively quiet day at work, I went back home for the first time since Sunday evening. There, I gathered all my male clothes and took them all to a nearby charity shop. I was committed to wearing skirts full time, and very excited about it. While there, I couldn't resist buying a couple new skirts. Buying them on my own was exhilarating.

Although I had no intention of wearing them again, I kept the androgynous clothes Allison had initially given me, as a memento of the start of my journey. I grabbed personal effects (no more swapping the heads of Allison's electric toothbrush!), the remainder of my women's clothes, save for tomorrow's outfit, and put it all in the car. Moving properly could wait, but I wanted to have all my clothes available.

I then took some time to assess my appearance in the mirror. It was a confusing blend of masculinity and femininity. Framed by my new short purple skater skirt, my legs looked decidedly pretty. My waist had always been narrow for a man, but could stand to contrast more with my hips, especially when wearing straight skirts. My chest lacked an obvious signifier of femininity, but could pass for a flat woman's. My head, on the other hand, could not look like anything but a man's. Not helping matters, my hair was so short that Allison's attempts at feminising my haircut had failed.

I could, of course, remain like this. I could keep looking like a man in a skirt, there was nothing wrong with that. What I realised, in front of that mirror, was that I did not want to. I aspired to look in that mirror and see a woman, head to toe. The rest of my evening was spent on the internet, getting informed about how to achieve that goal. Hormones. I wanted hormone replacement therapy, and I wanted it as soon as possible. I'd have to bring it up to Allison the next day to see if she approved. Sure, she'd been the one to put me in women's clothes to begin with, and she really seemed to enjoy it, but that did not necessarily mean she wanted me to feminise my body. Maybe she was content with my current appearance, hair notwithstanding.

We were barely back at her place on Wednesday evening that we adjourned to the bedroom. After full day without seeing each other, we had a lot of sex to catch up on. During a break between two rounds, I breached the issue of hormones. Allison was fully on board with the idea, and surprised me with an idea of her own: "if you're going to be a woman, you're going to need toys!"

With those words, she jumped out of bed and reached for her drawers, retrieving a long, thin dildo and some lube. I was initially reluctant, but trusted her. The notion of being penetrated was strange and uncomfortable, but arousing just the same. She asked me to remove my panties and get on all fours. I complied. She slathered the dildo in lube, then flipped my skirt over my arse.

I could feel the dildo approach then slide between my cheeks and bump my rosebud. She asked me if I really wanted to go along with this. I nodded my answer and felt a push, then an entry. It was painful, but not too much. Patiently, she waited, then pushed it a bit further. She repeated the process several times, then started pumping the dildo in and out of me. By now, I was enjoying it. My initial shame at the act was gone, and I relished the idea that Allison was fucking me with her toy, as my erect member would attest to. She kept going until I baptised the floor in semen. After that, I had no choice but to agree with her: I did need toys.

On Thursday, after work, we visited a sex shop together, intent on buying me a dildo of my own. Whilst there, Allison murmured in my ear: "you should get butt plugs, too. Wear them under your clothes. I do it, sometimes." I enthusiastically agreed and she picked plugs of various sizes for me.

I was suddenly drawn by the costume section of the store, by the shine of a satin maid outfit. It was black, hemmed in white frilly lace, with a small white satin apron. The sleeves were long, and terminated in white lace too. The skirt was short and full. It wouldn't even fully hide my panties, I estimated, at least not when I bent over. I sauntered to the aisle, to search for my size. No hesitation, I was definitely going to buy it.

Returning to the till with my new prize, I found Allison had grabbed another item in my absence: a strap-on! I blushed, since it was now evident to the saleswoman and any other potential customers that the toys were going to be used on me, but did not object. I could already imagine Allison penetrating me with her plastic cock, and the thought strained my tuck almost as much as the maid outfit had.

We were barely home that she suggested I try on the smallest plug. It was a chrome plug with a bulbous shape, stopped by a disc-shaped base. I dropped my panties then and there, fetched the lube, coated the plug in it, bent over slightly and slipped it under my skirt, aiming for my back entrance. I quickly found it and pushed the device in, eager to feel it fill my passage. The way I had confidently impaled myself on the plug had turned us both on, and moments later my penis was again lodged in Allison's vagina. It felt different than it ever had, as I was constantly distracted by the presence of my anal invader, but no less pleasurable. Inserting anything in my arse had been a taboo for me and breaking it made me feel so dirty... so horny.

Allison urged me to keep the plug in the whole evening, so I did. It was inside me as we ate and as we watched TV. I removed it for the night, and cleaned it. I anticipated Allison would suggest I'd wear it tomorrow at work, and I wanted to anyway.

Friday was an interesting work day. Feeling the plug with every move I made was arousing and the secret of wearing it doubly so, but it was also exhausting, as I kept wondering if people could tell it was in me. I could hardly focus on work. In the morning, the plug felt great, filling me and pressing on my prostate, leaving me in a constant state of arousal (thankfully, my tuck held!). By the end of the day, my arse felt sore and I wanted to take it out, but could not do so before getting home.

We spent Friday evening cuddling in front of the TV, both of us independently realising we'd spend the week-end in a sex-crazed frenzy. On Saturday, I opted to wear a cute little sky blue sundress, with pink lingerie underneath. Allison made a much simpler choice: she simply removed her nightwear and declared herself dressed. Unsurprisingly, my penis found its way to her slit more times than either of us cared to count that day. On Sunday, the roles were reversed: as I was donning my maid outfit, she decided to wear a suit, with her trousers' fly open to allow her strap-on to poke through in its full glory. I spent the day doing various chores, often being interrupted by a plastic cock bumping my anus under my skirts, that I gleefully would lift. I was consumed by the role of the submissive maid: the feel and look of the dress, as well as the subservience to my mistress of the day brought me to levels of arousal I had not experienced prior. As I went about accomplishing my tasks, my skirts flitting with every step, I never knew whether bending over would result in being impaled on Allison's artificial member or not.

Over the next few months, we initiated the process of my transition. While hormones took a frustratingly long time to obtain, laser hair removal was quickly arranged and, barely two months after I started shaving my legs, had it become obsolete. Under Allison's guidance, I became quite adept at applying my own makeup, sometimes even hers. I also chose a new name for myself: I'd henceforth be known as Julia.

Allison and I were still all over each other. Sometimes we involved toys in our lovemaking, sometimes not. We role-played as mistress and maid roughly once a month and bought other costumes, alternating dominant and submissive roles depending on the situation: she'd be the pilot and I the air hostess, but she'd incarnate the Japanese schoolgirl while I played Ms Hiddenspear, the English teacher. Needless to say, the sight of Allison in her sailor uniform ensured that spear didn't stay hidden for long.

One Thursday, we both decided to wear plugs the whole day. As horny as wearing a plug made us, it was nothing compared to the secret knowledge that the other also had one on. Being more used to toys, I could more easily bear wearing one for a whole day. From that day on, we kept doing it every Thursday, regardless of what was planned, so we ended up wearing plugs to work parties, to the theatre and even to concerts.

At work, we had both become friends with Anna, Mary and Olivia, often spending lunchtime together. Not everyone at work had accepted my change (although Alex had been shown the door, I still received abuse from the warehouse staff) but at least they accepted the new me without reservation. My family and prior friends had been surprised by the new me and things were awkward for a while but they ended up understanding and supporting me in the end.

A year later, I had jumped through all requisite hoops, and I secured an oestrogen prescription. We celebrated that day with champagne (and sex), but the next couple of months were frustrating. Of course, we both knew they didn't work instantly, but it was nevertheless discouraging to not witness results for what felt like an eternity. Until we started to gradually notice changes. At first, we were unsure. Allison would ask if my skin was softer or if she was hallucinating it or I would enquire whether my chest looked puffier, and the other would equivocate a response. Eventually, the changes started becoming undeniable. My face was definitely more feminine than it used to be and my skin much softer.

Most importantly, my bras fell less and less flat on my chest, until one day I felt comfortable calling these growths breasts. I had barely pronounced the phrase "my breasts" aloud that Allison dragged me to the bedroom to celebrate. Even though they hadn't been noticeably bigger than the previous day, she could not keep her hands (and lips!) off my breasts, and I couldn't be happier about it. Merely acknowledging that I now had modest boobs had made me aware of how sensitive they felt. After a prolonged love-making session, we brought out the tape measure: I had A-cups! The news warranted another wrestling match in the bed.

Over the months, my "girls" kept growing, reaching B-cups. Neither Allison nor I grew tired of playing with them. We both loved the feeling of each other's boobs brushing against one another. In very different ways, we were both becoming lesbians.

They kept growing. Eventually, I was catching up to my lover's perfect C-cups, allowing us to add another kink to our repertoire: occasionally wearing each other's bras from the day before. It was a simple thing, but it turned both of us on tremendously.

This was short-lived, though, as it reached a point where her bras became too constricting for me. We had to resign ourselves to the conclusion that I'd become bigger than her. We initially both felt slightly uncomfortable about that, without being able to pinpoint the exact reason why. For a time, we actively avoided involving them in bed. A few weeks later, we talked it out and realised we'd been silly, and Allison gleefully buried her face between my welcoming boobs. They'd finally cap out as D-cups. The endocrinologist told me it was unusual, but not unheard of, for trans women to get such big boobs from hormones alone, emphasising how lucky I was. Honestly, I felt they were slightly too big, but they still looked good.

At the same time, my penis was progressively losing rigidity until I could no longer sustain an erection. Good thing Allison had introduced me to toys early on. We both occasionally missed vaginal penetration, but were now experienced enough in other avenues of pleasure that the blow was not too severe.

One of the traditions we had quickly developed was to go to a nice restaurant every last Saturday of the month, to commemorate our first date. We always took great pleasure in dressing to the nines, in cocktail dresses, for those outings. It was on such an occasion that our lives would be forever altered.

I was wearing an off-the-shoulder red charmeuse dress, with a two-layered skirt reaching my knees and a bodice that permitted a glance at the top of my freshly-grown chest adornments peeking out of the sweetheart neckline. I wore matching red velvet pointed-toe stiletto heels. To compliment my bare upper chest, I had donned a silver necklace embellished with small pink stones, but had otherwise chosen to eschew jewellery, a restraint Allison had shared, only opting for a rather discreet pair of silver earrings mounted with small sapphires.

Her silk dress was a deep black, with short, slightly puffed sleeves, a square neck and an A-line skirt stopping at her mid-thighs. She, too, was wearing pointed-toe velvet pumps that matched her dress.

As usual, she was resplendent.

Partway through the meal, seemingly out of nowhere, she produced a small box and went down on one knee. A rush of emotions stirred in me, shock and surprise quickly brushed away by sheer unmitigated happiness. Blind to the eyes of the other patrons and staff that had turned towards us, I sat, mouth agape, as she opened the box and spoke the words that will forever be etched in my mind: "Julia, will you marry me?" She had barely finished her sentence that I was loudly exclaiming: "YES! Yes, Allison, of course I will marry you! The past two years have been the happiest of my life, and it's all thanks to you! All of it!" She placed the ring on my finger and rose to her feet, her lips meeting mine in embrace.