Fateful Kiss Pt. 02

I left the office in a daze. Over the week, my anxiety had progressively waned, and had now been entirely replaced by euphoria. I was going on a date with Allison!

With newfound confidence, I walked to my car and drove home. At this point, I could obviously have changed to masculine attire, but I did not want to. Quite the opposite, I was enraptured with softness of the satin on my skin and the deliciously feminine appearance of my image in the mirror. I knew at that moment that women's clothes would become a long-term fixture of my wardrobe, but not to what degree or in what form. I had instantly decided to wear the dress Allison gave me tomorrow, but what next? The answer could wait, tonight I was merely going to enjoy both these delightful clothes and the anticipation of tomorrow's date.

Waking up on Saturday, I showered, freshly shaved my legs and immediately put on my new underwear. I now understood the lure of pure silk: the polyester satin had felt very nice but these were on a whole new level of delectation, gently caressing my skin with every move. I then tried my dress, in case it didn't fit and I needed to come up with a different outfit. A worry quickly dismissed: the dress fit me perfectly. I donned my high heels, walked to my full-length mirror and was stunned by my own reflection. The person in the mirror was ostensibly me, she (for the image was undeniably a "she") had my head, but I could not recognise my body on her. The dress accentuated the relative slenderness of my waist and emphasised my hips. The bra created the illusion of small to medium breasts on my chest. I'd estimate them to medium B cups. Finally, as I'd already noticed yesterday, the heels made my legs look sharper and my feet daintier. I spent a few minutes indulging my freshly-awakened inner Narcissus before resolving to change for now. Can't risk creasing my dress before tonight.

I gave no thought to male clothing, nor even the women's slacks I'd worn Monday and Tuesday, I knew I'd be wearing a skirt. I quickly settled on an outfit composed of my satin skirt, combined with the white blouse from Wednesday and the assorted ballet flats. A hint of my pink bra shone through my blouse, but it did not matter, as I'd be staying home until the evening.

After lunch, I spent much of my time practicing feminine mannerisms. Some, I had picked up unconsciously. For instance, even on Wednesday, I had already adopted the habit of smoothing the back of my skirt as I sat down. In other ways, though, much of my mannerisms were still very masculine. Of course, with no makeup and no real way to feminise my haircut, I'd still look like the man in a dress that I was, but I still felt it important to try to act as feminine as I could learn to in a few hours.

The appointed hour approached and I gleefully changed into my dress. Within the span of a week, I had gone from reluctantly donning women's trousers and a woman's shirt in my own home to happily wearing a dress in public. At this point, the thought was more amusing than anything. I had been leashed by my inhibitions and the codes of society, keeping me from wearing the clothes I enjoyed. Although at the time, I did not know I'd enjoy them.

We met in front of the restaurant, as arranged. As pretty as Allison was in office clothes and minimal makeup, nothing could have prepared me for the enthralling vision of her in a cocktail dress and full makeup. Her knee-length dress was purple, with an A-line matte satin 2-layered skirt and an off-the-shoulder bodice embroidered with lace and gemstones. The dress presented with a cincher belt, accentuating her tiny waist. Allison's neck was adorned with a string of subdued, small green gems. She wore matching rings and earrings. Above her eyes, a shadow with a gradient from pink to deep purple, her lips the perfect shade of pink. To complete the outfit, her dainty feet were encased in purple stilettos. She radiated elegance and poise with every gesture.

For a brief moment, I had been left speechless, giving her the opportunity to speak first: "you look lovely."

"Thank you. You are nothing short of stunning. Literally. Your beauty momentarily deprived me of the ability to think or speak. Aphrodite herself would be jealous." I knew it sounded corny, but I meant every word.

"You exaggerate."

"I do not. At this moment, you are the most beautiful woman I've ever seen. And I'm including celebrities!" Again, I had blurted out an unfiltered thought, realising too late how it sounded.

"Well, thanks. Here, this is for you," she replied, handing me a pink clutch purse. I grabbed it without question. She had been thoughtful, if I was going to wear a dress, I should be carrying a purse. I immediately inserted my wallet, which I'd been carrying in my hand for want of pockets, inside the purse.

"Thank you. Shall we?" I said, gesturing towards the door.

"Let's."

We entered. A lot of eyes turned to us, be it to admire Allison's beauty or gawk at the freak standing beside her. Both, probably. We gave our reservation and were led to a table.

Being in a dress in public still felt deeply surreal, but just as enjoyable. It rendered the experience of the date much more magical than if I'd been in drab male clothing.

She broached the topic of the past week and my decision to wear the dress today almost immediately after we ordered: "I'm glad you chose to wear the dress."

"Instantly knew I would when you presented it to me."

"You really seem to enjoy wearing it, and much more relaxed about what people think of you than a few days ago. I take it you'll be wearing women's clothes again in the future?"

"Definitely."

"Have you given any thought to when? Just at home? At work? On future dates with me?"

"Thrilled to hear there'll be future dates with you. I'm actually considering wearing women's clothes exclusively from now on. Every day, everywhere. In fact, I want to say goodbye to trousers, even women's trousers, and any other garment I deem insufficiently feminine."

"Wow! That's a lot more extreme than I expected. Are you sure you thought it through?"

"Well, see, I've reached that decision for three reasons. The most important one is that you apparently like seeing me like this. You've given me increasingly feminine outfits all week long for a reason, and I think it goes beyond merely teaching me a lesson."

"Hey, don't go blaming this on me, you clearly enjoy wearing them!" she interjected, playfully feigning outrage.

"Enjoy? I love wearing these clothes, and that was to be my second, somewhat less important reason."

"The third?"

"You said it yourself: I'm a lot less worried about what people will think than I used to. I've worn women's clothes around colleagues and now around complete strangers. If I can wear them around friends and family, I have no reason left to not do it every day, and I expect most members of both groups to be either supportive or indifferent."

"You'll need a whole new wardrobe quickly, then. How about we make our second date a shopping trip, tomorrow?"

"Gladly. Speaking of shopping, how did you know my size?"

"I don't follow."

"You do. It's quite obvious that the clothes I've been wearing aren't yours. I was too distracted by anxiety to realise it immediately, but they're all several sizes too big for you. You bought it all specifically for me, didn't you? You planned it all from the start, right?"

"... I did and I did, yes. I really wanted to see you in a skirt." She pouted in feigned guilt, then unleashed her heart-melting smile.

"You devious woman," I retorted, in mock outrage. In truth, I was more smitten than ever.

At this moment, the waiter arrived with our food. We devoted the meal to various subjects of conversation. We already knew each other as colleagues, of course, but rarely had talked about domains unrelated to work. Allison was as pleasant and witty a conversationalist as I'd expected.

We made plans for tomorrow, paid and, after an intense kiss goodnight, departed to our respective abodes.

I shot out of bed and showered as soon as the alarm started blaring. Allison and I had planned a long day's shopping. I quickly put on my black lingerie set.

Desirous of maximising the femininity of my outfit, I wore my satin pencil skirt and my pink blouse. I'd be walking a lot today, so I opted to wear flats. Defaulting to the most feminine option once more, I picked the ones with white bows.

A quick check for a skirt bulge: none to be seen. In a matter of days, tucking had become second nature. I grabbed my purse and was out of the door.

I drove confidently to the mall's parking lot, and walked through it no less assuredly, a far cry from my first experience wearing a skirt in public. To think that was less than a week prior!

I met Allison at the entrance. Her outfit was very similar to mine: grey satin pencil skirt, white satin blouse and white ballet flats. She was again resplendent.

We entered the first shop to bemused looks from the salesgirl. I did not hold those looks against her, a man wearing clothes like mine was an unusual sight. To her credit, she regained her composure and professionalism quickly and raised no objections when we told her the reason we were here.

Allison and the salesgirl were more experienced in picking women's clothes than I was, so I was quickly swamped in various garments to try out and ushered into a fitting room. The first item that caught my attention was a red pleated skirt that struggled to reach my knees. I swayed from left to right and took a couple of sharp turns in the fitting room, enjoying the movement of the skirt around me.

As I solicited Allison's opinion, she made me walk in the skirt in the shop, her smile telling me all I needed to hear: this was the first skirt I'd buy for myself. I purchased a couple more items from that shop: a yellow sundress with a motif of black lotuses and a pink sweater.

As we went from shop to shop, my hands began to fill with bag after bag. Eventually, my hands were full and Allison had to carry some. I'd acquired a plethora of skirts, dresses, blouses and other feminine garments: a simple black maxi skirt, a couple more short skirts, five new satin blouses (Allison knew a place, and she loves seeing me in satin as much as I love wearing it), a "little black dress", etc.

It was past noon when we decided to take a break. We carried the bags to my car, then went for a quick lunch.

We'd covered clothes in the morning, now we moved on to lingerie. First, panties. Allison selected a wide assortment for me, in various colours (shades of pink dominated, naturally) and cuts (boyshorts, knickers, briefs... even thongs!). Some had lace embellishments, some had little bows, some were plain. All had a glossy texture.

Many came with a matching bra. A few camisoles were included in the pile. "You'll understand why," she quickly remarked.

We then moved on to nightwear, which Allison insisted I try on. The first item was a chemise, pink satin of course. I entered the fitting room, removed all my clothes with the exception of my panties and put it on.

I hadn't been feeling self-conscious all day, but here, standing in front of a mirror clad in only panties and a pink satin nightie that only reached mid-thigh, the feeling was back. I loved the vision in the mirror, but still felt out of place, like I was invading a world I had no right to enter. My musings were cut short by Allison's impatient plea: "can I see?"

I opened the curtain. She gasped.

"I want to see better, come out of there." My heart rate shot up at the notion.

"I'm not walking into the shop wearing only a short nightie," I protested.

"You've done it with dresses that weren't much longer earlier today."

"It's not the same."

"How isn't it the same?"

I struggled to find a reason. Was it because I wasn't wearing a bra? I don't need one, and was quite used to not wearing them. Was it how revealing it was? She was correct about this: I'd been wearing a dress with spaghetti straps all of yesterday's evening and tried on plenty of skirts and dresses of a similar length today, rarely hesitating to take a few steps in the shop.

Of course, my misgivings were legitimate: there was an inherent difference between a garment made to be worn outside and a more intimate one, but I did not realise it at the time, or at least could not properly explain it.

One pleading look later, she had convinced me to exit the fitting room dressed as I was. I anxiously stepped out, barely. She urged me to walk towards her, then walked around me, to inspect me from every angle.

I, a man in a pink satin nightie, was now in full view of anyone in the shop. In fact, even people looking into the shop from the mall could see me. I'd never felt this naked.

Allison kept me distracted from that feeling by asking me my opinions about the fit, the cut, the length, the colour and every little detail of the chemise I was wearing, adding her own comments.

Slowly, I relaxed. Nobody had made a disparaging comment and, if there were stares or jests, I was too focused on the lingerie and my companion to notice them.

Soon enough, I was modelling various nightdresses, chemises and nightshirts for her in the shop. I drew the line at babydoll-style nighties. For those, she'd had to be content with looking into the fitting room. Eventually, she handed me a long white nightdress. "Pure silk satin," she hastily commented.

Most of the lingerie I'd worn prior had been polyester satin, save from yesterday's underwear, so I was ill-prepared for the world of bliss I had just plunged head first into.

"How is it?"

"I never want to take it off."

She opened the curtain, looked at me, snuggled against me, grabbed my arse through the nightdress, as she had done through my skirt Friday, and launched into a passionate kiss.

I had already obviously decided to buy the nightdress (despite the hefty price tag), but if it inspired such behaviour in Allison, I had all the more reason to.

Through Herculean force of will, I was eventually able to part both with Allison's lips and the nightdress' caress and changed back into my clothes.

The counter presented with bag after bag of lingerie. Allison had selected various hosiery whilst I was trying on nightwear and announced she added a few "surprises" for me to discover later.

Another bleeding of my accounts later, we were out of the shop. Time had gone quickly, it was already 3 PM. I'd just spent two hours trying and buying lingerie! Once more, Allison helped me to carry my bags to my car.

"Thank you. Shall I walk you to your car?"

"I took the bus."

"Care for a lift home?"

"Gladly."

We got into the car, she entered her address in the GPS and we were underway. We were barely out of the parking lot that Allison gently caressed my thigh and rested her delicate hand there. I pretended not to notice, but my heart was racing and my concentration on the road harder to maintain. I took a wrong turn, the GPS recalculated a slightly longer route. No harm done, as far as I was concerned, this trip could've lasted hours.

After a few minutes, her hand started sliding, ever so slowly, beneath my skirt. Soon, her fingers were lightly brushing my panties, gently caressing my penis through the silky fabric. I could not stop a moan, nor could I restrain an erection. "She likes it," said Allison with a laugh.

I was in no mind to correct her pronoun use. In fact, I leaned into it: "she loves it."

Not long ago, I'd never have believed the notion that a woman would caress me under a skirt and through a pair of panties while I drove, even less so that I would adore the feeling, and least of all that said woman would be none other than Allison!

She kept her ministrations going for the rest of the way.

Upon arrival, Allison invited me in and moments later we were in her bedroom, snogging whilst fondling each other. It was not long until we were on her bed, her below me, still locked in embrace.

I broke the kiss, and slithered lower and lower. I reached under her skirt, and pulled her panties off.

She spread her legs. I was finally looking at her in in her full glory. I plunged between those legs, eager to worship her perfect vulva. I took my time. First planting little kisses on her labia and clitoris.

Then, gently licking her opening, taking care not to enter it prematurely. Needless to say, at this stage, my erection raged as it never had, escaping the confines of my panties, furiously tenting my skirt. With the lightest of touches, my finger brushed her bell as my tongue continued to lick her honeypot. I must have been doing something right, as she moaned and reached my head to push me further in. I took that as a signal, my tongue slowly penetrating her and getting back out, just as slowly. After a moment to savour her taste, I resumed. I gradually accelerated my pace, her moans getting louder and more frequent. All my senses were in ecstasy: her pussy was beautiful and silky smooth to the touch, her juices smelled and tasted like ambrosia and my ears told me she was very much enjoying this.

I was prepared to go on until she was satisfied, but after some time she breathlessly whispered for me to penetrate her.

I stood up, dropped my panties and lifted my skirt, my penis springing free from the garment, seemingly manifesting its own desire to serve the goddess before me. Its size was decidedly average, but at that moment, it could've broken the world record of rigidity. I gingerly inserted the tip of my glans inside Allison's magnificent opening and slowly pushed more of it inside. I took a brief pause when the whole glans was in, then kept inserting my penis further in until I eventually bottomed out. Another brief pause to ensure she was fine, and I started thrusting, slowly at first. She soon encouraged me to speed up, which I immediately did. She repeated her command twice more, and I obliged both times. I could feel (and hear!) her getting closer and closer. Moments later, she erupted. Her vaginal walls clamped down on me and I soon followed her, with no time to pull out. I promptly apologised for ejaculating inside her, but she didn't mind.

Afterwards, we ordered a take away meal. I straightened my clothes and opened the door as she took a shower. I had never been this happy, and I hoped I was making Allison happy too. She came out of the shower completely naked, as she would remain the whole evening.

As we ate, she exclaimed: "you're spending the night here." Her tone brooked no argument: she had not offered, she had stated it as fact. I obviously would not have refused, anyway. She had a plan in mind for the evening: she would give me make-up lessons. She started launching into a speech (that she had seemingly honed in the shower) as to why I should be wearing make-up if I'm going to wear women's clothes from now on, but I interrupted her by enthusiastically agreeing that I should and thanking her for the offer. Before teaching me how to properly apply everything, she insisted to do it herself, facing me away from the mirror so that I wouldn't see the results until completion. Her expert fingers worked their magic, as I tried to keep my head still as her marvellous naked breasts darted in and out of my field of view with each stroke of her brushes.

When she finally put the finishing touch and allowed me to look in the mirror, I was captivated. Sure, the image was still relatively masculine and my short hair wasn't helping in that regard, but I still looked far more feminine and far prettier than I usually did. I could've passed as a somewhat masculine woman.

I spent the rest of the evening removing and re-applying make-up, under Allison's watchful guidance.

Finally, it was time to call it a night. Allison insisted I wore my long white silk nightdress, as she donned a much shorter, but no less silky, sky blue number. Once in bed, we could not keep our hands off each other, nor our lips apart, anymore.