First Opportunities Ch. 01

(This is a slow burner. Actual action in the next chapters.)

It started like any other evening - catching up with a close group of 3-4 friends and their +1s at Mark's place. Like we did at one of our places every month.

Mark and I (George) had been the best of friends for over a decade then, since working under a cruel boss together. Mark was over 6 foot 3, somewhat fit, and a very kind man - married to Victoria, an amazing, equally kind woman who looked so insanely good that I've wondered why she wasn't into acting, movies and all that - dark, flowing hair, 5 foot 6, a smile that lights up a room, and the very definition of feminine elegance. They met each other at the aforementioned job, and I watched that story unfold in real time.

I, on the other hand, was a thin 5 foot 7 'pretty boy', as the women categorised me, and single at nearly 30 for primarily two reasons. One was that my social anxiety levels were much higher than normal, with me watching golden opportunities with great women pass by, while I stood frozen to my spot. I also didn't make good first (or second) impressions, and the anxiety allowed my non-weird self to come out only after I knew someone for a bit. The second, bigger reason was that I was confused about my sexuality. I grew up like any other future trans kid, trying on women's clothes when no one looked, imagined myself more to be the woman in certain situations, and having the traits of a woman mentally (including the stereotypes!) while looking and acting the guy with everyone in my life. I did have some sneakily ordered women's clothing, though, hidden behind a lock in my wardrobe that I indulged in the privacy of my home now and then. My family, or even the country I lived in, or its people, weren't the most welcoming about deviations from what they considered 'normal'. Even Mark and Vicky, religious as they were, had expressed that they were uncomfortable with trans individuals.

Thus, there I was, not ready to commit to a woman, because I wasn't sure who I was to begin with, attracted to most women and some men (Mark included) historically.

Back to the evening. It was the usual board game, food, and responsible amounts of drinking kind of evening. Victoria and I were the last two players still alive on the game board - as was the case on most game days. We had decided to see it through that day, competitive as we both were, while the others ate around us. Only when the other two couples decided to head out did we realise that the two of us didn't even drink or eat.

"More stormy than rainy out there," Mark called out to the lot of us, coming in from the balcony. The others lived nearby and thought they should head home before it got any worse. "Why don't you stick around tonight, G?" he asked me. "Finish this ongoing verbal battle you two have had over months now? Take one of the guest rooms."

Unlike the reasonably well off couple, I was still at the job they had left a few years back, working for the same boss. "Nah, can't really go into work tomorrow like this. I'll head out."

"But you haven't eaten," Vicky asked.

"Will figure it out."

My car had gone, like, less than a mile in the hard rain before something gave out. I never got cars much, and called my mechanic - who was in another corner of the city, closer to my place. Tried and failed to get it going using his instructions, only managing to get drenched in the process. Called Mark, and he brought his car out to check - as my knight in shining armour usually did for most issues I got into over the last decade. The rain had intensified while he looked at it, so he suggested leaving the car there for a bit. After I turned down his request of dropping me to my house which was one hour away (or more, in the rain), we decided to see if the rain would let up while we went back & ate.

Victoria looked at the two drenched guys at her doorstep, and went "ugh, guys" and threw towels at us.

Vicky convinced me to spend the night in a guest room, and take a cab really early in the morning, while she would get her mechanic to look at the car the next day. Mark entered the once he was semi dry, and headed to his room, laughing and asking if I'd like to borrow his clothes. I'd done so once before in a pinch, and there were photos of me in clothes several sizes bigger, held only by a belt.

"No, Mark. No new size related trauma for me to process in the future, thanks."

"You're not tiny, G. I'm just big." He smirked. "Better than the alternative option for clothing in this house," he pointed at Victoria.

I was stunned by the possibilities for a second - I'd both been attracted to & been jealous of Vicky over the years. My mind went into a quick list of all the wonderful clothes I'd seen on her over the years I'd known her before I went "Oh shut up."

Victoria, on the other hand, seemed to like the idea. "Why not, actually? I have regular tshirts and we are a similar size."

Mark guffawed. I went, "Aaand thanks for that comment, Vicky. I'll never hear the end of this for a year from that brute."

"Oh ignore him. I mean it! Get out of those wet clothes, please. You're a bit more...", she paused for a second, "...slender than I am." She raised an eyebrow slowly in that oh so attractive way like she does when she's too deep in thought during our games. "I should definitely have something, come on."

"Oh I can't wait," Mark laughed.

She threw another towel at him, and dragged me to her room. Every part of me wanted nothing but to walk with her. And I did, mumbling some joke or the other to record my very weak protest. It was logical to be okay with her suggestion, I assumed, even if I didn't swing that way. I just hoped I wasn't giving in 'too easily' with those registered protests like 'everything you wear is super feminine, Vicky.'

Because they were better off financially than the average household, Mark and Vicky had their own bedrooms, instead of sharing one, in addition to the couple of guest bedrooms. In the past few years I had visited them, I had never entered Vicky's bedroom. Maroon coloured walls, the smell of flowers and the beautifully feminine decor overall was all great - a bit too much to my liking actually, but I'd never had any logical reasons to be there before.

She threw one of her wardrobe shelves open. "Get into the bathroom, dry yourself completely - here's a better towel - mine! - and get back here. I'll find something by then." I reluctantly took my eyes off the colours in her wardrobe and walked into the bathroom, while hearing a faint 'this will be hilarious' from Mark outside. In the bathroom, I got out of my clothes and dried myself in the new lush soft towel, and looked at myself in the full length mirror. I'd shaved that day, so there was little facial hair. I'd shaved my legs and arms a while back, so there was only a hint of hair there as well. Because I got drenched in the rain, the usual 'sticking out in different directions' overgrown hair on my head had settled down and was nearly reaching my jaw. That was good, I thought. The hint of fat on my chest (we are in denial about the hint of my tummy fat here) that I imagined to be breasts when I dressed up looked as disappointing as ever. The reps I had added to my workout from a women's exercise set didn't seem to help beyond a tiny bit. I sighed, knowing it was all useless anyway. I could never go and ask for Vicky's better dresses, could I? I put my clothes in the dryer, and went out with the towel around my waist. "Wow, you have nice legs, George!" Vicky's eyes had the glee of those of a kid who had figured something out, as she pointed at a set of items she'd laid out on her bed.

"Take your pick. I've a ton of tees, but for the other half, I only have black pajamas, yoga pants, slightly shorter shorts, and these roomy grey palazzos that could work for you." She paused, seeing the disappointment on my face. She probably mistook my reaction to mean that the items were too feminine, instead of the actual reaction that they weren't fem enough. "Oh please, these aren't that feminine," she added. "Except maybe the short pants."

'Can't pick those shorts anymore without raising her suspicion', I thought as I pretended to be interested in and ask about what is less feminine for a minute. Pretended that the tiny flowers on the black pajama's right knee were too much, and settled on the grey yoga pant. "It should be normal on me given I am thinner."

"Oh don't think too much. It's just for sleeping in. Just wear the PJs like a normal person." She also threw a couple of t-shirts on the bed. "These are plain & dull enough for guys."

"Um, Vicky. Is it okay to go commando in your PJs? My boxers are in the dryer as well." I hoped to get a view into her innerwear collection at the back of my head.

"Eh," she ignored the issue. "Those are going in the wash anyway. It's not like I'm going to reuse it immediately." She laughed and turned to walk out. "See you out there."

The thought of sharing clothes with Vicky was too exciting for me, and I was worried that it would...show. Even though she looked like a goddess and I was just a guy in a dress, the idea made me feel more attractive for some reason. And more woman.

This was going to be an interesting night.

(Share your first opportunities to dress as a woman in the comments?)