Sweet Wednesday Ch. 02

I knew I was going to call Eva then. I'd get in touch with her and she could feminise me, tell me about her hormones she was on, maybe even slip me some so that I could have real natural breasts like her ... the thought was too good to be true! I rolled over to turn on my bedside lamp so I could see the number she had written on my arm to get in contact. But when the lamp clicked on, obviously there was nothing there. I remembered the haste I had been to get every last remnant of Sweet Wednesday off of me, including my only way of contacting Eva. It had come off completely in the wash. Oh no! A gorgeous real trans woman had for some reason taken an interest in me, offered to help me and I had wasted my chance. Stupid sissy!

It was totally gone, no last vestige of it lingered on my fair skin. Fucking hell, I thought to myself, I have well and truly fucked this. How else could I possibly get in touch with her, aside from rocking up at the club same place same time and hoping she'd be there again? But that was ages away. I really knew absolutely nothing else about her.

I had an idea and pulled open Grindr on my phone and set it to the trans filter, and restricted the age range to 25 to 35, which is what I roughly estimated Eva to be. But no sign of the Latina woman as far as I could see. While I was on the app for about five minutes, three guys sent me dick pics which I had a quick look at, nothing special apart from a toned guy from Indonesia who had a nice thick pole that I wouldn't mind sucking if I had the energy to wheel myself over the 3km to his place. But no Eva. I shut off my phone with despair. With no way of getting in touch with her, I'd have to give up my dream of being feminised by the stunning Latina I had had a chance encounter with. What a sad way to top off such a day.

I slunk out of my lingerie and added it all back into my stash. Even though my door was locked, I was usually too anxious to sleep in any of my ladies' nightwear - what if there was a fire in the middle of the night and my dad kicked down the door to save me, only to find his only son snuggled up in a lacy teddy? But tonight, I thought to hell with it, I'm going to live my sissy best life. I pulled out a black nightie I had ordered on Asos and got under the covers, going to sleep for this night at least as Amy...

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The days after my encounter at Sweet Wednesday were particularly melancholy and I think my friends and family could sense it. I was gutted that I'd embraced my sissy identity and thrown myself into my new life that I was more sure than ever now that I wanted to live, but my chance to move to the next stage of feminity, real help and support by an actual trans woman, had been scuppered. Squandered by my fleeting bout of shame in the aftermath of what I now considered to be a meaningful experience. It wasn't exactly a new feeling, sissy regret was also seemingly an essential part of the early days in a sissy's journey. The amount of times I'd spent my pay packet on some new lingerie, felt a wave of revulsion with myself after a Grindr hookup (or particularly long edging session with myself where I'd gone down some pretty fucked up and perverted rabbit holes online), and decided to chuck the whole lot away... only to desperately want it again when I was horny and trying to organise another meet up. But this time felt even more frustrating than just replacing some underwear.

I was mopey and distant with people. I wanted to be a sissy for good, and I was determined to go back to Sweet Wednesday when it was next on again, but it wasn't running for another month. And there was no guarantee that Eva would even be at the next event. I spent the next few days outside of work and college, locked in my room, panties round my neck and stuffed down my throat, watching more and more obscure sissy fetish videos. I was getting into milking, sissy pregnancy and chastity subgenres, all the time getting deeper and deeper. At night I was sleeping permanently in my teddies now, and had a new one bookmarked on my wishlist to save up for, a floaty yellow satin thing.

I was still getting offers on Grindr but one thing I had decided since meeting all the other fabulous and convincing tgirls was that I wasn't going to go on any other meetings just as a man in knickers. That had appealled to me in the past and still did in a way, not trying to pass as a trans woman but being an obvious and unconvincing panty boy definitely had an element of humiliation that I craved. But seeing how beautiful some of my fellow crossdressers at Sweet Wednesday looked after their transformations, I wanted to master make up next. I'd found a starter kit online I was going to order and had started watching some make up tutorials on YouTube. But until my next pay day, I couldn't afford it. Make up was pricey, how did women manage this?

Come the weekend though, I had to leave my sissy wank den and get back into man mode for a night out with the boys. Given my mopiness, I'd been quite quiet in the group chat and I think some of them had picked up on it. We'd had this night out planned for a while, my old school friends and some of the girls from our year. Everyone was excited and I could tell some of them were trying to encourage me to get hyped for it to get me out of my fugue. Saying how much they'd wingman me to get some chicks. At least it wasn't screamingly obvious that I actually wanted dick. Curtis hadn't messaged me though. I was sure he knew I was a crossdresser now. Maybe I should chat to him about it, I thought. Would he understand? I could tell him I was with a woman, and she'd dared me to wear it and, as a joke ... no, it wasn't believable.

On Saturday evening, as I got ready to go out, I reflected on how boring getting ready as a guy was. I knew exactly what me and all my mates would be wearing. Jeans, trainers, some aftershave and then a variety of pretty boring tshirts. Maybe some hair wax. But I could only imagine how exciting it would be getting ready with the girls we'd be meeting up with later. I knew Lewis's girlfriend Steph would be joining us. She'd surely have been getting ready hours in advance. A shower three hours before. Maybe gently stroking her clit while she got herself clean, teasing herself for the fucking she'd get from Lewis later. Stepping out, she'd begin the process of getting ready. She'd want to look good for her man of course. Wanted every other girl in there to be jealous and every guy to be drooling over her. How a sissy like myself fitted into that equation I wasn't quite sure.

She'd sit down at her vanity table, naked apart from the towel wrapped around her waist and begin cleansing her face, then moving onto applying foundation. Some girly tunes playing in the background and texts from the other girlies lighting up her phone, sharing gossip and outfit suggestions before the night ahead. After foundation would come blusher and highlighter, then some more advanced eye make up maybe, a shimmering sparkly colour palette she wanted to try out to turn heads later.

Then it would be onto outfits. She might have a couple in mind, perhaps a tight fitting bodycon dress, although that would limit her choice of bras. Or a new white halter top she had just ordered. And could she be bothered to wear heels? Women often moan about the time it takes to get ready but for me, I was so jealous of this experience and all these choices a girl about to hit the town had laid out before her. For me ... V-neck or polo shirt was about all it came down to. Of course I could dress more extravagantly as a guy, but at that point in my life I just simply didn't have the confidence. I indulged my girly side by putting on a bit of Taylor Swift as I got ready, and opted for a plain white tee.

I met the crew in a pub in town where we stayed for a couple of hours downing cheap drinks, and despite the last few days, I actually ended up settling into a good time. Curtis hadn't arrived yet, he was meeting us later so there was no awkwardness on that front. The alcohol was lowering my inhibitions as nature intended, and for once my mind wasn't solely on Eva and what had went down at Sweet Wednesday. We even took a couple of shots. It was me, about five guys from my immediate friendship group, and three girls I knew fairly well but not massively, including Steph. My eyes still lingered on their outfits, jealous at what they were wearing, and although they probably thought I was checking out their bodies, it was the material that adorned them that I was really interested in.

By the time we were lining up in the queue for the club, I was proper drunk and really buzzing, like the carefree 20 year old that I forgot I was sometimes. It had been great reconnecting with some of my old school mates I hadn't seen since coming back from uni, and we bumped into a load of other people I vaguely knew from school and around town. The girls in our group seemed cool as well and so far we were all getting along great. The chats in the queue, waiting to crawl forward an inch at a time, weren't exactly flirty but everyone was cutting loose and relaxing, letting their guard down in that nice way you do when you're drunk but not completely out of it yet. Twenty minutes later, we were inside and ordering more drinks at the bar when I heard a familiar voice.

"Hello hello, did you miss me?"

"Curtis!" Jane, one of the girls in our group, shouted out our friend's name and ran over to hug him.

I turned to see my best mate standing there, smiling while being bear hugged by the tipsy teen. I beamed a giddy smile back at him and mimed the internationally acknowledged sign for the offer of a drink. He gave me a thumbs up back, and I swivelled back to the bar I had been leaning on and asked them to add another pint to the order. After Jane had released him, I carried our two drinks over and we clinked glasses.

"Cheers!"

"Cheers, man! Thanks for the drink! To a great night!"

And we clinked again. This was all completely normal. Maybe it was the alcohol but there didn't seem to be any awkwardness at all. Or maybe he just didn't care. Maybe if I plucked up enough Dutch courage later, I could explain myself.

"Shall we go dance?" Curtis asked.

"Yesssssss!" Jane screamed at the top of her lungs.

A pint and two shots later, the whole gang was in the middle of the floor, dancing along to some club remix of Call Me Maybe. One of the things that I loved about Curtis was, unlike some of the guys around us, he was proudly singing along every word and joining in with the girls. He didn't care what others thought about him, he was just in the club tonight to have a good time. When the song ended, Lewis mimed smoking a cigarette over the heavy volume of the music and we all nodded and trundled out to the smoking area. The outdoor section of this particular club was one of those more upmarket ones with benches and large standing heaters.

We all partook in the usual smoking area gossip and giggles. I'd finished my drink and to return the favour from earlier, Curtis motioned to me if I'd like another and I gladly accepted. He trotted back to the bar, passing by a girl who was drunkenly stumbling towards me with a finger pointed at me.

"Alex," she slurred. "Why didn't you add me on Facebook?!"

"Sorry?"

"It's me, Grace! I added you and you didn't add me back! You rude boy!"

Oh, that's who she was, I laughed to myself, Grace from the other day, Steph's friend. She seemed perturbed at my laughing so I apologised.

"Sorry, I don't check my Facebook much! I'll add you now."

"Well that's alright then. I tried to tag you in that photo but it wouldn't let me!"

Pulling out my phone, I signed into Facebook and sure enough there was a friend request there from Grace Walker and a request to tag me in a photo, the one of us all outside the train station the other day. I opened the photo and held up my phone to show her.

"See, all done now!"

For some reason in her drunk state, this made her extremely happy and she went in for a huge high five, just as Curtis was coming back with our drinks. She went just as wild for him too and for about five minutes, we briefly entertained this drunk girl we barely knew as she told us all about the boys she had lined up to go home with tonight. Curtis and I nodded along, sneaking smirking glances at each other.

"Anyway boys, it's been lovely to chat with you but I need to go DANCE!"

Then she was gone. We both laughed with relief, as drunk girls can be hard work sometimes. I thanked him for the drink and looked around and realised the others we'd come out with had obviously gone back in.

"You having a good night, man?"

"Yeah," I replied. "You?"

He nodded and we both took a sip of our drinks.

"Alex..."

"Curtis..."

Chuckling at having both spoke over each other at the same time, he told me to go first but I insisted he did. Given how drunk we both were, this went on for a full minute before he opened up.

"Well... it was just... all I wanted to say, you don't have to say anything, but whatever it was you were doing on Wednesday, it's cool and I don't care..."

"What do you mean?" I stammered, completely taken back.

"Look Alex, I know you didn't mean to meet us there. You were pretty shocked and nervous when you saw us. I know you. And yeah, later on I saw what you were wearing. And that you were trying to hide it. I'm sorry if I accidentally made you feel uncomfortable."

I felt myself almost begin to tear up at such kind words from Curtis. I gulped and pulled myself together. There was no point trying to completely deny it.

"Um, well thank you so much, Curtis," I said awkwardly. What was it about two guys having a deep chat like this which made it so hard to share our feelings openly? "I don't mind telling you. Especially as you've been so cool and accepting about it..."

"So are you a crossdresser?"

Was this actually happening?

"I guess you could say that, haha! I'm not really sure what it means to be honest, I'm just experimenting."

Did I actually just admit that?! Curtis ran his hand through his head, trying not to look too shocked or surprised, making me feel at ease still.

"Well I think its cool that you're trying something you're into, man! And don't worry I won't tell anyone."

If anyone had seen me then, they would assume I was struggling with really bad sunburn with how red my face was. Curtis grinned sheepishly too. Yeah this was a little intense and weird, but he wasn't disgusted. He was fine with it! What he said next though I was completely not expecting.

"I mean, again keep your mouth shut, but I can kinda see the appeal. I don't think for me but ... I don't know, sometimes guys in girls' stuff can be quite hot. And I'm not gonna lie and say I haven't watched trans porn. I wouldn't say other men normally did anything for me, but that blurred line between the two genders... yeah, it's something I think is pretty cool. So ... and again you don't have to say if you don't want to, but what were you up to on Wednesday before we bumped into each other then?"

How much to tell him? I think he could handle his best friend being a crossdresser and having sex with guys, but maybe not to the level of the sissy orgy I had experienced on Wednesday.

"I was with a guy. From Grindr. You know that gay dating app."

This time Curtis couldn't hide the surprise on his face.

"Oh right, wow. Well, obviously completely cool, man. I just had no idea. Do you think you're gay... or bi then? Or just experimenting like you said?"

"I think just exploring for now. But I know I do really like guys. And I think I like girls. But I'm not sure if I like them in the same way you do. Sorry, that makes no sense. This is all quite new so please don't say anything."

With our friendship, I absolutely trusted that he wouldn't, but he assured me anyway. Just as I wouldn't tell anyone about his startling confession that he potentially had a thing for androgyny and trans girls, now that was a surprise. Neither of us said anything for a second, both waiting for the other to say something and then we broke out laughing, filling the empty air. Something huge had just been shared between us and yet the friendship was still intact and maybe stronger than ever. And it felt good. It felt amazing! Being honest with someone about what I was, and getting no judgement back. Maybe coming out would always feel this joyful although I couldn't count on everyone's reaction being as understanding as Curtis. Sensing that I didn't really know what to say, he broke the silence.

"Well anyway, like I said, it's no big deal. Shall we go join the others?"

I nodded, completely unable to stop a grin spreading across my face. He returned it and we both headed back inside. After all the drinks I had I could feel my bladder burning so I told him I'd meet him on the floor and was just going to pee. As he was halfway up the stairs to get back in, I shouted up to him.

"Curtis... thank you. Honestly."

"It really is no big deal. But at the same time, I'm proud of you mate."

When he reached the top of the stairs and turned the corner, I let out a great gasp of relief and happiness. I could cry from the sheer gratitude I felt towards my friend and his lovely words at that moment. This night was going great, and I couldn't wait to get back on the floor and dance the night away. In the bathroom, I pulled up to a urinal and did that disgusting thing too many of us do and pulled out my phone to check for texts while I was peeing.

The first thing that came up on my phone was the photo from Wednesday that I had been showing Grace before. There I was, arms round Lewis and Curtis. My friend who accepted and understood me. After I'd washed my hands, I kept looking at it for a second, looking at the two of us, thinking how grateful I was for him and our bond. I zoomed in so I could see our faces more clearly. That's when I saw it. That's when I got my second chance. I couldn't believe it!

Captured in this photo from a woman I barely knew was what I had been longing for this whole week. As I zoomed in further on the arm draped around Curtis's shoulder, there was Eva's number, just about legible in its pixellated form after I had blown up the picture as far as was possible. Eleven numbers which held so much promise. What had I done to deserve a second chance from you God?

Luckily, I've always had a peculiar ability to memorise telephone numbers within seconds. I took the digits in and opened my contacts app and added Eva. When it was in, I pulled up a blank text and thought about what to say. Eventually I settled on:

"Hi Eva, it's Amy. We played together at Sweet Wednesday last week. I'd love to do it again some time. Amy xxx."

My finger hovered over the send button and perhaps if I hadn't had as much to drink as I had, I would have had second thoughts, but no, I wanted this, I was doing it, I clicked Send. It was out of my hands now. If Eva wanted me, more like if Eva even remembered me, she'd be in touch.

Suddenly I didn't want to go back in and find the others, dancing seemed irrelevant now. I just wanted to wait in the smoking area to see if Eva would reply. But coming out of the ladies' toilet, Steph saw me and pulled me by the hand, imploring me to join the others. Reluctantly, I slid my phone away and followed. It was about 1am now and the group was still going strong, hogging the centre of the dance floor. I joined in but my mind was on other things. Checking my phone constantly, had she replied, was it on vibrate? But no, nothing.

Half an hour later, I suddenly felt a bzzt bzzt in my pocket. A text! While the others were all dancing along to a Beyonce remix, I made my excuses for a toilet break, then snuck out to the smoking area and found an unoccupied corner where I wouldn't be disturbed.