Sweet Wednesday Ch. 02

Thanks for all the lovely comments on the first chapter of this story. This chapter will be much more plot heavy than the first although there is some still some sexual stuff scattered throughout. The series will also explore some of the tensions within the trans and gender questioning scene, so there will be some slightly heavier sections as it goes on. Would absolutely adore any feedback or comments. Hope you enjoy! xxx

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After what had been one of the wildest experiences of my short life as a sissy, I stumbled out of the bar dripping with shame and out on to the street in boy mode. Even though I had tried to wash the cum off of my face, after taking at least five loads in the Sweet Wednesday basement, I couldn't escape the paranoia that everyone would know what had just been on it. My girly clothes were safely ensconced in my rucksack. I nearly convinced myself to just chuck the bag in the river, at that moment in time I never wanted to wear them again, never wanted to be Amy the sissy again. However experience told me that once I was out of this sissy shame spiral, I probably would want my things back again and I didn't have the money to splash out on a new outfit every time.

I told myself I just needed to get on a train and get back home, scrub myself completely clean in the shower and go to bed and try and forget how far I had let myself slide. I had intended on being somewhere dressed up femme, maybe have some action... I hadn't expected to be fucked by as many guys or take as many shots of cum on my face as I had in there. What happened in that basement stays in that basement, that's what I told myself. And no one but me knew I had been there. No one but me and my fellow sissies I had got ready with of course.

As much as I had tried in the mirror in the little bathroom of the changing room to get it off, there were still lingering traces of mascara around my eyes. I couldn't really work out if someone looking at me fresh would be able to spot the crossdresser in me but it was best not to risk it. Which is why when I heard my name loudly called in a familiar voice, my heart stopped dead.

"Alex? What are you doing here?"

I turned around to see my best friend Curtis grinning and walking towards me. Just behind him, I could see our other mutual friend Lewis and his girlfriend Steph, next to another girl I didn't recognise. Curtis bounded up to me and pulled me in for a hug. I hoped that he wasn't too familiar with the smell of cum, I was sure I reeked of it.

"So good to see you! You said you couldn't make it cos you were working today?"

Brain unfreezing and clicking back into life, I remembered some talk of a day out in London a while back which I had made excuses for, knowing I was heading for my little sissy adventure.

"Oh yeah, well I managed to get it off in the end ... so I thought I'd meet you here."

"Oh you should have texted to let us know. I've ended up getting roped into a double date and it's a bit awkward. Hang on, they're coming now so don't say anything."

Lewis approached us and went for a high five, which I returned while trying to calm myself down and stop my hand from shaking. I'm just a normal guy, I'm just a normal every day man who has bumped into some of his other male friends out and about. Totally normal. They have no idea what you were just doing. Visions of licking sweet cum off Josephine's face, getting rammed by myriad anonymous men and cumming on Eva's tits played through my brain...

"And this is Grace," finished Lewis, introducing the other girl I hadn't met yet. I said my polite hellos.

"So Alex, are you joining us for the film?"

"Um, hell yeah! Why else do you think I'm here?"

Certainly not to dress as a panty boy and suck strangers' cocks in an underground sex dungeon as far as you're concerned, Grace, I thought to myself.

"Nice one," said Curtis. His smile was so infectious and he seemed over the moon that I had turned up from nowhere.

Curtis was one of my oldest and best friends from school, we went back years. Similar sense of humour, similar outlook on life, both pretty chilled although he was certainly more confident in himself and his body than I probably was at that time. When I was around him, I felt like my presence was appreciated and generally wanted, which gave me a sense of calmness and confidence that someone so cool was excited to have me around.

And so with my rucksack stuffed with cheap, and now stained, women's clothing, we headed off to the cinema. As I began to walk though, I could tell something was slightly off, something didn't feel right. Something kinda scratchy. When it finally twigged, dread consumed me. In my haste to get out of there, I had thrown my jeans on straight over my purple lace knickers! And now as I walked along with my friends, I could now feel the distinct feeling of the lace dancing against my balls.

Now I started to really panic, as much as I tried to keep my cool walking along and maintaining casual conversation. What if my T-shirt rode up and someone saw? My sissy secret exposed! I would just have to be extra careful. Besides we were going to a cinema, it would be dark. There really was nothing to worry about.

Given everything else that went on on that monumental day, I can't honestly remember now what film the five of us saw and with my nerves in the state that they were, I doubt I took much in at the time. I just sank into my seat, laying back as far as possible. I sat next to Curtis on one side, Lewis and the girls on the other side of me. The film went by quickly, Curtis whispering some jokes in my ear as it went on but I wasn't really in the right mood to return the favour, just laughed along and went with it.

Soon it was over and we all stood up to go. Out of habit as were about to leave the aisle, I patted down my pockets to check I had everything.

"Shit, where's my phone?"

"Did it fall down the side? Hurry up, I really need to pee!"

Oh God, if I was to bend down and retrieve it, there's no way I wouldn't show off my purple sissy secret tucked away under my trousers. I froze on the spot, contemplating my dilemma. The others looked at me quizzically as I just stood there motionless, saying nothing.

"What are you waiting for Alex?"

"Yeah fuck this, let's go to the toilet," moaned Steph. "See you in the lobby?"

"Yep!" I said enthusiastically, trying to encourage them to leave so I could retrieve my phone in peace. "See you in a sec! You guys can go as well."

Lewis nodded and turned and followed his girlfriend out the dark room, but Curtis whipped out his own phone and hit the torch, shining the bright white light at my feet. Any other time this act of kindness would have been appreciated but right now it was the last thing I needed. But what else could I do? All I could think of was to get it over as quickly as possible. Not for the first time that day, I fell to my hands and knees and tried to look for it as fast as I could, praying that my knickers weren't exposed even though I knew that was pretty futile in this position.

I really had to get under the seat and when I eventually saw it and managed to get a finger tip on it, I felt the fabric of my shirt glide up my body and the waist of my jeans pull back. If Curtis was looking anywhere near where his light was focused, on me on the ground, how could he not have seen me? Phone in hand, I got up and turned to leave, trying not to meet his eye but also scanning for any tell tale signs that he'd clocked me. Was I imagining it or was he averting my gaze as well?

"Um, shall we get going?"

Curtis nodded and we walked out in silence, until we met the others in the lobby. Then we were able to flow more easily into chat about the film, allowing me to feel a little more comfortable and normal.

"Hey Alex, what's that on you?" Grace was pointing at the mobile number scribbled on my arm.

"Oh.. um, it's just a mobile number for work... a colleague I'm meant to be swapping shifts with."

I had forgotten about the number Eva had left on me, making her mark on my sissy skin. The beautiful transsexual had made sure to give it to me as I was desperate to leave that place, and implored me to get in touch with her. Would I take her up on her offer? As I was contemplating it, I noticed Curtis looking more closely at my arm and subconsciously folded them, feigning coldness despite it being the middle of summer.

We left the cinema and headed back to the train station. We were all heading back to our hometown aside from Grace who was going in a different direction. The two girls hugged profusely and Grace whipped out her phone, grabbing a passer-by.

"Hey, do you mind taking a photo of us? Come on everybody, get in the shot!"

We all bunched up, shorter girls at the front and us three guys at the back. Well two guys and one sissy boy really, we could hardly be said to be the same thing. Somehow I found myself in the middle and did that stereotypical pose of putting my two arms round my friends. The stranger took the photo and handed Grace her phone back.

"Well I had a lovely day, and it was lovely to meet you Curtis. And you, Alex. See you later!"

We waved her goodbye and headed to our own train. Lewis and Steph chatted amongst themselves but I noticed Curtis wasn't saying a huge amount now. Oh God, he had seen. He was onto me, I just knew it. The whole way home all I could think about was how ruined my relationship with Curtis was likely to be if he'd discovered I was a little sissy. Had I jeopardised my best friendship for one day of dressing up femme and throwing myself at men so they'd pound my ass?

As soon as I eventually got home, I rushed straight to the shower, barely sharing two words with my parents, determined to get the disgusting traces of that day off me, thinking it would do something to rid me of the shame I was feeling so intensely at that moment. It had been bad when I left Sweet Wednesday but after the way I'd left things with Curtis, a definite awkwardness in the air between us, it was through the roof. I got under the steaming hot shower and began to scrub it all off me, the dirt, the sweat, the dried cum and the inescapable sense of regret that was built into being a sissy.

Water so hot it was scorching me, but I didn't care. Eva's number on my arm was coming off as it dribbled off me, cleansing me of being Amy and sending me back to being Alex. I was going to stop doing stupid things like Sweet Wednesday and risking my friendships. I was going to stop being a sissy. No more Josephines, Ariels or Evas. Her number was gone, my arm was clear and I was going clean...

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Any sissies reading this can imagine how long those admirable sentiments lasted. That night I dreamt of sissy wonderlands more intensely than I ever had before. I was with Eva in a high-end lingerie shop, with red walls and everything you'd expect from such an establishment except the shopgirls were eight feel tall and all the bras and panties on display were all gleaming and shining with some kind of pulsing light emanating from them.

We browsed the store together, Eva making me try things on then and there. Every time I slipped into some new lace or satin, the giant women would clap and applaud me, and I blushed, my cheeks a girlish red. One of them walked over to the shop entrance and locked the door, trapping me inside with them and they all began to strip. To my surprise, every one of them had a phallus hanging between their legs at least a foot long. Even more bizarre, suddenly a button was pressed and the floor panels in the middle of the room slid away, revealing a small but empty swimming pool.

"Let's find you a swimming costume, Amy!"

"But there's no water?" I replied.

"You're so silly," laughed one of the women, in simultaneously somehow the most high pitched but deep voice I'd ever heard.

They clicked their fingers and my outfit changed into a one-piece bathing costume, navy blue with white polkadots. I felt a hand on my back push me face forward into the pool. I landed hard and blood was definitely trickling into my mouth.

All the giant women and Eva stood around the side of the pool, Eva with her smaller cock out now, all beginning to play with themselves. Through the tears that were starting to form in my eyes, I saw them steadily begin to bring themselves to climax, before gigantic spurts of cum began to fill the whole pool, so that I was bathing in semen, drowning in cum...

"We're going to breed you, you pathetic little bitch, do you understand?"

"Yes, ma'am," I tried to reply while trying to paddle to stay afloat and not let the cum pull me down and fill my lungs.

"Time to open up again, I think ladies," said Eva and the doors to the store were flung open.

Brilliant sunshine flooded in and streams of people followed, my whole school year, all my work colleagues, my close and extended family, my best friends and random members of the public. All here to see me, drowning in this pool of cum. The humiliation burned so strongly that I couldn't hold anyone's eye for more than a millisecond, each person I saw I understood they now knew truly what a worthless sissy I was.

"Who wants to breed her first?"

And I couldn't take it anymore. I screamed at the top of my lungs, and stopped trying to paddle, sinking under the surface and letting the cum wash over me...

That scream had obviously happened in real life too, because just as I woke up from the dream, sweaty but rock hard under the covers, my dad poked his head around the bedroom door to assure I was OK. Just a bad dream, I explained, hurriedly trying to get him out of my room so I could do what I knew I had to do as soon as possible. As soon as he bade me goodnight and left, I shimmied over to the door awkwardly, making sure to hide my erection so no one in the hall could see it, and locked it. There was no way I was sleeping tonight without taking care of myself first.

Under the bed was the rest of my secret stash of sissy gear, mainly panties of various sorts but a couple of bras and some nightwear, camis and teddies and the like. Oh and obviously some stockings of course. For what I wanted to do just then, I would need three pairs of knickers. I selected a classic black lace pair, some pink cotton and then a frilly white pair with little red love hearts dotted on them. The latter pair were the cutest, so they were the ones I slipped into, loving the feeling of them cupping me, but having to arrange them round my throbbing hard dick.

I laid back on the bed and then shoved the pink pair down my throat. I wanted to choke myself. And to top of the effect, I took the black lace pair and slipped over my neck and then pulled tight. God I loved that feeling! I would never pull tight enough that it would do any actual damage, but enough so it felt like there was someone there choking and dominating me, a strong alpha man, or maybe even someone like Eva...

This admittedly ridiculous ensemble was pretty much how I always masturbated at that point in my life. Knickers on, mouth gagged, neck constricted, door locked and headphones in. I did the only thing left to do and typed in the three words into my laptop resting next to me that would have almost certainly autocompleted had I not been in private browsing mode. SISSY. HUMILIATION. POV. Thousands of search results came up and I skipped past the hundreds I'd seen before, the classics and the not so classics, all videos filled with gorgeous and domineering women sneering at boys like me. On the third page, I found a video title I was sure I hadn't seen before, SISSY BRED FOR MISTRESS'S DELIGHT. Yes please!

The video opened and a redhead women, probably in her late 20s, sat on a bed facing the camera. To my delight, she wasn't geared up in a dominatrix outfit, just a white tight fitting tank top that showed off her C-cups and a little red skirt. I'm not sure why but it always turned me on much more to be humiliated and dominated by women who seemed like they'd walked out of real life, rather than an overt BDSM style outfit that could be hot but was ultimately more of a performance. I had no desire to fuck these women, I knew that my worthless sissy cock would barely scratch their walls, but it was their femininity I longer for and envied, and the way they could weaponise it against a bitch like me. And even though I mainly lusted after cock, there were times when I brought myself to climax thinking of a plastic strap on cock filling my ass with a beautiful women like the one on my screen now driving it into me.

"Hello my little sissy. It's Mistress Justine here."

At hearing her call me a sissy, I let my hand trail down to my waiting cock and held it firmly. It was hot and pulsing. After the dream I'd just had, I knew it wasn't going to take long to cum to Justine's sweet words.

"Don't you look cute in your outfit, baby? You got everything I told you you'd need for your breeding didn't you? Say, yes Mistress Justine!"

"Yes, Mistress Justine," came my muffled whisper through the panties stuffed in my mouth.

"You look so pretty in those panties I lent you!"

That nearly pushed me over the edge so I loosened my grip on my shaft, wanting this sissy magic to last just a moment longer.

"My fellas are gonna be here soon and we'll get started. Remember like we agreed. They're gonna breed you so good, baby."

My heart was beating so fast at hearing these trigger words, I knew I was going to cum in a matter of seconds. With the hand that I had been using to choke myself with the black lace panties wrapped around my neck, I eased the pressure and unwrapped myself from them, bringing the black material down to my pre-cum dripping dick instead, knowing I was about to cum imminently. Jasmine slid off the bed seductively and stood up, beginning to unbutton her skirt.

"Maybe Mistress should have a little practice go on you first baby, how does that sound?"

Without realising what I was doing, I began to nod. The black lace was fully wrapped around my hardness now, waiting to catch every ounce of cum that was about to erupt. And erupt it did, when Jasmine unclasped the last button and the skirt floated down her legs, allowing the tightly coiled purple silicon strap-on that had been pressed down by the garment to spring up and reveal itself. The sight of Jasmine's glorious strap-on pushed me over the edge and wave after wave of cum gushed into my panties and my body rippled with ecstasy.

Fuuuuuuuck!

Instinctively, I shut the laptop. I had to clean up the mess first before I could do anything and oh boy was there a lot of mess this time. The black panties came away from my cock with some sticky difficulty, but they had caught most of the cum at least. A couple of hours ago I had determined to leave this sissy lifestyle behind me and now look at me. I couldn't even make it 24 hours! And curiously that fact, instead of filling me with shame like I normally did at these moments, acted as a weird kind of comfort. After the day I'd had at Sweet Wednesday, why was I bothering to pretend?

Acting like I wasn't a sissy when deep down I knew it's what I was and what I truly wanted. I had gone to that club and had one of the most fulfilling sexual experiences of my life, riding who knows how many cocks, and even after all that I couldn't go a couple of hours later on without making myself explode to sissy porn all over again. Why even bother to pretend I could escape this cycle? Fuck it! I was going to be what I wanted to be and no one could stop me. And almost as if to prove it to myself that I really had mentally embraced how low I had sunk, I spat about the panties that had been rammed down my throat and raised the other cum-filled knickers to my mouth and began to lick it all up and clean the mess I had made like a good sissy.