Sweet Wednesday Ch. 01

This was a particularly enjoyable and personal story to write, because it's largely all true. It's a real place that exists in London, it was one of my first meaningful experiences dressing up in public and all the femme characters in the story really did exist, with names changed obviously. Some of the sexual encounters have been embellished for good, sexy storytelling but most of this did all happen and does actually happen at the real Sweet Wednesday club. So enjoy!

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I stood outside trembling, having walked past the entrance four or five times now, trying to be inconspicuous and probably failing. Passers-by were staring at the twenty-year old fresh-faced boy who was just standing around in the street, furtively glancing over at the pub that was stationed on the corner and nervously fiddling with the straps of his rucksack.

The bag was filled with cheap female clothing and frilly, skimpy lingerie I had just picked up in Primark. I was standing outside Central Station in Kings Cross, London, an ordinary looking pub from the outside. But its underground basement played regular host to a series of adult events mainly aimed at gay men. In its darkroom below stairs, businessmen could slip in to partake in some cocksucking or to fuck a young twink, or maybe a bear, depending on the event. Today's event though wasn't quite the same. Billed as 'Sweet Wednesday', this fortnightly event was proudly aimed at 'Tgirls and their admirers'. While I had only dabbled in it it before, this was going to be my first attempt at becoming a Tgirl in public. The term I preferred though was sissy.

The word sissy fills me with such joy. It did on that day nearly ten years ago, and it does just as much now. There's a hyper femininity to it, ladled with connotations of submission and humiliation, my ultimate kinks. Sissies are pathetic and worthless and just hearing a real dominant voice tell us that makes our little clitties stand on end. I'd only been a proper sissy for a couple of months as I stood on that street that day, having sucked my first cock at the start of that summer. Now I was on a journey I would never recover from, and had taken the plunge from meeting men secretly and in private on Grindr, to exposing myself at a dedicated sex club for crossdressers and the men who love to fuck them.

I summoned all my courage and told myself I wanted to do this. I had to take an hour long train to get here, as I lived outside London and still with my parents, which frustrated my sissy desire for dressing up. Not only that but I had just spent nearly a week's wages, admittedly not a lot back then, on new outfits. Outfits I hoped to impress real men in. I took a deep breath and crossed the road.

It may help to explain the way Central Station is set up. As said, really it's just an ordinary pub on a corner. It makes a point of being LGBTQ friendly and you may see trans women and queer folk just having a drink there anyway. However, slightly down the street lies a side door, a second entrance that only acts as the entrance to the adult events in the basement. This was where I was heading, ready for my first taste of Sweet Wednesday.

I stepped inside and saw an attendant sitting behind a bar, laughing and talking to a tall transvestite who was leaning on the bar with her back to me. When they both saw me come in, visible shock passed over their faces. I guess at 20 I was considerably younger than the usual clientele. The man regained his composure and smiled at me and asked.

"Trousers £20, frocks £10. Which will it be?"

"I'm sorry?" I stammered, my mind instantly going blank with nerves. He chuckled softly.

"Are you a dresser, darling?"

"Erm, yes," I blushed considerably and nodded quickly.

"Lovely ... how old are you may I ask?" I told him my age and he asked to see some ID. I may have been 20 but I still had a very unmanly face and often got asked for proof of age. I pulled my driving licence out my pocket and handed it over to him.

"Thank you, darling. Now, see that staircase behind you. Just go up there and you'll find a space you can get changed, OK?"

I nodded again gratefully, paid my £10 admission fee and headed up the staircase he had pointed to. As I walked up, I thought I heard his crossdressing friend laugh and wondered if they were talking about me.

The upstairs of the pub was a bright pink room filled with little tables and stools and old-fashioned dressing screens. It was light and airy, with plenty of windows letting sunlight stream in. And to my excitement, there were five people getting ready in the room, I say people as they didn't seem like men or women, I wouldn't know which one to land on exactly. Most of them were sitting at stools, powdering their faces with makeup, chatting away, pulling their bodies into tight corsets or rolling stockings up their legs. They were all much older than me, ranging from most in their 30s and 40s, to a couple older, one definitely in their 60s. I was in heaven and I just couldn't believe I was here. One or two looked over and smiled at me, most just carried on their conversation.

I quietly walked to a corner of the room where I found an empty dressing table and sat down, taking my rucksack off my shoulder ready to inspect what I had bought. I had purchased the outfits in such a hurry that I wasn't totally sure. Not being able to try stuff on, or not having the confidence to at this stage anyway, meant that all my shopping for women's clothing so far had been a flustered mess, I'd normally just pick something off the shelves and then take it to the counter as soon as possible.

I adored the humiliation of shopping in the women's section, particularly when it came to lingerie. If I could I would peruse the lingerie aisles of a high end department store for hours, and one of my main masturbatory fantasies is being locked in one of these places all night with my Master or Mistress and being made to perform crude fashion shows for them. As much as I loved the humiliation though, I also felt the need to get out of there as soon as possible. I had run into the store earlier after getting off my train and bought myself a pair of denim short shorts, a white blouse, fishnet stockings, some high heels that barely fit my feet .. and then the coup de grace, a matching lacy purple bra and panties matching set.

Just standing line to pay with it in my arms while real women lined up around me, staring at me, made me leak precum. And now sat in this changing room with other sissies, I pulled out the garments and began to pray they fit me. It was early evening but Sweet Wednesday starts around lunchtime, so the event had been going for some time now and other dressers who had been and had their fill, quite literally, were starting to traipse up in dribs and drabs to get sadly changed back into their male attire and either head back to work or home again. I got the sense a lot of the other sissies knew each other, a real sense of community was tangible.

"How was it down there, Charlotte?" a bald, camp Scouser who was combing out his wig asked a beautiful short woman who had just come up the stairs. I say woman, the obvious bulge in her green knickers told me otherwise really, but there was no other word to describe her. She looked so feminine you would never have told, until she opened her mouth and revealed a huskier voice than appearances would have it.

"There's a lot of fabulous cock in there tonight, darlings. I milked a lot of it as you can see," she said as she twirled round, revealing what looked like cum stains on the bodice of her green corset. "But it's filling up nicely so don't you worry, there's plenty to go round. Hello, what have we here?"

I had been gawping at her but suddenly she had turned her focus towards me and was striding over to me.

"We have a little girl up here. Is this your first time, sweetheart?"

"Hi... yes, it is ... I'm a sissy." Just that word as it left my lips, gave me butterflies, but I was proud to admit what I was, what I had come to accept I was.

"Oh we're all sissies here, darling. What's your name?"

"Amy." I had chosen the name months before when I first started to meet older men on Grindr dressed as a prancing wannabe girly faggot.

"Ladies look after Amy when she's down there, she's box fresh! Don't worry Amy, we don't bite. Some of the beasts downstairs might but I'm sure you'll be alright."

She took a seat herself and began dabbing at her face with wet wipes to take her makeup off. As I looked around at the other girls applying lipstick and mascara, and putting on wigs, I felt woefully underprepared. I had no idea how to put on makeup, I was too poor really to experiment with it and couldn't afford a decent wig either. The clothes would have to do for now.

I realised I would have to get naked if I was to slip into the purple lace I'd bought for myself. There was a brief moment of hesitation when suddenly I caught myself thinking how ridiculous that was, given what I'd come here to do. I slid my jeans and boxers down quickly, my little cocklette exposed to the other dressers but no one batted an eyelid. Besides, they'd come for real alpha cock. They knew all too well what a clitty looked like.

Feeling more confident, I stepped into the panties and slowly pulled them up my legs. Sissies reading this will know the feeling, but if you don't, it is simply indescribable. The level of satisfaction when you feel them glide up your leg and how pretty they look with your little clitty snuggled up inside them. Although I have to say my whole environment was starting to get my little thing hard and it was a struggle to contain it in the lace.

Another tgirl came up the stairs, with cum sticking strands of what looked like her natural long blond hair together. She was struggling to walk properly. She gently eased herself onto a chaise lounge that sat across the other side of the room and took a deep breath.

"How many?" smirked an Italian woman who had just put the finishing touches to her makeup, and looked completely unrecognisable from the unremarkable man who had walked in just after I had.

"At once or in total?"

"You cheeky slut. Go on then, both."

"At once, four. Over twenty in total, can't quite remember, but they were lining up to fuck me at one point."

The idea and image of that filled me with euphoria and terror at once. Is this what I wanted to become? Had I already become this? A sissy who would boast about the number of men she had just let take her in a dark room under a pub in the middle of a Wednesday. God, I wanted to be that.

I rolled the fishnets up my legs and shimmied into my little short shorts. Admiring myself in one of the many mirrors dotted around up here, I thought my butt looked quite cute. The bra was less comfortable, not designed for a flat chest like mine, but I pulled it on anyway. Even at that young age, I had the firm opinion that a good sissy should always wear a bra to complete the look. This isn't the majority opinion among crossdressers in my experience but I like to do it just for the aesthetic. Finally, I buttoned up my blouse and was ready to go.

Taking another deep breath, I began to head for the stairs when I heard a voice spluttering behind me. It was the Italian, who was looking at me in shock, makeup brush held in one hand in the air.

"What about your makeup, honey? You can't go downstairs like that."

Hearing that made me feel so ashamed and embarrassed, not even the good type. I was failing at even being a sissy, how pathetic was that? I mumbled my apologies and said I didn't have any. She just rolled her eyes at that, and pointed at the stool beside her.

"Oh go on then, I wouldn't do this for everyone, but I remember people did the same for me when I was starting out. Sit down."

My heart soared and I bounded over to her. She brushed my ear-length strawberry blonde hair out of my eyes and took a good look at my face.

"We got a lot to work with here. Now what kind of look are you going for, classy or slutt...?"

"Slutty!" I replied much too quickly, taken back at my own impulse. All the other dressers in the room sniggered when they heard, and my lovely Italian saviour just looked at me fondly.

"Oh, to be young and a sissy. Is this your first time ever dressing in a place like this?"

"I've had a couple of meets with guys where I've just worn some lingerie but nothing like this ever, no." I felt like I could really be honest around these people, they more than anyone understood what I was.

"Well you just be careful down there, it can get pretty wild. I'm Claudia. I'm going to be going pretty wild down there too if I'm being honest, but if you need anything, you just come and find me. Now hold still."

She set about applying my makeup. I had never had any makeup put on me before, and I loved the experience but was unexpectedly harder than I'd realised, particularly when Claudia went around my eyes. After twenty minutes, I was all done. All I could do was thank her for her generosity.

"Normally I'd charge for that, but I was you twenty years ago. Have fun down there, what's your name again?"

"I'm Amy. Lovely to meet you, Claudia." And with that, I did the only thing that felt natural. I curtsied. She just rolled her eyes at that again.

"See you later, Amy. Don't do anything I wouldn't do."

In a daze, I turned and went through a door, completely buzzing on what had just happened, absentmindedly trotting down the stairs. It was only when I got to the bottom that I realised these were not the stairs I had come in via. I'd inadvertently come out in what was a backroom in the main pub. And standing there were two, 100% cis men in their early twenties, not much older than myself, just looking at me.

I still think about this experience years later. I guess it was my first experience of public humiliation, a major fetish of mine. I just stood there frozen, for as good a job as Claudia had done, I was still clearly a boy in lingerie and they absolutely knew it. My body flooded with adrenaline, fear and excitement from being watched in this way. But they didn't say anything, didn't laugh and thankfully, didn't get violent. On reflection, they were in an LGBTQ friendly pub, maybe they were used to it. Maybe they even knew about Sweet Wednesday and were summoning up the courage to go down and check it out, although I never saw them later. They just watched me.

As I regained my senses, I turned and hurriedly went back the way I'd came and found the right door I was supposed to go through, which took me back to the entrance I had come in at. Next to the bar was a winding set of stairs into the basement, with a red curtain covering the way. The man who had sold me my ticket looked me over up and down. I felt proud to be the object of his gaze.

"So sexy darling."

"Thank you," I giggled. I actually giggled, that was how girly I was feeling.

He turned and gently pulled back the red curtain for me to step through. Walking on my new high heels was hard going, but I delicately placed one foot on the descending stairs into the darkrooms of Sweet Wednesday and entered what I had been dreaming about for weeks. I first came to a cloakroom where I handed in my rucksack. Behind the window was a dark-skinned woman, or crossdresser, I honestly had no idea, wearing a black and white corset and fishnet stockings similar to mine, who gave me a huge smile.

"They are going to absolutely LOVE you in there. How old are you if you don't mind me asking?"

"I'm 20."

"Wow ... OK, good luck."

Stepping through another red curtain, I found myself in the main space I was going to be spending the next few hours again. Again, maybe some scene setting will be helpful here. The basement was largely split into two sections. As I came in, on the left of the total space, there was a dimly lit section with a bar serving drinks, and a couple of chairs scattered around with mainly other dressers like me, sitting around and catching up. To the right, the lights got considerably darker and distinctly red. The two halves of the room were separated by a black curtain hanging between the walls. I knew this was where the majority of the action was going to take place and was excited to explore the darkrooms that lay behind the black curtain. So many curtains, covering so much sin!

There were small, cheap flatscreen TVs stationed on the walls, and some projectors playing onto the exposed brick wall, all showing hardcore TS porn. One just to the left of the bar showed a woman with what must have been an 8" hard cock standing over another kneeling woman, whose secret was betrayed by the two balls that could be just spotted dangling below her bare ass. The standing goddess was ramming her cock in and out of the submissive transsexual slut's throat, her fake boobs bouncing up and down as she leaned into the brutal face fucking. I wonder how long it would be before that would be me on my knees tonight. By the time I stepped back through those red curtains and back into the outside normal world, I wanted to go further than I'd ever gone before.

Loosening up a little would help, so I slowly walked over to the bar, trying to look sultry in my heels but really just attempting to maintain my balance, and ordered myself a G&T. I normally drink beer but a G&T just sounds so feminine. It came with a little straw and I liked being able to suck it as I looked round the club, hoping to make eye contact with anyone. Sizing up the space, the ratio of men to crossdressers was probably around 60:40. Nearly all the men were alone, whereas some of the tgirls were standing in groups.

One shy woman was sat a couple of chairs away from me, definitely on her own. She looked absolutely petrified. Whereas most of the sluts down here were wearing pretty skimpy outfits, corsets and body stockings, or tight shorts that only just held all their organs in, this one was wearing a knee length white sundress. Like me, she had no wig on but her mousy brown hair was close cropped enough that it looked like a regular little pixie cut. Her makeup however was immaculate, when I could actually see it when she wasn't staring down at the floor at her white plimsoll shoes. The only other aspect of her outfit that belied her innocent appearance was a collar attached around her neck, black with a little heart shaped loop at the front. As she looked up, she caught my eye and I turned away embarrassed.

It was time to explore the darkroom. With my drink clasped in both hands, I went through the black curtains and into the red lit space. Again through more curtains hanging, I now saw the space was divided up into lots of little pockets, almost like a maze. Some bits were more secluded than others, giving privacy to those who wanted it. Some were definitely already taking that option, as curtains rustled and low moans emanated out.

Men, mainly old men who looked like they should be retired, were standing around in the dark, stationed everywhere. Most were fully dressed but were stroking their dicks, belts undone and trying to glimpse any action they could. As I slowly strolled through the maze, I began to feel their hands on me. I loved their touch, loved the feeling of being groped by their paws, but kept walking on to explore. I had read that the common code of conduct was that this touching was allowed and encouraged, and if the gropee lingered, they were up for more. I continued on into the darkness however and these leering men left me alone.

I came out in a wider open space, directly under one of the glaring red lights. There were two red leather boxseats in the middle of the space, around 2 metres square each. I don't know how I would describe them exactly, I guess they were similar to what you would sit on when going for a shoe fitting, a long leather expanse to recline on. The one to the right was empty but the one on the left was occupied. Occupied by something straight out of my porn collection, lifted from one of my wet dreams.