Sweet Wednesday Ch. 01

The alpha men in the basement all laughed and assured him it wouldn't be. Josephine knelt on the floor and pulled her white dress over her head, sitting there with a bare chest and the white petticoats I had seen earlier. It didn't take long before some of the crowd who had been around me and Ariel flocked to her, all eager to deposit their loads on her face. Whoever it was that was fucking me was obviously content with my hole however, as they stayed buried deep inside my sissy pussy, fucking me at a nice consistent pace. I was beginning to leak precum into my knickers!

While I continued to take him as deep as I could, I had a lovely view of the bukkake that was beginning to unfold around Josephine. It was incredible to me that someone who had seemed so shy earlier could be the centre of attention in this scene, but she was taking loads like a champion. Men were lining up and aggressively wanking in her face, before their orgasms exploded all over her. So far I had seen three men unload themselves on my new friend, one firmly gripping her chin and pinpointing his aim on her face, the second spraying all down her chest and the last one had missed her tongue where he had aiming so that she now had thick strands of cum in her hair. I was a jealous sissy!

But to my disappointment, someone walked in the way of me, blocking my view. As much as I could crane my neck up while I was still getting filled from behind, I was able to work out it was the man at the front desk who had sold me my ticket earlier.

"I've been looking for you. I've got fifteen minutes break and I want to taste that little sissy mouth of yours."

He unbuckled his jeans and fished out a semi-erect cock. I didn't have to be told to open my mouth, I just did it on instinct and two seconds later, both my holes were now cock-filled. I was sad not to be able to watch Josephine being glazed with delicious man juice but my duty to please a waiting cock in front of me came first. Obviously. Could I call myself a prancing sissy faggot otherwise?!

The ticket man didn't take long to bring to orgasm and soon he was shooting his hot load down my throat, the first of the evening that had actually gone to my belly, after Ariel's which was drying on my face. He thanked me for the head and headed back upstairs, leaving me free to watch the action in front of me.

"I'm fucking close," muttered the ginger brute that was fucking Angel over the room from us. His thrusts had picked up in intensity and he was slamming into the Filipina's tight hole now.

"Yeah, cum in me Jack, cum in my little pussy!"

"I'm going to fill you with cum. I'm fucking cumming." Clearly, he needed to verbalise things to push him over the edge and Angel was clearly not shy in the dirty talk department.

"Mmm baby, you're so big and hard inside my girly little pussy, it can't take much more, flood my ass with your manly cum and ...,"

Before she could finish, he roared and began shaking. I watched in awe, unable to see his dick, but able to tell from the way their bodies were both pulsating that he was depositing big loads inside her. The stranger that was fucking me from behind moved their hands from my hips, up to my shoulders, pulling me back onto their cock and raising my upper body so his mouth was level with my neck.

"I'm going to cum in you like that now, you stupid little bitch."

I recognised the voice from our interaction earlier, and what do you know, of course he was right I had come back for more. All I could do was tell him how grateful I was.

"Thank you for fucking me, sir." He laughed and spanked me hard.

"Say thank you for that." My asscheeks stung but being told what to do felt so good, particularly with my tormenter's cock ploughing into me.

"Thank you for spanking me, sir."

"She's a delight, isn't she?" moaned Ariel, in the middle of her own deep pounding.

His mouth was still around my neck and I felt his teeth sink into me. I squealed in pain, which caught Josephine's attention. I don't think she realised I was there before, but upon seeing me she flashed me a sweet smile, just before another load of cum landed on her lips. The timing was completely in sync as I suddenly felt the cock buried in my ass clench and pulse and then a wave of cum fill the condom. Part of me wished it was flooding my insides right now, but deep down I knew it was better to be safe. He pulled out of me fast and spanked my ass hard, turned and walked away. I yelped but he had gone, back to the bar or off to find another sissy slut to abuse.

Angel had swung her legs off the box and tried to stand up, but had to hold onto the wall to stop herself falling over. Her man had also hurried off, maybe ashamed of himself after cumming. Perhaps he was straight and was disgusted with himself for fucking something with a penis, even if it was likely an adorable little shecock if it was anything like Ariel's.

"Come on Ariel, let's go, we're going to be late for work."

Ariel was still in the middle of working her ass up and down the dick that was behind her.

"Come on, big boy, fill me with your load. Go to town on me."

He didn't need to be asked twice and stepped it up a gear, grabbing her waist harder than before and built up his fucking pace to an intensity I think would have broken me. Unsurprisingly, it only took him a minute before his whole body crumpled, Ariel collapsed onto the leather surface and he let out a huge sigh.

"One thing quickly. Amy, get on your knees." I had just been watching absentmindedly but sprang to the floor without being asked twice.

Ariel rolled over and took her lover's wrapped cock gently in her palm and carefully rolled the condom off so it came off in her hand. I knew where this was heading. She stood up and walked over to me, where my mouth was already open waiting. I made sure Josephine could see me as well. Her mouth was filled with a cock, the last one left standing of the previous crowd that had formed around her, the others all tapped out and spent. Her eyes though were trained on me, watching.

"Give it to me, Ariel," and I opened my mouth, tilted my head back and invited her to pour all that lovely cum down my waiting, pathetic throat. Angel and Ariel looked so proud of me. It slipped down my throat and I licked my lips to show these two older tgirls how satisfied I was.

"I'm impressed, didn't think the little girl had it in her," Angel admitted. "Come on, let's get moving Ariel."

They turned to go but not before Ariel stooped down to my kneeling form and gave me a little kiss on the forehead.

"Hopefully see you here next time baby? I'm always here."

"Definitely!" I grinned up back at her, my face still painted with her girly cum from earlier. They walked out past the curtain, leaving me alone in the room.

There was a grunt from behind me, probably Josephine's last customer. As I turned around, he was zipping his fly up and strutted out. With everything else going on around me, I hadn't noticed everyone else had left this little curtained-off section. It was just me on my knees and Josephine on hers, a metre or so away from me. The last guy had came over her eyes and she was struggling to get them open. Silently, I crawled over to her.

As she opened her eyes and surprise registered on her face at how close I was, I just wanted to do something loving towards this stranger I felt such a sense of sissy kinship with. Without either of us sharing a word, I leaned into her and began gently licking the cum off her chest, neck and face, slowly cleaning her. I did that for about five minutes, with no sound but her gentle cooing at how nice my tongue felt, and the distant sounds of sex coming from elsewhere in the basement. Our bliss was only interrupted by the return of her master.

"Well, they did do a good job on you, didn't they Josephine? I think it's time for us to head upstairs to our private room now, don't you?"

Josephine nodded eagerly and stood up, taking her master's hand. The Central Station pub had private rooms that could be booked for couples wanting something more intimate, and given how these two had clearly agreed to meet up her in advance, it made sense that they would have booked one.

"Have fun!" was all I whispered as she was clipped back onto her leash, crumpled sundress draped over one arm, and led off to be taken by her master in private.

All alone again, I headed back to the bar, in need of more alcohol to continue my buzz, although it could hardly be said my inhibitions could be any lower. I felt an abrupt tap on my shoulder. To my surprise, it was Claudia. She was furious!

"I spend my spare time and spare makeup trying to make you look beautiful and you ruin it straight away with this mess on your face," she gestured to my running makeup and cum-drenched face.

I stammered an apology before she burst out laughing.

"I am joking, darling! I'm glad you are having fun, I am jealous, I haven't found any cock yet, I've just been hanging out round here."

Feeling much more confident than I had done an hour ago when I had descended the stairs into the basement, I did what I had done many times already that night and sunk to my knees.

"I'd like to thank you Claudia."

She scoffed when she saw what I was doing, like the idea was ridiculous.

"Darling, no one has done that for me in years. I'm the sucker, not the other way round." I gave her my best sissy pleading eyes.

"Please, otherwise how will I be able to repay you?" She rolled her eyes and looked intrigued.

"Go on then, but we can't do it here by the bar. Come with me." She led me to a similar space that I had shared with Ariel, but this time I crawled after her instead of walked which I think she found amusing.

On my knees again, I took her cocklette out from underneath her dress and tried to get it hard. Being truthful, it was only around three inches and was only semi-erect, but I wanted to please this older transsexual anyway. I think she liked just having it in her warm mouth.

"Where's Claudia got to?" I could hear voices bustling outside.

The curtain shielding us was abruptly pulled back, and two quite drunk crossdressers, both in their 50s around the same age as Claudia stood there, laughing at the scene.

"Not like you, Claudia!"

"I know but this cutesy little tart insisted after I helped her out with her makeup earlier."

"Mind if we join in?"

"I don't think she minds anything." With her cocklette still between my lips, I shook my head in agreement.

The two older ladies sidled into our private space and closed the curtain back so we were cloaked again. They were both wearing elaborate garter belts and expensive lingerie sets. I tried to suck each one for an equal amount of time, and they all helped each other with their hands. Eventually they all came to orgasm on my face, ruining the makeup Claudia had performed for me even further.

"Thank you very much, young Amy. What a polite and well-mannered sissy you are!"

I beamed at the compliment and stayed on my knees as the three of them left. I stayed in that way for a few moments, just catching my breath. The curtain rustled though and I could make out the figure of a man and a woman trying to come in. I was occupying a space that could be used to fuck, how selfish of me! I stood up and apologised, offering them the space.

In the glow of the red light, I caught a glimpse of the sissy's face and did a double take. This was no sissy. I am proud of being an utterly pathetic sissy but there's a difference between a sissy, someone who is essentially a man (a pathetic failure of a man, but a male nonetheless) who crossdresses, and a trans woman. The face before me was clearly that of a proper trans woman, not some pretender who was here just for their sexual fetish.

She seemed like she was of Latin heritage of some sort. Her hair was a chesnut brown, flowing down to the nape of her neck. Bright red lipstick and subtle eye makeup was all that she had on her naturally feminine face, not caked in powder like the three older dressers who had just left their cum on my face. If I had to guess, I would say she was early 30s. She had a denim jacket over a navy blue bra, containing her smallish boobs. Maybe a B cup and definitely real, so she was on hormones I figured.

For some reason, she seemed intrigued by me too. She was looking me up and down and seemed fascinated by me. Her male partner seemed confused, likely he had been pulled in with the promise of imminently getting his dick wet and now here I was holding up proceedings.

"Hello there. I'm Eva." Why was she even speaking to me?

"I'm Amy. Can I help you?"

"Amy, what is a passable and young woman like you doing in a place like this?"

"Um .. because I'm a sissy."

"A sissy? Isn't that a bit degrading?"

"I guess .. but I like it. The term, I mean. Although I understand that trans women aren't sissies, I know it's different and complicated." Her guy was losing patience.

"Come on baby, let's fuck, you promised."

"Hang on, I'm talking to Amy here, can't you see?" This was all such a confusing headfuck! "Amy, I think you can do much better than hanging out with the pensioners that haunt this place."

"You think?" A little rude to the wonderful femmes I had met here before, I thought.

"Put it this way. I am the only proper woman in this place. I come mainly out of nostalgia for when I used to come here when I was still a boy in drag like you are now. But you are head and shoulders above any of these unconvincing crossdressers here."

"Thank you," I spluttered, my cheeks flushed totally red.

"Let's chat and catch up. I think you have some potential that I would really like to mould. Places like this are fun for crossdressers who are getting on a bit but I could do so much more with you. Would you like a drink?"

"Yeah, I would love one."

"Look, I thought we were gonna fuck." Eva rolled her eyes and turned to her indignant partner.

"I'll fetch some drinks and in the meantime, I'm sure Amy wouldn't mind you fucking her?"

"I would be happy to let you fuck me sir."

"Good," he said, pushing past Eva and bending me over up against the wall. There was lube and condoms on a shelf above us and before long, I had my god-knows-how-many cock buried in my boi cunt again.

"Is a vodka mixer alright, Amy?" Eva asked. I grunted my thanks while he roughly fucked me, still quite unable to process this sudden turn of events.

She returned with three drinks and set them down on the shelf above us. She perched herself down on a nearby chair that I had been leaning on while this man pounded my tight hole. Crossing her legs, she took my head in my lap and slowly stroked my hair.

"Thank you Eva." I just wanted to do nothing but express gratitude to this beautiful trans woman for even noticing me.

"That's OK. Maybe you should thank Ryan here as well?

"Thank you Ryan," I squealed to the man who was currently arranging my insides with his near 8" dick.

I suspected Eva had her pick of the meat in here and she had chosen well. She was simply cradling me in her lap, stroking my head while her man destroyed my hole, which was starting to really get sore from all the action I had had tonight already.

"How would you feel about giving me some head, Amy?"

"Please .. so fucking much," was all I could get out, Ryan slamming into me making it hard to breathe.

She unzipped her short shorts and nestled them down enough to give access to her panties, without having to take my head out of her lap. The way I was positioned, it was only natural for me to slip her gorgeous veiny 6" penis into my mouth, it all just made so much sense. It fit so snugly!

I made love to Eva's cock. There was no other way to describe it. I caressed it with my tongue and rolled it softly around my mouth and did everything I could to bring this amazing woman to orgasm. When she tensed up and flooded my mouth with her juices, I felt an immense wave of satisfaction. But she was not done with me yet.

"Ryan, stand her up a bit and lean her against the wall." Ryan did as he was told, then went back to penetrating me like his little sissy whore.

Now I was against the wall, standing up straight almost instead of bent over. Ryan stayed behind me but Eva took to her knees with her face beside my little clitty. I wasn't going to argue with whatever she wanted. She took it in her delicate, feminine fingers and slowly began to pump it, with fragile flicks of her wrist. Despite myself, I couldn't stop it growing hard, against all my sissy rules.

"You haven't cum tonight have you Amy?" When I shook my head, she said, "then you deserve this! Hang on a sec!"

She reached behind her and unclasped her bra, letting free her small but perfectly formed tits. Her nipples were a dark brown but I loved the way her breasts were whiter and less tanned than the rest of her darker skinned frame. Her hand was increasing the pressure on my clitty.

"I want you to cum on these, Amy. Can you do that? Come for me while you get rammed!"

"Yes, miss!" I squealed, although I knew as soon as I came bad things would happen.

"Good girl!"

And there it was, that phrase that pushed me over the edge. Despite my reservations, I couldn't help myself twitching and letting forth a stream of cum which sprayed all over Eva's chest. And oh god, here it came, the sudden wave of sissy shame I experienced nearly every time when I orgasmed wearing women's clothing. Luckily Ryan also shot his load in me at the sight of my sissy cum running down Eva's nipples.

My whole attitude and demeanour changed to one of self loathing and panic, I just wanted to get out of there ASAP. Why had I come here, why had I done all these disgusting things? As soon as Ryan's cock slipped out of me, I stood up to leave.

"Thanks but I really have to go." Eva's face dropped.

"What? Amy, why?"

"Sorry but I really have to go, none of this is right. Please."

I think Eva knew what was up and didn't protest, but simply said this.

"OK OK but do me one favour?" When I paused, she said, "just come over here."

She took me by the hand and dragged me over to the bar. Unlike the rest of the employees, the barman seemed to be here for the money only, and wasn't exactly thrilled by all the goings on around him. As Eva pulled me over to where he was working, he looked at me with what looked like disgust. There I was standing only in purple lingerie and covered in other men's cum. It was only right he was disgusted.

"Can I have a pen, please?" Eva asked.

He reluctantly handed one over and Eva began scrawling a number on my arm.

"If you change your mind and would like to meet up, please contact this number."

I nodded and thanked her for the drink again, then went to find the rest of my clothes. I couldn't even look at her, as truly stunning as she was, I just wanted to get the hell out of there. I collected my rucksack, shut myself into a toilet on the upper level so as not to have to get changed around the other sissies, and quickly got back into my boy clothes. I washed my hands and body as much as possible in the little basin in there, just wanting to cleanse myself of what I had just done for the last two hours.

I lingered when I came to washing my arm, where Eva's number still remained. Did I want to call her? Did I want what had just happened, which I had loved so much at the time but now post-orgasm was filling me with incalculable shame, to happen again?

Out of respect for Eva, I left it for now and decided to wait till I'd slept on it whether or not I would contact her again. Here is the part of the story where I tell you in real life I never met up with Eva again. I was too scared of what it might mean.

But from now on, the next chapter will explore what would have happened if I had just taken that plunge ...