Sweet Wednesday Ch. 01

A sissy was on her hands and knees on the leather box, both her mouth and pussy stuffed with dick. Tall men stood either side of her, shoving their cocks into her holes as fast as they possibly could and with brute force. All I could hear was their grunting and her muffled moans as she tried to breathe through her nose. About five other men, much less attractive than the young alphas doing the actual fucking, were standing around watching and playing with themselves.


On my entrance, a couple of them turned around, eyes lit up, sensing some opportunity that they may be able to get in on the action. A man old enough to be my father looked me in the eye and slowly began to walk over to me. I got the sense that no one really said much in these rooms. Men were men, here to fuck sissy holes and sissies knew their place and did as they were told. There was no need for any further communication.


As he approached, I felt a hand on my butt again. One of the men down the passage I had just come from had followed me and was trying to entice me again. A real man in front of me, a real man groping me from behind, this time I didn't try to walk away. Quite the opposite, I leant back into his touch and let his hands roam all over me. This is all I craved in life. This is what a sissy like me was built for. I shut my eyes in bliss.


When I opened them, I realised the man who had been coming towards me had backed off. Frustratingly, he was clearly jealous that he hadn't got to me first. I felt that there was more than enough of me for them to share but I didn't complain, as the strong male hand that was running up and down my body from behind took a tight hold around my neck. I felt his hardness press into my back. The white blouse I had bought wasn't the best fit, and was beginning to ride up, so I wasn't surprised when I felt the wet head of his cock press into the small of my back.


His hand snaked down further and cupped my little ballsack through my purple knickers. I recoiled instantly. For me when I'm dressed, I don't want anyone touching that. I am not a man, I'm a sissy. It should be about HIS pleasure, not mine. He sensed my discomfort and pulled away. The hypnotic feeling of being taken dissipated a bit and I felt fear and unease come back in me again.


"Um, I think I'm gonna get another drink."


"Hahaha, OK you stupid bitch. You'll be coming back for more later." His words stung but I knew it was probably true. As I was leaving, the sissy getting fucked must have stopped her cocksucking for now as she had begun to scream as she was pounded.


"Fuck me like a worthless bitch!"


I must have taken a wrong turn in the darkness as I came out in a different spot I didn't recognise. In a little corner of the basement, there was a large barrel, meant for people to stand around and place their drinks on. But slumped across it was a crossdresser who must have been at least 60, with what can only be described as stereotypically poor and over the top crossdresser makeup. Behind her, a young black man had two strong hands on her hips and was fucking her like his life depended on it. She was clearly intoxicated in some way, her eyes rolling into the back of her head. The black shawls that covered her body were covered in some kind of liquid I dared not to think about, yet I couldn't look away.


Her glazed expression changed when she spotted me and we made eye contact for quite some time. She didn't say anything, just looked into my eyes soulfully as the young cock was rammed down here. Who knows how many times she had been fucked in her long life, but she was clearly no newcomer to this. This was a sissy who had probably come here for years, resigned to her fate as a worthless pathetic failure of a man who could only find happiness by putting on women's clothes that looked ridiculous and getting fucked by much younger men. Yet again, I wondered would this be me when I was older? The idea terrified me as much as it turned me on. I could feel nothing but sadness for this person but knew I was doing everything I could to become her and part of me didn't want to stop.


'You wanna be next?' the young man ploughing her from behind asked.


I didn't know what to say. As I was thinking how to reply, the old sissy stretched up her hand and tried to grab at my crotch.


"Suck ... you...," she slurred.


God knows what she was taken. Maybe she was just addicted to cock. I really wasn't enjoying this, this possible glimpse into my future, and I turned on my heels and headed back to the bar, back into a slightly more normal setting. Here, tgirls were chatting and laughing and the moans coming from the darkrooms were less audible. Again, my eyes were drawn to the dresser in the white sundress and the empty seat next to her.


"Mind if I?"


She shook her head and I daintily sat down next to her, and crossed my legs with my G&T cradled in my lap. She piped up in a squeaky voice that was clearly put on.


"Josephine. My name is Josephine."


"I'm Amy. Can I just say I love your collar?" She blushed and looked genuinely delighted by my compliment and seemed to open up a little bit.


"Thank you! I haven't seen you around. Have you been here before?"


"It's my first time," I admitted. "How about you?"


"I come here all the time. To be honest, it's the only place I feel like myself." When she admitted that to me, I felt such a sense of solidarity with her.


"I know exactly how you feel. This is actually the first time I've ever been dressed up in public. I need to get a wig and learn how to do my makeup though."


"I think it looks good!"


"Another lady did it. I could never have done this. I'm new to being a sissy."


"Well you've probably come to the right place. Did you like it in there?" We both looked beyond the black curtain.


"It was pretty intense ... but yes. I loved being groped. But I don't want them to touch my ... you know ... I'm not a man...,"


"We're not men, we're sissies," she finished my sentence for me.


"Exactly!" Josephine got it.


She raised herself up slightly off her chair and reached down to pull up her dress. Underneath it spilled white lace petticoats, which she pulled back further as well, to reveal something I'd never seen before. Tucked in between her legs was a pink plastic device, what I now know to be a chastity cage. These days I wear a chastity cage permanently, but ten years ago this was my first experience ever seeing one. Josephine smiled at me.


"I'm all locked up! That way boys know not to touch it." I could only marvel, completely jealous.


"Does it not hurt?"


"It can get a little uncomfortable, particularly when I feel super girly and get turned on. But a sissy knows her place and her place is in chastity."


I had so many questions for my new sissy sister, when I heard a whistle. A stocky bearded man had just walked in through the red curtain. Josephine looked up at once and shot out of her chair and straight over to him. In his burly hands, he was carrying a black dog leash which he clipped into Josephine's collar. They clearly knew each other very well. Before I even had time to say goodbye, he was pulling her off past the black curtain and into the sex dungeon beyond. I was sad to lose her company but happy she was about to get the fucking I knew she probably craved.


Time for another drink, I had raced through the first. As I ordered, I tried to lean against the bar in what I thought was the most sultry, sissy way possible. While I waited for my drink, two very tall crossdressers came and stood at the bar next to me. Both of them were East Asian, Filipina if I had to guess, and dressed almost identically in tight leopard print pencil skirts and black lacy see through tops. Their bras were full, stuffed or real, I couldn't tell and their long silky black hair came down to their shoulders. They were chatting to each other when they spotted me.


'Hello, cutie!" said one, as she walked around to the other side of me, so that one of them flanked me on each side. "How are you?"


"I'm okay ..." I had no idea how to flirt, I just wanted these women to keep talking to me.


Luckily it didn't seem like I had to do much to keep their attention as I felt one of their hands grasp me through my short shorts, while the other eased a hand over my shoulder and pulled me in tight.


"I love little girls like you, you utter cutie. Would you like to play with us?" All I could do was gulp and nod.


"Mmm, that's a good girl. Do you like other girls?"


"Um, I dunno, I've only ever been with a couple of guys."


"Well don't worry, I still have a lovely cock for you to enjoy. I'm Ariel."


"That's such a pretty name," was all I could manage to reply to her as she pulled me in closer to her and kept whispering to me.


"Let's go in there."


I was completely folded into her body now and she was taller than me so I fit in nicely. Her friend has stopped feeling my shorts and was talking to a man who had started chatting her up at the bat next to her.


"Are you coming?" Ariel asked her friend. She shook her head.


"Nah huh, Ariel, you have your fun with the little girl. I want a real man." Her partner at the bar laughed. The humiliation got me twitching.


"More for me," Ariel said and began leading me into the dark red space.


"Let's find somewhere just for us, baby."


"OK Ariel," I replied, glad to maybe start slow away from the prying eyes of all the random men huddled in the darkness.


We found an area that was away from plain sight, one of the black wall curtains shielding us from view. She pushed me in and then pulled it shut behind me. Just me and this beautiful crossdresser alone.


"Unzip me, baby," she said turning around, showing me her ass and thrusting it out for me to unzip her from behind.


Instinctively, I fell to my knees. My hands found her body in the low light and gently pulled down her skirt, past her tights. She stepped out of them and turned around to face me. Black satin panties stared back at me with a hard bulge poking out. It was the only giveaway of her secret. Everything else looked so real, so feminine, I was in the presence of a goddess. Her hands stroked my hair as she looked down at me.


"Does my little girl have a name?"


"Amy... miss. Sissy Amy."


"Miss? I like that. Have you sucked cock before, Amy?" I nodded and she stroked my hair gently again. "Good girl. What about lipstick? Have you put on lipstick?"


As she said it, one hand came away from my hair and down to her waistband to gently free her cock, which sprung out. It wasn't big, maybe four inches hard, but it was thick and rock hard, with an asymmetrical curve. I licked my lips, so beautiful was it. It fit her frame perfectly.


"Do you like my lipstick?"


"Yes, miss."


"Why don't you show me how much you like it and put some lipstick on, baby?"


I leaned forward ever so slightly and slid her small shecock into my mouth. Already wet with precum, it glided in and I was able to take all of Ariel in one go. No one had ever performed this on me before, but I knew what the previous guys I had hooked up with had liked. Starting slow, I lubricated my mouth with as much spit as I could to really cover her cock. She liked that, it seemed from her soft purring.


"I can tell you've done this before. Good girl." She was back to stroking my hair again now.


I bobbed gently up and down on her smaller meat, loving the smell coming off it and the way it so easily slipped down my throat. I could do this for hours, in my natural place on my knees. I rolled my tongue over her head and she gasped. I knew cocksucking was a talent of mine, one I have only honed further in the years since, but I was pretty good from the start. A natural sissy, if you will.


My hand reached up and cupped her balls gently, eliciting more moans. They felt so warm and cute in my hands. The four other guys I had hooked up with earlier that summer had all had big manly sacks, whereas Ariel's was dainty as you would expect from a tgirl. Still, I knew they were full of juicy cum, cum that I was going to milk out of her. She was getting closer and closer.


"That's so so good, Amy. You're such a good girl."


Girl. I'm a good girl. A girl. Good girl. Those words kept ringing in my brain. Here was the feminisation validation I so desperately needed, the reason I forced my male body into delicate lingerie and embarrassed myself like this. It was deliciously humiliating, and just made me suck harder, so intent on making my lover shoot her load in my mouth.


"Where do you want my cum, baby?" I had a split second to decide, Ariel's cock was throbbing.


"My face!" I decided impulsively.


With no time to shut my eyes even, ropes of thick white cum shot out of her shecock and landed all over my pretty made-up face. Cum hit my eye, my nostrils, ran down my face, hot and sticky and dribbled over my lips. My tongue hungrily shot out to catch what I could. When I prised my eyes open, Ariel was looking down at me, a smirk on her face mixed with a look of gentle satisfaction.


"That was wonderful, Amy. Would you like me to return the favour?" I shook my head, wiping cum out of my eye.


"No, thank you miss. I'm not super into being touched when I'm being a sissy and pleasing men."


"Amy, I'm offended. Do I look like a man?"


"No, Ariel, absolutely not! Sorry I didn't mean it like that!"


"Don't worry, I know what you meant. Stand up baby, and just stand still. We're two girls, this is different."


I stood facing her and she took an inch step in closer towards me, just close enough to pull me in for a soft lingering kiss. Her tongue in my mouth, she must have been able to taste her own delicious cum. It didn't seem to bother her, she just kept kissing me so softly. Then I felt her hand reach around my little clitty. She brought my soft cock next to hers and held them together in one palm. Two soft little cocklettes rubbing next to each other, ever so softly, ever so gently.


"See how it's different when it's just us girls?" She said, pulling away from my lips.


"It's lovely, miss. Thank you for making me feel so at ease. It's my first time here, and I don't really know how to start stuff so thank you for initiating me."


"Want to go find some real cock with me?"


"I would love that, miss."


She took my hand and led me back to the red space with the leather boxes. A lot had changed since I was last there. The sissy who had been in there taking a pounding before was now slumped in a corner, coated in cum and lightly stroking her cock, her tartan skirt pulled up to her waist. There were more girls either standing around with men, or paying attention to their cocks in some way, and there were still plenty of solo men standing around gawping. On one of the boxes, Ariel's Filipina friend was laying on her back, legs in the air while a broad-shouldered man with red hair and a long, thin cock slowly slid his length in and out of her boi cunt. She was moaning under her breath with her eyes closed.


"Enjoying yourself, Angel?"


Angel, which I clocked was the friend's name, kept her eyes closed and simply nodded, completely content with how her hole was being filled right now. I wanted that feeling. I had only been fucked on two separate occasions so far, and my body was still in that phase of breaking in where there was still some pain but the pleasure was starting to come in. I wanted another cock inside me, stretching my sissy hole and draining any masculinity left in me.


Ariel walked over to one of the unoccupied leather boxes and sat down, patting the space beside her for me to join. I duly obliged and looked around at the crowd of men that was beginning to fill into the space, eyeing up these two crossdressers hungrily. I didn't know what was going to happen next, when Ariel squeezed my hand and reassured me.


"It'll be okay baby, just go with the flow. I'll be right here next to you."


She whipped her top over her head and threw it over into a corner of the room, exposing her chest. I could see they were breast-forms after all, but they still looked good, tucked away behind a red bra. I wish I had any tits to speak of, but I hadn't worked up to that yet. I decided to do the same and unbuttoned my blouse. Ariel looked at my purple bra approvingly.


A ring of men, all with their hard dicks hanging out, had formed around us. Ariel took two of them in her hands and began to stroke them. Following her lead, my hands reached out and found two welcome cocks waiting, hot and throbbing. Real men's phalluses, nothing like my little cocklette, Josephine's caged thing or Ariel's cute shecock. The one in my right hand was particularly nice, a very manageable 7 inches with a lovely girth. I couldn't resist bending forward to suck it past my lips and into my hungry sissy mouth, all while maintaining the pressure on the cock I was pumping with my left hand. My right hand came free as I began to suck and I felt another firm, hairy hand grab hold of my wrist tightly and place it over a new dick. Looking up as best as I could, I saw it belonged to the black man who had been pummelling the old, dishevelled crossdresser earlier.


With these three cocks to service, I set about sucking and wanking each of them in turn. They formed an easy rhythm, swapping places to allow me access to their delicious members. Ariel had been doing the same, until I heard a commotion behind me and saw she was repositioning herself on all fours on the box next to me.


"Come and join me baby. Line up next to me."


I did as I was told and crawled onto all fours, and got onto my haunches so I was parallel to her. My three lovers understood the deal and walked to the back of us, as did the men Ariel had been pleasuring.


"Rubber up, boys. Amy is new here and I don't want her to think we're not safe." She took my right hand in her left and squeezed it. "Are you okay, baby?"


"This is amazing. I can't believe this is happening."


A pair of hands placed themselves on my hips, lube was applied to my little hole and I felt one of my lovers begin to pry with his wrapped up dick. Which one it was I had no clue, I didn't even know their names. Ariel sighed with satisfaction as her man eased into her, her sphincter clearly not as tight as my almost virginal one.


"Are you a virgin?" The man grunted behind me.


"Not really, but I've not been fucked many times," was my truthful answer. He promised to go slow at first.


"Amy?"


I turned to look at Ariel and even though she was bouncing back and forth slowly with the force of her fucking, we managed to lock lips and share another kiss. Two sissies on all fours snowballing while two alphas began to take them from behind. It hurt for the first five minutes but I clenched my body and rode out the pain and soon the rock-hard cock in my ass was stretching me out and making me squeal. Ariel was getting a considerably rougher pounding next to me. Angel, her friend, rolled her neck to the side and blew a kiss at Ariel who returned the favour. The redhead fucking her continued his slow and deep thrusts into her.


"Swap with me."


The cock that was filling me up so nicely and making me feel so complete was suddenly removed and instantly replaced by a different but no less nice phallus, shorter but thicker. My purple panties had been pushed to the side to allow my masters better access to me. I was probably fucked like that for about fifteen minutes, each man queuing up behind me waiting to take a turn, when I saw Josephine again. Her master was leading her along with his leash and she was tiptoeing along behind him. He was a confident guy you could tell her, clearly so pleased to have this sissy on a chain to show off.


"I'm going for a drink. I'm going to leave this sissy here and when I come back I want my pansy princess covered in as much cum as humanly possible. Think that will be a problem?"