A Lady in Waiting

**Warning this story contains scenes some readers may find offensive. Discretion is advised.**

I always liked fall in Chicago. It's cold, but not freezing. There is a chill in the air and the knowledge snow is just around the corner. The leaves in the park begin to change and the colours are a beauty to behold. The trees add much needed brightness to the grey sky.

My name is Madison. I am a twenty-nine year old girl. I have always had trouble calling myself a woman. At what point do you feel grown up enough to do so? I still feel too young, I mean I don't even feel comfortable enough to send back food at a restaurant.

I work as a manager at a large company in the centre of Chicago, I'm the youngest manager at the firm and that makes a lot of people jealous. I just know how to get shit done. Too many people mess around going back and forth, but I know what I want. People often use the way I dress an excuse for my success. Perhaps they think I use my sexuality to get ahead, I guess it makes them feel better, but there is a difference between using something to advance yourself and using it to your advantage, honestly, I don't give a fuck what they think, I know I'm attractive.

I'm 5' 8" without heels. My face is soft and subtle, with defined features but not sharp. I have long natural blonde hair, piercing blue eyes with long eyelashes. I have a small cute nose, and full lips. Most of the time I wear a red lipstick to really show them off.

I work hard to keep my body in shape, I am thin but toned, only kept up by many hours at the gym, something has to relieve my stress. My breasts are a comfortable size, not so big that they look swollen, but not so small as to appear flat-chested. They are perfectly sized for a mans hand. My ass is perhaps my proudest feature. I go to spin class three times a week to keep it as firm as it is. My pussy is soft and wet. A small strip of hair sits vertically atop it. I tried shaving it all off once, but I need a little something. I have long toned legs, with a nicely developed thigh gap, I know how much that gets people going.

Working in an office, I have to dress smart and ready for business. The magic of office-dress is that no one knows what's going on underneath. It acts as a veil of mystery, a curtain that few get to peak behind. As such I love to wear lingerie underneath, no one knows that it's there except me, I feel like such a slut when I wear it at work but I love it. If only they knew what was going on, and believe me there are plenty of men that want to know.

Today was just like any other day. I had woken up and gotten dressed. I was wearing a pale pink, matching set of underwear. The thong had enough material to cover my pussy but was see through enough to show my strip. The bra, in a similar fashion, was a firm pushup, to highlight the accents of my breasts, it was also see through enough to get a glimpse at my perky nipples. As the weather had begun to turn colder, I chose to complete the set by wearing the matching suspender set. I had attached a pair of black, silk stockings. I always love the feel of them on my legs and looking at myself in full lingerie got me a little wet. I could feel the moisture build and a heat start between my legs. But I pulled myself out of it and put on a slate-grey office dress that became looser below my hips The dress stops around the middle of my thigh, just enough to cover the lace stocking tops. Finally, I put some black pointed heels and admired myself in the mirror, pleased with the professional slut that looked back at me. It's no wonder the men at the office look at me the way they do, they think I don't notice, but I do, they're not subtle. Wherever I walk, I feel their gaze on me. Mostly on my legs and ass. They all look like they want to bend me over the desk and fuck me. I know that makes a lot of women feel uncomfortable, but I don't give a fuck. Maybe I'm a bit of a slut.

I finished work late that evening. I could see from the window that it was dark and windy, the sky was filled with low clouds which made it feel more oppressive and later than it was. As I stepped outside onto the sidewalk, wrapped in my coat, I hesitated. I usually try to avoid walking through the park alone when its dark, so I turned and headed along the street, taking a slightly longer route home. The streets were quiet, but there were still people around. As I continued towards my apartment, I walked straight down a darker looking side street, I wasn't used to walking this way but as it was still in the right direction I walked on.

The street was mainly residential and was a lot quieter than the main roads. I noticed that on the other side of the street three black men were sat around chatting in front of a house. I could clearly see that they were muscular, they stopped talking as I passed by on the other side of the street. I could feel their eyes watching me as I went. I felt a little nervous and tried not to look, but my heart started beating faster. Just stay calm I told myself.

At that moment a strong gust of wind blew down the street, causing the bottom of my dress to fly up. Everything below my waist was visible, the small pink thong, my long stocking covered legs going down to my heels. I quickly pulled my dress down, but it was too late.

I heard one of the guys say, "Oh, fuck! Did you see what that slut was wearing?"

I started to walk briskly away but at that moment the three of them got up. One of them called out to me, "Hey girl, why don't you let us see what else you're hiding."

They caught up with me easily, and I stopped. My heart was pounding and my breathing was short and erratic. I tried to appear confident.

"What do you want?" I said, mustering as much strength as I could, trying to hide my fear.

"Woah, this slut's got a bit of an attitude; and you know I don't like girls with attitude," the tallest said, looking at the others.

"Well, what do you want?" I asked, a slight waiver in my voice.

"We couldn't help but see what you got underneath that dress," one of them said with a smirk as he moved his hand towards the bottom of my dress. I quickly moved backwards out of reach.

"And you know, seeing as you are clearly a naughty, little slut perhaps we could come to some kind of arrangement," the third said.

At this point, I could see what they were suggesting. A lot of thoughts crossed my mind, should I run? No they would easily catch me. Should I try and fight them off? I might be able hit one of them, but three, no chance. Okay, maybe I can just keep it light and give them a hand job, at most a blow job. If it means I can get out of here as fast as possible, I could.

"Do I have a choice?" I said weakly. I could feel my knees shake slightly and my head was light.

"Oh you always have a choice," the first laughed, "but there are good choices and bad choices, and my dick hasn't been sucked in a long time."

I swallowed. A blow job it was. Just stay calm, the important thing is not getting hurt I consoled myself.

They led me back to the house, and took me into their living room. The three of them pulled down their trousers and sat down on the sofa. I stood there in the centre of the room, in shock at the size of the black dicks that sat in front of me. I thought that I had seen a few large dicks in my time, but this was another level.

"Come on slut, don't just stand there", one of them barked.

I took a deep breath and walked over to the first one, I bent down onto my knees and took the cock in my hand. It felt strong and thick. I closed my eyes and took it in my mouth. I could barely take it all in, my mouth stretched over it, my ruby red lips contrasting again the black dick they were wrapped around. The guy moaned. I used a combination of my hand and mouth and worked into a rhythm. It was working as the guy began thrusting his hips, matching the motion of mouth.

"You can't have it yet slut", he said pulling his dick out of my mouth. He gestured to the guy sat next to him. At which point I knew it was time to move on.

I took the second dick in my mouth, it wasn't quite as thick as the previous one but it was longer. He was much rougher though and pushed my head down on his dick until I choked on it. Water filled my eyes as I gagged. As this was going on, the final guy started pulling up my dress, I tried to smack his hand away but he simply grabbed it and held it firmly. I couldn't get it free as he pulled my dress up, revealing my ass and legs. The first guy began grabbing my ass, as the other stroked my legs. It was all becoming a little overwhelming to have so many hands on my body in addition to a dick in my mouth.

"Oh shit, she's so wet! Do you like this you little slut?" the first said as he stroked my thong-covered pussy. I jerked forwards, but with nowhere to go I couldn't escape their exploratory hands. Why was I so wet? I had been so consumed by sucking the long black dick that I hadn't noticed my pussy was dripping. I felt a fire begin to burn between my legs.

The third guy sat back on the sofa and demanded his turn. I dutifully complied and took the final black cock in my mouth. This was the thickest of them all. My jaw began to ache from attempting to take it in. I tried to work my way into a rhythm as I had done for the others, but the first guy had pulled my thong to one side and was playing with my delicate, soaking pussy. Before I knew it, I felt a long wet tongue slide up my pussy. I let out a stifled shriek, but it felt good.

"Oh fuck, she tastes so good," he said as he began to eat my soft pussy and ass. The second had began grabbing at my tits. Things were escalating quickly but the feeling of the guys tongue circling and sliding up and down on my clit felt amazing. The fire that had begun, soon turned into a roaring flame and I was enjoying it. I tried hard to stop myself, this isn't what I wanted. Or was it? My body was betraying me and I soon felt waves of pleasure roll throughout my legs.

The third guy took his dick out of my mouth and looked into my eyes as I remained there on all fours in their living room, the second guy now exploring my ass with his tongue.

"We're going to fuck you now," he said purposefully, as if testing to see if he would get any objections. I remained silent. "I thought so," he said. They rearranged themselves and positioned me where they wanted me. They were too strong to resist, but I didn't put up a fight. I could feel myself succumbing to the situation.

So there I was, on all fours in the centre of the living room. My dress had been taken off and lay in a crumpled heap on the floor. My long blonde hair falling on one side of my face. My breasts were out despite my bra still being on. My thong had been pulled to the side and I still had my stockings and suspenders on, the heels remained on my feet.

One of the guys lined up behind me and I could feel the tip of long dick massaging the entrance to my delicate pussy. Another kneeled in front of me, aligning his cock with my mouth as the final guy remained next to me, exploring my body with his hands.

Without warning, the guy slid his dick into my pussy. I gasped. It was so big, I could feel it completely fill my hole. But it felt so good. The guy in front of me took the opportunity to stuff his dick in my open mouth. I gagged as I was filled from both ends. I let out a long moan, which only served to arouse them further. They began to build up a rhythm as I rocked back and forth, moaning with pleasure at every long stroke into my craving pussy. I could feel the tension build throughout my body and I felt myself thrusting back on the guys dick. Before I could come however, they stopped and rearranged. I was desperate to get filled again, and feel the stiff length of a shaft pumping my pussy.

The next guy slid underneath me as the one who had just fucked me came round to my mouth. I had never tasted my own juices before but they were much better than I expected. They tasted almost sweet. I began riding the new guy and sucking off the guy in front of me. I was lost in pleasure so didn't notice that the third guy had gone around behind me and was eyeing up my ass.

He started using his finger to massage my tight asshole, which I didn't mind, as it made me clench my pussy tighter giving me more pleasure from the long dick inside me. He then proceeded to rub the head of his dick against my hole. This made me alert. I had never taken anything up my ass before, let alone such a thick, black dick as this one. There was no way it would fit and I wasn't ready to find out. But my mouth was stuffed full of the first guy's dick and I couldn't let out a word, I could only moan.

I felt something cold hit my ass and I realised he had just poured lube on it. Within a few seconds, his dick was in. My eyes widened and suddenly I only saw stars. The feeling was that of pleasure and pain. I had a big, black cocks in my mouth, pussy and ass. I was completely filled, but the feeling of double penetration was pure ecstasy. I let out long and loud moans.

"Oh this slut is enjoying it now," the guy with his dick in my ass said. "You're gonna come for us aren't you slut. You like having a dick in your ass?"

I relinquished any kind of control I was trying to keep and let myself be taken by the waves of pleasure that rocked through my body. I came. And came again. I couldn't see, I was completely lost in the moment of being so utterly filled and satisfied. As I continued to moan, I could feel the guys begin to quicken their pace and their cocks began to pulsate. They let out their own groans as I felt ribbons of cum fill my insides. The guy with his cock in my mouth pulled out and shot a stream of come all over my face. I greeted it with an open mouth.

They all pulled out and cleaned themselves up. I rolled over and lay there on the floor of the living room, staring at the ceiling. What had just happened? What had I just done?

"Clean yourself up you naughty slut, we're done here", one of the guys said.

I wiped the come off my face and pulled on my dress. I left the house in silence and walked into the street. Tears filled my eyes, but I couldn't work out whether they were tears from pleasure or fear from what had happened. I walked down the street to continue heading home. Maybe it's an experience like that, that means I can call myself a woman.