by Lexie Ray
I chose my first upstairs customer carefully—a kindly older black gentleman with whom I felt like I had a good rapport. He always came in wearing a different suit but the same spectacles. His black hair and beard were speckled with white. Like the rest of them, he had loved my ass from the beginning, always requesting to sit in my section no matter where it was that night.
He called me beautiful, and I melted a little. He was never crude, like many of the other customers, who often liked to tell me just what they’d do to my ass if I’d only take them upstairs.
I felt that I would be safe with the man, that nothing would go wrong, and that I could easily experiment with what I wanted to be when I was around him, out of sight of the other people in the nightclub.
“Is tonight going to be the night you’re going to honor me with your company upstairs?” he asked me as I sat his martini down in front of him without spilling a drop. I was getting better and better at transporting Blue’s cocktails across the nightclub floor.
“Mr. Marshall, it would be my honor to take you upstairs,” I said, softly, making him lean closer to me to hear my words above the music.
“You’re going to have to forgive me, Miss Pumpkin,” he said. “But I thought I heard you say that you wanted to take me upstairs.”
I gave him a small, private smile. “That’s exactly what I said, Mr. Marshall. I want you.”
His elated smile squeezed my heart somehow, as if I were doing charity work. I wasn’t. I had led a number of men on for whole weeks while I was still getting used to everything and had decided to pick one so I could start earning the kind of money all the other girls always talked about.
“Why don’t you go and get Mama so we can get everything figured out,” he told me. That simple statement told me more than I think he meant it to. He had obviously done this before—paying to have sex with Mama’s girls. I’d seen newcomers to the nightclub blush and hem and haw while trying to proposition Cocoa. Mr. Marshall knew just what was required of him, and that was Mama.
Mama was easy to find in the crowded nightclub. She liked to stay near the door for most of the night greeting customers as they walked in. When she saw me coming, she grinned. She knew exactly what I was there for.
“And who’s the lucky gentleman?” Mama asked.
“Mr. Marshall,” I said, following her back to the man’s table.
“Good choice, sugar,” Mama said. “He’s a gentle soul.”
The way Mama looked at me made me a little nervous, like she knew more about me than I thought she did. She conferred with Mr. Marshall for a few minutes before she stood up, beaming. That told me that Mr. Marshall was more than prepared to part ways with a lot of money in order to be the first to enjoy my presence at the nightclub.
“Pumpkin, baby,” she began, saccharine sweet, “why don’t you show Mr. Marshall upstairs? I’d ask Cocoa to take you up there, but you’ve been around for long enough to have a handle on it, I think.”
Mama was right, even though I wasn’t sure how she knew. I knew exactly what to do and the location of everything in every room, just from observation. I knew that girls went to the bathroom before beginning their business to freshen up and to place lube in strategic places. I knew that you expected everything and nothing—it was the only way to be prepared.
Had Mama been watching me as closely as I had been watching her and the other girls?
“Right this way, Mr. Marshall,” I said, offering him my hand. He placed it gallantly on his arm and we made our way across the nightclub, heading toward the staircase that led to upstairs—upstairs and upstairs business.
Cocoa caught my eye as we walked, raising her eyebrows at my choice of first customer. My method was going to be simple, I decided. Never put myself at risk. Go after the highest-paying customers. Make it about nothing but business.
My method was my business plan. Cocoa never said no, making her one of the busiest girls on staff. But I could see her spirit eroding because of it. Cream gave it up for whomever she chose, no matter whether it was for pay or gratis. She could make a lot more money—or save herself a lot of drama—if she only stuck to business.
I watched for weeks so I could learn how to be discerning in my choices of customers and, most of all, to figure out what not to do. That’s how observation worked for me. I liked to learn from others’ mistakes so I could be assured not to make the same ones.
I felt like a lot of girls thought they couldn’t say no when they were asked for a little upstairs business. I was toeing a line in the sand on that one. If I was going to start with the upstairs stuff, I was going to be the one choosing my customers, not the other way around.
“Here we are,” I said quietly, opening a door in the long hallway. I liked this room and its shades of purple. The comforter for the bed was a richly royal affair.
“You wait here, please, Mr. Marshall,” I said, ducking into the bathroom. I stared at myself for a few moments in the mirror, my dark eyes very wide. I wheeled through a series of possibilities—should I be a sex kitten, or a Lolita? Shy or capable? Ladylike, or a whore? That one gave me a bit of pause. I was now a whore, like it or not, from any angle you looked at it. I was selling my body for sex.
I touched up my makeup with the basic set stored in the bathroom and slipped my uniform off. Mama had loved the way the skirt had looked on me when I tried it on with her. She’d swatted at my butt playfully, joking about how my “behind” was going to get me ahead in life. In addition to the uniform, she’d purchased several lingerie sets for me.
“I know that you’re not going to start right away,” Mama said, looking to head off any protests, though I hadn’t planned on making any. “But there’ll come a time when you do start, and you’ll need these.”
I was wearing one of them—a lacy duo that I thought made me look sexier than I felt. I shook out my hair and applied some lube before stepping out of the bathroom. Mr. Marshall was standing placidly by the bed, waiting patiently for me.
“Mr. Marshall,” I said, putting my hands on my hips as I walked across the room to him, accentuating each and every rock of my hips. “You don’t look very comfortable at all. How about I help you?”
“I would love that, Miss Pumpkin,” he said.
I slipped his spectacles off slowly, smiling at him and trying not to look as nervous as I felt. It was just sex—as simple as a game. I’d done it before and I could do it again. What did I ever get from Jimmy except for a pair of bruises that had only just recently faded? From this, I was getting paid.
I got the man undressed, kissing and caressing him as I did so, and laid him face down on the bed before I straddled his thighs and started massaging every inch of him. He groaned as I worked out kinks and knots, then gave small moans as I ran my fingernails lightly over his skin.
“I hope you’re going to let me repay the favor,” he said, his voice muffled by the thick pillows of the bed.
“Only if you want to, Mr. Marshall.”
When it was my turn for a massage, he paid extra special attention to my ass, which I’d expected. He gradually unhooked my bra and slipped my panties down my legs. I could feel his hard cock pressing up against my legs as he worked me up and down. I felt like putty in his hands once he was finished with me, like I’d simply ooze between his fingers if he tried to pick me up.
“Mr. Marshall,” I said, making my voice as light as possible. “I hope you won’t get angry at me.”
“Miss Pumpkin, how could I ever get angry with you?” he asked.
“I was wondering if you might put a condom on before we … do it.” I bit my lip as I sat up and looked at him, tracing abstract designs on his bare shoulders. “I just want to be careful.”
“You’re a prudent young lady, Miss Pumpkin,” he said, smiling warmly at me. “Of course I will. In fact, I always insist on using a condom.”
I smiled, the expression more genuine than I meant it to be. Rule number one. Always use a condom. I had the female contingency
to thank for that practice. If I was going to be a sex worker, I was going to be as smart as I could about it.
I hopped up from the bed and fetched the condom from the bathroom, tearing the foil and slipping the latex over Mr. Marshall’s nicely shaped dick. The old man was better endowed than Jimmy, I couldn’t help but notice.
We rested on the bed side by side, running our hands all over each other, before he positioned the head of his cock right at the opening of my pussy.
“Yes,” I breathed, trying to decide how eager I should seem. It was hard to decide on a happy medium. I consoled myself with the fact that this was my first upstairs business transaction. Mr. Marshall was sweet enough that I could test several different personas on him before I settled on my final business model.
“I only want to make you happy,” he said before plunging into my body.
The gasp I gave wasn’t fake. His cock filled me up and then some, forcing my body to make hasty adjustments to accommodate him. Our limbs got tangled up as he withdrew almost completely out of me.
“Did I go too fast?” he asked, tracing the side of my face.
“No,” I said, shaking my head and kissing the palm of his hand. “I want all of you. Please.”
“You never have to beg with me,” he said, pushing in again. I saw stars, crying out at the sensations of the position and the feeling of something I had foregone for so long. If I was being honest with myself, I missed sex. It had been a while.
In one fluid motion, I kicked my leg out and turned, his cock still inside me. We were now in a spooning position, my ass pressed up against him, which Mr. Marshall apparently enjoyed very much. He grabbed my cheeks, spread them, and pushed them back together, thrusting mightily all the while.
“Tell me you like it,” he begged. “Tell me it feels good.”
“It feels so good, Mr. Marshall,” I moaned. “Please don’t stop. It feels so amazing, Mr. Marshall. Oh, oh please. Please.”
I squeezed my legs together, increasing the pressure on my clitoris, and enjoyed the sensations that tightening my pussy afforded me. Mr. Marshall gave a strangled gasp and clutched me to him, pumping raggedly into me.
“Yes!” I cried out, aware that he was coming. “Yes! Yes!” I wasn’t coming, but he didn’t have to know that. I hadn’t been quick enough to arrange for my own orgasm.
Mr. Marshall shuddered as he pulled out. I rolled back over to face him and planted a big kiss right on his lips.
“That was wonderful,” I said, hugging him and stroking his back as we waited for our breathing to slow. It took Mr. Marshall a lot longer than me, and I wondered just how old he was.
“Miss Pumpkin, the pleasure was mine,” he said, kissing me softly.
And it was as simple as that. With each subsequent upstairs business transaction, I got better and better at what I did, became more comfortable in playing a role that I found had the most success—demure, eager to please, honest, and, above all, a lady. A lady in spite of the reality of being a whore. The customers ate it up. They could pay for freaky any time they liked, but finding a girl they could actually envision taking home to meet their parents was somehow a turn-on. I didn’t analyze it too thoroughly.
With all the money I started making, Mama made it clear that my slow start had been well worth the wait. I didn’t like the idea that I wasn’t sure how much clients were paying to sleep with me, but I’d observed one thing very clearly from the very beginning: Don’t get between Mama and her money. She didn’t like to be questioned on it, and she didn’t like to discuss her business model.
As long as I was reasonably happy and secure in the nightclub and boarding house, though, I didn’t see a problem with Mama holding my money for me. She let me have whatever amount I wanted whenever I wanted.
As girls came on after me, I was obliged to vacate Cocoa’s room. My new roommate’s name was Daisy. She was nice and easy to live with, always keeping her things neat and put away. She seemed incredibly innocent to be working at the nightclub, decorating our shared door with magazine cutouts of puppies and kittens. If I was reading a magazine and came across a picture I thought she’d like, I tore the page out and put it aside for her.
I heard that Daisy actually had a Lolita thing going on—lots of customers requested her because she seemed so innocent. I never figured out if she did it on purpose or if it was just in her nature.
Life got comfortable and business got easy. I became more and more complacent with the new normal of Mama’s nightclub and found myself thinking less and less of East Harlem and what I’d left there. Months passed.
Then, everything changed.
One night, in the club, a customer beat Cocoa nearly half to death before the bouncers could pull him off of her. I was upstairs at the time, so I missed all of it. But Cocoa’s absence was felt and there was an electric, uneasy energy among all of us girls. Mama was furious, but I didn’t know why.
At one point, she locked herself in the office and the DJ spinning that night had to tell everyone that the nightclub was closed.
I sidled up to the bar to tip Blue out and noticed that her hands were shaking terribly.
“You okay?” I asked, watching her tremble.
“Only through the grace of God,” Blue said, downing a shot and wiping her mouth with the back of her hand. “Only just barely, Pumpkin.”
“A lot of drama tonight,” I said carefully, watching Blue’s face.
“Understatement, baby.” She poured another shot and took it before capping the bottle. She held out her hand, which was shaking a little less. “That’s better.”
I counted out the bills and waited. That was a trick I’d been doing for years. If you lingered long enough around anyone who had something to say, they’d eventually say it. It took Blue all of ten seconds.
“Somebody called the cops after Cocoa got beat up,” Blue explained, wiping down the counter of the bar. “Mama can’t deal with street-level cops, especially if the media gets wind of drama here. It was tense.”
“Are we in trouble?” I asked, raising an eyebrow.
Blue shook her head. “Nope. Not from the cops, anyway.”
I waited for a whole thirty seconds before the rest of it came pouring out.
“Cocoa’s gone,” Blue said. “She jumped from the window of her bedroom. Mama was shooting at her.”
“Christ,” I said, my hand fluttering to cover my heart. Drama had been an understatement. This was a crisis, a complete upheaval.
“Stay as far away as you can from Mama,” Blue said, her trademark grin notably absent from her face. All I saw in front of me was a pale, worried girl. I much preferred the jolly Blue.
Upstairs, in the boarding house, the bathroom was trashed, stall doors and mirrors broken. There was a scorched hole in the carpet just outside the bathroom door—a bullet hole. And Cocoa’s room was empty. All of the girls looked at it, trying to puzzle out what it meant.
We should have all realized it then—it was the beginning of the end.
Mama sank into something scary. Girls were too frightened to ask her for money and started doing without—or squirreling away cash instead of giving it to Mama to hang on to. She was drunk more often than she was sober, and Mama was a dangerous drunk.
Then, Blue got pregnant.
I found stoic Blue in the middle of a panic attack in that broken bathroom. Mama wanted her to get rid of the baby, but deep down, I knew Blue didn’t want to. She put it off and put it off until she finally got the chance to leave the nightclub. Blue did it during the day, when Mama was passed out from liquor, and all the fight went out of us when she left.
Both Cocoa and Blue had been strong women. They had banded us together, made us look out for each other
I knew how to stand up for myself, but I couldn’t put it all on the line for the rest of the girls. We simply avoided Mama and did our best when it was time to work. Some of the customers even began to notice that Mama was stinking drunk when the place was open. The bartend
ers were having a hard time keeping up with the bottles she blew through.
Something drastic had to have happened. Or maybe it wasn’t drastic at all. Maybe just one person had let slip to the wrong person just what we were. Maybe one of the city’s newspapers had sent an investigative reporter to the nightclub. And maybe one of Mama’s girls—maybe even me—had taken him upstairs.
I guessed it didn’t matter what had happened. But in the middle of the day, sirens filled the boarding house and we looked out our windows to see squad cars with their lights wheeling like some blue and red cop Christmas.
“Run!” Cream had yelled, and we scattered.
Nobody left the way Cocoa had—out the window—but as we tumbled down the stairs, it became apparent that we weren’t all going to make it.
Four cops had broken down the office door and were dragging a roaring Mama out of there. The rest were flooding in, and with several shouts, saw us.
“Stay where you are!”
“Hands up!”
Those commands only made us run faster. I grabbed the girl nearest to me and hauled ass. We held hands, sprinting out the alley and down the street. It wasn’t until five blocks later, panting, that we stopped. I looked down and realized I wasn’t wearing any shoes and only had a pair of lounge pants and a tank top to my name. I was grasping someone’s hand so tight that I’d lost feeling in my own. I looked up into Cream’s eyes, whose fear I was sure was mirrored in my own.
‘What the hell just happened?” she asked breathlessly.
“It was a raid,” I said.
We looked behind us, but there weren’t any uniforms chasing us. We were, however, getting a lot of strange looks from passers-by. Cream, at least, had on jeans and a T-shirt.
“Where are we going to go?” I asked.
Cream bit her full bottom lip and I could see her searching her mind.
“Let me try to call someone,” she said. “You see a payphone anywhere?”
We found one and celebrated the fact that it still functioned in a cell phone-dominated world. None of Mama’s girls had much use for cell phones since there was a landline in the hallway. It shocked me how dependent we’d become on living there. Now that the boarding house era was through, I felt lost. That had been my home more than any place. I didn’t feel like I had the basic skills to survive.