2
CASSANDRA
America had weird issues with prostitution.
I mean, I guess I understood it in broad strokes. The stereotypical prostitute was a scrawny homeless woman in a tube top with track marks on her arms and half her teeth missing. Someone who had no other options in life but to have sex for money, and who was beholden to her pimp’s demands. Someone who had to sell their body out of desperation, because the system had failed them, and because the alternative was to starve and die.
But I was an educated adult. I had a Master’s Degree for crying out loud, and a thriving career. I had options in life. I didn’t have to sleep with strangers for money. I chose to, with full informed consent. I got as much out of it as they did, my recruiter ensured all applicants were clean of STDs and had nothing suspicious on their background checks.
I was a high-end escort in the 3rd largest city in America, and I loved it.
What was so bad about that?
I swung by the dry cleaners to pick up my favorite cocktail dress: it was cream-colored and covered with black lace in floral designs, and hung off my arms in a way that accentuated my shoulders. Not only that, but it fit me the way most dresses didn’t.
I was curvaceous. Not large, but I had a lot of shape to me. Wide hips and an ass I was proud of, which I kept looking the way it did every week at the gym. An ass that NBA players wanted to be smothered under.
Which meant when I found a dress I loved, I took care of it like it was my pet.
Once I had that I Uber’d home to the high-rise apartment in the Museum district of Chicago. With my dual salaries I could afford something more luxurious, but I loved my little one bedroom in the middle of the city. I hung my dress on the door frame, turned Spotify to a classical piano station, and began my routine.
I loved my little ceremony. A coronation all for me. A long bath with lavender oil, taking the time to condition and then shampoo my hair. Shaving my legs and trimming my pubic hair. Rubbing coconut oil lotion over my arms and legs while my black hair dried naturally, then blow-drying the last bits of wetness away. I was lucky to have gotten my silky hair from my mom, because once it was dried I didn’t need to put much in the way of hair products into it to get it just the way I wanted.
Picking underwear took 15 minutes. Most men were visually stimulated; the wrapping paper was just as important as the present itself. Imagining Miguel’s tastes, I settled on a lacy red thong and matching bra.
And then I was sliding into my dress, using a nifty hook tool I’d bought on Amazon to reach behind me and pull up the zipper. I had plenty of time, so I tried on four different pairs of heels before settling on the glossy black pumps.
I looked good. I felt good.
I grabbed my heavy clutch and took a deep breath, ready for another adventure of a weekend.
The meeting place selected for us was the lobby bar of the Omni Hotel, one of five locations my recruiter rotated through. The moment I stepped through the door the manager was there, a clean-cut black man with an easy smile but sharp eyes.
“Welcome back, Ms. Kim,” he said with a knowing look. “Please let me know if there’s anything I can do for you.”
I thanked him and continued toward the lobby bar, giving the bartender a nod of acknowledgment. It was always nice to know I had backup in case the meeting went poorly; one signal and either of these men would be there in seconds. It was rare, but did happen occasionally. Again, you could never be too careful. The weight in my clutch was a reminder of that.
I stopped in the middle of the lobby.
He was already waiting, even though I was half an hour early. Miguel Rojas sat in one of the plush chairs facing diagonally away from me. He was dressed in a perfect-fitting suit with the top two buttons of his shirt undone, and one leg was crossed over the other with his hands interlocked over the knee. I felt my breath halt in my lungs; he was even more handsome in person, with skin like smoked wood and a subtle thickness beneath his suit that spoke of unseen muscle. His jawline was hard as his gaze moved across the lobby, searching.
This was the first time someone had ever beaten me here. I wasn’t sure what to think about that.
And then he saw me; his eyes locked on like magnets snapping into place, surprise and then realization. They widened almost imperceptibly as he took me in, all of me, toes to my crown.
I always felt a burst of excitement and danger at the beginning, in this very moment where we identified each other. You never knew how it was going to go, like a normal date but with the intensity dialed up to 11. Every night may have been prearranged, but always a unique little adventure.
That’s why I did it. Not the huge sums of cash, or being wined and dined and taken to fancy events. I did it for the thrill. The same reason a kleptomaniac stole a stick of gum from the convenience store.
Okay, so it was a little different than that. But still.
I resumed breathing and strode the rest of the way into the lobby bar. My date rose and smoothed out his suit with large hands, and gave a nervous smile.
“Nice to meet you, Miguel,” I said, embracing him and giving a polite kiss on the cheek. His cologne was spicy with cloves.
“I… nice to meet you too.” He hesitated a moment when I said his name, which meant it was a fake one. Not unusual at all. Especially for someone who looked nervous; the ring of moisture on the table next to him meant he’d come early to get some liquid courage. “How are you, Cassandra?”
Sweat was beaded at his temples, and he gave an awkward smile. The juxtaposition of his boyish nervousness on a body so solid and masculine was adorable.
“You can call me Cassie,” I said, taking the seat across from him and giving a warm smile. “And I’m wonderful.”
I raised a finger to the bartender, who nodded and began making my drink. He knew what I liked.
“You’re… gorgeous,” Miguel said.
“Thank you,” I said, “but I doubt you would be here if I were homely.” I gave him a wink to know I was joking.
“No, I mean…” he struggled. “I didn’t get to see, ahh…”
I stiffened with realization. “Someone recommended you to me?”
“Yeah. Well. I mean, he told me what you looked like, but words are only…”
This happened sometimes. Someone would apply for their friend, whether for a bachelor party or birthday or any other special occasion. Sometimes a rich father would splurge for his spoiled son on his 18th birthday. As if that was attractive to a woman. Ugh. My recruiter knew to filter those kinds of clients out before they ever got to me.
It usually pissed me off. I wanted my applicants to want me, to have chosen me, overwhelmed by a primal lust as old as mankind itself. I didn’t like being set up for what was essentially an expensive blind date.
But I didn’t feel that way tonight.
There was a kindness in Miguel’s eyes to go with the way he looked at me now; desperate to feast on how I looked in my dress, but too polite to overtly stare. He wanted me; I could feel his desire rolling off him like waves. And I’d chosen him for a reason. I didn’t want to back out now, and it had nothing to do with the money.
The bartender appeared with my drink: a caipirinha in a short tumbler with four lime wedges at the bottom. I accepted it with a smile and then he turned to Miguel.
“Uhh,” Miguel blinked in surprise. “Yeah, make it two.”
I leaned forward with a polite smile. “You don’t need to order the same thing as me. Not everyone likes a caipirinha.” Sweet and tart like a whiskey sour, I’d never seen anyone outside of America order one.
A funny grin spread across Miguel’s face, revealing a row of pristine white teeth. “When I said make it two, I meant for me. I already had one before you got here.” He held up a palm. “I swear. You can ask the bartender if you don’t believe me.”
I arched an eyebrow, but said nothing as the bartender returned with his drink. That was one hell of a coincidence.
“My grandfather used to love them,” Miguel said after taking a sip. “When he was done I would take the empty glass and smell the limes. The taste reminds me of being a boy.”
The reason was so close to my own that the air almost left my lungs. I got a hold of myself and leaned forward to touch my glass to his. “To an exciting weekend.”
His nervous smile returned as he took another drink.
“Tell me about yourself,” I said. “You’re an investment manager?”
“Technically yes,” he said, gesturing with his glass. “But mostly I’m a cryptocurrency trader now.”
“Cryptocurrency? Like, Bitcoin?”
“You mean you don’t know?” Miguel cocked his head.
“Why do you say it like that?”
“Well, on account of… you know. The payment…”
I realized what he meant. “Oh, I see the confusion. I don’t manage any of the… transactions of the arrangement. That’s all handled elsewhere.”
“Oh.” He seemed disappointed that we didn’t have the common topic to discuss, but then his face lit up anyways. “But yeah, I’m a crypto trader. Buying and selling, like a day-trader with stocks. It’s not just Bitcoin: there are thousands of other digital currencies out there, and it’s an art to pick which ones to hold and which to sell.”
“That’s fascinating,” I said. Small talk always helped clients relax at the beginning. “How long have you been doing that?”
“Oh, five years now. I was an investment manager for a big firm before that, then got into the crypto game hard. When my company wouldn’t let me add cryptocurrency to our clients’ portfolios I quit my job and started my own small firm. It’s done pretty well thanks to the crypto bubble.” He bobbed his head. “Pretty well.”
He stared off, and I could see the nervousness falling back across his face.
“So what do you want to do this weekend?” I asked, gazing at him across the top of my glass.
“Yeah…” he began. “I don’t know.”
“Oh, I think you do,” I smiled.
He ran his free hand over his head, wiping away sweat. He was terrified! It was adorable, in its own sexy way. And the knowledge that I could make such a tall, strong man so nervous filled me with my own pleasure.
“Here’s what I think we should do,” I said, downing the rest of my drink.
*
I led Miguel by the hand toward the elevators.
My recruiter always booked the same room for me, and I had the key waiting in my clutch. Such an arrangement removed the awkwardness of needing to check-in at the beginning of the night; nothing killed the mood as much as standing around while a desk clerk confirmed your reservation information.
After two years, I was experienced with this sort of thing. Men came in all different flavors; some were cocky and confident when faced with a new experience, who I preferred to tease and hint and draw out our night before fucking their brains out. But more men were nervous of the unknown, anxious to see what would happen during our date. I’d learned that sometimes it was best to break the ice immediately, get that out of the way quickly, so you could relax and enjoy the rest of the night.
And that’s exactly what I was going to do with Miguel.
The moment the elevator doors closed, I pressed him up against the wall and pulled his face down to mine. I kissed him softly, letting my thick lips press into his in a long caress of a kiss, running my hand across his neck. He responded by grabbing my waist, then sliding his hands across my ass, grabbing two handfuls like a man grasping for a life saver. I pushed my tongue into his mouth, tasting the ghost of the caipirinha on his own tongue, sweet and tart and fruity.
The door opened on the 44th floor, and I took him by the hand once again.
“Maybe we should…” he began, but I spun around and put a finger to my lips.
“Shh, just trust me.” God, the way he moved in that suit made me tingle; I couldn’t wait to get his clothes off and touch the muscle underneath, feel them pressed against my body. I was going to fuck the nervousness out of his gorgeous body. Make him more confident, the way he wanted to be.
I stopped at the door to my usual room, slipped two fingers into my clutch to grab the key, and opened it.
The suite was a split-level, with a couch and TV in the entrance level and with two steps leading down to the bedroom area. The curtains were drawn to display the beautifully illuminated Chicago skyline, tall skyscrapers glowing with a thousand lights through the lingering night clouds.
I let go of Miguel’s hand and strode across the room slowly and deliberately, popping my ass like a runway model. I stopped when I reached the bed, and I bent over it and stretched my back like a lazy cat.
“Wow,” Miguel said, and whether he meant me or the Chicago view I didn’t know.
I turned around and sat on the edge of the bed with my arms behind me. “Why don’t you come over here and let me give you a pre-dinner treat?”
He still stood by the door, a dark sentinel whose expression I couldn’t discern. “I wanted to talk to you.”
“We have all night to talk,” I purred, beckoning him with a finger. God, I wanted him. “Why don’t you come here and let me remove all thought from your head?”
He moved slowly, cautiously, long legs striding across the room. His delay drove me wild. Fuck, who was the one teasing who, here?
“Maybe we should get to know each other,” he said, shoes clicking on the wooden steps as he joined me in the bedroom. “There are some… things, I wanted to talk about…”
“It looks like you want to do more than just talk.” I reached out and touched the front of his dress pants, running my fingers against the outline of his stiff cock. Good lord, he was big. I bit my lip and looked up at him through my eyelashes.
“Oh baby, do I,” he began. “But I wanted to tell you—”
I unzipped his pants slowly, letting the zipper click on each of the teeth individually. I slid my hand inside and pulled his cock through the hole in his boxer briefs, eight inches of it, hot and hard and juicy.
“Ohh,” I gasped, my reaction completely genuine. There was something special about seeing a man’s dick for the first time. “You wanted to tell me how big it was?”
He answered with a moan as I ran my nail along the underside of the shaft.
“I know what you want,” I said.
Pleasing men was something I loved. It was my passion. I had a variety of tools in my metaphorical box, and choosing which one to use at any given time was an art. A symphony of flesh, segueing from prelude to rhapsody to sonata, our bodies in perfect harmony. I enjoyed the power of it. I was a beautiful woman, I got to choose which men got to enjoy my company for a weekend, and then I made them cum so hard they saw stars.
I didn’t just want to give these men a fun weekend. I wanted to be the best fuck of their lives, something that gave them a hard-on decades from now just from memory alone.
I moved my head toward Miguel’s cock gradually, tenderly kissing the tip. Slowly I parted my thick lips, wrapping them around his head one millimeter at a time. I felt his entire body stiffen, and then relax, as I moved my lips down his shaft, never stopping, taking almost ever inch of him deep in my throat.
I held him there a moment, my lips brushing against his dress pants, before pulling back just as slowly.
“Oh fuck!” he gasped, voice dripping with lust. “Oh my God, you feel amazing…”
I put my hands on his hips, feeling something in his left pocket—vibrating, like a cell phone, but I was too focused on his meat to care. I deep-throated him again, feeling his long snake fill my mouth and throat. God, I loved that I could do this to a man, even someone as long as him: take all of them in my mouth, make their cock disappear inside. Sometimes this opening salvo made men cum within seconds, which made me tingle with smug satisfaction. Miguel would need more, though. I could tell.
I blew him for another sensual minute before finally pulling his cock all the way out. I gave the head another little farewell kiss and then rose.
“Let’s get these clothes off.”
I kissed him on the lips while unbuttoning his shirt one button at a time, then pulled it and the jacket off his back, revealing a broad chest lined with shadowy muscles. My imagination hadn’t failed me: his torso was perfectly V-shaped, with wide shoulders and a broad chest narrowing down to a slender waist like a goddamn plastic action figure. I broke our kiss to admire him, then moved my lips to his neck, then chest, good lord he tasted so good, and from his groans he was enjoying it just as much.
My fingers found his belt and ripped it away, then let his pants and boxer briefs fall to the floor. For a moment he stood before me, strong thighs spread wide, and I felt a tingle in my loins that could not delay.
I spun him around and sat him on the bed, his nude body bouncing on the soft mattress. Teasingly, I pulled my dress up over my hips to reveal the lacy red thong. He drank the sight of me, devouring me with his eyes, and his response pulled a moan from my throat.
I could tell he was an ass man; the way he’d grabbed my cheeks in the elevator, and how he hadn’t gawked at my ample cleavage in the lobby or since then. Excellent; my favorite kind of man. Keeping my dress above my waist, I turned around and bent over slowly, giving him a long view. And then I threaded my fingers into the string and pulled down the thong, over my thighs, then knees and ankles, and I stepped out of them and tossed them aside.
“You like what you see?” I asked, glancing back.
Before he could answer I lowered myself onto his cock, letting it brush against my dripping lips. But then I moved forward and pushed it back, wedging his cock against his belly. Up and down I moved, giving him a lap dance while his cock rubbed between my ample ass cheeks. He let out a noise like a wolf, an animal-like growl filled with desire, and when I glanced back at him I could see the need in his eyes.
Yeah. I knew what he wanted alright.
And I wanted the same thing just as much.
I squatted off of him until his cock fell forward, brushing against my lips again. I reached underneath and ran my nails along his shaft again, then guided him between my lips, back and forth to coat him in my juices. And then I leaned into him, forcing the tip of his cock up inside of my pussy. We gasped as one, each of us surprised and amazed by the feeling, and urged on by the sensation I pushed farther, two inches, then three, and I was so wet that I didn’t need to slow as I pushed all the way down onto him and took every inch.
“Oh Cassie!” he breathed, running a hand along my spine, skin touching my skin.
“Grab my ass,” I commanded, knowing it was what he wanted. His long fingers palmed my cheeks, fingers sliding underneath to squeeze the muscle tight. “Harder.”
He obeyed, fingers tightening on my cheeks desperately.
“That’s it,” I said, using my thighs to squat off of him. We had a long weekend ahead of us; I decided I wanted to make him cum quickly, and save the slower, more passionate fucking for later. I rose halfway off his long member and pushed back down, feeling his girth widening me, filling every nook and cranny inside of me, all my walls, and I didn’t stop until my ass pressed hard against his thighs and I heard him groan again.
“I’ve been thinking about you all day,” I said, letting my head hang down as I rode him up and down. “The way you taste. The hard muscle. The enormous cock, deep inside me. Ohh…”
He was groaning with each pump now, and thrusting up into me. I had him right where I wanted him.
“Ohh, I want you to cum so bad,” I moaned, pleasure cascading through me with each stroke.
“I’m close,” he gasped, fingers gripping my ass so tight he might take a chunk with him.
His sounds of pleasure rose gradually, building toward the inevitable climax. I savored the sounds and my own pleasure until I sensed he was right on the edge, and then I pulled off of him and reached back to grab his cock.
“Cum on my ass,” I said, stroking him quickly. His mouth opened and a deep roar came out. His member spasmed in my fingers and then I felt his hot loads splatter against my back, each one a drum-beat of this man’s ecstasy, who I could get off after only a few minutes, and the thought and feeling filled me with a satisfaction as deep and powerful as his strokes had.
When he was spent, I turned around and bent over him, kissing him long and passionately. I broke it away and looked deep into his eyes while our faces were only inches apart.
“We’re going to have a fun weekend,” I said, then got up to go to the bathroom.
“Ohh yeah, I can feel it,” he said, strangely distant.
“I felt it too, baby. We’re going to feel a lot more of that before the night is done.”
“No, not that,” he said, breathing heavily. “It’s… well. It’s what I wanted to tell you about.”
I paused in the bathroom door and turned around. “What is it, Miguel?”
“First of all, Miguel is a fake name. My real name is Orlando.” He gave an awkward grin and put a hand on his chest. “And I think I have something to show you. But it might freak you out.”