Can Dating a Hooker Lead to a More Serious Relationship?

There was a knock at the door. He could already hear the boisterousness of his upstairs neighbor’s friends’ voices.

“I hate her,” he thought to himself.

She was always having company over for parties. It seemed like they came over every weekend, without fail, and on some weeknights. They all wore combat boots, golf cleats, tap shoes. They never sat down. They just stomped back and forth like elephants. To the fridge, to the bathroom, back to the fridge. It was annoying.

            It was also a sickening envy he felt. And more often than not he spent those nights alone, in the dark, playing computer games or watching T.V.  It was almost impossible for him to enjoy being home from his shitty job downtown with that constant distraction upstairs. It had been the same since he moved in a year and a half ago. The first time he met Julie was in the elevator of their building. He held the door for her. He attempted to introduce himself but failed to impress anything on her besides the fact that he lived downstairs from her. There was no connection.

            He’d always hear her upstairs with whichever lucky guest she chose to keep her warm that night- skin slapping, bed springs squeaking, headboard banging against the wall- and he’d be alone. It seemed to him that she picked her partners like a kid bobbing for apples with their eyes closed, face plunged deep into wetness, trying to sink her teeth in and come up with something- someone- before her breath ran out.

“There must be a shortage of something up there,” he mused, “but it ain’t oxygen.”

            It wasn’t purely a ‘why not me?’ kind of jealousy that smothered him, though it was rubbed in his face once or twice a week with a thunderous roar. It was so much more than that. It was loneliness. And depression. Maybe something mommy or daddy did a long time ago that made it too difficult for him to connect to women. Or it may have had roots in some kind of misogynistic resentment about how much easier it seemed for women to get laid than men. Or maybe he was just plain crazy in love with the mere thought of Julie.

            She opened the door and within ten seconds the stereo came on. The wooden floor barely muffled out the music. He could still hear bass and an electronic beat. It sounded like 12 people slam-dancing to Ice Cube.

            “Oh no, not tonight,” he said aloud. There was no way he could go through another night of listening to his upstairs neighbor’s post-party sexual adventures. Tonight, he would give her a run for her money. He went to his desk, pulled out the Yellow Pages, thinking of what phraseology “date” or “companion” might be listed under. Then he remembered. He thumbed to the letter “E” where he found numerous pages with ads for “Escort Services.”

            He found an ad that took up about a quarter of the page and called the number. An exaggeratedly breathy voice answered the phone,

“Good evening, this is Kitty. Can I help you?” she asked. Perfect, he thought.

“Well hello, Kitty,” he said, his mind flashing to a white cartoon cat with a pink bow attached to the top of its head somehow.

“Hi, handsome. What’s your name?” The voice was all air.

“Um…Richard,” he said.

“Richard, huh? Can I call you Dick?” Kitty asked, snickering. Her act was faltering. That giggle alone let Richard know that she was probably pretty young, inexperienced, and obviously disguising her voice.

“Listen, Kitty: I was wondering if you were free tonight.”

“Well, I’m not free, Dick, but I am available,” she answered.

“Oh, sure. Poor choice of words. Well, whatever you want to call it… I’d really like it if you came over. What am I looking at for all night?”

“All night? On a Friday?” her voice was shifting more and more with every sentence. Now she was all business. Apparently, seduction took place in the initial two sentences. “Friday is normally my second-best night of the week, but this is the 15th. Payday for almost everyone, whether you get ‘em once a week or twice a month.”

“That’s true,” Richard said. He paused for just a moment and then added, “I got paid today,” before she could speak again. “How much?”

“Four hundred?” she said with a slight questioning tone in her voice. Maybe she’s an amateur, Richard thought. Or maybe no one had asked her to stay all night before. Or maybe she’s not an amateur, does want to make some decent money, but is more interested in minimizing the amount of risk she takes tonight. Risks that include, but are not limited to: traveling by car; the variety of physical violations that can happen to a girl alone in a bad neighborhood; police involvement; increased exposure to sexually transmitted diseases by sheer numbers of sexual partners, etc. Whatever the case, Richard wasn’t going to minimize anything for that much money.

“Four hundred? That means you’re not coming over to hold hands and give me a back rub.”

“Is that a question? ‘Cause I can’t really get into it on the phone…” Kitty began.

“It wasn’t,” was all he replied.

            After some logistics were handled he hung up the phone and waited. Richard was ready for this to happen. It was so far away from what he’d previously had in mind for this evening that just the taboo-ness made it ten times sexier. He just wanted her to be at his apartment already. He wanted to breeze through the awkwardness and get right down to business. And, most of all, he wanted to make a lot of noise so that his upstairs neighbor could hear them. Hopefully, she would get jealous and think ‘why not me?’

            A few minutes later, Richard went outside to wait for Kitty to arrive. In the time it takes to smoke twice a black foreign sports car pulled up to the curb in front of him. The driver rolled down the window and asked Richard if he was Dick. The woman was peculiarly exotic, and Richard was eager to get her upstairs. He showed her where to park, and waited for her. When she was done and came walking up to Richard on the sidewalk he got his first good look at Kitty.

She was about five foot nine, very slender, light brown complexion, jet black hair, and dark eyes. She wore an ultra-tight one-piece leopard-print mini dress with a black leather blazer and black thigh-high boots. This ensemble somehow managed to avoid looking street-walker trashy, but was screaming “promiscuous girl”. Kitty walked straight up to him and leaned in to kiss his cheek. At the same time, a light reflecting off of the large glass door of Richard’s apartment building caught his eye. With his arm around the leopard-clad waist of this callgirl, he glanced up just in time to make eye contact with the true object of his desire: Julie, his upstairs neighbor. She was dressed up in the kind of clothes free-spirited young ladies like to wear when they go to dance clubs and they want to go from “hi my name is Julie” to “don’t cum in me, I’m not on the pill” in as few steps as possible. And she looked good, accompanied by an entourage of other Young Urban Professionals, both male and female. He almost spoke to her but failed to find the words. Instead, he just opened his mouth, looked directly at Julie, and then closed his mouth again. He noticed that Julie couldn’t help but notice Kitty with “that dude from downstairs” and glared at her maliciously.

“Nice dress,” Julie said, so rudely and sarcastically that everyone around felt awkward. Everyone except Kitty, that is.

“Oh, this?” she feigned, “I wasn’t planning on wearing this for very long.” Richard’s half-Thai pay-date leaned heavily into him. Then she stuck out her bubblegum pink tongue and licked Richard from his Adam’s apple to his lower lip so delicately that the residue, like a snail’s trail, disappeared in a second. Without waiting to see anyone’s reaction, Kitty led Richard into his building with genuine familiarity. Once inside Richard’s apartment, he knew that his initial plan was in jeopardy. Sometimes Julie came home at midnight. Sometimes it was just before dawn. But a lot of the time, she didn’t come home at all. Richard confessed to Kitty that he was only using her to make Julie jealous.

“What do you want to do?” he asked her. Kitty found the idea romantic, almost. But it also suited her desire to make the bitch from the sidewalk feel bad after their exchange.

“Why don’t we just get to know each other better? We can figure the rest out later. Or do you want me to go?”

 “No, stay,” Richard told her.

They sat up drinking Scotch, chatting on the couch, waiting for Julie to come home so Richard could then fuck Kitty while imagining Julie, who would hear Kitty vocally and otherwise confirming that she was enjoying Richard so much that Julie would wish it was her that was being trounced so. It was more than unlikely to work, but at least it was a sweet attempt at revenge.

Richard woke up around 7 o’clock on the sofa. He realized Julie hadn’t come home last night. Then he found Kitty asleep in his bed, where he joined her. They both slept late into the morning. Before Kitty left, though, she agreed to come back next week and try again. She had had fun with Richard, so she only charged him two hundred dollars to drink his booze and sleep in his bed alone. Richard was happy to oblige.

            The next Friday rolled around too slowly. Richard’s workweek was always hell. Of course, Julie was having a little bash to celebrate week’s end. Richard called Kitty over and they hung out on Richard’s couch again, sitting and waiting. By midnight it sounded like the stampeding elephants were leaving the party upstairs. And by 2 o’clock the apartment was unusually quiet. Richard led Kitty to the bedroom and they waited for Julie and Lucky Number X to get started, but nothing happened for quite some time.

“I think she’s alone,” Richard whispered.

“But we’re not,” Kitty whispered back.

            They shyly undressed each other, which might not seem strange for a second date, but strange for a second date with a hooker. After some heavy petting and childlike giggling, their comfort grew to intimacy. Soon an operatic range of vocals Richard assumed were only rehearsed theatrics, but in fact, were not, flooded his room and began to disturb his upstairs neighbor. Richard was so enthralled in his ruse with Kitty that he didn’t even pause to consider what Julie’s reaction might be until he heard her stereo click on. The music got louder and louder. It was more volume than she had at her soiree earlier that night.  

“Aww, she can dish it out, but she can’t take it,” Kitty said. It was annoying, for sure, but Richard didn’t care. He was enjoying this moment for what it was, not for what he had wanted it to be. Subconsciously, Richard began to thrust and grind with such renewed vigor that, not only did Kitty move up an octave, but Richard’s replica Monet shook loose from the wall. The painting slid down the wall and came crashing to the floor. The carpenter’s nail that had held it, however, tumbled down the wall with a piece of wire still wrapped around it. It just so happened to settle between the prongs of the electrical plug of Richard’s bedside lamp in a nearby power socket. With one, loud, bright blue POP of electricity- brighter than a photo flash, louder than thunder- his room went dark, and Julie’s room fell silent. He had knocked the power out in the whole building. Without missing a beat, Richard conducted his final movement in the symphony of sounds he and Kitty were making. The climax was breathtaking, and probably half the building knew it.

            The next day, Saturday, Richard boldly decided to strike while the iron was hot. His new friend and his little plan were getting quite expensive, but he called Kitty over anyway. Julie was having another get-together, as was her custom. By about 1 o’clock in the morning, all the guests had left, except one: the Lucky One. Very quickly Julie and the man of the hour were at it, but it sounded a little different to Richard.

“Something’s wrong,” Richard said.

“What do you mean? It sounds like she’s having a whale of a time to me.”

“After a year of listening to Julie screw two or three times a week, I’ve noticed a thing or two,” he said. “Normally it sounds more physical.”

Kitty looked at him blankly. “What do you mean physical? They’re fucking. How much more physical can you get?”

“Not that. Normally you can’t really hear her. The bed is always creaking, or you hear skin clapping; stuff like that.” They paused to reflect. Tonight it was all moaning. Either the guy up there with her was a real stallion in the old sack-a-roo, or Julie was faking it.

“Maybe she’s really enjoying it,” Kitty suggested, knowing full well what ‘faking it’ was all about, “but if you say that’s not typical for her, you could be right.”

“Do you think there is something special about the guy?” he asked.

Kitty smiled. “Maybe he’s a pro.”

“I was thinking ‘special’ to her emotionally. I mean, why would she fake it all of the sudden?”

“I’ll give you one guess,” Kitty told him.

 Kitty pulled off Richard’s clothes and then they began to take their course. At first, their voices sounded forced and their movements were exaggerated. They instantly fell into competition with the folks upstairs.

Richard decided to focus, to tune out the couple upstairs. Soon he managed to find the same natural groove he’d found the week before. Then he was unaware of anything beyond his room and focused all his attention on Kitty, who was either truly having an orgasm, or truly a professional worthy of a Tony. The room upstairs went quiet as Richard and Kitty finished together. He collapsed beside her, hyperventilating.

“Oh, my God,” was all Kitty could muster.

            The next morning was a bit awkward. Kitty didn’t stay for breakfast or even talk much. Richard had never seen “Pretty Woman” before, but he knew it was ludicrous to fall for a callgirl.

“I had fun,” she told him.

“Me, too.”

Then she collected her fare and left him alone again.

Richard’s whole workweek was agonizing. Every night he listened to Julie come home and go through her apartment. To the kitchen, to the bathroom, to bed by midnight.

 Nothing else happened at all.

He was sitting in his apartment the next Friday night thinking about calling Kitty even though Julie was quiet upstairs. He was missing Kitty’s company but wondering where Julie could be when there was a knock at the door.