Emily got back to her room at just before 3 am following her last client. The woman had only wanted oral, but she talked to Emily for almost an hour before the sex started, then had taken forever to cum. Emily didn’t bother to shower, just stripped off her clothes and climbed into bed, setting an alarm for 10 am on her phone as she did.

When the alarm went off in the morning, Emily hit snooze twice, then finally pulled herself out of bed. The only coffee available in her room was some shitty instant powder, so Emily made a mental note to have room service bring some fresh coffee tomorrow and grabbed a beer from the mini fridge instead. She drank the beer in the shower as she washed the last night off and woke herself up. Out of the shower Emily toweled herself dry, but didn’t bother with any makeup as she pulled on a sports bra, t-shirt and shorts. Then she went to find one of the breakfast buffets that the cruise offered.

At the buffet Emily grabbed a two seat table and ordered a coffee and mimosa from the waitress. After the waitress took her order, Emily went and loaded up a plate with pastries and fruit. As she ate and drank her coffee then mimosa, Emily scrolled through her personal phone. She sent some messages to friends giving them a very sanitized version of her trip so far, except for one who got all the gory details. Then she checked her video sales and custom video requests. Some were so outlandish she deleted them immediately, but there were two that Emily thought she could do before she went on call that afternoon. One was for a JOI video with a very detailed script that would take her less than ten minutes, another was for her peeing that she could easily do in the shower.

After she was done with her breakfast, Emily checked the time. She still had almost half an hour till she had to meet Grates, so Emily spent a little time leaning on one of the cruise ships' railings taking hits off her juul, watching the waves crash against the bow of the ship. Then she headed back to the elevators and took herself to Grates’ office.

When Emily arrived at 11:25 the door handle was locked and Emily heard some intimate sounding noises from inside, so she didn’t knock. Instead Emily leaned against the wall in the corridor across from the door, nodding to the odd crew member who passed by and played a game on her phone. At 11:34 the door to Grates’ office opened, and a cute girl about Emily’s age exited. She looked Emily up and down, but headed to the elevators without saying a word.

Emily went into Grates’ office, to find it smelling strongly of pussy and Grates still pulling down and adjusting her skirt. ‘That must have been one of the other working girls,’ Emily thought to herself as she sat in one of the chairs in front of Grates’ desk.

“So, how did you find your first day?” Grates asked, acting as if she hadn’t just cum on the face of a working girl.

“Busy!” Emily said with a laugh, then pulled out $250 from her purse. “Here’s your 20%,” she said as she slid the stack of bills over to Grates.

Grates took the money, counting it quickly then putting it inside an envelope that she closed into one of her desk drawers. “That’s good. Feedback has been good so far. Remember that you’re on call from four till four. Keep your work phone with you and check your calendar regularly and keep it updated with whatever dates you get.” As soon as Grates was done speaking to her, Grates turned back to her computer, Emily dismissed from her mind.

The previous girl had obviously given Grates the service she needed for that day, so Emily left quickly and went back to her cabin. Inside her cabin Emily set up her ring light and camera on the desk focused on the bed. Then she set up the camera and sat on the bed and recorded the JOI video, saying the naughty script to the camera, occasionally leaning back to rub her pussy through the thong panties that were part of the script. After Emily stripped naked, moved the camera and light to the bathroom. She squatted on the floor of the shower, pissed in a rocks glass and poured it over her tits, moaning all the time. Then she turned off the camera with her clean hand and showered, washing all of her piss off of her.

After Emily toweled herself dry she spent an hour editing the videos she had just taken, then uploading them to the men who had requested the custom videos, smiling as she saw the payments arrive. Then she did her makeup and hair, and dressed in a sundress and a thong. She glanced at the pile of dirty clothes lying beside her bed, and made a note to figure out where laundry was on the ship. Emily was about to go on call, but had no appointments in her calendar yet, so she decided to go and hit the casino.

The casino on the ship was huge, taking up at least half of one of the decks, but not very busy yet. There was a concierge desk near where Emily entered, so she decided to head there first.

“Is there anything I can help you with?’ The concierge asked with a smile.

“I’m one of Grates’ ‘special’ girls,” Emily told her. “If you get some high rollers in, maybe they’d like a pretty young thing on their arm for luck?”

The woman’s expression lost its smile and she looked down her nose at Emily, an impressive feat considering she was sitting and Emily was standing. “Not right now, but if anyone does ask, I know who you are. Now please don’t bother any of the paying customers while you wait,” the concierge said with a sniff.

‘I wonder what’s got her panties in a twist,’ Emily thought to herself as she wandered into the casino proper. She found a seat at a $1 blackjack table that didn’t have anyone besides the dealer at it, and took a seat. She changed a $20 bill for chips, then ordered a vodka cranberry from a waitress who stopped by. 

Emily spent the next hour slowly losing her $20, making small talk with a few other women who joined the table. Two appointments were added to her calendar, but they weren’t until 10pm and 1am. Emily lost the last of her chips, and was about to leave to get something to eat when a waitress came up to her.

“Emily?” The waitress asked.

“That’s me!” Emily said with a smile.

“A Ms. Bloom would like you to join her at the poker table, if you’re available.” The waitress indicated a table with half a dozen women around it near the center of the casino floor.

“Sure thing. Thanks!” Emily grabbed her purse, thanked the dealer and headed over to the poker table. As Emily approached the table and the women playing there, one of them saw her and pulled out a chair beside her.

“I’m Kate,” the woman said, and shook Emily’s hand as she sat down. Kate was wearing a tight calf length black dress that showed off her curves, had her hair pulled back in a tight bun and was wearing some understated but obviously very expensive earrings and necklace.

“The game is five card stud, $25 ante,” the dealer informed Emily.

Kate slid a pile of chips over in front of Emily for her to gamble with. Emily thought it was $500. “Do you know how to play?” Kate asked as antes were placed and cards were dealt.

“We’re about to find out,” Emily laughed as she checked her cards. She folded the first few hands when she wasn’t dealt much, trying to get a feel for the play style of the other women at the table. Kate and another woman played quite loose, betting on hands they had little chance of winning. A married couple played very conservatively, never betting unless they were sure they could win. The others fell somewhere in between  Emily began to play more aggressively, losing more often but winning enough big hands to make up for it. All the while she chatted and flirted with Kate, who had champagne flutes brought over for them.

They played for more than an hour while Kate slowly lost her money, until one of the married women finally cleaned her out with a big hand. “Well, that’s it for me,” Kate sighed, pushing back her chair. “Let’s go get some dinner.”

“I’d love to,” Emily said and tried to hand her chips back to Kate. There was $750 now.

Kate stopped her and said, “You won those fair and square sweetie.”

‘Score,’ Emily thought, and left a $25 chip for the dealer as a tip. “So where would you like to go for dinner?” Emily asked.

“How about Que?” Kate suggested. From her orientation tour Emily knew that Que was a fancy sushi restaurant and that it was one of the ones that had to be paid for separately.

“Sounds great!” Emily said and let Kate lead her from the casino. The continued to make small talk as they walked to the restaurant, and Emily found out that Kate was an executive at a large hedge fund in Chicago. This was her third cruise, and she had just gotten out of a long term relationship and was looking to have some fun. At the restaurant Kate got them a small corner booth, then excused herself to go and use the washroom. While Kate was gone, Emily updated her calendar, putting in that she would be busy for another two or three hours.

When Kate got back, she dropped something into Emily’s lap as she sat down. Emily looked and found a pair of lacy black panties, still warm and slightly damp. Kate had obviously just taken them off in the washroom. Emily lifted her eyebrows at the woman, but Kate didn’t say anything, just looked through the menu. When the waitress arrived with their sake, she poured Emily and Kate each a small porcelain cup, then asked what they would like to eat. Kate ordered a love boat with a selection of different rolls and sashimi.

When the waitress left, Kate leaned across the table and asked Emily to take her sandals off. Emily did, then began sunning her bare foot up and down Kate’s calf. Kate responded by opening her legs wider. Emily took the hint and brought her foot up between the older woman’s legs, tickling Kate’s thighs with her toes. Kate sipped her sake and tried to keep her face calm as she opened her legs wider for Emily.

Emily’s toe quickly found a bare wet slit. She continued to tease Kate even as their food arrived and the waitress set it down on the table. Kate was glad for the table cloth on their table that hopefully hid most of what was going on.

Emily continued to tease Kate as they ate, occasionally brushing her clit with her big toe and making the woman jump. Soon Kate was panting and struggling to eat, until she finally pushed Emily’s foot away. “You’re going to have to stop that otherwise they’re going to kick us out!” She told Emily, as if the whole thing hadn’t been her idea in the first place. Emily just smiled and kept eating.

When they were done and Kate signed the bill to have dinner charged to her room, she asked Emily, “Do you have high heels? Any clothes in leather?”

“I do,” Emily told her. “Would you like me to get dressed up?”

“Yes please,” Kate told her. “Come to my room in half an hour?” Then Kate discreetly handed Emily five one hundred dollar bills wrapped around a room keycard and told Emily her cabin number. “My safeword is ‘pineapple,’” Kate whispered in Emily’s ear.

Emily kissed Kate on the cheek as they left the restaurant, then hurried to her cabin. Inside she quickly stripped, then darkened her eye makeup a little and put on new lipstick in a darker shade of red. Once her makeup was done Emily slipped on her tight leather mini-skirt, not bothering with any panties underneath. She decided on a red bikini top and her three inch stiletto heels. Before she left Emily put the money from Kate and the money she had won at the casino into her room safe, then tossed her nipple clips, strapon harness and a few toys into her purse.

When Emily left her cabin, she decided to make Kate wait a little bit. She stopped at an outside deck railing to take a few hits off her juul and enjoy the admiring and slightly scandalized looks she got from some of the passengers and even a few crew. When Emily arrived at Kate’s cabin it was ten minutes late, and she opened the door without knocking.

Inside Kate stopped her pacing, looking both nervous and relieved. She had changed too, and was wearing a bright red bra and panty set that was so sheer that Emily could see her nipples and mound through them. She had also taken her hair out of its bun and her wavy black hair fell to her shoulders. Kate was about to say something, but Emily interrupted her by stepping up to her and kissing her. Emily pushed her tongue into the other woman’s mouth and wrapped her arms around Kate to grab her ass at the same time.

They kissed like that for a while, Emily massaging Kate’s ass through her sheer panties and Kate tentatively running her hands all over Emily’s back. When Emily broke the kiss Kate gasped, keeping her mouth open and her eyes closed. Emily pulled down the cups of Kate’s bra and sucked on first one nipple, then the other, getting them hard. “Stay,” she told Kate.

Emily pulled her nipple clamps out of her purse, and watched Kate’s eyes go wide as she saw them. Emily walked back over and delicately placed the clips onto Kate’s nipples, tightening them down until the woman gasped. Emily tugged the chain that connected the clamps to make sure they were secure, getting another gasp from Kate. Then Emily walked over to the mini bar and pulled out a mini bottle of champagne that she found there and poured herself a flute that she found on top of the mini bar.

Emily took her glass of champagne over to one of the love seats in the cabin and sat down, then started up one of her stripping music mixes on her phone. She looked at Kate who was standing wide eyed in the middle of the cabin and asked, “Well? Are you going to dance for me?”

Kate started, then began inexpertly swaying along to the music. Emily had to work a little to keep a straight face. Kate would never make it as a cam girl. She danced like a geriatric man with no sense of rhythm, but at least she was trying to turn Emily on, swaying and running her hands up and down her sides. Emily found herself starting to get turned on, from the enthusiasm and desire to please, definitely not from the dancing itself.

However, since Kate obviously desired to be topped hard, Emily decided to push her a bit farther. “Getting bored,” Emily said, picking up her phone and no longer looking at Kate. Kate redoubled her efforts. She clumsily unclimbed her bra and threw it to the side, then leaned forward to let her large breasts hang down and tugged at the chain that connected the nipple clamps. Emily looked up from her phone and watched, taking a deep drink of champagne and draining the flute.

“Take off your panties,” Emily commanded as she refilled her flute. Kate complied, lifting one leg then the other to take off the very damp cloth, almost falling over as she did so. “Turn around,” Emily instructed. Kate did as she was told, and Emily admired her plump backside. “Bend over,” was the next command. Kate put her feet shoulder width apart and did her best to bend from the waist. She couldn’t quite touch her toes, but as she bent over Emily could see the woman’s pussy between her legs. “Spread your ass,” was Emily’s next command. Kate complied, staying bent over and grabbed one ass cheek in each hand and pulling them apart. Emily admired the woman’s waxed wet slit with lips pulled slightly apart with her cute hairless asshole hole sitting above it.

Emily finished her second flute of champagne, then poured the small amount left in the bottle into the glass. “That’s enough,” she told Kate. “Lie down on the floor.”

Kate frantically complied, laying down on the floor in front of Emily. She winced as her large breasts sagged to each side of her chest, pulling the chain between the nipple clamps taught. As Kate lay down Emily peeled the foil wrapper off the neck of the small champagne bottle. Then Emily knelt between Kate’s legs and began to run the empty champagne bottle up and down Kate’s pussy lips, getting the opening and neck nice and wet.

Emily pushed the bottle inside Kate’s pussy. “Fuck yourself slut,” Emily commanded as she let go of the bottle. Kate’s hand flew to the bottle and grabbed it. Kate immediately began pumping the bottle in and out of her pussy, eyes half closed. Emily watched for a moment, then placed one of her stiletto heels to Kate’s lips. “Suck it slut,” Emily told her.

Kate quickly complied, opening her mouth and sucking the pointed heel of Emily’s shoe inside her mouth. She began to fuck herself almost violently with the empty champagne bottle as she licked and sucked on Emily’s pointed heel. When the song playing on Emily’s phone ended, she pulled her heel from Kate’s mouth, then wiped the woman’s spit off on her breast, poking at the nipple clamp as she did. Kate moaned and the hand that wasn’t holding the champagne bottle deep inside her pussy flew to her clit and began rubbing furiously.

Emily took her heel from Kate’s breast and bent down. She kissed Kate, then grabbed the chain that connected the nipple clamps she had put on the woman. Emily broke the kiss and ripped the nipple clamps off of Kate, sending her into a convulsion of pain. For a moment Emily thought she might have gone to far, but Kate didn’t say ‘pineapple,’ and as soon as she got control of herself her one hand began frantically fucking herself with the bottle while the other rubbed her clit. Emily stood back up, then placed the point of one of her stiletto heels against Kate’s nipple and began to push. As Emily pushed the pointed end of her heel into Katethe woman’s hand moved faster and faster on her clit.

Emily was beginning to worry that she was pushing too hard with her heel, that she might hurt the woman. She started to ease the pressure off, but as soon as she did, Kate grunted, “Harder,” her hand furiously pumping at her clit. Emily complied, putting more of her body weight into the heel that she drove into Kate’s nipple.

Emily moved around, not taking any pressure off the heel on Kate’s nipple, until she was standing right over the woman’s face, letting her look up Emily’s skirt to her bare pussy. As soon as Kate’s eyes locked onto Emily’s pussy her hand fucking herself with the bottle began to move even faster. In response Emily pushed her heel harder into Kate’s nipple. Kate began No own and buck frantically, her hand on her clit and her hand on the bottle moving almost faster than Emily could see.

Soon Kate’s breath started doing faster and faster, then her hands seized up as she grunted. Kate rolled over into a fetal position, her hands leaving her pussy and the bottle, though the bottle stayed inside of her. Emily allowed her heel to leave Kate’s nipple as the woman rolled over. Emily bent down and asked, “Are you ok?” Kate nodded, not opening her eyes. “Is there anything else you want?” Emily asked.

“No,” Kate grunted. “Please leave.”

Emily quickly gathered her things, glancing at Kate curled up on the floor of the cabin as she did. There was a large wet patch on the carpet where Kate had been laying before she rolled over. The woman was a squirter or had lost control of her bladder at some point. Before she left Emily bent down and kissed Kate on the forehead, whispering,”I had a lot of fun. You know how to find me if you want to do this again.”

As she left Kate’s cabin, Emily left one of her business cards on the woman’s desk. The card contained links to her twitter, the sites where she sold vids, and her name on the two main cam sites she used. If Emily was any judge, she was about to get a new regular.