The Cruise

Prologue

Emily has finished off her cam show for the night, and was just saying goodbye to her viewers when she got a private message request from one of her regulars. She accepted, expecting to schedule a private or fetish show.

'Hi Debbie. Did you enjoy the show? ;)' she typed.

'As always,' Debbie typed back. She was one of the few women who regularly logged on to watch Emily's cam shows. 'Actually I've got a bit of a proposition for you.'

Emily knew that some cam girls also dabbled in prostitution, but Emily's tastes didn't run in the directions of most of the people who would be her clients. On the other hand, Debbie was a woman so Emily decided to hear her out. 'What is it?'

'You're into girls right?'

'Ya,' Emily typed back. She was gay in fact, and did cam shows with some of the other girls in the business from time to time. 'Are you looking to meet up or something?'

'Not exactly,' Debbie sent. 'I work for Olivia Cruises. We do cruises in the Caribbean specifically for queer women. It's mostly women in their 40s and 50s, but some are younger.'

There was a pause and Emily was about to ask what that had to do with her when Debbie continued, 'We also like to make sure there are a few women in their twenties who are available for 'paid company.' One of our girls canceled at the last minute. Do you have a passport?'

Now that would be an interesting trip, Emily thought. See the Caribbean and screw a few old dykes along the way. 'I do. How would it work?'

'You get half price on a single cabin ticket, food and booze included. The staff steer any interested women your way, and you tip them out 20% of whatever you make. Most of the girls in the past have asked for $200 for an hour. It's a ten day cruise that leaves from Florida next Friday."

While Debbie gave her the exact schedule and cabin cost, Emily did some quick math. The cabin would be $600 and the return plane ticket would be $800. Add in another $200-300 for some new clothes and incidental costs, and she would need to see two or three women a day to make any money. Emily figures she could do that. Especially if she found some women into kinky shit that she could charge extra for.

'Alright, I'll do it,' Emily said, and started making preparations. She bought her plane ticket, and made an appointment to get waxed and have her hair and nails done. She also ordered a few new toys online that she'd be taking with her. It was going to be a fun working vacation!

Day one

Emily took a red eye into Miami and caught a shuttle bus from the airport to the harbour where the ship was leaving from. She had decided on a light femme chic look for the trip, lots of sun dresses, shorts and pastel shirts and a couple of not too revealing bikinis. She didn't want to look like a street walker, as she figured that wouldn't be what the women on the cruise were looking for. She was wearing a short but not too short sundress with pink flowers on it, a pair of sandals, boy short panties and no bra over her modest chest. She arrived to the harbour just as early boarding was starting as she had been instructed.

She left her bags with the crew who would deliver them to her room, and climbed up the ramp to the ship. It was a large cruise ship, able to hold almost 2,000 passengers plus the crew. At the top of the ramp a crew member scanned her ticket, then gave her a key card that would open her room and directed her to the elevator that would take Emily to her deck. Emily found her room, a small cabin with a single bed and no windows because it was in the interior of the ship. She found a note on her bed along with the welcome package that directed her to go to one of the staff offices in an hour for her special orientation.

Emily hopped into the small shower in the cabin to clean up after the flight and redid her makeup, then went to where the note directed her. The door to the office said it was a Jenifer Grate, head of Concierge services. Emily knocked, then heard a voice from within telling her to enter.

Inside was a rather plain looking woman in her late forties, short brown hair and wearing the skirt and blouse of one of the staff. She motioned to a seat and Emily sat down.

"Now I know Debbie talked through most of this with you but I want to go over the ground rules. You're not to solicit any of the guests. Either let them approach you or the staff will let you know about an interested woman," Ms. Grate said. She slid a small cellphone across the table to Emily. "Keep this phone with you. You'll be expected to be on call from 4 pm until 4 am so I suggest getting some sleep when we're done here. You tip me out 20% of whatever you make, and I will be expecting a minimum of $100 a day. You can come by this office shortly before noon each day to drop it off."

Emily nodded and took the phone. "I think I can handle all that," she said, and got up to leave.

"One more thing before you go," Ms. Grate said. "Lock the door will you?" As she said that the older woman pushed her chair back from her desk and hiked up her skirt. As Emily locked the door to the office, Ms. Grate slide her panties down her legs, revealing a dark brown bush. She spread her legs and said, "I'm going to have to make sure you're any good."

Emily went over and knelt between the woman's legs, running her hands up and down her thighs, leaning in to lick along the side of her crotch. Inside the mass of hair Ms. Grate's pussy opened up to reveal the wetness inside. She had obviously been anticipating this moment, so Emily didn't waste any time and dived in. She licked up and down, probing into the older woman's pussy with her tongue, fucking her with it as she moaned. Ms. Grate ran her fingers though Emily's short hair, then pulled her up so that Emily could focus on her clit. Emily did as the older woman wanted, circling and rubbing it with her tongue, trying to get the concierge off as quickly as possible.

After a few minutes of serious attention to her clit during which time Emily slid two fingers into her pussy to massage her g-spot, Ms. Grate bucked her hips against Emily's face, squeezing her hard with her hips. Then she sat back with a sigh, pushing Emily's face out from between her legs.

Emily wiped some of the woman's cum off her face and stood up. "So?" She asked with a smile.

"You'll do. First timers orientation is at four. You should go so you know where everything is. Feel free to nap, no one will call you before then. Just keep the phone with you after that because you'll be on call. And I'll see you back her before noon tomorrow." With that Ms. Grate dismissed her. Emily headed back to her cabin to wash her face and grab a nap. It was going to be an eventful trip.

When Emily woke up from her nap, she adjusted her makeup again, then went to meet her orientation group. She arrived just before four to find a group of about fifteen women milling around with a staff member checking names off a list. Emily went up to check in and got a bracelet that would get her food and drinks from the various restaurants and bars. More women arrived, and at a little after four the group set out on the tour.

Everyone in Emily's group was also on their first cruise, so the tour focused on safety procedures, where the life boats where and what to do if there was a fire. Once what was out of the way they were shown where the pools and gym were, the different restaurants and onboard dance club. Most of the restaurants served food that was included in the price of the ticket, but there were a couple of fancy ones that guests had to pay for. Emily figures that she could get at least a couple of her 'dates' to buy her a fancy meal.

Emily also spent some time checking out the other women in her group. Most were in their 40s or older, and about half had come as couples. There were a few women in their late twenties or thirties, but Emily was the youngest by about five years. She wondered if she'd be screwing any of them later.

When the orientation was over, Emily went up to the deck to watch the ship pull away from the dock and take a few hits off her juul. She was surprised by how little movement she felt as the cruise ship set sail. They'd be at sea that night, docking at some small island the next afternoon for people to go ashore and do touristy things. Emily was thinking of going to one of the many bars to get a drink, when the phone Ms. Grate had given her buzzed.

There was a text message that read, 'Mary would like to see you in her cabin at 6:30,' and gave the cabin number. It was just before six, so Emily took one last hit from her juul and headed back to her cabin. In her cabin she quickly brushed her teeth, then tossed some lube, condoms and a few toys into her purse, just in case Mary wanted to try any of them.

Mary's cabin was on one of the fancier decks, and on the outside of the ship so she would have a window out onto the ocean, maybe even a balcony. Emily knocked, and a few seconds later the door unlocked and opened. Mary was a slightly over weight woman in her fifties, with short grey hair in a faux hawk, wearing a tank top and some shorts. She stepped aside to let Emily into the cabin. The cabin was about twice the size of Emily's with a double bed, mini bar, a few windows looking out onto the ocean and a door that Emily assumed lead to the bathroom.

"So you're the new girl," Mary said as she looked Emily up and down with an appreciative eye.

"Yes ma'am!" Emily said with a smile. "What can I do for you?"

Mary sat down on the bed and laid back, hands behind her head. "Why don't you start by giving me a little strip tease. There's $200 on the mini bar for you."

Emily set her purse down on the mini bar, and put the pile of twenties inside it. She was about to turn back and start a dance when Mary called out, "Grab me a beer from in there will you?"

Emily opened the mini bar fridge, bending down from the waist to show off her legs and ass to Mary, and pulled out a can of beer. Either Mary had stocked her fridge special, or the more expensive cabins had a different selection, because the beer was from some microbrewery that Emily didn't recognize, as opposed to the Bud Light in her own fridge. She opened and handed the can to Mary, then started up some music on her phone to dance to.

The music was a playlist of some of Teegan and Sarah's more danceable stuff, and Emily began swaying along to it. It was her favourite mix for stripping on cam, and she quickly got into it. She turned around and flipped up the hem of her sundress, showing off the thong she had changed into. Keeping her back turned she kicked off her sandals and stripped off her dress until only the thong was left. A second later a piece of fabric hit her in the back.

Emily turned to see that Mary had taken off her shorts and had tossed them at her. She was now laying naked from the waist down, legs spread to expose a surprisingly small pussy on such a big woman, with a light covering of grey-brown pubic hair. Taking the hint, Emily moved over to the bed and began to lay down between Mary's legs.

"Start with my feet," Mary said, moving one towards Emily's mouth.

Emily took it and began to lick the soles of Mary's feet. They were calloused, but clean, the woman having obviously showered shortly before Emily arrived. When Emily ran her tongue between the older woman's toes, Mary gave an appreciative moan. She hadn't had a pedicure in years if ever, but she obviously loved having them licked. Emily spent about five minutes alternating between feet before she began to kiss up Mary's calves and thighs. Mary grabbed one of the pillows from the bed and put it underneath her ass to raise her pussy up.

Emily brought her mouth the the older woman's slit and began licking. She let Mary's moans guide her to the right places, and was soon flicking her clit as she slid first one then two fingers inside her. "One in my ass too," Mary groaned, and Emily did as she was told, first wetting her index finger in the woman's pussy then pushing it into her tight asshole.

Mary took a while to cum, and Emily's jaw and wrists were starting to get sore when the other woman finally began bucking and moaning against her face. Emily sat up on the bed panting, pulling her fingers from the other woman.

"Thanks. Totally needed that," Mary said. "I'm going to go have a shower. Maybe I'll see you again," she said with a wink.

Emily took that as her cue to get dressed and leave. As she headed back to her cabin she checked her phone and saw that she had another appointment in an hour. And she needed to bring her strapon.

Emily decided she probably didn't have time to both eat and get ready, so she stopped on one of the outside decks to hit her juul again and grabbed a bottle of water and a granola bar from one of the snack stations. She checked the deck map to see where her next 'date' was, seeing that it was one of the largest cabins on one of the upper decks. She'd have just enough time to get to her own cabin get her harness and a couple of dildos and get there. Emily ate her granola bar in the elevator down to her cabin, hoping she'd have time to grab some dinner after this date.

In her cabin Emily took off her thong, and put on her strapon harness underneath her dress. She put two dildos that would fit the harness's O-ring into her purse, a short slim pink one and a larger flesh coloured one. She washed her face and hands, touched up her makeup and put on some more deodorant and a little bit of cologne. Then she left, hurrying off so she wouldn't be late.

Emily got to the cabin at just the appointed time, and knocked. The door opened immediately, revealing a shy looking woman in her mid thirties. Emily recognized her as another first timer from the tour earlier in the day. Her cabin was large and beautifully appointed, with a king sized bed and a balcony looking out onto the setting sun. There was an open bottle of white wine on the desk, and two glasses, one half drunk already. As Emily stepped into the cabin the other woman closed and locked the door behind her.

The woman stuck out her hand and said, "I'm Christy."

Emily took it and introduced herself, watching the woman blush as they shook hands. "Don't be nervous," Emily said. "I'm here for whatever you want."

Christy blushed deeper as she dropped Emily's hand. "Would you like a drink?" She asked, as she poured more wine into her own glass then picked them both up. Emily followed as Christy led them out onto her balcony and set the glasses down on a table in front of a love seat. She sat and Emily sat beside her, taking her glass and having a sip. Christy took a big drink of her own wine, sitting straight up, tense.

Emily was about to say something when Christy blurted out, "I've never done this before!"

"That's ok sweetie," Emily said. "We can take this at whatever pace you want."

"No, I mean I've never even kissed a girl," Christy said. "I can't believe I even came on this cruise, and now you're here and I don't know what to do!"

Emily suppressed a laugh, not wanting to offend the woman, and reached over to start rubbing her back. "Don't worry about it. We can do as much or as little as you want. Do you want to talk about it?"

Christy sighed, leaning forward to let Emily massage her back through her t-shirt. "My husband left me for his ex six months ago. I tried to be a good housewife, but I just couldn't make it work. I'm just so tired of hiding who I am, and I thought this cruise could be fun. Then I heard there were girls like you, I thought maybe a professional for my first time..." Christy finished the last of her wine with a single gulp, and pulled out a pack of cigarettes and a lighter. "Would you like one?" She asked offering the pack to Emily. Emily took one and after Christy lit her cigarette she took the lighter and lit her own. They both took a few drags in silence, then Christy put her cigarette down in the ashtray, leaned over and kissed Emily.

Christy tasted like smoke and wine, and Emily carefully put down her own cigarette without breaking the kiss, making sure not to accidentally burn the woman. Christy opened her mouth, and Emily took it as an invitation to slide her tongue into the other woman's mouth. Christy's hands began to roam over Emily's arms and back, and Emily leaned back on the couch so that Christy was half laying on top of her. Christy's hand found one of Emily's breasts and began to gently massage it, getting her nipples hard. Emily returned the favour my grabbing Christy's ass, sliding her hand under her shorts to squeeze her butt through her panties.

They made out like that for a while, until there was a wolf whistle from one of the balconies to the side of them, and Emily looked up to see a couple of women watching appreciatively from the balcony next door. Emily waved to them, then said, "Why don't we head inside?"

Christy nodded, panting, and grabbed Emily's hand to lead her inside. As soon as they got inside, Christy began frantically pulling off her clothes until she was naked, revealing a slightly pudgy stomach, waxed pussy and still firm breasts. Emily went up to her, and pushed her back so she fell onto the bed. When Christy was laying down Emily lay down beside her and took one breast into her mouth, circling the nipple with her tongue. She let her hand run down Christy's stomach until she found her wet slit between her legs. Christy moaned and arched her back, pushing her nipple into Emily's mouth as she was fingered. Almost immediately Christy came as Emily rubbed her clit, covering her mouth to try and keep quiet.

Emily kept strumming Christy's clit as she shook with the aftershocks, until Christy finally pushed her hand away. She leaned up on her elbows and asked, "You brought a strapon, right?"

Emily gave her a quick kiss and said, "Of course. Did you want to wear it or should I?"

"You wear it. I want to get fucked!"

Emily stood up and stripped off her dress so that she was wearing only the harness. She pulled the two dildos out of her purse and held them up. "Which one do you want?" She asked.

"Definitely the big one," Christy said, her eyes a little wide.

Emily undid the clasps at the front of the harness and slide the dildo through the O-ring, the buckled it back tight so the fake cock was standing out erect from her crotch. Then she rolled a condom onto the dildo, gave it a little squirt of lube just in case and climbed onto the bed. She was going to ask Christy what position she wanted when the woman grabbed Emily's cock and began guiding it to her pussy as she lay back on the bed. Emily lay on top of Christy, their breasts pressing together as Emily slowly slid her strap into Christy, kissing her as she moaned.

"Fuuuuuuuck," Christy groaned as Emily slid all the way to the hilt in her wet pussy, her hands grabbing Emily's ass and trying to push her deeper. Emily began to slowly fuck in and out, kissing Christy and playing with her breasts as she did. Christy was in ecstasy, writhing on the bed as she was pounded by Emily's cock. Cristy's pussy was soaking the bed underneath them when she put her hand to Emily's chest, pushing her back and making her stop.

"Did you want me to slow down? Stop?" Emily asked.

"God no," Christy panted. "I want to roll over."

Emily giggled, and pulled out, letting Christy get down on all fours in front of her, presenting her throbbing pussy for Emily once again. Emily grabbed Christy's hips, and pushed her cock inside her, watching it slide in underneath Christy's cute brown asshole. Christy moaned, one of her hands moving to her clit, her head and chest resting on the bed. Emily matched the pace of her thrusts to Christy's moans and movements, watching and feeling her hand move faster and more frantically on her clit.

Within minutes Christy was hit by another orgasm and collapsed under Emily. Emily pulled her cock out, standing up. She used some Kleenex to wipe Christy's juices off the strap and roll the condom off of it, then unbuckled the dildo from the strap and put it back in her purse while Christy lay panting on the bed.