The Cruise Pt. 01

Emily sat down beside the woman and asked, "Was it what you hoped for?"

"God yes," Christy said, rolling onto her back. "How much do I owe you?"

"Let's say $250, because I used my strap," Emily said.

"Ok," Christy said and got up off the bed and went to grab her purse. She pulled a pile of twenties out and counted them, then handed them to Emily. "There's $300. You earned the tip."

Emily took the money and gave Christy one last kiss, then pulled on her dress and slipped out of the room. She checked her phone, but there were no messages about appointments yet, so she decided to find a bar to grab a drink and something to eat.

It felt a bit weird walking around wearing her strap harness, but since it was basically just a pair of panties with some straps to hold the O-ring on it wasn't uncomfortable. She found one of the smaller bars that served food, and grabbed a seat at the bar. The bartender, a young woman about Emily's age came over and handed her a menu.

"Would you like something to drink?" She asked.

"Vodka cranberry," Emily said. "And if you give me a minute, I'll get something to eat."

"Vodka cranberry coming up!" The bartender mixed up Emily's drink and put it on a coaster in front of her. "Have you decided what you'd like to eat?"

"I'll take a chicken burger and some fries," Emily said, handing back the menu.

"No problem," said the bartender, and put the order into a computer behind the bar. "Enjoying the trip so far?"

"It's been busy," Emily said with a laugh. "Ms. Grate has me running all over the ship."

"Oh, are you staff? I saw your first time bracelet so I assumed you're a passenger."

"Not staff, but not exactly a passenger either," Emily said, not sure if she should tell the woman why she was there.

"Ohhh, you're one of those girls!"

Emily shrugged. "Hope that's not a problem for you."

"Nope!" The bartender said, and gave Emily an appraising look. "Too bad they don't pay us much, you're probably out of my price range. But if you want I could steer a woman or two here your way."

Emily checked her phone to confirm she hadn't been texted any new appointments yet. "Let me eat first. I need a bit of a break."

"No problem," the bartender said with a laugh. "I'm Sarah by the way."

"Emily," Emily said and shook her hand.

Sarah went off to check on some other patrons, and Emily browsed her phone, updating her twitter and checking on the sales from her Clips4Sale account. Sales were pretty normal, but she was going to have to put up some new videos soon so that people wouldn't get bored. Maybe she could do some masturbation videos when she wasn't working Emily thought.

Emily's sandwich arrived, and she hungrily devoured it, then started picking at her fries as she continued to browse her phone. When she was done she pushed the plate away, and Sarah came to pick it up.

"There's a woman down at the other end of the bar who'd like to buy you a drink, if you're not booked up yet," Sarah said.

Emily looked over to see an athletic looking butch with hair in a tight pony tail at the other end of the bar who raised her glass to them. "Sure, send her down," Emily said.

Sarah went back over to the woman and said something to her. The butch finished her drink, then walked over and took a seat beside Emily. "Do you like tequila?" She asked Emily.

"Sure thing!" Emily said. "I'm Emily by they way."

"Of course you are cutie. I'm Taylor." Taylor then ordered two tequila on the rocks. They were off the premium menu, not included with the cruise, and cost $45 each. While they waited for their drinks Taylor put her hand on Emily's thigh and gave her a little squeeze. "Is this your first cruise?"

"It is," Emily said. "What about you?"

"Oh, I've been coming every couple of years for a long time. It's a great way to relax." Sarah brought them their tequila and Emily and Taylor clinked glasses. The tequila was smooth and harsh at the same time, and Emily took a small sip. It was much nicer than any of the tequila that Emily had at a club doing shots, and she savoured it.

"So how much to come back to my room with me?" Taylor asked.

"Depends on what you're looking for," Emily said. "It starts at $200 for some very good oral, and I happen to have my strap with me."

"Mmm, I have my own strap little girl. What if I said I wanted to eat you out then fuck your ass?"

Emily though fast. It had been a while since she had anything bigger than a small buttplug in her ass, but so long as the strap wasn't too big and they had lots of lube, she should be ok. "$350," Emily said.

"Done," Taylor said, and finished her drink. She waved over Sarah, and signed the bill so that the drinks would be charged to her account. "Drink up and lets hit the road."

Emily finished her drink, and followed Taylor out of the bar. On the way out Taylor stopped at the ATM that was in the bar and took out a wad of cash. She led Emily to the elevator, and took her to the same deck that Emily's cabin was on, though on the other side of the ship. Taylor's cabin was the same size and layout as Emily's. The woman obviously had money if she was buying top shelf tequila and Emily's time, but she was spending it on things beside her room. Emily sat down on the bed, waiting to see what Taylor would do.

Taylor locked the door and immediately began to strip. She pulled off her shirt and sports bra in one motion, throwing them aside to reveal her hairy armpits, toned stomach and rather large, slightly saggy breasts. Then she undid her jeans and pulled them off so she was standing there in her boxers. "Your turn," Taylor said with a wicked smile.

Emily pulled off her sun dress and kicked off her sandals, then leaned back and slid the strap harness down her legs, leaving her naked on Taylor's bed. Taylor came over and grabbed Emily's hips, pulling them to the edge of the bed and spreading her legs. Then she knelt between them, and immediately latched her mouth to Emily's pussy. There was no warm up or foreplay, just a wet tongue suddenly pushing inside Emily. Emily moaned involuntarily as Taylor began to tongue fuck her, her nose occasionally brushing Emily's clit and sending out little shocks of pleasure.

Taylor moved her tongue to Emily's clit and began sucking on it as she pushed first one, then two fingers into her pussy. Fortunately between Taylor's saliva and the stimulation, Emily was wet enough that they slid right in. Taylor quickly found Emily's g-spot and began curling her fingers against the spongy bit of flesh. Emily moaned. Taylor didn't waste any time, she just went straight for the parts that felt the best. When Taylor pulled her fingers from Emily's pussy she let out a groan of frustration, which was quickly replaced with one of shock as Taylor's index finger pressed against her asshole. The greasy finger quickly slid inside, expanding Emily's sphincter. It was followed by a second finger, opening Emily up in a way that was both pleasurable and slightly painful.

Taylor kept working her mouth against Emily's clit and her fingers in her ass, until suddenly and a bit unexpectedly, Emily found herself grabbing the back of the other woman's head, trying to increase the pressure of her tongue as she came. As the aftershocks began to settle down, Emily had to push Taylor's head away, too sensitive for more attention.

Taylor stood up, a wicked grin on her face. Then she opened a drawer in her dresser and pulled something out. She held up a dildo attached to a harness. There was a small part that would go inside the wearer's pussy, and a larger dildo for fucking her partner. "Think you can take it?" Taylor asked.

Emily looked at the strap. It was in between the size of the two dildos she had for her own strap, but she'd used larger things in her ass sometimes for videos or on cam. "For sure," Emily said. "I've got some lube and condoms in my purse."

"Oh, I came prepared," Taylor said, dropping her boxers and sliding one end of the toy into her hairy pussy. Then she buckled it on, and grabbed a condom from the same drawer the harness came out of. She ripped it open and quickly rolled it down the strap, then took a bottle of lube and liberally applied some to the toy. "On all fours slut," Taylor commanded, and Emily obeyed. She rolled over and propped herself up on hands and knees, presenting her ass to Taylor. Taylor squirted some more lube onto her fingers, and massaged it into Emily's asshole.

Then the tip of the strap pressed against Emily's asshole, and slowly but surely began to press in. Emily gasped as the toy opened her up, larger than anything she had had in months. The lube helped, but it still hurt. Emily leaned her face down, grabbing and squeezing a pillow, trying not to cry out. After what felt like an eternity Taylor bottomed out the dildo in Emily's ass, her thighs pressing into Emily's legs. Emily panted, trying to focus on the pleasurable aspects.

"Play with yourself whore," Taylor grunted, as she began to slowly fuck Emily's asshole. Emily obeyed, one hand flying to her pussy and beginning to rub her clit, trying to let the pleasure out weigh the pain. Taylor kept a slow and steady pace, withdrawing her strap almost completely, then sliding it back in to the base. Emily kept playing with herself, starting to enjoy the fullness in her asshole, squeezing back against it.

One of Taylor's hands reached down and grabbed Emily's breast, mauling and pinching it as she increased the pace of her thrusts. "That's it whore, take my cock in your ass," Taylor grunted, panting as the end of the dildo in her pussy worked her close to the edge. Finally she bottomed out the strap in Emily's ass one last time, and collapsed on top of the smaller girl with a shudder.

They lay together panting for a minute, then Taylor rolled over, pulling the strap from Emily's asshole with a wet lube fart. While Taylor lay there in the afterglow, Emily went into the small bathroom and closed the door behind her. She sat down on the toilet and pushed as much of the lube from her ass as she could while she peed, the wiped and cleaned herself up a bit. Taylor was still lying on the bed, cock sating up straight, but she was starting to snore lightly with half closed eyes. Emily tossed her own strap harness into her purse, grabbed the cash, and pulled her sundress back on.

Emily quietly left the cabin carrying her purse in one hand, sandals in the other, limping slightly from the soreness in her ass. She checked her phone and saw that there was another appointment waiting for her. Emily sent back that she would be a few minutes late, she needed to stop by her cabin and clean up a little.

In her cabin Emily took a couple of Advil that she washed down with a beer from her mini bar. Then she hoped into the shower and had a quick wash, making sure to get any remaining lube from her ass. When she was out of the shower, Emily dried off and put on a new thong and clean skirt and tight shirt. Hopefully the next woman would only want to be eaten out, Emily thought to herself as she left her cabin.