The Cruise, part Four [FF]

Emily headed back to her room where she had a quick shower, then checked her work phone again. There were no appointments listed in her calendar and no text messages, so Emily decided to go for a swim. She changed into her one piece swimsuit, and headed to the top deck where there was an outdoor pool. The sun had set when she arrived but it was still very warm out. Emily put her purse down on a deck chair, then stepped into the pool. A quarter of the pool was sectioned off into 25 meter swim lanes, almost entirely unused as far as Emily could see. She went over and took one, then did laps for fifteen minutes.

When Emily was done with her laps, she got back out of the pool and toweled herself off and checked her work phone again. Still nothing so she brought her purse with her and sat down on a stool at the poolside bar.

A minute later the bartender came over and asked, “What can I get you?”

“Vodka cranberry,” Emily ordered, and when she had her drink she turned to watch the women in and around the pool as she drank. Most were in their forties, half obvious couples, a few of the single women flirting with each other trying to make a connection. When she finished her drink she turned back around and caught the bartender’s eye for another.

“Same again?” The bartender asked. Emily nodded and the bartender started making her drink. “How are you enjoying the trip so far?”

“Busier than I expected for the first day!” Emily laughed.

The bartender looked confused for a moment, then looked Emily up and down, really seeing her for the first time. “Ah, you must be one of Grates’s ‘special’ girls.”

Emily blushed a little, but nodded. “That’s right. It’s my first time. Either being on a cruise or doing…this. Not quite the same as camming,” she said with a little laugh and shake of her head.

“Almost makes me wish I was a passenger,” the bartender said with a wink and a cheeky grin. “Are you waiting for someone, or are you free right now?”

Emily checked her work phone again, saw a calendar appointment, but it wasn’t until the next day. “Still free. Why are you about to get off shift?”

The bartender laughed but shook her head. “Nah, but,” she inclined her head to a muscular butch in a one piece and shorts at the other end of the bar, “I might be able to find you a client.”

Emily thought for a moment, then shrugged. “That’s why I’m here. Send her over!”

The bartender walked to the other end of the bar and leaned over and whispered something to the woman. The woman looked over to Emily, then picked up her drink and walked over to Emily. She sat down beside her, and gave Emily’s thigh a squeeze and she pulled her stool closer to the bar.

“Do you like tequila?” The butch asked.

“Of course!” Emily said, putting on her best smile.

The butch finished the drink that she had brought over, then ordered two premium tequilas on the rocks. The tequila that she ordered wasn’t on the included drink list, but the woman just shrugged off the $30 a shot price and told the bartender to charge it to her room.

“I’m Taylor,” the butch introduced herself as the tequila arrived.

“Emily.”

“Of course you are cutie. Is this your first cruise?” Taylor asked, sipping her tequila as it arrived.

“Is it that obvious?” Emily laughed, taking a sip of her own tequila. It was smooth and harsh at the same time, a light brown colour and much nicer than any tequila she’d done as shots before.

“Oh, nothing that bad,” Taylor gave a musical chuckle, “but I take a trip every year or so and I haven’t seen you around before.” The sipped their drinks together while Taylor continued to massage Emily’s thigh with one hand. “So, how much will it cost to come back to my room?”

“Depends what you’re looking for,” Emily said, then reciting the cost list she had decided on before she arrived. “$200 to start with for my spectacular oral skills. I also brought a small toy and strap collection with me, and can cater to almost anything, though it might cost extra.”

Taylor laughed and said, “I have my own strap, don’t worry.” Then she dropped her voice and leaned over to whisper in Emily’s ear, giving it a quick lick as she did. “I’m going to eat you out, make you cum, then fuck your ass.”

It had been a while since Emily had anything bigger than a plug in her ass, but so long as the strap wasn’t too big and there was lots of lube, she thought she would be fine. “$350,” Emily quoted the woman. “Are you alright if I head back to my cabin quickly to get ready?”

Taylor nodded and finished her drink. She told Emily her cabin number and said, “See you soon!”

As Taylor left, Emily quickly updated the calendar in her work phone and finished her tequila. Then she fished a $20 bill from her purse and left it as a tip for the bartender. Back in her room Emily stripped, then grabbed one of the small disposable enema bottles she had brought with her. She sat down on the toilet and quickly cleaned out her ass, just in case. Then she got dressed again. She decided to wear a slightly longer sundress, but she didn’t bother with a bra or panties underneath it.

Twenty minutes after leaving the pool, Emily knocked on the door to Taylor’s cabin. Taylor’s cabin was only one deck above Emily’s and was also an interior cabin. When Taylor opened the door Emily saw that it was an identical size and layout to her own. Taylor might be spending money on Emily and top shelf tequila, but she hadn’t splurged on accommodations. Emily sat down on the bed as Taylor locked the door and waited to see what the other woman wanted.

As soon as the door was locked Taylor stepped out of her shorts, then peeled off her one piece swimsuit. She had hairy legs, armpits and crotch with toned legs and arms, a six pack and small high breasts. She came over to the bed and began aggressively kissing Emily. One of Taylor’s hands went under Emily’s dress and found her bare pussy.

“Naughty girl, no panties,” Taylor purred into Emily’s mouth as she first cupped Emily’s pussy with her palm, then began running a finger up and down Emily’s slit. The kissing and the stimulation from Taylor’s hand quickly started getting Emily wet. Taylor dipped her middle finger inside Emily’s slit to collect some moisture, then began flicking at her clit.

When Emily broke the kiss to moan, Taylor pushed her down onto the bed and pushed Emily’s dress up to her waist. Taylor immediately knelt between Emily’s legs and latched her mouth onto Emily’s pussy. Taylor’s tongue pushed as deep as it could inside Emily, making Emily moan as she was tongue fucked. After a few seconds, Taylor’s tongue moved to Emily’s clit, rapidly flicking at it and sending jolts of pleasure through Emily’s body. She was extremely skilled, better than any of Emily’s previous partners, and the pleasure was only magnified as Taylor pushed first one then two fingers inside her, curling them to rub along Emily’s g-spot. Emily tried to hold on as long as she could, but in less than two minutes Taylor pushed her over the edge of orgasm with her aggressive oral ministrations.

As Emily panted through the aftershocks of her orgasm, Taylor grabbed her and flipped her over so that she was on her knees and elbows on the other woman’s bed. As soon as she was in position, Taylor knelt down on the bed behind her, and used her hands to spread Emily’s asscheeks as wide as she could. Before Emily could ask what the woman wanted, she had stuck her face into Emily’s ass, tongue running over and probing at Emily’s tight asshole.

A soon as the shock passed, Emily moaned and enjoyed the feeling. She had only ever been rimmed a few times, and always when making a custom video or on cam the few times she had partnered up with another girl. It felt significantly better when she wasn’t having to worry about having to catch the act on camera. Emily did her best to push back and open her asshole for Taylor, letting the woman’s firm wet tongue invade her. Taylor’s tongue pushed against her sphincter, opening it in a way that felt different and much nicer than any toy Emily had used, though not reaching as deep.

All too soon the rimming ended. Emily sighed, and turned her head to watch as Taylor went to her still packed suitcase on the floor. She rummaged through the bag briefly, then pulled out a harness with a didlo already attached. The dildo had a small end that Taylor slid into her own pussy as she strapped it on, and a larger end that was half way in size between Emily’s own to strapon dildos. Emily gulped looking at the plastic cock, wondering if she could take it. As Emily watched, Taylor rolled a condom down over the dildo, then slathered it with lube. Taylor came back to the bed and squeezed some more lube onto Emily’s asshole, then massaged it in with two fingers.

Taylor pressed the head of her strap against Emily’s asshole, then began to press. The pressure was slow but steady, and Emily did her best to relax her sphincter while pushing back against it. Emily gasped as the toy opened then slipped past the tight ring of muscle. It was just slightly larger around than one of the plugs she used regularly, but much longer. The feeling was almost but not quite painful. Emily grabbed a pillow off the bed, squeezing it and burying her face into it as Taylor kept pushing until the dildo bottomed out inside Emily’s ass.

Taylor lent down so that her breasts and body weight were pressing into Emily’s back, her face beside Emily’s ear. “Do you like that whore,” the woman asked. Emily just moaned into the pillow.

Taylor knelt back up behind Emily and slowly withdrew her strap almost entirely, leaving only the head still inside Emily. Then she began to fuck Emily, slowly at first but increasing her pace with every stroke as Emily got used to, then started enjoying the sensation.

Taylor started panting as she fucked Emily faster and faster, the end of the strapon inside the woman’s pussy obviously stimulating her. “Play with your cunt whore,” Taylor commanded.

Emily complied, moving a hand between her legs and starting to rub at her clit. The stimulation on Emily’s clit combined with the rapid in and out of the strap in her ass soon had Emily panting, and Taylor started panting in time. Taylor reached one of her hands around to Emily’s chest and began grabbing and squeezing at her breast, pinching and pulling on Emily’s nipple.

As Taylor’s breathing started to cum faster, her movements slightly more jerky, Emily increased the pace of her own hand. The two women came together, and Taylor collapsed onto Emily’s back, burying her cock deep in Emily’s ass. They lay together panting for a few minutes, then Taylor rolled off Emily, pulling the strap out with a wet lube fart.

Taylor ignored Emily as she got off the bed and went into the small bathroom, closing the door behind her. Emily sat on the toilet and used a handful of toilet paper to wipe lube from her ass crack as she peed, then washed her face and hand. When Emily exited the bathroom, Taylor was snoring lightly on the bed, passed out with her plastic cock standing straight up from the harness around her crotch.

Emily quickly dressed and grabbed the pile of twenties that Taylor had left on the desk and put them in her purse. Then, as quietly as she could, she unlocked the door and slipped out into the corridor. Emily limped slightly as she walked back to the elevator that would take her to her deck and checked her work phone as she did. She had another scheduled appointment, but not until 1 am, three hours away. Emily planned on having a shower and getting a sandwich before then, and hoped the next woman only wanted to be eaten out.

Source: reddit.com/r/eroticliterature/comments/u2qpw5/the_cruise_part_four_ff