At the restaurant Emily took a seat and ordered a salad and a vodka Diet Coke from the waitress who came by. As Emily ate her salad and sipped her drink, she browsed through twitter and Reddit, responding to a couple of DMs and flagging a few others to deal with later. When she was done Emily checked the time and saw it was shortly before 7. She signed the chit with her room number, then headed back there.

In her cabin Emily washed her face, brushed her teeth and quickly reapplied her makeup. She changed into a pair of panties that had a built-in O-ring and harness for her strapon, as well as tossing her spare harness into her purse in case the other woman wanted to wear the strapon. She also added the two dildos that fit the harnesses; one slim and one thicker and longer, both bright purple. She reapplied some deodorant and spritzed on some subtle perfume, then left for her date.

The cabin Emily’s schedule took her to was on one of the higher passenger decks, and even the hallways looked much more luxurious than the one outside of Emily’s cabin. Emily knocked on the cabin door right at 7:30, and the door opened almost before she took her hand from it. Inside was a shy looking woman in her mid-thirties who Emily recognized from her orientation tour. The woman stepped aside to let Emily into the cabin. The cabin was beautifully appointed with a sitting area that held a love seat in front of a giant TV, a king sized bed behind a half open partition and a balcony that looked out onto the ocean. There was an open bottle of white wine on the table in front of the love seat with two glasses poured, one already half drunk.

When Emily was inside the other woman closed and locked the door behind her. “I’m, um, I’m Christy,” the woman stuttered, looking at her feet.

Emily leaned forward and kissed the woman on her cheek. “You don’t have to be nervous,” Emily said. “I’m Emily and I’m here for whatever you want.”

Christy blushed deeply, and turned her back to Emily, walking over to the table with the wine. “Would you like a drink?” Christy asked as she picked up and finished the wine in the half full glass then refilled it.

“I would love one,” Emily said. Christy nodded, still not looking at her then picked up both glasses of wine and walked out onto the balcony. There was another small couch and coffee table on the balcony. Christy set the wine glasses down on the table and sat down. Emily slid the balcony door closed behind them and sat down beside Christy, allowing her leg to brush against the nervous woman.

Emily picked up and took a small sip. Christy grabbed her own glass and took a deep drink. Emily was about to say something when Christy blurted out, “I’ve never done this before!”

‘No kidding,’ Emily thought but what she said was, “It’s okay! We can take this at whatever pace you want.”

“No, I mean, I’ve never even kissed a girl,” Christy said, looking into her glass of wine. “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 and reached over to start rubbing the woman’s back. “Don’t worry about it. We can do as much or as little as you like. Would you like to talk about it?”

Christy sighed and leaned forward to let Emily massage her lower back over the t-shirt the woman was wearing. “My husband left me for his ex six months ago. I had tried so hard to be the perfect housewife, but I just couldn’t make it work, and I don’t want to hide who I am anymore. I thought this cruise would help, and when I heard about you girls…” Christy trailed off and took another drink of wine, finishing her glass. Then she pulled out a pack of cigarettes and a lighter. “Would you like one?” She asked, proffering the pack to Emily.

Emily took the pack of cigarettes and the lighter. She took one from the pack, put it between her lips and lit it, taking a deep drag. Then Emily took the cigarette from her mouth and placed it between Christy’s lips. Christy was stunned for a moment, then took a drag herself as Emily took out another cigarette and lit it.

They smoked together in silence for a few moments, then Christy put her cigarette down in an ashtray on the coffee table and leaned over to kiss Emily. Christy tasted like smoke and Chardonnay and Emily carefully put her own cigarette down in the ashtray without breaking the kiss. 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 back, and Emily leaned back on the couch so that Christy was half lying on top of her. One of Christy’s hands found one of Emily’s breasts and began to massage it through her sundress as they made out. Emily returned the favour, grabbing Christy’s ass and massaging it through her jeans.

They made out like that for a few minutes until a wolf whistle from a balcony beside them interrupted them. Christy sat up like a shot, and Emily lazily followed her. There were two women watching from the balcony beside them who gave a wave. Emily waved back as Christy hid her face in her hands. Emily pulled Christy's hands away from her face, gave her another kiss then whispered into the woman’s ear, “Why don’t we head back inside?”

Christy nodded and allowed Emily to lead her by the hand back into the cabin. Emily gave a last wave to the women next door as she closed the balcony door behind herself. When she turned around Christy was frantically stripping. In moments she was standing naked in front of Emily, revealing large but firm breasts, a slightly pudgy tummy and a waxed pussy. Emily put her hands on Christy’s shoulders and steered her into the bedroom, then pushed her down to lay on the king sized bed.

Emily lay down on top of Christy, letting her mouth land on one of Christy’s breasts. She sucked the nipple into her mouth and sent one of her hands between Christy’s legs. The woman was soaking wet, and almost before Emily’s fingers hit her clit Christy began to cum. She thrashed on the bed as Emily kept sucking on her nipple and rubbing vigorously at her clit with her fingers. Emily quickly brought the repressed woman to a second orgasm before Christy found the strength to push her away.

“Did you bring a strapon?” Christy panted, flushed and pushing herself up on her elbows to look at Emily.

“Of course,” Emily said. “Do you want to wear it or should I?”

“You! Fuck me please,” Christy said with a feavered gleam in her eyes. Emily went back into the main room to grab her purse, stripping off her dress as she did. She came back with the two dildos, a bottle of lube and a condom. “Which one do you want?” Emily asked, showing Christy the two different sized dildos.

Christy’s eyes went wide but she said, “The big one!”

Emily quickly hooked the dildo into her panty harness, then slid a condom over top of it and slathered it with lube. Emily stepped up to the bed and was about to ask the woman what position she wanted when Christy reached out and grabbed Emily’s cock and steered it into her pussy. Christy lay back on the bed as Emily slid inside her. Emily started to kiss the other woman, rubbing the breasts against each other and slowly thrusting her hips in and out.

Christy moaned around Emily’s tongue in her mouth, her hands grabbing Emily’s ass and trying to push her even deeper, Emily’s cock all the way inside Christy’s pussy. Emily kept kissing Christy hard until Christy began to push her up and away. Emily was about to ask if she would slow down or stop when Christy’s mouth latched onto one of Emily’s nipples, sucking and biting as Emily continued to fuck her.

Eventually Christy pulled her mouth from Emily’s breast and panted, “Roll me over.”

Emily pulled back, withdrawing her strapon from Christy’s puss. As soon as it was out, the woman rolled onto her hands and knees, presenting her ass and dripping pussy to Emilly again. Emily knelt on the bed behind her and lined her cock up with Christy’s slit, then lunged it in deep. Christy moaned and began frantically rubbing her clit with one hand as Emily fucked her fast and deep. In under a minute Christy was hit by another massive orgasm and collapsed underneath Emily, causing the strapon to slide out of her.

Emily stood up and walked into the ensuite bathroom where she pulled the condom off her strap and wiped the lube off the toy and her hands with one of Christy’s hand towels. When she returned to the bedroom, Christy was still chest down on the bed, legs splayed open and panting.

Emily sat beside Christy on the bed and asked, “Did you enjoy it? Was it what you hoped for?”

“Oh god yes,” Emily groaned without moving. “How much do I owe you?”

“Let’s say $250 because I used my strap.”

Christy pushed herself back up and rolled over to the bedside table. She opened the drawer and pulled out a money clip. She peeled four hundred dollar bills off the clip and handed them to Emily. “You definitely earned the tip,” the woman giggled.

Emily gave the woman one last kiss, then left the bedroom, pulling the door closed behind her. She unbuckled the dildo from her harness and put it back in the purse along with the cash, then dressed again. Before she was done she heard faint snoring noises coming from the bedroom, so she left as quietly as she could.