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Click hereThe sun was getting lower in the sky, the last rays of orange light illuminating the handful of clouds scattered across the heavens as twilight crept in. I'd just arrived at Anna's place after my first training day for my new job. Anna and Vanessa were lounging by the pool, although I wasn't sure how long that would last as the evening breeze was rolling in and it hadn't been a particularly warm day. At least, I hoped it wouldn't last, because I hadn't brought a suit, and I wasn't keen on wearing the extremely short and tight ones Anna had bought me in front of her sister when I was trying to make a good first impression.
"I don't need to throw a swimsuit on, do I?" I asked. "I assume your pool time is coming to an end?" Fingers crossed.
"What, don't you want to go for a quick swim?" Anna asked with an air of innocence, but from the way her eyes twinkled I could tell she knew exactly what I was thinking.
"If I had, I would have brought a more modest suit," I laughed, throwing it into the open. Vanessa looked mildly amused.
"Why?" Vanessa asked curiously. "What sort of suit do you have?" The way *her* eyes looked when she said that made me wonder if she and Anna hadn't already discussed this, but there was no way of knowing with certainty.
"Oh, just one your sister bought to punish me for never remembering to bring one," I chuckled. Anna grinned, but Vanessa looked confused. Maybe Anna hadn't said anything.
"Let me show you a picture," Anna said with a mischievous grin, looking directly at me as she pulled out her phone and scrolled for a moment. Then she leaned over and showed her screen to Vanessa, who fanned herself exaggeratedly, the same way that I'd seen Anna do before.
"Oh, my stars," she said in a fake Southern accent, and both sisters burst into laughter. I just stood there, more amused than embarrassed, but definitely a little embarrassed.
"That's alright, Charlie, we probably are going to change, I'm getting a little cold," Anna said finally, as their laughter eventually subsided.
"Then why'd you have to show her? And where'd you get a picture?" I asked as she smiled, looking very pleased with herself.
"I've taken a bunch, you look hot," Anna replied nonchalantly. "And because you're cute when you get embarrassed, which is true even though I don't think you have anything to be embarrassed about." Vanessa didn't say anything, which I was grateful for. If she was anything like Anna, and so far, all signs pointed that way, she probably had plenty of jokes queued up in her head. The two women even looked alike, and if not for some subtle differences could almost have been twins.
Like my girlfriend, her older sister Vanessa had light brown hair and a beautiful face with soft features. Her eyes were brown whereas Anna's were blue, and her face was a little narrower, but it would be impossible to hide the fact that they were sisters. Both women wore one of Anna's Riviera bikinis, a swimwear company famous on Instagram for their minimalist suits that left very little to the imagination.
"Well, anyway, can we get some food ordered now? We were waiting for you, Charlie," Vanessa explained.
"Any ideas?" Anna asked Vanessa. "For some reason I'm thinking sausage," she added, unable to keep a straight face. Both sisters started laughing again while I sat down, red-faced but used to Anna's antics enough to mostly ignore it.
"Sorry, Charlie," Vanessa said after she got it together. "If it makes you feel better, I did bring a suit, and she made me wear one of her little Instagram slut ones instead, so instead of a picture you get the real thing," she said and gestured at herself in a deprecating way. I glanced and looked away, figuring that staring at my girlfriend's nearly equally hot sister wasn't a good look at our first meeting.
"That does kind of make me feel better," I joked. Vanessa smiled.
"We're young and sexy and we should dress like it," Anna said with a shrug. I tried to change the subject.
"So, Vanessa, how did the New York shoot go?" I asked. She lived in LA but was visiting us in Orlando before she went back home.
"Pretty great. Had to fend off a photographer who was a little too forward with me, but otherwise no complaints. Not like full-blown harassment or anything, just awkwardly not taking hints, you know?" Anna nodded as though she very clearly knew. "I got a big box of workout sets out of the shoot though," Vanessa added. Anna perked up.
"I'll trade you some of my bikinis for a few sets," she offered her sister. "Who was it for?"
"BRSportswear," she replied. Anna narrowed her eyes.
"Hold on. You gave me shit about modeling thongs for Riviera while you wore those leggings?" she asked skeptically. Vanessa smirked.
"Maybe," she replied coyly. I was lost.
"What's wrong with that company?" I asked curiously.
"Nothing," Anna replied, "but their leggings are famous for making your ass look ridiculous, like the Riviera of gym gear. They scrunch all the way up your ass." She turned to Vanessa. "I want at least two pairs." Vanessa nodded and agreed.
"That's fine, they gave me a lot of them. Just let me get a few photos wearing each of the ones you want before I leave so I can still post later," Vanessa said.
"Deal," Anna said. "So, food?"
***
The Chinese food we ordered wasn't bad, and we ate it in the backyard by the light of the pool and some citronella candles. They'd put on more clothes now that the sun was gone. Anna was wearing a long-sleeved blue T-shirt and black leggings, while Vanessa had put on yoga shorts and a baggy grey sweatshirt.
Empty takeout containers littered the table along with empty hard seltzer cans. I knew her sister, and so I wasn't surprised that she was also very personable, but Vanessa was fun to hang out with. Anna had been right when she said they were very alike; sometimes I felt lost in their conversations because they were almost telepathically on the same page.
"So, Charlie," Vanessa asked after she set down her empty plate, her expression turning unreadable, "what are your intentions with my sister?" They'd been talking about an old high school friend of theirs who'd moved out to LA recently and lived near Vanessa, so the question took me off guard. I couldn't tell if she was joking or serious, so I decided to answer seriously.
"I want to make her as happy as possible for as long as she'll have me," I said simply. "She's the best thing that ever happened to me," I added. Anna blushed but didn't say anything and just gazed lovingly at me.
"Solid answer," Vanessa said back. "You cool if I grill you a bit?" She didn't look like she was asking a question, and I wanted her to like me anyway, so I nodded and took a sip from the White Claw they'd given me. "Anna already told me about your job and how you guys met. Where are you from?"
"South Florida, just outside Lauderdale," I replied.
"How long have you lived here?" she asked.
"Since college," I replied.
"What school?" she asked.
"Ocean State," I said. She nodded.
"The way Anna describes you, you're basically perfect. So why were you single?" she asked, her brown eyes watching me as I answered.
"Broke up with my last girlfriend a couple years ago. We grew apart. Hadn't met the right person after that, I suppose," I said.
"And my sister is the right person?" she asked, still watching me like a hawk.
"Of course. I don't have to tell you she's amazing. She's funny, driven, successful, hard-working, beautiful, and kind," I said. Anna turned a darker shade of red and smiled at me. "Trust me, I know how lucky I am," I added, looking at Anna. I glanced back at Vanessa, who was watching me curiously.
"That's enough, don't you think, V?" Anna asked. Vanessa nodded.
"Sorry, Charlie, just a protective older sister. Answer like that when my parents meet you and you'll win them over, no problem," Vanessa said encouragingly. Anna rolled her eyes but looked happy that her sister was looking out for her.
"Now that that's out of the way," she said, playfully giving Vanessa a side eye, "Charlie, tell us all about your first day!"
"Not much to tell," I said, sipping my drink. "I got a tour of the whole property and met some of the departmental managers. Mostly half days for a while, it'll be slow, just getting acclimated." Anna seemed genuinely thrilled anyway. Vanessa didn't ask any questions, so I assumed Anna must have given her the background.
I faded back after that, letting them catch up and only occasionally interjecting with a quip or a question to help me follow along. I gathered that with how busy they both were, these moments were few and far between. I was just happy to be there, enjoying watching Anna and her sister happily chatting away. I glanced at my phone briefly, only to find it was getting late and I needed to get home.
"Well," I said during a lull in their conversation, "I've got to get going, work in the morning."
"You can't stay?" Anna asked, looking a little saddened.
"I didn't think to come prepared, so I have to get home so I can get out on time for work tomorrow," I replied. She nodded, not thrilled but understanding. "It was very nice to meet you, Vanessa."
"Same, Charlie," she said, and as I stood, she gave me a quick hug.
"You're free tomorrow, right, Charlie?" Anna asked. "We're thinking of dinner with my parents. Will you come to meet them?"
"Of course, just tell me when and where, I'm working until five or five-thirty," I told her.
"Awesome. Come on, I'll walk you out," Anna said, taking my hand. Vanessa smiled and waved as we entered the house.
"Well done, Charlie," Anna whispered.
"What?" I asked.
"She liked you," she replied, her volume increasing as we got away from the back door.
"How do you know? We didn't exactly talk much, I mostly just observed tonight," I replied.
"Well, for starters, your responses to her questioning you were so sweet, and I loved them. Also, she's never been that welcoming to anyone I've brought around, even just friends that are guys, like she's never trusted any of them. And thirdly, you made her smile with your little jokes a bunch of times, which she wouldn't have done if you annoyed her or if she didn't like you. Trust me, you won her approval," she declared.
"Well, good news then," I said. I had a new spring in my step from that as we got to the front door. If I was truly going to end up with this girl, winning over her family was of the utmost importance. I kissed Anna, and she smiled against my lips before kissing me back. Anna started walking again, leading me out to my car instead of saying goodbye on the porch.
"I wish you didn't have to go," she said. "I've had such a nice day; it's a shame I don't get to end it with you in bed."
"Sleeping?" I asked, with a knowing grin.
"Sure, we'd have to rest after the pounding I'd get from you," she said, smiling cutely. I smiled back. "Stay with me tomorrow night?" she asked.
"Of course," I said, "I'll bring a bag."
"Awesome," she grinned and kissed me against my car door. "I love you, Charlie," she whispered.
"I love you, Anna," I said softly, and we kissed once more, our lips locking together as we pressed against each other in the cool breeze.
***
The next morning, I woke up early for my temporary routine, training and being trained. After a pop-tart and coffee, I showered and got dressed. Having hung out with Anna in a bikini last night and then gone home alone, I was unusually horny, and I may have thrown on the video she sent me of her blowing me and jerked myself off in the bathroom before I showered. Anna had made comments before about being horny all the time since we met; it seemed the same thing was happening to me. If I went one night without her, I was in desperate need of release even when I was short on time in the morning.
I grabbed my overnight bag and headed out. As I walked to my car to head to work, I had a teasing thought and decided to send Anna a text.
"Good morning, gorgeous. How many times did you touch yourself without me last night?"
"Good morning, Prince Charming," came the first text. "How did you know?" read the second, accompanied by an angel emoji.
"Because I went to bed without you and then I had to spend some time watching our home video this morning, so I assumed I wasn't alone," I replied.
"Fuck, I should have thought of that," she texted back. A second message followed. "And fuck, that's hot. Did you jerk off watching me take care of you?"
"I did, do you want to know when I came?" I asked, loving how quickly she got into sexting.
"Tell me," came the reply, accompanied by a panting emoji. I smiled.
"When you came on my fingers at the end of the video," I told her.
"Fuck, I'm so horny right now," she replied.
"Is Vanessa up?" I asked.
"I don't think so," she replied.
"Then you've got some time. Touch yourself again."
"Is that an order?" she asked. I typed out a reply as I got to my car -- "If you want it to be," I wrote, but then thought better of it. That's not what would get her going.
"Yes," I sent back and started up my car to drive to my old job.
It was a short drive, and I was early enough to beat any traffic that was going to appear on a Wednesday morning, so it didn't take long. Neither, it seemed, did Anna. My phone buzzed as I parked, and I unlocked it to read the messages. There was a picture of her from the chest up, her tits spilling slightly to the sides as she lay on her back and smiled up at the camera. Her chest and face were a little flushed and her hair splayed out behind her head and her expression was happy and satisfied.
"That face when your boyfriend just made you cum with a couple of text messages," she captioned it.
"Show me," I replied.
"Charlie, you dirty boy," she replied. That message was immediately followed by a close-up picture of her wet, swollen, and flushed pussy, her two fingers spreading her lips for the camera. My cock sprung to full attention.
"I might have gone too far teasing you this morning," I sent. "Now I have to go to work hard."
"I'll take care of you tonight, whatever you want," she texted me. Thoughts of everything I might have wanted swirled unbidden through my mind.
"Not helping," I said back and was rewarded with three crying laughing emojis.
***
We didn't get through as much training as I'd planned for, because both Becky and I spent most of the half-day I had at the desks checking in an odd rush of guests for a Wednesday morning. By the look of it, there was some kind of hockey tournament in town, because every family had massive duffel bags, hockey sticks, and children around 13 or 14 years old. We weren't hosting anything at this hotel specifically, but whenever a major event took place, we got extra people who wanted to stay at an Obsidian hotel instead of wherever else so they could earn their points.
I got Becky through a little bit of the HR and hiring process stuff, but we'd be going through more of it tomorrow. She was a quick learner, so fortunately the entire day wasn't wasted, only most of it. I grabbed a sandwich from the hotel café on the way out and headed to the Gateway for my training shift. As I got into the car, I received a text from Anna.
It was a close-up image of her perfect tits. The two perky breasts sat high on her chest, barely sagging at all for the natural endowment she had. Her pink nipples were hard and practically begging me to suck them, or they would have been if I was with her.
"Still horny. Paint these later?" she texted.
"Like Jackson Pollock," I replied. "How are you doing?" I started up my car again and headed out of the parking lot. I didn't check my phone until the first red light, and when I did, she'd texted back already.
"Awesome, my parents came over early to spend the day with both of us, and I told them I'd be bringing you to dinner. Vanessa told them they'd love you. That's also why I had to sneak into the bathroom and take a quick closeup pic for you, no time for a well-thought-out shoot," she said.
"You could have just not sent one lol, I'd survive," I sent back. At the next light, I checked my phone again.
"The day I don't get you hard on your break is the day I've failed as your girlfriend," she declared via text, and I laughed.
"Well, it is not this day," I said.
"For Frodo!" she replied, catching my reference. And she calls me a nerd, I thought, shaking my head.
***
The same thing was happening at the Gateway, with a load of families checking in on what was normally the slowest day of the week. Same bags, same hockey sticks. My temporary boss who was training me as his replacement, Rick, informed me that it was a regional tournament that had players from all over the southeast being hosted in Orlando. Then he threw me onto the front desk with a half dozen other overwhelmed staff members and had the guest services manager train me on the system under pressure. I had met Tony the day before, and he was still as jovial as he was then, even while the crowds checking in bore down on the desk like stampeding wildebeests.
Fortunately, there wasn't that much difference between Gateway's check-in process and the one I'd used for years at the Greenfield Suites before getting this job. I was a quick study, and within a half hour, I was operating mostly independently, helping check-in guests with the other staff. I hoped they would appreciate seeing that I could do the job since I'd be their boss in a week and a half. Derek, the guy working next to me, seemed happy to have the help. He presented a customer service face to the guests, but when he turned around, I could see the exhaustion seeping in. Ah, hospitality.
Around two hours in, the crowds reached a lull -- I guessed that whatever tournament was taking place started that evening, and only a few unlucky stragglers were still checking in while the rest of the families headed off to whatever ice rinks were hosting the event. Rick collected me, likely having been watching from the one-way window in his office across the lobby.
"So, I'm guessing you learned how to operate our guest management system?" he said with a smile, his dark skin crinkling around his eyes, clearly amused with how tired I looked.
"Yeah, I think I got it. At least nobody complained. I hope," I added.
"Tony was impressed, he came to let me know you were good on your feet before he left for the day a bit ago," Rick said. He looked smug, which I found odd until I realized he was feeling vindicated in recommending me for this role.
"I'm glad," I said. "What else do we have today?" I asked.
"Just a quick meeting with Accounting, and then another with IT," he said.
***
Well, I thought to myself, that was strangely predictable. I wasn't usually one for stereotypes -- all people are different people, after all. And yet, after meeting with Mike from Accounting, and Ron from IT, I felt like maybe the caricatures of those jobs in Hollywood movies were more accurate than I'd have guessed.
Mike was a nice guy, albeit boring. He didn't have much to say about anything except work when I tried to make small talk, and when he did speak it was kind of awkward and stilted. He walked me through his day-to-day and went through the important ledgers he maintained, and I'm assuming some of it was important. I didn't get any of it, though, because I was unbelievably bored listening to his voice drone on and on about T-accounts and bookkeeping adjustments. After a while, Rick took pity on me and thanked Mike for his time before guiding me back into the utility corridors to find the server room and IT offices.
"Get any of that?" he asked me.
"I think I got it," I said, unconvincingly. Rick laughed.
"No, son, you didn't, but that's alright. Mike is very good at his job and has passed every corporate audit with flying colors, so don't worry about it. I just wanted you to meet him and see what I meant when I say that now."