From Hookups to More... Pt. 05

The next day, I stayed at work an extra couple of hours. It helped because that gave Carly, Cassie, and Jayda to run into the city as well to grab some of their things for their stay, but also, it helped me progress some work files that had sat on my desk for too long. The company was looking at expanding, and it was on me to figure out where to go next. I had zero idea what I was going to have for lunch the next day, let alone where I thought the company should go...

Kylee texted me to say she made it to her work convention. She even took the time to send me a risqué bathroom selfie at what I assume was a high-class restaurant.

'Fuck,' I thought. 'I know the three girls are there to keep me company, but they aren't her...'

As tempted as I was, I decided not to purchase plane tickets to spend the week with her instead. I trusted her, and she left me three of her sexiest friends to play with while she was gone. But, that didn't stop me from looking up the price of tickets...

***

When I got home, Carly, Jayda and Cassie were all in the theatre room watching a movie. I was about to make myself supper when I noticed a plate already made for me at the end of the table. With a smile, I walked over to the table and began eating.

As I was scarfing down my relatively-cold meal, I scrolled through my phone, but eventually that led me to Kylee's Instagram. I was feeling something about her I had never felt in a woman before.

She must have felt the same way, because my phone started to buzz. Kylee was FaceTiming me.

I answered, and Kylee had her blouse open. She was laying on the bed, no bra on, panting heavily. She was fingering herself.

"Hey Daddy," she said through the phone. "I can't stop thinking about you," a naughty smile formed on her face.

"So much for waiting until you got home," I joked. "I may have to punish you when you get home."

She let out an audible moan. "Mmm, Daddy, I can take it. I'll let you do anything you want to me. I'm such a bad girl." Her eyes glowed in lust. "Pull that cock out for me, Daddy."

I unzipped my pants. My cock was already throbbing, so when I popped it free, Kylee's eyes widened. Her panting got faster.

"Mmm, I'm imagining that cock inside me, in all of my holes..." Kylee muttered. She showed me her pussy as her hand feverously fingered herself. "I don't know if I can make it a whole week without it, Daddy."

"I could come down there," I offered. "Or, I can sit here, and tease you, and make you watch as one of your friends takes my cum. Which would you prefer, baby?" I said with a smile, rubbing my cock slowly for her to see.

She stopped mid moan. "Wait, you'd come down here?"

"I mean, I guess. I can work remotely for the week," I explained.

"What about the girls?" she asked.

"I haven't made them into slaves yet. They could sit and watch the house and entertain themselves. They're watching a movie right now."

"Would you... want to come here? I've never been this horny. And I don't want another cock..." her eyes fluttered shut.

I checked flight schedules again on my phone. I knew there was a direct flight that left in two hours, and if I left right away, I could probably catch it.

"I can be there in five hours or so. Would you stay up?"

Her eyes widened in excitement. "Anything for you, Daddy."

I put my pants back on and hurried to the theatre. I hit pause on the screen, which startled Carly, Jayda, and Cassie, who were nestled together, wearing matching onesies that clung to their bodies. Cassie's face emerged from Carly's cleavage, so it's not as though they were watching much of the movie anyway.

"Girls, I'm going to Kylee. You can entertain each other while I'm gone. Don't break anything."

"But, I thought this was our week to spoil you..." Carly said with a pout.

"Spoil each other. Orgasm until you can't function, I don't care. Kylee gets first dibs, and I want her. Nothing against you three."

They all laughed.

"You be with her. We all know you two love each other," Jayda said. "I'm surprised you're not there already, honestly."

After leaving the theatre, I packed my bag, and headed for the door. The SlaVR stared back at me from the kitchen table. With a smile, I left it on the counter. I had a feeling I wasn't going to need it.

***

After grabbing my passport and work laptop -- both of those things I kept at work -- I made my way to the airport. As I parked in one of the parking lots, I was already getting snapchats from Kylee. Some of them would have earned her thousands on OnlyFans.

"I'm on my way. Behave until I get there," I texted her. She just replied with a devil smiling emoji.

I made my way to the ticket counter and purchased my ticket. I opted to not check a bag, and made my way to the security line.

My flight left in 45 minutes, but security was moderately busy. I got through the line and made it to the front desk.

"Reason for visiting the U.S.?" The clerk asked. She had a strong accent, possibly from New York. Her name tag indicated that her name was Denise.

"Pleasure," I said. I smiled as the thought of Kylee laying on the bed naked appeared in my mind.

I had to snap out of it quickly as Denise fired multiple questions at me. All of the standard stuff. She gave me back my passport, and not-so-sincerely told me to have a nice trip.

I made it to my gate with a few minutes to spare, when it hit me that I should probably let my employees know I was dipping out for the rest of the week.

I started typing out an email on my phone when I heard a familiar voice from in front of me.

"Fancy seeing you here," the female voice said.

I looked up to see one of my exes. Hailey and I ended on good terms, but she made it apparent she wanted me back. Too apparent.

"Have you been avoiding me, stud? You haven't texted me back."

"That's how blocking a number works," I snapped back. "Hailey, we're through. And I'm literally on my way to go see my new girlfriend."

She stumbled back. "Boy, don't you move on quick," she said putting her hand on my chest.

I rolled my eyes. "We broke up two years ago. I know you've moved on too."

"Actually, I uh.. I--" Hailey started, but was interrupted by the intercom. I had to get going.

"That's my flight," I said as I grabbed my computer bag and backpack.

"Are you still up at that place on the hill?" She said.

"Yes, but don't go there," I said. "I have people watching it for me."

She bit her lip and gawked at me. "What would you do if I did?" A playful smile grew on her face.

"Hailey, please." I muttered as she started to laugh.

"I'll see you later, Ry," she said with an overly-flirty smile as she turned on her heel and walked away. I hate to admit, but I did watch her ass sway as she walked. It was one of her finer qualities.

I boarded the plane, and looked out the window. Booking a flight without getting a window seat never felt normal to me. I have no idea why, maybe it's the sense that you can look down and see yourself moving. With how dark the fall sky was that night, there was hardly any benefit.

I resumed my work email from my phone while the rest of the passengers loaded onto the plane. I then rested my eyes for a moment. When I woke up, we were taking off. And I couldn't sleep a wink.

'Typical,' I thought.

***

Thirty minutes after landing, I hailed a cab and gave him the address for Kylee's hotel. I'm not sure why, but I was starting to get butterflies, thinking about meeting up with Kylee in a city I had never been before.

It was only 15 minutes, but it felt like hours. With a screech of the tires, we arrived in the front of the hotel. I paid the driver, and made my way inside.

Kylee's work was sparing no expense for this hotel. She was in an executive suite on the top floor. I messaged her to let her know I had arrived, and made my way into the elevator.

On my way up, she texted me back.

"Your slave awaits, Master."

GULP.

The elevator stopped at the top floor, and opened. Kylee's room was at the end of the hall, so I rushed passed the other rooms, but quietly, not trying to wake anyone.

I knocked softly on Kylee's door, but someone else answered.

"You must be Ryan. I'm Lin, your room service attendant," Lin said. The Asian woman offered a warm smile. "Kylee asked me to assist her in welcoming you to the room."

As she stepped out into the hall, she closed the door behind her.

"May I see some I.D., just to make sure?"

Still a little dumbfounded, or tired from the flight, I fumbled around for my wallet to pull out my license. After she looked at it, she nodded.

"Very good. You're a very lucky man, sir," she said with a smile. "Kylee paid me graciously to help her prepare for this evening."

"What's going on?" I asked. I wasn't annoyed, but I was getting there.

"Kylee instructed me tie her to the bed. She has a gag in her mouth and a blindfold on her eyes. She is also completely naked," Lin whispered quietly. She then handed me a room key. "She told me to tell you she is all yours. She also told me that if you have anything you'd like that is not in the room, I am to get it for you."

"You mean, you're going to be in there?" I asked.

She nodded and smiled. "Kylee gave me distinct orders. I am to make sure you have everything you need." She touched my arm softly while looking up at me warmly.

'There's no way she works at the hotel,' I thought to myself.

I swiped the card, and opened the door. Sure enough, there was Kylee, sprawled on the bed, wrists tied tightly to the headboard, ankles tied to the corners of the king-sized mattress. She was playfully kicking and struggling, grinding her ass into the bed to arch her tits into the air. There was a single light on above Kylee, it made her look like she was glowing.

With a smile, I entered the room and set my bags on the desk, across from the bed. I stroked my cock through my pants, and grabbed Kylee's leg. She squirmed some more.

In the corner of my eye, I saw Lin unbuttoning her shirt. I turned to her as she freed a massive pair of tits from the cotton fabric of the shirt, and watched with wide eyes as she threw the shirt to the ground. Her black bra matched her thong that was revealed after she removed her pencil skirt, but her high heels remained on. She turned to me and smiled. "Do you like what you see, sir?"

"I take it this is not a typical service the hotel offers," I said. I could hear Kylee giggle through her gag as Lin smiled.

Lin shook her head. "Kylee hired me to ensure both of you experienced the most amount of pleasure. If I may, would I be able to suck your cock before you fuck her? I wouldn't want her to be in pain," she said with a naughty smile.

I unzipped my pants. "You may, but I want her to watch," I smiled, while smacking the inside of her leg, causing her to yelp through the gag.

"Of course, sir," Lin replied softly. She made her way to Kylee and I, and removed Kylee's blindfold. Kylee's green eyes burned with arousal. She tugged at the ropes as she saw me, then looked at Lin, who was unbuckling my pants. Her eyes widened towards me as I stuck two fingers deep inside her pussy as Lin freed my cock from my pants.

"I must say, sir, I am impressed," Lin said while stroking my cock. She then slid her mouth onto it as I fingered Kylee.

Lin bent over to suck my cock, which gave Kylee a good view of her head bobbing on my cock, as well as her tits shaking while she bobbed her head. Kylee's eyes soon rolled to the back of her head as she came hard on my fingers.

I didn't stop or slow down, and neither did Lin on my cock. I popped my cock free from Lin's mouth.

"Would you eat her pussy? I think she'd love that, wouldn't you?" I turned to Kylee, and slapped her pussy lightly, driving her insane.

"Of course, sir." Lin said as she caught her breath. She made her way to the end of the bed, and stuck her tongue into Kylee's pussy.

I smiled and looked up at Kylee. Her eyes were shut tightly as she came closer to a climax.

I removed her gag, but shushed her. She obeyed, but panted heavily.

"What has gotten into you?" I asked with a playful smile.

"I'm your hypno-slave, Master. I'll do anything you command," she muttered back.

Lin lifted her head and acknowledged my obvious confusion.

"So, my actual day job is a hypno-therapist," she explained, while lightly fingering Kylee. "Kylee expressed interest in hypnotizing herself for you while she was away. It started off slowly this afternoon, but she became fully engulfed in the trance by the time you got here. She wanted to show you what her being mindless was like. You're a very lucky man, sir. Most of my clients hire me to force their partners into submission without their knowledge."

"Is this permanent?" I asked.

Lin shook her head. "The effects lift once you cum inside of her. It could be her mouth, buttocks, or vagina. But she needs your cum, literally."

Kylee mindlessly swayed her head back and forth as she looked at me and took penetration from Lin's tongue and fingers. I pinched her hardened nipple as she let out a happy sigh.

"Will she remember anything?" I asked. Lin again shook her head, but didn't lift her head from Kylee's pussy.

I stuck my cock inside of Kylee's mouth, as she happily bobbed her head.

"So, why are you helping us have sex?" I asked Lin. She lifted her head.

"I want to see what happens to my clients, especially if they're from out of town. You're definitely one of my favourite couples so far."

"So, you basically offer yourself to couples to have sex with them?" I asked. "I don't mean to sound rude, but like, isn't that weird?"

"I suppose it is. But very rarely does the man's cock insert my vagina. I'm here for the stimulation. I know what's going to get her to cum hard, and I know how to help you keep going long after I leave for the night."

My eyes widened in intrigue. "So, we could literally fuck all night?" I asked.

Lin smiled. "Yes, you could. If you take the training I offer together, you'll be able to regenerate cum non-stop. It's safe to say she loves your cum, even when she's not under this trance. She told me about the SlaVR you guys have been playing with. While I don't condone it, it sounds like you are using it safely on her and your supposed harem."

Kylee mindlessly continued sucking my cock while I pondered.

"We don't have to decide tonight, right?" I asked.

"Of course not. You have better things to do right now than talk to me. Your Slave is waiting," Lin got off of the mattress. I popped my cock out of Kylee's mouth and moved to the end of the bed.

"Please, Master. Fill my pussy. My mind and body is all yoourrssss..." Kylee trailed off as I began fucking her.

Lin stood behind me while I pounded my girlfriend's pussy. Kylee moaned quietly, as per my order.

"Untie her legs," I ordered Lin.

Lin quickly began removing the bondage from Kylee's ankles. As soon as Kylee's legs became free, she tucked them behind my legs, locking herself and pulling me into her body.

"Thank you Master, I want you deeper," she begged. "The deeper you cum inside of me, the happier your slave will be."

I smiled as I held her hips and continued fucking her.

I wasn't close yet, but Kylee was cumming like a waterfall on my cock. It was hard to tell when her orgasms stopped. Her mind was lost, filled with pleasure while I fucked her.

"Would you like me to help you finish, sir?" Lin asked.

"What did you have in mind?" I replied.

Lin pulled her massive tits free from her bra, and walked towards Kylee's mouth. Kylee began sucking on Lin's nipples, and Lin sighed deeply and smiled.

"Watch as your slave sucks on my tits, sir," Lin looked at me. "She is completely consumed in pleasure. Not a thought in her mind other than you and me."

"That's so fucking hot," I muttered as I increased my pace.

Lin let out a moderate moan as Kylee continued sucking on her tits. She looked at me.

"I want you to finger yourself, Lin," I said as her smile grew wide.

"Thank you, sir," she said with a smile. Her hand reached at her pussy under her thong. She rubbed her pussy quickly and moaned out, closing her eyes, and leaning her tits into Kylee's face.

I could only see one half of Kylee's face, but her eyes were closed as well. Her mind was overloaded with sexual pleasure.

Lin lifted her tits off of Kylee's face.

"What do you need, slave?" I asked Kylee, holding her legs in the air as I fucked her.

"I need Master's cum. Please, Master. Fill your hypno-slave," she pleaded. "I'll do anything for your cum."

I let out a long moan as I came, which sent Kylee and Lin both into a frenzy. Lin muttered out and shook as she came, and Kylee's eyes rolled to the back of her head as she gasped, and froze before letting out a delighted scream as I pumped my load inside of her. I let my cock sit inside of her pussy as she smiled up at me.

"Mmm, thank you, Master," she said with a smile.

Lin turned to me, with red in her cheeks. She looked embarrassed. "I don't normally orgasm that loud in front of clients, I'm sorry."

"Don't be," I said. "It was really hot."

Lin smiled as she lifted her bra over her tits once again. I pulled out of Kylee as she laid there, smiling with her eyes closed. "She's going to be alright, isn't she?" I asked.

"Oh, yes. She's coming out of her trance. She will be just fine," Lin said. "I've left my card on the table in case you both want to meet up again before you leave. It was a pleasure meeting you." Lin quickly got dressed and left. I pulled some sweats out of my bag and threw them on, and saw Kylee looking back at me.

"I'm so glad you came," she said. "I love you."

***

Kylee hid her rope-burn from the night before with a long-sleeved shirt and dress pants that covered her ankles. She looked incredibly sexy as she got ready for the second day of the event she was attending for work.

"I should be back at the hotel around 6:00, we can grab some food then if you want," she said as she looked into the mirror to apply her makeup. I just stood in the door frame and admired.

"I'm good with whatever you want to do, babe," I said. "You spoiled me, last night. I think you should get something you want tonight."

She turned to look at me. "You're here, aren't you? That's what I wanted," she said with a laugh. "I'm glad you got to remember everything last night. I don't even remember our FaceTime. I was tranced by then."

"I figured it was weird. You called me Daddy," I told her.

"Well, I don't have to be under a trance for that if you want, Daddy," she teased.

I just laughed and gripped her hips. "Come back here tonight, and you decide what we do. I'm just here for the ride baby." I smacked her ass and kissed her cheek from behind her. She let out a low gasp.

"I... don't have time, but I want to..." she said as she looked at me through the mirror.

"Save it for tonight, Kylee," I smiled. A few minutes later, she was out the door.

***

At lunch, I ordered room service, and checked in on the girls. Carly answered my FaceTime, wearing a lace bra and a flushed smile on her face.

"Things going well, I assume?" I asked.

"Oh, YES!" She exclaimed. From the background, I could tell she was in one of the bedrooms. She was rocking her hips on someone's mouth, but I couldn't tell who.

"I'm just checking to make sure everything is okay," I said.

"Mmm, don't worry Ry. We have it all under controllll...." she trailed off, as I could tell she was cumming."

"I'll check in later," I said as I hung up.

Room service arrived a little later, and I ate while I continued to work from the hotel room.

The place was easily bigger than Kylee's old apartment back home. It had a lounging area, which is where I was seated, as well as a separate area for the bed, TV, and bathroom. It even had an in-suite kitchen and minibar that was part of the lounging area. I was never one to stay in super nice hotel rooms if I was going somewhere, but I was sure glad Kylee splurged. That morning, she told me the company only covered 30 percent of the room, but she wanted her last trip with this company special, so she paid for the upgrade out-of-pocket.