From Hookups to More... Pt. 01

Kylee Miller was a sexy freak.

I discovered that early on when we met online. We met on a dating/hookup site, and got to talking. I was still reeling a bit after a recent break-up and I wasn't all that interested in a relationship, but I made my intentions clear right from the start. Kylee agreed, and we met up for the first time on a sunny Saturday in March.

The sun was starting to melt away the snow, and it was hovering right around that melting point. Kylee definitely made the temperature go up a few degrees herself. a stunning brunette with blonde highlights, ample-sized breasts, and green eyes that seemed to glow. What made it not fair was her ass was also phenomenal.

I like to think I was an attractive man, standing at 6'2", I always kept my facial hair at stubble length, and while I didn't pay much attention to my hair, it always seemed to look nice. My naturally-tanned skin seemed to be selling factor for women, as well as my hazel eyes. I could have stood to lose some weight, but by no means would I have been considered fat. Unless they have tons of money, fat, ugly dudes don't get girls like Kylee, so I must have been doing something right.

We met up for a Saturday brunch in the downtown of a busy Canadian city. Kylee smiled as she walked to the table as I was already seated.

"You look even better in person," I said as I stood up and offered her a soft hug.

She took in my embrace and replied;" I could say the same for you."

We both sat down, smiling at each other and making awkward small talk as we waited for the server to take our orders. Kylee and I decided early that our phones should be set down on the table with the screens down. There was nothing shady about it, it was just a matter of making sure they didn't become a distraction as we learned more about each other.

Kylee was a fashion designer. She showed me her Instagram page, and noticed she modeled some of her own clothing. I smiled as I scrolled through, admiring some of the more risqué items she wore.

Kylee learned I was more on the business side of things. I ran an office supplies chain that was quite successful. It didn't have the glamour that some jobs have, but it paid for an expensive taste. At 26, I was already making $320k per year. While I talked at work, Kylee nodded politely, and smiled as I finished.

"So, you told me you just broke up with someone. What happened?" She asked curiously.

"I'd rather not get into it," I said, leaning back into the wooden artistic chair I was seated in. "I'm not one to badmouth or drag someone's name through the mud."

Her eyebrows raised. "Oh come on, Ryan. I'll tell you about my crazy ex if you tell me about yours," she smiled.

"If we're telling crazy ex stories, we'll need more than just brunch for that conversation," I said as we both laughed.

"I have nothing else to do today," she smiled and winked.

I cracked and told her about Elizabeth. I explained that Elizabeth was really sweet and caring, but lacked in certain areas. Her sexuality was plain for my tastes, and she was very unwilling to explore. We ultimately decided it was time to go our separate ways about a month ago.

Our food arrived, and Kylee told her story as we ate.

"My ex, Mark, was nice, but that's about it," she said as she dug her fork into some cantaloupe. "He bounced from boring job to boring job, and just didn't try hard enough to keep me. And if I'm being honest," she leaned in and whispered, "his dick was like, 3 inches, max."

My eyes widened. Poor guy.

"Well I hope you don't find office supplies boring," I joked as she smiled wide again.

Then I felt a foot under the table on the inside part of my leg. I looked down, and saw Kylee's foot inching closer and closer to my crotch.

I was definitely not a three-incher by any means, but I was a grower. It didn't take long for me to grow at full length. Kylee rubbed my cock through the outside part of my pants and she gasped.

"Oh my..." she smiled.

Luckily, we were in a corner booth, so no one could see what she was doing. But my face was turning the same color as the bacon on my plate. She wanted to do that? In public?

She put her foot down. "I look forward to exploring that later," she said, sticking another piece of fruit in her mouth.

***

Our brunch date ended, and I took her back to my place. Kylee had cabbed over to the restaurant, and I drove one of my luxury cars. She was definitely impressed.

As we pulled up to my house, she gasped again.

"This definitely beats the one-bedroom studio I live in..." she trailed off.

My four-bedroom house was pretty damn nice. Not to brag, but there's certain places guests can get lost pretty easily, it's that big. I worked with a developer to design it, and made sure it had all the cool shit, from a full-service bar in the basement, theatre room in the main level, walk-in closets in every room, and probably my favourite feature, a garage to store my three vehicles.

I parked the black BMW in the middle between my matching black Ford Mustang and my black Kia Sportage. I kept the SUV for winter driving, and the other two for show.

Kylee followed me to the front door before I decided to give her the grand tour, I let her walk into the house first, giving me a great view of her ass in leggings.

She let out an audible gasp as she spun slowly around the main foyer, looking at the big living room off to the right, the high ceilings above, the massive kitchen straight ahead, and the long hallway leading to the theatre room on the left. I just stood back and smiled.

"Need a roommate?" She asked sarcastically, but I could sense part of her wasn't joking.

"It does get pretty lonely around here," I admitted. "It's almost paid off anyway. High salary, with some inheritance from my parents..." I trailed off. That was still a tough subject.

Kylee's face went from joy to apologetic.

"Really sorry to hear," she said, sounding sincere. She held my arm softly. "I lost my parents not too long ago either. As an only child, it was hell trying to sort through everything myself."

"Trust me, siblings don't make it any easier," I scoffed, remembering how my two sisters fought and clawed for more and more, all for them to blow it on Cocaine and one hell of a party.

Trying to change the subject, I offered her a tour. I showed her the living room first, which was more open concept, with seating along the outside of the room. Next was the kitchen, with a large island in the middle, stove against the wall and a large sink that had multiple water features. The whole counter was black, but it looked really sleek beside the white tile that laid on the floor.

Down the hallway, we made our way to the theatre room, with three rows of couches for seating, all of which having room to recline. The back couches didn't match the first two rows.

"Had to get what the furniture store would get us," I explained.

We made our way up the linear-staircase and I showed her each of the four bedrooms, including my Master bedroom. Her favourite part wasn't the California King bed in the middle of the room, but the showers.

"You could play hockey in this thing," she joked.

We made our way downstairs using the spiral staircase on the other side of the house. The spiral was the only way to get to the basement, which featured a bar with three different kinds of beer on tap, as well as a fridge stocked with bottles of the beer I didn't have in a keg. There was also plenty of hard alcohol on the shelves. I made my way behind the bar, which glowed in a variety of colours in the otherwise dark room.

"What can I get you?" I asked, whipping a white towel over my shoulder playfully.

"Rum and coke," she smiled.

"Spiced, white, or dark? Got options here," I said.

"Let's go spiced," she replied.

As I scooped the ice and mixed the drink, she sat across from me on a leather barstool. I handed her the glass, setting a coaster down before it hit the counter. She took her first sip and smiled.

"This place is phenomenal. I never want to leave," she joked.

I just smiled. "It was a lot of work to put it together, I'll say that much."

"Is that the end of the tour, or do you have more to show me?" she asked, as she took another long sip.

"There is one other room, but it stays locked. No one ever goes in there." I nervously polished a glass and organized behind the bar.

"What's in there? I'd love to see it." She tipped back her drink and set the glass back down on the coaster.

I looked back at her. "Are you sure?"

She gave me a surprised look. "It's not like you're keeping dead bodies in here, are you?"

I pulled a set of keys out of my pocket. I turned on the lights for her to see the full downstairs. To my right, her left, passed the stairs, there was a hallway. The laundry room was the first door, but down the short hallway was the room she wanted to see.

Kylee followed me down as I inserted the key into the bolt lock, and opened the door. Inside was a makeshift sex dungeon of sorts. There was a queen sized bed in the middle, all sorts of BDSM whips and paddles along the walls, and a lot of restraints that lined the countertops. I bit embarrassed, I turned back to Kylee, who looked shocked as she slowly walked into the room.

"I think I have a new favourite room in your house," she said. I had to make sure I was hearing right, but she smiled. "I love this shit. Why have boring sex, right?"

I smiled. "That's what I think, but some people really hate this stuff."

She shook her head. "Not me. I want to try it all..." Kylee trailed off as she continued looking at everything in the room.

I smiled and walked up behind her. "No time like the present." I held her hands behind her back, as she closed her eyes and gasped.

"Red means stop, yellow means slow down," I explained.

"Yes Sir," she muttered.

Already, I knew this was going to be good.

"Take off your clothes, pile them up near the door," I ordered, letting go of her hands.

"Yes Sir," she repeated. She quickly removed her sweater, revealing a large set of breasts. Next to go was her bra. Then, she slowly peeled off her leggings, revealing she wasn't wearing any underwear underneath. She set the clothes on the floor near the door, and turned back to me.

"Anything else I can do, Sir?" She smiled.

"Crawl to me," I ordered.

She quickly dropped to her knees. I removed my shirt and started unbuckling my belt as she crawled to me. She arrived just in time to unbutton my pants, and slide the zipper down.

My cock was throbbing. I had never seen someone so into submissiveness like Kylee before. She pulled my underwear down and smiled as my 9" cock greeted her.

"I think you're glad I came over," she smiled.

"Would you like to suck my cock?" I asked.

"Mmm, yes Sir," she moaned. "Please let me taste you."

I gulped. "You may."

Kylee immediately began sucking my cock. I couldn't fit in her mouth, but damn it, she tried to stuff it all in. She licked the shaft up and down, and stroked my cock as she sucked on my balls.

"Put your hands behind your back," I ordered.

She put them behind her back as she continued to suck my cock, but it didn't last long, as she found herself reaching with her right hand to stroke me off while she sucked. I pulled out of her mouth as she panted.

I grabbed the first pair of handcuffs I could find on the counter. I knelt down and put them on her, and Kylee mewled.

"I'm sorry for disobeying, Sir," she pouted. "Please forgive me."

I lifted her up by the hair and she gasped and giggled. I led her to the bed and pushed her onto it.

I stood behind her and rubbed my cock against her damp pussy. She struggled with her hands in the handcuffs.

"Please, Sir, give it to me."

My cock slid into her tight pussy. She let out a loud moan, and didn't stop as I fucked her from behind. She moaned and shrieked as I felt her squirt on my cock within minutes of me fucking her.

"I'm sorry for not asking permission to cum, Sir. Your cock is fucking me so gooood..." she trailed off as another orgasm approached.

"I never ask anyone to ask me first," I said, while panting. "Just know I always finish on your face or in your pussy."

She turned back to me and smiled wide. "I like your style," she said as she came again on my cock.

She moaned and moaned as I fucked and fucked. Her hands were still handcuffed, so I grabbed onto them and pushed my cock deeper. I felt her pussy tighten on my cock and she squirted hard enough to push my cock out.

"I'm sorry, Sir. Please continue if you want to," she pleaded.

"On your knees," I ordered.

She squirmed to the floor and knelt at my feet. Her face was in my direct line of fire as I stroked my cock.

"Fucking feed me, Sir," Kylee begged. "Spray it all over me, I can take it." Her eyes flashed in excitement.

Finally, I groaned and came, all over her face. She moaned stuck her tongue out, trying to catch strand after strand. My cum was dripping down her neck and onto her tits by the time I finished.

"Thank you, Sir," she said. "You taste so yummy."

I unlocked her handcuffs and she immediately took her right hand to scoop the rest of my cum into her mouth, giving me quite the show.

***

The next time we met up was the Wednesday after our first time. Kylee and I decided I should see her place.

She lived alone, and that's a good thing because her studio apartment was tiny. Kylee didn't have much for possessions, but her living room had to double as a closet, as she had a clothes rack full of clothes sitting beside the couch.

"A fashion designer always has to look good," she said with a smile.

Instead of eating out, Kylee made me supper. She didn't tell me she was a cook, but it was apparent when she brough out a chicken fettuccini alfredo.

'My God this is good,' I thought to myself.

As if she read my mind, Kylee smiled. "Imagine what I could do if I had your kitchen."

After supper, I helped her do dishes, which to her point, were trickier due to the size of her kitchen. I was constantly bumping into her, but we smiled, joked, and laughed about it. We finished cleaning the dishes by hand and sat back on the couch. Kylee handed me a glass of wine, and turned on the TV.

"Are you much of a fan?" She asked, as a hockey game was just finishing up.

I nodded. "I used to go with my Dad all of the time. It was my dream to play, but I was pretty shitty," I said with a smile.

She nodded. "I've started to watch more and more since it seems like every guy I date likes this team," she rolled her eyes.

I laughed. "Sure beats the hell out of watching the Kardashians."

That caused her nearly spit out her wine and laugh.

As the postgame show started, Kylee and I had finished our wine and she cuddled up to me. She pulled my face over, and I stared into her eyes.

"Hey. How you doing?" I asked jokingly.

Her answer was a long and hot make-out session. She ended up straddling me, and dry-humping me while I held onto her hips and grabbed her ass.

She lifted up from the kiss and kissed my neck. I let out an audible sigh, as that was my weakness. My cock was already trying to pop out of my pants, so I smacked her ass hard. She let out a gasp.

"Harder," she whispered into my ear as she kissed and bit it playfully.

I smacked her other cheek harder as I heard her moan softly into my ear.

I tugged at her leggings that she wore, and she took care of her blouse. I finally had an up-close view of her tits. I didn't waste a lot of time burying my face into them. Kylee unclipped her bra to pop them free, and soon after, one of her nipples was in my mouth.

"Mmm, suck on those tits. It gets me so fucking wet. Oh God, I'm so close already," she muttered.

I quickly unbuckled my belt, unzipped my pants, and pulled out my cock. I wasn't going to get head tonight, but that was more than okay. A naked woman was on top of me saying all sorts of nasty things while my mouth was sucking her tits. Not a good time to be picky.

I slid my cock inside her pussy and she moaned out. She then pulled her own nipple into her mouth and sucked on it while she moaned. It was really fucking hot to look at from below.

She rode me while I sat on the couch and grabbed her hips. Her hips bucked and rocked against me as she increased her pace.

"Fuck yes, this dick is so fucking big inside my tight pussy. Oh fuck yesssss..."

Much like on that previous Saturday, she came in waves. Her orgasms weren't as strong, but I could tell she was enjoying herself.

However, I was getting close.

"I uh, I think I should pull out now," I muttered, urging her to slow down.

"No way," she replied. "Cum in me. Don't be scared. I'm on the pill."

Well then, that changed things.

I pumped my cock into her pussy from underneath her. "Fine then, take my fucking cum then."

That got her smiling. "Oh yes, Ryan. Blow that load inside me."

I got closer and closer as she kissed me. Then she lifted up and whispered into my ear as she moaned.

"Fucking breed me."

Those three words triggered me. I came so hard and moaned out so loud, that Kylee covered my mouth. She smiled as I pumped every ounce of cum into her.

"Fuck that felt incredible," she smiled.

She got off of my cock, and scooped any last bit of cum that oozed out of her pussy. I watched on as she put it in her mouth.

"Delicious, as always," she smiled and winked.

***

Our hookups got more and more frequent. I can't lie, the sex was the best I've ever had.

Eventually, she'd show up at my house wearing a skimpy outfit, or a trench coat with nothing underneath it. It was really hot, but it did drive me insane a little, seeing as I never knew when she was going to do that.

Kylee spent the night at my place on the weekends. It got to the point where the weather was getting nicer, the days were longer, so she wanted to go for hikes and walks around my place on the weekends. She also wanted to try everything in the sex room, but we saved that for once a weekend. She agreed, but I knew that if she could live in there, she would.

By this time, I was exclusive with Kylee. She told me she was exclusive with me, too, and I had no reason not to believe her. We decided to not put any labels on what we were doing, but it was similar to a friends with benefits situation, where we both really enjoyed spending time with each other, and we continued to have sex.

As the summer really started to get going, I had to travel a little bit for work. That meant traveling into the states for about a week or so. I told Kylee where I was going, and asked if she could watch the house. She agreed.

I arrived in my hotel in Chicago on a Monday night. I knew I'd be home on Friday, but I hated hotels. They just weren't the same as home.

Maybe a half hour after I settled into my room, there was a knock on the door.

I answered the door, and a short, bubbly, black-haired woman, who couldn't have been older than 23, greeted me. She wore a trench coat, and from what I could see, some red heels.

"Are you Ryan Sommers?" She asked.

"I am, what's this about?" I asked.

"I'm Haylee from Chicago's premier escort service. Would you mind if I came in?"

My eyes widened. 'What the fuck?' I thought, while my internal sirens were going off.

"Sure, I guess so, but I think there's been a mistake..." I said, as Haylee walked through the door.

"I don't believe so, Mr. Sommers. A woman by the name of Kylee Miller told me to come here to treat you. She told me to tell you to have fun while you're here. If you want to know what I think, Mr. Sommers, I think she's a keeper." She winked and giggled.

I hurriedly checked my phone, already seeing a text from Kylee.

"Enjoy your present ;)" was all she wrote.

'Well, I guess if she won't get upset about it...' I thought.