by Maggie Cole
I sorted through all the places I visited during my trips to Tampa. Nothing stood out. I thought about how Maddie scrolled on Instagram and booked her trip. The thought made me smile.
She was adventurous and my schedule sounded like a bore to her. Well, if I was honest, it was...
I sighed. How to show an adventurous girl she's my priority, I thought and tapped my fingers on the table.
Then it hit me. I knew what I would do.
My new partner walked in.
I looked over at him. “Can you give me a recommendation?”
* * *
Maddie
Apparently, the east wing was open again, so the resort was full of happy people. The madness of the night before was nowhere to be seen. So I spent the day doing random things. I walked the resort, then hung by the pool and talked to a few strangers who were on vacation.
Reluctantly, I wheeled my suitcase back to my side of the hotel. My gut told me Jack wanted me to stay, but I needed to think about some things.
Giving Jack a chance was one thing, but was I really contemplating a new relationship?
My brain told me that I was getting myself into a similar situation as I had been in with Mike...and I didn’t want that. Factually, I should have told Jack no and left it at that, but I couldn’t deny how his actions felt so different from the way Mike ever made me feel.
The sex was unreal...surely it was a one-off thing, and I would be disappointed the next time? Was it possible to have mind-blowing sex with the same person, for more than one passion-filled night?
The reality was, I didn’t really know Jack and I felt like the sex was blurring the lines. Almost as if, I couldn’t really see anything but good because I was under his sex spell or something.
Men like Jack Stevens don’t really exist, do they?
He will surely get bored with me after tonight.
I was lost in thought when my phone rang. It was a blocked number, so I let it go to voicemail. A few seconds later, I received a text.
“Tried calling you, but it went to voicemail. Can you call me back?”
“Who is this and what is your number?”
“Jack. Forgot my number is blocked—555-6289.”
The phone rang once. Jack picked up. “Why is your number blocked?”
“Business purposes. Put my number in and it won’t pop up blocked anymore.”
"Okay. So what’s up?”
“What are you doing tomorrow?”
My heart sank. Once again, I was going to come second, probably to his work. He was going to blow off our dinner.
Well, at least he's calling, and you're not sitting in a restaurant waiting.
"Canceling our date already, huh?" I tried not to sound disappointed, but I also couldn't deny I was a bit pissed off.
Jack roared with laughter.
“I don’t think it’s funny.” I started to get more upset.
“No. As a matter of fact, I am not cancelling our date. I am extending it.” I could sense the smug look on his face through the phone.
“Good. In that case, nothing. Remember, I don’t have any plans. I’m not scheduled like you.” I teased, as relief shot through me.
He exhaled, "Good. Can you pack an overnight bag and meet me in the lobby around five o’clock? Will you throw my stuff in there, too? There is an overnight bag in the closet.”
“Ummm...sure...can you tell me where we are going?” I didn’t tell him I was back in my room.
“Nope. I’ll text you a list of what to pack. See you at five.”
I glanced at the time—two hours till then—I better pack and go back to his place.
Sure enough, Jack sent over a list of items:
Bathing suits
Sunscreen
Casual outfit for tomorrow—shorts and t-shirt for me
My sandals, your sandals
Wear something dressy casual for tonight
My toiletries bag
Whatever toiletries you need
I texted him back. “You forgot the condoms.”
“Shit! How could I forget that? In my suitcase, inside pocket.”
“I was kidding.”
“No you weren’t,” he responded, along with winking and fist-bump emojis.
I sent him an eye-roll emoji back. Yep, he’s right, I most definitely wasn’t kidding.
I decided it would be easier to roll my suitcase back to Jack’s. So once again, I wheeled my way through the hotel. The desk clerk gave me a smirk. I ignored her.
Back at Jack’s, I put my bag together and rifled through his closet and drawers. I felt strange going through his stuff.
I texted him. “I feel like a snoop going through your stuff.”
“I asked you to, remember?”
“Still feel like a snoop.”
“Do you want me to punish you for it later tonight?”
I’ll get in line for that punishment. “Ha, ha!”
“Can you grab a pair of underwear for me too, please.”
“What if I want you panty free?”
“I can free ball it, if that turns you on.”
I sent him a GIF of a guy bowling and knocking down all the pins.
“OUCH!”
I packed everything—including a pair of his underwear, quickly showered, and started getting ready. I put on my other new sundress, heels, and jewelry. When I had finished my hair and started applying my makeup, my phone rang.
“Hello?” I answered without looking.
“Maddie, I’m running a bit behind. I’ll be there in five minutes.”
“Shoot. Jack, sorry, I lost track of time. Don’t rush, I’m about ten minutes behind.”
He chuckled. “And here I was, thinking you were going to tell me I was putting you second.”
“I’m not that unrealistic.” At least he took my demand seriously.
"I’ll see you in ten then.”
I finished getting ready and headed out. I grabbed our bag. Hmmm...that was strange...our bag. Less than twenty-four hours after meeting this guy, and I’m packing our bag to go to some random place...
I pushed the thought out of my head. Isn’t this what vacation is supposed to be all about?
6
Maddie
Jack waited for me in the lobby. A schoolboy grin grew on his face when he saw me. He wore a white button-down shirt with his sleeves rolled up and khaki shorts. Not sure how it happened, but he seemed to have gotten hotter since this morning. He greeted me with a long, lingering kiss.
After snatching the bag from me, he put his hand on my back and led me out to the car. He opened my door and I got in. After he pulled into traffic, I turned to him and smiled. “Where are you taking me?”
“You ever been to St. Pete?” He glanced over at me.
“Nope.”
“Good. Me neither.”
“Rather crazy for your scheduled self, isn’t it?”
He gave me a full dimpled smile and shrugged his shoulders.
"So what are we going to do there?”
“We’re going to have a nice dinner, then I’m going to feast on your body all night, and we’re going to spend the day at the beach tomorrow.”
My face flushed at the thought of him feasting on my body. “You aren’t going to work tomorrow?”
He raised his brow at me. “Do you want me to work tomorrow?”
“Nope.”
“Then I’m not working tomorrow.”
“Really?” I didn’t fully believe him. “Not even some laptop or phone time?”
“I didn’t bring my laptop and I’ll turn my phone off. I think I’ve earned a day off, and I can’t think of anyone else I would want to take a day off for...”
I gave him a giddy grin. “So when did you concoct this plan?”
“When I was sitting in a meeting, thinking about your blow-job skills instead of listening to important details of my newest merger.”
I slapped his arm. “Hey there! Don’t blame the blow job for yo
ur lack of professionalism.”
"Maybe it was when I was thinking about how I made your eyes roll to the back of your head…”
I slapped him again and giggled as a new shade of maroon crept up my face.
“So what did you do today?”
“Not much. Lounged by the pool. Talked to some random strangers. Walked around the resort. Nothing special.”
“Sounds relaxing.”
“It was. So what kind of company are you merging with?”
“You really want to talk about work?”
“Yes. I want to know what you do.”
Jack peered at me to see if I was serious. "Okay, but I didn’t bring it up.”
“Fair enough. Promise I won’t hold it over your head.”
“Can I trust you to keep this between us?” He shifted in his seat, tapped the steering wheel, and nervously glanced at me.
What was the big secret? My curiosity was now officially killing me. “Yes, I won’t tell anyone, I promise.”
“It’s a sex club.”
“You’re lying.”
“No, I’m not.”
I burst into laughter. “How on earth does that even happen? Do you own other sex clubs?”
“Yes, but not a lot of people know about those. Liv and Tom—they don’t know—so please don’t bring it up.”
"I won’t say anything, but why keep it a secret? I mean, if you’re going to do it, what’s the shame in it?”
“It’s not shame, I just don’t want to be seen as that guy.”
“What do you mean by ‘that guy’?”
Jack tapped the steering wheel, “You know. The perverted guy who is in the sex industry.”
“So you aren’t the perverted guy? I mean, you did some pretty perverted things with me last night.”
“That wasn’t perverted, but I can show you perverted tonight if you want,” Jack promised.
I wasn’t sure what that meant. But you can show me perverted all night long if you want.
“So you aren’t the perverted guy but you are? I’m getting confused,”
“Look, I own a portfolio of companies. A few years ago, I was introduced to a guy who needed help with his club over in Miami. I turned it around and it’s making a fortune. So every now and then, I find another gem that I’m able to turn around and make a lot of money on. But I don’t want to be known for that.”
"What do you want to be known for?”
“The guy who takes over companies and turns them around. The one who saves jobs and creates better lives for others.” His eyes were focused on the road, but I knew without seeing them that this was something important to him.
Wow. He cares about more than only making money.
“That’s noble.” I put my hand on his thigh.
We didn’t talk for a bit. Finally, I asked, “So how often do you go to these sex clubs?”
“Maddie,” he replied sternly, like it was a topic I shouldn’t breach.
“What? I want to know! Is that where you’ll be late at night?”
“Funny,” he mumbled, but he didn’t seem amused. “I don’t go when they’re open.”
“What! You don’t go?”
“No. My partners run them. I deal with the backend stuff and only go in during closed hours.”
“Well, Jack Stevens, I never would have thought it, but you’re a prude, aren’t you?”
Jack checked me out, licking his lips. “I definitely wouldn’t consider myself a prude.”
“But you won’t go to a sex club, even though you own them?”
He glanced over at me. “Would you?”
I shrugged my shoulders. “With you? Sure, why not?”
Jack laughed. “You’re serious?”
“Yeah, why not? Could be fun! I mean, I’ve never been to one but it could be interesting. Think of it as taking me to work.”
Jack glanced at me in disbelief. “I can’t even believe we are talking about this right now.”
“Why? Because you’re a prude?”
“No, because you are serious about me taking you to a sex club.”
“I think it could be kinda hot.”
“You’re serious?”
“Yep.”
He shook his head as we pulled into the hotel. The valet came to take our keys, and Jack snatched the overnight bag from the backseat, walked around the car, grabbed my waist, and led me inside. He quickly checked us in.
When we arrived at the room, Jack dropped the bag. He pulled me out onto the balcony that overlooked the beach, “Wow. That’s a beautiful beach. Thanks for planning this.”
Jack pulled me to him, kissed me, and grabbed my ass with both palms. He wadded my dress up, and took a finger and moved my underwear aside, then slid it into my pussy. It caught me off guard and I inhaled sharply.
“You’re so wet. All that talk about the sex club has you worked up?” He raised his eyebrows at me.
I tried to catch my breath as his finger moved against my walls, and caused me to stand on my tip toes before I sank back on his hand.
“We have reservations, so this is going to be quick, but I’m going to make you cum, and then I’m going to lick my fingers, so I taste you all night long. Is this a good start for perv?”
Apparently, he was on a mission to show me he was a perv. I stared at him, and I tried not to smile but didn’t accomplish that goal very well.
Jack didn’t wait for me to answer and began to work me into a high. He went right to my G-spot, and my lip started shaking. I lost the ability to stand. He grabbed me, turned me around, and held me tight around the waist, before he pushed me up against the balcony so I faced everyone on the beach below.
We were on the twentieth floor, so no one could probably see my face contort or hear my muffled cries, but the fact that someone might watch and hear stirred something in me.
As if he could read my mind... “Do you like the thought of someone seeing you? Hearing you?” Jack whispered into my ear, while he tapped my G-spot and made me inhale sharply.
He tapped, tapped, tapped, and I thought I would explode. Totally different than the night before or this morning. How this man knew how to do all these different things to my body was a mystery to me.
“Oh, God,” I breathed out.
His teeth pulled my sundress string, and my dress fell. The arm that was around my waist inched up but stayed secure, while his hand reached up and slid under my bra, then rubbed my nipples. Jack’s tongue flickered on my neck.
Whimpering against him, I was putty in his hands, as I melted into his every touch.
"Do you stay this quiet, or let everyone know you're being pleasured?" he whispered, tapped me hard, and sent the first set of small tremors throughout my body.
My voice became a reflex, and I cried out his name as I lost any remaining ability to stand. A ragdoll, held only by his arm, and the wall as the heat from his body coursed through my backside, and his cock pulsed against my ass.
I had little room to move, but I pushed my backside as hard as I could against his cock and ground into his hand. Dizzy from the heat in the air and Jack's warm body next to mine, I closed my eyes, heard the waves crashing below me, and seagulls calling out.
Jack's lips murmured in my ear, "So many things I want to do with you."
“Jack…I...” I latched my arms behind Jack’s neck as my body repeatedly clenched his fingers, unable to stop. My lungs vibrated, and my head leaned back, further into Jack’s neck, while my eyes flickered, and my breath puffed out of my mouth.
It’s so hot. Please make me fly.
“I’m going to make you cum now, and then I’m going to taste and smell your deliciousness all night.” Jack tapped me some more and swiped my clit with his thumb.
I peaked almost instantly, cried out his name, and didn’t care who heard me or saw me. My body burst in his arms, and I shuddered savagely against Jack and the wall. Over and over, my high rippled through me.
When I was done, he turned me around
so I could watch him suck on his fingers, before he pushed them into my mouth.
“You are a perv,” I whispered to him, a massive grin on my face.
Jack gave me a cocky eyebrow and tied up my sundress. “Let’s go.”
7
Maddie
The elevator doors opened to a rooftop bar. Live music pulsed through the air, and a view of the sunset drew a crowd with standing room only. Jack had reserved us a VIP area and we were led to a cabana room with a table and couch. We sat on the couch, Jack’s arm around me, as I leaned into his chest.
The waitress came over and we ordered drinks.
“How did you know where to go if you haven’t been here before?”
“I asked Roy.”
“The sex club owner?”
“Yes.”
“So I really do think we should go check this out one night while we are here,” I told Jack. I had never thought about going to a sex club before, but to my surprise, I was curious, and I figured it would be fun with him.
“Maddie, I’m not taking you to a sleazy sex club. If any other dude tried to touch you, I’d beat his ass.”
I laughed. “Easy there, killer.”
“I’m not laughing, Maddie.”
"What if a girl wanted to touch me?”
Jack’s eyes widened. “Are you into that?”
Ignoring the question, I asked, “Would you beat her ass?”
“Very funny.”
“I don’t see the difference.”
Jack shifted in his seat. “You know, you’re right. There isn’t a difference in some ways. I wouldn’t want to share you with anyone.”
“You’re not telling me, if I wanted to have a threesome with another girl, you would say no?”
“I would one-hundred percent tell you no,” Jack firmly declared.
“You must be the only guy on the planet who would say that.”
“Have you had a threesome before or been with a girl?”
“No. But you’re really surprising me here. I really didn’t expect your prudish ways,” I teased him.
Jack’s face was serious. “I will never share you with anyone.”