I’m a perfectionist. It’s not really a surprise to anyone who knows me well. Even when I was in Nsync, there was plenty of stuff printed about me being the “Daddy” of the group or that I had perfectionist tendencies. I guess I just like things done a certain way.

When I met Jenna two years ago, she was the complete opposite of any woman I’d ever dated. She was clumsy, loud, and the closest thing she’d ever come to seeing a designer brand was shopping at The Gap. We met at my brother’s wedding. Ironically, I was dating somebody else at the time and didn’t really give her a second glance until the reception when she let loose to “Single Ladies.” She could move, that was for sure, and unlike Kathryn, my then-girlfriend, she wasn’t afraid to have fun with it. When Tyler’s bride introduced her to me, she actually blushed. Normally, that’d turn me off. I would have assumed she was a former fan of Nsync and that she would’ve started gushing to me about how many concerts she’d gone to or how much she loved us back in the day. But like I said, there was something about her.

“Shit, I’m so sorry. I’m Jenna. And I’m not going to lie. I used to have a poster of you on my wall in college,” she admitted freely.

“Hey, we all have a past.” I’d teased her and immediately wanted to know more about her. Turns out she lived fifteen minutes from my West Hollywood home and knew Tyler through mutual friends in Orlando. It’s a small world after all.

I won’t go into too much detail but about three months later, I’d broken it off with Kathryn and hadn’t stopped thinking about Jenna. I got her number through Tyler and called her. Our first date was two days later and we’ve been together ever since. She’s easy to please, she’s not over the top about anything except her new fetish for designer make-up (that’s about the only designer thing now she likes), and she’s probably the most down to earth girl I’ve dated.

So, about my perfectionism.

I wanted our Valentine’s Day to be special and since one of my favorite hotels is the Fontainebleau in Miami, I decided we’d spend the weekend there. I only told her to pack a bathing suit, a few dresses for going out, and pajamas, but only if she thought she’d actually wear them. The day before we left, she spent an hour trying to get it out of me where we were going. Jenna loves surprises but she also is insistent at the same time.

“Hawaii?” she asked me, when I pulled out a pair of blue swimming trunks.

“Jen, I’m not telling you.” I turned around and grinned at her. “But keep guessing. This is fun.”

Jenna sighed and leaned back on the bed. “Cozumel? Oh, wait are we going on a cruise? Because I misplaced my passport a few months ago and –“

“Jenna, if we were leaving the country I would’ve told you.” I assured her.

“Philly?”

I turned to her and gave her a weird look. “Philly?!”

Jenna giggled and pulled her knees to her chest. “It was a random guess.”

“No. Not Philly.” I turned back to packing. “Do you really want to know?”

“No,” Jenna answered quickly. “Well, yes, sort of.”

“All I’m going to tell you is that we’re going to Miami.”

Jenna raised her eyebrow. “Miami? Really?” I saw her face fall but she tried to compose herself. “Oh. Well, that should be fun.”

“Jenna, Miami’s great. It’s like L.A. but smaller and trust me, we’re going to a five star resort hotel on the beach. You’ll feel like you’re in another country.” I sat down next to her on the bed.

“That’s because we will be in another country. Do you know how close it is to Cuba?” She was teasing me but saw my face and relented. “Sorry, babe. I’m really excited! I promise! I just didn’t expect Miami of all places when you mentioned a Valentine’s Weekend.”

“You’ll love it.” I leaned over to kiss her and she kissed me back.

Packing ceased for about the next fifteen minutes.

 

When I picked Jenna up the next day, I knew to arrive fifteen minutes before I said I’d be there. That’s because Jenna can’t be on time to save her life. I heard her running to the door of her apartment and she threw it open, out of breath as though she’d just run a marathon.

“Hey!” She tried to catch her breath. “Sorry. I woke up late and then I couldn’t find my new bathing suit.” I walked into her apartment, which looked as though her closet had thrown up all over her living room floor.

“Honey, what…I mean, do you have any clothes in your suitcase?” I walked over to the coffee table upon seeing three bras strewn across it and picked one up. “Why didn’t you pack this one?” It was a red, lacy strapless bra that I loved seeing her in whenever she took her clothes off.

“Because it goes with nothing that I’m wearing!” She called back from her bedroom.

“Well, that doesn’t matter. You can still wear it,” I muttered and wandered into the other room where Jenna was hastily throwing the last of her things in her suitcase. I tossed it on top and she was too busy opening and closing drawers to pay attention to it.

“Okay.” She took a breath. “Bathing suit, three dresses, lingerie-“

“Ooh, which ones did you bring?” I went to take a peek in the suitcase and she somehow managed to jump over to me, slap my hand and shut the suitcase quickly.

“You’ll find out tonight!” She moved away from me and when she wasn’t looking, I lifted the top of the suitcase and peered inside. I saw the black teddy I’d gotten her as part of her Christmas present and a Victoria’s Secret bag underneath that. So, she’d gone shopping? That was good news to me.

“Are you almost ready, babe?” I ventured to ask, as she scurried out of her bathroom with her make-up bag, toothbrush, and hairbrush. She threw everything inside of her suitcase and looked hastily around the room.

“Yeah, I think this is it.” She nodded.

“Um, sweetie….” I looked at her still dressed in her pajama boxers and camisole. “I mean, if you wanna go to the airport like that, it’s fine, but-“

“Oh, shit!” Jenna groaned and immediately threw her camisole over her head, revealing nothing underneath. It took everything in me not to grab her and throw her down on her bed but I knew we’d get plenty of that tonight when we landed. Not to mention, she’d definitely turn me down because she was in such a hurry.

I watched her quickly fasten her bra, throw on a white t-shirt, tie a pink scarf around her neck, zip up her jeans, and slide her feet into a pair of black flats. She ran a finger through her hair and walked back to her suitcase, zipping it up and taking it off the bed.

“Okay. I’m ready,” she told me and began to walk out of her bedroom. Her apartment was a mess of clothes but I figured she’d be coming back to my house anyway when we came back so it didn’t matter.

“Great, let’s get to the airport,” I waited while she locked the door and bolted it, then linked my fingers through hers and headed to the car.

 

I should have known that this little getaway wasn’t going to go exactly as planned because for a perfectionist, nothing ever goes as planned. But so far, everything was more or less perfect. We were flying First Class and Jenna was getting tipsy on champagne, which made her aroused and when the plane took off, she grabbed her blanket and threw it over us, rested her head on my arm, and let her fingers rest between my thighs. I glanced at her and she grinned wickedly at me and continued to tap and strum right on my dick.

“Jenna,” I whispered. “Are you gonna do this all five and a half hours of this flight?”

She chuckled and reached up to kiss my lips then moved her hand away.

“No, but I wanted to give you a preview of what I’m gonna do to you tonight.” That’s the thing with Jenna. She can be a tease when she wants to be. She’s gone down on me plenty of times in the back of a limo on the way to an event in Hollywood. And once at a birthday party she pulled me into Lance’s bathroom for a quickie. So I wasn’t going to put it past her to get me off on an airplane but I guess even she had her limits of what was too far. She’s a good girl on the outside, but a freak on the inside and I love her for it.

“I can’t wait.” I kissed her temple and she nestled against me and closed her eyes.

 

By the time we landed in Miami, it was almost 9:00 that night. My plan was to check into the hotel, change, and have a late dinner at a restaurant on South Beach. We retrieved our luggage and a limo was waiting for us when we stepped outside.

“Happy Valentine’s Day, baby.” I kissed Jenna and she vigorously kissed me back until she was straddling my lap. The drive to the airport isn’t that long but it was long enough for her to get me thinking about canceling dinner and ordering room service instead. When the limo pulled up to the front of the hotel, Jenna quickly smoothed out her hair and then looked down at my erection, which was not well hidden at all.

“Baby…” She bit her lower lip.

“It’ll be fine. Just, let’s go inside.” I slowly got out of the car and followed her into the hotel lobby after collecting our bags. A bellhop followed us to the Concierge check-in and Jenna slid her hand through my arm resting on the desk.

“Hi, Josh Chasez checking in for three nights.” I handed the front desk agent my AMEX and she smiled at us.

“Welcome back, Mr. Chasez,” she said. “Happy Valentine’s Weekend.”

“Thanks,” I replied and looked at Jenna, kissing her forehead. I couldn’t wait for her to see our room. I’d made sure to call ahead and have it decorated with rose petals all over the bed, champagne in a bucket, and chocolate covered strawberries. I know, I’m a huge romantic at that.

I looked back at the front desk agent who was grimacing at her computer. She cleared her throat and forced a smile, then walked away and began to converse quietly with another agent.

“Is something wrong?” Jenna asked me and I shrugged, waiting for her to return.

“Um, Mr. Chasez? You booked for tomorrow night until Sunday night.” She looked at me apologetically. “The fourteenth to the sixteenth.”

“What?!” I was trying my best not to freak out. “Are you kidding me?”

“I’m sorry, sir, but you booked an ocean front suite from February 14 until February 16. Today’s the 13th,” she told me as nicely as she could.

“Do you have another room?” I ventured to ask and I didn’t even finish before I saw her shaking her head.

“I’m afraid not. Not this close to Valentine’s Day.” She began to click on her mouse and then folded her arms across her chest, then looked at me. “I’m trying to see if we can put you in one of our condo’s for the evening.”

“I don’t believe this,” I groaned and rubbed my forehead with my hand.

“It’s okay, baby. We’ll find somewhere else and just come back here tomorrow night.” Jenna was trying to assure me as she always does when things go awry. Leave it to Jenna to see the glass as half full right now.

“We have a condo that’s partially being remodeled. You can still stay in it, but the living area is closed off. That’s all I can offer you,” the agent said and looked at us with a regretful expression. “I’m really sorry, Mr. Chasez.”

“No, obviously, it’s my fault. I don’t know what I was thinking,” I sighed and shook my head. “Yeah, okay, fine, we’ll take it.”

“Perfect.” The desk agent nodded and began to type onto her computer. “And you’ll have your ocean front room tomorrow by noon.” She handed me the key. “The condo is just outside to the right of the hotel in the large white building. Your room is on the fourth floor and faces west.” So in other words, away from the ocean. “Room service does deliver and we have our signature restaurants that are open tonight until three a.m.”

“Thank you so much.” Jenna smiled at her. “We really appreciate it.” She hit my arm and looked at me pointedly. “Tell her we appreciate it!” Jenna said through gritted teeth.

“We appreciate it,” I mumbled and followed the bellhop outside and over to the condo building.

As soon as we entered our room, we were met with hot air circulating throughout.

“Oh dear, I guess they didn’t turn on the air conditioning in here,” the bellhop said and went over to the unit on the wall. He hit it a few times and then looked at us. “I’ll get maintenance up here right away.”

“Why?” I asked, walking over to the air condition pad.

“It looks like your air condition isn’t working.”

I held in a groan and pursed my lips together tightly.

“Don’t worry, it should be fixed in no time,” the bellhop assured us. I took my wallet out of my back pocket and handed him a $20 before he left. I turned around and let a breath out between my teeth.

“Josh…” Jenna walked over to me, draping her arms around my neck. “It’ll be fine. Don’t freak out.”

“I’m not freaking out.” I moved away from her and sat down on the bed. “It’s just not what I planned and I wanted us to have a perfect weekend.”

Jenna sat down next to me on the bed and put her hand on my thigh, giving it a gentle squeeze. “We’re here. Together. There aren’t any distractions. Just you and me. What’s so not perfect about that?”

“I had a whole suite for us-“

“We have it tomorrow at noon.” Jenna reached over and kissed my cheek. “So technically, we just have to sleep here one night and we’re in the Fontainebleu condominiums, Josh. It’s not like they put us up at a Motel 6!”

Sometimes I forget how spoiled I’ve been in the last twenty years. Jenna always seems to remind me of that. She was right. We weren’t in a crappy motel. We were in a luxury condominium. Granted, it had no air conditioning but maybe after dinner we’d come back to a cooler room.

“I know,” I sighed and stood up. “C’mon. Let’s go get something to eat.”

We quickly changed and Jenna wore a hot little red halter-top with a short black skirt. Before we left, she turned to me, and whispered in my ear, “I’m going commando tonight, just so you know.” And then walked out of the room, leaving me standing there watching her leave.

“Jenna.” I couldn’t help but partially whimper as I followed after her to the elevators. “Why do you do that to me?”

“What?” Jenna looked at me and feigned innocence.

“You know what.” I grabbed her around the waist and kissed her fiercely on the mouth. “They have room service you know.”

“I know they do. But our air conditioner is being fixed not to mention I want to see what you find so amazing about Miami.” Jenna ambled onto the elevator and I followed, linking my fingers through hers.

When we stepped out of the condo, we were right on Collins Avenue, close to a lot of upscale restaurants. The night air was warm and balmy for a February in Florida.

“Cab?” A valet asked, while we stood outside the condominium.

“Yeah, thanks.” I nodded and pulled Jenna close to me. I rested my hand on her butt and she giggled and shook her head at me.

“Copping a feel already, baby?” She glanced at me and I looked down and smirked at her.

“Just testing to see if you were telling the truth,” I gave her butt a little smack. “Yep. You were.”

“Oh my god,” Jenna giggled and rolled her eyes. “Down boy. You’re gonna get plenty of action when we get back.”

“Yeah? Is that a promise?” I pulled her against me, my lips on her temple.

“Mmhm.” Jenna nestled into me and I pecked her cheek and then her neck while we waited for the cab.

Pretty soon I’d forgotten why I was so frustrated in the first place. We ate at a hip Cuban restaurant right on South Beach and then hit a few clubs nearby. By the time we got back to the condo, we were both pretty tipsy and all over each other. Jenna was groping me in the elevator and as soon as we got off on our floor, I was fighting taking her right there because I was so ready. I pushed her against the door and tried my best to swipe the key in the slot and after a third time, I finally heard it click. I shoved the door open, still holding onto Jenna, still kissing her, and it wasn’t until we were hit with a wave of heat that I remembered why it was I’d been so irritated before.

“Are you fucking me?” I griped, seeing a note from maintenance on the air conditioning pad. It stated that they were very sorry but the air conditioner was broke and they hoped it hadn’t caused any inconvenience.

“Well, not yet, baby,” Jenna cooed, trying to pull me back to her. “Josh, c’mon, let’s go!” She walked past me and fell back on the bed, spreading her legs ever so slightly.

I threw the note to the side and wiped the sweat from my forehead. Just looking at her made me forget that we were in an overheated room and that nothing had gone as planned since we’d landed. Jenna sat up on her knees and crawled over to me, gripping the hem of my shirt and pushing it up until I grabbed it and tossed it to the side. Her lips met my chest and soon she was sucking and licking around my stomach and then looked up at me when she gripped my belt buckle. Beads of sweat had started to form on her forehead and she wiped it off with the back of her hand before she continued to remove my clothes.

I stood there in nothing but my boxer briefs, ready for her to continue. She looked up at me and grinned, then rubbed her hand over my erection, which made me groan with satisfaction. Her fingers played with the hem of the boxer briefs and she slowly moved them down over my swollen member until they were in a puddle around my ankles.

“Lie down,” she whispered.

I eased myself back onto the bed and Jenna crawled on top of me, assaulting my chest once more with her tongue. She let out little moans as she made her way down my body and soon her tongue was tracing over my dick. I couldn’t help but thrust up into her mouth and she stopped and looked up at me for a minute.

“Um, easy, there. Unless you want me to bite it!” Jenna warned me.

“Sorry.” I felt sweat starting to form once more on my forehead but was too into what she was doing to me to wipe it away.

 I looked down at her going at it hard and fast and then slow and easy, teasing me occasionally by taking her mouth away and letting her fingers work their magic. She was good at this part. She knew how to please her man and I’d never once complained or had to tell her just how to do it. She went back to sucking and licking me and I pulled her hair letting her know I was about to let go. Jenna only went harder and when I came, she looked at me and wiped her mouth. I was still twitching and shaking as she crawled back next to me and pulled me on top of her.

“It’s hot, baby.” She breathed in my ear and sat up to take off her halter, which revealed nothing underneath.

“You didn’t have a bra on, either?” I nearly choked and turned to my side. Jenna lay down next to me again and I rolled onto my side, resting my hand on her breast.

“I thought you knew that,” Jenna replied softly, closing her eyes as I began to massage her. “Mmm.” She let out a moan and I continued to squeeze and touch her.

I rolled on top of her and nipped at her neck, her breasts, and her stomach. My favorite part about this woman is her stomach and I always pay extra attention to it. Blowing, sucking, kissing, anything that gets her to the point where I can finally get down to where I know she wants me. That night was no different. Just knowing that there was nothing between the fabric of her little black skirt and me made me even want it more. I pulled it down past her thigh, past her knees, and Jenna kicked it off of her foot. She propped her legs up with her feet and I smiled at her before I started to go down on her. I let out a hot breath right at her center just to tease her and it worked because she bucked beneath me and let out a whimper.

“Jo-osh!” She groaned. “Please, baby.”

“Relax,” I whispered and kissed her thigh.

I moved between her legs and let my tongue slide up to her clit. She was moaning and it only got louder when I pushed three fingers inside of her and continued licking her. I loved doing this to her because watching her face when she comes is one of my favorite things in the world. She tries her best to always hold in her orgasm because she wants it to last, but then she gives up and like that night, couldn’t handle it much longer.

“Josh. Shit. Fuck!” She nearly screamed my name and I continued to lick and felt her contract around my fingers. I pulled them out and looked at her while I licked them off and she smiled at me. We were both sweating from the heat in the room and the heat we’d just caused by getting each other off.

And it wasn’t over.

I crawled back up to her and kissed her hard on her mouth. Jenna’s legs intertwined with mine and she giggled into my mouth when she felt my erection brush against her thigh.

“Good. You’re up again,” she whispered and kissed me again.

“You make it easy,” I told her and pushed myself up onto my hands. “You were really wet just now.”

“When you do what you just did I can’t help it.” She pulled me closer to her. “Josh, I want you inside of me.”

“Yeah?”

“Mmhm.” She spread her legs further apart and made it easy for me to slide inside of her. Even after two years, being with Jenna always felt amazing.

I rocked slowly and deliberately and Jenna met up with me at every thrust. Pretty soon the room was filled with sex and heat and gasping and moaning and I didn’t care that we were in this unbearably hot room. Jenna’s whole body was soaked with sweat as was mine and soon we were sliding against each other because of it. I never lost momentum and neither did she. Her legs wrapped around my waist, her back arched, her arm around my neck and me with my arms on either side of her giving her everything I could. It was perfect. Nothing, not even the heat, could distract us right then.

“Play with my breasts,” Jenna whispered, her head thrown back on the pillow. I moved one hand away from her head and began to knead her breast, then bent down to tug at her nipple with my teeth. She groaned like I’ve never heard her groan before and it only made me continue.

“You like it when I do that?” I looked right into her eyes and she could only bite down on her lower lip because her orgasm hit and she threw her head back onto the pillow.

“Josh…” She moaned and I continued my assail on her breast. And then I felt mine course through me. It was powerful and long and Jenna held onto me before I fell on top of her. My forehead stuck to her shoulder because of how much we were sweating. Both of us were out of breath and when I lifted my head up, I saw that her brown mane was soaked. She shuddered beneath me and I tried to catch my breath once more.

“I’m sorry I was a punk earlier,” I whispered, rolling off of her. We were both so physically hot that I knew she’d be fine if I didn’t hold her like I normally did after we made love.

“It’s okay.” She looked over at me and wiped off a bead of sweat that was on the edge of my nose. “I think it turned out perfect.”

I chuckled at her. “Uh huh. It sure did.” I sat up and looked at the mess of covers soaked in our sex and sweat. “I always feel bad for the maid after we do it in a hotel,” I told her. “And the poor maid in this room will have to deal with after sex sheets and a room with no air conditioner.”

Jenna eased herself off the bed, wrapped herself in a sheet, and walked over to the sliding glass door that overlooked Collins Avenue. She pulled the door open slightly so that a light breeze filled the room.

“Why didn’t we do that before?” I shook my head as she came back to bed.

“Josh, seriously? Did you want all of Miami to hear us a few minutes ago?” Jenna rolled onto her stomach and faced me.

“Maybe.” I raised an eyebrow and Jenna threw a pillow at me.

“You’re sick,” she sighed and rested her head on her arm, still looking at me. “So, Mr. Perfectionist. You still think this vacation is ruined?”

I shook my head and she moved closer to me. “No. I think it turned out just like it was supposed to.” I reached over and traced my thumb on the side of her cheek. “I love you, Jen.”

Jenna closed her eyes and smiled, moving so that my arm was now draped around her body. “I love you, too, Josh.”

“Happy Valentine’s weekend,” I reached down to kiss her goodnight and she gave a contented sigh. “Thanks baby,” she mumbled, already falling asleep. “Happy Valentine’s Weekend.”

 

So, the rest of the weekend was actually a success. We got our suite, our chocolate covered strawberries, our champagne, our ocean front room, and our air conditioning. The hotel paid for our second night because of the state of our room the first night. Jenna ended up loving Miami and on our last day, suggested we come back for another weekend. I told her I’d think about it but I already booked us a weekend in May, right after our cruise. Don’t worry, I’m planning on telling her that we’re leaving the country.

 

The girl’s got to find her passport, you know.