tagCelebrities & Fan FictionOne Night with Jessica Simpson

One Night with Jessica Simpson


I was tired. It was late, near midnight. It had been a long day of meetings and conference calls and more meetings. Dinner was even more business. Business travel was never fun and all it ever did was leave me worn out and often the only reward was a cold and a list of "honey-do's" once I came back home. I sighed and leaned my head against the cold marble wall between the two elevator banks of my hotel, sighing, waiting for the elevator to ding it's arrival. At least it was a nice hotel, the company sparing just a little expense to make sure it's executives had appropriate accommodations during trips. I closed my eyes and almost let my mind wander.

Then I heard a loud shout, something like the word asshole, then a crash and a clattering across the floor. I turned my head slightly to the right, towards the deserted lobby of the hotel and watched a small silver cell phone skitter across the floor to end up against my foot. I pulled my head from the wall and glanced around. Where the hell had it come from? I bent down and retrieved the phone and jiggled it in my hand. It started to ring, making me jump about three feet. The elevator dinged it's arrival. I glanced back at the open doors then back towards the lobby, the phone ringing in my hand. "Hello?" I called out, taking a step towards the lobby, then back to the elevator, then back at the lobby. I contemplated dropping the phone into the bush near the elevator bank and heading for my room. Whoever owned had thrown it so they must not care about the call right? But my conscience got the better of me. I adjusted my attaché case and suit jacket in my other hand and walked to the lobby, my elevator car closing it's doors and leaving me.

I went into the lobby and heard a small sniffle. I looked around and thought I saw someone in the far corner, their back to me. Then I realized it was a woman. The phone kept ringing in my hand. Christ, did this thing have voice mail? I walked closer to the slumped figure. "Excuse me? Miss? I have your cell phone and it's ringing. Would you.."

"Want it back?" She snapped, her back still to me. "Hell no. I know who's calling and he can go to hell for all I care the cheating, lying bastard!"

Great. What had I got myself in the middle of. Should have left the damn phone and went to my room. I stared at the small silver phone, ringing in my hand and thought about answering it. A small voice said drop it and run, while another voice was both curious and concerned. Maybe I could help right?

I flipped the phone open. "Hello?"

"Jessica! Huh? Wait, you're not Jessica. Who the hell are you? Put my wife on the phone asshole." It was a mans voice. A very angry mans voice.

"Uhmm, she's not here at the moment. I found this phone on the floor and it started ringing. I thought maybe the owner had lost it and was calling the number to see if someone answered. I figured I would be able to return it." My reply was smooth and even toned. Hell maybe this guy would calm down and I could give his wife the phone back.

At my speaking the woman on the chair turned and listened to me speak. I took only a casual glance at her and then went back to my phone conversation, listening to the reply. "Where'd you find the phone?" His voice still had an edge to it but it was lessening.

"Uhmmm in the lobby of my hotel, the Saint Francis in San Francisco." I glanced back up a the woman and she was turned slightly. Her long blond hair was pulled back into a pony-tail and the corner of her left eye had a small smear of mascara. Obviously she had been crying.

"Listen pal, thanks for being a good Samaritan. My wife just happens to be staying in that same hotel. Why don't you do us a huge favor and just drop the phone at the front desk. I'll call them later and make sure she gets it. Okay?"

I rolled my eyes knowing fully well what else he was probably going to make sure she got for chucking her phone away mid argument with him but hey who was I but a weary business man, thousands of miles from home. "Sure, sure. I'll drop it at the.." At that moment the woman turned to me and shook her head in an emphatic no. It was the first time I really noticed her. Damn she was beautiful behind the puffy mascara stained eyes. She looked familiar too but I couldn't put my finger on it "...front desk." At the same time I acknowledged her by nodding. "I'm hanging up now," I said into the phone and then closed it up, ending the conversation.

I walked the few steps towards her and extended the phone for her to take. "Listen I'm sorry I got involved. It wasn't my place too..."

"No it's alright. I never should have thrown the phone it's just that..." She sobbed then and sniffled and fought back tears, turning her face into a mask of anger. "That son of a bitch is such a liar. He's cheating on me I know it. My friends told me so. He's in L.A. fucking that slut! How could he!"

I swallowed hard. I had no intention of getting involved in a lovers quarrel at one o'clock in the morning in some hotel lobby. I had a mid morning flight to catch. I still held the phone out.

She took a deep breath, the intake of air broken by a couple of small sobs. She took the phone. "I hope everything works out for you. I'm sorry about your situation." I said in a reassuring tone.

She sniffled again and looked up at me and for the first time I saw all of her face. It then hit me like a ton of bricks. The woman I was talking to was none other than pop sensation Jessica Simpson. I knew that from the posters hanging on my kids' walls, and CD's and MTV. Holy shit! I thought to myself again, I got involved in something that was too unbelievable to be real.

She smiled. "No, thank you for being a sweetheart. Most people would have just bailed on something like that." She took the phone from my hand, our skin brushing slightly together. I didn't react overtly. I have always been the kind of person that did not hold celebrities in awe. They were people just like you and me. It just so happened that their job was to sing in front of thousands or make a movie.

"It was nothing," I said and smiled back at her. "I hope you have a better rest of your night and things work out." I turned to leave and a hand grabbed the sleeve of my shirt.

"Don't go. Would you mind just sitting and talking?" She lowered her eyes then looked back up at me. "I'm all alone here and, well, I could use someone to talk to. You seem nice and, well, could you?" She batted her eyes in a move that probably had hundreds fall for her whims. Hell she was gorgeous and that move would have worked famous or not.

"Sure. You want to sit here or maybe get a cup of coffee...?" I let the question hang out there. Here I was, a nearly forty year old man asking out some twenty something starlet for a cup of coffee. What was I thinking?

"To be honest, I really don't want to go out of the hotel." She glanced out towards the main doors off the lobby and the street that lay beyond. I got her drift. There were paparazzi everywhere in her world. It was fortunate one hadn't jumped out of the fireplace in the corner yet but it was pretty late on a weeknight and the staff at this particular hotel was pretty good. Jesus, now I was worried about paparazzi. What the hell is going on. Someone pinch me. "How about my suite? We could call in room service?" She said innocently.

Did I just hear her right? This beautiful woman just invited me to her room? Now I may be pushing forty but I'm no ugly duckling. Eating right, almost daily workouts and playing recreational sports had kept me fairly fit and trim. Daily battles at the office and the boardroom kept my mind sharp. "Sure. Why not." I replied with a smile. I offered my hand and helped her from the couch.

Her heels clicked along on the marble floor to the elevator bank. She pushed the up button and this time there was no wait. An elevator opened for us. We went in and she pushed one of the topmost buttons on the panel. The suite floor in the Tower. I had a feeling this would be the awkward moment, the silence as the elevator lifted us towards her floor. Strangely it wasn't.

"Here on business?" She asked, pointing to my attaché case that held all my meeting materials and laptop.

I raised it up and glanced at it as if I needed to stare at it to confirm her question. It also pulled my eyes from her beauty. "Yep. Had a busy day. A tiring day."

"What is it you do?" she asked innocently.

"I'm a supply chain analyst slash logistics director."

She nodded knowingly. "Sounds interesting."

"It can be," I replied. "I'm responsible for the product flow through seven regional DC's out to over one hundred retail stores." I sighed. "It can be demanding but rewarding."

"So you must have to travel a lot right? To visit all those distribution centers?"

I nodded in agreement. She seemed knowledgeable, at least a little bit anyway and far from her ditzy TV personality. The elevator stopped and opened. We walked down the hallway and reached the Shangri-La suite. She opened the door and I followed her in.

Suite my ass. More like an apartment. I shook my head slightly as she walked to the various rooms, inspecting each one, talking to me as she went. "Just make your self comfortable..." She stopped mid sentence and stared at me, starting to laugh. "I just realized I don't even know your name. You must think I'm some crazy chick just inviting a total stranger up to my suite."

I laughed a bit too. "The thought did cross my mind. I'm Dan by the way." I dropped my case and suit jacket onto one of the chairs in the living room and walked towards her, hand extended.

She reached out her hand and we touched, shaking hands slowly. "I'm Jessica. Nice to meet you Dan." Her smile nearly knocked me over. I reluctantly took my hand back.

"So how about that cup of coffee?" She asked.

"Sure," I replied.

She went to the phone and pushed the button for room service, talking to me around the mouthpiece. "Make yourself comfortable Dan." Then she ordered a couple of decaf latte's. I plopped onto one end of the big sofa, sinking into the pillows. Crap I could fall asleep. I did.

"Dan? You in there?" I felt a hand softly shaking me. I opened my eyes and knew I had gone to heaven. Jessica was leaning in front of me tapping my arm and holding out a cup of coffee. She smiled that smile. "You fell asleep silly. Here's your coffee." I took the cup and sat up a bit on the sofa. She went to the opposite end and plopped down sideways, crossing her legs and facing me, her back to the armrest. I noticed she had changed. Gone were the skin tight designer jeans, beautiful blouse and Manolo Blahnik shoes. In their place was a loose fitting sweatshirt with sleeves so long her well manicured hands were inside them, and a pair of loose fitting sweats. Her feet were bare. Her face was scrubbed and looking radiant without any makeup, her hair still pulled neatly back in a pony-tail. Comparatively I must have looked like hell in my wrinkled dress shirt, top button undone as I had shed the tie hours ago, and my no doubt wrinkled slacks. She sipped her coffee and stared at me over the rim of the cup.

I adjusted my position a bit and attempted to at least sit up straight. I took a sip of my own coffee and felt its warm sweetness run down my throat. That tasted good. I also turned a bit sideways, one leg onto the couch, facing her. She was just two feet away. "I'm again sorry to have overheard your conversation earlier. That kind of thing really must suck. I didn't mean to seem like I was prying or anything."

"No, like I said before, its okay." Tears almost started to well up in her eyes as her lip quivered. "It just hurts you know. We had been fighting lately and both of us traveling and me being gone but I never thought..." Her voice trailed off.

I instinctively reached out and gently tapped her knee, "It's alright. It's going to hurt at first but I'm sure things will..."

Her gaze turned angry. "No they wont. It's going to be over. He wants it that way then he can have all the ass he wants including that slut. I knew she was trouble from the start. She practically begged to have him on her show."

That was the first time she had mentioned anything to do with her celebrity. She had not once intimated that I should know her, know what she was talking about, or give her some special treatment. It was those facts that endeared me to her even more. She took another sip of coffee and the flood started.

She went into how they had been fighting, arguing over starting a family, dealing with the constant pressure of fame, how she just wanted to be normal at times. They began to grow a bit distant, spending less time together, her career pulling her one way, his another. Then he had the opportunity to act, to be on a show that had been highly rated and still had a cult following. Not to mention three rather beautiful leading ladies, including one, that Alyssa bitch (her word not mine).

She went on like this for minutes, letting all drain out of her, seeming glad to have someone with a real life perspective hear it all. I sat and nodded, smiled, glared and reacted to each bit, talking her through things, occasionally patting her leg reassuringly, all the while unknowingly getting closer to her on the couch. My coffee, what was left of it was cold. It was nearly three a.m. She had petered out and rested her head to the side. I think she had fallen asleep. She looked so angelic.

I rose from the couch and went over to her. I scooped her up easily from the couch and carried her to the bedroom, laying her gently onto the bed. My face was fairly close to hers as I tried to be quiet and pull a blanket over her. Her eyes came slowly open. She smiled a sleepy smile and leaned forward kissing me right on the lips.

It seemed to be an innocent kiss, a simple good night and thank you for being what she needed right then, a friend. But her lips lingered. I cocked my head to the side and our eyes met. Both of us moved at the same time, faces coming together, lips pressed again, then they parted, tongues exploring, tasting, teasing, our breath coming fast. Her arms opened and pulled me to her on the bed. I fell to my knees then flat, and leaned into her, my own hands moving around and under her shoulders, the kiss never breaking.

One of her hands stayed behind me rubbing my back, the other went to my chest, fumbling at my buttons. One of my hands now went to the curve of her hip and grabbed one of her firm ass cheeks, caressing it. The kiss deepened then broke. We were face to face, both of us with our hands caressing the other. Our eyes met, both panting, mouths slightly open. A thought flashed in my brain. Should I continue? Push the issue? No words were said for what seemed like minutes yet only three seconds had passed. She answered my internal question by moving her mouth back to mine. Our tongues exploded back together in renewed passion.

Now our hands were making different moves. Hers went to my shirt and began undoing the buttons, an act she soon gave up on, resorting to tearing the buttons off. One of my hands still caressed her ass the other now went under the baggy sweatshirt and cupped one of the glorious globes that were her breasts. Her nipple hardened in my hand and she moaned into my mouth.

Our lips came apart and we started to move a bit frantically, desire and need taking over our actions. She pulled her sweatshirt over her head, I pulled my shirt off and stood starting on my pants, she knelt on the mattress, hooked her thumbs into the waistband of her sweatpants and thong, pulling them to her knees, I shed my slacks and kicked them to the floor, belt buckle clanking, she fell onto her back, giggling, legs together and knees drawn up, pulling her pants and thong off and kicking them to the floor, my boxers and socks were gone, we knelt naked, facing each other, inches apart.

My hand went out and back onto a luscious breast, our lips meeting again. Her hand ran down my chest, flat stomach and to my cock. She encircled my shaft at the base with her thumb and fore finger, her other three fingers cupping my balls. We both moaned. She fell onto her back. I was left kneeling on the bed, my cock level with her face. I leaned a bit forward. She smiled and leaned in, kissing the tip of my hardening sex tool.

Then it was gone. My cock disappeared between her lips and into her warm wet mouth. I gasped. She still held it at the base and cupped my balls, all the while giving me a blow job to die for. The efforts of her mouth, coupled with her stunning beauty as I looked down sent shivers of pleasure from the base of my balls all the way up my spine. She was, somewhat surprisingly, a talented cocksucker, using her mouth, teeth, tongue and hands to increase my pleasure. I finally leaned back and stopped her. It was her turn to enjoy.

I knelt down and she instinctively knew what to do, opening her legs. Her cute feet ended up on my shoulders and I got the first look at her pussy. It was beautiful, the outer lips glistening with her arousal. It was small looking, her pubic hair gone from around the pussy itself, only a neat light brown colored strip above. I leaned forward and her legs came open wider, her feet dropping behind my shoulders, her knees in the air. I gently kissed her outer lips, tasting her for the first time. So sweet. She moaned. My tongue traced her slit, parting the lips, stopping at her clit, flicking it. She gasped in a louder cry of pleasure. I paused and then went at it with energy, kissing and sucking her pussy lips, clit, inserting y tongue into her hot hole. She bucked and moaned, her well manicured hands in my hair. I drove her to her first shattering orgasm of the night.

"Oh God Dan! Fuck me, I need to feel your cock in me!" she panted.

I grasped my very hard cock in my hand, veins bulging, it's seven inches throbbing, head purple and glistening with pre cum. I ran my cock along her slit, teasing her, wetting the head even more with her after cum juices. Her hips rose, I placed the head at her opening and slid inside her tightness, feeling her pussy walls clench down on my rod.

I grabbed her legs, hands behind her knees, and gained some leverage, my cock like a piston driving in and out of her. We both gasped and moaned, enjoying fully the pleasure we were sharing. After several minutes of this and one orgasm from her I pulled my wet and slippery cock from her pussy. She turned over and went onto her knees. I knelt, lined my cock up and slid easily back in. I grasped her hips, her ass, as I fucked her. She crying out at every thrust, me grunting. She came again, her head thrown back, crying out in sheer pleasure, her pussy convulsing and gripping my cock. I couldn't take it any longer, feeling my balls tighten. I pulled out from her pussy and, using her love juices, stroked my cock once, twice, three times and with a loud grunt my cum exploded onto her ass cheeks, three, then four thick ropy strands of cum.

We were both panting, gasping, collapsing onto the bed. "My god that was so hot!" She managed to say between breaths, her finger tracing along my jaw line.

"You are pretty hot babe," I got out between my own heavy breathing.

We kissed and laughed, both exhausted but sated from our lovemaking. We fell asleep side by side in the huge bed.

I slowly peeled my eyes open. The bedroom was dark, the other side of the bed empty, Jessica no longer there. Still naked I swung my legs over the edge of the bed and paused, rubbing my head. I had just fucked one of the more recognizable faces in the American pop world. She was married. I was married. I wanted her again right then. Down boy, I told my libido and my stirring cock. I spied a bathrobe on the chair across from me and rose, wrapping myself in it.

I exited the bedroom and the rest of the suite was bathed in the mid morning light, sun streaming through the windows. "Good morning sleepy head," Jessica said from across the dinette. She was sitting on a window bench, cradling a cup of coffee, wrapped in the same type of hotel robe I was in. She sat with one leg curled under her, the robe partly open. I could see a portion of her smooth thigh and that stirring happened again. I stopped my feet before I ended up across the room. I went for a cup of coffee instead and then took a seat in one of the chairs several feet from Jessica.

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