This is a fictional story I wrote. It's not real, but I wish it was. Don't copy my story to put on another site. This is just fantasy, blah blah blah. You know the rest.
If you want to read about the first time I fucked Britney Spears,
click here. If you're interested in the (so far) two documented times I fucked Kate Upton, click
here and
here. Enjoy the fucking show.
The days turned into weeks and now two full months since the day I met Britney Spears. Her team worked me like a mad dog. Everything about her was hidden in some kind of strange secrecy. The security team had to know everything she was doing and everyone who was visiting her. It was an open secret that she had been fucking me. That seemed to be fine by standard protocol as part of the spoils of my job.
Britney worked tirelessly at her shows. Even if the songs were lip-synched, it was still amazing to see how much she worked nightly on stage. She was doing four shows a week. I had sat in over a dozen of them so far and never got tired of watching her move around on stage in outfits that revealed her sexy body. There was barely anything to the sheer fabrics, bras and thongs she wore. I heard her old hits so many times, it took me back to a place of happy memories.
And then Kate Upton called me one day out of the fucking blue. Surprises come when you aren't expecting them.
Kate wanted to know why I had not called her or even texted in a few months. She was understandably upset about how I neglected her when we had a solid relationship going. I explained to her that I was signed on a new job, working P.R. for Britney Spears. She was quite impressed. "Britney Spears? Really? Wow. She must have you by the balls if you aren't going back to L.A. anytime soon."
That was sort of true, I explained to Kate. It wasn't Britney's fault. I'm sure if I told her I wanted to leave Vegas for some off time, she would've been fine by that. But Britney had no control of the inner workings of her team. I explained to Kate that the situation was strange with how cutthroat her team was. I left out the real details. There was no point in telling her that Britney appeared to be a prisoner stuck working in Vegas at the beck and call of her handlers. What mattered was learning that Kate had an apartment in Vegas she was renting out for vacations. That was something I had no clue about until now.
I was Britney's favorite guy right now. We fucked once a week and she knew how to keep me happy. A complete nympho who loved sex and could go for hours on end with multiple orgasms. I couldn't get enough of fucking her. Everything about her body was perfect. We fucked in every room of her large penthouse. One night she went to my room and made sure to fuck me in the bedroom and bathroom just to say we had done it there. There was no better feeling than when she was on her knees sucking your dick. It was enough to make you weak in the knees.
When I told Britney that I was friends with Kate Upton, her jaw dropped. "Kate Upton!? You mean that model with the really big boobs on the cover of Sports Illustrated!?"
Britney didn't have to say anything else. She got her point across that she was attracted to Kate, but then she went on about wanting to meet her. I told Britney about my relationship with Kate and how I had been fucking her off and on for some time now. The MILF was impressed. She made me an offer to invite Kate to Las Vegas and arrange a threesome. How could refuse such an offer?
So I did it. I called Kate and invited her. She was busy at the moment shooting a commercial, but was willing to step off the set to join me for a weekend break in the city of sin. She told me she would be in town soon staying at her apartment. When I told Britney about the talk we had, she was happy, but there was a dilemma. She had a show on the night Kate was arriving. It wasn't enough to stop Britney. She demanded to have some fun after the show, but wanted to meet Kate first. I had a job to do now.
As I drove my car to pick up Kate Upton, my heart raced with anticipation. It wasn't every day that I got to introduce my friend and boss Britney Spears to someone as gorgeous as Kate. The idea of the three of us together was almost too much to handle. I couldn't help but wonder what kind of chemistry they would have. Of course, I knew that Britney was a total pro when it came to women, but Kate was on a whole other level. Her perfect curves, those amazing tits, and her gorgeous blue eyes that seemed to sparkle with mischief. She was everything a man could ever want.
When I finally pulled up to the address of Kate's apartment, I took a deep breath and tried to calm my nerves. I was so excited, it was hard to control myself. I beeped the horn of my car and a few seconds later, she opened the front door. She was wearing a tight white tank top that showed her huge cleavage and a pair of black shorts that barely covered her ass. I had to check out her legs and the black stilettos that showed her toes. Her long, wavy hair flowed down her back, and she flashed me her pearly whites in a dazzling smile.
Kate grabbed the door and opened it. "Hey there, James. Thanks for picking me up." She climbed into the car and shut the door. I leaned over and kissed her on the cheek. She insisted on a quick kiss on the lips.
"Looking sexy as usual, Kate." She smirked when I said that. "Well, I guess I could dress to impress since today I'm meeting Britney Spears. I can't believe you've been working for her. It's not like you to be out in Vegas away from Hollywood."
"Well, I was given the chance and I had to take it," I said, nodding. "Working for Britney was one of my dreams when I started in this business. I'm just glad I get to do more than work for her, if you know what I mean." I shifted gears and pulled off from the block. Kate twirled a strand of her hair with her fingers, giving me subtle looks. I wondered what she was thinking about, but it was pretty obvious. That look. The smirk she made told a story in itself. Kate knew me all too well, as I also knew her. This wasn't a social call or a fan meeting. It was going to be a slumber party between the three of us.
We made our way through the Vegas Strip. Along the way, my cellphone went off in the pocket of my jacket. I answered the call from one of the security guys back at the hotel. "Hey, I'm on my way. Tell Queen B that I've got Kate Upton coming up to meet her." Kate laughed as I hung up the phone. "Queen B, huh?"
"That's what we call her in the team. She is the queen after all." She giggled at that nickname, shaking her head. I could see the mischievousness in Kate's eyes. Britney reminded me a lot of her, especially when it came to the near-addiction Kate had for sex. I was already thinking about just how wild this night was going to be when I pulled into the parking garage.
We got out and took the short walk to the hotel. The security team checked in with us at the elevator. Kate was cool, calm and collected. I relaxed seeing how comfortable and confident she looked on this short trip to meet the Pop Princess. When we got to Britney's room, I opened the door for Kate.
"Kate! You made it!" Britney exclaimed as she saw her. She was dressed in a sexy black lingerie set, her long legs and toned stomach on display. Fishnet stockings covered her strong legs and she was wearing a diamond navel piercing. "Come in, come in!" She gestured for Kate to enter the room. "I'm so glad we could finally meet."
Kate walked in, smiling at Britney. "I'm really glad I could make it. I always dreamed of getting to meet you!" She glanced over at me and winked. I could tell that she was just as excited as I was about having these two hot blondes together in the same room. I shut the door and joined them.
"Thanks for bringing Kate Upton over!" Britney gushed, giving me a hug. "I've been looking forward to this all day." She pulled back and looked at me, a mischievous grin playing on her lips. "I've been thinking about what you and I talked about yesterday..." She trailed off, letting the words hang in the air.
Kate's eyes widened and she glanced back and forth between us. "You two have been planning something naughty?" She asked with a sultry grin.
Britney giggled and walked over to her. "Of course, Kate. This isn't just a meet and greet! I have a show tonight and James is your date. After I'm done, we're gonna come back up here and have some fun."
Kate's blue eyes sparkled with excitement as she nodded. Britney pointed at me. "James, show Kate to her room so she can get comfortable. The show don't begin until later tonight." I nodded and escorted Kate out of Britney's penthouse, back into the hall. Britney reserved a private room for her just one floor lower that was for her special guests. It was one of the few things she was allowed to do under heavy restriction of her handlers. Kate got settled in the room with me, smirking as she crossed her arms over her busty chest.
"Well, that was a short meeting. I guess she's saving all the fireworks for the show. What about the afterparty?"
"That's gonna be the real show. All the dancing and ass shaking she'll do on stage will just get her in the mood and make her horny."
"Did you see how she was dressed? I think she's already horny, James." I laughed, nodding. "Yeah, that's how she is. If it weren't for these shows, I'm sure Britney would spend all day getting fucked."
Kate raised an eyebrow, her blue eyes sparkling with mischief. "Too bad we can't have a practice session right here and now. I guess you want to save all your energy for both of us."
Blushing, I smirked at her. "Yeah. I gotta say, Britney fucks like a porn star."
"Oh, really?" She asked. "Yeah, really. She's a complete nympho MILF. A full blown sex addict if you ever knew one. The way she fucks is unlike some of the best I've had, and you know I've fucked a lot of women in the business."
"Does she give better titfucks than me?" Kate smirked again, knowing I wasn't going to tell her to her face that another woman was better at the one thing she had the most expertise in. I knew how to play this cool and reassure her.
"Kate, let me be the one to tell you, no one tittyfucks better than you. You're the best." I leaned in and kissed her lips. "Thank you, that's just what I wanted to hear. Since we have to wait for the show, I want to go shopping for a better outfit to wear."
"That's cool. I'll call up security and they'll take you to any store you want to go." Kate shook her head and grabbed my arm. "Not so easy, Mr. Scandalous! You aren't sending me out with bodyguards just so you can spend time with your new MILF."
I blushed, trying not to smile as she started laughing at me. "Fine, I'll take you out. But I want to make some calls first. Let the paps come out and get shots of us down the Strip." I winked, knowing Kate wasn't going to turn down the opportunity for the paparazzi to get some good photos of us. It would be good publicity with her in Las Vegas. It would be even better to spin the whole tabloid that Kate Upton was in town to see one of Britney Spears' shows.
Twenty minutes later we were out the door, stepping out of the hotel and back on the streets. I called one of the managers with Britney and let them know to start making calls to TMZ. An hour out in Vegas, the paparazzi photographers were outside the shops with their cameras ready. This put me in my zone. I felt like the most important person in the whole fucking town as I opened the door for Kate and shoved the photographers back. She was carrying bags of clothes.
The hungry photographers were like vultures snapping pictures. I pushed them aside and took her hand, walking her to the car. I heard one of the men call my name and I turned back and grinned. It was going to be a good day tomorrow waking up and checking the internet to see my smiling mug with Kate all while thinking about what a good time we had with Britney. I got back in the car, she shut the door and locked it and we zoomed off, outracing the photographers. A short trip back to the hotel had me carrying her bags of clothes. Kate went up to her room and got dressed in her new outfit.
"How do I look, James?" Kate stepped out of the bathroom wearing a black top with tiny shoulder straps and a pair of black shorts that covered her thighs. Her huge boobs were pushed up, revealing cleavage. Her long golden hair was fixed up by herself and she had on pink lipstick. It was the same type of lipstick Britney was wearing earlier. "You look like the hottest supermodel in the world."
Kate rolled her eyes. "No I don't. I'd need to be in a bikini for that to be an accurate statement." We both laughed as I noticed her heels below. "Come on, babe. The show begins soon."
I had the honor of walking Kate out of the hotel and to the theater. We had to go through a mob of people, but there were no photographers present, so that was a blessing. I knew when the show started, my ears would be blasted by dance music and screaming fans. Britney's shows were always sold out and busy. I brought Kate to the front row as we anticipated the show to begin.
Finally, the lights went down and the music came on. The crowd roared as they saw Britney walking out on stage. She was dressed in a barely-there outfit that was more like a stripper's costume. I glanced at Kate, who looked amazed and excited at the same time. It was obvious she was exploding in excitement. The way she stared at Britney with that look in her eyes, it was clear she was imagining herself up there on stage with her. Kate was seeing one of her favorite songs dance and move on stage. The song opener was 'Toxic' to set the mood.
Britney began dancing and singing, and Kate couldn't take her eyes off her. Her lips moved as she mouthed the words to the song, and her body moved along with the beat. It was like she was possessed by the music. I knew this from watching shows. Britney always worked her ass off as the songs played on. I couldn't help but smile, watching her lose herself in the performance and knowing the fun we were going to have later. Kate was having the time of her life clapping her hands and cheering. Britney slid on the stage, arching her back to show off her sexy toned stomach. All the people around us pulled out their phones to record the moment. Britney looked at me and winked when she noticed how excited Kate was.
As the show came to a close, I guided Kate backstage where security were the only ones permitted to enter. She was still excited, almost shaking from the adrenaline rush of the sexy performance Britney put on. There was a row of fans lining up for meet and greet pics. One security guard told the crowd that the signings were cancelled tonight. The fans were upset, some of them moaning and groaning. I knew the reason Britney wasn't taking pictures tonight. There would soon be a different kind of moaning and groaning going on behind a locked door in her penthouse suite.
One of the security guards approached us, motioning at Kate with his hand. "Hey, Queen B wants to see your friend first." Kate gasped. "Britney wants to see me!?" The man nodded. "Yeah, come this way."
Down the hall I could see Britney poking her head from the corner, trying not to be seen by the angry fans. She motioned at Kate with that big megawatt smile. Kate dashed to her. "Come here! I need to ask you what size bras you wear. I got an outfit that I think would look great on you." Hearing Britney mention that gave me a small hint that she had something planned for me once I got up to the top floor. I was more excited than ever now. It had been a while since I last enjoyed the fun of a threesome. I was about to have one with my dream girl and the one I had the biggest crush on.
I took my time going up to the top floor. The elevator was a slow ride that I hoped would give enough time for Britney and Kate to make their preparations for my arrival. By the time I got to the door, I knocked a few times. "Come in, James!" said Britney's voice from behind the door.
I opened the door and stepped inside. The room was dimly lit, with the backing tracks of Britney's setlist playlist playing in the background absent of vocals. Britney and Kate were both sitting on her their knees on the bed. Both of them had on fishnet stockings and a lacy red bra with matching thong. It was an outfit Britney wore, looking like something straight out of a strip club.
Kate looked up at me with a sultry expression, her lips curled into a seductive smile. "Well, well, hello there Mr. Scandalous," she purred.
I could feel my heart racing as I took in the sight of them both. Britney motioned for me to come closer. "We've been waiting for you, James" she said, her voice as seductive as ever. I grinned and pulled off my jacket and shirt. They both got up from the bed and hurried down to their knees in front of me. Britney to the left, Kate to the right. They pulled off the bras first, revealing their tits. My eyes immediately watched Kate's bounce and shake as she teased me. Then they stood up to momentarily push their thongs down, revealing both wet pussies to me and stepping out of them in perfect sync. Just like that, they were naked in nothing but the fishnet stockings and high heels. They both fell back down to their knees and moved towards me.
Britney reached for the front of my pants, undoing my belt and the buttons before tugging them down my hips. I kicked off my shoes and socks, as the MILF worked my pants and underwear down. Kate kissed her way up my thigh, while Britney helped push my ankles out from the confines of my pants. I stepped out of my clothes, now naked as Britney reached for my cock and gripped it.
She looked up at me, her dark eyes shining with lust, and then Kate glared at me with her blue hues. Britney wanked my cock, stroking it to make sure I was hard and at full length. She then pointed it towards Kate. "Here, you get to taste him first." Kate smiled and licked the head before sinking it into her mouth. My dream girl bobbed up and down on it, taking me deeper, her tongue flicking out to tease the underside. She looked up at me, her lips wrapped around my shaft, and then back down to my cock as she sucked harder. Britney watched her suck and then looked up into my eyes. "She sucks you well."
Kate bobbed her head up and down, sucking me slowly while her hands played with her tits. When she slowed down, Britney grabbed my dick from the base and pulled it out of Kate's mouth. It was her turn to feast on my dick. Britney took me deep into her throat, her lips vibrating as she sucked. She looked up at me, her eyes wide with pleasure, and then shut them as she went down on my cock. Britney was sucking me hard and fast, bobbing her head up and down without missing a beat. She was aggressive with how she sucked to the point that Kate was frozen in disbelief. Kate was witnessing the true lustful nature of what a cock hungry MILF Britney really was. I groaned as she pulled my cock out of her mouth with a pop. Britney spit on it before pointing it towards Kate to have another turn sucking me.
Kate opened her mouth wide and took me back in, her hands massaging her breasts as she bobbed her head. The slower pace was drastically different from how Britney devoured my dick. She glanced up at me, her eyes meeting mine as she slowly sucked. This was only momentarily as Kate pulled back and released my cock with a similar pop sound to the one Britney's mouth made.
"Put it between your tits! I want to watch him fuck your tits!" Britney sounded so enthusiastic as she told Kate that.
Kate smiled and lifted her breasts up to meet my cock. Britney helped guide it between them, their soft orbs squeezing me tightly as Kate pushed them together. She spit on the head as it poked up, beating Britney to it who also had to spit on it. I started to thrust gently, feeling my cock slide in and out of their cleavage.
"Oh my god, that is so fucking hot." Britney moaned, watching as my cock slid in and out of Kate's tits. The supermodel bombshell kept her hands on her tits as I thrust harder and faster. Kate moaned as Britney watched the entire time. I wasn't sure if Britney was more turned on by this or Kate. The mere sight seemed to be making the MILF hornier than she already was.
I fucked Kate's tits harder. These were truly what I believed to be the best boobs in the world right now. The sensation of my cock sliding through the folds of her tits as I thrust was always another world of pleasure. I glanced over at Britney, who was practically salivating as she watched us. Kate noticed her and smirked. "You like watching him fuck my tits, huh?"
Britney kissed Kate on the lips, completely distracting me. I stopped thrusting and watched the two blonde women lock lips for a loving kiss. Kate let go of her tits and I snatched my cock free. Britney pressed her chest against Kate's as they continued to kiss passionately. "Looks like I'm not the only one who likes kissing Kate." I spoke to distract Britney. She stopped kissing the supermodel and then grabbed my cock.
"I hope you're ready to fuck us with this big, scandalous penis." She smiled, her lips curling into a wicked grin.
"You know I am!" They got up from the floor, both of them turning to face the bed and showing me those plump asses. As they climbed on the bed, I moved right behind them, starting with Britney first. I lined myself up behind her and slapped her ass. Kate crawled in front of her, sitting down in front of Britney's face with her wet pussy ready to be eaten.
Britney glanced behind her right shoulder to watch me as I slowly pushed my cock into her. It was tight, just the way I liked it, and I groaned as I began thrusting. "That's it, James! Fuck me!" God, I loved hearing the princess of pop tell me that like she was singing a verse to a song. Kate reached down and rubbed her clit as she watched me fuck Britney. Kate got to see the look on Britney's face as I took her, and that made her grin smugly. "Feels good when he fucks you, huh?"
I glanced over at Kate as she looked down at Britney. I could only imagine the look on the MILF's face as I started thrusting harder and faster. Britney moaned. "Fuck me! FUCK ME!!" She glanced forward and saw Kate's fresh, wet cunt. Britney didn't ask as she lowered her face and slithered her tongue inside Kate, making her gasp. "Ohhhhhhhhh, GOD!!"
Kate moved her hands around Britney's head, her fingers tangling in her hair as she was eaten out. It barely took Britney any time to slither her tongue deep enough to reach Kate's G-spot. I could see her body trembling as she came down from one orgasm, only to be sent right back up by the way Britney was eating her out. "Fuck... I can't... I can't... Ahhhhhhhhhh...!"
I kept fucking Britney, enjoying the feel of her tight pussy with every thrust. Her tits were shaking underneath from how hard I was giving it to her. I watched Kate experience her first orgasm of the night, unleashing a torrent of her cum into Britney's talented mouth. The singer swallowed it all and raised her head. "Ohhhhh, FUCK!! I'm so CLOSE!! JAMES, MAKE ME CUM!! FUCK MEEEEEE!!"
I picked up the pace, fucking her harder, faster. "You like that, Britney? You like getting fucked hard after a long night dancing and shaking that ass on stage? Ohhhh, yeah! I bet you were thinking about my cock when you were singing earlier tonight!" I was taunting her. Britney knew how to bring the beast out in me and I couldn't stop fucking her. It was my mission to make the MILF cum.
Kate had recovered from her first orgasm and was watching me fuck Britney. Her eyes widened. Kate had never seen me fuck another woman before and she now had a front row center view of watching me take one of the hottest women in the world. Britney clutched the bed sheets, squealing as she orgasmed. "Ohhhh, GOD! JAMES! FUCK! I'M CUMMING!!"
I pulled out before I could cum. There was no sense in wasting in my load in Britney's cunt when I could make a mess out of them later. Breathing heavily, I moved over bed and saw Kate's big blue eyes. "You're looking a little tired James. Is she too much for you?" I shook my head. "Hell no!"
"I hope that means you're ready for me!" She pressed her huge tits against my chest, kissing me hard. Britney was still recovering from her orgasm when she watched Kate shove me down on the bed and take control. She straddled me and got on top, holding my cock up to properly lower her pussy down atop it.
"Oh, God, yes!" Kate moaned as I began thrusting into her. "Fuck him, Kate! That's it! Make those huge tits shake for him!" Britney was cheering her on as she was the only member of our audience. Kate's big breasts bounced with every movement and I could feel her tightness grip me as she rode me. Britney rose to her knees, sitting up. Kate leaned over and kissed Britney, their tongues dancing together as they shared the moment.
I was lost in the sight of them, the feel of being inside Kate. She moved her hips in a perfect rhythm, grinding down on my cock. Her breasts swayed, her nipples hard as pebbles. She looked down at me, her eyes dark with desire, and then back up at Britney. "You're right, I am feeling a little selfish..." Kate reached behind her and grabbed Britney's hair, pulling her in for a deep, passionate kiss. I saw an opening to take advantage and begin bucking my hips to drive my cock in and out of Kate's cunt.
"Oh my god!" Kate gasped as I took her by complete surprise. Britney clapped her hands. "Fuck her, James! Fuck her!!"
To have Britney cheering me on like that, I leaned forward and rolled Kate onto her back. Her huge tits were pressing into my chest as I started bucking my hips as hard as I could. I fucked her as hard and as fast as I could with my dick pounding that pussy rapidly. "OHHHH, OHHHHHH GOD!! GODDDDD, YESSSSSS!! FUCKKKKKKK!!"
As Kate screamed her lungs out, Britney moved to my left side, I reached for the MILF singer's golden hair and grabbed it, pulling her face to mine. We were kissing tenderly as I fucked Kate into an orgasm. "FUCKKKK!! OHHHHHHHH, JAMESSSSSSS!!"
I got off Kate and pulled out as quickly as I could. Britney helped her sit up as she moved on her knees. The look in Britney's eyes was one of pure lust. She knew I was holding back from blowing my load. "Come on, Kate! Let's make him cum! I want his cum dripping from my face, what about you?"
"That's where I want it too." Kate nodded eagerly and moved forward, kissing Britney passionately. I was standing in front of them, fingers gripping my cock as I aimed it point blank at their faces. Britney was on the right, Kate to the left. Their kiss ended and Britney knew just what to do. She pressed her face against Kate's as I continued to stroke my dick. They both opened their mouths at the same time and closed their eyes, as if they were desperate to feel my cum raining on their skin. "Ahhhhhhh!" Their voices intertwined, tongues still out.
"Here it comes..." I moaned. "Oh fuck!" I exploded, shooting thick ropes of cum all over them. Some landed on Britney's tongue and her right cheek as she tried to catch as much as she could, but most of it splattered across Kate's perfect skin. My cum coated Kate's forehead, her lips, her chin, her neck. I pointed at Kate, making my choice between the two blondes and kept jerking until my cock was finally spent.
"Oh my god," Kate breathed, her chest rising and falling rapidly as she caught her breath. "I got blasted." She kissed Britney again, their tongues tangling as they shared the taste of my cum. I felt like the man at that moment, more proud than ever. Britney broke the kiss with a stand of cum dangling from their lips. It broke and she slurped it up. "Wow, he gave you most of the load. I only got one string of it." I laughed at her complaint as she smiled at me, looking a little disappointed she barely received any of my load and Kate ended with most of it.
"Well, he hasn't got to fuck me in months!" Kate teased, wiping some of my cum from her cheek with her finger. She held it up to show me and then licked her finger clean. "I guess this is James way of saying he missed me." I blushed as Britney laughed. Kate always knew how to make my heart melt. I climbed off the bed and fetched my shirt, tossing it at them so they could clean their faces. A few minutes later, I was in the middle of the bed between both girls ready to fall asleep. Britney was to my right and Kate on the left, both resting their heads against my chest. Worn out and spent, I was happy to be going to sleep between two angels. Life could feel like heaven on earth with the right women.
Topic: Las Vegas Double Trouble (Britney Spears, Kate Upton) (Read 61557 times)