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A Lucky Night with Taylor

I wouldn't call myself the biggest fan of Taylor Swift, but I did enjoy her music, and found her incredibly attractive. My friend had managed to get tickets for her upcoming Reputation Tour. They weren't just any tickets, though. They also included backstage passes to meet her afterward. My friend was an event planner for the arena Taylor would be performing at, so this entitled him to a free pass. He knew I had a crush on Taylor and liked her music, so he decided to give the pass to me. I owed him big time for this one.

The night of the show, after what seemed like an excruciatingly long Uber ride, I finally arrived at the arena. It was packed with young preteen girls and their moms, who no doubt weren't as lucky as I was because they had paid a fortune to be here. There was also a large contingent of middle-aged men who were here. I bet they enjoyed her body more than her music--not to say I didn't agree with them. Taylor is stunning, and anyone would be lucky to spend a night with her, but I also enjoyed her music.

After scanning over the crowd of people, I finally saw the entrance and headed into the arena. I pushed through the enormous crowd and found my seat. It was spectacular. I was no more than ten rows from the stage, giving me a perfect view to see Taylor when she appeared, and when she did take the stage, it was glorious. She was as hot as ever. Her outfit was almost the same as the one she wore for the Victoria Secret Fashion Show, except this time it was in all black. It was all black except for two things: her finger and toe nails were painted a vibrant red, and it couldn't have been hotter. Seeing her on stage dressed like this made my pants tighten. She pranced around on stage, dancing, gyrating her hips and sweating, and it was one of the sexiest things I had ever witnessed live in person. The fact that I knew I was going to be meeting her in person in a few hours didn't help my growing erection. It was a struggle, but I knew I had to do my best to hide it given my surroundings.

Two hours later and the show finally came to an end. Taylor walked off stage, thanked the audience and headed for her dressing room to prepare to meet her fans. So, as the crowd began to file out, I made my way to the stage to finally meet Taylor. There I was greeted by my friend who got me the ticket. "Thanks, man. I owe you one," I said.

"No, more like you owe me a few million," he said with a sly grin. He knew about my crush for Taylor, and how excited I was to meet her. He led me to the line that was forming in front of her dressing room, which had now been turned into a makeshift meet and greet room. As he turned away and left, he gave me one final 'have fun' accompanied by a wink. God, I really did owe him a million after this.

I took my spot in line. I was at the end behind girls of all ages with their parents, guys and their girlfriends, and again, a few middle-aged men. As I got settled into my spot, the two huge security guards opened the door to let the fans start to file in and meet their "Queen." The girls screamed, and the line began to move. One after one her fans went in and came back out. Some came out with autographs, while some girls walked out completely sobbing. I guess it was emotional meeting your idol.

After what seemed like an hour, it was finally my turn to meet Taylor. As I got to the door, the security guards checked my badge and let me into the room. I was then greeted with the most beautiful sight ever--Taylor Swift was sitting on a sofa in her dressing room. She was even more stunning in person. She had changed out of her concert outfit and was now wearing a white tank top, tight red short shorts and black flip flops. Her nails were still adorned with the sexy red nail polish. I couldn't believe this was happening to me. The security guards led me over to the sofa so I could sit with Taylor. My heart was racing the closer I got to her, and I couldn't help but to wonder if she could tell how nervous I was.

I finally got to the sofa. It seemed like my legs were working in slow motion. I sat down next to Taylor and introduced myself. "Hi, I'm Jake. It's a pleasure to meet you. I'm a big fan, but I'm sure you hear that all the time." I was stammering, my mouth not working properly. I was so nervous having one of the most beautiful women in the world not more than six inches from me.

"Nice to meet you, Jake. I'm glad you enjoyed my show," she said with a smile. As I looked at her, I happened to notice she didn't appear to be wearing a bra under her tank top. I saw the slightest outline of her tiny nipples poking through the fabric. The room was a bit chilly, and her body acted accordingly. "I notice you're not the typical fan I get at these meet and greets. Usually a handsome guy of your age has a girl wit them."

Did Taylor Swift just call me handsome? I swear I heard that right. "Yeah, I don't have a girlfriend. I'm just here for you, well, your music that is." Real smooth. She smiled and thanked me again. We kept talking about the usual stuff, like what my favorite song of hers was, and my favorite album, but then the topic shifted.

"So, what do you do for fun? What are some of your hobbies?" Taylor asked with a smile.

"Well, I'm a chef, actually. I work in a little Italian place in lower Manhattan. Kind of a thankless job that doesn't leave much time for me, but when I do get some me time I enjoy playing baseball. It has always been a second passion of mine."

"Wow," Taylor said, "quite the everyman I see. That explains why you don't have a girlfriend. Such a busy man, but quite the catch--a man who can cook, plays sports, and has rugged good looks."

Ok, that time there was no mistaking it. Taylor said I looked good. She is definitely flirting with me, but I thought she was seeing someone. I had to ask now. "Taylor, if I didn't know any better I'd think you were flirting. What would your boyfriend think?"

"Well, actually, I'm currently single. Like you I've been busy. Y'know, writing a new album, setting up tour dates and rehearsals. Doesn't give me much free time," she said with a sexy grin. She was looking me up and down now after that question, clearly eyeing my body. "...but I am free tonight," she said, "and I'd love to see your little Italian restaurant in the city if you're not busy." I looked at the time; it was nearly 10:30. We were talking for almost thirty minutes. I didn't even realize the security guards had stepped out of the room.

"Well, I'm not busy tonight either. I'm sure I could get us in and cook us up a late-night snack," I said with a wink.

She smiled at me and said, "Great! It's a date then. Let me just get ready and we can head out. Meet me around back of the area. I'll have my limousine take us." I couldn't believe this was happening. I was going on a date with Taylor Swift. I got up as quickly as I could and began to head out. She told her security team that she was heading out and to not expect her back until later.

I headed around back to the parking lot. A black limo pulled up, and out came Taylor looking as sexy as ever. She wore a black dress with a deep V down the middle, which showed a lot of cleavage. The dress only came up to about her thighs, so I had a great look at her sexy legs. She also wore sexy black high heeled sandals with clear straps. I climbed into the limo and she walked around to the other side. She had one of her security guards load something into the trunk. I didn't see what it was, but it sounded heavy. When she got back into the limo we were finally off to Manhattan. We made small talk along the way, talking about our childhoods, our favorite things to do in our free time and old relationships. We had a great time.

We finally arrived at my restaurant around midnight, and thankfully I had a spare key to let us in. I seated her at one of our private booths and I headed into the kitchen to cook us something. I quickly whipped up some gnocchi with a light pesto sauce and brought it out with a bottle of wine. "Your executive chef won't be pissed you made this?" she asked.

"Nah, we're really close. I'm sure he'd be happy knowing it went to feeding Taylor Swift." I winked at her. She began to eat and was clearly loving it. She was moaning almost every other bite and exclaiming how delicious it was. She finished hers before I even got close to finishing mine. Putting on a two-hour concert clearly made her hungry. Noticing her glass was empty, I took the initiative to poor her another glass of wine and she smiled. I finished my meal as we made more dinner conversation.

"Damn. A man who can cook this well deserves someone to cook for," she said. "And not to mention, someone as sexy as you definitely deserves someone."

Did she just call me sexy, or was that the wine speaking? I hope not because she's barely had two glasses. "I'm sorry, what did you just say? Did you call me sexy?" I asked.

"Don't pretend you haven't noticed me checking you out all night. I also saw you running your eyes all over me." Ok, she is definitely flirting now.

"I--" I was cut off in surprise when I felt something work its way up my leg toward my crotch. Apparently over the course of dinner Taylor had taken off her shoes and was now using her toes to fiddle with my cock through my pants. I instantly got hard. I quickly leaned over and put her lips to mine. We began to furiously make out in the booth. Our tongues fought for dominance in each other's mouths.

After a few minutes of kissing and groping, Taylor managed to mumble against my mouth, "Let's head back to your place."

Luckily, I didn't live too far from here, but against my better judgement I said, "You don't have anything else to wear and I don't want to have you leave some random Manhattan apartment wearing a wrinkled dress. It would be suspicious."

She smiled at me and said, "That's why I packed a bag. It's in the trunk. I was planning on this." I couldn't get to the limo soon enough. We both got in and made our way to my apartment. Ten minutes later we got out. Taylor told the driver to head back and that she would be spending the night with me. We made our way up the entrance stairs. I took her bag as we headed in. When we got to the elevator our lips came together again. Tongues and teeth clashed. My hands grabbed her perky breasts through her dress. She reached down and grabbed my erect cock through my pants. The elevator stopped at my floor and we got off. We were still furiously making out as we headed into my apartment and toward my bedroom. Clothes were scattered in a line from my front door all the way to my bed. By the time we reached my bed, Taylor was left in nothing but a black strapless lace bra and matching panties. I only had my boxer shorts on as we came down onto the bed, mouths still attached. We finally managed to separate our lips to catch our breath.

"Fuck!" I exclaimed. "You're so damn sexy." I looked her up and down partially to make sure this was actually happening, and to look at her stunning body.

"You're not too bad yourself, Mr. Chef," she said. "Now, let's get you out of those boxers so I can finish what I started." She slowly peeled down my boxers and my erection sprung out. "Fuck, that's big. Can't wait to get that inside me, but first it's time for a warm up." Taylor then reached around her back and snapped off her bra. Her small but perky tits spilled out. She had the most perfect tiny, pink nipples. She then pulled down her panties to reveal her pink, shaven pussy. She was beautiful. As I looked her naked form up and down, she took my cock in her hands and put it between her feet. She began sliding her soles up and down my hard shaft using my precum as lubricant. I moaned in pleasure as she continued stroking my cock. "I noticed you staring at my feet as you walked in, and then when I had my heels on. You wouldn't happen to have a foot fetish, would you?" she asked with a sexy grin.

The only word I could get out was a whimpered "yes." I was too enthralled by the feeling to get anything else out. She continued to use her sexy pink soles to stroke me up and down as I moaned. But then it got even better--she introduced the tip to her mouth. She continued to alternate between licking and sucking as she moved her feet up and down my hard shaft. After about ten minutes I warned her I was about to cum. She pulled away.

"We wouldn't want that before you had a chance to fuck me," Taylor said.

"No, we wouldn't," I agreed. "Now it's my turn to please you." I pushed her onto her back and attacked her wet and waiting lips with my tongue. I began to lick her pussy up and down. She moaned in pleasure. I then began to attack her throbbing clit with my tongue. She cried out almost in pain, but I knew she loved it.

"I'm gonna cum!" she screamed. "Goddamn-fuck!" Just like that she came in my mouth. Her juices tasted amazing.

"Goddamn that was hot. I hope I didn't wear you out," I said. She answered back by attacking my lips with hers.

She then pushed me onto my back and straddled me. "No, you didn't," she said, "not even close. Now get ready for me to fuck your brains out, Jake." As soon as the words were out of her mouth she impaled herself on my cock. We both moaned in pleasure. She began to ride me up and down.

"Shit, ugh fuck, fuck, fuck me Taylor; ride that cock." She began to pick up the pace as she rode me up and down. After a while we were both panting, moaning and coated in a sheen of sweat as our intense fucking continued. Noticing Taylor's breasts bouncing up and down with her thrusts, I reached up, grabbed onto the them and pinched her nipples between my fingers.

She cried out, "Fuck you feel so good, Jake. This is the best sex I've ever had."

All I could muster was, "Same, Taylor, same." As her bouncing and grinding continued, I reached around her back and flipped her over. I put her ankles on my shoulders and began to pump in and out of her. I looked to either side of me and saw her sexy, red-tipped toes curled from pleasure. Her red nails looked so sexy as they curled and splayed open with each push and pull of my cock. I then took her foot in my hand and licked up and down the arch. She moaned loudly. I licked and kissed her soles as I continued to drive into her welcoming pussy. After I licked the bottoms of her feet, I introduced each toe to my mouth and sucked on them. I began to suck on one of her big toes as I drove into her.

She moaned out, "You like sucking my sexy toes as you fuck me? You love my red toe nails and my pink soles, don't you?" Fuck, she was so hot.

"Fuck, Taylor. I love your feet. I love your tits, and your wet pussy. You're so fucking hot!" I shouted. God, she felt so good.

"Good, Jake. Fuck me--fuck me until I cum," Taylor groaned out. "I need to cum! I haven't in so long."

"Neither have I, Taylor. I needed this!" I kept thrusting as I felt my release barreling toward me.

"Fuck! Jake, I'm cumming!" I felt her walls tighten around my cock as she began to cum. This sent me over the edge as well.

"I'm cumming, too, Taylor! Where do you want it?" I didn't know if I could wait for her to even answer.

"Wherever you want, baby. Wherever you want!" With that I pulled out of her pussy.

"I want to cum on your feet." She quickly rolled over onto her stomach and presented her soles to me. I began to stroke myself and rope after rope of sticky white cum came out. "Ahhh!" I moaned as I shot my load all over her pink soles. I was spent, and so was Taylor. I crashed onto the bed beside her as we both tried to catch our breath.

"That was the best sex I ever had! I really needed that." I had to agree with her. This was definitely the best sex I ever had.

"I couldn't agree more, Taylor. I'm just still trying to process the fact that I fucked the girl of my dreams."

She laughed and playfully slapped my bare chest. "No need to flatter me; we already fucked." We both laughed.

"I guess now I owe my friend a billion favors for hooking me up with that backstage pass."

Taylor laughed. "Yeah, probably. I'm gonna take a shower and then get changed. You wiped me out. See you in a few." Taylor got up and headed toward the bathroom. She closed the door and I heard the water start. I drifted off into a blissful sleep. I didn't even feel Taylor hop into bed with me. I must have been absolutely wiped out after our marathon.

When I awoke the next morning, Taylor was lying in my arms wearing nothing but a loose white t-shirt and green boy shorts. She looked even sexier in the morning. She began to stir as well. "Hey, sexy. Not a bad job last night. I really needed that," Taylor said.

"Thanks, me too." I got up and went to put a shirt on.

As I headed over to my dresser, Taylor said, "I normally don't do that on the first date. You're so hot, though, and damn I just needed that. I hope we can do this again sometime. Maybe after a few more official dates?"

Was she asking me out? Like to be her boyfriend? "Taylor, are you saying you'd like to go out? As a couple?" I couldn't believe this was happening.

"Yeah, like I said, you can cook, and you play sports. You're a catch. I'd love to be the woman who gets you." I owed my friend for the rest of my life.

"Absolutely Taylor! I'd love to go out with you." After that she smiled and we both got dressed. We exchanged phone numbers and agreed to do this again real soon. I kissed her goodbye as her limo pulled up to take her back to the airport for her next show. "See you soon," I said.

"I hope sooner rather than later." She smiled as she got in the limo and said, "Don't worry about my reputation. I plan on staying with you for a while. Even if it's just for sex and gnocchi." She smiled again and waved goodbye. I must be the luckiest guy on the planet.
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