Opening For Taylor Swift Sex Story

“Welcome to the American Union Hotel sir…how may I help you?”

“Yes, I’m here for the ‘Cancer Takedown’ charity event. I’m the opening musical act Rob James.”

“Okay Mr. James, your dressing room is down the hall and to the left. Here’s your key”

This day, the first Tuesday of the month, was my chance; my first performance in front of a large audience with the pressure of opening for a worldwide star. I was opening for Taylor Swift and I was nervous about everything. I had been performing my country songs in front of small audiences of no larger than around fifty people, but this was in front of at least a thousand. I had just turned 24 and was hoping this show could lead to something.

I was unlocking the door when I heard a door close behind me. I turned around and there she was.

“Hi, are you the opening act?”

“Yes. Rob James.”

“How long have you been singing?”

“About two years, but I never performed in front of more than fifty people before. This is by far the biggest crowd I’ve seen. I hope I don’t screw up.”

She smiled. “Don’t worry, I remember my first big show…I was sweating like crazy and shaking badly. You just need to concentrate more on your music than what the crowd thinks and if you do that you’ll be just fine. I have to go get ready so I’ll see ya later.”

I entered the room and quickly changed as I only had 25 minutes before I had to be on stage. I sang all three of my songs to make sure I could get through them without issue.

The charity director knocked on my door. “We need you on stage in two minutes, Mr. James.”

I walked on stage and looked around through the crowd. This was definitely the largest crowd I’ve ever been in front of. As I looked around, I noticed Taylor was standing in the back as our eyes met. She gave me a smile and a wave as the band began behind me. I started with the song I thought was the best I had, “Taking It Down”. The crowd seemed to like the song very much, which helped my confidence greatly. When I was done, the entire crowd clapped very loudly. I looked through and didn’t see anyone that wasn’t cheering. I looked back at Taylor and saw that she was clapping as well and was the last one to stop.

“Damn, she must have really liked it.” I thought to myself.

My other two songs went by and the crowd never seemed to die down.

“Thank you very much everyone. I hope you all enjoyed the sounds of Rob James. And now for the person you all came to see…Taylor Swift!”

Taylor walked up and gave me a hug before I walked off the stage and headed for the bar.

“Wow, I don’t know how I can follow that but I’ll try.”

Taylor got through her first four songs, as the crowd was still very into the concert.

“Okay, we’re going to take a fifteen minute break and then we will continue!”

Taylor walked over to the bar and sat down next to me.

“Hey Rob, you were awesome up there.”

“Thanks, but I’m still nowhere as good as you are.”

“Hey, I’ve got a great idea. Do you know my song ‘Love Story’?”

“Of course I do.”

“Do you want to do a duet of that song with me as my final song?”

“Sure, but what parts will I sing?”

“Did you see my special with Def Leppard?” I nodded. “Just sing his parts and we’ll be fine, okay?”

“Sure thing Taylor.” She kissed me on the cheek, got up and headed for the stage.

She continued her set before the time had come.

“Okay guys, for my last song I’m going to need a little help. Let’s get Rob James back up here for a special duet performance!”

The crowd applauded as I got back to the stage. The duet went smoothly as the crowd again got loud with applause as we thanked everyone for coming out.

“Thanks for coming out everyone.” Taylor said. “Because you guys were so good, I will be donating one million dollars to the ‘Cancer Takedown’ organization and I will come back again very soon.”

After I left the stage, I headed back for my dressing room to pack up and leave. As I got to the door, Taylor stopped me.

“Hey, I’ve got a room here, let’s go up and celebrate our perfomances.”

“Okay, I have to pack up my stuff first and then I’ll be up.”

“Cool, here’s my key. It’s room 498…see ya soon.”

I quickly packed my guitar in its case and grabbed my suitcase. I headed up the elevator to meet up with Taylor. I knocked on the door and she let me in.

“Hey Rob, take a seat and I’ll get you a drink. What do you want?”

“Just a water, I don’t drink alcohol.”

“Neither do I, I just wasn’t sure if you did.”

She came out with both glasses and sat down in the chair next to me. We sat there and talked for a good half hour about different things, but mostly music. After a while, the questions got more personal.

“Are you single?”


“That’s a shame, someone as cool as you shouldn’t be single.”

“I know, but I’m really into my music and I can never find a girl who understands that.”

“I’m used to that, most of my relationships are really short because I put so much into my career.”

“I guess that’s just a sacrifice we have to make for…” Suddenly she jumped from her chair and stuck her tongue down my throat. I kissed her back as she ran her fingers through my hair.

“I need you so bad. I don’t know what it is but something about you and your music made me so wet out there.”

Before I could say anything, she forced her tongue back in my mouth and we kissed long and hard again. She began unbuttoning my shirt as I began caressing her ass. I reached up and pulled her shirt over her head revealing a pink bra. Everything was moving fast as now my pants were around my feet, leaving me in my underwear.

“I see someone is excited.”

She said as she noticed my hard nine-inch cock poking at my underwear. She removed her skirt revealing a matching pair of pink panties. After kicking her shoes off, she yanked down my boxers and stared at my cock.

“Holy shit! That is a big cock. I’ve never seen one this big.”

She removed her underwear, leaving us both completely naked in front of each other. She didn’t have large breasts, but I wasn’t one for big breasts anyway. She had shaved her pussy completely which gave me a clear look at her tight pink pussy. She had a nervous look on her face.

“What’s the matter Taylor?”

“I want to suck your cock, but I’ve never done it before.”

“It’s okay, just do what feels right.”

She got down on her knees and crawled over to me. She began by taking only the head and putting it in her mouth. She ran her tongue all over it which felt amazing.

“I hope I can fit this in my mouth.” She said with a giggle.

Surprisingly, she was able to take about seven inches into her mouth before she started to gag. She kept trying to take more, but couldn’t prevent herself from gagging. I decided to take matters into my own hands. I grabbed the back of her head and forced all nine inches down her throat. I could see she was struggling but she made no effort to stop me. I released her from my cock.

“Wow! Do that again!”

I did as she told and stuck my cock back down her throat. I could feel her moans running up my member, giving a soft vibration that was being felt in my balls. After I pulled out, I got up and motioned Taylor to the chair. I put my head between her legs and began to kiss her pussy lips. I ran my tongue up and down her opening which caused a soft squeal from Taylor. With one quick motion, I rammed my tongue as far up her as I possibly could.

“Holy Shit! Oh God!” She exclaimed.

As I was furiously tongue-fucking her, I let my fingers roam around her ass hole. I slowly began to rub the outside of her hole as my tongue found her clit.

“Stick your finger in my ass baby!”

I did as she said and stuck my middle finger up her ass. She was now have her ass finger-fucked and her clit sucked on…she was in heaven.

“Oh baby…don’t stop, you’re gonna make me cum…oh fuck! I’m cumming…I’m cumming!”

I felt her ass clench around my finger as her juices began to drip down onto my chin. I could tell that she had never had an orgasm like this before. She was violently contracting for a good thirty seconds as the pitch of her moans got higher and higher. I waited for her to relax before I took a condom out of my wallet. She stopped me before I opened it

“You don’t need that, I’m on the pill. I want to feel all of you inside me.”

I put the condom away as Taylor put her knees up on the chair and turned around. I got behind her and started to rub my cock against her wet pussy. She turned her head and smiled as I quickly thrusted into her. I was now fucking her at a rapid pace…so fast that she couldn’t say anything; all she could do was grunt and moan. I had never fucked a girl this hard before but I wanted to make sure that she remembered this for the rest of her life. I reached around her and caressed her breasts and pinched her nipples. For a good five minutes, I kept the pace going as fast as possible but started to slow down since I didn’t want to cum too fast. At the point I started to slow down she cried out, “Oh fuck, I’m cumming again…I’m cumming again”

I pulled out as she squirted her sweet juices down onto the chair, her moans again very loud. She crawled off of the chair and sat on the floor so she could recover from her massive orgasm. I gave her a minute before I picked her up and carried her over to the bed. I placed her on her back and started fucking her again. I reached up and gave her nipples another tweak, which caused another load moan to come out of the 20 year old. I grabbed her by the shoulder and took quick, violent thrusts into her. She could only manage an “oh” between thrusts. I went back to fucking her slowly so I could mover her hair out from in front of her eyes. She was sweating so much that her hair was matted down and very heavy, which made her look hotter than before.

“Your cock feels so good in my pussy” she softly whispered. “Let me get on top, I want to ride it.”

I crawled off of her and lay down as she quickly climbed on top of me. She slowly lowered herself on to my cock, taking me inch-by-inch. She began riding me and moaning again. I was loving the fact that she was a moaner; filling the room with her lovely sounds and making it hard for me not to cum right away. She placed her hands on my chest as she leaned down and kissed me before continuing. Her moans were again getting high pitched and I realized that her third orgasm was quickly approaching. I felt her pussy begin to contract as she lifted herself off of me, moved over to my face and covered me in her cum. I caught most of it in my mouth, but some of it dripped onto my chin. After she came down from her orgasmic high, she bent down and licked the last of her cum off my face. She then whispered in my ear; “I want you to fuck my ass. I’ve never been fucked there before.”

She spit on my cock before laying flat on her stomach. I crawled on top of her, positioned my cock at the opening to her ass and slowly inched my way inside of her. I didn’t want to slam into her like I did her pussy since it was her first time. I eventually got all nine inches inside her as her lovely noises again filled the room. I picked up the pace a little bit as she screamed for me to fuck her harder. I could feel an orgasm building, but I wanted this to last so I didn’t pick up the pace too much. My cock easily slid in and out of her ass as my balls slapped loudly against her cheeks. That added to the already noisy room with her moans still very loud.

“Oh god this feels so good…I never thought anal sex would feel so good.”

It was at this point that I felt my orgasm very close.

“I’m gonna cum…where do you want it?”

“On my face.”

I pulled out and moved over to her head. She used her left hand and started jerking me off. That sent me over the edge as my first thick stream of cum landed directly on her forehead and ran down her face. The second stream left a long white streak on the side of her hair. The next few went around her lips and the last stream shot over her head and landed on her lower back. She sucked the last few drops from my cock before she started to scoop the glops of cum off her face and sucked her fingers clean. I collapsed next to her as she finished cleaning herself. She slid over and rested her head on my chest and softly whispered to me.

“That felt so good…thank you for making me feel amazing. I love you.”

I wrapped my arms around her and whispered, “I love you too”, back to her and quickly fell asleep. She woke me up the next morning as it was time for her to checkout and head home. We kissed and went our separate ways. I thought that it would be the last time I would see her but as I reached into my pocket to find my car keys, I found a paper with a phone number and a message, “Call me on the 26th, I’ll be back here and I want to see you again. Love Taylor!”

To Be Continued (Possibly)…

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