Hazy Night with Taylor Swift Ch. 01

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Taylor Swift's secret is not a secret anymore.
2.7k words
4.48
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139

Part 1 of the 21 part series

Updated 06/08/2023
Created 11/09/2010
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"Hello, you are the 100th caller here at Tacoma's Top Country 100.5. Now for a free date with Taylor Swift you need to name the 5 songs of which the clips were taken from. Are you ready? Go!"

"Number one was Taylor Swift's "Our Song", number two was Kenny Chesney's "Big Star", three was Tim McGraw's "Back When", the fourth one was Danielle Peck's "Bad For Me", and five was Jamey Johnson's "In Color"."

"YOU ARE CORRECT! You have won a free date for two with the lovely Taylor Swift this Saturday at "Pacific Grill" here in Tacoma. Congratulations, what is your name sir?"

"Dan Wilson"

"Well Mr. Dan Wilson, enjoy your free date with Taylor!"

It was Saturday morning as I was psyched for my date with Taylor Swift. I have had a huge crush on Taylor ever since I first saw the video for "Our Song", and have constantly dreamed about just being in the same building as her for a day, let alone a date. I asked for my sister Carly's advice on how I should dress for my date. I didn't want to over-dress but I also did not want to look like a slob.

"I was thinking a dress shirt with my khaki pants, what do you think?" I asked

"Yes on the dress shirt, but you should wear jeans with them instead of those khaki's. That's how I like my men to dress, Taylor might too." Carly responded.

"Yeah, that seems good, not trying too hard, right?" I asked nervously.

Carly gave me hug and told me to calm down. "I've got something that'll calm you down."

She handed me a joint and told me to smoke this before my date if I was still feeling nervous. I can't lie, I smoke a lot of weed and have since I was 15 when I caught Carly smoking in the bathroom and she asked me to join her. After that I would sneak into her room after our parents went to sleep and we would share a joint or her bong. This went on until she moved out shortly after my 19th birthday. I had stopped once I started dating my ex in college, but started again when we broke up last month. I'm now 26 and, knowing how important tonight was, I wanted to be clear in the head.

It was now 2:00 and I was almost ready to leave for the restaurant when my cell phone rang. I looked at the number and didn't recognize it. Usually I don't answer it if I don't know who it is, but something drew me in.

"Hello"

"Hi, is this Dan Wilson?"

"Yes, may I ask who is calling?"

"This is Taylor Swift. I'm calling to make sure you would be at the restaurant on time."

"Absolutely, I wouldn't miss it for the world."

"Awesome, see you then."

"Wait, how did you get my number?

"The radio station, I wanted it in case plans changed. I got to go; my friend is here to drive me to the restaurant"

"Okay, see you in a bit." I hung up.

I grabbed my keys and headed out to my car. I reached into my pocket to put my license in the glove compartment and pulled out the joint. Since I didn't want to be late or leave it in the car, I put it back in my pocket and was on my way. It took my longer than usual to get into town, but luckily I left early enough. It worked out perfect as I met Taylor at the door. We gave each other a hug, followed by me holding open the door for her.

The wait for a table wasn't long, probably because Taylor is a celebrity and we don't get celebrities often in Tacoma, they usually go to Seattle. We sat down at the table and ordered our drinks. We both got a Coke because I didn't drink and she was only 20 and couldn't. While we waited she asked me about my life, what I did for a living, what my interests were, etc.

"I take care of the grass at Qwest Field in Seattle. I cut the grass and paint the lines on the field before event."

"Cool, do you like your job a lot?"

"It's getting me through okay I guess."

The waitress came with our sodas and took our food orders. She got the steak and I got the ribs. I asked her why she volunteered for this "Win a Date with Taylor Swift" promotion.

"Two reasons: the radio station donated $25,000 to the Nashville flood relief, and I haven't dated a regular guy since I became famous. The celebrities I date are all stuck-up douchebags that think they're better than everyone else. You don't seem like that kind of a guy and even if it's only once, it's nice to date a normal person." She finished off with a smile.

Taylor's black purse was sitting on the table when a waiter bumped into it, knocking it to the ground. Both Taylor and I leaned down to pick it up and I had noticed something had fallen out. Taylor saw me pick it up and her face turned red.

"You smoke weed?" I asked

She looked nervous and wouldn't answer me, embarrassed that I found out her secret.

"Taylor?"

"Yes, it's something I started doing after I turned 18. I've been able to keep it a secret, only you and my dealer know what I do. I hope this doesn't upset you."

I reached into my pocket, grabbed Carly's joint and placed it in her hand, and she looked surprised and relieved. She realized that the pot wasn't going to end the date early.

"If you want, you can come back to my place and we can enjoy ourselves with this shit."

Her face lit up with a smile and a nod. Our food came and we both finished it rather quickly because we both wanted to get out of there and have some fun. We both got into my car and started to drive back to my house. Taylor got the joint out and started playing with it, wanting to smoke it so much. We arrived at my house and quickly went inside. I offered Taylor a drink, she declined. We both sat down on the couch and as I was turning on the TV, she leaned in and gave me a kiss.

"That was nice, but why?"

"I've never smoked with anyone before and there is a certain effect the pot gives me that will be awesome for both of us."

I had no idea what she possibly meant by that, until she slowly hiked her dress up and I saw that she wasn't wearing panties.

"This stuff gets my so fucking hot; I always rip my clothes off, get out my "big friend", and fuck myself hard. This will be the first time that I get baked and have a real cock to play with." She lit the joint and took a big drag and slowly let the smoke flow out. She then passed it to me. While I took a drag, she starting rubbing herself, with her dress now hiked up past her hips. I could see that she had a narrow patch of hair above her pussy which was getting more visibly wet. I get really good weed, so it didn't long for us to start flyin'. After the joint was 3/4 of the way gone, she spoke for the first time in a while.

"I've got my pussy out in the open, why don't you take your pants off and let my see what you're bringing to the party."

I looked directly into her eyes and saw the heavy eyelids and bright red blood vessels; she was truly stoned out of her mind. I did what she asked and removed my pants, ejecting my eight inches into the open. Taylor took her last hit and slowly blew the smoke on my cock. She handed me the joint, I took another hit, spread open her pussy lips, and blew right into her. This was definitely a new feeling for her.

"Oh Fuck! Do that again, that was so awesome." She struggled to get that sentence out clearly as the high and pleasure were overtaking her body. I again did as I was told and blew more pot smoke up her pussy. She couldn't contain herself anymore, she swiftly (stupid pun) grabbed my cock and pulled it towards her mouth. She started to suck it like it was a joint, which felt so awesome.

"Damn this is big, I've never had a cock in my mouth before but I sure picked the right one" She said, again slurred. She pulled it out and stared at it for a second.

"I can see it pulsate. That looks like it feels good. Does It?"

"Oh fuck yeah Taylor, keep playing with it"

She started to jerk me off slowly, it was the best feeling I've ever had. She put it back in her mouth and started licking the head like a pro. The marijuana was definitely turning her into a little whore. As she licked my shaft up and down, she took my balls in her left hand and started rubbing them softly, sure not to be too rough (like I would of cared).

"Do you like me playing with your balls?"

"Absolutely baby, don't stop."

She asked me if she could get deep-throated and obviously I wasn't going to say no, so I grabbed her head and forced my cock all the way down her throat. She gagged at first but the second time she was more prepared and held it for over 5 seconds. I pulled out and she quickly took both of my balls in her mouth and sucked on them. I pulled the dress she was wearing over her head and unhooked her white bra, leaving her completely naked except for her boots.

I could feel my orgasm coming soon so I asked her where she wanted me to cum.

"I want you to stick it down my throat and cum baby."

I wasn't about to disappoint her, so I shoved my cock as far down her throat as possible and let my load fall directly into her stomach. I pulled out enough for her to lick the head clean.

We decided to take a break before I start on her. We packed my bong with the weed she had, which in retrospect was a hell of a lot better than my shit. The haze of pot smoke was still lingering from the joint and my small house was about to get even cloudier. We each took five huge hits from the bong. We were both now in a condition where we couldn't talk coherently and, at least for me, I could only feel my heart pounding and my cock still pulsating. I could only imagine what Taylor feels like. She looked up at me with her heavily stoned eyes and asked me a question.

"Since I got you off, can you return the favor? Please?" She said slow and with the sad-little-stoned-girl eyes.

Without answering I took my shirt off and threw it to the ground, leaned down and started to kiss her glistening pussy. The combination of my cock in her mouth and the weed had made her pussy literally dripping wet and I knew this wouldn't take long. Without her expecting it, I quickly shoved my tongue up her pussy which led to a long, slow moan from the country singer.

"Ohhhh shit baby. That feels great." She slurred

As my tongue attacked her hole, my fingers were massaging her clit which made her cry out again.

"FUCK! FUCK! Keep doing that!"

Her pussy was now hot as fire and I knew she couldn't hold on much longer. I switched positions and started licking her clit while finger-fucking her. This sent her over the edge.

"FUCK! I'm cumming! I'm cumming! Oh shit!"

With that my finger became engulfed by her womanly juices. She violently shook from her orgasm and now couldn't even force out a moan. She was so out of it from the pot and the orgasm that she could not make a noise. She grabbed my hand and started licking every bit of her off of my finger.

I gave her no time to recover before I went in to fuck her brains out. She was already lying down on the couch when I got up and knelt on the cushion and started rubbing the head of my cock, now fully erect again as the weed had the same effect on me as it did on Taylor, against the sensitive slit. I was going to take it slow, but with the little strength she had, Taylor said, "Fuck my harder than you've ever fucked before"

Like the rest of the night, I did exactly what she asked and fiercely began to attack that worn-down pussy. I was going so hard; it was numbing my cock even more which felt amazing. Taylor was being rocked so hard, she couldn't talk even if she wanted to. I was still surprised that a seemingly innocent girl like Taylor Swift would not only like to get stoned, but also get fucked like a rag-doll too.

"Damn Taylor, this feels so good. Your pussy is so tight."

"Oh-oh-oh-oh-oh-oh-oh-oh-oh-oh" was all she was able to say. She motioned me to stop for a second because she needed to say something.

"Oh...table...bend me over that table...I want it from behind...Fuck my pussy from behind."

I picked her up off the couch and moved her to the kitchen table. I bent her over and started fucking her as hard as before. I could see her small breasts swing around as I continued to plow her harder. I was starting to feel her pussy contract and I knew she was gonna cum again.

"Shit, Dan. I'm gonna cum again...OH FUCK...FUCK...Ohhhh" she started to tremble at the feeling of her powerful orgasm. I had to hold her as she almost shook herself off the table. I stopped fucking her so she could catch her breath. She sat down on the stool as I climbed on and lied down on the kitchen table. She got up and walked over to my stereo. She found and put in one of her CD's.

"I love getting fucked with my music playing." She smiled, her eyes barely open from the high. She climbed on top of me, gave me a kiss, and started riding me, moaning louder with each thrust. As "You Belong With Me" was playing in the background, she was moving her hips to the music. This was literally a dream come true for me, watching Taylor Swift gyrate to her music while fucking me on a table. I knew this wasn't gonna last much longer, but to my surprise I again felt her pussy contract. She was cumming soon and so was I. She screamed out, lifted up of my cock and showered it in her juices.

"Damn Taylor, you squirt too?"

She smiled as she impaled herself with my cock again and it wasn't long before it was my turn. I asked her where she wanted me to cum.

"I'm on the pill, come inside me baby...Oh Fuck...cum deep in me."

I pumped harder until I couldn't hold it in anymore. I busted my load deep into Taylor's young pussy and filled her up. As I came down from the orgasm, she collapsed into my arms. We passionately kissed for a good twenty minutes, until she had to get up to pee. When she came back she grabbed the bong, filled it again, and we shared more of her weed before we both went off to bed. As I slept, I had a dream that was basically a replay of the night. That dream, like that whole night, will never escape my memory.

I woke up the next morning to find that Taylor had left, but she left a note on the pillow which had her cell phone number and a note that read "Call me Friday, I'm doing a show Saturday in Seattle and I need a place to stay for the weekend. I'm meeting my dealer Maria before I head up there, we will have enough shit to last us the whole weekend. Love Taylor."

To Be Continued...

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8 Comments
TheBigLove126TheBigLove126almost 10 years agoAuthor
Re: Hugs

I appreciate the suggestion but the main storyline of this series is the pot so for this one, the drugs are a necessity.

AnonymousAnonymousalmost 10 years ago
Hugs...

...NOT DRUGS!!!! Good story idea but leave out the drugs mate!!! (Ruined it for me!)

PTBzzzzPTBzzzzover 11 years ago
You should always

write the story the way you want. It IS your story. ***** for the comment

TheBigLove126TheBigLove126over 11 years agoAuthor
Or...

...you could realize that it is a fictional story and I can write it however I want, key word there is "fictional". If I want to write the story the way I did, it's my choice to. If you want to write something that you think is better than go right ahead.

Never in this story did I say it was a recollection of real events. You know why I did not give the relationship a slow burn buildup? Because that would have been boring for me to read and I'm sure writers would agree that you would not write something that you would not read. I wrote it the way I would have liked to read it.

AnonymousAnonymousover 11 years ago
Teenage jerk off fantasy

Everything about this from start to finish is a totally unbelievable jerk off fantasy of a sex deprived teenage boy. I don't know where to start, no bodyguard on a date with a random guy, hugging him when she sees him, going back to his place, then instant sex. I see you continued this series. That's too bad.

Seriously, you could have made this a much better story by building up an attraction much more slowly so that she, being a celebrity, would get more comfortable with a random fan before letting him pound it into her.

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