Hazy Night with Taylor Swift Ch. 02

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Dan gets a surprise when he calls Taylor.
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Part 2 of the 21 part series

Updated 06/08/2023
Created 11/09/2010
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It was Friday morning, almost a full week since my encounter with Taylor Swift. I won a radio contest to get a free date with the 20 year-old singing superstar. As we waited at the restaurant for our food to arrive, a waiter had knocked over her purse allowing a small bag of marijuana to fall out. She was embarrassed until I pulled a joint of my pocket that my sister gave me, which relaxed her. We went back to my house and started to smoke the joint. As we did she pulled her dress up and told me that weed made her horny and this was the first time she has smoked with anyone before. She had kept her use a secret so the paparazzi wouldn't find out. The only people who knew were the two of us and, of course, her dealer Maria. She began to suck my cock once we finished the joint. After she gave me a blowjob, we smoked some more followed by her pussy getting licked clean. We then fucked, smoked some more and drifted to sleep. I woke up and found a note from Taylor with her phone number, informing me that she was going to be in the area for a concert Saturday night and needed a place to stay for the weekend. She also told me that she was going to score a big bag of weed and that we were going to have a good weekend.

I called her Tuesday afternoon to make sure when she was going to arrive.

"Hello"

"Hello, Taylor?"

"Yes."

"Hi, it's Dan. I was wondering if our weekend is still on."

"Of course! I'll be there around 4:00 Friday afternoon, but I won't be alone."

I was confused by this. "What do you mean? Who else is coming?"

"You see, when I was waiting for Maria, my dealer, to arrive and give me my weed I ran into a fellow country star that was waiting for her as well. But I'm not going to tell you who it is; I want you to be surprised!"

"Whoever it is, I'm sure I'll like her. It is a 'her' right?"

"No, it's a big fat guy. Of course it's a 'her'; I wouldn't do that to you." She said with a giggle.

"Cool. You want me to pick you up at the airport?"

"No, I can get a ride. I can't wait to see you again. I got to go now, see ya later Dan"

"Bye."

I hung up and started to wonder just who Taylor was bringing with her, but I didn't think too hard, I like being surprised so I put it out of my mind.

Like I said, it was now Friday morning. I spent the morning cleaning up my house, trying to do anything to pass the time so Taylor and her friend would get her quicker. I was a little on edge since I hadn't smoked since that amazing night. I'm not saying that I didn't have any; I just wanted tonight to be that much better. As I was cleaning, my phone began to ring. I answered it.

"Hello."

"Hey Dan, it's Carly."

"Hey sis, what's up?"

"I never got to ask you how your date with Taylor Swift went."

I didn't know whether or not to tell her exactly what happened, but I thought 'I've talked to Carly about everything since I was 5 and she was 8.' "I'll tell you, and I know you won't tell anybody else, right?"

"Of course I won't tell, Dan. So what happened that's such a secret?"

I told her about everything that happened that night and her only response was, "Damn. How did you get so lucky?"

"I don't know, but it was all like a dream. Thanks for giving me the joint that started the whole thing."

"No problem. Are you ever going to see her again?"

"As a matter of fact, she's bringing one of her country friends and they are spending the weekend here. She has a concert in Seattle tomorrow night and is crashing here. And she's bringing enough weed to last the whole weekend."

"Sounds like you're going to have a hell of a weekend. Have fun, I've got to get back to work."

"Bye."

I looked at the clock and it was 1:00 pm. I knew that in about three hours I would see my lovely Taylor again and get to meet her friend. I decided to take a power nap. I had the same dream I had last Saturday night, the one that was a replay of earlier. I awoke at 3:45 by a knock on my door. I opened up and saw Taylor standing there wearing a raincoat, as the weather had drastically changed since I fell asleep, with a woman behind her. The woman had her hood up and I couldn't see her face. Taylor walked in, removed her coat and gave me a quick kiss on the cheek.

"Hey Dan, I want you to meet my friend." The woman removed her hood, revealing her face.

"Holy shit, Carrie Underwood!" I was shocked to see her. She walked in and gave me a hug.

"I know. I was as surprised as you are." Taylor interjected. "Carrie had kept her secret as well as I did."

"I haven't been doing it long." Carrie explained as she removed her coat. "Last month, a fan gave me a folder filled with drawings he made of me. When I was looking through them, I saw a half smoked joint fall out. I had never tried it before, so when I got home I finished what was left of it and have been hooked ever since."

I was still in disbelief as I had Taylor Swift standing to my side and Carrie Underwood in front of me; two women I hadn't met yet seven days ago.

"When Taylor and I were waiting for Maria, she told me about the time you two had. I could feel my pussy getting wetter as she went further into the story. She invited me over here this weekend and I couldn't say no."

"Before we get started, I'm starving." Taylor said. "How about we order some food before we start having fun?"

I grabbed a menu and order 2 large pizzas, as Taylor and Carrie got themselves comfortable. Carrie was wearing a tight gray tank top with her red bra-straps showing and a very tight pair of jeans. Taylor was wearing a looser white t-shirt and a short yellow skirt. Both women kicked off their shoes and relaxed after a long flight from Nashville. About 30 minutes later, the food arrived and the three of us quickly started eating. While we were eating, Carrie decided to strike up a conversation.

"Have you ever been with two women before Dan?"

I nearly choked from the sudden question. "No, I've only had sex with Taylor and one other girl from high school."

"I guess you'll learn something new tonight then."

With a puzzled look, Taylor chimed in, "Carrie, have you been in a three way before?"

"Back in high school I had sex with my best friend and her boyfriend. That's been my only experience." Carrie responded. "What about you Taylor? Have you done this before?"

"Well, I'm more in the boat with Dan." Taylor added. "I've only fucked three guys in my life." She blushed as she said that.

We finished our pizza rather quickly as we were all ready for what was coming. After we digested a little bit, Taylor reached into her coat pocket and pulled out a big bag of weed. She had enough to probably last a hardcore stoner a good 2-3 months.

"Damn, you went all out! How much did that cost you?" I asked.

"This was about $1,500. I wanted to make sure I had enough for a while. I won't be back in Nashville for a few weeks." Taylor said with a smile. She opened the bag and the smell quickly filled the room. "Go get your bong, I'm ready!"

I got up and retrieved it. Taylor quickly packed it and we started to smoke it. Carrie started first and blew a huge cloud of smoke in my direction. I closed my eyes and took in the aroma. Taylor was next. She took a hit and blew the smoke straight up in the air as I noticed Carrie was starting to play with her own breasts. I could tell that the weed had the same effect on Carrie as it did to Taylor and I; it made her horny as hell. As the bong was passed to me, I saw Taylor reach up her skirt and pull her matching yellow panties, which had a noticeable wet spot on the crotch, off. She handed them to Carrie who held it to her nose and deeply inhaled the scent. I could tell what Taylor wanted; she wanted me to blow the smoke up her pussy again. I took my hit, leaned forward, opened her pussy lips and blew the smoke into it.

"Oh Fuck! I missed that!" Taylor exclaimed.

"Wow Taylor you seemed to like that. What does it feel like?" Carrie asked.

"It feels amazing. Hey Dan, take her pants off and let her see for herself." She took the bong from my hand and took another hit as I moved over to Carrie and unzipped her jeans. Carrie kissed my neck as I struggled to get her jeans off (they were very tight). I finally got them over her shapely hips and dragged them to her ankles. She was wearing a pair of red panties and I could see that there was a wet spot on them, just like Taylor's. I rubbed her pussy through her panties, which caused a light moan to come out. Carrie took another hit as I pulled her panties down to her ankles. I turned around to see that Taylor had completely removed her skirt as both women were now bottomless. Carrie handed me the bong and I took a very big hit and, just like I did to Taylor, and blew the smoke into Carrie's wet cunt.

"OHHHHHHH! Shit that's awesome." Carrie moaned.

"Fuckin' right!" Taylor said as she started to rub herself.

We each took five of six more hits and we were all now completely baked. I looked over to Carrie and saw her heavily bloodshed eyes as she gave me a smile.

"I've never been this high before." Carrie said.

"Hey, Carrie," Taylor spoke. "I want you to take Dan's pants of so you can see how huge his cock is." Carrie quickly unzipped my jeans and pulled them down, exposing my eight inches to her.

"Holy shit! That's the biggest cock I've ever seen!" She said as she grabbed hold of it and started stroking me. Taylor soon joined her so now I was having my dick stroked by these two country superstars who were baked out of their mind. They continued jerking me off as I took my shirt off leaving my totally naked in front of them. Taylor took her hand off my cock and started to pull Carrie's shirt off. Carries soon did the same to Taylor. They both took off their own bras so that all three of us were now completely naked. The women went back to handling my cock. Carrie was the first to let her hands drift down to my balls. As she started to play with them, I reached up and gave Carrie's right boob a squeeze, which led to another moan. I took my other hand and squeezed Taylor's left boob which also led to a moan.

"Your balls feel so big, baby. You like when I play with them?" Carrie whispered in my ear. I turned my head and kissed her passionately, which she took as a yes. The girls switched spots so Taylor was now playing with my balls and Carrie was playing with the tip of my penis. Taylor used her other hand to guide mine from her breast down to her pussy. Not surprising to me, she was dripping wet as I started to rub her lips. Carrie saw this and also led my hand to her cunt. She was also very wet as I rubbed her too.

Both women stared at me with their stoned eyes as they played with my junk. I could see the love in their eyes as they were enjoying every second of this. Taylor looked up and gave me a kiss before lowering her head and taking my balls in her mouth. The warm feeling on my balls felt so good. Not to be outdone, Carrie knelt down on the floor and took all eight inches in her mouth. She began to lick the hole of my cock, almost like she was trying to fit her tongue in. This was the greatest feeling I've ever felt.

Taylor began to start sucking one ball at a time as Carrie began to suck my cock faster. My hand was now running through Carrie's long blonde hair, as my other one was still rubbing Taylor's cunt. I moved my hand and started rubbing her asshole.

"Ooo, that feels good baby." Taylor whispered.

Carrie looked up to see what I was doing. She stood up and walked over behind Taylor and sat down. She stuck her middle finger out and impaled the young woman's tight pussy.

"OH MY GOD! Fuck yes!" Taylor screamed as she let my balls fall out of her mouth. Carrie was roughly fingering her as her cries of lust continued.

"Please don't stop Carrie! That feels so fucking good! Oh shit!"

I decided to join in and stuck my middle finger up Taylor's ass. Carrie and I were penetrating this young woman hard and in a rhythmic pace.

"Fuck! Fuck! Fuck! Oh! Shit!" Taylor could barely say anything else, the weed and our fingers were taking the young singer over. We switched places as I took her pussy and Carrie shoved her finger deep in her tight ass. As we were fucking her, Carrie and I began to make out and run our free hand through each other's hair. Taylor's moans were getting higher and higher pitched as she was in pure bliss. Carrie and I each took one of her breasts and started tweaking her nipples. Taylor was in a special place and couldn't make a sound as she started to suck my cock.

The young Taylor Swift now had a hand on each of her breasts, my middle finger in her pussy, Carrie Underwood's middle finger in her ass and my cock in her mouth. I wondered how much longer she would hold on.

"You're such a little whore Tay." Carrie said with a laugh.

We had been violating Taylor's body for about 25 minutes before the inevitable happened. She pulled my cock out of her mouth and screamed, "Oh fuck I'm gonna cum! I'm gonna cum!" Carrie got down and put her face between Taylor's legs as I continued to finger her pussy. I pulled out and started rubbing her clit which pushed her over the edge. She squirted her juices all over Carries face as she began to shake. I leaned over and kissed Taylor as she continued to cover Carrie's face. After about 30 seconds, the cum stopped pouring out of her as she collapsed on the couch with her head on my lap. Carrie licked every inch of her pussy so there was nothing left. She sat up as the juices started to drip from her chin. She scooped some off with her finger and put it in Taylor's mouth. Taylor furiously sucked her fingers clean, loving her own taste. I moved in and licked every inch of Carrie's lovely face and kissed Taylor, again giving her a taste. Taylor got up and moved to the other chair and relaxed.

Carrie and I were now the only two on the sofa until I got down to the floor and started to attack her pussy with my tongue. She was soaking wet from pleasuring Taylor and she tasted a little sweeter. I stuck my tongue as far up her cunt as I possibly could as she screamed aloud.

"Oh shit Danny! Your tongue feels so good! I haven't been tongued like this in a long time. Oh!" She was enjoying herself a lot as I continued to punish her pussy. I reached up and gave her nipples a quick twist which only made Carrie cry louder.

"Fuck! You are so good! You make me so hot!" Hearing this made me just want to throw her down and fuck her brains out, but it was only 6:30 and I had no plans to stop anytime soon. I began to massage her clit with my other hand as I felt a hand grab my cock from behind. Taylor was recovered and ready to suck my cock again. She lay down on the ground and started sucking me hard. I moaned from this feeling which vibrated its way up Carrie's burning pussy. She was literally dripping wet as a stream of her sweet nectar dripped down her thigh.

Carrie lifted her foot up and started rubbing Taylor's breast with it. I could tell that Carrie couldn't hold on as her screams got faster and faster as her orgasm was building. She grabbed my head and pulled it closer as she began to violently shake, with her moans slowing down and becoming more sensual. Her cum filled my mouth as she was holding me so close, it felt like he was trying to shove my entire head up her. Her orgasm was a long one just like Taylor's was. I could feel myself starting to succumb to Taylor's blowjob. I got up and motioned Taylor over to the couch. I stood up on the couch and got my cock up to both girls' faces and told them to open up. They did as I shot my thick cum down both girls' throats. One shot missed and got in Carrie's hair, but she was too stoned and horny to care. Both women licked the rest of my cock clean and then kissed, swapping the cum between their tongues.

I sat between them, neither of us really able to move or say much. In the last thirty minutes, all three of us had the best orgasms of our lives. We remained motionless, over than heavy breathing, for a good 25 minutes until Carrie got up to get Taylor's bag of weed, scissors and rolling papers. She sat at the table and started rolling a joint as Taylor wrapped her arms around me and kissed my neck. Taylor looked over and saw my cum in Carrie's hair.

"Carrie, you got some of Dan in your hair." Carrie licked her fingers and wiped my cum out from her hair. She then sucked on her fingers and flashed a smile to Taylor and me. She looked very hot at this point as her hair was matted down a bit from Taylor's orgasm. As Carrie continued, Taylor whispered in my ear.

"How do you like my surprise, baby?" I smiled and planted a kiss on her lips.

"I love you, Taylor." I said which put a big smile on her face.

"I love you too, Dan." We kissed again. "And I think we both love Carrie." I smiled as I heard Carrie giggle, having clearly heard our conversation. She got up and brought the fat joint over and turned to stereo on. The CD Taylor put in there last week was still in there, but Carrie took it out and put my "Favorite Songs" CD in. Carrie smiled as her song "Undo It" was the first one to play.

"Your favorite song is one of mine, I love you!" She sat down and kissed me. She lit the joint as the room again filled with my favorite scent. She passed it to Taylor who took a hit and blew it in my mouth. I then blew that in Carrie's mouth, who then blew it back in Taylor who put her head back and blew it straight up. The song was half over and I noticed Taylor was mouthing the words and swaying back and forth. She was so lost in the song that she didn't notice me handing her the joint, so I put up to her lips as she inhaled. We put the joint out with about half left and relaxed. Taylor's song "Fearless" began to play which caused Taylor to get up and turn the volume up higher. Instead of sitting down she started dancing to her song, still totally naked. I looked over and saw Carrie fingering herself while watching the naked, stoned 20 year-old woman dance wildly.

I grabbed my cock and joined Carrie. We both sat there, getting off to Taylor's dancing. When the song ended, I got up and moved towards Taylor. I moved her to the couch, bent her over so that her face met Carrie's, and put my cock up to her opening. The two women started to passionately kiss as I slowly inched into Taylor's cunt. I could hear her moan into Carrie's mouth as my whole cock was now inside her. I began to slowly hump her as she continued to make out with Carrie. I noticed that Carrie was starting to moan. I looked down and saw Taylor's index and middle finger fucking Carrie at the same pace that I was fucking her.

I started to fuck Taylor harder, which made her fuck Carrie harder. The house was filled with thick smoke which made for an amazing smell combination of the weed and dripping pussy. Taylor was as wet as she was when I was fingering her. I could only imagine how wet Carrie was feeling right now. I was now thinking of Carrie's pussy while I fucked Taylor's, which made me even harder (which I didn't think was possible). After a few minutes, I whispered in Taylor's ear, "Have you ever had a cock in your ass?"

"No, but I want one!" After she said that, I pulled out and positioned my cock at her tight anal opening. "Be gentile." She whispered.

I slowly inched my cock into her asshole. She clearly wasn't prepared as she screamed for me to stop.

"I'm sorry, did I hurt you?"

"No, I'm just getting used to it. Ignore me when I tell you to stop." She prepared herself for more of me. Carrie tried to calm Taylor down.

"Look at me baby. Don't worry, I've been fucked in the ass plenty of times. Just let it happen. Okay, baby girl." Carrie said as she kissed her. I pushed further in as Taylor again began to scream. Carrie lunged forward and roughly kissed Taylor to muffle her cries. I was now fully inside Taylor as I began to slowly fuck her. She was still crying in Carrie's mouth, but soon her cries of pain turned into cries of joy.

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