Hazy Night with Taylor Swift

"Damn, I'm going to miss this place," I said out loud as I packed the last thing into my suitcase, the giant bag of weed that Carrie had prepared.

I was waiting for my ride to arrive. Taylor told me through a brief video chat on Monday that she would be sending a friend to pick me up and drive me to the private hangar at the airport. I had no clue who the friend was but based on every experience I had with the tall blonde, I figured that my next sexual adventure was mere minutes away.

I relaxed on the couch, running the weekend back in my head once more. After the last bit of sex, Carrie and Bridgit took a quick shower together. I was too blinded with bliss that I could not drag myself out of bed to watch or join them. They came back in the bedroom and slowly dressed in front of me before it was time to leave. We shared a big group hug and a big group kiss before the ladies left to resume their lives while I looked over the house, sampling from the garden regularly.

I was about to light a bowl when I heard a knock on the door. I checked my phone, checking to see if the friend had texted me like I had assumed she would, finding nothing. I got up and answered the door, seeing a very tall blonde, taller than Taylor by at least three inches, standing there.

"Hello," I said, looking the woman in her green eyes.

The woman smiled at me, extending a hand. Had I known that Taylor did not have a sister, I would have sworn that this was her. Dressed in a tight, black long-sleeved shirt and even tighter jeans, the woman was a spitting image of my favorite girl.

"Hi, I'm Karlie," she said as I shook her hand. "You must be Taylor's special friend."

"I guess I am," I responded, offering her the bowl that was still in my other hand.

Karlie took the bowl and took a long hit before handing it back to me.

"One is enough for me, we need to get going," she said, blowing smoke out the door. "Taylor and Sydney are waiting for you."

"Will you be joining us?" I asked, taking an equally long hit form the bowl.

"Unfortunately no, I have work to do in the city tonight," she replied. "I wish I could though, Taylor's plane rides are a blast."

I grabbed my bag and followed the model out of Carrie and Bridgit's home, officially putting the best weekend ever in the past. I could not help but stare at Karlie's ass as we walked to the car. The tight jeans she wore, wedged tightly up her ass-crack, left nothing to the imagination. She looked over her shoulder, catching me staring.

"Enjoying the view?" she asked, laughing.

"Oh, sorry," I said. "But yes, yes I am."

"I should tell you that I'm a lesbian," she said, making me both slightly sad and greatly intrigued. "I know what you usually do with Taylor's friends, I get the details regularly. No offense but I'm just not into dudes."

"It's okay," I said, slightly disappointed. "I know Taylor can fuck for two."

"Wow, I expected you to be mad," she said, getting in the car. "Get in."

I joined Karlie in the car before we took off for the airport. As we sat in a bit of morning rush-hour traffic, I felt the beautiful model's hand grab onto mine. I looked over at her, seeing her staring forward with no emotion on her face. Slowly, my hand was pulled closer to her until my palm was resting against the crotch of her jeans.

"I thought you were-," I started before she stopped me.

Karlie shushed me while starting to move my hand up and down against her.

"That pot you had was mind-blowing," she said with a grin on her face. "If you stay quiet, I'll just pretend that you're a butchy girl with sausage-fingers

Karlie closed her eyes and took a deep breath while unzipping her jeans. She let go of my hand for a second to roll the tight denim off her hips and halfway down her thigh, exposing her lack of underwear. I could already sense she was not wearing anything underneath her clothes, seeing her nipples harden through her shirt earlier in the crisp morning air.

Taylor's look-alike once again grabbed my hand and pulled it towards her crotch as the traffic started to clear a bit. As my palm rested on her unshaven pubic hair, she pushed my middle finger past her lips and into her cunt. Seconds later, my index finger was pushed in as well, needing some effort to get inside. I could tell that nothing too large had entered her before since she was as tight as a vise.

"Just do your thing," Karlie said, still not looking at me.

I started to wiggle my fingers around inside of the slender woman's increasingly dampening pussy. I could see the muscles in her hands grip the steering wheel with increased intensity by the second. The more I moved my fingers, the tighter she held on. I looked at her eyes, seeing them squint until they were nearly shut. I started to wonder how she could possibly drive with what I was doing to her, mixed with what she had smoked not too long before.

Karlie jumped when my thumb pressed against her sweating clit. As I started to circle around it, her butt lifted off the leather car-seat and hovered an inch or so over it. I could hear the blonde's breathing pattern speed up while her pungent sex juices started to drip onto the seat. I pulled my fingers out a bit before slamming them back in as hard as I could, causing her to release an adorable moan.

"Fuck," she grunted.

As my fingers started to fuck her harder, Karlie's body reacted naturally and started to thrust forward and back against them. She kept her eyes forward, never looking at me and probably still imagining me as a big-fingered woman. My wrist was starting to get sore while her pussy was becoming a pond. I knew that there was no way that the lesbian could hold back from cumming around this man's busy hand. Karlie suddenly pulled over the car on the shoulder and let out an earth-shattering scream.

"FUCK!" she yelled as her pussy contracted around my two tired fingers.

Karlie's body froze as her vaginal muscles tugged at my finger's, trying to milk them as if they were a cock. She closed her stoned eyes and rested her forehead against the steering wheel, panting and gasping for air. She let me continue to tickle her twat for nearly a minute before she pulled my hand from it and pushed it away.

"I can see, why Taylor, likes you," she stammered, lifting her head up to take a deep breath. "That's the first time a guy has gotten me off since I was in high school."

"Glad I could help," I said while licking the model's cum off my fingers.

Karlie gave me a smirk before pulling the car back on the road, continuing our trek to the airport. The lovely blonde never made any attempt pull her jeans back up, keeping her soaking-wet slit on full display. I could not help but stare at the wet hair sitting right above her relaxing entrance.

We arrived at the airport, albeit a little later than Karlie had thought. I believe that when she picked me up from the house, she had no intention of having an orgasm at my hand. She pulled her jeans up before pulling up to the guard's station. She showed the guard her identification and he allowed us through. We made our way to the private hangar, where Taylor's jet was parked. After waiting for about two minutes, I saw a woman walking towards the car in the side mirror. The long blonde hair, slender legs and glowing face of the woman made my heart skip a beat.

Taylor walked up to the driver's side window, popping her head in to give Karlie a long, sexy kiss. Throughout the entire kiss, her big blue eyes were wide open, staring directly at me while her pushed-up cleavage was in clear view. She had on a sleeveless white hoodie, unzipped enough to show her low-cut black tank top, low enough to see the edge of her emerald-green bra.

"I missed you," she told Karlie, breaking the kiss. "And you too, baby," she said, her eyes shifting towards me.

"I really missed you," I said as I exited the car.

I ran around the front of the car and met her in an embrace, first hugging her before meeting her lips with mine. Taylor placed her hands on the back of my head and pulled me as close as she could, her tongue sliding past my teeth and towards the back of my throat. My hands fell to her ass, which was already being held tight by a pair of shorts that looked a size too small. I lifted her up, her legs wrapping around my body as she put all her weight into the kiss. I backed up to the hood of the car to prevent falling over.

"You never kiss me like that," Karlie joked, poking her head out the window.

Taylor ignored the giggling model, continuing to swirl her tongue around deep in my mouth. After nearly a minute, my favorite lady slowly pulled away and stared deeply into my stoned eyes. We shared a few pecks on the lips before she dropped off me and adjusted her shirt, which was halfway up her body.

"Miss me?' she asked, wiping saliva off her lower lip. "Never mind, I can see that lump in your jeans."

I made no effort to hide the hard erection that resided in my pants. The time we had spent apart only made the stunner more attractive, which was something I did not see as possible. Taylor went back to the driver's side window and shared another quick kiss with Karlie while I grabbed my bag out from the back. Soon after, the model put the car in drive and headed away.

"She's so sweet for picking you up," Taylor said, wrapping her arms around my neck again. "I know you probably would have liked someone to fuck but she was the only one I could get."

"It's okay," I said, putting my hands on her hips. "She let me play with her pussy."

"Wow, really?" Taylor asked in surprise. "Karlie doesn't like men at all."

"She smoked the Undlerweed and pretended that I was just a manly woman," I said with a laugh.

Taylor giggled before giving me another quick kiss. She grabbed onto my hand and strolled me over to the jet. After walking up the steps and onto the plane, I overheard Taylor give the pilot their instructions.

"Let's get going, Los Angeles awaits," she said.

"I thought you were taking me home," I said, confused as to why the plane was going to Los Angeles.

"Do you not remember?" Taylor asked. "When we talked on Sunday, I said that your sister and Lucy wanted you to come over. You agreed to do it. I guess you smoked a little too much?"

"I completely forgot," I told her, looking embarrassed. "I mean, I won't complain, I haven't seen either of them in ages. Will you be joining us?"

"Wow, you really don't remember our chat," she said, lightly smacking my chest. "Sydney and I are heading to Hawaii for a concert, we're just dropping you off. You need to learn to listen, you bad boy."

Taylor dragged me by the shirt to my seat, a huge smile on her face the entire time. She sat me down next to Sydney, who was fast asleep under a fluffy pink blanket. The young woman looked even more attractive in person as she peacefully napped.

"Sydney," Taylor said, lightly tapping her shoulder. "Wake up, Syd."

Sydney slowly opened her big, blue eyes and looked directly at me. A smile came to her face as she stretched her arms over her head.

"Hey, you," she said, pulling the blanket off herself, revealing the black hoodie, short pair of denim shorts and knee-high leather boots that covered her petite body.

"Hi Sydney," I said, leaning over and giving her a long hug.

After our embrace ended, Taylor sat down next to me, fastening her seatbelt. The plane started to back up and prepare for take-off.

"Did you bring any of Carrie's stash?" Taylor asked me.

I reached into my pocket and pulled out a fat joint that I had rolled before I left. Taylor was giddy as she took it from my hand, putting it between her lips. I pulled out my lighter and lit the joint for her. She took a slow, intense inhale, sucking in as much smoke as her lungs could hold. Sydney and I watched as she let the smoke roll from her mouth and nose in a slow, fluffy cloud. She coughed a bit before passing the joint to me.

"You go," I said, I handing it to Sydney.

Sydney mirrored Taylor, sucking in and blowing out the smoke very slowly. She took a second puff before it was my turn. I took a quick hit so that Sydney and I could blast Taylor's face with a double-shot of smoke. The blonde closed her eyes, holding her nose up high and taking in the scent of the pungent pot.

By the time the plane was steady in the air, the joint was more than half gone and the three of us were plenty high. I looked at Taylor, seeing her glassy pink eyes staring at my face. Turning my head, I saw Sydney, whose heavy red eyes were staring but much further south than my face. I had not realized how rock hard my cock had become.

"Nice boner," Sydney said, resting her hand on my leg.

Without saying a word, Taylor grabbed hold of my pants, roughly pulling them down and releasing my erection from its chamber. Sydney covered her mouth, trying to hide the surprised look on her young face.

"That's a lot bigger in person," she said, her eyes not looking away.

While I paid attention to Sydney, Taylor wiggled herself out of her sleeveless hoodie and was starting to pull her shirt off. Now just in a pair of shorts and a green bra, she stood up and walked over to her young friend. She pulled the hoodie off Sydney's body, showing me her bare breasts. Seeing the twenty-year-old's smooth, perky breasts almost caused my dick to erupt on its own.

"Take your shorts off but keep those stripper boots on," Taylor commanded of her friend.

With no hesitation, Sydney peeled the tight denim shorts from her hips, down her legs and onto the floor. Since she had not been wearing a bra, I was not shocked at all to see her bald, pink pussy uncovered by underwear. She started to reach for my cock when Taylor grabbed her wrist.

"No," Taylor said, bringing Sydney's hand to her own chest. "Take my bra off for me."

Sydney stood up, slowly reaching her hands behind Taylor's back. They locked eyes as they embraced, sharing a peck on the lips before the bra became unhooked. The younger girl pulled it off, leaving Taylor in nothing but a pair of black shorts.

"Still perfect," I said, quickly stripping myself of all clothing.

"You're too much," Taylor said as she slowly dropped to her knees. "I think I know what you want."

"Can I help?" Sydney asked as she stood next to us, her little right index-finger sliding towards her clit.

"Not yet, just sit down and let the professional show you how it's done," the blonde said, wrapping her hand around my throbbing shaft.

Taylor immediately put her lips to the head and pushed forward, filling her mouth by taking me as deep as she could. Within a second, her nose was pushing hard into my pelvis while by balls were firmly pressed to her chin. She pointed her big blue eyes at me and slowly pulled back until only the head rested between her tight lips. Slowly, her tongue swirled around the hole on my cock, sending shivers up and down my relaxed body.

"You haven't lost a step," I said, cupping Taylor's head in my hand while she smiled at me.

My eyes shifted over to see Sydney pleasuring herself, two fingers going in and out of her pussy as deep as they could go. Her eyes were laser-focused on Taylor, trying to learn what the older woman wanted her to learn. The younger singer's face was beat red, almost matching her stoned eyes, as she stabbed at her cunt with her hand.

Taylor rested the side of her face on my knee, slapping her lips with my engorged cock while her tongue quickly slid out. I reached out to grab her head with both hands, pulling her closer and taking control. It had been so long since I had seen her and while I loved her teasing, I was not up for it right now. I wanted to fuck her badly and her mouth was in the right place at the right time.

"I need to cum down your throat," I told her as I used her head like an inanimate sex toy.

"Do it," I heard Sydney whisper. "Fuck her. Yes, fuck her good."

I was almost certain that Sydney thought we could not hear her as her eyes continued to stay focused on Taylor. Not wanting to disappoint the young woman, I kept my pace as fast as I could without hurting my true love. The blonde's eyes were wide open despite the heaviness of the Undlerweed dominating her brain, a mixture of concern and joy in them. She was not expecting such a rough fucking but she was loving it. She would do anything for me just as I would her.

Any tenseness in Taylor's body that was gained from the sudden skull-fuck was gone now. The only thing keeping her from melting to the floor was the grip I had on her blonde hair. I could feel the seed begin to mix inside me. One last look at Sydney was all I needed to help me boil over.

The lights in the plane were glistening off the juices that gushed from Sydney's sweet slit. Her hands darting inside and out of her body was making an audible splashing sound that I could hear over Taylor's sultry gags. Suddenly, the young woman lifted herself up on her seat, sliding her feet underneath her body into a squat. Her left hand tightly gripped the arm rest while her right aided her to a massive orgasm. Juices rained down on the soft red seat below, leaving dark red stains in its landing. I could hear the entire seat rattle as her extremities shook violently while trying to keep her steady. She kicked her feet out, letting her bare ass plop down on the seat, her arms dangling over the side, her right hand dripping while her damp legs rested on the floor of the aircraft.

It was amazing that I did not choke Taylor with a massive load of cum while we watched on but once it as done, so was I. After nodding at Taylor, I let my guard down and kept from holding back. She closed her eyes and waited for a second or two before I shot load after load of my salty, sticky seed against the back of her throat before it slithered down into her stomach. She let out a deep moan as she took the feeding she had been waiting on for a long time. As soon as I was done, I let go of Taylor and she rested her head on my knee again, looking up at me with a look of pure bliss on her face.

"I love you," she said, picking a pubic hair from between her two front teeth.

"I love you too," I replied.

"Can I join in now?" Sydney asked from her seat, her fingers tickling at her pussy once more.

"Well he can't go right now," Taylor said as she pulled herself to her feet. "So, if you want to join, you had better be thirsty for cunt."

Taylor turned her back to me and looked at Sydney. I sat forward and grabbed onto the waist of her black shorts. I could see Sydney's smile grow as I pulled them down, showing off the lack of underwear Taylor was sporting. She quickly turned around to show me the little patch of dirty-blonde hair that sat above her throbbing red clitoris.

"Can you get my pussy high before she drinks up?" Taylor asked as she twirled the half-joint in her fingers.

I took the joint, Taylor lighting it, and took a deep hit. My blonde lover took the joint from me to allow me to work my magic. I turned her to allow Sydney to see before I spread her wet lips wide apart and softly blew the hot smoke in her waiting cunt.

"Oh, fucking hell," Taylor moaned while taking a hit from the joint. "Mmm."

Sydney slowly slid out of her seat and crawled over to us. I was not sure if she was doing it to be sexy or if she was so worn out from her orgasm that crawling was her only option. She held her hand up, asking for the joint. I continued to hold Taylor's pussy open as the 'Echosmith' singer took a very long hit, very slow hit. She struggled not to immediately cough but held it in long enough to finish the size of the hit she had hoped for.

"Get my cunt nice and baked," Taylor whispered.

Sydney closed her eyes and blew a steady stream of smoke directly up the tight entrance of Taylor Swift. The woman had a lot more lung capacity than I did, so she gave Taylor a longer blow than I ever could.