tagCelebrities & Fan FictionBackstage with Taylor Swift Ch. 05

Backstage with Taylor Swift Ch. 05


Kellie Pickler stopped, her bra half-way on, as Taylor's suggestion hung in the room. Taylor Swift, an 18-year-old Country singing star, had asked one of her close friends, 21-year-old Kellie Pickler, also a Country star, to come back to the hotel with Taylor and me.

For me, it had started bringing my poor cock back to life. But then, who am I to be involved with these beautiful Country singers?

It all started after Taylor's 18th birthday. I had backstage passes, and went back to congratulate the girl on her performance. I entered her dressing room to find her half-naked and masturbating. We had made love then and there.

Then a group of Country musicians entered Taylor's dressing room, catching the two of us after the act. It was a group called the Country Musicians' Orgy, or CMO, and Taylor was to be inducted that night. I was allowed to remain, and participated in a great sex party.

A couple months later, Taylor came back to me. She was supposed to induct Bucky Covington into the CMO. The inductee and the previous inductee were supposed to open the orgy with a twosome sex show. Taylor had been inducted by Carrie Underwood. Now it was Taylor's turn.

I gave Taylor some suggestions, and she had spent the night with me. Before leaving, she made sure I would be at this evening's CMO.

Today had started with a flight from my hometown to Dallas, Texas, where the CMO was to be held. Taylor had accompanied me on the flight, and we had joined the Mile-High Club. Upon getting into the limousine for the ride from the airport to the hotel, I had licked Taylor, but denied her orgasm twice.

When we were finally alone in our room, Taylor and I had made love for over an hour, giving the girl all the orgasms she had needed. After resting a bit, we headed to the arena. After the show, we gathered for the CMO. That was when Taylor had seen Kellie, and the two friends spent most of the orgy together. I was with Taylor also, so she felt comfortable in the sex setting.

As we were dressing after the orgy, Taylor had made the suggestion to her friend. She smiled at Kellie, and Kellie, a North Carolina native, smiled back.

"Sounds great, Tee," Kellie said, her accent very thick. "But Ah need to stop at muh hotel and get a few things first."

"No problem," Taylor replied. "We can all ride in my limo, stop at your hotel, then back to our room." Taylor nodded in my direction, making sure Kellie knew I was indeed part of the "our" in her words "our room."

We finished dressing rapidly. Despite the speed, Taylor took the time to put her dress back on. She had abandoned it shortly before the CMO started, a necessary step in her successful seduction of Bucky Covington.

While Taylor and I were in the penthouse suite of the Crowne Plaza hotel near the airport, Kellie had selected the Hyatt Regency near the arena. The limo driver took us to the Hyatt first, and Kellie said, "Come on up. You should see what I'm going to bring with me to your hotel."

Taylor and I were intrigued. The three of us entered the hotel, crossed the lobby, walked to the bank of elevators and rose in near-silence to Kellie's 12th-floor hotel room.

We entered the room and Taylor and I froze in our tracks. On the one bed, lounging naked, was Carrie Underwood!!

I was stunned, to say the least. Sure, I had seen 24-year-old Carrie naked before. She was the Opening Act with Taylor during the first CMO orgy. She inducted Taylor, introducing the 18-year-old to lesbian sex at the same time. But I had never thought to see her this way again.

Taylor snapped out of the trance first. Rushing over to the couch screaming "Caaaaaaaaaarrrrrrrrrrrrrrrriiiiiiiiiiieeeeeeeeeeee!!," the young woman jumped the Idol winner. kissing her and rolling with her off the bed and on to the floor in her exuberance.

Kellie giggled, watching her two friends hug and kiss. I have to admit that it got to me as well. My cock stiffened some more.

When the two came up for air, Kellie explained what was going on. "You remember Ah mentioned Ah inducted Carrie inter the CMO," she said. "Well, when she told me she had inducted you, Tee, Ah about wet my pants. So Ah arranged to be at tonight's CMO. Carrie was busy performing in Houston tonight, but we had planned to meet here after the CMO.

"Muh job was to try and git you over here. Ah didn't know you'd bring" and Kellie said my name "along with you tonight, nor that you'd invite me to your hotel. Ah figger it's bigger than this room, and if we's gonna to be a foursome, we can use the extra room."

"So we're going with Tee?" Carrie said.

"Seems that way, Carrie," Taylor said. "Unless you want to stay here alone tonight," she added with a sly lilt in her voice.

"No chance," Carrie replied. "Just give me a minute to get dressed."

Soon the four of us were in the limo heading to the Crowne Plaza. The girls were recapping the evening's CMO. Kellie in particular was in awe of the opening act Taylor had put on. Taylor, for her part, gave me credit for the idea, and also told them about the strip club we had gone to where she had purchased her clothes.

"I want to see that act," Carrie said. "Do you think" and she said my name "would mind playing Bucky so I can see?"

"Not at all," I told the girls. "I've done it before, when Taylor practiced."

The threesome then caught up on their lives. They were still laughing about the pathetic attempt Taylor's almost-boyfriend, Drew, had made to get back with Taylor. It was this Drew and Taylor's then-love for him that inspired her to right her first hit record, "Teardrops on My Guitar."

After hearing of Taylor's love for him, Drew had tracked Taylor down to her home in Nashville, Tenn. He had called and called her, but Taylor never returned his call. Then one day, as Taylor was about to leave to pick up Carrie and Kellie for a night at the movies, Drew drove up and blocked Taylor's car in her driveway. He apologized for ignoring her back then, and wanted a chance to show her his love now.

Taylor wisely refused. She had moved on. That she had moved on with me was not brought up. Drew finally left, a broken shell of a boy. The next day, Taylor filed a restraining order on him, to keep him away from her.

When the limo pulled up to the lobby doors of the Crowne Plaza, it was almost 1 in the morning. Despite the lateness of the hour (early morning??) the lobby was nearly full. A massive hush fell over the room when we entered.

I had Taylor Swift on one arm and Carrie Underwood on the other. Taylor had Kellie Pickler on her other arm. The four of us walked arm-in-arm through the lobby to the front desk. "Send some champagne to the Penthouse," I ordered.

"Yes sir. Right away sir," the desk clerk said. We then crossed to the elevator. As we entered the elevator, I saw the desk clerk give me a quick Thumbs-Up signal. I smiled brightly as the elevator doors closed.


As soon as the door to our Penthouse was closed, Taylor went into the bedroom, only to emerge a minute later. I knew she had removed her dress, since she was going to demonstrate her opening act to Carrie Underwood. The three girls toured the Penthouse while I answered the doorbell. A steward entered with the champagne. I signed for it, then sent him on his way. He kept straining his neck, trying to catch a glimpse of the three women I had in the room. As I was ushering him out, I saw his eyes bug out, and he started back into the suite. I got him out, locked the door and bolted it.

I turned around to see Carrie, naked, slip into the main bedroom. I grabbed the champagne and entered the room myself. Then it was my turn to have my eyes bug out.

Carrie was already lying on the bed, her legs spread wide. Taylor, her trench coat flopped over a chair, was half-on and half-off the bed. licking deeply at Carrie's wide-open pussy. Kellie, also down to her underwear, was on her hands and knees on the floor, pulling the string on Taylor's leather thong aside and licking gently at her pussy and ass hole.

That did it. My cock rose to full erection. I crawled behind Kellie Pickler and felt her pussy through the bikini panties she wore. It was very wet. I slid my clothes off my body. I took Kellie's panties down off her hips and slid them to the floor. I moved forward and plunged my cock deep into her wet pussy.

Kellie moaned in excitement feeling me fucking her. Her excitement flowed through her lips into Taylor, and, it seemed, from Taylor into Carrie. Carrie lifted her hips high and came, drenching Taylor's mouth. Taylor in turn came, giving Kellie a mouthful of pussy juice. After a few strokes from my cock, Kellie came, screaming her orgasmic lust into Taylor's pussy.

Carrie seemed to be in charge. She sat up and quickly stripped off Taylor's bra, ignoring her own interest in the Opening Act reenactment. I reached along Kellie's back and undid her bra, letting it fall off her shoulders. Her breasts swayed as I continued to steadily fuck the 21-year-old.

Carrie got off the bed, grabbed my hand with her left hand and Kellie's with her right, and pulled us both on to the bed. I had to slide out of Kellie's pussy to make this maneuver, but I remained hard.

When I got on the bed, Taylor, now wearing only garter and stockings (the only clothes left on any of us), bent down and started sucking on my cock, licking it clean. Kellie came up alongside her, and the two women took turns sucking my cock. First Taylor would deep-throat me, then Kellie would suck me as deep as she could. After a few rotations, both girls got on either side of my shaft and licked from bottom to top, kissing each other around the shaft.

Carrie, meanwhile, leaned over me and fed me her breasts. I hadn't noticed during the first CMO how soft and sensitive the American Idol winner's nipples were. Maybe it was her previous orgasm, but as I licked and suckled her nipples, Carrie throatily said "Bite them." Following instructions, I bit the nipples, and Carrie Underwood came, her body shaking with its orgasmic intensity.

Kellie saw Carrie's orgasm, and slid her mouth to Carrie's pussy, while I continued sucking her nipples. Taylor got off the bed, only to return a minute later with one of the toys from my overnight bag.

Knowing in advance I would be with Taylor Swift after the orgy, and doubting I could get an erection after the CMO (a doubt I was currently disproving), I had packed a bag with some of my favorite toys. I had brought a couple of dildos, a couple vibrators, a strap-on and (high hopes had I) a double-headed dildo.

Taylor had the larger vibrator. Ten inches long, 1 1/2 inches in diameter and with five speeds, this was a monster vib. The girl shoved it into Kellie's pussy and turned in on "High."

This larger-than-king-size bed actually shook with Kellie's immediate orgasm. Monster Vib had done its job again, and again, as Kellie had a second orgasm right on top of the first.

Taylor took Monster Vib from Kellie's pussy and shoved it in to Carrie. The older singer smiled and said "That feels GOOD!!" Taylor started it vibrating at 3, then moved it to 4 before getting to 5 a minute later.

I could feel Carrie's body vibrating in time with Monster Vib. I had not noticed Kellie leave the bed, but when I heard Taylor gasp in amazement, I released Carrie's breasts looked at the 18-year-old.

Kellie had the double-headed dildo inserted in Taylor's pussy. She was moving it in and out, matching Taylor's movements with Monster Vib into Carrie.

I slid over near Kellie and whispered into her ear, "That has two heads. Want help mounting it?"

Kellie's eyes clouded over in lustful appreciation. She nodded. I took her by the shoulders and helped her scoot into position. Holding Kellie upright with one arm, I took the other hand and put it on the double-header. I slipped the second head against Kellie's pussy lips. The 21-year-old inhaled, and I shoved her body onto the dildo.

Kellie and Taylor's clits connected at the middle of the double-header. They bucked together, fucking each other and getting fucked. Their skin flushed, and both moved closer to orgasm, as did Carrie riding Monster Vib.

I was alone for the moment, so I stretched out on the bed to watch the fun. The women grunted, groaned and, almost simultaneously, came. The scent of their inner juices brought a large smile to my face.

Kellie and Taylor kept at each other, rubbing and fucking. I slipped over to Carrie Underwood and flipped her on to her back. I removed Monster Vib and lowered myself atop her. She reached down and slid my cock into her stretched-out pussy.

To my surprise, Carrie was able to contract her inner labia and grasp my cock. I gasped, then started pumping. The Idol winner pulled my mouth to hers and we kissed, long and hard, as we fucked. Her hips started rising to meet my thrusts.

I could hear Kellie, then Taylor, cum, but my focus was now on Carrie. Our mouths remained glued as our nether regions ground together. My cock, firmly embedded into her pussy, slid in and out. My groin rubbed her clit.

Her kiss changed from loving to desperate. She raised up and came, allowing my cock to feel her wetness increase in her pussy. I was close to cumming myself, and settled into a stronger stroke, ready to shoot my load.

I felt four hands pull at my hips, and I slid out of Carrie Underwood. Taylor Swift and Kellie Pickler, now free of the double-headed dildo, flipped me over and started sucking my cock, one on each side of me. Carrie shifted her position and came up between my legs to join her friends.

Three women sucked and stroked my cock and balls. Three Country stars worked on my rod, getting me closer and closer to cumming. Three beautiful naked women lavished all their sexual excitement on to me and my eight-inch shaft.

I tried to hold out, honestly I did. This was a very erotic moment, and I wanted it to last. But my body was ready, and my cock erupted for the last time that night. Semen squirted from the little slit at the end of my cock. Each woman tried to drink it in, but in all honesty, they got more semen on their faces than in their mouths.

Sated and now thoroughly tired, I lay there in the middle of the bed. The three women giggled as they licked cum off each other's faces. Then they sort of shoved me over to one end on the bed and resumed their lesbian play. Breasts, pussies, mouths and dildos combined in a fervor I had not seen before.

I wish I could describe that night fully, but I have to admit that, despite the sexy vibrant sight to my right, I fell asleep. I had been worn out by these three young women, along with the others at the earlier CMO.

My dreams were even sexual, or at least I thought them dreams. I remember tits shoved into my mouth again and again. I remember tongues licking at me. I remember asses bumping into me. The almost-constant movement of the bed as these three youngsters continued to play rocked me in my sleep.

At one point, I remember dreaming (?) that Kellie was sucking my cock while Carrie sucked my balls. Then Taylor hopped onto my now-hard cock and fucked me until she came, with Kellie rubbing her clit and sucking her breasts and Carrie fucking her ass with one of my strap-ons. That one HAD to be a dream. My cock was too worn out to rise again, wasn't it?


About five in the morning, I felt the need to pee. I noted all three women were asleep, arms and legs tangled together. I softly rose, not knowing when the women had finally fallen asleep.

I padded naked into the bathroom and did my business. After washing my hands, I felt a hunger gnawing at my innards. I knew true morning was close, so I decided to not eat, but I went into the main room to see if there was any juice in the refrigerator.

I found a bottle of orange juice. I opened it, walked to the upper deck in the living room, opened the drapes and looked out over the city, lost in thought. I was so lost in thought that I didn't know someone was behind me until I felt her press her breasts into my back, hug me from behind and kiss the back of my neck.

I turned, and found it was Taylor Swift behind me. I leaned my head down and kissed her back. Our kiss was deep and passionate. Her hands lowered to my ass and pulled my crotch against her own. Damn, my cock proved resilient right then and started rising.

"You are so wonderful," Taylor said when we finally broke our kiss.

"I'm just inspired by your presence," I responded. "I thought that night in December would be our only time together."

"You have not been out of my thoughts since then," she admitted. "And you have given me so much recently."


"The Friday night get-togethers Carrie, Kel and I have won't ever be the same after tonight. We did some talking, and we're gonna be almost inseparable. We've even decided to not do a CMO unless the other two are there."

"I'm happy for you. Not only will you have good friends there, but you've got an even deeper secret between you three now."

"Thanks to you," she said.

"Nah, you would have discovered each other without my help."

Taylor giggled. "You know what I've discovered?" she innocently asked.

"What?" I said, falling into her trap.

"I've discovered that we're naked to anyone looking into these windows, and I want to give that person more than naked bodies to look at."

Voyeurism? I thought. What the hell.

Taylor turned me sideways to the big window and dropped to her knees. Her mouth expertly sucked my cock down her throat, sucking me to full hardness, then continuing to suck even after my cock flared inside her mouth.

Finally I pulled her mouth off my cock. She looked around, then climbed on the table, with her pussy facing the window. "Eat me," she cried. "Eat my cunt!!"

I knelt and started licking her pussy. She was very very wet. My tongue lapped at the juices already dripping out her body. Two of my fingers dove deep into her body, feeling the wetness inside her pussy. Her moans increased, and I also heard her say "Look at me, world! Taylor Swift is getting finger-fucked!"

I varied the motions of my fingers while my tongue searched out her clit. I licked and sucked the little bud while my fingers inside Taylor's body bent and grazed her G-spot. Taylor immediately went rigid, screamed "I'm cumming!!" and flooded my hand with her orgasm. I kept the motion going until she finally resumed a normal breathing pattern. Then, with a last lick at the pussy, I removed my hands.

Taylor grabbed my arm and pulled my wet fingers into her own mouth. She sucked all her cum from my hand, then looked at me and smiled.

"Fuck me, right here!" she said in a throaty voice.

I stood, aimed my hard cock, and shoved deep into her pussy. She sat up on the table, groaned and then kissed me. My motions inside her increased as the kiss grew in passion. Finally she broke the kiss and leaned back. Each thrust into her caused her breasts to bounce up and down. Her moans increased again. I wondered if Carrie and Kellie were still asleep in the bedroom, and if they were, how they could sleep through Taylor's loud moaning.

But we remained the only two people in the living room.

After several minutes, Taylor said, "Remember the airplane sex?"

"How could I forget?" I asked. After all, it was only yesterday morning, less than 24 hours ago.

"Take me like you did there, against the window instead of the wall," Taylor begged. "Only take me from behind!"

I pulled out of Taylor's pussy. She whimpered a moment, then moved against the large window. I got behind her, lifted one leg, and reinserted my cock into her pussy. With the first shove, Taylor's naked body was plastered against the window, breasts smashed against the glass.

Taylor gasped, then got into her own fantasy. As I fucked her, she was saying, "Look at me! See my body against the window! See my lover fucking me! Look all you want! You'll never get this pleasure, people, but look anyway. LOOK AT ME CUMMING!!!!!"

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