tagCelebrities & Fan FictionWhen Taylor Met Lindsay

When Taylor Met Lindsay


This story follows directly the events chronicled in "Backstage With Taylor Swift, Pt. 5". It can be read as a stand-alone, of course. Events mentioned in this story also refer to a five-part story arc, "Meeting Lindsay Lohan," also written by the author. Again, not reading those stories will not detract from this story, but will add knowledge of the events that transpire herein.

As mentioned in the Disclaimer above, this is a work of fiction. While resemblance to persons still living is intended, I in no way wish to imply this actually happened. But if it did, it would be nice!!

This is also the author's first attempt at writing a first-person from the female side. Critique is always welcome, but please be gentle.


I admit I was shocked.

I stood in the Penthouse of the Beverly Wilshire Hotel with my lover and boyfriend. I had been told not to speak, but I couldn't help myself.

Oh my God! Oh my God! oh my God!! Finally I couldn't hold it in. "Oh my God, that's Lindsay Lohan," I exclaimed.

My man, whom I will refer to as Sweet, looked over at me for an instant, and I quieted. But then something even stranger occurred. Lindsay looked up at him through bloodshot eyes. Seeing him, she scooted off the bed, dropped to her knees and kissed his booted feet!!

As if that wasn't enough, she spoke. "You've come for me," she said. But what she called him almost floored me. "Thank you, Master!"

OK, time to get my bearings. Start with the basics. My name is Taylor Swift. I'm a Country singer, My records have been on the radio for a little over a year. Pretty successfully on the radio, too, based on my recording of "Our Song" being Number 1 for six weeks,and my song "Teardrops on My Guitar" breaking into the Pop Top 10. I'm here in LA after an emergency flight from Dallas with Sweet, the man Lindsay called "Master" (he's not MY Master, I'll tell you that!).

OK, flashback time. Maybe that will help me get my bearings. I met Sweet shortly after my 18th birthday. I did a concert in his hometown back east. It was supposed to be a special night for me. I was going to be inducted into the Country Musicians' Orgy group, the CMO.

When I was told about the CMO, I had been given some basic directions. Post-concert, I was to play with myself to prepare for the Orgy. Then someone would come to me and that person and I would have a one-on-one sexual encounter before the orgy started.

I was very nervous. For one thing, I was still a virgin before that CMO. One drawback to being a singing sensation is the constant workload. Concerts, recording sessions, practice. Man, that left no time for boyfriends.

So when Sweet walked into my dressing room while I was frigging myself, I thought he was the opening act. He had wandered in innocently enough, he later told me. He had won a local radio contest and that included a backstage pass. So he entered my dressing room. I'm half-naked, hot, horny, and he's not that bad looking. What the hell, I thought, he's the opening act.

So we made love. He took my cherry, in a coupling both sensuous and startling in its intensity. More startling was when my dressing room door opened and the real members of the CMO entered, led by my friend Carrie Underwood. Carrie was the opening act.

Well, I got Sweet to stay for the orgy. Afterward, I thanked him for taking me first. I never thought I'd see him again, but he stayed in my thoughts.

Two months later (last week my time), I learned of the next CMO. I was to be the opening act, with Bucky Covington. Remember when I mentioned that hectic schedule? I had not had sex since that first orgy.

I was in a panic. Then I thought of Sweet. I had my publicist find out where he lived, and last Monday I popped up at his door. I didn't know what to do with Bucky. Well he had some great ideas. We practiced (that was fun!), then we went to a strip club so I could learn how to strip. I bought the outfit I am wearing now, and had some more fun.

Yesterday he and I flew to Dallas, where the CMO would be. That was a day. We joined the Mile-High Club, learned about orgasm control, found out my best bud Kellie Pickler was also in the CMO, enjoyed the orgy, then partied the last of the night away with Sweet, Kel and Carrie, who was also in Dallas.

Today the four of us kept the party going. At least, it was going until Sweet got that call from the woman I now know was Lindsay Lohan. We dressed (both of us in black, our clothes covered by similar trench coats), hopped on the first westbound flight and somehow got into the penthouse at the Beverly Wilshire.

The man I had said "I love you" to has been full of surprises since we hit LA. While we rode the elevator up, he produced this awesomely-huge paddle. First thing he did when we entered this room was to beat the hell out of Lindsay's butt. Damn, it's really red right now. But she's not crying, she's just kneeling there in front of him.

"Rise, little one," Sweet said. "How much have you slept today?"

"Just off and on since I called you," Lindsay said. "That isn't the girl I remember you with last time, is it?"

Oh my GOD!! He just slapped her face!! "How dare you speak about subjects I have not brought up first," he spat angrily at her.

"I'm sorry, Master," Lindsay said contritely. "I just miss my sister emmy. I hoped she would be with you."

"Well, you are right, little one. This is my friend Taylor. YOU will refer to her as Mistress. And you will speak as I taught you"

HOLY SHIT!! This is getting even more intense! Me, a Mistress?

"Girl doth greet thee, Mistress Taylor," Lindsay said. She looked up at me for a second. The welt from his hand showed prominently on her right cheek.

"Do you have any upcoming movie shoots, girl?" Sweet asked.

"No, Master," she said. "Girl's wild ways hath lost her any movie deals for the foreseeable future."

"Do you like the woman I brought with me, girl?"

"Master, girl thinks Mistress Taylor is very pretty. Girl thinks she recognizes her from somewhere, but cannot remember where."

Sweet looked at me, then whispered, "Go ahead, kiss her. Gently, though."

I stepped up and gently took Lindsay Lohan's face in my gloved hands. I bent down and gently kissed this woman I had been watching on TV and movies since I was 10. She kissed me back, a kiss full of needs and desire. But let me tell you, her breath smelled of alcohol, and it was a bad smell at that. I broke the kiss and stepped back.

"Thank you for the kiss, Mistress Taylor," Lindsay said.

Sweet then produced a set of handcuffs and a blindfold from the recesses of his travel bag. He shackled Lindsay to the bed, then told her "You will sleep, little one. This blindfold will help keep the afternoon light from your eyes. Mistress and I will be going out for a bit, but we will return when you have slept off most of the alcohol in your system."

"Thank you, Master," Lindsay said. "Girl will be here."

I giggled. Handcuffed like that, she wasn't leaving. Sweet and I retreated from the bedroom into the main room, closing the door behind us.

As soon as we were alone, I turned to Sweet. "What was THAT all about?" I asked. I certainly didn't want anything like that being done to me, that's for sure.

"Sssshhhh, Tee," he said. "Let her sleep. We'll talk in the car."

We left the hotel and got in the car he'd rented at the airport. As we drove to the local Home Depot hardware store, he filled me in on his past with Lindsay Lohan.

"I met her in New York on her 18th birthday," he said. "I was with a girl then, and we were in a Master-slave relationship. Lindsay had been dumped by her then-boyfriend, and my girl and I took her in. We made love to her, and taught her how to be a submissive.

"Lindsay joined my girl and me for a few weeks, learning her role well. But she has not called me for several years, and I had promised not to call her. I've watched her life spiral out of control, powerless by my word not to help her. Now, with your help, I hope to straighten her out and set her back on a good path."

"What happened with that other girl you mentioned?" I asked.

He was silent for a couple of blocks. When he spoke, I could barely hear him, and I knew speaking was hard. "She died," he said. "In my arms. She was so young, so vibrant. But she had a genetic disease, and it took her three years ago." My heart broke hearing the pain he still felt, a pain that came out in his voice.

We had stopped at a red light by the time he finished speaking. I leaned over and kissed him, giving him with that kiss all the love I felt for him. And I did love him. He had made me feel special. He had not done anything I had not wanted him to do. He had loved me fully and unconditionally, asking nothing of me. Now, I decided, I would do anything he asked.

When we reached the Depot, he made several weird purchases. He bought two 2"x8' boards, some smaller 2"x2' boards, some Velcro, a long-lasting glue, a staple gun, some nuts and bolts, nails, and a drill. He added a hammer and screwdriver set at the last minute.

"What is all that for," I asked. It made no sense to me what he was buying.

"I'm planning to make an X-brace to put Lindsay on," he replied.

"An X-brace?"

"Yes, my darling Taylor. I plan to tie Lindsay to the brace and beat the alcoholism and drugs out of her."

"What is my role in this," I asked. "I couldn't do that to someone. And you'd better not THINK about doing that to me!!"

"No, my love," he responded. "You and I are not a BDSM couple. I would never EVER do anything to hurt you. But Lindsay is different. She chose, years ago, to be my submissive. She signed a contract that allows me to do anything I see fit to her, provided I leave no visible marks, nor marks that might be seen if she's doing a movie."

"I'm still a little lost," I said. I mean, think about it. Two months ago, I was a virgin. Last week, I'd only had one night of sex. I do admit that last Monday, I played a little fantasy with whatever he name was, that stripper. But the only time I'd ever read about Master-slave relationships was when I studied the Middle Ages, and it was a decidedly non-sexual study. I know nothing about it in the 21st Century. I explained all this to Sweet.

"Ask me anything," he replied confidently.

"Why am I 'Mistress Taylor' to Lindsay Lohan?" I asked.

"She needs to know she is the inferior here. You are above her. You can then tell her what to do as we detox her.

"Here's my full plan," Sweet explained. "I'm going to be hard as hell on her. She might even grow to hate me as we clean her up. You, my love, are going to be her friend, protector and yes, her lover."

"Lindsay Lohan is bisexual?" I said with a start. "It wasn't just that kiss?"

He laughed. "Don't you remember. When I met her, I was with my then-slave. We BOTH made love to her. Now, my darling, I need you to be Good Mistress to my Bad Master. Can you do it?"

"You'll help me?"

"Yes, my darling. I will."

"Then yes," I agreed. "Provided I can tell everything to Carrie and Kel."

He agreed, and our plan was set in motion.


It looked pretty funny, having the bellhop drag all that lumber and other building materials up to the Penthouse. Sweet built the X-brace while Lindsay slept. My assignment was to keep Lindsay company.

About 10 that Sunday evening, Lindsay Lohan awoke. She struggled a minute against the handcuffs, then called out, "Who's there?" She could feel my body on the bed.

"It's Mistress Taylor," I said. That name sounded funny coming from my lips, but he told me I should call myself that around her.

"Mistress," Lindsay said, her voice suddenly meek. "Please let this girl see your beauty again. In my earlier haze, I'm not sure I saw you right."

I pulled off the blindfold. The only light in the room came from a lamp behind Lindsay. My entire face was lit up. Lindsay smiled.

"I was right earlier, Mistress. You are beautiful. Please, Mistress, remove your coat so that I can see all of your body."

I stood and took off my trench coat. Her eyes lit up.

"Please, Mistress Taylor, honor this girl with another kiss. I can barely remember the first one."

I returned to the bed, leaned over her, and kissed Lindsay Lohan again. This time, she kissed me back. More importantly, she no longer tasted of bad alcohol. Our lips parted, and our tongues met. One of my hands went to her waist, while the other caressed her cheek.

I admit the kiss turned me on. This woman was one of my idols growing up, and now I'm kissing her! And she was kissing me back. Kissing me and more. Although still handcuffed, meaning she couldn't hold me in her arms, Lindsay wrapped her legs around me, grinding her cunt into mine.

Oh! My!! GOD!!! Lindsay Lohan wants me!!!!!!!!

I broke our kiss and looked down on the 21-year-old under me. "Are you sure you want to go on?" I asked.

"Yes, Mistress," came the meek reply. "Girl wants ... no, girl needs your love. And girl wants to love you."

I'd never heard anyone speak in third person before except as a joke. Having Lindsay speak to me in third person, though, turned me on.

I stood and removed my black dress. Underneath was the stripper underwear from the night before ... leather half-bra, leather thong, black garter belt holding up black stockings, and elbow-length black leather gloves. Lindsay's eyes lit up. I could tell she approved of my underclothes.

Lindsay was still as naked as when we had arrived, and I leaned over her. My mouth gravitated to her breasts, and I tentatively licked at a nipple. Despite the two orgies, and the past night spent in bed with my best buds Kellie Pickler and Carrie Underwood, I was still a neophyte when it came to making love with a woman. As I started, I remembered Sweet's words.

"Do to her what you would want done to you."

So I bit on Lindsay's right nipple and pulled at it with my teeth. She moaned louder and squirmed under me. I caught her left nipple between two gloved fingers, and with teeth and fingers, pulled both nipples together. Lindsay lifted her ass off the bed in joy.

I was experimenting with this woman now. I caught the outer edge of both breasts and shoved them together hard. The nipples moved very close together. With my hands keeping her breasts captured, My teeth and tongue went from one nipple to another, kissing, biting, licking, enjoying the taste of her areolas in my mouth.

Finally I released the breasts with my hands, although I kept one nipple captured in my mouth. One hand went behind me, quickly undoing the bra and freeing my own breasts. Lindsay looked at them in awe. They're not as big as hers, but the nipples were already as erect as the nipples I was sucking.

My other gloved hand slipped down her shaved mons and settled on her swollen pussy lips. I rubbed them, to the sounds of another joyful moan from Lindsay, then looked at my glove. Yep, the fingers were wet. I didn't want to ruin the gloves, so I swiftly removed them.

The next time my hand went to her pussy, it was now a bare hand. I could feel her juices. I could also feel Lindsay's erect clit as she strained for me to rub it. I, however, had other ideas. I took two fingers and shoved them into Lindsay Lohan's pussy.

She changed immediately. From a moaning woman, Lindsay became like a beached fish, flopping up and down on my hand, lifting off the bed in her near-orgasmic fervor. I stroked harder into her, biting her nipple even deeper to retain contact. Lindsay just cried out in lust and joy and continued humping my mouth and hand.

Then I heard words I myself had spoken, but had never been spoken to me before. Lindsay growled, "I need to cum, Mistress. Please, girl needs to cum. Please PLEASE let girl cum!!"

I thought for a second about my orgasm control sessions with Sweet, but decided now was not the time to test Lindsay. I lifted my mouth off her breast (catching a quick glimpse of the teeth marks around her areola), and said, "Cum, Lindsay."

Her orgasm was so intense as her inner labia walls squeezed my fingers that it pushed my hand out of her pussy. She cried out in joy and continued cumming, flooding her pussy with juices that slid out of her pussy lips and onto the bed.

I was really turned on now. I pulled my thong down my legs and placed myself over Lindsay, dropping my cunny on her mouth. My mouth went to her pussy, and I licked at the juices still seeping from her pussy lips.

Lindsay, for her part, lifted her head and bit on my labia, causing me a greater pleasure. Her tongue lapped and lapped at my outer lips. I had an advantage on her, because my hands were free. I spread her lips and licked the inside of her pussy walls, then added my fingers back inside her body. I curled them, and could tell by the way Lindsay almost threw me off her bucking body that I had found her G-Spot.

A couple of scrapes with my nails on to her G-Spot, combined with my tongue licking inside her, caused Lindsay to cum again. I figured she couldn't ask to cum because her mouth was glued to my pussy, so I lapped and drank as she gave me her internal juices with no complaints.

When she was done feeding me cum juice, I needed to cum. But she just couldn't get her tongue deep enough inside me. So I reached down and spread myself open. This time, when I lowered on to her tongue, the woman under me found the spot I really needed licked. Lindsay lapped and scraped with her teeth. I rewarded her with ... oh God, yes! ... an orgasm of my own, nearly drowning my personal idol in my juices.

When I finished cumming, I twirled around, and Lindsay and I kissed again, this time sharing the cum in our mouths and on our lips with each other.

We were locked this way when Sweet entered the room. He was still dressed in black jeans and trench coat. "I could tell you were done when the sounds ceased," he said.

"Master," Lindsay said, "Thank you for bringing Mistress Taylor into my life."

His voice changed from pleasant to frightful in an instant. "Did I tell you to speak, little slut?" he spat at her.

At once Lindsay was the meek little girl of earlier in the day. "No, Master," she said softly.

Sweet walked over and backhanded Lindsay, giving to her left cheek what he had given her right ... a red welt. He then produced from one of the trench coat pockets a dog collar and leash. He attached the leash around Lindsay's neck, unlocked the handcuffs, and started pulling her off the bed.

Lindsay followed, keeping on her hands and knees. Sweet took her to the X-Brace. "Stand," he ordered.

She stood, and Sweet strapped her on to the contraption, her bare back facing out. Then he stepped back and produced a flogger with what looked like glass shards embedded in the ends of the leather pieces.

I couldn't hold back. "No," I cried. "Don't hit her with that."

Sweet looked at me angrily. "I have to do this," he said, "But you don't have to watch, Tee. Go back in the other room."

"I'll stay, if you don't mind," I responded. "After all, someone has to watch out for Lindsay."

Sweet lifted his hand, said "You will not drink without my permission, ever again," and slammed the flogger onto Lindsay's back.

Red welts appeared, but Lindsay only said, "Girl understands and begs forgiveness."

He hit her again, saying "No drugs unless they are prescribed, you little slut!".

The redness deepened. Again, Lindsay only said "Thank you, Master."

A third hit, and another "Thank you." If it were me there, I'd be screaming my head off by now. A fourth hit, then a fifth, all punctuated with a soft "Thank you, Master."

On the sixth hit, Lindsay finally screamed in pain. Her back was now a deep red, and it looked like Sweet had drawn a little blood. But still he beat her. Seven. Eight. Nine. Ten. Lindsay Lohan screamed in agony with every hit now, Wounds opened, and blood dripped from her back.

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byrpwilbur© 7 comments/ 60297 views/ 24 favorites

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