Meeting Lindsay Lohan Ch. 01

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He & slave meet Lindsay Lohan.
1.8k words
4.27
88.6k
20

Part 1 of the 5 part series

Updated 09/24/2022
Created 07/06/2004
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rpwilbur
rpwilbur
117 Followers

I had been following Lindsay Lohan's career for years. She was wonderful in Parent Trap. She blossomed in Freaky Friday. She grew into a woman during Mean Girls. But I never envisioned actually meeting her, nor what would come from that meeting.

Allow Me to introduce Myself. My name is Robert. I am known as Master SweetShadow, a real-life BDSM Master. My slave emmy and I had traveled to New York City for the 4th of July weekend, and were making the rounds of all the sights. This was our first trip to the Big Apple. We saw Ground Zero, Central Park, Times Square.

As we entered the elevator to take us to the Observation Deck of the Empire State Building on July 2, we were surprised when Lindsay Lohan entered the car just as the doors were closing. I silently muttered a curse, since I had planned on having My slave give Me an elevator blow job, but not with this girl in the car with us. But then I noticed who she was, and that she was crying. Getting My nerve up, I spoke to her.

"Excuse Me," I opened. "You're Lindsay Lohan, aren't you?"

"Yes, I am," she replied through sobs. "But I'm in no mood for autographs."

"What's wrong?" I asked.

"It's my 18th birthday today, and I just had a major fight with my boyfriend Wilmer. I guess I'll be spending my birthday alone now."

"Wilmer Balderrama, the guy on 'That 70's Show?' What did you fight about?" emmy asked her.

"We've been dating for several months now, and he's been pressuring me to have sex with him," Lindsay explained. "Today I planned to sleep with him for my birthday, but the asshole wants nothing to do with me now. He says I'm 'too old' now." Lindsay started crying all over, and I automatically moved over to comfort her.

I then took a bold step. "Listen," I said. "Why don't you spend the day with us. I'm Robert, and this is my girl emmy. We're big fans, and we'd love to turn this day into the happiest of your life." I did not mention My exact relationship with emmy, as it was not Lindsay's business ... yet.

Happily, she agreed. I smiled at her, and was rewarded with a small smile back from Lindsay, and a larger smile from emmy. At that point the elevator doors opened, and we emerged on the Observation Deck.

It was a clear day in New York, and we could see for miles in all directions. My arm moved automatically to emmy's waist as we looked, and Lindsey slipped very close to my other side, tentatively putting her arm around My waist. I took My free arm and encircled her waist, pulling her as close to Me as I could. Lindsay put her head on My shoulder, and made herself at home in My grasp.

After a while, we headed back down to the street. I was surprised to see a limousine at the curb, and Lindsay guided us directly towards it. emmy and I had taken the subway, so we joined our celebrity friend in her ride, covering our faces as the press photographers started snapping photos of the three of us.

She asked where we wanted to go next. I replied, "It's your birthday. Where do you want to go?"

"I know just the place," she said. She whispered to her driver, then closed the privacy window as the car drove off.

Lindsay sat next to Me, and I was surprised and pleased when she pulled My head around and kissed Me softly on the lips. I responded automatically, and Lindsay darted her tongue into My mouth. When we broke the kiss, she said "Thank you for being here."

The car soon lurched to a stop. I was amazed to see we were at a major Park Avenue hotel, one way over My budget. She said "Come with me, please." emmy and I followed eagerly, wondering what was in store for us.

We rode to the 37th floor, where Lindsey led us to a very opulent room. In it was every comfort the hotel could think of, from deep shag carpet, to complimentary lunch, complete with champagne. I spoke to emmy, and she got up and served a small meal for the three of us. As she did so, Lindsay watched in wonder as emmy did the entire service from her knees, as is only proper for a slave.

When she finally asked why emmy was kneeling, I explained that she was My slave, I am her Master, and she does whatever I order her to, to gain My pleasure. At this comment, Lindsay immediately dropped to her knees before Me. "I want your pleasure too, Robert," she said, surprising Me.

"Are you sure?" I asked. "Do you understand completely what it means to get My pleasure?"

"Yes, I do," she said. "I want to thank you properly for being with me."

"Then come sit in My lap, Lindsay."

The girl quickly obeyed, climbing into My lap, squirming in to be comfortable. Her squirming affected Me, and My cock started growing. Lindsay giggled softly, then squirmed some more.

I kissed her then, deeper this time. Lindsay responded well, wrapping her arms around My head, and rubbing her body on Mine. Our tongues clashed happily as I waved My hand, and emmy slid away, leaving Lindsay and Me alone.

My hands moved quickly, unbuttoning the blouse Lindsey wore. I pulled it off her body, and was rewarded by a braless Lindsay Lohan, showing Me the breasts I had been fantasizing about since seeing her on Saturday Night Live. One hand went to each breast, pulling the nipples to rock hardness. Lindsey moaned into My mouth, showing her pleasure at My breast play.

Her hands worked at My shirt, baring My chest to her touch. I lifted her up as she curled My chest hairs around her fingers, and carried her gently to the massive bed the hotel provided for its prime celebrities. I placed her down, marveling at the softness of the mattress and the silk sheets above it. emmy, anticipating My needs, had stripped the bed of the throws and blankets, allowing Lindsey and I to get right to our fun.

My hands went to her skirt, and I slid it off her smooth shapely legs. In another motion, I had removed her shoes (no socks) and a third motion stripped her of her panties. I then spread her legs, and with her grabbing My hair for encouragement, I started licking at her velvety pussy lips.

Her wetness flowed into My mouth as My tongue probed her clit, then dived deep inside her, then back to her clit. Lindsay's moans filled the room, and her female smell enveloped My senses as I ate her out. She bucked wildly against My face, and finally, all too soon, she came. I was surprised when she squirted her cum in My face, her screams of pleasure filling the room.

She rested a minute, as I placed soft kisses on her wet wet pussy, letting her calm down. Then My goddess Lindsay rolled Me over, and skinned My pants and shorts down My legs. I barely had time to kick My loafers off before she pulled my lower bodywear off. Then Lindsay climbed back up My body, and pulled My semi-rigid cock into her mouth.

She was not the best cock-sucker in the world, but she had plenty of potential. What she lacked in experience she made up for in enthusiasm. She sucked deeply on My cockhead, then tried to take Me deeper in her mouth. After getting half of My shaft down, she gagged, then started bobbing up and down Me with her mouth. Her tongue and teeth scraped at My skin, giving Me pleasure beyond measure. Her hands grasped gently on My balls, using her nails to gently scrape at their skin.

After a few minutes Lindsay stopped, and slowly started dropping her mouth lower and lower. When she reached her gag point, I watched in joy as she fought the impulse, then took Me deeply down her throat until her lips were at the base of My shaft. I moaned in pleasure at she then sucked deeply on Me. Precum leaked from Me, and her tongue flicked at the droplets.

She lifted off Me, then crawled higher. The breasts I had fantasized about now wrapped around My cock, and she started sliding My member up and down in her breasts' valley, licking the head each time it showed through the top of her boobs. More precum leaked out, but I was willing Myself not to cum. I wanted her to feel Me deep inside her.

Lindsay reached over to the bedroom table, and opening the drawer, she pulled out a gold-wrapped condom. This hotel provides EVERYTHING, I thought. She opened it up, and slowly slid it down My shaft. After I was sheathed, Lindsay said "I've never done this before, but I want to ... now!!"

She climbed over Me, positioned herself, and with one quick motion, dropped herself right on My covered cock, impaling herself. She screamed immediately, as My member broke through her virgin hymen and she felt a man inside her for the first time ever. She started moving naturally, sliding nearly off Me, then dropping down on Me, again and again. I watched in wonder and lust as her breasts bounced up and down, listened in awe as she moaned My name, and felt her formerly-virgin pussy swallow My cock over and over.

She leaned down, shifting the responsibility of thrusting to Me. I started pumping, and sucked happily as she fed Me a breast. The sucking and pumping, along with My pressure on her clit, did its job, and Lindsay Lohan, woman, had her second orgasm of the night. I never relented in My movements, and Lindsay had a third orgasm right on top of her second.

Keeping My cock inside her, I rolled us over, and started moving again, giving her gentle thrusts at first. As she begged Me for more, I moved harder and deeper, filling her again He & slave meet Lindsay Lohan.and again, faster and faster. I judged the time was right. Two deep thrusts and a wiggle of My groin and Lindsey screamed again and came, flooding My cock with her juices. I could not hold off, so I pulled out at the last second, pulled the condom off My cock, and came, flooding her flat stomach with My white seed.

Lindsay slowly regained her senses, and pulled Me down to kiss her deeply. "Thank you," she said simply. Then her eyes opened in awe, as My emmy came into the room, naked and wet. She crawled on the bed with us, and ...

To be continued...

rpwilbur
rpwilbur
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AnonymousAnonymousalmost 18 years ago
duuuude

nice story, lindsey is amazing and the thought of her as a slave truly original!!!!!! but why does she have to be a virgin in all of her stories

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