Lindsay's First Time

I was doing some shopping downtown one afternoon when I decided to stop in a coffee shop for a hot chocolate. After getting my drink, and much to my surprise, I found an empty table. I had been on my feet for several hours at this point, so I decided to sit and enjoy a moment's rest. I have a habit of scanning crowds and watching people, so it didn't take me long to notice the gorgeous young woman sitting across the room, reading a book and drinking a cup of coffee. She looked somewhat familiar but, being winter, she was wearing a heavy jacket and a hat, so it was hard to tell. I kept my eye on her as she sipped her coffee between her luscious lips, not looking up at all until she was finished. She closed her book, got up and left. After watching her gracefully walk out the door my eyes returned to her table, where I noticed she had left her gloves. I'm sure she would have noticed quite quickly, but I wasn't going to pass up this opportunity to meet her. I darted across the room, grabbed her gloves, then rushed out the door. Thankfully I had noticed the direction she turned when she left the coffee shop, and she hadn't had much time to go far. I dodged a few other pedestrians as I jogged up to her.

"Excuse me!" I said as I caught up to her. She turned to face me. "You left these back at the coffee shop."

"Oh my god!" she said. "Thank you, I can't believe I didn't notice that!"

We engaged in small talk for a few minutes before I introduced myself.

"It's nice to meet you," she replied, shaking my hand. "I'm Lindsay."

"I knew I recognized you!" I exclaimed, happy that the mystery was now solved. "Lindsay Lohan, right?"

"I didn't think anybody would recognize me if I kept bundled up," she said, blushing just a bit.

"How could I not recognize a gorgeous face like yours?"

She thanked me for the compliment, and we talked and walked for a couple of blocks.

"Look," she said, "I was just heading back to my hotel to get warmed up. Would you like to join me?"

At that moment I did what any heterosexual man would do when asked that question by a woman as sexy as Lindsay Lohan. I tried to hide my gleeful excitement, then calmly (I think) agreed to accompany her back to her hotel.

We walked the few blocks to get to her hotel, then took the elevator up to her floor. As soon as we were in the room, she shut the door and immediately started taking off my jacket. We kissed briefly, but not much as we proceeded to remove each layer of clothing that the other was wearing. She took off her own hat as I removed her jacket, then I pulled her sweater over her head. Incredibly, she wore no bra under her sweater, and her full breasts didn't seem to be sagging at all as I bent forward to kiss them. Her nipples grew instantly hard, but she pushed me back in order to pull off my sweater, leaving us both topless. As I returned my attention to her breasts, she undid my pants, reaching inside and rubbing my cock through my underwear. I guided her into the bedroom and onto the bed. We both kicked off our shoes, then she quickly pulled my pants down. I removed them all the way, along with my socks, leaving me in nothing but my underwear. I pushed her back so she was lying down on the bed, then I undid her pants and pulled them down and off, leaving behind her white socks and a yellow thong. As I kissed my way back up her body, she reached down and pulled my underwear down just enough to free my hard cock. I pulled them off the rest of the way, letting her rub my cock a bit, then I pulled off her thong, revealing her partially trimmed pussy. Seeing Lindsay Lohan naked, except for a pair of socks, was almost enough to push me over the edge right then and there. I held it together, though, and pulled away from her, burying my face between her thighs. She moaned softly as I kissed the area around her pussy, then I started to gently brush my tongue and lips across her clit and pussy lips. I looked up to see that she was caressing her own breasts as I started eating her out more enthusiastically, fucking her with my tongue.

"Oh my god!" she screamed out a few minutes later. "I'm cumming!" She bucked her hips as her orgasm hit, and I continued to lick her as her orgasm ran its course. When she finished cumming, she pushed me away and rolled me onto my back. Kneeling beside my hips, she bent over and took my cock into her mouth. She managed to work just over half of my eight inches into her mouth, using her hand to stimulate the bottom of my shaft. I got the feeling from her sloppy technique that she wasn't very experienced at this, but I didn't care a whole lot. The fact was that Lindsay Lohan was naked and sucking my cock.

"Does that feel good?" she asked, stopping for a moment.

"It feels great," I answered.

"I love your cock," she added before taking it back into her mouth. She sucked it for a couple of more minutes, then pulled away. She laid down on her back and pulled on top of her. As I positioned myself to slide my cock into her pussy, she stopped me. "Be gentle," she said, "I've never done this before."

I was surprised, but I chose not to say anything in response, fearing that she might change her mind. I grabbed her ankles and placed her legs on my shoulders, then watched her beautiful face as I slowly inched my cock into her virgin cunt. It took almost five minutes to get my entire cock into her tight pussy, and when I did it took a few more minutes before I was able to fuck her with any real amount of speed. She kept her eyes closed most of the time, but occasionally opened them to look at me as I fucked her. Eventually I built it up to a rhythm where I was fucking her quite hard and she was enjoying every second of it.

After a few minutes I stopped just briefly. I stayed inside her, but rolled her onto her side, keeping one leg up on my shoulder and straddling the other. I resumed the hard pounding I had been giving her pussy as she reached down and started rubbing her clit.

"You're so fucking gorgeous," I said. "I can't believe I'm doing this!"

"Yes baby!" she said as I continued to pound her. "I love your dick!"

"It feels so good!" I said.

"It feels fucking incredible!" she cried. I kept pounding her for a minute, then she started to cum. "Fuck! Yes! Oh god! Fuck yeah!" she cried out as I kept fucking her through her orgasm.

"That feels so fucking good, Lindsay!" I said as her orgasm died down. "Oh yeah, take that cock!"

It only took another minute or two before she was screaming out, cumming once again.

"Do you want me to go on top?" she asked after her orgasm subsided. I responded by pulling out and lying on my back. She straddled me and grabbed hold of my cock, impaling herself on it. She leaned forward and quickly began bouncing her hips up and down as I took advantage of my position to kiss and suck her incredible breasts.

"Ride that cock, baby!" I said as she moaned wildly. "That feels fucking great!"

"Oh my god baby!" she yelled. "I'm cumming again!" As soon as she came I knew I was about to explode. I let her finish her orgasm, then I pushed her off of me and onto her back. I'm not sure if she knew what was about to happen as I knelt beside her head, rubbing my cock. Seconds later I exploded, shooting a huge load of cum onto her face. I don't think she enjoyed it very much, but I was beyond the point of caring about anything. As soon as I finished Lindsay got up off the bed and went to the bathroom. I wasn't sure whether I should stick around, or if she wanted me to go, but I decide that it was better to play it safe and stay. It was only a minute before she emerged from the bathroom. She was still naked, but the cum was completely washed off of her face.

"That felt incredible," she said, lying down beside me. She reached over and grabbed my semi-hard cock. "Thank you for showing me the ropes."

We had sex one more time before I left, although I got her to swallow my cum the second time. I haven't seen her since, but we have exchanged a couple of e-mails… I can't wait for a second meeting.