Celebs Meet CSSA #17: Leelee Sobieski

[Ed. Note – Several months after hooking up with Rachael Leigh Cook, and Rose McGowan, author TRL journeys to Los Angeles, to hook up with his two favorite “Leading Ladies”. The following is what happens. This continues the “Celebs Meet CSSA” storyline. Enjoy!]

Note: The following story is a complete work of fiction. Anything that happens in it should be taken with a grain of salt. It’s done in an honorary fashion, meant to compliment the people portrayed within. No offense was meant. Do not read this story if you are under 18 years of age, or are opposed to sex between consenting adults. If you are under 18, you
shouldn’t be here anyway. If you’re opposed to sex, you’re going to have an awfully hard time procreating in the future. This story is not meant to reflect honestly on anyone who appears in it. Leelee Sobieski, Rachael Leigh Cook, and anyone else mentioned in this story DO NOT behave like this in person ­ but it would be totally cool if they did! Enjoy!

Celebs Meet CSSA: Leelee Sobieski


Embarrassment comes in many forms.

“So you’re the guy who writes the sex stories about Rachael.”

One form it comes in is when you’re meeting someone for the first time.

“Somehow, I thought you’d be a bit bigger in the penile area.”

And, of course, if you’re buck naked with only the tail end of a bed sheet to cover your manhood from a highly attractive female celebrity, embarrassment is usually multiplied by about five hundred times.

The celebrity in question was Leelee Sobieski, actress extraordinaire, who just also happened to have a body of a young goddess who worked out everyday.

I was the one who happened to be naked on the bed, with nothing but a small triangle off the corner of the sheets keeping Leelee from seeing every part of me. And apparently, my quick yank to cover up hadn’t been quite as quick as I’d hoped.

“Nice of you to notice,” I muttered, looking about for Rachael. Rachael was, of course, Rachael Leigh Cook, my on-and-off celebrity girlfriend, whom had hunted me down because of the stories I’d written on CSSA. Since then, we’d made love, fell in love, fallen out of it, each slept with Rose McGowan, and fallen back in love, all while enjoying the bodies of other women. An open relationship, to be sure, but a fairly stable one, at least as far as Hollywood was concerned.

Today was my first full day in Los Angeles, a far cry from where I call home, and I had, of course, spent the entire night having hot, sweaty sex with Rachael almost from the moment I arrived from the airport. Sleeping in had been a given. Waking up as Rachael greeted an old friend while I lay exposed to half the apartment hadn’t.

“So,” Leelee said, “You’re what, some sort of stalker guy or something.”

“Uh, no,” I said, desperately hoping Rachael would come back from wherever it was she’d run off to. She’d barely spent thirty seconds talking to Leelee, as she’d let her in, and then ran off to some far corner of the apartment, leaving me to fend for myself.

“Oh, so you just write smut about famous women and live out your fantasies when you feel like it.”

“I don’t exactly consider it smut,” I muttered, taking offense at her jabs at my writing, while still desperately wishing Rachael would come pull her off me. “And I wouldn’t say that dating Rachael was specifically living out my fantasies.”

She shot me a look of condescending disbelief. “Ok, but does fucking Rose McGowan count as dating her, or were you just using her to get off.”

I nearly stood up in anger, before remembering my rather exposed condition. “What’s it to you who I slept with and who I haven’t?” I asked instead.

She looked at me, her face growing a bit darker. “I just don’t want you to hurt my friend.”

That did it. Anger coursed through my body, and this time, no amount of nudity would keep me from getting in her face. I shot up, suddenly realizing that, while she was half a head taller than my Rachael, I was that much taller than her again. Glaring down at her, I saw her eyes sink immediately to my package, her eyebrows rising in admiration. I’d always considered myself fairly average in the size department, but then again, I’d never gotten any complaints, so I never worried about it.

Recapturing her attention to my face, I towered above her and held my tone quiet but firm. “I would NEVER hurt Rachael.”

We stared at each other for several long seconds, neither one of us blinking. Finally, as I began to feel a bit silly doing so, Leelee turned away with a scoff, heading towards the window.

“I’m glad to hear that,” she said as she reached the window. “Because if you hurt her, I’ll have to hurt you.” She turned back to me, where I was still standing there. She looked me up and down again, her eyes a bit more appreciative this time than the last.

“Well,” she said a few seconds later, “at least you’re built for a good fucking. I’m sure Rachael’s enjoying your cock, as much as she enjoys any cock.”

“Seemed to enjoy it last night,” I said, feeling my little soldier rising to attention as Leelee walked about the bedroom area. She was dressed for the heat, wearing little more than white shorts and a light blue tank top. Both choices accentuated her long arms and legs in a positive way, and her straight, light brown hair added just the right compliment to her limber figure. The shorts curved with her ass, looking far too pleasant for someone who had just spent several minutes debasing me all together. As she turned back to me, I noticed her nipples were mildly visible through the tank top, confirming my belief that the young starlet had forgone her bra this morning.

Just then, Rachael bounded into the room, carrying a book and a pile of papers. I couldn’t help but smile as I saw her perfect face, and I couldn’t help but become even more erect than I already was as I saw she was wearing a simple white thong and a bra that hugged the curves of her breasts like it was a second skin.

Small, dark haired, and perky in more ways than one, Rachael was the light of my life these days, and not just because she was my Hollywood girlfriend. We had an open relationship when it came to women (she was still exploring her bisexual side), but we always seemed to end up back together, usually when I was in need of a break from work and a big helping of Muse, which Rachael frequently served as. Of course, at the same time, our frequently ending up in bed made finding the time to write harder, but considering I was fucking Rachael Leigh Cook, I figured the guys at CSSA would just have to wait a while longer for my latest masterpiece. I was getting a masterpiece of ass, and typing stories I wasn’t getting paid for just didn’t rank up with that.

“Here you go, Lee,” Rachael said, handing the book and papers to Leelee. “I see you met my babe,” she said, looking over at me and winking. Babe seemed to be her newest nickname for me, though it would probably change before I returned home – and then change again before I got off the plane. Rachael called me just about everything under the sun, except my real name. Somehow, considering the how’s and why’s of our first getting together, that seemed all right to me.

“Yeah, I met him,” Leelee said with a smile – something I hadn’t seen on her face since I’d woken up to it. “He seems pretty cool – I mean, he’d have to be to stand here naked in front of me the entire time.”

Rachael looked over at me, and I blushed despite myself. I lowered my hands as casually as I could to cover the raging hard on that now stood out like a Titan Rocket from between my legs.

“Oh, don’t cover that up,” Rachael said with a sly grin, seeing what I was doing. “I’ll want to use that later.”

Leelee’s eyes went a bit wide at Rachael’s bluntness, but looking over at me, she seemed to calm down a bit. “Is he really that good?” she asked.

“Oh yeah,” Rachael said. I was beginning to feel like a piece of meat the two were haggling over. And then Leelee amplified that feeling. She walked over to me, running one finger across the back of my shoulders as she walked all around me, giving my body a thorough walkabout. As she came around my front again, her face out of site of Rachael for a few seconds, she frowned at me, the made a show out of placing her hands on my chest.

“You know, I bet he would be a good little fuck.” She looked down at my unit and then back up at me again. “Well, maybe not that little.” Both she and Rachael giggled. I simply stared daggers at Leelee.

“I’m sure he’d be happy to show you the ropes, sometime,” Rachael said, coming up beside me. “Isn’t that right, babe?”

I smirked. “Oh, yeah. I’m sure Leelee’s snatch isn’t as tight as yours is, babe, but I’m sure I could get her warmed up enough to enjoy herself-” I continued to smirk as Leelee’s face reflected that she’d caught my jibe, then let it slide past. Then I finished my statement. “With another person, for once.”

I knew Rachael’s eyes were going wide, and I knew Leelee was going to have to respond, but while I expected a slap to the face, or a knee to the groin, or a jab to the ego, what I got instead surprised me.

Shrugging off my debasement of her sexual past (such as it was), she smiled seductively at me, reached up and gently pulled my face down to meet hers. She kissed me full on the lips, jabbing her tongue into my mouth as she pulled me closer. My erect member brushed against the crotch of her shorts, and her nipples jabbed at my chest as she made out with me, right in front of Rachael.

Leelee Sobieski was the third female celebrity I’d ever kissed (behind Rachael and Rose), and just as the other two were as different as day and night, Leelee was different as well. She was aggressive like Rose, soft like Rachael, and had a strange little feeling of naughtiness that both of my other lovers had pulled off on occasion, only to differing degrees.

I realized as I stood there, swapping tongues with her, that Leelee was giving me a rehearsed kiss – a passionate locking of lips that might lead to something more that she’d done a hundred times before. As that dawned on me, I felt the mechanicalness of the embrace, and knew she was acting – probably more for Rachael’s benefit than mine.

Knowing this, I reached up and gently pushed her away, breaking the kiss with a silent smack.

“Yummy,” Leelee said to me, reaching down and gently taking my rock hard cock in her hands. She stroked it once, twice, three times before letting go and turning back towards Rachael.

“Bring him over sometime,” Leelee said. “The three of us can have some fun.” With that, she picked up the papers and book Rachael had given her, and walked towards the door, her ass swaying just a bit more than it had before. Both Rachael and I stood there, a bit slack jawed, as Leelee left the apartment.

“Well,” Rachael said after a moment of the two of us just staring at the door, “You seemed to make quite an impression on her.”

“Yeah,” I said, the image of her nipples poking through her tank top still fresh in my mind. “I guess I did.”

Rachael turned towards me, and as I looked at her, I could tell she was suddenly VERY horny. “Damn, I need you inside me,” she said, reaching up and unclasping her bra. She let it fall to the floor, and then jumped upon me, her lithe little body curling up in my arms as she forced me back onto the bed.

And, as Rachael and I kissed, my hands working her little thong off over her ass, I found myself wondering just how much acting Leelee Sobieski did in a day.

* * *

I love the women of country music. Quite frankly, I’ve always felt that they were a painfully overlooked department when it came to sex stories on CSSA. Oh, sure, Shania Twain and Faith Hill had plenty of stories, but there were a lot of other hotties who desperately needed some fleshing out (and some flesh showing, for that mater), and a while ago, I had set out to do just that – starting with one giant story that would bring a whole mess of Country Music’s top female talent together in one big, jumbo sex story.

And then, things started going wrong. Only another writer can really understand the feeling of looking at a nearly complete story, only to realize that not only was it not the story you wanted to tell, but that the one purpose it was supposed to serve more than any other (turning people on) wasn’t really happening with what you had.

I sat in Rachael’s apartment, my laptop on her desk, as the sun streamed in through the windows, and drank from a tall glass of ice tea. I wore a pair of boxers that Rachael had gotten for me a few days before I arrived in town, and a pair of socks to keep my feet off the cold floor as best as possible while I stared blankly at the screen.

I was in my third rewrite of the project I jokingly called “TRL’s Country Music Clusterfuck.” I say jokingly, because that’s exactly what the writing of the tale had been so far – little more than a clusterfuck of problems, rewriting, and a healthy dose of writer’s block.

Rachael was off to an audition, or something like that, and I had decided to spend my morning and early afternoon relaxing and writing. The two of us were supposed to go out clubbing that night, and while I knew Rachael enjoyed it, I rarely did – except when she decided we needed to fuck in the bathrooms. Ever since she learned that I’d taken Rose McGowan in the ladies bathroom of a club in my hometown, she’d been very anxious to repeat the feat. We’d done it twice when she’d come visiting me, and now that I was out visiting her, I suspected that our tour of clubs in LA would be a tour of the bathrooms of clubs in LA.

Not that I minded.

I was a bit upset that Rose wasn’t in town this week. She was off shooting on location for “Charmed” this week, and would be off in New York for some award ceremony or something the week after, thus ending any chance of mine to run across her and letting her fuck my brains out. Even Rachael was a little upset about that, for she’d wanted to try sharing me with Rose one night, just for the fun of it.

I was idly day dreaming of a threesome between Rose, Rachael, and me, when I heard the door slam shut behind me. Thinking Rachael back early, I turned around and blinked in surprise as Leelee stood behind me.

“Hard at work coming up with more smut?” she asked, her voice icy cold.

“You could say that,” I said, looking her up and down. She wore Capri pants that ended just below her knees while fitting like a second skin, and a button-up shirt that wasn’t buttoned at all – it was tied above her waist, leaving her belly exposed and plenty of cleavage to look at. I felt my cock stir at the site of her.

“What, do you not wear pants ever?” She asked, looking at me in just my boxers.

“What, do you never wear a bra?” I shot back, motioning towards her chest. “And how’d you get in, anyway? Rachael give you a key?”

“No,” Leelee said, looking at me like I was an idiot who’d just fallen off the turnip truck. “But I know where her spare is.”

“Right,” I said, sitting back down. Considering the fact that I didn’t even know Rachael HAD a spare key, I was wondering just how much my girlfriend trusted this woman.

“I’m just here to bring back the book I borrowed yesterday. Tell Rachael I’m going to try and take the role she suggested.”

“Sure,” I muttered, suddenly trying very hard to figure out the best way to have the Trio of girls from SheDaisy pair up with the girls from the Dixie Chicks in lesbian pairs.

“You know,” she said, suddenly right behind me, her arms draped over my shoulders as her hair fell upon my own. “If I had known you were here, I might have called off my lunch date. I’m sure you and I could find something ‘fun’ to do.”

I glanced up at her, and saw the sarcastic look in her eyes. Smiling, I reached up and gently cupped her chin between my thumb and forefinger. “You know,” I said, sweetly, “I bet you’re right. We could get naked, and then I could provide a little anal sex for you.” I saw her eyes go wide, partly in surprise, partly in disgust. “Yeah,” I continued, “My cock sliding in and out of your ass just might loosen up the rod you’ve got crammed up there.”

She went cold, and lifted her arms off me, turning away in a huff. “Funny,” she muttered.

“I aim to please,” I muttered, turning back towards my story.

“You know, I read one of your stories last night,” she said, almost conversationally.

“I’m so glad you could figure out how to run the computer by yourself,” I said sarcastically.

She snorted, and then stood silently for a few seconds. “Aren’t you going to ask me what I thought of it?”

“You already told me,” I said. “You think all my stuff is smut.”

“It is,” she said. “But your story about Rose McGowan was a little different.”

“How so?” I asked, despite myself.

“That’s not how lesbian sex happens.”

“Really? I’m sure you’ve fucked a lot of girls.”

“Maybe I have,” she said, glaring at me.

I snorted. “Yeah, sure. Just like you’ve slept with a lot of guys. You’re what? Nineteen? Twenty? I bet you didn’t loose your virginity more than a year ago.”

“I’m twenty, and I had my first cock at eighteen,” she muttered, coming back in close to me again, resting her arms on my shoulders again, this time placing her head directly next to mine as she looked at the computer in front of me.

“Eh, off by a year,” I said.

“And I had my first pussy at fifteen,” she whispered into my ear.

I went rock still. She sensed my surprise, and decided to capitalize on it. “Yeah,” she whispered again, running one hand down my bare chest. “She wasn’t anyone famous, just a girlfriend who wanted to experiment a bit one night. I got her to undress, then fingered her until she came.”

I was rock hard now, as Leelee circled one of my nipples with her fingers, lazily moving across my skin while whispering in my ear.

“The next time I saw her, a few weeks later, I took her cherry with the dildo I’d been using to get myself off with while on the set.” She leaned in even closer and licked my ear. My cock was so hard at that point, I feared it would rip my boxers to escape into the air.

“Am I turning you on?” she asked, her other hand sliding across the hair on my head.

“Maybe,” I said, trying hard to sound calm. “Then again, I’m usually turned on when writing sex scenes.”

She stood up behind me and spun me around on the chair, so I was facing her. She had undone the tie in her shirt, allowing it to fall to her sides. It still covered her breasts, but left a clear run of flesh between them that ran from her neck to her waist. I was mesmerized.

“Maybe?” she said, sounding disappointed. She reached down and undid the button on her pants, allowing them to fall to her feet. She wore simple white, cotton panties that looked like they were almost a size too small for her. The outline of her cunt lips was clearly visible, and I instantly wanted to sink my manhood deep into her.

“Maybe,” I croaked in response. She shook her head, allowing her hair to flow behind her. Stepping forward, she straddled my legs and sat in my lap. With only the fabric of our underwear between my rod and her slit, it was all I could do to not jump her bones right there.

“Maybe I want you to be turned on,” she whispered as she leaned in and kissed me again. I felt the hardness of her nipples through her shirt on my bare chest as she kissed me, and I knew she was as aroused as I was.

But the kiss brought me screaming back to reality for a second. It was the same rehearsed kiss she’d used on me the other day. The same combo of Rose and Rachael, with the exact same amount of “rehearsed” feeling to it.

As the kiss broke, she looked into my eyes, and whispered again. “Fuck me,” she said, her voice echoing in my brain. “Fuck me like you did Rose. Like you’ll do Rachael later. Fuck me. Now!”

My cock was literally less than a centimeter from her snatch. Her breasts were barely hidden from view. Her eyes were pleading with me to fuck her silly.

And somehow, I managed to resist.

I gave her a gentle shove that ended up depositing her on the floor when she slid off my legs. She landed with a thud, her shirt falling open enough to expose one of the nipples I had been lusting after since I first met her. Leelee Sobieski lay practically naked at my feet, begging me to have sex with her, and I was turning her down.

“Don’t you have a lunch date to get to?” I said, getting up and moving away from her.

She looked after me like I was some kind of maniac.

“Excuse me? I’m sitting here, waiting for you to fuck me! Get your prick over here and do me!”

“No, Leelee,” I said, turning towards her, seeing that she had moved onto her hands and knees now. “No. I won’t fuck you. I won’t make love to you, and I won’t have sex with you. My penis will not enter you ANYWHERE. And do you know why?”

“Because you’re in love with Rachael,” she said, her eyes filled with understanding.

“Yes, I’m in love with Rachael, but that’s not why you and I won’t be having sex. I’m not going to fuck you because you clearly want me to. It’s not because you’re attracted to me, or because you’re horny – lord knows you’re both of those. But you want to fuck me just to screw with my head, and to get me to screw up what I’ve got with Rachael.”

Leelee’s eyes had gone wide now, as she realized I had seen through her little charade.

“You’re a great actress, Leelee, and I’d be willing to bet you’re a pretty good friend. But I’m not out to hurt Rachael, and she doesn’t need you to protect her from me.”

“Maybe not,” Leelee said, standing up and buttoning up her shirt now. It occurred to me only then that perhaps she HAD planned on meeting me in the room, and changed her shirt so as to better seduce me.

It had almost worked, too. My penis was still harder than it had been in days, and the thought of sliding it into her snatch made me weak in the knees.

I watched Leelee get dressed in silence, and then saw her out the door. As I closed it behind her, I realized that Rachael and I weren’t going to make it to the clubs that night – I was going to be burying myself into her the instant she walked through that door, ready or not.

* * *

Rachael and I had engaged in anal sex on a handful of occasions, rarely more than once per visit. She enjoyed it, I enjoyed it, but we both found it a bit tiring. Plus, I’ve always enjoyed looking at what I’m fucking, and seeing the back of Rachael’s head instead of her beautiful face wasn’t quite as erotic in my mind.

That night, though, we had a marathon anal sex session. Two hours, one full bottle of lube, and lots of tight, slow strokes in and out of her behind made for a blissful evening.

“Harder!” Rachael cried as I stuffed my cock as deep into her rear as it would go. “Oh, god, you feel too good! HARDER!”

I slammed my dick into her one more time, suddenly reaching my third climax of the night, emptying another load into her ass. Rachael cooed as I unloaded, savoring the feeling of my hot cum inside her, fingering her clit as we collapsed on the bed, spent.

“Wow,” she said as I pulled out a minute or two later. “You’re awfully horny today. What’s got you all riled up?”

“You,” I said between heavy breaths. “That hot little ass of yours.”

“I’ll be lucky if I can sit down tomorrow,” she joked. I smiled and rolled on to my back. She was still looking at me. “That’s not all it is, though, is it?” she asked.

“Huh?” I asked, pretending not to understand.

“Something else has got you all hot and bothered. Not just me.”

I sighed, knowing there was no getting out of this – at least, not for another four or five minutes while my cock reloaded.

“Leelee stopped by earlier,” I said.

“I know. You told me she returned my book.”

“That wasn’t all she did,” I said.

“You fucked her?” Rachael asked.

“No, but she wanted me to.”

“Why didn’t you?” Rachael asked, rolling over to lay one hand on my chest. Curled up next to me, I felt life returning to my cock just a bit faster.

“Because she didn’t want me just for sex. She wanted to get between us.”

“Are you sure?” Rachael asked. “‘Cause you know I’ve slept with her.”

I blinked in surprise. “You have? You and Leelee?”

“Yeah,” Rachael said. “You’re all right with that, right?” she asked.

“I thought you two were just friends,” I said, realizing how lame I sounded.

“We are. We just did it twice – once with our fingers, once with a dildo.”

Something about that description clicked in my head. “Had she ever been with another woman before?”

“Nope,” Rachael said, confidently. In fact, she seemed a little smug about it. “I’d told her about how I was Bi, and she wanted to experiment a bit one night. I got her to undress, then fingered her until she came. The next time I saw her, a few weeks later, I took her cherry with the dildo you gave me last Christmas to use on the set.”

My eyes were wide open. The tale Rachael had just told me echoed the one Leelee had used earlier. “Did she tell you if she’d ever been with a man?”

“Yeah, she had,” Rachael said, getting up on one shoulder so she could better look at me now. “When she was eighteen, she let one of her guy friends take her virginity, simply because she didn’t want to be a virgin anymore. At least, that’s what she told me.”

“She lied to me,” I said, in mild shock. “She said she had her first girl at fifteen. And she never mentioned you at all.”

“Never mentioned me at all?” Rachael said, sounding both amused and insulted at the same time. “I’ll have to slap that bitch hard the next time I see her.”

“Why would she lie to me?” I wondered aloud.

“Why does any girl lie to a guy?” Rachael asked, kissing one of my nipples. I was rapidly recovering from my depleted state, and would be ready to go any moment now.

“Because she hates him?” I asked.

“No, silly,” Rachael said, her hand slowly sliding down my stomach. “A girl lies to a guy for the same reason a guy will lie to a girl. She wants to impress him.”

“Why would Leelee want to impress me?” I asked, taking Rachael’s hand in my own, and gently running over her fingers with my own.

“Why would you try to impress her?” Rachael asked, her eyes aglow with mischief.

“To fuck her?” I asked.

“To fuck her,” Rachael said, pulling her hand away and resting it on my reborn penis, ready to stroke at the slightest word from me.

“You’re telling me that Leelee Sobieski, who’s been giving me a hard time since she met me naked two days ago, secretly wants to fuck my brains out?”

“Not so secretly, from the sounds of it,” Rachael said, giving my cock a little tug to get my attention. “I know Leelee. She’s usually a lot more polite with people than she’s been to you. She’s also known for going out and getting what she wants, when she feels the need. Next time you two are alone, you should come on to her, and see how she takes it.”

“You mean turn the tables on her?” I asked, trying very hard to ignore the signals my little soldier was reporting to me as Rachael’s hand slid up and down it.

“What’s the worst that could happen?” Rachael said, starting to kiss my chest. “She turns you down?”

“I guess so,” I said as she continued to kiss down towards my stomach.

“And the best thing that could happen is that you two become lovers, and I can enjoy both of you at once.”

“Greedy,” I said, a twinkle in my eye. I saw the same look mirrored in her face, just seconds before she went down on my rod, starting in on another of her famous blowjobs.

But even as I got ready to fuck Rachael Leigh Cook again, my mind was wandering to what might happen the next time I saw Leelee Sobieski.

* * *

The next time I saw Leelee turned out to be the very next morning. Rachael was out jogging, her lust for me abated by her lust for exercise, and I was too attached to the bed to get up and go out with her. Instead, I slept for another fifteen, twenty minutes or so, and then took a LONG shower, the hot water steaming some life back into me.

Exiting the shower, wearing only a towel around my waist, I was somehow less than surprised to find Leelee bent over my laptop, looking at something online. She wore a short, white skirt that emphasized her long, gorgeous legs, and a tan tank top that almost seemed too informal to match the skirt it was paired with. Her hair was back in a ponytail that left her shoulders bare. With such an array of visual flesh from Leelee’s backside, I found my arousal starting to stir.

She seemed more than intent upon reading whatever it was she was looking at, and for a heartbeat or two, I thought of sneaking up behind her, and just taking her then and there, thrusting myself into her folds before she had a chance to resist. Certainly, Leelee was more than attractive enough for me to want to fuck her good and hard, but her attitude towards me over the last few days gave me pause.

Suddenly, any thoughts of my own actions were put to rest, as Leelee spoke up, not moving at all from her position hovering over the screen.

“About time,” she said. “I thought you’d never get out of that shower.”

“And I didn’t expect to see you ever again,” I countered easily. After my talk with Rachael, I felt like I had a better hold on what Leelee might do. And, if my brain would work fast enough, I might even be able to fight fire with fire.

“Guess you’re just lucky then, huh,” she said, still not moving.

“Is that why you’re here?” I asked, casually walking up behind her. “To get ‘lucky’ while Rachael’s out for a jog?”

“Hardly,” Leelee snorted back.

“Of course,” I said, trying to keep the sarcasm from my voice. “If you wanted to fuck me, all you ever had to do was ask Rachael to set up a threesome. She just loves getting two of her lovers together in one bed.”

That got her attention, and for the first time that morning, Leelee twisted her head about to look at me as I slowly approached her from behind.

“She told you, didn’t she?” Leelee asked.

“About you and her? Oh yes. In fact, she mentioned you were a lesbian virgin when she first slept with you.”

Leelee turned back towards her computer, but still responded. “You know what, you’ve got me. I lied to you, just to see if I could get in your pants. What’re you going to do about it now?”

“That depends,” I said, sliding up directly behind her, close enough for her to know I was there, but without actually touching her – yet.

“Depends on what?” she asked, her body stiffening slightly.

“On if you still want to get into my pants or not,” I said, my voice barely more than a whisper into her left ear.

She didn’t move, but her breathing increase audibly, becoming more ragged and faster. I was about to entice her more when I glanced down at the screen of the computer.

She was on the CSSA search page, her own name up with the list of stories about her beneath them. I felt my eyes go wide, and my jaw slacken, and tried desperately to cover up my surprise by staying behind her.

“So, you caught me,” she whispered, her voice so slight, I almost didn’t hear her. I didn’t know quite how to respond, so I remained quiet.

“No comments on finding me reading sex stories about myself?” Leelee asked. “No jokes about the ice queen melting a little? No snide remarks about the Hollywood Bitch finally getting in touch with her sexual side?”

I shook my head. “Why would I say that – you were practically begging me to fuck you yesterday.”

“And I’ll be practically begging you to fuck me again today,” Leelee whispered. “But this time, it’ll be because I really need a good fucking.”

I let the towel around me drop to the floor and reached out to place my hands on her hips. “I’ll give you that good fucking – on one condition.”

“Anything,” she whispered, still not turning around to look at me.

“From now on, you respect me and my relationship with Rachael. No more trying to get between us.”

“No more,” she whispered. “Is that it?”

I reached down and pulled up her skirt. Not surprisingly, I found no panties there. Placing my raging hard on at the entrance to her pussy, I leaned in close to her left ear again.

“That’s all,” I whispered, before pushing myself deep into Leelee’s snatch.

Leelee Sobieski was no virgin. But she was tighter than my Rachael by a noticeable amount. I’d like to think that I was the one to loosen Rachael up, but at that moment, I wasn’t too worried about it. I was far more concerned in widening Leelee out a bit.

We fucked right there, standing before my computer, with her slightly bent over the chair while I took her from behind. We never kissed, and aside from my hands on her waist or shoulders, we never touched. No thoughts of exchanging kisses entered my mind, and I would seriously doubt they entered hers, either. We weren’t making love in any sense of the word other than the fact that my dick was buried to the hilt inside her. This was fucking, pure and simple, as I drove myself in and out of her faster and harder with each passing second.

No words were said between us, though we both moaned in pleasure more than once throughout the session. For her part, Leelee did little more than moan and massage her breasts through her shirt, as one hand lay on the table, holding her up the whole time we were going at it. Her head rolled from side to side a bit and her breathing came quite rapidly at times, but she made no move to change positions, or to engage me in any effort to try anything else. She wanted me taking her from behind, and I was more than willing to do so.

For several minutes we just fucked like that, standing before a table, her skirt up around her waist, me completely naked. I realized, much later, that the largest window in the place was almost directly across from where we stood, and anyone with half a mind and a place across the way could’ve seen us going at it like animals. I’m certain, though, that Leelee knew all about it, and probably felt that the extra voyeurism added to the eroticness of the moment.

And then, I began to feel the first stirrings of my approaching climax. Holding it back, I continued to pound myself into Leelee’s wet folds, hoping she would get off before I lost control. Then, I remembered the way she’d treated me over the last few days – the insults, the snide remarks, the blatant efforts to break me and Rachael up by sleeping with me – all that came flooding back, and I decided to forget about her pleasure. I was going to blow my load as deep into her as I could, and if she didn’t get off, it was no skin off my nose.

Leelee, however, took the decision out of my hands before I could act on it, for the instant my vengeful decision fermented in my brain, she reached the peak of her own lusts, and climaxed right there. To her credit, she didn’t fall over or pass out, or anything like that. She did clamp down hard with her legs, and dropped the hand she’d been using to manipulate her breasts to the table for added support. But other than that, she simply closed her eyes, gasped loudly, and came all over my cock.

And the instant I felt her stiffen up and hit her plateau, my balls exploded, and I joined her in climax.

Which, of course, was the exact second Rachael returned from her jog, opening the door to see me shooting my load deep into Leelee Sobieski as I fucked her from behind.

Any other woman in the world (with the possible exception of Rose McGowan), would’ve gotten VERY upset and returning to her own apartment to find her boyfriend fucking one of her best friends and occasional lesbian lover. Rachael, though, smiled a huge smile and clapped with joy.

I, of course, saw none of that, as my orgasm took my knees out from beneath me, and I tumbled to the floor behind Leelee, who remained standing the whole time.

* * *

The tone of my vacation change drastically after that first fuck session with Leelee. Where as before my whole time had been based around Rachael’s schedule and desires, I now found myself with almost a part time job working for Leelee. Though, to be fair, I’d be hard pressed to call sliding my cock in and out of Leelee Sobieski twice a day “work.”

It wasn’t, however, the start of a new relationship. I simply tended to Leelee’s sexual needs when Rachael had no time for me. Leelee appeared at Rachael’s door twice a day – once when Rachael would go out jogging, and again, later in the evening, while Rachael would be on the phone with her agent, or her mother, depending on who she felt more like talking too after dinner. I tried very hard not to think about Rachael talking with her mother while I was buried hilt deep in Leelee’s snatch in the other room.

After that first fuck, Leelee and I became a little freer with each other during sex, but it was far from romantic, under any sense of the word. We touched each other now, and we’d both be naked in bed, but kissing was limited to my lips on her breasts, and her lips on my neck. Her hands never touched me anywhere but on my back, when she’d wrapped them around me to pull me deeper into her, though she encouraged me to use my hands to explore her body.

There was still very little love lost between Leelee Sobieski and me.

Rachael and I still made love like there was no tomorrow, frequently after Leelee left for the evening. Despite my refusal to use it after Rose had forced it down my throat months before, Viagra became a tool for me, as it kept me hard after finishing with Leelee and moved on to the far more enjoyable times with Rachael. Still, I was far from fond of the stuff, and swore to never use it again after I returned home at the end of the week.

Rose, unfortunately, didn’t return at all while I was there, and my only contact with her at all was a rather forced phone sex threesome between her, Rachael, and myself one night a few hours after Leelee left. Rose had barely been into it, running late for a date with someone – guy or girl, I never learned – across town. Rachael, though, had insisted that Rose and I get off together, and stayed in bed with me, stroking my cock and doing all the nasty things Rose told her to do.

The more time I spend with Rose McGowan, the more I think KMB’s interpretation of her in “The Harem” is accurate.

It wasn’t until my last night with Rachael that things between Leelee and me came to a head, and when they did, I knew I was in trouble.

I was lying in bed, breathing hard, after having reached my limit while fucking Leelee, when she turned towards me.

“Am I a good lover?” she asked me.

I blinked hard at her, not understanding what she meant.

“Huh?” I asked, feeling instantly stupid.

“Am I a good lover?” she asked again, turning her whole body towards me. For the first time in more than a week, I allowed my eyes to really take in her body. Long and sensuous, Leelee Sobieski was a classic beauty in just about every sense of the word. Lying naked before me, I felt my cock stiffen again.

There was no denying the absolute sexiness of Leelee Sobieski, and I certainly wouldn’t deny her prowess as a lover. I’d never once failed to get off inside her, and despite how I felt about her personally, I’d never regret doing her.

“You’re a great fuck,” I said, and instantly regretted it.

“Bastard,” she said, turning away from me. “That’s all I ever was to you, wasn’t I?”

“Uh, that’s all you ever wanted from me, remember?” I said, suddenly wondering where this was all coming from.

“Yeah, I know,” She said, still not turning back to me. “Still, I had hoped you’d develop some feelings for me.”

That stopped me for a moment, as I wondered, just briefly, if I HAD developed any feelings for Leelee. I loved Rachael, I knew that much, and I was quite fond of Rose. But my relationship with Leelee was different than either one of those. Rachael and I had fallen in love. Rose and I were fuck buddies who enjoyed each other’s company whenever we could.

But Leelee and I hadn’t even tried to do anything but fuck. And, despite my best interests, I actually felt sorry about that.

“Listen, I’m sorry you and I haven’t gotten to know each other too well over the last week or so,” I said, putting my hand on her shoulder. “Maybe the next time I’m in town, we can try a little harder to get to become more than just sex toys for each other.”

She turned back towards me, looking me right in the eye. I knew she was trying to tell if I was serious or not. I held my place and didn’t move, hoping she’d realize I was honest, and apparently, she did.

“Agreed,” she said, smiling. “Now, tell me, am I a good lover or not?”

“We’ve never made love,” I pointed out.

“Then maybe we should,” she said, smiling.

The next thing I knew, Leelee Sobieski had her lips on mine, and for the first time since we’d started fucking each other, we were kissing. I’ve always been partial to Rachael’s kisses – perhaps because of my feelings for her – but that first kiss with Leelee took my breath away. It started off soft, and subtle, a mere pressing of lips together. Then, as I lay there, wrapping my arms around here, I felt it grow more passionate, more feeling flying into it as I pulled her on top of me. I felt her lips part, and soon our tongues were meshing together, and I lost all track of time.

I resurfaced from blissful unawareness some time later, Leelee impaled on my cock as she gently rode me, her lips and mine still locked together, and her hands were playing with my hair. We had been making love for a while, gently enjoying each other’s bodies instead of using each other to get off. I found that I loved the feel of her breasts in my hands. She discovered that I was a bit ticklish around the sides of my stomach. We both came slowly, easily, my seed filling her for the second time that night.

And then, just as Leelee was sliding off my body, I felt another pair of hands on me, and I turned to see a very naked Rachael Leigh Cook smiling down at me.

“Hey, lover,” she said, reaching down and taking my cock in hand. “Ready to switch dance partners?”

“Oh yeah,” I said, moving my arms so as to bring her in reach.

Suddenly, she reached out and slapped my hands away. “Not you, silly. I was talking to Leelee.”

I looked over at Leelee, shocked to see her smiling wickedly at Rachael.

“How about we mix things up a bit,” Leelee said. “I’d hate to leave our stud here without something new to write about.”

Rachael smiled, and I knew instantly that whatever was heading my way, it was destined to involve the three of us getting it on all at once.

And, of course, I was happy to oblige.

Rachael squatted over my erect cock and slid herself down on top of me, taking the place that Leelee had held just recently. She worked herself onto me for several seconds, my member thrilling at the familiar folds of her crotch. I had fucked Rachael so often that I knew every inch of her pussy from memory, and my dick was very happy to be home.

Leelee, though, wasn’t going to be left out. She moved over and squatted over my face, her body turned to face Rachael. I knew at once what my job would be while she and Rachael made out on top of me.

And I took to my job right away. While Rachael Leigh Cook and Leelee Sobieski made out like experienced lesbian porno stars, Rachael rode my cock and Leelee rode my tongue. It was the perfect set up for a threesome. I only wished that Rose McGowan had been there to make it the perfect foursome. Though, to be honest, how Rose would’ve used me to get off while Rachael and Leelee were in position I couldn’t possibly fathom.

I wish that I could say that all three of us came at once, but it wasn’t meant to be. Leelee came first, her girl cum coating my mouth and chin as she climaxed all over my face. I hit my peak for the third time that night as Leelee slid off of me and collapsed on the bed to my side. My cock spasmed and shot a load into Rachael, who, being the last of us to join the party, was ready to go for a while longer.

Unfortunately, I wasn’t up to it, and had to settle for watching Leelee get Rachael off with her fingers while my poor abused manhood recovered from the evening’s adventures. It wasn’t that I was having trouble getting it up – far from it, thanks to a little blue pill. No, this time, I was just warn out, my little man sore from the action and in need of a breather.

Rachael and Leelee were far from done, though, and as I watched, I marveled at just how compelling lesbian sex can be to watch. Their lithe forms, covered in sweat and cum moved about far more gracefully than I ever could dream of doing, and the fluidity of their actions left no doubt as to their intentions. They made love, as Leelee and I had earlier, and Rachael and I had done many a time before that day.

Their bodies merged together in a fashion that no man could ever hope to achieve with a woman. The fact that there was no penis between them to hold them in one static place allowed Rachael and Leelee to move about not only the bed, but also each other’s bodies. Rachael’s hand would swoop down over Leelee’s crotch, then slide up to her breasts, all while maintaining a light and erotic touch. At the same time, Leelee’s mouth moved from Rachael’s neck down to her beautiful breasts, and the valley between them, lavishing licks and kisses as she went.

I watched this mingling for several long minutes, feeling my manhood struggling to return to me. It was like watching some Sapphic dance, conducted on the bed not two feet away from me, as these two incredibly sexy actresses coordinated their moves to continually increase the pleasure they both felt. Rachael used her fingers, Leelee used her mouth. Rachael would stroke and caress, Leelee would kiss and lick.

And suddenly, the tempo changed.

Before my eyes, the two girls became a writhing mass as each shoved a few fingers into the other’s pussy, and started stroking as hard as she could. Their remaining hands gripped and fondled each other almost faster than the eye could see, trying to be on every nerve of each other’s bodies at once. At the same time, their lips were locked in the single most lust filled kiss I’ve ever seen.

I stared slack-jawed for several long minutes as Rachael Leigh Cook and Leelee Sobieski literally finger fucked each other raw. Rachael came first, shuddering and nearly falling off the bed. Leelee managed to hang on to her, pulling her away from the edge, but continued to stroke, despite Rachael having hit her plateau. Rachael didn’t stop, either, her fingers slow not a bit as she furiously rammed them in and out of Leelee’s snatch.

Not ten seconds later, Leelee climaxed, her limbs going weak, and her eyes rolling up into the back of her head. Her fingers nearly stopped, but she recovered the instant Rachael pressed a thumb against her clit, and before I could begin to believe it, the two were working themselves forward again.

Like a sexualized wrestling match, the two lithe young women continued to stroke and kiss and fondle each other until they both came again, Leelee first this time, Rachael second. And yet, still they didn’t stop. I was becoming jealous of just how often a woman could climax in a day when they both hit their third orgasms of that particular pairing at the same time, and simply fainted to the bed, their bodies still entwined.

* * *

“You sure you don’t want to fuck one more time?” Leelee asked the next morning. “I mean, I could get you off in five minutes, and you wouldn’t be too late for your flight.”

“Sorry, Lee,” I replied, hefting my overnight bag over my shoulder and giving her a quick kiss on the cheek. “The last blow job Rachael gave me has drained the tank dry.”

“Too bad. Guess I’ll just have to do her when she gets back,” Leelee sighed.

I snorted, knowing full well that Rachael would be jumping Leelee’s bones the instant she walked through the door. Rachael had always been a bit of a sex addict, and now that Leelee was sure she wasn’t going to get hurt fooling around with me, I knew the lovely Miss Sobieski would be helping my celebrity girlfriend become even more addicted to orgasms than she already was.

“See yah, babe,” I said, heading out to the cab waiting for Rachael and me.

“Get your cock back here as soon as you can!” Leelee hollered after me. Rachael laughed at that as we hopped in the cab and headed out to LAX. Making out most of the way there, I marveled at how much Rachael had really come to mean to me. Oh, sure, fucking Rose and Leelee added some spice, and I knew for a fact she’d done Katie Holmes a couple of times, experimenting with her sexuality even more. But in the end of the day, I was the one Rachael loved, and that was good enough for me.

Besides, why should I complain if my girlfriend likes to fuck famous women? I can’t blame her for something I love just as much as she does, can I?

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