Breaking Into The Mainstream Ch. 04

Starring: Leslie Mann & Kate Mara

Tags: MF, Cons, Oral, Facial

DISCLAIMER: This story did not happen and is complete fiction. Not all facts will be 100% true to real life.

As I was enjoying a good night's rest, I was suddenly awoken by my cell phone ringing. When I was on my vacation, I was happy to be able to keep it on silent the whole time and not miss a single call. But being back in L.A. meant that I had to keep it on in case anyone needed to get a hold of me.

I picked up my phone and, after my eyes adjusted to its brightness, I could see it was my agent Jen calling me. I could also see that the time was just a few minutes past 10.

"You better have a good reason for waking me up this early."

"Is a beautiful actress willing to do anything for a role in your next film good enough?"

Now, this grabbed my attention.

I sat up fully and now felt completely awake.

"Depends on the actress."

"Kate Mara, I assume you know her."

"Yeah, I know her. She's really that desperate to be in my film?"

"I'm pretty fucking good at reading people and I'd say she sounds pretty damn desperate."

Jen and I had always had a very sardonic back-and-forth, but we both knew the other could handle it so it never came to be a problem between the two of us. To be honest, our similar senses of humor are likely the reason we got along so well.

"So, what are we still talking for? Set up a meeting."

"I already did."

That was the last thing Jen said before she hung up. About 30 seconds late, I received a text from her telling me that she'd made a reservation at a restaurant for 7 o'clock tonight. Jen knew I had the day off, and I'd been looking forward to getting to relax a bit after my energy-fueled threeway with the Riverdale starlets, but dinner with Kate Mara sounded better than eating dinner alone.

After putting in my AirPods and putting on some music, I got out of bed and began my morning routine. Since it was getting warmer out now, I opted for a light blue polo shirt, a pair of khaki shorts, and brown sandals. I also grabbed my pair of sunglasses, as it was going to be quite sunny today before I headed out to grab some breakfast.

Unlike most of the Hollywood crowd, I had never been the biggest fan of getting breakfast at Starbucks or Dunkin' Donuts, but would rather go to a diner and get a quality meal. My go-to diner was only a 10-minute drive from my house, so I luckily didn't get there too late to still order breakfast. After the cute waitress had led me to my booth and taken my drink order, I was interrupted by a redhead popping into my booth.

"Hey, you're that director, right?"

"Yeah, I'm Michael, nice to meet you," I said with a smile, and while reaching out my hand.

"My husband just recently got a hold of your film. It was really good," the pretty redhead told me. Once she'd mentioned her husband, I realized how stupid I was for not immediately noticing who I was talking to.

"Thanks, that means a lot coming from someone like you."

"Oh, so you do know who I am."

"Of course, you're one of the finest comedic actresses of the modern era."

Leslie was clearly flattered by my comment as her cheeks quickly became red and she looked down at the table. She didn't have a chance to respond before the cute waitress returned with my coffee and took down my food order. I invited Leslie to eat with me and, after a bit of convincing, she gave her order as well.

"You know, that was really nice of you to say. It's nice to know at least someone appreciates me," she said, once the waitress had left. I smiled at her comment at first, but it began to dawn on me the true meaning of it as we continued to talk. We traded stories about our time in the business as we waited for the food to arrive. Once it had, we began to talk more about our personal lives, which brought my mind back to her comment a few minutes ago.

"You said something before about 'at least someone appreciating you', what did you mean by that?" I inquired, as we both finished up what was left on our plates.

"Oh, that, that was nothing," she said, brushing her hair behind her ear and breaking eye contact with me. It was obvious that it wasn't nothing, so I gave her a knowing look until she finally explained.

"Alright, so maybe it wasn't nothing."

"Clearly."

"It's just...I feel like outside of Judd's movies, I'm rarely the "go-to actress" for comedies. Not only that, I rarely get the chance to do anything outside of comedy. Now, don't get me wrong, I love doing comedy, and I love being in Judd's films, but sometimes I wonder..."

"What it'd be like to do something different," I finished, before taking a sip from my coffee.

"Exactly, I want to do something new, but I rarely get cast as it is, and most of the time it's in my husband's films. And I only get those by fuc-" Leslie stopped before she said too much, but my brain already knew what she was gonna say.

"Well, if it's any consolation, I'll consider you for a lead role in any of my future projects."

"No, you don't have to do that. I can get roles on my-"

"Leslie," I spoke, grabbing her hands and holding them in mine atop the table, "I've seen your work. I know how immensely talented you are and I know that you deserve great leading roles. I want to be the director to get you your first Golden Globe, or even your first Oscar. I promise, every leading role that I think you could play, will be offered to you first, you have my word."

It didn't take long after my speech for Leslie to cry, though it was a good kind of cry. I could tell she didn't receive this kind of praise a lot, which was a shame because I meant every word I said. Taking her beauty out of the equation, Leslie had what it took to be a leading lady. She could be comedic and dramatic, both within the same film and within the same scene. She could actually act, but her constantly being cast in studio comedies kept that fact hidden from the public and, even worse, directors.

"Tha-Thank you, Michael," she said between sniffles, "that's really sweet of you." She took a final sip from her tea before she got up and began walking off. She was halfway to the door when she turned around and gave me a questioning look.

"You coming?"

Now it was my turn to give a bit of a confused look, as I left a tip on the table and followed Leslie out of the diner. I followed her to her car, where she opened the passenger-side door for me to get in. As she pulled out of the parking lot, I finally asked the question that had been on my mind.

"So, where are you taking me?"

"Somewhere we can fuck without being disturbed."

Her reply shocked me and sent several hundred different thoughts through my head.

"Wait, what, we-we can't do that?"

"Why not?"

"'Why not'?! You're married!"

"Yes, but, this is Hollywood. If you can find a couple where one partner isn't sleeping with someone else, I'll give you a million dollars." I had always heard rumors that Hollywood was like this, but I never had a solid piece of evidence to support it. Now, in just a few seconds, I had hard evidence that this was very, very true. I sat in a state of both confusion and excitement. Ever since I'd seen Knocked Up, I had dreamed of fucking the sexy little redhead and now today I'd finally have the chance. But Leslie was a wife and a mother, and I didn't want to be the one to ruin her family.

"I can tell by the look on your face you're questioning what you should do," Leslie spoke, interrupting my inner thoughts, "now, I'm not gonna force you to do anything. If you want to have sex, I'd love to, but if you don't, let me know so I don't drive all the way home for nothing."

"Home? We're gonna have sex at your house???"

"Yeah, is that a problem?"

"I would assume so, as it's also the place where your husband and kids live."

"Both of the kids are at school and Judd is gone working on his next project. We'd have the house all to ourselves, but you've got to let me know right now if you want to go through with this or not."

I took another second to think it over. This was definitely not a good thing to do, but I knew if I didn't go through with it, I'd be pissed at myself for the rest of my life.

"Yeah, let's do it," I said, smiling, the feelings of confusion and anxiety fading away, the only thought in my mind being the thought of plowing the thin MILF on the bed she shared with her husband.

"Good, cause I've been in need of a good, hard fucking and I think you're gonna be able to give that to me."

Leslie and I, both anticipating the arrival at her house, sat in silence for the rest of the car ride until we pulled into the driveway of a very expensive-looking house. It was far nicer than where I lived, though my place was far from a dump (apologies for the brag).

We both stepped out of the car and Leslie led me inside through the large front door. I politely removed my shoes, while Leslie did the same as I then followed her into the kitchen.

"So," she started, leaning up against the long marble countertop, "where would you like to start?"

I didn't bother answering her question, at least not verbally, as I grabbed the short redhead in my arms and pulled her towards me, bringing her lips to mine for a passionate kiss. Neither of us moved our tongue, but simply enjoyed the taste of each other on our respective sets of lips. I used this opportunity to get a feel for Leslie's body. I ran my hands down her sides, across her hips, and around to her firm ass. It wasn't as large as Krysten's or even Linda's but it was still nice and pert, especially for a thin-framed woman like Leslie.

As we separated our lips, I reached for the top button on Leslie's shirt and began to undress her. She simply watched me do it with a smile that was both cute and naughty. Once the last button had been undone, I slipped the shirt off her shoulders, leaving her in a form-fitting white tank top. She quickly made do with removing it, leaving her in just her pants. With her shirt and tank top removed, I got the chance to admire her chest and stomach.

For a mother of two, she sure didn't seem like it. Her body was in better shape than most women half her age, which was both very impressive and very arousing. Her stomach was flat and smooth. Her breasts were small and perky, topped off by tiny, light brown nipples. I brought my right hand up to caress her left breast before dropping my head to take her right nipple into my mouth. I sucked on the small, brown nub and got it hard before moving over to her left breast and doing the same. Leslie began to let out sweet, soft coos as I pleasured her tits.

"Mmmm, it feels so nice having you take your time. Judd always just rushes into things and rarely do I ever get to get off."

"Well, the pleasure's all mine," I said, taking a quick break from pleasuring her chest, before rightfully resuming my position, tasting her tiny nipples. I took one of her tiny nubs between my teeth and gave it a light tug and pull, causing Leslie to moan a bit lower and grasp my hair with both hands.

"I believe the pleasure is definitely all mine," she joked, giggling as I lightly tugged on the brown stud. After treating her other nipple to the same mix of pain and pleasure, I detached from it and began kissing my way further down Leslie's body. I planted soft, loving kisses across her abdomen, holding her by the waist as I got down on my knees. I unbuttoned her pants and slid the zipper down all the way before being stopped by Leslie before I could pull her pants down her legs.

"Sorry, I just..."

I turned my gaze from Leslie's waist up to her beautiful blue eyes, seeing that she was looking down, but away from me. I grabbed her hand and gave her a concerned look as she continued.

"I just remembered, I haven't shaved down there in a bit. Judd never goes down on me so I usually don't bother trimming down there until it gets very long. I hope you don't mind."

I chuckled to myself, glad that it wasn't about something more serious.

"Leslie," I said, rolling her panties down her leg, exposing her moist, pink lips to me, "I don't mind one bit." I began planting soft kisses around the perimeter of her mound. I circled her pussy, inching closer and closer with every next kiss but not getting close enough to come into contact with her sex yet. I wanted to teas Leslie for a bit so I could work her up to a powerful, mind-shattering orgasm. With each kiss, I could feel Leslie's pubes tickling my skin. Sure, the three women I'd slept with the previous day had all been mostly shaven, but a hairy pussy wasn't any less beautiful than a shaved one. I let Leslie know this by dragging my tongue across her skin, the soft red hairs grazing across my tastebuds. I pulled my mouth from Leslie's body for a quick second, looking up at her and giving her a knowing smirk before leaning back in and pressing a hard kiss against her button-like clit. A shiver shot through Leslie's body as I did this, prompting her to rest her hands on the counter to keep her still.

"Ohhhh, that feels so nice," she moaned. My actions towards Leslie were arousing her enough to get her to release several moans, which were, in turn, causing me to become aroused. I could feel my erection pressing against the fabric of my boxers, causing a tent in my shorts.

I planted a second kiss on her clit and then dragged my tongue down to her opening. I curled my tongue and entered her wet entrance, using my thumbs to spread her lips apart. I brushed her lips with my fingers as I tongue-fucked the pretty redhead's twat. Leslie sighed as I continued to toy with her tasty box, working her slowly and precisely. I continued moving my tongue in and out of her for another minute or so before removing it completely and replacing it with one of my fingers. With my fingers taking over for my tongue, I could now use it to focus on her exposed clit. I pressed my tongue against the small button, causing a sharp groan to escape Leslie's lips.

"Mmmm, shit, that's it. Right there, sweetie, yes!"

Hearing how much she was enjoying the attack I was doing on her womanhood, I decided to add another finger inside of her and increased the pace of my fingering. My fingers were slick with Leslie's juices as I continued moving in and out of her slick opening. I pulled my tongue away from her clit and then pressed my lips against it in a rough kiss. This sent another sensation through Leslie, causing goosebumps to cover her skin. Her legs also began to wobble a bit as I sensed she was getting closer. I increased the tempo of my fingers and the roughness of my kisses to her clit as Leslie's moans became louder and more frequent.

"Ahhh, yes, I'm so close! Please make me cum, baby! I wanna cum so bad!"

Her egging me to get her to come prompted me to use my free hand to reach around her slim waist and do something I knew would push her over the edge. I ran my finger around the ring of her butthole, tickling the skin around her hole without entering her.

"Ohhhh, you naughty boy, you like my ass, don't you?"

I gave her an affirmative grunt, not wanting to stop my assault on her clit to respond.

"Sorry to disappoint you, babe, but my ass is re-"

Leslie stopped what she was saying and let out a high-pitched shriek as I slipped my pointer finger halfway into her butthole, her entire body tightening and convulsing as the orgasmic feeling filled her from head to toe.

"HOLY SHIT! I'M COMING!!"

The redhead MILF's body violently shook as she held onto the counter behind her for dear life, my assault on her sensitive area only slightly stopping as she went through the motions of her orgasm. I removed my fingers from both of her holes and rested them on her waist as I lapped up as much of her tasty juices as I could. Once Leslie had recovered from her orgasm, besides her breathing which was still heavy, I got off of my knees and stood up in front of her. I could see she was struggling to stand up so I took her weight off of her feet and lifted her onto the counter, on which she laid down. I watched as her breasts heaved up and down as she continued to try and catch her breath. I glanced down at the two fingers of mine that had been inside her glistening snatch and brought them to my mouth. I sucked them completely clean of her juices, enjoying the taste of her on my fingers.

"That was...amazing," Leslie said, leaning up on her elbows, her face glowing and her body covered in a sexy sheen of sweat. She lightly rubbed her fingers between her engorged lips, covering them in the juices I had just sucked off my own fingers. When Leslie brought her fingers up, I firmly grabbed a hold of her hand and sucked her fingers clean, which made her smirk. Once I released her fingers, Leslie's eyes moved down my body, landing on my obvious bulge that was painfully pressing against my shorts.

"Seems I'm not the only one who enjoyed that," Leslie said, reaching down and rubbing my fully hard cock through my shorts. I groaned at the feeling of her small hands on my dick.

"Now, let me take care of him as you did me."

Leslie slid off the counter and got onto her knees, as she began unbuttoning my shorts. I pulled off my shirt and tossed it onto the back of a chair behind me. In just the few seconds I'd taken to remove my shirt, Leslie had already dropped my shorts and boxers, revealing my rock-hard cock to the cool air. I kicked the piled-up clothing toward the foot of the chair that held my shirt and quickly removed my socks. Before Leslie could begin stroking me, I gripped her arms and pulled her up, which made her shoot me a quizzical look.

"No reason for you to kneel on the floor when you've got a bed just upstairs."

She smiled at me before turning and running out of the kitchen and up the staircase to her bedroom, giggling the entire time. I immediately followed her, quickly catching up with her in the master bedroom. It was as large as I'd expected, with a huge bed that Leslie was currently laying down on. As I walked up to the foot of the bed, I admired just how sexy Leslie looked. There were beads of sweat along her entire body, which tempted me to plant kisses across her from head to toe. And so I did.

I lifted up her left leg and kissed her ankle, moving up her body at a swift speed, as I was eager to get inside of Leslie's tight body. I moved up her thin leg and up to her thigh, kissing across to her belly button before removing my lips and lifting up her other leg. I repeated the same process, making my way down her leg, across her thigh, and onto her belly button once again. I moved up her body, kissing from her stomach, to her abs, to her breasts, to her neck, before bringing my lips to her own. Her lips tasted so incredibly sweet, I was in complete awe of their taste. As we continued to kiss each other, I could feel my manhood pressing right up against her warm sex. I began to grind my cock between her lips, making sure my tip came into contact with her clit on every thrust.

"Ahhhh, stop teasing me, baby. Go on and fuck me."

I didn't take more than a second to listen to Leslie as I thrust my dick into her tight twat. Her mouth formed an "O" as I slowly moved my meat in and out of her. Her pussy felt so warm and snug, my length felt like it was in Heaven as it penetrated her moist box.

"Fuck, you're filling me up so good."

Leslie's moans got louder and her breathing got heavier as I upped the pace of my thrusts inside of her. I pushed up as far as I could so I could see as much of Leslie's body as possible as I continued fucking the redhaired MILF. Her eyes were shut and her mouth was still agape as I used one hand to reach down and toy her exposed clit.

"Oooohhh, yeah, right there. I'm getting close again, sweetie."

Knowing Leslie was close to her second orgasm, I increased the tempo of my thrusts again, this time violently thrusting into her with wild abandon. Her arms reached behind her head and grasped the edge of the bed, which pushed her chest up, bringing her nipples close to my mouth. I decided to toy with another sensitive part of her body, taking one of her hard nipples into my mouth and sucking on it. I lightly bit down on it, which made Leslie squeal.