Win a Night with Reese Witherspoon

Starring: Reese Witherspoon

Tags: MF, Oral, Creampie

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

As I approached the restaurant, I was nervous about what to expect. Reese Witherspoon was one of my biggest celebrity crushes and I was about to spend an entire night with her.

I had won an online contest where the person who gives the biggest donations wins a date with Reese. Luckily for me, money was never a problem so I made sure that my bid was always the highest. By the time the contest had ended, it was no surprise to me that I had won. But I was still anxious about meeting her.

I opened one of the glass doors to the high-class restaurant and walked up to the counter where I was greeted by a man with a smile. He was wearing a black suit with a white undershirt.

"Hi, I'm here to meet Miss Witherspoon."

"Yes, of course, right this way, sir." I followed the man as he led me to the table where the beautiful blonde sat, dressed in a black tank top, black jeans, and black heels. Her make-up was done perfectly and her blonde hair was nicely brushed behind her head.

"Hi, I'm Mike," I said, reaching my arm out to shake her hand.

"Reese, but I'm guessing you already know that." Her face lit up with a smile as she gripped my hand.

I sat down across from the Legally Blonde star, my leg a bit jittery, showing just how nervous I really was.

"I can't thank you enough for that donation, we really, really appreciate it."

"Oh, it's no problem. Anything to make the world just a small bit better is always good."

"I couldn't agree more."

A waiter, dressed similarly to the man at the front, walked up next to the table, prepared to ask us what we'd like to eat.

I quickly glanced over the menu and decided what I'd like.

"I'll have a steak with a side of broccoli and a glass of red wine, please," I said, handing the waiter my menu.

"Mmmm, that sounds great. I'll have that too." Reese handed her menu to the waiter.

"Your food will be out shortly." The waiter said, walking away from the table.

"Thank you," I said, focusing my gaze back on the pretty woman sitting in front of me.

"Someone's got some manners," Reese said with a giggle, "though that's not a bad thing."

"Yeah, my parents were always on me about manners when I was younger. Holding doors for people, using please and thank you, not swearing in public."

"Sounds like you had good parents."

"Well, most of the time." I smiled as Reese laughed, her hand reaching across the table and landing on top of mine. This sent shivers down my spine. One of the most gorgeous women in the world was currently holding my hand. What a moment to remember.

"I'm the same way with my kids. Though, I'm not the best role model when it comes to not swearing in public. Every now and then one just slips, you know?"

"Of course, it still happens to me now, and I always seem to forget that you're a mother of two. You look like you're hardly 30."

"Awww, he's sweet too. But you don't have to be that nice. I know I don't look 30."

"Ok, maybe you don't look 30, but you're over 40 and you still look incredible. That outfit only makes you look even better."

"Oh, this old thing," Reese pulled the strap of her tank top up, revealing a small hint of cleavage that quickly caught my eye. I could feel my dick start to harden in my pants. "I've had it for years, I'm surprised it still fits."

"Don't say that. You look almost identical to how you looked 20 years ago."

A big grin spread across Reese's face and her cheeks started to turn a bit red.

"Stop it, you're making me blush."

"Hey, I'm just speaking the truth. You sure don't look to me like a mother of two."

"Well, now that you've got your compliments out of the way, tell me about yourself."

I started to tell Reese about my childhood. My parents, my friends, past girlfriends, school, college, my job, and Reese seemed engaged the whole way through. I tried to keep my eyes in line with hers, but every now and then they'd drop down to her cleavage. Lucky for me, she never mentioned seeing them.

Just as I was telling her about my most recent relationship, and we were finishing up our second glasses of wine, a waiter arrived with our entrees.

"Two steaks for the pretty couple," the waiter said, setting the plates down on the table. Neither of us chose to correct the waiter about his assumption of our relationship. We were too busy laughing and having a good time.

"Wow, this looks delicious, thank you," I said to the waiter just before he walked away.

"Ok, ok, so let me see if I've got this right," Reese said, slurring her words, quickly becoming drunker as the night went on. Clearly, she was not used to drinking this much, even if it was just a few glasses of wine. "Your girlfriend, who you'd been with for 6 months, cheated on you with your best friend, in YOUR apartment."

"Yep, sounds just about right," I said, taking a sip from my wine.

"Pardon my language, but she seems like a cunt." My eyes lit up, as we both started to laugh.

"I mean, now I'd agree 100%. But before I found out, I would've never guessed. She was great, pretty, funny, nice, responsible, caring," I considered stopping there, but I knew this would be my only shot of ever getting with Reese, "a lot like you, actually. Or, at least, from what I've learned about you in the last hour."

Reese's face went red again, but this time, a naughty smile crossed her face.

"You really think so?" The blonde said, leaning over the table, her smile growing wider.

"Of course, I was raised to not lie either," I said with a grin, as Reese continued to lean in closer.

Sadly, the moment was cut short when Reese's arm slipped and she knocked over my glass. The wine spilled out, landing on the bottom of my white shirt and all over my crotch. Reese quickly stood up and started apologizing.

"Oh shit, I'm sorry. I'm so sorry. Here," she continued, starting to rub her napkin on my slowly hardening cock.

"It's fine, it's fine," my boner grew bigger and harder by the second.

Reese began to notice and started apologizing, even more, this time with a slight hint of naughtiness in her eyes.

"Oh, wow, um, I-I'm really sorry," she stuttered out, forgetting that she was still wiping my now rock-hard erection. She dropped the napkin from her grasp and covered her eyes (but kept her fingers separated enough so she could still see it).

Lucky for the both of us, we had finished our dinner and were both ready to make our way out. Reese tried to pay for the check, as another form of apology, but I refused, not letting her pay a cent for the night.

Reese grabbed her coat and we headed for the door. As we started slowly walking down the street, she turned to face me.

"You know, up until the accident, I was having a really great time."

"Me too, though, I quite enjoyed the end too," smiles appearing on both our faces.

"I'm sure you did," Reese responded, lightly shoving me.

"What can I say, Reese Witherspoon furiously rubbing my...you know, would be hard not to enjoy."

"How about I make it up to you?" The short actress asked.

"Oh yeah, what did you have in mind?"

"I was thinking I could take you to my hotel room. It's nice and big," her eyes beginning to drift down to my mostly flaccid dick, "and it can get pretty lonely up there, all by myself."

"Uh, yeah, sure, sounds great." Reese grabbed my hand and began to take me to her room.

It took us about 10 minutes to make it to the hotel, and another few to make it up to the room. The hotel employees saw Reese coming and ushered us to a back elevator, so she wouldn't have to deal with any fans or paparazzi. Once the elevator doors closed, Reese was attacking me, her lips pressed right up against mine, her tongue forcing its way into my mouth. When I didn't respond to the kiss, she pulled away, a look of confusion on her face.

"What? I finally gave in to you and you don't like it?"

"No, no, it's nothing like that. Actually, this is like a dream come true."

"So, what is it?"

"I mean, you're married, aren't you? Should we really be doing this?"

"Well, I should tell you that my marriage isn't nearly as great as you'd expect it to be. Jim (her husband) is always sleeping with sluts half his age behind my back, and I'm sick of him being the only one having fun."

There was a pause before she continued.

"Plus, I haven't had sex in years."

The elevator bell dinged as my eyes widened. This was like something out of one of my fantasies.

Reese Witherspoon, a sexy, married MILF, has a cheating husband and has been sexually starved for years.

I knew just what to do. I came at Reese just like she had come at me before, but this time, we were both into it.

We made our way out of the elevator, our lips still locked, as we started undressing each other. Reese unbuttoning my shirt, while I reached for the zipper on her dress. I was the first to finish and watched as the dress slipped down Reese's small, curvy frame.

Reese was now standing in nothing but a lacey red bra, a matching set of panties (that showed off her shapely ass), and her heels.

"You like?" Reese said, spinning in a circle to give me a view of her entire body.

"Fuck yeah I do," I approached her and wrapped my arms around her, pulling her in for another deep kiss. Reese continued to unbutton my shirt, finally able to pull it off as her hands made their way down to my belt. She pulled it off and dropped it to the floor, our lips still locked together, as she began to lower my pants.

"Let's see what my friend's been up to since our previous encounter." Reese yanked down my pants, leaving me standing in just my boxers. She pulled those down as well, her jaw-dropping at the sight of my cock.

"You like?" I asked a grin on my face from being able to ask Reese Witherspoon if she liked my dick.

Reese didn't respond with words, but instead by leaping forward and taking my big cock into her mouth. She was clearly not an inexperienced gal, and this was not her first rodeo. She knew just how to handle a cock, and I was loving every second of it.

"Holy fuck, you're good at this, huh?"

Reese pulled my cock from her mouth to respond.

"Never gotten a complaint before," she said, before getting back to sucking on the tip of my dick.

Reese continued to blow me as I ran my hands through her soft, blonde hair. Moans continued to escape both of our mouths, hers muffled for obvious reasons.

As good as Reese's blowjob skills were, I was getting bored in this position. So, I pulled my cock out of her mouth, a pop sound made as I did. I dropped down to my knees, now at Reese's eye level, and kissed her before she could say a thing.

Our kiss was passionate and hard, our tongues massaging each other as I laid her down on her back. As we continued to kiss, I started to rub my hands over her breasts, playing with her nipples with my fingers. Her moans started to get louder as I led one hand down to her deliciously wet pussy.

Kissing my way down her body, I was met with a neatly trimmed pubic region, one belonging not to an inexperienced 20-year-old, but instead a beautiful 40-year-old. I kissed and licked my way around her lips and rubbed my finger around her clit. Her body began to shiver as I continued playing with Reese's wet snatch. I began lapping at her opening like a thirsty animal, her arms starting to reach out to hold onto anything she could.

Using just my mouth, I was able to give Reese a body-shaking, unforgettable orgasm, one I knew she needed and deserved.

Once she came down from her high, Reese sat up and brought me in for a kiss. This one was less passionate and more loving than our previous kisses. As our lips parted, Reese started to speak.

"That was," still trying to catch her breath, "the most intense...amazing orgasm...I've ever had. Thank you." Her hands rubbing against the sides of my head, her face red and her breathing heavy.

"No problem. I'd gladly do it again." Reese smiled at my comment as she began to kiss my neck, her hand gripping my still hard cock.

"Now...I think it's your turn," Reese said, climbing onto my lap, grinding her hairy cooch on my hard-as-steel member.

She reached behind her back and unclasped her bra and unleashed her perfect breasts on my eyes. She sat up a bit, peeling off her panties, and throwing off her heels, leaving her in nothing but her birthday suit.

As she slowly started to take more and more of me inside her, her mouth became agape, shallow breaths coming out as a result.

"Oh, wow, you're so thick. I've never felt so full before," she cooed, moving her hips back and forth as she was getting closer to bottoming out on my dick.

"I've never felt a pussy so warm and moist before," bringing my finger down to wipe up some of her juices. I brought my finger up to Reese's mouth and she gladly sucked it clean of her liquids.

As Reese's slow, romantic rhythm kept up, I was in absolute heaven.

Reese Witherspoon, the sensationally stunning actress who I'd had a crush on for over a decade, was completely naked, riding me as she told me how much she loved my cock.

As we sat, continuing to make love in the lotus position, I was hoping the night would never end. Having her wrapped in my arms was amazing, the feeling of her cougar pussy hugging my hard penis bringing me closer to orgasm, and her lips kissing their way across my collarbone to my chest.

Wanting to get more intense and passionate with this perfect specimen, I gripped my arms under her plump ass cheeks and stood up, her legs wrapped around my waist.

"Oooooh," she moaned, "I like a man who takes initiative."

"Then you're gonna love me," I responded, throwing our bodies against the wall, starting to pound my cock harder and harder into her eager cunt, Reese's moans filling up the room, like speakers turned up to 11.

Our fucking could probably be heard from two floors down, but we didn't care. We were in our own little world, lost in our sex.

"That's it, baby," Reese shouted, "Fuck me harder! Harder! I want all of your big dick inside of my little fucking pussy."

I spun around and walked Reese and me over to the bed, dropping her on it, keeping my shaft inside of her.

I shoved myself back into her, every inch of my cock now inside of the Oscar winner.

"Mmmm, FUCK! Your dick feels so good! My husband never fucked me like this!"

"Not to be rude, but if your husband isn't having sex with your multiple times a day, he's insane," I complimented her, continuing thrust after thrust into her.

"A gentleman even when he's balls deep inside of me? Now I know you're special."

I smiled as I continued to look Reese in her blue eyes, her blonde hair all messy, her breasts bouncing with every thrust moans coming from her lips, telling me to pound her pussy and to fuck her good.

I could feel myself getting close, and I could sense that Reese was too, so I upped my speed just a bit more, wanting to get us to cum at the same time.

"Shit, babe, you're gonna make me cum again."

"That's the plan," I said, hoping to not pop off too soon.

Today must've been my lucky day because as soon as I'd started shooting rope after rope of cum inside her magnificent pussy, I felt Reese's walls tighten and her arms squeeze the bedsheets as she was brought into her second orgasm of the night.

"HOLY SHIT!" Reese screamed.

"Fuck, I love you, Reese." I moaned, not even realizing what I'd just said.

"I love you too, sweetie. Fill my MILF pussy with your young cum!"

I let out a few grunts as my orgasm came to an end. I plopped down next to Reese, both of us trying to catch our breaths.

"That was..." Reese started.

"Incredible?" I finished, hoping that was what she would say.

"Even better. That was the hardest I've ever cum in my life."

"Always glad to help." We both chuckled at that as we slowly drifted off into a deep, and needed, sleep.

The next morning I awoke to find myself spooning a still nude Reese Witherspoon, my hand resting just above her mound. I tried my best to sit up without waking her.

"Morning, stud," she said with a smile, not bothering to cover up as the sheet dropped, revealing her luscious breasts to the cool morning air.

"Morning," I replied, giving her a quick kiss.

We both stood up and started to redress, a question bouncing around my head, I contemplated whether I should ask it or not.

"Hey, Reese,"

"Yeah?"

"Sorry to ask this, but, uh, what do you think is going to become of this?" I asked, motioning to the two of us.

"Well, I'm actually glad you asked. We both know that I can't just jump and leave my husband. But, I don't want this to be a one-time thing. I loved last night too much for us to just part ways now." I smirked at her comment about the previous night.

There was a pause. Both of us perfecting the next thing we said.

"So," I asked, not sure what to say next.

"So, I think we should make this a regular thing." Reese smiled as she still stood nude, her curvaceous and ravishing nude form still open to the world. She was confident in her body and in her status as a MILF. Not that there was a reason she shouldn't be.

"Really?" I asked, making sure I'd heard her correctly. It would have been horrible to have misheard her.

"Of course. I don't know how I could go on living, knowing that there was a dick out there like yours that could make me feel so good."

She walked over and gave me a kiss on the cheek, before proceeding to go wash up in the bathroom.

"I'm gonna go shower." She said, disappearing into the bathroom.

As I smiled to myself, Reese peaked out the doorway.

"You coming?" She asked, I nodded and followed her cute ass into the shower.