Ride ‘Em Cowboy

Starring: Jessica Simpson

Tags: MF, Tit-Fuck, Facial

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

"Fuck, holy shit, baby, you're gonna make me cum again!"

Jessica moaned at the top of her lungs as she viciously rode me. Her large breasts bounced up and down, while her blonde hair flew in and out of her face. This was our third round in the last 24 hours and she was still going buck wild. I couldn't believe this mother of three was able to keep up this pace for so long.

"Come on, give it to me harder! Make me cum all over that dick!"

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Jessica and I had met the previous night at a local bar. I never would've expected to find her there, especially since I had read about her previous struggle with alcohol. I quickly figured out as we began talking that she was not in fact there for a drink. She, instead, was there to find a guy to go home with. This was another thing that came unexpectedly to me, as I knew that she was both a married woman and a mother. But, when the beautiful Texas-native actress began whispering in my ear and rubbing her hand along my crotch, it was getting harder (no pun intended) for me to say no.

So, I did what any sane man would do: I brought the girl back to my place and we had some of the most mindblowing sex I'd ever had. I was glad Jess decided to come over to my place instead of us going back to her's. Her house may have been a lot nicer than my apartment, but her husband and kids probably would've questioned the shouts and moans of pleasure coming from her bedroom.

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I roughly gripped the buxom blonde's hips and began jackhammering my dick deep inside her surprisingly tight cunt. Her moans turned to screeches as I sensed she was near her next orgasm.

"You gonna cum? Huh? You gonna cum all over this big dick?" I teased her, rapidly pumping my member inside and out of her tender opening.

"Yes, yes, I'm so close! Fuck! Almost...there....FUCK! YES! UHHHHH!"

I could feel her walls clamp down on my cock as Jessica fell forward and landed right on top of me, her C-cup breasts pressing themselves right into my chest. Every new breath that left her lips was hot and heavy, the air sent directly to my face. But I didn't mind. Our two sweaty bodies were entangled across my tossed pillows and my wrinkled sheets.

"I haven't...came...that hard...in...so long," Jess slowly said, merely moving her eyes to gaze up at me.

"Well, I'm glad I could help," I told her, as I began to lightly stroke her sweat-drenched back.

The way the beads of sweat formed on her back, mixed with the way the light formed on her golden skin, kept my dick rock-hard as it slipped out of her. She slowly slid off of me and laid to my right, her body still semi-drenched over mine.

"You know, in our over-decade-long relationship, Eric has yet to give me a single orgasm. Then, I meet you, and in one night, you're able to make me cum every single time we have sex."

I wasn't exactly sure how to respond, as even though I'd just had sex (three times, to be exact) with his wife, I didn't feel comfortable verbally insulting her husband.

"Maybe we should just...not talk about him," I said, looking to change the subject.

"Yeah, that's probably for the best. Sorry."

We sat in awkward silence for a minute. Not once in our time together had there ever been a moment like this. It was unbelievably awful. I knew it was my turn to speak so I said the thing I believed was on both of our minds.

I turned to her and asked, "Wanna go again?"

"Fuck yeah."

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A week later, I'm sitting on the couch, checking through emails on my laptop when my phone buzzes with a new text.

It's Jessica.

When we parted ways during our last meeting, we exchanged numbers in case either one of us needed some sexual release. We had sent each other some explicit texts throughout the week but had yet to meet up again. With my job and her family (not to mention her being a celebrity), it wasn't easy to find time to hook up.

That was, until today.

I picked up and unlocked my phone, opening the text from the woman who'd rocked my world just seven days earlier.

"Hey sweetie, I miss that beautiful dick of yours. Why don't you bring it and your fine self over to my place? Hubbie's taking the kids to their grandmother's and mommy needs a hard fucking like the one you gave her last week."

I eagerly accepted Jessica's invitation, and she responded with a smiley face and her address.

"Get here quick," She told me, "I'm getting so wet thinking about that hard cock of yours, babe."

Before I had the chance to return the sexy exchange, she sent me another message. This time, it was a picture. I could easily recognize exactly what it was. It was a close-up of Jess's pussy with two fingers spreading her lips apart. She was definitely not lying about being wet, as I could see the moistness covering every inch of her sweet peach.

"Be there as soon as I can, sweetie," I added a heart and an eggplant emoji for good measure, and headed out the door, ready for another incredible night with this incredible woman.

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After what felt like an hour, but was more like 15 minutes, of driving, I arrived at the gates of Jessica's mansion. I sent her a quick text letting her know I was outside, and she replied by opening the gates.

I parked right in her driveway and made my way over to the front door, which was now wide open. Jess stood there in a green silk bathrobe, looking as fine and sexy as ever.

"Welcome, I'm glad you could come," she said, sliding out of the way so I could follow her inside, "You have no idea how horny I've been over the last week."

She closed the door behind me, and as I turned to face her, she had untied the ropes to her robe, which was now wide open.

"Jesus," I uttered, gazing over the petite blonde's utterly flawless body. Sure, she'd had some weight issues in the past, but you wouldn't be able to notice that from looking at her now.

Her breasts were soft and round, bronze-colored like the rest of her gorgeous body, and though they sagged just a bit, that's to be expected for a woman in her 40's. Her stomach was toned enough to show off some definition, but not enough to see a full six-pack. Her hips were wide and perfect for gripping while taking her in any position, while her ass was that of someone half her age. Her pussy was hairless, save for a tiny landing strip just above her mound. She quickly shrugged the robe off her shoulders and beckoned me to come closer with her finger.

"Get over here and fuck me, stud," she playfully demanded, bending over at the waist, pressing her hands against the front door, and sticking out her butt. She wiggled it, teasing me, as my rock-hard erection fought against the tightness of my pants.

I quickly undressed and positioned myself behind the short blonde, aiming my cock at her opening and roughly thrusting my hips forward, shoving every inch inside of her at once.

"Oh, fuck, baby, that's it, give mama that dick," she cooed, pushing her ass back against my thrusting hips. I reached my hand around her curvy waist and put my hand just above her sweet spot, caressing her sensitive clit with my fingers. This only got her to moan more and more as I continued my powerful thrusts that made her ass cheeks ripple. "YES! YES! YES! YES! FUCK ME! FUCK ME! FUCK ME!" she repeated, yelling out for me to fuck her harder and harder. I thought we'd better move ourselves somewhere else as her front door was see-through so it was definitely not safe, in the event her husband and kids came home soon.

I pulled myself out of the Dukes of Hazzard star and spun her around, pressing my lips forcefully against hers for the first time in a week. I gripped her ass cheeks with both of my hands and picked her up, as she curled her legs around my waist. I began walking up the stairs as she pulled her lips away from mine.

"Where we headed?" Jess asked, as I continued pressing light kisses against her collarbone, which in turn got her to continue letting out soft moans.

"Wherever the nearest bathroom is," I quickly told her, so I could get back to kissing her hot, sweaty skin.

"Oooh, you wanna see yourself while you fuck me?"

"Not as much as I wanna see your face while I fuck this beautiful ass," I responded, giving her right cheek a smack, which in return made her squeal.

We quickly made it to the bathroom, where I dropped her to her feet, bent her over the counter, and went right back to jackhammering her tight pussy.

"Uh, you like that? Tell me how much you love this cock," I told her, wrapping my other arm around her chest and pulling her back into mine.

"I love it! I love it so much!"

"You love it more than your husband's?"

"Fuck yeah, his tiny dick could never make me feel so fucking good!"

Even though I knew what I was doing was wrong, I got a lot of satisfaction out of fucking the wife of a man I have never, and hopefully will never, meet. It was also so pleasurable for the fact that it was Jessica Simpson I was fucking, and that her body seemed to be hand-crafted to my liking.

I kept giving the dainty blonde the rough-fucking she so rightfully deserved, but soon, I was getting a bit bored of our current position. So I released my rod from her wet crevice and led her into the shower. I turned on the water, whose coldness startled the two of us as we passionately made out under the showerhead, but we both got more comfortable as it started to warm up. I moved from kissing her lips, to her cheek, to her neck, and down to her glorious 34DD breasts. I mauled those perfect globe-shaped mounds, sucking and biting her nipples, making her grasp my hair in pleasure.

"Mmmmm, sweetie, you're getting me soooooo fucking wet right now," she told me as she ran her hands through her golden-yellow hair. I moved down from her bountiful breasts, to her toned mid-section, down to her near-hairless peach.

I circled my tongue around her sensitive area, teasing her, before spreading her lips with my fingers and diving into her opening tongue-first. I lapped up the sweet nectar flowing into my mouth as I attempted to bring Jess to her belated first orgasm. I kept going at her, eventually adding one and then two fingers into the mix, fingering has pussy as hard as I was fucking it not too long ago. "I'm so close, keep going, keep going! Just...a...little...longer!"

As I learned from our last encounter, Jess could get pretty loud during sex, whether or not she was close to climaxing. This was the loudest I'd ever seen her. It must have been all of the build-up to an orgasm she hadn't had yet, but I knew in under two minutes, I'd have her gushing like I did last week.

After nearly another minute, I could feel she was close to the point of no return, so I decided to give her a small boost to the finish, by sticking the tip of my middle finger in her ass, and really going to town on her clit. This proved to be exactly what she was looking for as immediately, her vaginal walls clenched down on my fingers and she let out a deep groan of relief.

"AARGH, FUCK, YESSSS, BABY, YEAAHHHH!" she exclaimed in sheer ecstasy, finally given release from the pleasure chamber she'd been kept in for however long I'd been over. I continued feasting on her delicious cunt, albeit much more lovingly and much less rough than I had been. I brought her down from her orgasmic high, while my member was still hard as steel. I reached my arm out behind myself to turn off the shower as it was getting just a bit hard to see with all of the water splashing in my face.

"God, baby, that was amazing," she said, as I stood up to face her, some of her liquids still dripping down my chin, "Let me clean you up." She stuck out her tongue and dragged it across my chin, licking up as much of her juices as she could. It was an incredibly erotic sight, especially since she stroked me while she did it.

"I'm gonna make you cum all over me, alright, babe? Mama wants a big, sticky load all over her slut face." Now it was Jess's turn to drop to her knees, but she didn't take my cock into her mouth like I thought she would.

Instead, she just spit on it and began jerking me off with both hands. She started very slow, teasing me as I did her, moaning as she calmly stroked me.

"Mmmm, baby, I want you cum so bad, you have no idea. But I wanna make you remember today forever so I'm gonna take my time with you."

She continued slowly stroking me, up and down, looking me directly in the eyes as she did. Jess knew what she was doing to me, and she loved every second of it. She knew that if she wanted to, she could have me cum in just a few minutes. But she wanted the biggest load she could get out of me, and I was fully prepared to give it to her. I knew she needed it after years of unsatisfying sex with her thankless husband. This girl deserved to be treated like the slut she so desperately wanted to be.

"You know, I just got a great idea. How 'bout you fuck these big ol' titties you can't keep your eyes off of?"

She was right, if there was one aspect of the sexy Texan's body I loved the most, it would have to be those golden globes that sat wonderfully on her small frame.

"Well, that'd probably be the quickest way to make me cum," I happily admitted, as this was something I'd been looking forward to ever since Jess and I first met.

She spit down her cleavage and then spit on my dick, spreading it out with hands to prepare them for what was to come. She got a little bit closer to me and sat up, so my cock was nearly in the perfect position to be milked by her wondrous chest.

"You sure you're ready, baby? Once I get into it, I don't plan on slowing down or stopping until I get your cum all over me."

"Bring it," was all I said before she grasped my cock between her enormous tits and got to work. Right off the bat, I was in a state of pure pleasure. I'd never had a girl with as big of tits as Jessica titty-fuck me before, it was a feeling I won't soon forget. I could tell that she was enjoying it just as much as I was based on the smirk that covered her face.

"I bet this must feel pretty fucking great for you, huh?" Jess giggled, I guess she could tell from the look on my face that I was getting closer to my orgasm much faster than I thought I would.

"Oh, you have no idea," I quickly said, trying to get my mind focused on not cumming too soon. I wanted to enjoy this, and I wanted to impress Jessica so I could solidify more meetings between the two of us in the future. I was pretty confident in my ability to keep from cumming, but I didn't know if Jess may have some secret technique to catch me off guard with.

Luckily for me, she didn't do anything tricky and just kept jerking me off with her incredible DDs. I soon began thrusting to match Jess' strokes, as I was now fully prepared to blow my load pretty soon.

"You know, my husband never lasts this long. I feel like we barely start before he shoots his pathetic load. I hope I'm not doing all this work for nothing, cause I'm really in the mood for some tasty cum."

"Don't worry, I can promise you your effort won't be for nothing."

Jess and I's eyes met and we both smiled as I could feel my orgasm not too far away. I waited as long as I could, but it wasn't even a full three minutes later before I was seconds away from spraying her down with my seed.

"Fuck, Jess, I'm gonna cum."

"Yeah? You gonna cum for me, sweetie? Come on, give me all that tasty spunk."

Jess released my cock from between her massive mounds and began rapidly stroking me, with her mouth wide open and her eyes squeezed shut. The pure sexiness of seeing this A-lister on her knees, begging for me to cum for her got to be too much and I began shooting rope after rope of cum onto the face and into the mouth of the celebrity MILF in front of me.

I lost count of how much cum went in Jessica's mouth and how much was just on her face but judging by the large grin on her face, she seemed to be pleased with the load I gave her. I watched her gather up some more cum with her finger and suck it into her mouth before swallowing so she could speak.

"Holy shit, that was one big load," she laughed, "I could barely fit it all in my mouth."

"So, does that mean your work paid off?" I joked, slightly light-headed from the huge load I just served to the still kneeling actress.

"Oh, fuck yeah. You probably just gave me more cum than my husband has in the last year."

I reached out my hand to help her up, and we both got out of the shower. We were dry for the most part, save for some of my cum which still sat on Jess's face. I was now in the process of getting dressed when I heard Jess from across the bathroom.

"Shit, they're almost home. Sorry, honey, but you gotta get outta here. I'll text you tonight." She then gave me a playful slap on the ass and I hurried out of the house, got in my car, and sped off, hopefully before her husband saw me.