Uber Driver Hooks Up with Rider

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Older Uber driver plus porn and younger woman.
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ikemay
ikemay
49 Followers

There can be a few surprises when you drive people around for a living. But the story I'm about to tell you has got to be the craziest one when it comes to Uber stories.

First, a bit about me: I'm 61-years-old, and I've been divorced for about 2 years, which happened after a long marriage. We had no kids, and I thought we were happily married, so it really set me back when she told me she wanted out. Turns out she had been having an affair with my longtime business partner. I forced a buyout of my share of the business in Los Angeles, and between that money and selling the house, it gave me an opportunity to just take some time to think about next steps for me. With no kids and no close family, I could make whatever choice I wanted.

After getting everything settled, I first traveled for a while, and then ultimately ended up in Denver as a place I thought I might like to be. It was near the mountains so I could go skiing in the winter, which I had loved to do early on in my life and hadn't done in years. Another reason for Denver was that recreational marijuana had been legalized in Colorado, and now that I didn't have a bunch of responsibilities, getting high on occasion had some appeal. I had come of age in the 70s after all, so smoking weed was something I wouldn't mind picking back up again after so many years without partaking very often.

Once I got settled in Denver, I started doing a bit of driving for Uber, simply as a way to explore the city and to make a bit of extra cash while I was figuring out what to do with the rest of my life.

So that's the setup for the day I met Cheryl. I was driving down Colfax just south of the Denver Zoo one morning about 10 am. I like to drive early mornings and am normally done by this time, but it was kind of a lazy Friday and I had nothing better to do that day so just kept the Uber app on. A ping popped up that said a rider named Cheryl needed a ride and was at Voodoo Doughnuts, just up the street from me.

My first thought was "mmmm...doughnuts," and I then thought I hoped she wasn't going far, because I thought I could swing back around after dropping her off, pick up a couple for myself, and then go home and devour them after a couple of bong hits.

As I pulled up to the curb, I noticed there was a dispensary on the corner as well. Weed and doughnuts! Honestly, what a crazy world we live in these days. Now I was definitely coming back.

I see a young woman, perhaps late 20s, standing at the curb with her phone in her hands and I pull up next to her and roll down the window and ask, "Cheryl?" At that moment, I realize we knew each other. We not only live in the same neighborhood, but we had run into each other at the park a few times, walking our dogs, and a couple of times at a local coffee shop. But we'd exchanged just the smallest amount of small talk in those moments, so it wasn't as if we really knew each other. She did remember my name, though, which surprised me.

"Hi Jeff!," she says with a smile. "What a funny coincidence." She opens the front door and begins to get in. As she does, I reach over and get the front seat moved back for her. Most riders sit in the back, so I normally keep the front seat way up. Cheryl sits down just as the seat is going back, which creates a bit of a surprise on her face.

"Oops, sorry about that," I say. "I was just trying to give you some room!"

"No worries. It just caught me by surprise. Here, can you hold these while I get buckled up?" she asks, as she hands me two bags without waiting for an answer.

One of the bags is clearly doughnuts, because it's a Voodoo-branded bag. And the other? I can smell weed a mile away, and this bag definitely had some in it.

"Well, well, well," I laughed. "Clearly you've been reading my mind," I said as I handed her back the bags.

"What do you mean?"

"Pot and doughnuts...breakfast of champions," I said with a smile.

Cheryl's face flushed a bit, and I worried that I had been a bit too forward with my comment. We were nothing more than casual acquaintances who happened to live near each other. Had I crossed a line? However, she immediately relaxed though, and turned to me with a smile.

"It's been a long couple of weeks. I turned 35 last week, and work has been a bit overwhelming. I've got three days off and I decided to treat myself by kicking it off with a nice lazy Friday of doing nothing. A bit of weed, some baked goods while baked, and a few episodes of Family Guy."

"Thirty-five?" I said with more surprise than I intended. "I had always taken you for several years younger. I guess at my age it's beginning to be a little difficult to know. Anyway, I was just teasing you. It was funny to me because when I saw your location, I was thinking about doing exactly the same thing after dropping you off, although I would have picked the Simpsons or an old movie instead. Great minds think alike!"

We both laughed, and I was relieved that it had ended up as a friendly exchange. I liked being friendly with my riders, but you could never tell how people would take things so in general I was always a bit careful. In this case, because we had met up before I had let my guard down a little, as had she, for that matter.

I should note here that Cheryl is not really close to being what one would call a "beauty." Don't get me wrong: she's cute in a next-door girl kind of way. But she carries a few extra pounds on her and was often without makeup, so always seemed just a little on the plain side. She had long brown hair that she had pulled back into a pony tail this morning, and was wearing sweat pants and a baggy long sleeve top. You know, clothes you might wear if you were just running out for weed and doughnuts! That being said, she did have large breasts, and I had seen her in a tight top once that really made them come alive.

Our houses are within a few blocks of each other, about 3 miles away, and as we headed that direction she asked a few more personal questions than she had asked in past meetings. I gave her the quick summary about how I ended up in Denver, without the details about my wife.

"Married?" she asked, a question I always dreaded a bit. She had never seen me with a woman when we'd run into each other, so I guess she was just being curious.

"Divorced. My wife had an affair, and ...," my voice trailed off.

"Oh, so sorry to hear," she said, clearly a bit mortified that she might have asked something she shouldn't have.

"Hey, don't worry about it," I said. "You just have to move on with life and I've done that."

We drove the last half-mile in an awkward silence. I got to her house and pulled up to the curb.

"There you go, Cheryl. I hope you have a great rest of your day." I paused for a beat, then said with a laugh, "I'm sure you will."

Cheryl paused as well before getting out of the car, as if she was trying to think of a comeback. And what she said next was a complete surprise.

"Jeff, if you were being honest about having the same idea, why not come inside and share this stuff with me," she asked, looking right at me. "Honestly, I should not eat the four doughnuts I just bought, so you'd be doing me a big favor of eating two of them. And of course you're welcome to share a smoke with me as well."

To say I was shocked would be an understatement, and my brain raced to find an answer.

"Look," she continued, probably aware of the look on my face. "I didn't mean to make you uncomfortable. It was just a spur-of-the-moment suggestion that sounded like fun to me. I could use a new friend, and you seem harmless, given your gray hair and all. Who knew that you were a secret stoner?" She laughed when she said it, so I knew she was getting me back for my earlier tease of her.

"Okay, sure," I finally said. "Let's go for it. What kind of idiot would turn down free weed and sweet fried dough?"

I put the car in park, turned off the ignition and got out with her. As we walked up to her door I could hear her dog begin to bark. "Charlie?" I said, remembering the name of her little mixed terrier mutt.

"Yep, that's him," she answered. "He might even remember you if you've got the smell of your lab on you."

I've got a black lab named Sam, who is now over a decade old. He doesn't get around as well as he used to, and I'm sure he's home sleeping the day away.

Cheryl opened the door and Charlie greeted us with some happy barking. I kneeled down to pet him, rubbing the top of his head. He was friendly and Cheryl smiled as I got to know him.

"He seems to like you," she said. "Why don't you take a seat on the couch while I get him some food so he won't be begging for a doughnut snack."

She went off towards the kitchen with Charlie following along behind, while I made myself comfortable on the couch. She had a TV that looked to be about 60 inches with a couple of shelves full of DVDs. Clearly this girl liked her media.

When she came back in, she had the goodies on a plate, cut up for sharing, and was also carrying a big bong with a small ziplock bag full of buds. Setting them down on the coffee table, Cheryl flicked on the TV, retrieved a Family Guy DVD from the shelf, and got it started.

Then she got out a little pot grinder, put a few buds in, and twisted the top a few times to get it ready.

"Ready to rock and roll? I'm dying to get my weekend started," she said. And with that she got the bong ready and sparked up the bowl.

"Yeah, let's do this," I replied, ready to just go with the flow of things now.

We had both taken about four good hits from the bong as we watched a couple of episodes of Family Guy, and I I was now fully buzzed. Pretty sure Cheryl was, too. Her eyes were glowing a bit red. One of the episodes had been "Road to the Multiverse," which caused both of us to roar with laughter, especially when they end up in a world where dogs rule and humans obey. Charlie didn't know what to think.

By the time that episode ended, we had polished off our doughnuts as well.

"I'm pretty relaxed," Cheryl said. "How about you? Glad you came in?"

"Yeah, I'm feeling pretty good right now. It's been fun. Perhaps I should get going so you can get on with your day?"

"You mentioned liking movies? Why don't you take a peek at my collection and see if anything interests you," she said. "I'm going to take a quick bathroom break, put Charlie outside and get some water. Want anything?"

"Water would be good." I got up off the couch, happy that she hadn't tried to get me to leave. I was so stoned by now that I would have to walk home from here. It wasn't far, but still. I looked at the two shelves of DVDs that she had over by her TV. Mostly romantic comedies, with some costume dramas mixed in. Little action, war movies or westerns, which were my favorites. But as I'm bending down to look, I see a few stuck back behind the others, kind of hidden from view. I reach in and pull out three DVD cases, turn them over and see that they're adult movies.

I quickly glance at them, and see that they're pretty damn hardcore. One seems to have a theme of couples with their babysitters, another is older and younger lesbians, and the third is just regular couples. If the movies are anything like the images, they are downright nasty.

"See anything you like?" I hear Cheryl ask as she's walking right towards me. I hadn't heard her come back, and now I'm the one with the red face because as I turn towards her it's obvious I'm holding three porn movies in my hand. I look right at her and no words come out of my mouth.

Cheryl sees what I'm holding and instead of being shocked, just smiles and says, "Well, I didn't mean for you to find those. I'll bet you're a bit surprised."

"Surprised? Yeah, some, but more embarrassed than surprised, though."

I'm frozen with fear about what to do. If I had a daughter, the feeling I have would probably be what I was feeling right then. Cheryl is way younger than me, and I feel like I've discovered something super secret about her that I have no right to know.

"Come on, you've seen your share of porn, haven't you?" She's laughing as she takes them from my hands. "In my defense, sometimes a girl has to do what she's got to do. Many women like these movies, and they can come in handy when the mood strikes."

Without really thinking things fully through before I respond, I blurt out, "I've never actually seen one." I'm not sure why I admitted that fact.

Now it's her turn to be shocked. "What the hell? You've never seen porn? How is that possible?"

I explain that I was married very young, that my wife didn't like porn, so it just was never something that I had ever gotten into. I had seen some magazines when I was younger, but had just never had the opportunity to watch an adult movie. Here I was, the older of the two, and yet I felt like the younger, more naive one.

Cheryl looked at me in silence for a minute, trying to process what I had just said. Finally, she opened up one of the DVD cases and said very matter of factly: "Well, we're going to watch one, then. I think everyone should see porn at least once in their life." She smiled back at me as she head to the TV. "I'll be stunned if you don't like what you're about to see. Any guy would. Sit down and get comfortable."

I moved towards the couch. Cheryl inserted the DVD in the player and got it started. As she sat down, she grabbed the bong and fired up a fresh bowl for us. "I can say from experience," she said after taking a big hit and blowing it back out, "anyone who hasn't watched porn while high has missed out on one of the great experiences of life. I guarantee this will have Family Guy beat."

Who was this woman? A couple of hours ago I never could have imagined being in this situation, and I was completely without my bearings. I hadn't been with another woman since my divorce, and now here I was with a much younger woman, both of us stoned, and about to watch porn. Oh well, I thought, let's see where this leads.

I took the bong from Cheryl's hands, sparked it up, and turned to the TV as the movie started. It started with a woman, appearing to be in her late thirties or early forties, sitting on a couch with a much younger woman, perhaps nineteen or twenty years old. They were discussing the teen's sex life, and the fact that her young boyfriends didn't know how to please her. The whole thing moved pretty fast. Within two minutes or so, the woman had gotten teen's panties off, her top off, and then quickly moved down to her hairless pussy and began licking it.

And with that, I was hard as a rock. My dick got so hard that it was almost painful. The buzz from the pot was also making it throb a bit, and I could feel pre-cum begin to leak out. All I wanted to do was get it out of my pants and get my hand around it. This was insane! I glanced over at Cheryl to see how she was reacting, and found her looking at me rather than the movie.

"Like what you see, old man," she said with a laugh. "Wait until you see what comes next."

I turned back to the movie at the moment that the woman's husband was sneaking to the couch with his huge hard cock out of his pants. With some encouragement from the wife, the teen put the monster in her mouth and began to suck it. I let out an audible groan at the sight.

When Cheryl heard me groan, she moved over next to me and began to unbuckle my belt.

"I knew you'd like this. Sit back and watch as I suck you off."

I lifted up my hips to help her get my pants off, and once that was done she got down on her knees in front of me and began to blow me. She licked and sucked my cock, while keeping her eyes on my face. There was no way in hell I was going to last more than a couple of minutes. Between the porn, weed and Cheryl's mouth, my entire body seemed to be on fire.

She eased back the speed a bit, sensing I was getting close, just as the guy on the screen was easing his dick into the teen's bald pussy. His wife was sucking on her tits. Cheryl switched to lightly rubbing up and down the head of my cock, with occasional light licks. I felt like I could burst at any moment, but she was keeping me on the edge with that light touch of hers.

By now the teen was straddling the guy and bouncing her pussy up and down while his wife squeezed his balls and occasionally pulled his dick out to suck on it. I wasn't going to last, and was holding Cheryl's head with both hands, guiding her to be faster.

"I'm going to cum!" I groaned, and at that Cheryl pulled her mouth off and jacked me off with her hand. She aimed my cock right at her face and I flat out exploded on it. Rope after rope of white cum streaked across her face. Who knew that this girl next door could be so nasty?

"Oh yeah, get it all out," Cheryl whispered. She smiled up at me as my orgasm slowed down to a light pulsing. No doubt that this was one of the best orgasms I'd ever had. My entire body was tingling with pleasure. Her face was covered with my jizz.

Cheryl pulled off her top as she stood up after my release, wiped her face off with it, and then stripped off the rest of her clothes as quickly as she could. Sitting down on the couch with her legs spread, she grabbed my shoulder and urged me down on on the floor.

"My turn," she giggled. "Let's see how an old experienced guy eats pussy."

I didn't need much prompting. I loved oral, and obviously the situation called out for a complete loss of inhibition or worry about what was going on. I caught the view on the screen out of the corner of my eye and saw the teen girl with her legs spread over the guy's face, who was licking away. Meanwhile, his wife was now riding his cock.

So I just got down on my knees in front of Cheryl, pushed her spread legs back to get her gash aligned with my mouth, and went to work. She had a bush, but it was neatly trimmed. The most striking thing about her pussy was the size of her labia and clit, both of which were way bigger than my wife's had been.

"Oh my God, you're beautiful!" I said when I saw her.

I spread her apart with my fingers, and began to lightly lick all around her for a few minutes. I could hear the action on the screen behind me, and when I looked up Cheryl was alternating her look between the screen and me.

"Just go for it," she said. "Get my clit in your mouth."

Do what the woman says is my motto. It couldn't be easier when they tell you what they like. I got her clit between my lips and started sucking and flicking my tongue over it. Her moans increased and she was dripping heavily now. I shoved in one, and then two fingers, sawing them in and out as I licked.

I was already erect again, and wanted to fuck her. But I kept going with my mouth, working to bring her to her first orgasm. She was now pushing her hips back at my mouth, twisting them to get the rhythm she wanted. Then she came, moaning loudly and holding my head tight to her beautiful pussy.

"Oh yeah, do it Jeff!"

As her movement began to slow, I stood up, pushed the coffee table fully out of the way, and then pulled her ass farther out on the couch, pushed her legs back and got my cock lined up with her dripping snatch. She was ready.

"Fuck me, Jeff"

The movie was forgotten now, although the audio made it clear it was still going strong. I pushed my hard cock in and immediately went balls-deep. I began a slow, but insistent fucking, enjoying my first real sex in years. Cheryl was wet and tight, and she moaned her satisfaction with the pounding she was taking. I leaned down and kissed her. She kissed back and pulled me harder into her, then reached in between us with one hand and rubbed her clit. Both of us were building up to another orgasm.

"Don't stop, I'm almost there," Cheryl moaned. She began pinching her nipples as I plowed her, pushing herself towards the climax she craved.

For me, I was in a full-body explosion of euphoria. My cock was rock hard and ready to burst, but I managed to just keep going like riding a wave. In and out, wrapped in the softness of Cheryl's wet pussy. Finally, I could feel the end approaching and slowed down a bit to make it last. I pulled out completely on each backstroke, then plunged back in slowly and insistently, making each entry really count with a bit of grinding as I hit bottom, my balls slapping her upturned ass.

ikemay
ikemay
49 Followers
12