Karen, the Rideshare Whore

*** This is an story concept, that I am thinking of making into a series. I would appreciate any thoughts on this, and as always, I appreciate any input on my writing and the direction you would like to see the story go. ***

Chapter 1

Wiping the thick, sticky cum off my face, I laugh at myself, thinking, “The things I do for a good rating.” But seriously, it is less about the rating, and more about the handful of twenties, that the guy tosses down on me, as he is getting out of my car. That’s what really matters, and THAT is why I stick with this shitty job at all. I currently work for a rideshare service, whose name I will not share, because I do not want to get myself into legal trouble with them. It is clearly not my dream job, but as you might have guessed from the previously mentioned cum on my face, I am making the most of the opportunity. I guess I should back up a little, and tell you who I am and how I got here.

My name is Karen. Yes, I know. I hate it too. Believe me, I get it ALL the time. It was never a problem growing up. I even liked my name. It wasn’t until recently, that I started to be ashamed to even give my name for my Starbucks order. I want to be clear. My name is Karen, but I am NOT a Karen. As you hear my story, I think that will come through loud and clear. So, back to my story…

I “blossomed”, as they say, early and in a BIG way. I was always a petite girl, but then when I was 18, in a life changing twist of fate, the Boobie Fairy came one night, and “POOF” she hit me with a double dose. I am not kidding. It was like I went from no cups, to DD cups in the blink of an eye. Not that many people blink when they first meet me. It is more like they lose their ability to blink. Apparently, they also lose their ability to see my face or keep their saliva in their mouths. And I am not just talking guys, girls too.

I could say that I was embarrassed and ashamed by all the attention. I could say that I am a modern woman, that wants to be taken seriously. I could say that I don’t want to just be known as the hot girl with big tits. But who am I kidding? I fucking love my big tits, and all of the attention they get me. I am no rocket scientist. I always knew that I wasn’t going to college on some scholarship. I realized early on, that my body was my ticket to getting what I want out of life. Life gave me these lemons, so I was going to make some lemonade, the kind of lemonade that guys will pay serious money to get a taste of.

As you can imagine, I was very popular with the boys, and I was serving up a LOT of lemonade. I was not hung up about sex. My father was never in my life and my mom had a constant parade of men through her bed room. That kind of de-mystified sex for me. My mother also taught me that a little sex, goes a long way, toward getting what I want. As my Algebra Teacher would say, “Life lesson “A” plus tits “DD” equals opportunity.”

It didn’t take me long to go from sucking guys’ cocks for buying me a nice meal, to just skipping the meal. I quickly discovered that I can buy my own damn meal, or what ever the fuck I want, with the money a guy gives me for sucking his cock. Sometimes, I didn’t even have to suck a guy’s cock. You would be surprised how many guys will pay, just to feel up a nice set of tits. I would say that the Boobie Fairy made me into a cash cow, but I will cut a bitch, if she calls my tits, udders, lol.

I don’t want you to get the wrong idea. I am a lot more than a set of tits with legs. I actually have a great body. Before the Tittie Fairy blessed me, I was a very talented gymnast. I have a lithe body with good strong legs and a pert, round butt that looks almost obscene in a leotard and body suit. Yes, even before the tits, I hade more than my share of guys perving on me.

I know what you are thinking. Gymnast body and gymnastic talents, plus big tits… DING DING DING… You guessed it… Stripper. “Exotic Dancer”, please… Oh, who am I kidding? I was a stripper, and I was DAMN proud of it. To test the waters, I started dancing at a club that did amateur nights. I wanted to see if the reality was as good as the fantasy. The bottom line is, I fucking LOVED it. The energy of the crowd watching me with lust filled eyes, is like a drug that switches my brain “off” and switches my pussy “on”. Not just “on”, It dials it all the way up to 11.

I quickly discovered that guys REALLY like a stripper, who obviously enjoys her work. I became very popular and was soon getting a lot of lucrative offers, from some of the more upscale clubs. I finally got an offer I couldn’t refuse. That is how I started dancing at the most exclusive, and upscale club in LA County. Again, for legal reasons, I will keep the name to myself. The name is not important, the opportunities I got from that job, are what are important. And I am talking some AMAZING opportunities.

I had a number of high rollers, who liked my “energy”. I would like to say, that I became rich and lived happily ever after… But this is not THAT kind of story. I let myself get overwhelmed by the lifestyle. I lived for today and didn’t think about a long term plan. I figured I didn’t need one. In fact, when I attracted the attention of a guy with WAY more money, than looks, I figured I hit the lottery. He loved spending money on me, and I love having money spent on me. It was a marriage made in Heaven, as they say.

Yeah, he actually married me. Who does that? I am girlie enough to admit that I love the movie “Pretty Woman”, but I am a grown ass woman, and I know that, that shit doesn’t happen for real. So, when he got serious with me, I never expected it to be as life changing as it was. I have to admit, I was overwhelmed by the whole experience and didn’t go in with a long term strategy. If I did, I would have done a LOT more research on pre-nups. As it turns out, the term, “What each enters the marriage with” actually means something. Yes, you guessed it. It meant something VERY bad for me.

I should have known it would all end badly. As it turned out, I had an incurable disease. I was getting old. After 15 years of marriage, my disease apparently became unmanageable; for him, at least. Lucky for him, he was able to find another girl with a much less advanced form of the disease. In plain language, he dumped for a younger girl. So with a less than adequate termination package, I found myself on the street, alone.

I tried to go back to dancing, but I quickly discovered that there is no market for over 40 dancers, who let themselves go a bit. And when I say a bit, I mean a LOT. My once pert butt is now… plush? luxurious? Let’s just say that there is a LOT more “cushion for the pushin”, as the boys used to say. I don’t want you to think I turned into a pig or something. I am just WAY too far away from dancing shape. On the plus side, I am getting a LOT more attention from black guys. Who knew that they liked girls with big tits and fat asses?

I tried doing a little hooking, but without the access that the club gave me, it was just too risky, trying you find a reliable group of clients. On line was OK for random hookups, but too many guys from there, turned out to be flakes, who didn’t come ready to play… or to pay. Between the trickle of internet guys and the random hookups, I was getting by, but I needed a more steady income. To my shock and horror, that meant getting a real job. But what can I do, that requires no education, no experience, and no motivation? I also needed something flexible enough to allow me to supplement my income, with the occasional trick. The answer came to me as I was taking a rideshare car home from the grocery store. I looked at the driver, with his “bored with life” expression, and I thought to myself, “I can do this,” and a legend was born… Yeah, it wasn’t really that dramatic.

Chapter 2

I was shocked at how easy it was to get a job as a rideshare driver. Apparently, my lack of a criminal record, and possession of a valid drivers license, made me eminently qualified. Of course, I also needed a car. I was lucky on that matter, because one of the few things from the marriage, that I was able to keep, was a sweet Range Rover SUV. I just never drove it because the damn thing guzzled gas and the maintenance costs were unreal. Hence, why I was taking a rideshare on that fated day. With this new gig, I can reliably keep it maintained and the tank filled. Also, I quickly discovered, that customers often prefer luxury SUVs.

You would think that I would be bored driving for people, after my life of drug fueled sexual mayhem, but I wasn’t. I actually enjoyed the interaction with people. I forgot how much of a “people person” I am, and how much I crave the attention of others. Most people respond very well to my overly engaging style. Of course, there are always some people that just want to just sit there and ignore “the driver”, but fuck them. I live for me, not them.

For me, there is a fine line between interacting and flirting. To make things worse, I get downright sexually aggressive, when I have not been getting any, for more than a few days. So, it didn’t take long until guys started responding just as strongly to by flirtations. I remember that first time, that a guy I was driving, looked at me in the mirror, gave me a knowing smile, and told me he was not in THAT much of a hurry, to get to the airport. Lucky for him that I know all the good place to park, that are out of the way. Lucky for me, he is packing some serious meat.

The car was barely stopped, before I got in the back seat and almost tore his pants off. He is just as motivated and we look like a couple of teenagers going at it in the back seat. He latches onto my tits, and I latch onto his big cock. We hit an impasse, when I need that cock in my mouth, and he wants to keep my tits in his. My tits are big, but not THAT big, lol. Lucky for both of us, he decides, that his cock in my mouth is better than my tits in his. All pride aside, I give amazing blow jobs. And this guy is getting some of my best work. I am sure he is about to break into song, when he feels what I can do with my lips, and tongue, and throat. I could have made him cum in seconds, but I make it last. I discovered early on that this is the best way to get repeat customers.

I also didn’t want him to cum, before I can get my pussy filled, by that big ass cock. And filled it was. My GOD what a waste of cock, that his wife is not plowing herself on it every damn night. I can tell by the look on his face, as I ride him, like I am trying to win the Kentucky Derby, that he has NEVER been fucked like this before. I SLAM down on him and feel him punch up into my guts. I throw myself up and off of him, so wildly, that my tits flop up and almost SLAP the roof of the car. Then SLAM back down, over and over. When I cum, I scream so loud in the confined car, that I feel like I will go deaf. Just then, the guy GRABS my tits in a death grip and I feel his cock twitch inside me, as he cums. I am not sure how long he has been holding that one, but he cums spurt after spurt, in thick, hot, surges of cum. I can feel it squishing out around his cock.

Being the full service cock sucking, customer fucking, rideshare driver that I am, I immediately grab the package of sterile wipes, I keep in the console, and start to clean him. I almost feel bad that his cum is not only covering his thighs and running into his butt crack, but it is also all over the clothes he was wearing. I do my best to clean everything, but he seems much too distracted by my still naked tits, shaking and bouncing, as I lean over him, wiping him down.

As we both get dressed and get back on our way to the airport, my customer, we will call him “John”, gives me his card and asks if I have one also. I tell him that since I just started driving, I don’t have one, but my profile is on the ridesharing Ap site. Then, I tell him my number, so he can put it in his phone. I also tell him, if he ever wants to hire me directly, he doesn’t have to go through the Ap. He smiles, getting the vibe I am putting down. I also ask him to please make sure to rate me well on the Ap, as well as spread the word, that Karen gives good service… You never know, word of mouth can make or break a new “business”.

Chapter 3

Apparently, word of mouth travels fast. Not even three days after my first “rideshare with benefits” I get a call from an unfamiliar number. The caller tells me that he is friend of John’s, and that John highly recommended me. He goes on to tell me, that John told him what a great ride I gave, him and that I would take him anyplace he wanted to go. I am taken aback a little. It is a bit forward for John to assume I would take a guy “anyplace he wanted to go”. I mean, it’s not wrong, but it is presumptuous. Or else I wasn’t as coy, as I thought I was, lol.

John’s friend, coincidentally, also named John, asks for an 8 PM pick up time and gives me the address for the pick up. Then he tells me that he has almost two hours for the ride, and tells me I can pick the route. WOW, I am really starting to like this rideshare gig. I tell John #2, that I definitely want to take the scenic route, but that it will cost more for gas, and tolls, and what not.. Without any hesitation, he tells me that he will pay what ever it costs, for a satisfactory ride. I tell him, I guarantee satisfaction… or the next ride is free. I actually heard him GASP on the other end of the phone.

After my first experience, I decide to dress smarter. I was definitely not prepared the last time, for the rushed tearing off of clothing. This time, I am wearing a nice loose, flowing skirt and no panties. I also put on a nice pushup bra, that makes my tits even harder to ignore. Over that, I put on a nice sheer white, button up blouse, that gives just enough of a view of my bra’s lace pattern, to draw the eyes… Yeah, as if eyes need to be drawn to my big tits, lol.

By the time I arrive at the pick up point, my pussy is so overstimulated that I am practically drooling down my thighs. I feel a trickle of my pussy juice sliding between my butt cheeks. I dance a bit in my seat, to relieve the tickling feeling of the offending fluid, and to alleviate the nervous excitement I am feeling. I see a guy, who seems to recognize the Rover, as I drive up. I open the passenger side window and he leans in, asking “Are you Karen?” With a flood of relief rushing through me, I answer, “Yes, and you must be John.” He tells me, “Absolutely,” and then hops into the back seat.

As I pull away from the curb, I look in the mirror, to assess my new “fare”. He is cute. He is big and strongly built, and I imagine that he can break me. A shiver runs down my spine, as I think this. Yes, more dancing in my seat. I see his eyes meet mine in the mirror. I actually blush and look away. When I build the nerve to look back into the mirror, his eyes are there waiting for me. He gives me a wicked grin, and my legs get so weak, that my foot actually slips off the gas pedal. As the car stutters, I hear him laughing in the back seat. I am about to make a smart ass remark to him, when I feel his hands come around my seat on each side, and cup my tits. I GASP out loud and think, “Oh MY… I wasn’t expecting THAT.”

Stuttering, I tell him, “Therrre, is a nice sssscenic over look up ahead… If yyyyou would like to ssstop.”

He SQUEEZES my tits, pulling me back against my seat and growls into my ear, “YES… I really, really want to stop and take a better look…”

I am shocked that I am able to pull into the scenic look out, without driving right over the edge. My legs are weak and shaking, and did I mention that he is STILL holding and squeezing my tits? There is something so fucking hot about a guy being behind me, and grabbing me like this. For a second, I imagine that he is a guy who I was teasing so bad, that he loses control, and takes me by force. I feel my excitement spike even higher.

As I stop the car, he growls in my ear from behind, “Get your ass back here and show me those amazing tits.”

I’m already unbuttoning my blouse, as I throw my door open and almost run to the back door. He locks it and I stand there uselessly pulling up on the handle, over and over. He gives me a devilish grin, and tells me, “Take it off out there…”

“My GOD, he is a BAD boy,” I think to myself, as I start to slowly, erotically take off my blouse and bra. And to think my mother said all those years stripping were a waste of time… I watch him through the window, as I teasingly unclasp my bra and slide the straps down my arms… holding the cups to my full, round tits the whole time. As I drop the bra, I quickly turn my back to him. I smile, knowing how frustrated he is at this very minute. I slowly turn… my hands now cupped over my tits. I squeeze them and rub my palms on my quickly hardening nipples. I push one arm across my tits, as I free the other hand. I wink at him and give him my best “come hither” motion with my finger.

I laugh when he fumbles with the door handle, over and over, forgetting that he locked it on me before. He realizes this, flicks the unlock button, and throws the door open.

Seeing this big, strong man coming at me with such overstimulated energy, is scary, but so fucking exciting. He reaches around me with one arm and pulls me to him so hard, that the air in my lungs is actually pushed out. Before I can catch my breath, his mouth is covering mine, and he is kissing me VERY hard and VERY passionately. He has literally taken my breath away. I actually start to feel light headed, and push my hands against his hard muscular chest. He releases me just enough to catch my breath. As I am gasping for breath I say, “WOW… Holy FUCK, you really know how to make a first impression on a girl, don’t you?”

He doesn’t say a word, He just grins at me and then reaches his hands up to cup my tits. He keeps looking into my eyes, as he lifts my tits in his open hands, as if he is weighing them… assessing their value… Then he cups them again, squeezes them together, and takes both nipples between his thumbs and fingers. He rolls, and pinches, and pulls my nipples. The whole time he never stops looking into my eyes. I feel like he is looking right into my soul. I feel my pussy twitch with excitement. He notices me squeezing my thighs together and releasing, over and over. He smiles and I think to myself, “MY GOD… This guy can do more to me with just his smile, than most guys can do with their mouths and fingers combined.”

Still not breaking eye contact, he puts his hand on the top of my head and pushes down. I know what he wants, so I obediently lower myself. Well, I stop just long enough, to reach in and grab the floor mat from the floor of the passenger seat. Hello, gravel parking lot, at a scenic over look. Ladies, you know what I’m talking about. Guys, ask your ladies.

I reach up and feel the nice big bulge in his pants. I run my hand over it and SQUEEZE. I love the way he jumps and sharply inhales. I keep cupping his bulge, as I unbutton and then unzip his pants with my other hand. As I reach my prize, I realize why he and John #1 are friends. They are both in the “nice, big. thick, cock club”. And I am a BIG fan of that club. I show my appreciation, by taking the big smooth head in my mouth and relishing the feel of it, as I suck gently and run my tongue around it. I taste his salty pre-cum. It feels so slick on my tongue, as I run it around his big mushroom head. I moan around it. He moans in response.

I keep sucking the head, as I take his cock in both of my small hands. My GOD. I have both hands stacked, and still my top hand doesn’t touch my lips. I push more of his cock into my mouth. I feel it push against the back of my throat, just as my lips meet my hand. Again I think, “My GOD, this guy has a big dick.” Momma didn’t raise no quitters, so I relax my throat and start swallowing. I get past the opening of my throat and get more and more of him in me. Breathing through my nose, I work more and more into my throat, until I feel his pubic hair tickle my nose.