Uptown Girl

Uptown Girl

By OlympusMons90

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I slowly open my eyes as I can see the sunlight beginning to stream in through my apartment window. As I look beside me on my bed, I can see a handsome guy still asleep, no doubt worn out from our sexual activities late last night. What is his name, Dean? David? Daymon? It began with a 'D'.

I stretch out and yawn, this seems to awaken him a little.

"Hey gorgeous, you were unbelievable last night." He looks over and says to me, what is his damn name?

"Well, you and your big cock weren't too bad either." I replied with a smile as I slowly snake my hand down to his crotch where I find the prize I'm searching for. He's already half-erect, as I wrap my hand around his impressive girth.

"I'm ready for round two if you are." He answers.

"What do you mean 'round two'? This will be like round four at least." I say with a giggle as I continue to stroke his large cock back to life.

After I finished riding him for all he was worth, I quickly went for a shower before offering him one. As he showered, I took a sneak peek into his wallet, checking out his driver's license.

'DeShawn'. I knew it started with a 'D'. DeShawn is good at fucking; a little better than my average hook-up I'd say. He's one that I'm definitely going to add to my roster, my list of semi-regular guys that I fuck when I'm not finding new guys to have fun with, so I added his name and number to my 'to do again' list on my phone.

My name is Jessica Johnson, I'm an extremely attractive 29yo Client Relations Manager for a tech company called Mem-Tech here in Los Angeles, California. I'm not exaggerating either, I really am extremely attractive. It's what allows me to sleep with as many hot guys as I want, just like the very handsome DeShawn from last night and this morning.

I'm a 5'6 tanned blonde with lovely blue eyes and round natural d-cup breasts. I'm super fit as I work out all the time, not just in the bedroom. I've lived a charmed life over the last decade, using both my beauty and ambition to earn several promotions in my career, and to enjoy an extremely fulfilling sex life.

I'm not lying about enjoying sex and being fulfilled. I get 'fulfilled' five or six times a week at least, usually with a different hot guy each time. The only guy I regularly fuck right now that isn't a young handsome guy, is my senior exec Mark Struthers. He's the Chief Operating Officer for our company, and I secretly fuck him once a fortnight to ensure my career path remains 'on track' as it were.

It's how I've earned all my promotions, beauty has a cost for any man that wants to get close to it, to touch it, to have it. My previous boss Darren 'DJ' Jarvis found that out the hard way. He promoted me twice to be his team leader for our Client Relations Team, but eventually he was in my way when I started to flirt with his boss, Mark. DJ thought he had me right where he wanted me, by his side, and in his bed. One sexual harassment claim was all it took to soon put an end to that.

Mark was eager to replace the now fired DJ with me, promoting me to the Client Relations Manager position with a secret personal agreement that I would now fuck him every fortnight instead of DJ. While he's definitely not my type, with him being 46 years old and happily married with three teenage kids, he does serve a purpose for me. I put up with the below average sex I have with him as it ensures my career at this company will continue to thrive.

Of course, being an ambitious and beautiful career woman brings its detractors of course. Other staff who are far more experienced and knowledgeable than myself get their noses out of joint when I get promoted over them, but what can I say? They're not beautiful enough nor are they prepared to fuck their bosses like I am, so to hell with them. They work for me now.

As I'm wrapping up my last meeting for the day, and after I've managed to delegate all of my own responsibilities onto my team members, my phone rang; it's my best friend Alisha calling.

"Hey Sweety, I hope you don't have any plans for this evening."

"Well, I was thinking about calling up one of the guys on my list tonight, but no, I don't really have any plans. What's up?" I respond.

"I've got an invite to a fantastic party, there's going to be a lot of wealthy eligible guys there too. So, what do you think? Care to join me and see if we can find the two most eligible handsome studs in LA for us to fuck?" Alisha answers as she laughs into the phone.

"Yeah, I'm up for that. What sort of dress code are we talking about. Casual or glamour?"

"Oh, definitely glamour. You should wear that sparkling little red number of yours, I'll wear my matching green dress. We'll have the guys begging to take us home in no time."

"Alright Alisha, text me the details shortly and I'll see you tonight, beautiful."

Alisha Jackson is my best friend, she's twenty-eight years old and started her career in her early twenties with me, both of us working at another company here in LA, but it went under and so we both had to start anew. Since those early days, we've been best friends ever since. We were both young and extremely attractive, and we both shared identical interests and goals. Our goal was to climb our way up our chosen careers by any means necessary. And our interests, well, to enjoy having wonderful sex with as many hot guys as we could find of course.

And we've managed to do both very successfully too, I might add.

Alisha is just as hot as I am, but the difference in our appearances means that at least one of us will attract pretty much any hot guy wherever we go. Alisha is a stunningly beautiful black woman, she's slightly taller than me at 5'7 and has wonderful light caramel colored skin, big green eyes, along with large tits and an ass most men would die for. When she smiles, men almost trip over themselves trying to please her.

My other guilty benefit of being best friends with Alisha, is that we get a lot of handsome black guys coming over to chat to us, more than I would probably get on my own. I even went through a phase for about two years from when I was twenty-four where I only fucked handsome black guys. But having too much of one thing gets a little old, so I've since returned to casting my net a little wider once more to include hot white and Latino guys as well. I'll admit though that when the opportunity is there for me to sleep with a handsome black guy like DeShawn, I'll take it every time.

Parties like tonight are a weekly occurrence for us, we get invited everywhere and by everyone. We rarely pay for food or drinks wherever we go, and we never have a shortage of admirers to talk with, to keep our nights interesting. On the nights where we aren't going to a party, we either go to clubs to meet new guys, or I use my 'to do again' list to setup a fuck session with one of the guys I've met before. I never fuck new guys through dating apps that I haven't already met in person and enjoyed having sex with. It's just not worth it.

My mom called me while I was getting ready for the party, she worries too much about me. Her main concern is that I don't have a long-term boyfriend, that I'm not getting married any time soon because I've been enjoying myself too much. She always reminds me that I'll soon be thirty, that I'm getting to the age where meeting the right guy for getting married and having children will become more difficult. That all the good guys will be taken already.

While a part of me agrees with her, that maybe I should be looking for a decent guy to have something more long term with before I get too old, but I've been enjoying my lifestyle way too much to do that. It's been far too easy to push the idea of marriage and kids down the road, that I'll do later once I've had my fun and have my career set.

But is that time coming sooner than I'd like?

My career is in a good place and I'm hoping to get promoted soon once again, it's what Mark has promised me for my ongoing 'favors'. And I've spent the last decade in clubs and swank parties, sleeping with way too many hot guys to ever remember them all. Yes, Alisha and I have well and truly had our fun. My mom would argue that maybe I've had too much fun, but she doesn't even know that half of it.

I remember back to last year when Alisha and I had a bet going for who could find and sleep with the most eligible studs over a two-week period. We both had to be present and agree that each guy we hooked up with was hot enough to meet our standards. I won that bet narrowly, sleeping with twenty-nine hot guys over those fourteen days, Alisha only managed twenty-five. I did kind of cheat a little by sleeping with three hot black guys all at the same time, twice. She still gets snarky with me when that topic comes up.

But is it time that I looked for a decent guy to be with? I'm not going to be young and this beautiful forever. Do I want a husband to go home to? To be with and share our lives together? But more importantly, a husband who has money, that can provide me the kind of lifestyle that I deserve. The thought of that does interest me, but I'd have to give up all of the other men in my life to do that; I'm not so sure I'm anywhere near ready for that yet.

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As we arrived at the party, we were ushered into a main hall, almost a ballroom in this large mansion up in the Hollywood Hills. Alisha was right, there are a large number of eligible studs here tonight, although some of them have girlfriends or wives with them. That doesn't stop them from checking us out though. I know those types; give them half a chance and they'll cheat on their wives with us in a heartbeat. I've lost count of how many hot guys I've slept with that then went home to their loving wives and girlfriends, oblivious to their cheating spouses.

We were offered champagne and hors d'oeuvres as we circled and mingled with the many guests. I'd already met a few hot guys that might be suitable for our after-party activities but was brought to a halt when I saw my boss, Mark Struthers, talking with a few people. What the hell is he doing here? This is going to cramp my style for the evening for sure. He'll probably want to talk with me and show me off to his friends, I just hope his wife is here too.

I rejoined Alisha who was in the middle of being chatted up by a handsome man in his early thirties, I was able to grab her arm and usher her away for a moment.

"Alisha, what is this party for? I just spotted my boss here, you know, the one I've been sleeping with." I whisper, almost in a panic.

"Really? Is his wife here too? If she's here then he'll leave you alone, otherwise you might be in a spot of trouble. This party is a fundraiser for some movie project, they've invited a bunch of wealthy investor types here to try and get their money. That's why I'd thought it'd be a good market for us." Alisha responds with a smile.

I looked back over in my boss's direction, and I could see his wife rejoining him in the group he was with.

"Yes, his wife's here too thank god, I was worried for a moment there. The thought of having to go home with him when there are so many hot guys here tonight had me a little panicked." I reply while chuckling out loud.

"Don't worry, I'm sure we can find someone better for you tonight. But is that your boss over there with the slightly balding head in the suit with a blue tie?"

"Yes, that's him. His wife does look better tonight than in her photos on his desk." I reply.

"Who's that though? That absolutely handsome slab of meat standing next to him?" Alisha asks.

I looked back over to my boss and his group again, Alisha was right. Standing beside Mark was a tall and very handsome guy who looked to be in his early thirties, I can tell he's in great shape too even though he's wearing a suit. He very much reminds me of Henry Cavill in Superman. Same hair, same great looks, same tall muscular physique. I've just found the guy I want to take home tonight.

"I'm not sure who he is, but I'm definitely going to find out. I may even have breakfast with him." I respond while laughing to my best friend.

"Hey, that's not fair, I spotted him first." Alisha pretends to protest.

"Yeah, but I've got a way in. Can you provide me cover while I get to know him?"

"Oh god, you want me to chat to your boss, don't you? Maybe I can flirt with him a bit in front of his wife." Alisha replies with a cheeky smile.

"Play nice, Alisha. I just need him to introduce me and then leave me alone. Can you do that?"

"Well, of course. You'll owe me for this later." Alisha replies as we saunter our way over to my boss's group.

"Well, this is a surprise. I didn't know that you were interested in the film industry, Jessica." Mark says as I approach him and his wife.

"We have some friends that invited us here tonight. I'm a little surprised but happy to see you here along with your beautiful wife too." I respond as he shakes my hand softly.

"Yes, indeed. This is my wife Mary, Mary, this is Jessica. Jessica works for me as our Client Relations Manager." Mark says as he introduces us to each other.

I then introduce Alisha to both Mark and his wife Mary, before looking to the man standing beside Mark, with the expectation that my boss will introduce us as well.

"Jessica, forgive me. This is Jack Batman; our company deals with his from time to time. We might both be working together more closely if the deal for the project tonight gets off the ground. Jack, this is Jessica Johnson, she's one of the stars in my team." Mark offers.

Jack offers his large hand to me, and I take it. I can almost feel the electricity between us just from touching, this is new.

"Batman, huh? I think you look more like Superman though. Do you like to wear capes?" I ask Jack with a smile.

"Not really, but I do like the idea of wearing my underwear on the outside." He chuckles with his response.

I realize I'm still holding his hand, so I slowly release it even though I don't want to. Alisha has struck up a conversation with both Mark and Mary, she's doing her part, now it's time for me to do mine.

"Mark mentioned your company might be working more with us, what is it you do Jack?"

"Well, I used to be a Data Engineer, but now I'm the CEO of a little company called DataSource that I started a while back. We have a small but productive team that provides data storage solutions here in LA. We usually team up with bigger companies like yours on larger projects to provide specific needs while you guys do the rest. Mark and I have worked together a few times in the past, but not within the film industry." Jack replies.

Fuck! He knows my boss Mark well, hopefully only in a business sense.

"That's wonderful. I hope I'll get the chance to work very closely with you soon then." I respond.

"Likewise. Are you new with Mem-Tech? The last time I worked with you guys it was DJ that was your Client Relations guy." Jack follows up.

"He used to be my boss; I got the promotion after he left." God Dammit! He knows fucking DJ as well.

I'm now hoping that both Mark and DJ kept their relationship with Jack strictly about work, although if he knows about me it might make getting him into bed tonight a little easier.

"I see. Well, congratulations, I guess. You must be very good at what you do." Jack responds to me.

"Oh, let's not talk about work. Tell me about yourself, Jack. Are you married with children? Do you have any little Batman's running around saving Gotham?" I ask, I'm very curious to know. Surely this guy isn't going to be single.

"No, I'm the sole avenger of Gotham at the moment." Jack replies with a chuckle, continuing the superhero theme.

"So, no Vicki Vale either then?"

"No, no Vicki Vale. Not even a Jessica Johnson. What about yourself? You're not married, Jessica?"

"No. I just haven't found the right superhero for me yet. Although, I've never met a Batman before." I reply while smiling at Jack, he's giving me a warm smile in return.

We continue to chat to each other over the next ten minutes until my boss injects himself back into our conversation. Alisha and I were able to exit the group to go to the bathroom to powder our noses.

"So, how is he? Any spark there? Are we talking about breakfast already?" Alisha fires off consecutive questions at me the moment we enter the large bathroom.

"Um, how do I answer all that. How is he? Well, he's nice, really nice. Not in a hot hookup way, I don't know how to explain it. But is there a spark there? Definitely. Although, maybe more with me than with him. He's so hard to read. I'm not getting the whole 'I want to eat your pussy so bad' vibe with him yet. Don't get me wrong, I think he likes me; he's just not coming across as desperate to want to fuck me just yet."

"Uh-oh, he's one of those." Alisha giggles.

"No way. He's definitely not gay. He likes me, he's just not trying that hard to hook-up with me yet is all." I protest.

"That's not what I meant, Jess. He sounds like one of those guys that's looking for a wife, not a hot fuck." Alisha replies while laughing at me.

"Oh, maybe you're right. It's been so long since I've been chatted up by guys that aren't trying to get me naked right away. Do you think that could be true? That he's looking for someone for a proper relationship?" I ask.

"Maybe. There's one way to find out. When you chat with him again, let him lead the conversation, let him ask you out without you dropping major hints that you're interested in hot steamy sex. If he wants something serious, he'll ask to meet you again days from now, not to go somewhere with you later tonight." Alisha advises me.

"Yeah. I'm not sure which one I'm hoping for to be honest. Going on a proper date with him might be just what I need."

"What? Are you serious Jess? Are you seriously contemplating being in a relationship with this guy? What's gotten into you? You know why we're here, and it definitely wasn't to be finding a husband. Sugar-Daddy perhaps, but husband, no." Alisha replies.

"Settle down, I'm just thinking aloud. It would stop my parents from complaining about not having grandchildren for a while at least. Maybe it's time I became a prim and proper wife, dedicated to the one man that I love." I chuckle in response.

"Yeah, right. Until he finds out you've fucked every hot guy from Sacramento to San Diego. I can see you now, wearing a sexy little white wedding dress while walking down the aisle, pretending to be a virginal wife while I know you'd be checking out the groomsmen, trying to decide which one you'll fuck first." Alisha replies while laughing once more.

She's right of course. Having a proper relationship with someone like Jack is simply off the table. He already knows two of my boss's that I've fucked just to get promoted, there's no way it could possibly work between us. I do want to fuck him though, so I'm hoping he at least asks me to go somewhere with him later tonight.

After we leave the bathroom, we mingle with other guests for a while, I don't want to be seen as being too desperate to take Jack home by being with him constantly. I want to see if he will watch me while I'm with other people. To see if he's interested in me or not.

I'm right, he is interested. I've caught him glancing in my direction on numerous occasions already, quietly watching me as I chat with other men, getting hit on by more than a few of them. I steal some glances back at him as well, when I know he's watching me; to let him know that although I have other admirers, it's him that I want.

Eventually I make my way back over to my boss's group, Alisha isn't with me this time, she's already found the eligible stud she'll be fucking tonight. As I rejoin them, I make sure to stand on the other side of Jack, away from my boss so that hopefully he'll leave me alone. There's a new much older couple that has joined the group, the wife is talking with Jack as I rejoin him.