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First Day On the Job

This is my first story, I hope you enjoy :)
"I...I don't know if I should. I mean its like, I need the money but I don't know if I'm willing to sell myself like this." I was just so unsure. Here I was a high school dropout with no job, no money, and living in my 27 year old boyfriend's apartment. Life is good, huh?

"Babe, I know you need the money; you know you need the money, so why don't you just do it? You're so good at it and guys would pay huge bucks for a barely legal girl like you. You're lucky I have no problem with it, too. I don't know of any other guy in the world who would let his girlfriend do this kind of business."

I guessed I could pull it off. Derek was right. I had just turned 18 and had been sucking and fucking him since I was a tenth grader. Since we had been together for so long, I guess he just trusted me with this sort of thing...

"Well, I guess this could kind of work. I mean, I definitely don't want to be living in this tiny apartment for the rest of my life...." I didn't know what to say next. Everything seemed to be falling into place. I was legal, parent and rule-free, and had a boyfriend that supported me 100%. And as if things couldn't get more perfect, Derek's sister's best friend had been doing this sort of stuff since God only knows when. She could show me the ropes and teach me everything there is to know about the "profession".

"Alright, fine. I’ll do it. I will become a hooker." 

Derek's eyes lit up. “Finally! God, Lexi, this is going to be be so great for us! You could be a total pro at this! After a while we'll have enough money to where we can move out of this hell hole and own a house! We'll be set for life!" Derek was obviously excited. He ran to the phone and called his sister's friend. Her name was Michelle, but before I heard Derek talking to her I didn't even know her name. After Derek explained my situation to her, she said she would be glad to meet up later that afternoon and tell me how to start my new career.


"So, there are pros and cons. The pros are: You have a great body and nice measurements. You have sexual experience and know what to do. You live in a great area with lots of potential clients who carry wads of cash. And, of course, you are drop-dead gorgeous!" Michelle was ten times more helpful than I thought she would be. I'd only been there for 15 minutes and she had already weighed me, taken my measurements, and measured how tall I was.

"The cons are: You seem a bit too shy, guys want to see a sexy, confident young woman. So try to break out your shell. You’re gonna need to lose the glasses and get contacts. But other than that I think that’s about it for the cons."

I wasn't really listening at this point. She had lost me after "drop-dead gorgeous" I had never thought of myself as gorgeous. Looking back, I was 5'3", had long dark hair and brown eyes. With long legs, dark skin, and measurements of 38D-26-34, I guess I finally see what she was talking about.

"So, Alexis, huh? Cute name, but you have to go by Lexi and only Lexi. It sounds way hotter. Now, we got to talk about prices. So, what would you ask for a blowjob? Or striptease? Or if a guy wanted to fuck?" She asked these questions so quickly, that I barely understood her.

"Well, for a blowjob I was thinking $10, striptease would maybe be $5, and a fuck would be...maybe...$20?" The look on Michelle's face told me that every single word I had just said was totally wrong.

"Oh God, honey, no! you're a fresh, tight, juicy little 18 year old! You also live near some fairly wealthy men. For you I'd say: Blowjob would be $50, striptease would be $20, and a fuck...about $100. Hell, maybe $200. Just make the prices up as you go along."

I liked that idea. I liked that idea a lot. And the next day, I began my job as a professional


To start me off, Michelle called one of her old clients and told him about me. He wanted to meet me and, of course, have some fun with me. Michelle had given me his address, phone number and told me about his schoolgirl fetish. So from that, I pieced together the absolute perfect outfit. I wore a long-sleeved white button-up shirt, a red plaid skirt, and one of Derek's red neck ties. The shirt was snug and revealing and the skirt was short and made my ass look incredible. I had put on make-up and parted my hair into pigtails. I "slipped" on some black super high heels and was just about ready to hit the road.

"So, what do you think, Derek? Do I look like...a hooker?" I stood in front of him, twirling and posing like a model of some sort. That was the first time I'd ever asked that question and actually expected a 'yes'.

"Oh Lexi, baby, you look so damn sexy! Good Luck! Ya gotta get going 'cause you'll be late for work!" He then gave me a kiss and sent me on my way.

After driving for about 20 minutes, I found it. Yup, this is it I thought to myself, 7431 River wood Drive. I pulled into the driveway and checked myself once more in my hand-held mirror.

As I got out of the car, my heart started beating harder and faster. I could feel my pussy getting wetter with each step I took. I took a deep breath and lightly knocked on the front door. This is it. No turning back now, I thought in the very back of my mind. Alexis Jade Holbrook, you're gonna get fucked tonight and there's not a damn thing you can do about it.

The door opened just a crack, all I saw was his eye and all I heard was his deep voice saying "Yes?"

I couldn't help but think I had the wrong place. "Uhm, hey. I'm Lexi, Michelle talked to you about me. I hear you're interested."

The door flung open. "Ahh yes, Sexy Lexi! Come in, come in! I see Miss Michelle has told you about my love of school girl outfits, eh? I just don't know what it is about those little plaid skirts and those innocent pigtails that turn me on so much! My goodness, how sexy you are!"

I gave a sexy giggle. “Thank you. You’re not too bad, yourself!" And he really was sexy. He was maybe about 5'8", had amazing hazel eyes, and light brown hair mixed with some gray. He was maybe about 200-215 pounds. I guessed he was about 52 years old.

"Oh, and my name is Louis. Sit down, darling; I want to go over something with you. So let's get right to the point, I want a blowjob, a make out 'session', and of course I would love to fuck you. But there is a certain way I want to fuck you. I want to be on top of you, I want you to scream even if you have to fake it, and I need to feel as if I'm in complete control of you. Now, I know this is a lot to ask of a young woman who is new to the business. So for the blowjob I'm willing to pay 70 dollars, for the make out I'll pay 30 dollars , and since it's your very first night as a hooker, I'll pay 600 dollars to fuck you."

I couldn't help but smile. All together that was 700 dollars!

"Oh yes, that will be the perfect price! Should we get to it? I can tell you're getting hornier by the second!" And I really could tell he was getting horny by the bulge in his blue jeans. He looked me in the eyes and nodded.

I slid off the couch and placed myself between his legs. I slowly unzipped and unbuttoned his jeans and pulled his blue boxers down. His big cock sprang out from the restraints of his pants; it looked to be 8 inches long. I wasted no time; I wrapped my hand around him and gave a big lick. I took the head of his cock and began to suck, letting all the drool run down his shaft. I started to work my hand up and down on him, sucking and squeezing with a steady rhythm. He moaned when I shoved his cock down my throat and held it there. I did this over and over. Squeezing, sucking and pulling his cock as I came up and sticking his cock deep in my throat when I went down.

He started to moan louder and I could feel his cock twitching inside my mouth. He looked me deep in the eye. "Oh God, baby, I'm going to cum!" That was my cue. I sucked and licked the head of his cock which was now a purplish-red color. Then finally he came, letting me swallow all of his warm salty goo. I looked up at him and asked, "Did you like that?" He nodded vigorously. I sat up next to him and he looked me dead in the eyes again, only this time, his eyes were greener looking than what I had remembered. But I didn't stop to think any further about it.

He leaned in and I knew it was time to make out. It started off with a gentle peck at first but that soon faded as we began kissing deeper with more and more tongue. I wrapped my hand around his dick again and began stroking him as we tongue wrestled. He suddenly jumped off the couch breaking the soft warmth of our kiss. He picked me up and carried me to his bedroom and half-threw me down on the bed. He looked straight down at me again with those enchanting eyes. He reached down and tore off my shirt and slid my skirt down until it fell off the edge of the bed. When he saw I wasn't wearing panties or a bra, his cock started getting harder and harder. 
And without any warning, he shoved his cock in my little hole. Hard. I let out a loud single moan as his cock hit the very back of my pussy. He showed no mercy; he began going in and out thrusting harder every time. He was so deep inside me, filling me up with his 8 incher. He kept plunging into me with his thick, rock hard dick. He just kept going and going, rubbing up against every soft fold of my wet pussy. The pleasure was incredible and almost too much to handle. I got the feeling that I was just about to cum. I started shaking uncontrollably and screaming louder than ever. 

"Mmmmmmmmmmm! Ohhhh God yess! Don't stop! Never ever stop!" I had never felt so good. I couldn't control it, the feeling was so deliciously amazing.

"Cum for me, baby," Louis said with his deep sexy voice. That was it. That was all it took to make me experience the absolute euphoria of cumming with a thick cock shoved deep inside me.

My nipples were so hard and my clit was throbbing like crazy. I had my eyes closed from the pleasure of my enormous cum and that’s why it was such a surprise when I felt a warm liquid drip on to my tits. That 'liquid' was cum, Louis's cum. He reached down and rubbed his cum into my chest like he was rubbing in lotion.

After we caught our breath, we got under the covers to rest a bit. "Wow," Louis said suddenly, "You sure do have a tight little pussy! Nice and wet, too." He paused for a moment. "Well, ya know, I just got my paycheck the other day and I'm feeling how 'bout I raise the over all pay up to $1,000? Would you like that?"

My jaw dropped, I couldn't believe my ears! "1,000? God, Louis, thank you so much!" I had to ask him something. Never in my life had I seen someone so generous with their money and still have a big, beautiful home like he did. "If you don't mind my asking...what do you do for a living?" I said with uncertainty.

"Well," he said "I'm the CEO of a company called Crowther & Bridges, We do banking and accounting."

Wow. No wonder he was so wealthy and generous. After that, my curiosity got the better of me. I started asking questions that related more to his family, friends, and childhood. We ended up having a lovely conversation that lasted about two hours. As we spoke, I put together a mini-summary of him.

Louis Anderson, a 54 year old man with two daughters named Jenna and Marie. He had an ex-wife named Elaine; they divorced in '97 because he caught her cheating on him with his very best friend. He served in the Airforce for a little over twenty years. He loved classic rock and horror movies. Overall, he was just a good man who was born and raised in the small town of Glasgow, Kentucky.

I fell in love with Louis after our discussion, he just seemed so perfect. There was just one problem. What would Derek do if he knew that I was in love with a 54 year old man that I just met?

(To Be Continued...)

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