How I Became a Pro

This is the story of how I became, well, a prostitute, a woman who takes money for sexual acts. Not the street walker, whore in a bar type but more of a friend with benefits who needed a few bucks. Not much different than a girlfriend in an apartment paid for by a sugar daddy or a stay at home dad suckling his wife's financial tit.

Justification over, now let's get on with the story.

Being the little sister to a popular, successful, jock big brother gave me a perspective on males that few have. I am four years younger than Brett who was and still is a big, good looking, smart, all state athlete and has a dazzling personality. He had boys and girls in love with him. He is my brother but still pretty cool. He would often include me in things many brothers would not. Like when he and his friends built a fort out in the woods they took me. I was their "mascot" when I was young. As we all grew up things became a little more complicated. I blossomed and they grew and tensions divided, or I should say the threat of Brett grew..

I am now twenty-two and looking back at things as Brett is getting married next weekend. I am single, living at home with half of a degree finished. He is a successful broker with a gorgeous fiancé and has the world in his hand.

My mother's voice woke me that morning through my bedroom door, with her usual list of chores before she and dad went to work. She woke me up because she knows me and I am a slacker. She leaves a list on the counter so I cannot say, "I forgot." Probably a good thing since otherwise I would. I lay in the toasty covers for a few more minutes savoring the soft cotton against my mostly naked body. So warm and safe and comfy before facing another day.

I listen for the door to close and lock, then the car to pull out and the garage door to close before I light the roach from last night. Andrew, one of my brother's old friends who was allowed to date me,gave it to me after we shared a joint on the way home from the movies. Andrew is more a friend with benefits than boy friend, as most of my friends are. He is my brother's age and never quite "launched" as that Matthew McConaughey movie dubbed it. He is tall and cute and we have fun getting high and fucking periodically but not much more. Last night was purely platonic.

I am the real disappointment of the family. I am tall, five ten and blonde through and through with a slender Scandinavian body, blonde with big tits and rich dark skin. My eyes are bright blue like mom's. I did some modeling in high school. I quit modeling when the photographers started requesting my mom not attend shoots, and the clothes started to get smaller and smaller until they wanted full nudes.

I have been a party girl since days back at the fort when somebody would sneak a bottle out of their parents liquor cabinet, so when the wine was pouring and the weed smoking I wil do things I shouldn't. Somehow Brett found out I did a full nude layout and he put an end to my modeling career. He threatened the photographer and me, and destroyed the chips with the pics. He never told my parents but they knew something was up when I started bumming money. I just told them I was tired of it.

Enough backstory, now, back to the day it all began.

I sat up and piled the pillows behind me as I turned on the TV and lit the roach, inhaling my first hit of the day. "Wake and bake" I smiled to myself holding in the smoke as I laid in my childhood room. The roach did not last long but did the job as I laid back and massaged my breasts and became aware of my body and how good it felt. I thought back to last night and Andrew and some of our hotter times.

"Ding! Dong!" the front door bell chimed. It dawned on me that Andrew was coming by with some weed.

"Oh shit" I hissed, I couldn't ignore this like the exterminator mom was always telling me to let in. I grabbed the t-shirt I had dropped on the floor last night. It was cut off above my navel and too small but the sweatshirt I wore over it last night was nowhere to be found. My nipples were hard and obvious in the cool morning air but I did not want to miss him. I grabbed my gym shorts and stepped into them as I ran to the front door. I pulled it open with checking the peep hole.

"Hi Heather" an unfamiliar male voice said as the sun blinded me. I covered my eyes and realized it was my brother in law to be, Thomas. I held the door trying to hide myself and my blood shot eyes. "Just waking up?" he asked.

Thomas was thirty, an accountant or banker or something, married with a wife and two kids. He is Tara's brother, Brett's fiancé. He leered at me when nobody was looking at family events but not much more and was fairly harmless. They lived in town and he had never come to the house alone before.

"Hey Thomas" I answered confused by his presence.

"Mind if your brother in law comes in?" he said with an inappropriate tone.

"Well, I was about to get in the shower. Is there something I can do for you?" I asked trying to get rid of him. My eyes still adjusting to the harsh sun but I could see he was dressed for work, wearing khaki pants and white button down and a tie. He was not a bad looking guy but a million years older with kids made him ancient in my eyes.

"Would you like some company?" He said pushing his way into the house. "Hey!" I protested but he ignored me. "I saw your parents at the train station and thought you might be lonely." he continued as my annoyance grew.

"Thomas, really, I don't have time for this," I said annoyed still holding the door open, hoping he would just walk out the way he had come.

"I bet you do. From what I hear you are a pot head who failed out of college" he said with a snotty attitude looking around for anyone else at home. "And your brother ended your 'modeling' career," he continued, using air quotes around modeling.

"Fuck you!" I said, "get out!"

"Fuck me? Maybe, but get out, I don't think so" he said confidently. He walked into the living room and I noticed he did have a nice ass in the chinos he was wearing. God it must have been the pot or his forward confidence. I have always been a push over for confident aggressive men.

I closed the door and followed him in. He sat on the couch and smiled up at me as I crossed my arms over my chest and stood looking down on him.

"Come on Thomas, you are married, you have a kid, this is so wrong" I said trying to get him to leave. "You should leave before I tell Britney." I threatened.

"Heather, you are such a sexy girl I can't help but want you," he said almost awkwardly forward.

"thanks, but no thanks" I said growing annoyed.

He patted the couch next to him and said, "just sit next to me for a minute." He smiled up at me.

"A minute and you will leave?" I asked stupidly.

"Absolutely!" he promised with a big grin.

I knew better but either the weed or Thomas or something made me do it. I sat down on the edge of the couch as he sat back with his arm over the back behind me.

"Heather, I know you don't have many prospects but you do have some natural assets I am very interested in" he said as if he was discussing a business venture.

I stared forward into the glass sliding doors that led to the forested backyard. "I know what assets you want to mine" I said playing along annoyed.

"So I have a proposition, or deal to offer you," he said pulling his arm down and leaning forward next to me. "I mean you have something I want and more importantly need, and I have money, something I wager you want and need." His words were plain and simple and more importantly true.

"Are you proposing you pay me for sex with you?" I asked less shocked than I would have thought I would be.

From my reaction or lack thereof he was emboldened.

"Yes, Heather, we can agree upon a price for an action and no one will ever have to know." he said as if he was sharing a secret. I could not believe it. My brother in law to be, brother to my brother's wife, potential uncle to my children was proposing he pay me for sex and I was actually considering it. I hated being broke and working shitty low paying jobs sucked. So I went along.

"What do you have in mind?" I asked.

His expression said it all. "Oh nothing you don't want to do. Maybe we could start with something like a blow job?" he said negotiating our settlement. "Say one hundred dollars for a complete blow job?" It hung in the air, so sordid, so wrong, so doable.

"Complete?" I asked not exactly sure what he wanted, although I could make a guess.

The accountant in him came out as he stated in clear language the terms, "My cock in your mouth until I reach orgasm and you swallow my cum."

"A hundred bucks for a blow job?" I asked. I had done way more for way less and Thomas was not a bad looking guy when it came right down to it.

He reached in his pocket and pulled a wad of bills out. He peeled off five twenties and laid them on the table and leaned back on the couch. That was a lot of jean folding at Abercrombie's I thought.

My heart was racing as I peeped his bulge growing in his pants. I chewed on my hair like I often did when I was nervous. My toes grabbed at the plush white carpet under them.

"We can go in your room or somewhere more private if you prefer?" he said with a kind tone.

I had done hand jobs for pot before but this was crossing all kinds of boundaries. If he told anyone I would be dead. If anyone found out I would be dead. I could use the money. I was sick of getting mom and dad's guilt trip when I wanted to go to the movies. I looked back up at him as he smiled with a hopeful look.

I grinned, looking away as I agreed to his terms, showing it with my hand on his thigh. He groaned "oh god" when I did, releasing a lot of pent up nervous energy. I thought he might have just cum. He was very excited by this to say the least, and to be honest, I was a little too.

He stroked my hair and said, "Heather you are do fucking hot!"

I reached back and took his hand and pulled it off my head.

"That was not part of the deal. If you want more, it is going to cost you," I said like a shrewd negotiator. Getting straight to business, I moved my hand up and began opening his pants. He looked surprised by my rejection of his hand, but then relaxed as my hands unzipped his khakis. I fished his cock out and began stroking it. He was decent sized, not the biggest or smallest but nicely shaped.

"No hand job, in your mouth," he said firmly as he could, being as excited as a schoolboy getting his first blowjob. I flashed an annoyed look at him and asked "What Britany doesn't like to suck it?"

"No, she doesn't" he said matter of factly.

I leaned over and took him into my mouth. I wasted no time teasing him and began sucking, bobbing and generally fucking him with my mouth. This was clearly not my first blow job and he was getting more than his money's worth. I did not lick his head and stroke him like I might a boyfriend. I locked my lips on and moved up and down his entire length taking an all business approach. Not to mention Andrew would be coming over any minute.

"OH fuck yeah Heather I knew you would be a pro, a cock sucking pro" he moaned as I could already taste his pre-cum. I slurped my saliva as my mouth filled with it. Up and down, up and down. He put his hand on my ass as I worked him. I let him get a feel knowing it would quicken my work. I was turned on by this I must admit.

"Oh god yes heather! yes little sister, I am cumming!" he declared loudly, then exploded in my mouth. I sucked and pumped and milked his throbbing cock until he was completely done. A thorough job I must say. He came a lot but I managed to swallow it all. I finished by licking his cock clean then I sat up and wiped my mouth.

He was beaming laying back on the couch. I asked "been a while?"

"Yeah, months, why?" he said between breaths.

"Because you came a lot" I said with a laugh. "Guess Britany is not keeping her marriage vows too well, huh?" I said referencing his wife, my sister in law to be.

"This was her idea" he said matter of factly as he put away his soft, wet cock and zipped up. I was stunned.

"What?" I said, thinking this was a secret between us. Now it was already much more.

"What do others think of me?" I thought.

I was horrified Britany would think of me like this. What had gone from being a turn on and nasty adventure to a horror of people presuming I would suck cock for money. I guess what I needed to learn was they were right.

"Let me have your cell and maybe a price list" he said with a chuckle, like I was a take out shop.

"Uh yeah" I said as my mind spun with the idea of Brittany telling Thomas to pay me for his blow jobs. I put my number into his phone and gave it back to him. "I will let you know about pricing" I said with a disturbed look.

He stood, gave me a smile and said, "I better get to work, and earn some more cash cause I definitely want more of this, and more, much, much more," with an evil grin. He looked up and down my legs and body then dropped another twenty on the other bills and said, "That was amazing Heather!" I watched him leave as I sat on the couch, my mind racing and the taste of his cum in my mouth. As the door closed behind him I realized I was making a wet spot on the couch.

I took the money and went back to my room to brush my teeth and showered.

I really needed to have my head checked because this seemed like money from heaven. I mean sure, there were some issues, like if my sister in law ever told my parents I was taking money for sex from her husband or Brett ever found out, but seriously, I like sex and I was good at it, better than most other things. My dad always said, "play to your strengths" and being sexy and attracting men was certainly one of my strengths.

As the water splashed over me my mind drifted to Thomas. I imagined the next time I saw him. At the wedding, he would be so fucking hard watching me in my brides maid dress. He may try something.

"God I wanted him to try something" I thought as my nipples stood stiff in the warm water and my soapy hand slid down my subtle abs.

"How much to fuck me? No, I have to spread it out and make him want it so much he will pay anything!" I plotted and got hornier thinking about it. "How much could he spend a week?" I began to wonder. "Would Brittany let him spend five hundred for an hour of anything goes?" I thought as I worked myself into an orgasm. I was moaning his name as I leaned against the white subway tiled wall savagely rubbing myself.

"Oh, god yes Thomas! Yes, fuck me harder!" I played out the nastiest scenario in my head as I played with myself and came like a super star. I beamed with joy as I turned off the water and wrapped myself in a thick white towel. I bounded out into my room to find Andrew sitting on my bed.

"Who's Thomas?" he asked.