4 comments/ 20523 views/ 19 favorites How I Became a Pro By: cybal 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 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 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 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 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 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. How I Became a Pro Pt. 02 I am not going to lie, I was horribly nervous. This would be the first time I had seen Thomas, and more importantly Brittany since Thomas' visit. I was beautiful in the dress Tara had selected for us. Compared to Tara I towered over her, especially in the heels. She and Brittany were pretty in their middle America kind of way. Brunettes with full tits and slim waists. They would balloon into housewives like the rest with big hips and a belly from too many latte's and donuts. They came from money and that is what really mattered at the end of the day. I was looking for a waiter for a pre-ceremony champagne to calm my nerves when Brittany walked around the corner. She stopped, surprised to see me, then smiled a knowing grin and walked into the room where Tara was getting ready. "Shit!" I thought to myself as I walked out and grabbed a glass of champagne from a passing waiter. Thomas came behind Brittany as I continued hanging out in the hallway. "Hello Heather" Thomas said with a big smile as his eyes went from my toes to top and back taking me in. "You look beautiful," he said fairly normally. "Thanks Thomas," I said, "nice tux." "Thank you, we groomsmen have quite a tough job next to your stud of a brother." He said, with a tone I was unsure of. "I saw Brittany before," I said, testing the waters. "She is the maid of honor," he said taking a drink from the cocktail glass he held. He looked around then lowered his voice, "She did not say it, but I think she was appreciative that you are willing to service me." "There you are," my brother Brett's voice boomed into the hallway. "Hey Heather, I need this guy," he said excitedly, dragging Thomas away. "Service him?" I thought to myself. "This is too fucking weird," I thought and turned to get outside for some air, but Brittany walked out of Tara's room just as I was about to pass. "Oh, hi Heather," she started looking me up and down as girls do. She then looked around and back into the room before speaking. She whispered, "I just want to thank you for agreeing to Thomas' need." "Need?" I asked surprised by the way she put it. "Well, yeah, you know he wants to cum in your mouth, and I am just not into that," she said as if he was demanding her to scrub floors and toilets twenty-four seven. "What the hell do I say to this?" I thought. "OK, no problem," I said, hating myself as soon as I said it. "No Problem, I will suck your husbands dick for money as much as you need," I thought how it sounded. "Well, don't do anything you don't want to, ok?" she cautioned. "He can get kinda crazy with some things he has seen on the internet." Tara appeared "Hey Heather. Britt I need you," she said quickly pulling Brittany back into the room. "Crazy 'Internet stuff', huh?" I thought as a smile crossed my face and my nipples hardened. "How kinky was uptight Thomas?" I wondered. The ceremony began and I walked out with the other women. Brittany was in front of me and I could not help but notice how hot she was. "Why wouldn't she want to have sex?" I thought. I was so horny as I felt like everyone in the audience knew I was taking money for sex from mys and wanted me. We got through the ceremony and the cocktail hour was a blur as I tried to calm my imagination and feel comfortable, while the whole time trying to imagine who knew. The whiskey sours were cute and small and soon I was feeling no pain. I made small talk with my family and some old friends steering clear of thes. I was in a stall in the bathroom when I realized I was more drunk that I should be. I sat and enjoyed the feeling. I heard people come in to the bathroom and the laughing of two young women. I recognized Brittany's laugh. I pulled up my feet and sat quietly, not wanting to be discovered. "Sh sh sh," one of them said and then silence. A moment later as I heard shoes move down the row of stalls and back, probably checking for anyone listening. "Can you keep a secret?" Brittany asked. I still did not know who she was talking to and almost fell trying to get a look. "I have the most amazing secret," Brittany said excitedly as she too had clearly had some drinks. "I gave Thomas permission to have sex with another woman." "What?" The other woman said. I knew who she was talking to. It was Kate, Tara's best friend. "I know it sound crazy but you have been married for a while, right?" Brittany continued. "Yeah, six years," Kate practically moaned. She was married to Kevin. Kevin was an ex-football player with Brett, who had become successful too, but had put on a lot of weight. "The sex gets old, right?" Brittany said, as if a universal truth. "Yeah, and he is so big now, not just his cock," Kate said giggling. "I know right, well I found someone who is willing to satisfy Thomas for money" Brittany said. "How do you know he won't leave you for this whore, Britt?" Kate asked genuinely curious. "And what, have me tell the world he is fucking his sister?" Brittany blurted out. "Get out!" Kate said laughing excitedly. "Heather is fucking Thomas? For money?" she asked. "Shhhh," Brittany tried to quiet her. Just then the door opened. "Hi Mom," Brittany said in a new friendly tone. "Having a good time Mrs Talbot?" Kate asked. "Very good, and yourself?" Mrs Talbot said in her usual snotty sophisticated tone. "We better get back," Brittany said probably pushing Kate out the door. I waited in place, not wanting to face my new mother, who's son in law I was taking money from for sex. The thought of it alone excited me. "Am I horrible?" I thought to myself having seen her as the kind grandmother. Finally, she left and I got down and went to the mirror. I washed my hands and looked at myself in the mirror. I was not a bad person. Brittany and Kate seemed to appreciate my service. I looked in the mirror and winked at myself and went out to the party. "I thought you might be in there," I heard as I stepped out of the bathroom and headed to the bar. It was Thomas. I paused then turned as he leaned against the wall. He glanced over my shoulder then down my dress and said, "you do look fine in that dress Heather." "Thank you Thomas," I said as my palms were moist and hot talking to him. He brought up his hand and was flipping a hundred dollar bill around. "I would like to do a little more business," he said glancing down his tux to where his cock was bulging. "You want me to kneel down right here?" I asked nervously. "Goodness no, sweet Heather, we have a room upstairs," he explained. Was I crazy? I was actually considering it, giving a blow job for money at my brother's wedding. "It's gotta be quick," I said surprising myself, stepping towards him. He took another look down my dress and said, "That should not be a problem," then put his hand on my back and ushered me towards the elevator. I looked back as luckily there was no one to see. As the elevator doors closed Thomas cornered me and said, "I want a little more," then pushed his tongue into my mouth. I felt his cock against me as he kissed me and I opened my mouth accepting him. His hands seemed to be everywhere, my ass, my tits. He tongue fucked my mouth and then kissed my cheek to my ear and moaned "I so want to fuck you." I was nearly melted right there when mercifully the elevator dinged that we had arrived at the tenth floor. He stepped back and smoothed his jacket and stepped out. I followed him, a little weak kneed from the drinks and the kiss. He walked about half way down the hall and slid a key card into the door and opened it. He held it open as I walked in. I heard him locking the door as I moved into the main room. I was shocked as Brittany sat in the desk chair smiling. Thomas came up behind me and said, "Britt is gonna watch this time, ok?" "Watch what?" I said playing dumb with a dumb laugh. "Drop the shit Heather. I want to watch you suck and swallow Thomas' cum." she said matter of factly. "Hell I am the one paying. I should get to enjoy the show," she finished arrogantly. Thomas put his hands on my bare shoulders and said, "it's ok Heather, she is cool wth it. There is an extra fifty in it for you." I looked at Brittany who was hard to read. She was almost ten years older than me and mother of two yet was sitting in her hotel room about to watch her sister suck her husband's dick for one hundred and fifty dollars. This was too much. "OK," I said like it was no big thing. "Oh good" Brittany said as she stood and slipped her panties down under her dress, the same bridesmaids dress I was wearing. She pulled the dress up to her waist and showed her shaven bare crotch with one leg over the chair arm. She rubbed herself slowly smiling at me. I stood in shock until Thomas took hold of my arm and turned me to face him. He had his cock out of his black pants. "Suck it Heather" he said firmly. "Oh yeah Tom, be forceful with her" Brittany said obviously enjoying the scene. He looked at me seriously and put his hands on my shoulders, "Do it!" he barked louder. I got on my knees in front of him glancing over my shoulder at Brittany. She was rubbing her clit slowly and had two fingers in her mouth. "Holy shit! She's gonna do it," Brittany said watching intently. I took his cock in my hand and stroked it then leaned forward and licked the head. This was different from the first time. I felt like I wanted to give Brittany a show. I wanted to show her I was better than she was. I kissed and licked the cock head wetting it with my saliva and tasting his pre-cum already. "MMmmmmm," I moaned glancing at Brittany who was now using both hands on herself. Heather was turned on by the sight of her sister masturbating. She glanced up at Thomas who was also watching Brittany. This annoyed Heather so she sucked his head into her mouth and began to bob. She could not see his attention now but knew as his hands came to her ears and steadied his thrusting hips, he was at least partially interested in her. I could hear Brittany working herself. The room filled with the smell of sex and I was intoxicated by it , only able to breath through my nose. Brittany grunted and groaned as the chair banged into the desk with a steady rhythm. "God this is hot," Brittany said, as she masturbated. I was surprised by this side of Britt who publicly was a prudish church mouse. We all assumed the only sex Thomas got was the two times he knocked her up. We were obviously wrong. "Look at her with it in her mouth Britt," Thomas said. "She wants it, she wants me to cum down her throat, she likes it," he said as if explaining an unknown phenomena. "She's a fucking whore!" Britt hissed, rubbing voraciously, as she was obviously close to her own orgasm. "She would probably eat my pussy for a few more dollars," her tone was angry, but she was not far off. I was so wet right then, I would have done anything they wanted for free. I pulled his cock from my mouth to make them crazy and said, "love to, sis" then he rammed his cock back into my mouth. "Oh God!" Britt's voice cracked as she cried out. Thomas was now pushing into the back of my mouth, crushing my skull in his hands. They were both so close to huge orgasms. "Cum with me baby" she cried as I concentrated on not gagging as Thomas pushed deep into my throat. "Yes, baby! I am so close!" Thomas cried lovingly to his wife. "Suck it bitch!" he hissed down at me, making me hotter still. I obeyed sucking harder on his cock head as he quickly pushed and pulled in and out of my red lips sloppy with saliva. "Yes," was all Britany said as the chair banged in to the desk one last time and Thomas exploded into my mouth. I slurped loudly wanting to finish with style as he pumped a huge load. Some ran down my chin having bubbled out of my mouth. Luckily I wiped it before it fell on the dress. He finished and pulled away leaving me on my knees catching my breath. Thomas went to Brittany who was splayed across the chair and kissed her deeply. "I love you," he said to her. "I love you too," she told him. I could not help but watch this bizarre scene. He slid his hand down to her leg and dipped it into her wet folds then tasted his wife's pussy. "Mmmmmm," he moaned satisfied with the flavor. "Fuck that was hot" Brittany said glancing at me as I sat on the edge of the bed. "You can go, sis," Brittany said sarcastically, like she was dismissing the maid. "Uhh, what about the money?" I said, not having been paid for my services. Thomas walked over, smiled and winked as he gave me the money. "Thanks, and let yourself out ok," he said then turned back to his wife. "Crazy fucking people," I thought as I walked out into the hall and straightened my dress. I went back to the party and got a shot of Rumpelmintz to wash away Thomas' cum. "Heather Thornton," I heard someone say from behind. I turned and there was Kevin O'Malley, Kate from the bathrooms husband. "Hi Kevin," I said taking him in. I had not seen him in years. He was a hotty in high school but now had put on a hundred plus pounds? He was tall, six five or something but now was enormous. The awkwardness in this goes beyond the fact his wife knows I an a prostitute, but I had given him a blow job once. "You are looking good little sister," he said with the same swagger he had in high school. I had fallen for it then but now things were different. "Kevin?" I heard Kate calling from behind this mountain of a man. "Come on Kevin, there is someone I want you to meet." Kate continued pulling him away without even a look at me. Kevin smiled taking a look up and down me the winked and followed his wife away.