During her wild college days Emma realized she liked getting fucked. She also realized that guys liked fucking her. So half way thru her junior year she dropped out and started her own escort service. Working for herself allowed her to only accept jobs she was interested in. It had been about three years and she figured she had probably worked every type of job there was for her; Virginia, married couple three-somes, boys weekends, frat parties, one night flings. But today she was looking at an email for something new. It was an offer for a week long job. For an almost impossible to pass up amount of money. Emma had looked the guy up. He was handsome. Mid-30s, shaggy blond hair, green eyes. He appeared to be in shape and unmarried. He had a pretty high level c-suite job for his age. There wasn’t much information about what the week would entail. Devon, that was his name, said he would give her the particulars once he picked her up on Sunday. If she declined he would pay her a small sum and she could be on her way. But if she accepted, he would pay the full amount after returning on Saturday. Emma was interested. Was she going to play the part of girlfriend at a family vacation? Be his arm candy at a school reunion? So even though the money was there, after 3 years of this work, the novelty of the offer ended up snagging her attention more than the cash. She emailed Devon back that she would take the job. Only a few minutes later he had responded. He would be picking her up at 10 am on Sunday. He would tell her his ideas on the way to the airport and she would still have a chance to back out. He also included a suggested packing list. Emma opened the document and scanned it. Her eyebrows rose.
Sunday at 10 am she was packed and waiting. She was wearing a cute little pink sundress. It was long enough to only be moderately indecent but any breeze would cause it to blow up showing off her ass. She had on a matching light pink lacy thong and bra. Emma wasn’t shy about her body. She knew why guys liked her. She was short, maybe 5’6″, and seemed to carry most of her weight in her ass and boobs. Se worked out to make her ass as round and high as she could and her 34GGs were all natural. A sleek black car pulled up in front of her house and she watched at Devon got out of the back. Emma was already out the door and locking it by the time he made it up the walk.
“Excited for the trip?” Devon laughed as he took her bag.
He opened the door for her, closed it behind her and then placed her bag in the trunk. He got in the other door and the car started moving. Emma sat waiting for Devon to break the silence. It took a few minutes and then he cleared his throat.
“So, do you want to know the general plan?”
“That would be nice,” Emma replied.
“I just want to make sure you know that there is no pressure. If you feel this is more than you are up to, let me know. We will return you home with $500 and go our separate ways,” he began.
Emma nodded her head in agreement and listened while Devon told her what her weeks job would be. He was going to a conference/meetings and would be busy the whole week. They would fly to the destination on a private plane. Once there, Emma’s job would be to basically service him the whole week. He wanted her in his room, mostly naked, constantly. She had free reign to order whatever room service or spa treatments she wanted. If he texted her wanting a picture of her tits, he expected it within 5 minutes. If he came back to the room between meetings and wanted to fuck her ass before heading out, he wanted her ready. If and when he had work events in the evening, he wanted her to attend. Dressed just slutty enough to let everyone there know what she was and what he was doing but not enough to get asked to leave. Emma felt herself getting excited. Sure she had all kind of guys asking to have open access to her body. But a whole week! It was usually a night, maybe a weekend. Most men seemed to tire out quicker than they expected. Looking at Devon, Emma believed he was capable of fucking her just as much as he appeared to be planning on.
“I accept the job,” Emma said while running her eyes up and down him. Letting them linger on the bulge in his pants.
The rest of the ride was spent signing various contracts and agreements and then chatting about inconsequential things. Getting to know eachother. When they arrived at the airport, Devon got out of the car first and then walked around to open her door. Someone loaded his and her suitcases onto a trolley and took them off to a plane. She looped her arm in his as he lead the way. They both sat down and sooner than she expected, perks of a private jet she guessed, the plane was in the air. She released her seat belt and stood up, looking to Devon. He was staring at her tits.
“Take off your dress and then make me a whiskey and coke.” He commanded.
Emma slipped the straps of her dress off her shoulders. She slowly slid the dress down her body, exposing her breasts. The dress hung on her hips and she removed it the rest of the way with a little shake of her ass. Then she walked to the bar and made him the drink. Swaying her hips a little more than usual, Emma walked back to Devon and handed him the drink. Then she sank to her knees in front of him and reached towards his belt. Devon leaned back and took a sip and she undid his belt, button, and zipper. She wrapped her fingers around his already hard cock and heard Devon take a hard breath. Emma felt her panties getting wet as she stroked her hand up and down his shaft. Her fingers just barely touched around his girth. He was around 6 inches. Emma liked a girthier cock. She leaned forward and took his cock into her mouth with a moan. She started slow, leisurely licking up and down his length before taking him into her mouth again. A few round of this and she felt him slide his fingers into her hair so she began sucking and bobbing on his dick. Emma relaxed her jaw and took more of him into her mouth. A little further each time until she felt the head of his cock hitting the back of her throat. She bobbed up and down, drooling, as she went. Then she pressed further, pushing the head of his cock into the opening of her throat, fully taking all of him. She heard him set his glass down as he moaned and his other hand found its way to her head. He started fucking her throat, pressing down with his hands and thrusting up into her face. Emma’s lips were stretched around his cock as she wildly moved her tongue around his shaft. He thrust up hard, pressing beyond the small opening of her throat and came, shooting ropes of cum straight down her throat. She lightly tapped his knee and Devon stopped pressing her head down onto his cock. She sucked on his dick to the tip, getting every last drop of cum out of him. She grabbed the base of his cock and then removed it from her mouth while visibly swallowing. She got up and straddled him, sliding her soaked pussy up and down on his softening cock. Devon began squeezing and licking her breasts. She picked up his drink and finished it in one long sip. Then she started kissing and licking and biting him as he fondled her. Emma was so horny. She needed him to be back in action quick. She wanted to feel that cock pounding into her pussy.
Slowly she felt his member hardening against her ass. She moaned and pressed down into it.
“Can you help me join the mile high club?” She asked before licking his neck. She grabbed his cock and placed it at her entrance.
“I think we are going to get along just great this week!” Devon laughed and then slid the head of his cock into her cunt. Emma moaned and tried to press down and get more into her but he held her hips refusing her that movement. Slowly, with each thrust he went a little further into her hot, wet slit. When he was finally fully sheathed in her, Emma was panting and begging.
“Oh fuck. Yes. Please. Oh yes please fuck me. Fuck. I need you to fuck me!”
Devon released the pressure on her hips and allowed Emma to ride him at her preferred pace. Her hands were behind his neck. One hand was around her neck, thumb pressing into her throat, the other was squeezing her breast. The hand left her throat to grab her hip as he started thrusting up into her harder. His head dropped to her breast and he took a nipple into his mouth. Emma felt the gentlest of grazes from his teeth. She moaned.
“Bite me. Oh please, fucking bite them!”
Devon clamped down on her nipple and tugged and Emma moaned. He alternated between her breasts. One hand left from behind his neck to snake between their bodies. Emma started rubbing her clit and she slammed up and down on his cock. The head of his cock just barely grazing her cervix with every thrust. Devon licked her nipple and then bit down as she fully sheathed his cock in her pussy. She came, her muscles spasming around his dick. Emma cried out as wave after wave of her orgasm took her. She slowly sank back into her body, realizing she now had her knees on the seat as Devon plowed into her from behind. She pressed back once, twice and then felt his cock twitch and then the warmth from his cum coating her insides. Devon stayed there for a few minutes before removing himself from her pussy.
They spent some time getting dressed and cleaning up, and then they were both sitting and chatting. While outside she hoped she looked cool and collected, if not thoroughly fucked, inside Emma was jumping for glee about her weeks job. It had been a long while since she had been fucked as good as Devon had. She was starting to think the money might be the bonus to the trip and not the other way around.
Source: reddit.com/r/eroticliterature/comments/112obyd/emma_the_escort_and_her_week_long_job_1
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