My Double Life as a Whore - Cover

My Double Life as a Whore

Copyright© 2023 by oliver twist

Chapter 5

Erotica Sex Story: Chapter 5 - A young lawyer on her first assignment alone, out of town, behaves in a way she shouldn't.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/Fa   Fa/Fa   Fa/ft   mt   ft   Mult   Blackmail   Consensual   NonConsensual   Reluctant   Lesbian   BiSexual   Heterosexual   Fiction   Zoophilia   Incest   BDSM   DomSub   Spanking  

As soon as Diana was gone, Tanya threw her phone on the bed and screamed, cursing herself for being so weak and not fighting her corner. She sat back down on the bed and tried to think how she was going to cope with what was coming, not sure if that was even possible. It was her own fault of course, letting Don and the others take advantage her, flirting and then going back for more, wanting to be fucked like a whore and slut.

‘Fuck.’ She shouted, standing and leaving the room, determined to buy two very expensive dresses.

The worst thing was she couldn’t really do anything about it. She knew if any of this got back to Diana and the firm, she could lose her job and career, plus be humiliated for added measure. The only saving grace was Don and Mark had the same problem, if she made a fuss about what happened it wouldn’t look good for them either. Though she felt they could ride out the storm far better than she could, they were men after all.

The elevator stopped in the lobby and she got out, feeling a little better after the ride down. Her bum was still sore as she made her way outside, the warm air a shock after the hotel air-conditioning. The shops were amazing, all of them with the classiest of dresses, just as good as anything in New York. At first, she tried on the drabbest dresses she could find, thinking of the disappointment on the men’s faces if she turned up wearing one.

But even that thought couldn’t tempt her, she was a slave to fashion and after trying five of the most boring dresses, had to try on something chic, picking out a lovely black cocktail dress. When she came out of the changing room, the young salesgirl smiled and nodded, telling her how gorgeous she looked.

Tanya did a little twirl, more than happy with her choice. It wasn’t too short and showed only a little cleavage, zipping all the way up her back but leaving her shoulders and arms bare. It oozed class and was $500, perfect, she thought.

Her next choice was just as classy, this time red and an inch shorter with just a little more cleavage on show, but still nowhere near what her dress last night exposed. Both the dresses hugged her figure but none of them were in anyway naughty, just classy and expensive. And the salesgirl said she could deliver them to the hotel for no extra cost.

Tanya was pleased with her choices and decided to do some more shopping. It was still early, and she was here for the weekend so why not indulge in some retail therapy, she thought. However, In the end it turned into a spree, Tanya getting carried away in an effort to forget about her worries. She bought three pairs of shoes, two more dresses, one as slutty as her other slutty one, and lots of underwear, sexy of course. She had a late lunch and headed back to the hotel, about $1500 poorer than when she left earlier.

By the time she got back to her room and unpacked her shopping, her thoughts were back to Don and Mark, wishing she was back in New York. At least her bum felt better, she told herself, taking another look just to be sure. As she stood up there was a knock at the door, making her jump and gasp. She quickly wrapped her body in a towel and went to see who it was, her heart in her mouth.

She opened the door an inch and sighed with relief, it was just the bellboy with her dresses. In her eagerness and delight that it wasn’t Don, she opened the door further and caught her towel on the handle, pulling it from her body. The young man just stared, her magnificent tits just a few feet from his grasp.

Tanya froze for a second, her eyes on his as he took in her naked body, making no attempt to avert his gaze. She grabbed her towel and covered herself, taking the dresses from his outstretched hand and shoving the door closed with her body.

‘Oh dear, poor boy.’ She giggled, dropping the towel and putting the dresses on the bed.

She looked in the mirror at her naked body, her fingers stroking her hard, flat tummy before moving up to her tits and taking them in her hands, her hard nipples making her gasp.

‘Fuck, Tanya, you’re excited letting the bellboy see you. whore.’ She whispered to herself, pinching both nipples.

She lay on the bed and began thinking of Don and Mark, giving up trying not to, it was pointless. It wasn’t the sex she was bothered about, she liked that, Don was a good lover but she didn’t trust him, and that scared her. Mark was an unknown quantity, he seemed rather shy and awkward but it must have been him that gave the ok to keeping her there. Afterall, he was the millionaire, not Don.

Her fingers were back at her bum, pushing one inside to see if it hurt there, which it did a little. She took it out and put it in her mouth, sucking it and enjoying the tangy taste, wondering what a dick would taste like after fucking her there.

‘Fuck.’ She said out loud.

She hated not knowing what was coming and began to imagine all sorts, no matter how ridiculous or farfetched. What made it worse was she knew Don could be capable of anything and would happily use her regardless of her feelings. She remembered how easily he made her do his bidding, letting him and the others fuck her with no real fight. He must think he owns her now and can get her to do whatever he wants, she thought, scared he was right.

She lay there thinking of her daddy and how good it would be to see him a few weeks’ time, hoping it would be warm enough to use the pool. She was soon drifting off, her eyes heavy as her body welcomed the darkness. But before she could start dreaming, there was another knock at the door, making her jump from the bed.

She cleared her head and picked up her towel, holding it in front of her as she walked to the door, convinced it would be Don this time, her heart racing again. She opened it a quarter of the way and saw the same bellboy as last time, a big, thick envelope in his hand.

‘Uh ... this was delivered for you ... and uh, they asked for it to be brought straight up.’ He stuttered, his eyes on her body again.

‘Oh, thank you,’ She said, taking it, ‘Wait here and I’ll get you a tip.’ She added, leaving the door open and walking back to find her purse, knowing the towel was only covering her front.

She shivered knowing he was looking at her bum, deliberately teasing the young man. She took ten dollars from her purse and walked back, letting the towel fall lower on her chest, showing nearly all her tits, just her hard nipples still covered. The young man, probably eighteen or nineteen, was staring blatantly, his eyes never leaving her chest. She walked slowly, giving him plenty of time to enjoy the view, her pussy twitching as she arrived in front of him.

‘Here, and thank you.’ She said, softly, holding out her hand.

At first, he didn’t move, his attention still wholly on her tits, his cock rock hard and bulging in his tight pants. ‘Thank you, Miss, and if there’s anything else i can do for you just ask. My name is Andy.’ He eventually said, taking the money.

‘I will, Andy, thank you.’ She answered, seeing the bulge and smiling before closing the door.

She laughed to herself and went back to the bed, opening the envelope and looking at the contents. It was from Don with a note, asking her to look at what the new clients were asking to be put in the contract and see how it would impact the firm’s profits if the liability clauses were ever activated. There was a lot there and it would take a few hours to go through it all, she thought, happy to do it and keep her mind occupied.

She brewed some coffee and relaxed on the bed, reading what Don had sent her, giggling every now and then thinking of the bellboy. By eight pm she was hungry, her tummy rumbling loudly to reinforce its displeasure. She put on one of her new dresses, not the slutty one, and made her way to the restaurant, looking forward to a nice meal and some wine.

Her dress was pink but not overly sexy. Quite short but not too low at the front, her tits well covered but still looking good in the tight material. She liked how it looked and accentuated her tits, knowing it would draw the eyes of men without telling them she was on offer or open for sex, something she wasn’t that evening.

Her meal was nice and the wine flowed easily, two glasses gone before she had even finished. She noticed some men looking her way but ignored them, not wanting to give any indication that she would welcome their attention. She also noticed young Andy walking in and out of the restaurant for no apparent reason, making her smile and feel sorry for him. God, she thought, I shouldn’t have teased the poor boy, he probably thinks I’m a slut now.

After one more glass of wine she got up and began walking out, thinking of doing a bit more work before she went to bed. As she passed two men on another table, one of them pushed his chair in her way and stopped her.

‘Hi, I’m Brian and this is Dickey, would you care to join us?’ He asked, smiling.

‘Oh dear, if only you had asked an hour ago. I’ve just got a booking and my client is on his way up to my room, sorry.’ She answered, smiling sweetly.

‘Oh ... fuck, we didn’t know you were ... uh... ‘

‘It’s ok, maybe next time.’ She winked, walking off and leaving them looking heartbroken.

Andy was hovering by reception as she walked to the elevator, quickly following her and joining her as the door closed.

‘Evening, Miss Green. How was your meal?’ He asked sweetly.

‘lovely, thank you. Where are you off to?’ She asked, wanting to laugh but holding it in.

‘Uh ... someone wants a hand with something on the eighth floor. I’m sure it’s not important but that’s my job, to help, anyone.’ He told her, emphasizing the word anyone.

Poor thing, she said to herself, looking at the bulge in his pants, feeling even more sorry for him now. He was probably a virgin, she assumed, looking at him. He wasn’t ugly but he wasn’t handsome, either, average looking, the type that never got laid in school.

‘Do you work here full-time?’

‘No, just weekends, I’m in high school.’ He told her, delighted she was talking to him.

The elevator stopped on her floor, Andy looking at her hopefully. Before she got, she leaned into him and kissed him on the lips, only for a second but it was enough. ‘Goodnight, Andy.’ She whispered.

He look stunned as the doors closed, not sure what to do or say. Tanya giggled and went to her room, showering before getting into bed and reading some more, though the wine made this rather difficult. She was soon asleep, the alcohol more than helping.

Sunday was a slow day, Tanya still waiting for Don to show up or phone, her anxiety getting the better of her and forcing her to the gym, spending two hours lifting weights to help with her mental state. When she came out, her body felt wonderful, hard and lean, just how she liked it. She had a light lunch and went for a nice walk, the hot sun making her feel very sexy. The town was full of people enjoying the good weather and looking good, just as she imagined they would be in Florida.

She returned to the hotel later in the afternoon and finished reading what Don had sent her, making some notes for him. It was eight pm when there was a knock on her door, making her jump, again. She had her silk bathrobe on, the one that came just below her bum and clung to her breasts, showing her nipples off perfectly through the thin material.

She opened the door, cautiously, expecting Don but getting young Andy again, sighing with relief when she realised. She relaxed and smiled, the door now open fully, letting him gaze at her body, knowing that was why he was there.

‘I was just ... uh ... wondering if you needed anything?’ He stuttered, blushing hard.

She wanted to hug the poor boy but restrained herself, instead asking him if he could get her a menu, telling him she wanted to eat in her room. He beamed with happiness and run off, coming back five minutes later with the menu.

‘That was quick,’ she giggled, ‘Come in while i choose something.’ She added, much to his joy, tingling as she walked back in.

He followed her like her a puppy, his tongue almost hanging out as Tanya sat on the bed and let the robe fall open even more as she read the menu. Her tits were almost out, only her hard nipples holding the silk and stopping it from falling completely open. Andy had his notebook ready, his eyes on her bullet-like nipples, wondering what they would feel like, his cock hurting him with arousal.

Tanya let him look, giving him something to wank about in the elevator, almost laughing again at his discomfort. In the end she ordered, standing and giving him back the menu, her nipples aching with excitement. He left to get her meal, promising he wouldn’t be long, his eyes never leaving her chest until she shut the door.

‘Oh god, Tanya, stop it, you whore.’ She gasped, her fingers twisting her nipples, hard.

She couldn’t believe how aroused she was, having this young boy fawn over her and stare at her like she was a whore. Her fingers went to her pussy, sliding in easily, her wetness no surprise as she let out a moan. She took off her robe and stood in front of the mirror, wiping her juices all over her tits, leaving them soaking wet and shiny, hoping the smell of her sex would reach Andy’s nose.

When he came back, he knocked lightly and waited, his cock still hurting. Tanya opened the door wearing the same robe, as he hoped she would be, her wet nipples even harder and clearly visible through the wet silk. He almost came in his pants when her saw her, not having a clue why they were wet.

‘Come in, I’m so hungry.’ She smiled.

He pushed the trolley to the small table and put her meal on it, including the bottle of wine. When he was done, he waited, praying she wouldn’t send him away, his eyes still on her nipples.

‘Please, sit and chat for a while, i could do with some company.’ She offered, making his day.

They both sat, Tanya pouring herself a glass of wine and sipping it, her robe falling open as she reached for the bottle. Andy’s eyes were waiting, the sight of her right nipple the most beautiful thing he had ever seen.

‘You’re beautiful, Miss Green.’ He whispered, falling in love with her.

‘Why thank you sir. And you’re very handsome.’ She told him, tucking into her dinner.

‘Are you staying here long?’ He wanted to know, hoping she was.

‘I’m not sure, at least until Thursday anyway. Tell me about yourself, have you a girlfriend?’

He told her his life story in ten minutes flat, adding he was single and available. Tanya laughed, just finishing her meal when he stopped talking. She sipped her wine and leaned back in the chair, feeling so naughty and daring, not sure she could control herself much longer. He was so young, she thought, fighting the urge to ravish him.

But she was enjoying flirting like this, teasing the boy, it made her feel sexy. She pretended to yawn, raising both hands above her head and stretching them wide, knowing full well this would let him see both her tits. He gasped quietly but she heard him, looking down at her tits and giggling like a teenager.

‘Oh my, i really should dress for dinner, sorry.’ She sighed.

‘No!’ He blurted. ‘You look perfect, so beautiful and sexy. Oh, sorry, i mean you look... ‘

‘It’s alright, Andy, i like being told I’m sexy, all girls like that.’ She reassured him, not bothering to close her robe, letting him carry on looking.

‘Can i kiss you, please?’ He asked, pathetically.

She shivered with excitement, his face all red and scared. He looked at her eyes now, pleading with her to give him something. Tanya stood and held out her hand, her heart breaking for the poor boy. Andy stood straight up and took it, letting her pull him to her bosom. She kissed him gently, their lips rotating slowly as Tanya slipped her tongue inside his mouth and played with his.

Andy was overwhelmed with arousal, cumming in his pants, groaning as he flooded his underwear, his body twitching violently. Tanya held him, realising what was happening and wanting to let him know it was alright.

‘I’m sorry, I’m so sorry ... i uh... ‘

‘It’s ok, it’s ok. Don’t worry, all boys do that.’ She told him, kissing him.

‘I should go.’ He said urgently, grabbing the trolley and rushing out.

She tried to calm him down, telling him it didn’t matter but he was too embarrassed, he just wanted to leave so he could die alone. She stood in the door as he ran to the elevator, biting her lip to hold in the giggles. When he disappeared, not looking back, she went back in, looking at herself in the mirror.

‘You are going to hell, Tanya, that was a terrible thing to do.’ She told herself, letting her robe fall to the floor.

She never thought doing something like that could excite her so much, it was incredible and such a rush, every nerve in her body was tingling, sending little shocks to her nipples and pussy. Her fingers went back to her cunt, pushing in as far as they would go and bringing the juices to her mouth, licking her fingers clean. She did this several times, wanting it to be Andy’s cum instead of her own.

It didn’t take long for her orgasm to arrive, washing over her as she bucked her hips on the bed and cried out for Andy, trying to imagine his slender young body on top of hers cumming before he even entered her. She had never been interested in teenagers before but now the thought of it excited her more than she could imagine. She felt really sorry for Andy and wanted so much to give him a treat, to give him her body and something he would remember all his life.

She showered and lay on the bed, watching an old movie and hoping Andy might knock on her door, to get his present. But he didn’t, her fantasy of him coming to her all shy and awkward and looking like a deer in the headlights, remained that, a fantasy. She fell asleep dreaming of seducing all the bellboys together, taking their virginities one by one, making men of them all.

In the morning, and still feeling a little horny, she ate her breakfast and prepared to go to meet Don at the office, hating that her body was acting this way. She finished her notes and put them in her briefcase, leaving her room at eight thirty. The cab ride took ten minutes and dropped her off at eight forty-five. The young receptionist greeted her and wished her a good day.

Suddenly Tanya wanted to run away, the thought of seeing Don and the others after what they did made her feel sick with shame, her breathing becoming erratic knowing what the looks on their faces would be. She went to the toilet and splashed cold water on her face, cooling her down a bit, which seemed to help. After a few minutes she felt better, humiliated still but able to cope, she hoped.

Don was alone in the office when she arrived, his head down in some paperwork. She tapped on the door and opened it, stepping inside, her heart racing and her face going red. Don looked up at her and smiled smugly, his eyes roaming over her body in a way that left her in no doubt what he thought of her. She wanted to slap his arrogant face but didn’t, instead just standing there as he appraised her like a piece of meat, waiting for his approval.

‘Come sit down, we have a lot of work to do.’ He told her, satisfied he’d seen enough, pulling out a chair.

She took off her jacket and sat, still blushing from her embarrassment.

‘Why am i still here, Don? You and the others are more than capable of doing this without my help?’ She asked, not sure she wanted the answer.

‘I think Mark has taken a shine to you and wants to use your charms when we wine and dine the new clients, to help them sign the papers’ He told her, chuckling.

‘Listen, what happened the other night was me drinking too much, i never... ‘

‘Save your beath, Tanya.’ He interrupted. ‘What happened the other night had nothing to do with the Champagne and we both know that it was all you and what you wanted, just admit it.’ He finished, sounding even more arrogant.

If she hadn’t already been blushing, she would have after that, his words hitting her hard, especially since he was right. She opened her mouth to say something but closed it again, knowing it was pointless.

‘Ok, now that’s out of the way you might as well do something, here, go through these and see if they’re hiding anything. Oh, and Mark wants to see us at lunchtime.’ He said, handing her a bundle of papers.

She gave him back the papers he sent over with her notes before starting on the new bundle, trying to look as though nothing was out of the ordinary but feeling really apprehensive. Don got on with his work and only engaged with Tanya when there was a legal issue, the complete opposite of their relationship last week. At one pm, Don put down his work and told her to follow him.

‘Where to?’ She asked, anxiously.

‘Just follow me.’ He told her.

She got up and followed him out of the door, asking again as they walked along the corridor.

‘To see Mark.’

They walked the short distance to his office where Don told her to wait outside while he went in, leaving her looking through the clear glass walls at they chatted, looking over at her and laughing. She felt like a child outside the headmaster’s office waiting to be disciplined. After a few minutes, Mark signaled her to enter.

‘Tanya, thank you for agreeing to stay on and help us with these new clients, it’s much appreciated.’ He said, cheerfully.

He seemed totally different from the shy man that fucked her the other night. Then he was awkward and almost embarrassed, but now he was confident and sounded like a CEO should. This time it was her that felt awkward, remembering how she stripped for him and let him fuck her without a word. She could feel her face reddening.

‘I’m happy to help with the legal work but i don’t see how i can help otherwise.’ She said, nervously, looking at the two men.

‘Well, let’s just say the clients are a little old fashion and might appreciate a woman of your, um, charms. I know Rex, the first client, always responds better to a pretty woman and that’s where you come in. Dress nicely and put up with his silly sexist jokes and occasional improper touching and he’ll be putty in your hands.’ Mark explained, sounding as though this was perfectly normal.

‘No, i will not be paraded like a hooker and treated as though this is 1956. No!’ She told him firmly, angry he would suggest such a thing.

Don responded first, his face looking like thunder. ‘Don’t be so bloody dramatic, it’s not as though you aint up for a bit of fun is it? And what if your bosses back in New York found out you were acting like a hooker anyway and fucking half the firm here?’ He asked, angrily.

Tanya sunk down onto the chair, her face ablaze with shame. ‘They wouldn’t believe you.’ She whispered, knowing the mere hint of impropriety could seriously damage her.

Mark picked up the tv control on his desk and pressed a button. Tanya looked to her left as the big tv screen came to life. At first she was confused, the sounds of sex not registering as she tried to work out what she was watching. It was when she heard the words: ‘Harder, fuck me harder,’ over and over again and saw Don’s ass pounding into her that she knew. She just stared, not able to look away, her hand going to her mouth when the camera went in close on her cum soaked bum and then to her face, the face of a very satisfied woman.

‘You bastards, how could you?’ She asked, quietly, her humiliation complete.

‘So, Tanya, you will help us out and no one but us boys will ever see this, ok?’ Mark told her, sounding really cocky.

Tanya just nodded as the tv screen went blank, a single tear running down her face. How many men here had seen that, she wondered, wanting to curl up and die. Don took her arm and pulled her up, leading her out of the office.

‘Explain everything to her, Don.’ Mark said as they were leaving.

Don took her back to his office and poured her some coffee, letting her get back her composure before telling her what was going to happen, or at least part of it. Tanya drank her coffee while Don fiddled with some papers, waiting for the right moment.

‘Tell me exactly what you want from me?’ She suddenly asked, preempting him.

‘What Mark said really, but wear a dress that shows off that body, maybe not as much as the other night but similar. And if Rex pinches your bum or put’s a hand on your thigh, don’t make an issue of it, just smile and let him. Be sexy and flirtatious, make him feel like he’s Valentino and you find him irresistable, that’s all.’ He finished, smiling like an idiot.

‘Jesus, Don, you want me to fuck him don’t you?’ She asked, angrily.

‘No, of course not, unless you want to.’

‘I don’t, you fucker. I thought we were friends!’ She gasped, still angry.

‘We are, but business is business, you know that. Have you got a dress or do you need to get one?’

‘I bought two on Saturday, but they don’t show off my tits, so no.’ She told him, defiantly.

‘Ok, go buy a couple, take the afternoon off. Oh, text me when you’ve got them.’ He told her, giving her the company card.

‘Jesus!’ She exclaimed, grabbing the card and leaving.

She stormed out and went back to the hotel, her anger now under control. She wanted to phone Diana and beg her to let her come home, to tell her the truth and throw herself on her mercy.

‘Fuck, fuck, fuck.’ She shouted, looking in the mirror.

She knew if she called Diana it would seriously damage her reputation and almost certainly ruin her chances of ever making partner. No, she had to go through with this and then get out of here. She took her two new dresses and went back to the shop, asking the girl there if she could change them. The girl was very happy to do so.

Tanya looked around the shop and picked out a few that should meet Mark’s requirement. The young girl hovered, hoping to help. It was never busy on a Monday so she was more than happy to help the pretty lady. There was no one else in the shop, which made Tanya feel better. She tried the first one on and came out of the changing room to look in the big mirror, the one in the booth too small.

The young girl was waiting, her eyes widening in approval when she saw Tanya come out. Tanya walked up and down, turning a few times to get a good look, liking what she saw even if it was to show her off to some stranger.

‘You look stunning.’ The girl told her, meaning it.

‘Thank you, it’s a present for my husband.’ She lied, not wanting the girl to think she was a real hooker.

‘He’ll be very happy, i promise.’ She smiled.

The dress was red and came midthigh, showing off her legs nicely. The front hung low and left little to the imagination, her tits free to bounce around when she moved. It was very sexy indeed. She tried on the next, coming out again, the girl waiting eagerly to see her. Tanya walked up and down, twirling as she did so, enjoying having an audience. This dress was black, short and tight, her tits squashed and pushed up, making them look even bigger than they were.

‘I like it, your breasts are perfect, i hate you.’ The girl said, giggling, looking down at her own chest.

Tanya smiled at her, telling her never to compare herself to anyone else and that she was very pretty indeed. The girl blushed a little, continuing to admire Tanya’s tits. Tanya then tried on the last two, both very short and revealing, her tits very nicely on display, which is what was required.

‘Ok, Jane, that was the girl’s name. Which two do you think he’ll like?’ She asked, still wearing the last one.

‘I like them all, you look really sexy in any of them.’ She answered, thinking she would turn lesbian for this woman.

‘Well, that’s no help.’ She laughed, going back into the booth and undressing, leaving the curtain open sightly.

Jane watched as Tanya took off the dress, gasping at the sight of her naked body, her own body feeling very hot. She stared as Tany put the dresses on the hangers, not bothering to put on her own dress yet, allowing Jane a good look. When Tanya took her dress and lifted it over her head, she looked at Jane, surprised to see her there staring, smiling back at her, tingling knowing the effect she was having on the young girl.

Jane blushed profusely, but carried on looking, strangely hoping something might happen. Tanya could see the young girl liked what she saw but wasn’t in the right frame of mind to do anything, it wouldn’t be right.

‘I’ll take these two, that should please him.’ Tanya said, handing them to Jane as she came out.

She paid with the company card and left, carrying her two choices back to the hotel, thinking how pretty Jane was and how sad she looked when she left.

When she got back to her room, she put both dresses on and took photos, knowing Don would want to see them to make sure she’d gotten the right look. She blurred her face and sent him a dozen pics, telling him she wasn’t getting anything more daring.

He answered her twenty minutes later, saying Mark was happy with them both and he would see her in the morning. She didn’t reply, admiring herself in the mirror. As much as she hated Don and Mark, she couldn’t help thinking about what would happen tomorrow night and how far they would push her. She also wondered what this Rex chap would look like, not holding out much hope he would be nice. Don would be happy to sell her to white slavers if it benefitted the company, she thought, her body tingling again thinking about it.

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