An Indecent Proposal

Armando Martin de la Guerra spent yet another day on a cheap bar, but this time he savored the whiskey very slowly. He feared it would be the last time in very long where he could have just a little taste. It was his favorite place to drown his worries, for the bartender – a dour, slim man with bags in his eyes and a raggedy stubble – didn't ask him for papers, and the other patrons were just as down on their luck as he. Though, in this case, he was worse than them – or at least, he thought.

The woman was too good for that place. She was old – probably on her late forties or early fifties – but she was absolutely gorgeous. She had an air of elegance, perhaps because of her platinum blonde hair tied on a bun, or her green eyes, or her thin nose and small lips, or perhaps the skin-tight dress showing her large cleavage and her wide hips, but regardless of what it was, she was a looker – and the patrons agreed, for she stole all of their looks. But, of all the patrons wasting their time with hard spirits, the woman sat beside him. She didn’t pay attention at first, asking the bartender for cognac on a rimmed glass, but as soon as she received her drink, she broke the ice with him.

“What’s a young man like you doing in this place?”

He wasn’t that young. Perhaps it was his clean shave, or his youthful haircut, but he was already on his thirties, and already down on his luck. His mood certainly showed that. “What can you expect, ma’am?”, he said, with a Hispanic accent of someone who lived in the Southwest for over ten years. “Drowning my sorrows.”

“Such a shame.” The woman rubbed her wrinkled, delicate hand – its ring finger adorned with a glistening stone atop a ring – over his naturally tanned skin. “May I ask why?”

Armando laughed, but he truly wanted to cry. “Do you have time to spare, ma’am?”

“If the story’s interesting. I was just wondering why such a handsome man would be in this place, at this hour.”

It was an hour after noon – the hour where only the chronically alcoholic and the desperate filled the bar. “Celebratin’ what little I can before things go downhill.”

“Oh”, she said in a very amused tone. She had a strong nasal tone, but the inflection of her voice suggested someone with etiquette – aristocratic, he thought. He wondered why a rich woman in her middle age would spend the day here, rather than on a country club, or a fancy restaurant. Yet, she pressed on. “I like your outlook in life, young man. What happened?”

Perhaps it was the whiskey kicking in, or perhaps her pheromones, but Armando quickly opened up to his woes. An educated Mexican immigrant, he studied Business Administration at Berkeley with a full scholarship – a testament to his study ethic – but a bad twist of fate left him out of school before his last year could be completed. Without his scholarship, his visa would soon expire, and rather than return to his native land defeated, he would try to find a job – anywhere – and try again. He laid the many jobs he worked at without papers – gardener, cook, even driver – while he worked his immigration status with a lawyer. Yet, between the rent, the utilities, the ramshackle white Dodge that wanted something replaced every three months on the dot, and the rising costs of life, soon he had to determine whether it was prudent to pursue any of those dreams.

Then, a saving grace – an old friend of his, who had just been recruited into an accounting firm, suggested him to look for a job there. He began as a courier, moving correspondence back and forth, and with his friend’s aid, he managed to secure a better position once he showed his skill at numbers. After nine years, everything seemed to be turning for the better.

Until the moment his friend was fired for embezzlement. “And”, he finished his tale, “as a scapegoat, I had to take the hit.” He took the last swig of whiskey – the third glass, as the woman was much too generous and paid him over halfway through his story – and muttered beneath his teeth. “So much for bein’ a compadre.”

“You feel he used you, then?”

“Yeah. He needed a useful idiot he could blame, took the money and left me with the broken dishes.” He scratched his eyes with the back of his hand. “And just when I was starting to save some money.”

“How much did you save?”

Armando cackled, coughing immediately afterwards. “One month’s worth of bills. Two, if someone manages to buy my car.”

“Hmm...” The woman sniffed her sweet cocktail before finishing it, sucking the lemon slice and yanking the pulp with her teeth. “Must be truly desperate.”

“You have no idea, ma’am.” He still had time for a dark joke. “What, you’re gonna be my sugar mommy?”

“If I said yes, would you accept?”

Armando was at a crossroads. He knew little of the woman, for she was more interested in hearing his tale of woe than speaking about herself, but here she was, offering him an opportunity of a lifetime. However, he was still sore from the betrayal of the man he thought was his friend, and the deal sounded too good to be true. “Not like I had another chance”, he finally decided, erring into the side of wisdom. “What’s the catch?”

“There’s a proposal I wish to make of you. But this isn’t the place to do it. Come with me, and I’ll tell you everything in detail.”

“Sounds too good, ma’am, but I don’t know much about you. Your name, for example.”

“True - where are my manners.” The woman extended her arm, prompting Armando to grasp it. “Evelyn de Thiel. A pleasure to meet you, Mr. Armando.”

--

He expected a mansion, perhaps, or a penthouse, but not a whole apartment complex. It was a walk-up, with six apartments and its own small parking lot, though to his surprise it was mostly empty. More surprisingly was her response when he asked who else lived there.

“Nobody”, she said with a grin.

“How do you pay for all of this?”

“I have my ways”, purred Evelyn. “The apartment in front of mine is dreadfully empty, however. Perhaps it could have a new owner – if you agree, of course.”

He was further surprised by the frugality of Evelyn’s own domicile. It wasn’t very lavish, but it had the necessities anyone would desire – a good sofa and velvety couch, a fully-stacked kitchen, a small glass-top dining table, and a large flat-screen TV with a home theater system plugged in. The coffee table had a laptop and a tablet on top, but otherwise the rest of the tables were mostly empty – a lone table mat on the dining table, the remotes on the side living room table, a basket with fresh fruit on the middle table of the kitchen, and three floral arrangements scattered around.

Evelyn took the laptop and tablet as she welcomed her guest. “Come in! I won’t bite.” As Armando explored the place, she reappeared without her purse, moving towards the fridge. “Anything to drink? Or perhaps something to eat? You must be starving.”

“I...” He was tipsy, but not fully drunk. “I’m alright, ma’am.” He was overcome by the strong floral scent all around, seeking its source. “Nice home you got, missus Evelyn.”

“Miss, Mr. Armando. Unmarried.”

“I apologize.”

“Sit down!”, she said, as she poured orange juice from a carafe into a glass. “Here”, she said as she gave him the glass, while elegantly sitting on the sofa. “I’m sure you must have many questions, no?”

“Yeah. You... You must be rich, right?”

“Perhaps not excessively wealthy, but enough to own this complex – and several of the cars downstairs.”

Armando found the claim strange. For someone so elegant, the cars run the gamut – from a used Toyota, a purely run-down Daihatsu that he feared was stuck in place, all the way to the elegant white Mercedes-Benz she drove him in. Other than the last one, he didn’t picture Evelyn driving any of these.

“That’s still more than enough money”, he pointed out.

“True”, she said, relaxing, her legs crossed. “Now, I’m quite sure you want to know my proposal, but before that, I think it’d be best if we knew each other a little bit more...intimately.”

Armando almost choked on the juice. He lowered the glass down, carefully. “I...heard that carefully, right?”

“Indeed”, she purred, flashing her pearly-white teeth.

“And by ‘intimate’, you mean--”

“Mr. Armando, I must confess that I’ve been dreadfully bored for quite some time. This is the first time I take anyone here, for once – I live a rather private life, after all. I often spend more time at my other businesses than enjoying the pleasures of life. I was wondering if you would keep me company, at least for one day.”

Armando tried to understand the meaning behind Evelyn’s words, but she didn’t give him a chance. She taunted him, her hands subtly lifting her cleavage. “Don’t tell me you aren’t interested in this supple body, Mr. Armando. The moment you saw me, you were interested in me.”

“I...” He breathed hard, his temples beginning to sweat. “I’ll admit I did.”

“And of all those people there, I chose you.” Evelyn stood from the sofa, approaching the young man. “Tell me something, Mr. Armando. Would you like to see more of me?”

“L-like?”

She sat down on the armrest, extending her hand upon his neck. “My breasts. They’re large and delicious, aren’t they?”

He gulped. “Y-yeah.”

“And I bet you’d love to run your hands on this large, fat ass...”

“Ma’am, I’m starting to feel uncomfortable.”

“Mr. Armando...” She slid into his lap, leaning her neck close to his nostrils, intoxicating him with her perfume. “I haven’t felt the touch of a man in years. I appreciate your gentility, but I don’t seek a gentleman right now.” She grasped his hand and slid it over her dress, until she dug his fingers deep into her legs. “Feel it”, she said as she rubbed her labia on his fingers. “It yearns for a man.”

“Y-you’re serious, right? N-no takebacks!?”

She mounted before him, smirking impishly. “No takebacks. If you satisfy me well, perhaps we may go for an encore...”

Perhaps it was the alcohol on his blood, or the smell of her perfume, but Armando was far too aroused. Evelyn smothered her breasts into his face, and every last bit of restraint was gone. He grunted, grinning, and she immediately dug her tongue into his mouth, all while rubbing her unmentionables on his groin...

--

Evelyn moaned and groaned as she felt Armando’s member deep within her. Now on their fifth time – for, he found, she was insatiable – he felt more comfortable with the idea of them having sex, and that led her to experience utter bliss.

Armando didn’t expect to enjoy this so much, however. The kiss and her perfume were just the gateway, but as he saw her naked body, his libido sprung into action. He feared the sag of her breasts would be unbearable, but despite their size, they fell naturally and felt incredibly soft. Without her dress, Evelyn’s waist bloated, though the flabs of fat spread around never felt grotesque. But it was when she took her hand to grasp her large, soft hips and immense ass that he slowly lost his inhibitions – and his doubts.

For a woman in the midst of middle age, Evelyn was perfect. His eyes were fixated at her, his hands and lips lusting hungrily for her soft, supple and barely wrinkled flesh.

He nibbled at her neck, and as he heard her moan of pleasure and felt the rush in her body, he felt the need to go deeper. This was a completely different experience from what few times he had sex with another woman – the prostitute his father paid for him to “come of age”, the fellow high school student that wanted to lose her virginity before they ended their senior year, the very blonde sorority sister that had him for a night as part of her pledge, the senior co-worker that offered her body in exchange for his silence only to be part of those who betrayed him at the end - and very enlightening.

All these previous experiences were uncomfortable at first. The prostitute, for one, was too quick and methodical, and while he enjoyed it, she didn’t seem to. The fellow student never asked for him again, and while she claimed she enjoyed it as he did, they never tried again. The sorority sister’s time was a disaster, as he felt she was feigning the act, and he heard afterwards that the moment would be the ‘peak’ of his entire life, which devastated him. And as for the co-worker, though it didn’t end up on that first try, the betrayal was more than enough to sour him.

Thus, his first time with Evelyn was awkward. He lacked confidence, and feared he wouldn’t please her – but she was very talkative, and her seductive tone soothed him. She was also very frank, for while she felt spasms of excitement, she wasn’t able to achieve climax. She comforted him, though, and guiding his fingers deep into her vagina, she taught him where and how to please her. With a gentle smile and caress, she urged him to try once more – and like magic, that third time was definitive for them.

Enough to try a fourth time – this time, and after allowing him to rest, with her standing before the mirror as he thrust her from behind.

And now, a fifth time, where she asked him to be rougher, and he complied. He couldn’t get enough of her lustful climaxing face, and as they panted and stared each other in the face, any doubt of a sixth time was dispelled as soon as she begged. “M-more, Armando!”

“I-I don’t think I can handle one more time, Miss Evelyn. I can’t feel my legs.”

“Neither do I, but y-you don’t have to stick it on me. I want to see how your tongue works.”

Armando grimaced. No woman ever asked him for fellatio, but he felt disgusted at the idea of tasting his own semen. “I-it’s alright. I... I think we should...”

Evelyn pushed him aside, holding herself by the nightstand as she struggled to step into the bathroom. “Let me clean up for you, then. I so desire one more time feeling you, mon cher.”

“Miss Evelyn, be careful. You can’t stand well--”

“I just need to gather my strength, young man. This is not my first time, and I doubt it’ll be the last.” Indeed, as soon as she spoke those words, Evelyn regained some of her lost strength, and with firmer pace, she moved into her bathroom, closing it.

Armando stared at the roof, wondering what was her proposal. Was she asking him to be her sexual partner? Everything pointed at her as a wealthy, elegant woman, and he certainly didn’t mind engaging in occasional sex if it meant having his needs covered.

But the rest gave him enough time to think. He didn’t feel comfortable with the idea of her keeping him only to satisfy her urges. He still had dreams to fulfill. Returning to college – somehow – and finishing his degree; become a citizen, with a steady job and a good house. Feeling as if he was worth anything, rather than return to his native land in disgrace, not even with a complete degree to his name.

Was it a wise choice to become her sexual partner – her personal gigolo, if anything? Could he negotiate – perhaps accepting her help, but only to lift himself by his bootstraps and start again? But, what if this first meeting was a prelude to something else?

Those thoughts would have to wait, as Evelyn reappeared at the room, lusting for more. She laid in bed, her legs spread, smiling at him. “Mr. Armando, whenever you want.”

“Miss Evelyn... I think it’s time to speak about your proposal.”

“You’re impatient... I see you’re worried. But, perhaps if you please me once more, I may be a bit more...receptive to your counter-proposal?”

“W-what counter proposal?”

“I see in your eyes that you wish to negotiate. I give you the opportunity to sweeten the deal, but I desire more of you. Would you please this aging woman and give me one more moment of pleasure, mon cher?”

His hesitation paved way to agreement, and though he was still uneasy with the idea, he dug his mouth into her labia and thrust his tongue deep into her cavity. She must have been very eager, though, as she immediately began to moan in her – as he would later know – native French. “Ou! Là! Juste là! C'est l'endroit...”

--

Armando was mounted atop Evelyn, panting in exhaustion after unloading once more. It was the seventh time, but he wanted more of her. Yet, after that last request, it was Evelyn herself who declined. “That’s... That’s enough, Mr. Armando. Time to talk.”

“R-right...” His groin was in pain, but he felt it was worth it. He tried to sit, but Evelyn pushed him to lay, and simply sat beside him.

“You had quite a bit of pent-up desire with you, Mr. Armando. It seems you have some experience.”

“Yeah... I had.”

“You did very well. I certainly enjoyed our time together, and I wouldn’t mind if we repeated it.”

“About that...” Armando sat on the bed, his back to the wall, recalling what he thought during the rest. “I was thinking, and given what we shared just now--”

“Mr. Armando, my proposal is not related to that whatsoever. Think of this as an additional benefit. I hope that, when you finish hearing it, you don’t hold anything against me.”

“Why would I? I mean... I think I know what you want to propose me, but--”

“Let me guess. Given your hesitation after I returned, you’re uncomfortable with having sex with me, or being my sexual partner altogether.”

“Not exactly. I was just thinking how we met. About...why you were interested in me, and not anyone else.”

“You’re handsome, for one.”

“Perhaps, but...” Armando paused, sure of the reasons why she chose him. “Also needy.”

“If that's what you think... Then, you may be correct.”

“I see.”

“What troubles you, Mr. Armando?”

“I don’t feel comfortable being...well, paid for sex. I pride myself on being independent – I guess what I should say is, I don’t feel comfortable living off from you.”

Evelyn exploded in laughter. “Oh, dear, no! As I said, sex is but an additional benefit. I’m thankful, however, that you came clean with that. If that’s what worries you, then... No. I don’t want to repay you for sex. I was thinking of a partnership, perhaps.”

The news took Armando by surprise. “A...partnership?”

“Yes.” Evelyn stood from the bed – after resting her legs for a while – and moved around as she explained. “Though, I wish to apologize if I’m taking advantage of your situation.”

“How?”

“You’re in dire straits, young man. Poor, jobless, and the situation regarding your migration status... I understand you’re desperate, and I admire your desire to stand up for yourself.” She stopped, her face turning into a frown. “Though, now that I think of it, you were the victim of deception, no?”

“What do you mean?”

“Your friend. The one you thought of as your friend, I mean – the one that got you the job.”

“Ah, right... Yeah.”

“He lured you with the promise of a steady job and a future. And I see you want to make a future of your own. Am I right?”

“Yes, Miss Evelyn. My dad taught me to stand by my own, but he also taught me to be thankful to people who help me.”

“Your father’s a very wise man, Mr. Armando. I’m sure you must be proud of him.”

“I am.”

“Does he still live?”

“Yeah. With mi ‘ama, back on their neighborhood.”

“I see...” Evelyn’s face wracked further. “What made you move here?”

“Studies. Though, mi ‘apa said that I shouldn’t think of Mexico anymore. They’re not exactly poor, but they felt I wouldn’t be able to live properly there.”

“You said you studied on Berkeley by means of a scholarship, but you never finished. What was your specialization?”

“Dual. Management and accounting.”

“I see...” Evelyn sat down, though remaining distant. “Mr. Armando, I want to apologize for dragging you to my house by these means. I want to come clean, as my proposal is...unusual, but it involves some deception. I don’t want you to think of me as a monster.”

“Why would I? I mean, I understand your concern, but--”

“That’s not the reason, young man.” She sighed, unwilling to stare at him. “What I did was exactly what your friend did – a promise of stability and safety. Perhaps you thought I wanted a sex partner, someone I could provide for – a ‘sugar mommy’, as you said – but you’re wrong. That doesn’t mean I haven’t taken advantage of you – and for that, I wish to apologize.”

“You haven’t taken advantage of me, miss Evelyn.”

“I have. And in a very cruel way, even.” She finally turned around, her face wrinkled and withered by her sorrow, though still remaining as beautiful as ever. “I deceived you, I took you into my bed, without telling you who I am.”

Armando was worried. “What do you mean?”

“Mr. Armando, regardless of what you think of me after I tell you the truth, I want you to know that this doesn’t make you any less of a man.”

He shivered. “Miss Evelyn, are you implying...?”

“I also want you to keep my secret. Don’t tell anybody about this – no one. I beg of you.”

“Miss Evelyn, I don’t understand. Are... are you one of those trans women or something?”

“In a way, yes.” Evelyn saw Armando shudder and retch, causing her pain. “It’s more than that, though. Perhaps if I show you, you’ll understand.” She stood up, her back towards Armando. “I didn’t lie to you about one thing, though.”

“Wh-what?”

“My name really is Evelyn de Thiel.” As she said those words, she grabbed her teeth and removed them, revealing very realistic dentures she dropped into a jar with viscous water. Then, she dug her nails into the back of her neck, scratching her skin. To his horror, Armando witnessed as Evelyn tore her skin apart, from the edge of her hair to the waist, revealing more skin within. She turned around and tugged the outer layer of skin apart, after taking a deep breath, and from her face emerged a thin, balding man in his late forties spitting a tube of flesh from his mouth and nostrils, before tugging the outer layer’s arms from his. The man had a small gut but was otherwise sweaty and pale, his skin rosy altogether from very small red dots that could only be noticed at closer examination. As he pulled the outer layer’s groin, he revealed a very limp dick and skinny thighs with stray hairs. The only thing that remained of the voluptuous woman that shared a bed with him was her eyes within the man’s own, and the lump of soft flesh laying on the floor.

Armando broke into tears, full of anguish and ire. “What’s the meaning of all this!? You’re...you’re a man!?”

“As I said, don’t judge me as a monster. I apologize if I deceived you, but I was in need. You have all the right to be angry, though.”

“Who... Who are you supposed to be?”

“Dr. Evelyn Renaud de Thiel. And... apologies for deceiving you.”