Thursday , December 8 2022

So You Wanna Be an Escort? Part One: Martha’s Excellent Orgasms

Martha woke up one recent morning to an email that could in no way have been legal. Addressed to her personally, the anonymous note said several unnamed friends had recommended her. They thought she had the necessary qualities to take advantage of a service that would connect her with potential clients who were willing to pay well for a fun evening and blissful night. The email claimed it was an opportunity for her to exercise creativity, give and receive pleasure, get out of her routine, and make some cash. If she responded favorably to this note, they would periodically send notice of potential meet-ups. For the ones she accepted, she would dress sexily and show up at a hotel bar, ready to spend the night. The client would pay $1,000 cash, all of which she’d keep, since clients pay the service separately.

If she wasn’t interested, she’d never hear from them again. But if she wanted to take the next step, all she had to do was say yes and answer a few questions. On an impulse, she hit “reply” and typed “yes.” Would she like to be matched with men, women, combos? She chose the fourth box, “Surprise me.” Were there any sex acts she wouldn’t consider, so don’t ask? She thought for a moment, then typed “Golden showers,” hoping she didn’t need to spell out that if piss was unacceptable, shit was doubly so. Were there any erotic activities she’d welcome that clients might be afraid to request? She did enjoy a good spanking, whether over a knee or tied to a bed, and she said so. Real name or pseudonym? She typed, “Gigi.” It was easy to remember and sounded like a sex kitten, even a little hookerish. Then she clicked “send.”

Before you judge either her morals or prudence, you need to know she was ninety percent certain this email had been written by her husband, Bryan. Over the past fifteen years their marriage had gone from daily wild fucking to monthly mediocre rolls in the hay. Once she’d been eager to push the envelope on how many orgasms she could achieve in a session. Now she couldn’t remember the last time she’d experienced le petit mort. Her husband had suggested more than once that they spice things up with role playing. She hadn’t seen the point. “Why play a game? Just come over here and fuck me.” But now she realized that’s exactly what they got: “just fucking.” If he was willing to go to the trouble to create this elaborate set-up, the least she could do was give it a try. And if the email wasn’t from him? Well, you only live once…

A week later another email arrived, proposing a meet-up Friday night in a downtown hotel bar. Bryan had already told her he’d be away then for a work trip, and the hotel was one they’d frequented. Her confidence that it was him went up even further. Neither of them said anything about it, of course.

On Thursday she went clothes shopping in some local boutiques. Not being twenty-five anymore, she wasn’t sure what she could pull off. One shop had a poster with their sexy outfits worn by models who are often referred to as “plus size” (but really should be called simply “women”). What first caught her attention was the fact that the models looked like her. What closed the deal was the twenty-something man who was staring at the photos. She could tell he was mentally jerking off. If she’d had a little more gumption she’d have tipped him to watch her try on outfits and give opinions, but she wasn’t ready to go there. Yet.

As it happened, the sales girl eyed Martha’s choices and gave an enthusiastic thumbs up to the second one. It was a red wraparound dress in clingy fabric that offered tasty views of her sexy legs and voluptuous breasts. She suspected the sales girl may have been mentally masturbating as well but wasn’t going to ask. Martha had been trying the dresses with her shoes off. Finally the girl glanced at her bare feet and said, “This dress begs for fuck-me pumps. Begs.”

At the appointed time on Friday, Martha maneuvered surprisingly well in her towering heels and found a seat at the hotel bar, as the email had instructed. She ordered champagne. After ten minutes, her confidence that her pimp and client were both Bryan started to wither. At that moment an attractive man about ten years older than Martha, wearing a tailored suit and natural tan, took the seat next to her and boldly made eye contact. The email had allowed for this possibility. It instructed her not to wear her wedding. If someone other than the client hit on her, she should go with the flow. When the client arrived, they’d deal with it. It could be fun. She’d know the real client because the opening line would be, “Aren’t you a friend of Monica’s?”

The guy who sat beside her didn’t know the line and wasn’t the client. Unfortunately, before any of that registered, what went through her mind was “ShitShitShitNotMyHusband!” The man read it in her face. Even though she tried to shift into friendly banter, the damage had been done. He excused himself with an obvious lie about having a meeting and disappeared.

She ordered another glass of champagne and took a generous mouthful. She felt, rather than saw, a man slide into the chair beside her. Then she heard the magic words, “Aren’t you a friend of Monica’s?” She smiled and looked at him. Bryan. The email said that if upon seeing the client she chose not to proceed, she’d say “Monica and I aren’t speaking, and she knows why.” Otherwise she’d say “Monica and I are close.”

Her smile broadened as she assured him that she and Monica were good friends. He caught the bartender’s eye and asked for “what she’s having…and another one for her.” She introduced herself as Gigi. He said his name was Hunter. Hmmm, she thought. Not bad for a character in an erotic novel.

The email warned they should assume they were being overheard whenever in public. Since their activity was, strictly speaking, illegal, they should be sure not to mention it. The effort to make small talk about anything but sex when that was their reason for meeting created a deliciously erotic tension between them. “Hunter” explained that he worked in tech and was in New York for meetings.

He slid an envelope across the bar. “Monica wants you to have this,” he said. As instructed in the email, she excused herself to check the contents. In the women’s room she opened the envelope to find ten crisp hundred dollar bills and a key card. Now, she knew this money was theirs. She’d logged into their account this morning and, truth to tell, felt a little pissed to see the money gone, even though she knew it would go right back. This morning she focused on practical things like, What if an automatic payment hits the account while it’s out? Now, though, all she could think was “I’m being paid to fuck.” She rubbed her thighs together and felt a sticky spot growing in the thong she’d chosen to complement the outfit. She’d always considered herself a feminist; now she wondered if she was actually a “do-me” feminist?

She went back to the bar, where she and “Hunter” sipped their drinks. After a few minutes, she was buzzed and loose. A little worried that another drink could make her unequal to the task ahead. That wasn’t the problem. Right then he leaned over and asked if she was ready to go. She nodded. He tapped the envelope with the key. “Room 1915. I’ll be right up.”

She hoisted her bag. “Nice to meet you, Hunter,” she said, loudly enough for others to hear.

He gave a little wave. “Great meeting you, Gigi. I’ll say hi to Monica.” Then he called for the bill as she walked out, all eyes on her in her sexy dress and sexier attitude.

Riding the elevator up, Martha found the warm, wet spot between her legs growing with each floor she passed. She let herself into the room. A king sized bed took up most of the space. A bottle of champagne in an ice bucket graced a side table. On the desk, a silver platter displayed a paddle, a bottle of lube, a penis-shaped vibrator, and a box of condoms (the latter for effect only, she assumed, because no way would she ask him to wear one).

She disrobed, laying her dress carefully over the back of a chair. Then she pulled a silk teddy from her bag and put it on. She struck a sexy pose on the bed to wait. The mirror confirmed that the teddy hid nothing. Perfect. Then it dawned on her that, much as she admired the graceful curve of her feet capped by her blood-red pedicure, this outfit would be sexier with the shoes on. She slid into the pumps and posed to highlight the dangerous stilettos.

At that moment, “Hunter” knocked once and stepped through the door. Seeing her, his face lit up. She stood to embrace him. His hands roamed her back and ass over the thin fabric. She rubbed her silk-clad crotch against his leg. He sighed. “Oh my God.” He took a step back to admire her. “You really do get what you pay for. Gigi, I could tell you were a pro the minute I walked into the bar.” His huge smile indicated that he meant “pro” as a good thing.

She reached down to squeeze his hardening cock through his pants. “You’ll find I’m worth every penny,” she cooed. Corny dialogue? Check. Women-as-whores talk that she’d normally find offensive? Check. She not only didn’t mind the sex talk but found it gave her confidence. Taking him firmly by the shoulders, she sat him on the bed and stared down at him like the alpha bitch she felt like. “I need you naked. No arguments.”

She slowly and deliberately peeled his clothes off him, pausing to stroke and admire aspects of his body as they were revealed. He wasn’t twenty-five, either, but this evening she found much to appreciate. When his clothes lay on a pile on the floor, she sat on his lap and kissed him deeply. Their tongues writhed around each other.

“I have a confession,” he murmured. “You’re my first escort.”

She flashed a lascivious smile. “Don’t worry. I have plenty of experience for the both of us.”

“I want you to tell me something….” He hesitated, took a deep breath, then spit it out: “What are the wildest things you’ve done in bed with a client?”

Fortunately the email had prepared her for this line of questioning. It cautioned her to avoid mundane talk of job or family and emphasized that inquiry about her sex life was fair game — first time, memorable escapades, etc. She was free to answer as herself or as her character. To that end, it suggested she create a fantasy journal. She’d intended just to jot down a few notes but found when she got going that details bubbled up from her imagination like water from a deep spring. She was ready to answer his questions. On her own terms.

“I’ll tell you about one client tonight,” she said firmly. “Your choice. How about the guy who hired me to suck him off while he was on his phone closing a business deal? He said having a woman’s mouth on his cock made him feel invincible. I couldn’t let him come until he said, ‘It’s a deal.’ Or how about the guy who paid me double but promised not to touch me? Catch was he wanted to watch me have sex with his wife. She was hotter than he was, so…yeah…that was a good night. The last special on tonight’s menu is really fresh — a twenty-six year old virgin I fucked a couple days ago. His friends pooled their cash to get me to initiate him.”

She wondered whether Bryan realized he was literally licking his lips as he listened to her speak. That wasn’t the only effect she had on him. No surprise his cock stood at attention. More interesting, though, was the look in his eyes. They glistened with the kind of horniness she hadn’t seen in years. She knew in her gut (let’s be honest, groin) that her eyes had the same gleam.

“Why so stingy? How ‘bout all three?” he asked.

She strode over to the desk, balancing on her high heels and waving her nearly naked ass. Lifting the paddle from the tray, she gave an order. “Lay back.” He did. “Roll over.” He obeyed. She smacked his bare ass with the paddle. Twice. Maybe three times. She was a little surprised to realize how much she was getting into it. His skin glowed red. Was that sound he made a whimper? “That’s for being greedy,” she said. “If you want more stories, hire me again.”

He sat up, gingerly placing a soft pillow under his ass. “Okay, sorry,” he said. “Just asking.” He thought for a moment. She loved how seriously he seemed to be weighing his choice. “Since this is my first time with an escort, tell me about the guy you showed the ropes.”

She smiled as she mentally reviewed the details she’d made up for that one. She’d found that writing her fantasies down made it feel almost as if they’d happened in real life. “Good choice,” she cooed. “Would you like me just to tell you, or demonstrate as well?”

His eyes got wide, like he’d just won the lottery. “Demonstration, please,” he murmured.

“The young man’s name was Kyle. First I warmed up his cock.” As she said that, she took his erection into her hand and started pumping. “To fuck a client properly I need to have the feel of him. The taste.” She lowered her lips over his penis, slathering the head with her moist tongue. She moved gently up and down as her tongue swirled around him. He groaned. Next she licked his cock up and down like a lollipop. Then she kissed her way from the base to the head and plunged it deep into her mouth. He tossed his head back, sighing and swearing simultaneously.

She rocked back on her heels and let him pop out of her lips. “Kyle said it felt great, but if he came in my mouth he’d still technically be a virgin. I asked, ‘Who says you’re only gonna cum once? The first time’s always too quick.’” She flicked her tongue on the tip of his cock, making him groan. “Do you find that, Hunter?” He nodded. “What that young man needed was a long, slow fuck,” she said, drawing out the words so they sounded deliciously dirty.

She sucked him into her wet mouth and went to work. She hadn’t done much of this particular activity lately but was relieved to find that cock sucking was like riding a bicycle: you never forget how. She teased him for a couple of minutes before he groaned and started pumping his sperm down her throat. She swallowed every drop and licked the shaft clean.

He panted like he’d run a marathon. She found that a tad unfair, since she’d done all the work. She climbed up behind him on the bed and encircled him with her legs. He turned to stare right at her red hot center and the growing dark stain made by her own juices. She pulled aside the thin strip of fabric that enveloped her crotch, revealing a clean-shaven pussy. It was something Bryan had never seen. “Hunter’s” mouth dropped open.

“I told Kyle if he expected to get head he had to be able to give it. That young man needed lots of instructions. Let’s see if you do.” She placed her hands on his head and pulled his mouth down to her pussy. She knew her husband could find his way around a clitoris. The fact he could eat her to a screaming orgasm helped make their sex lives at least tolerable even in the worst times. Tonight she goaded him like a beginner. “Right there. No, there. Put some life in it. That’s it. Yeah. Yeah. Fuck, yeah.” She kicked off her shoes and rubbed the soles of her feet up and down his torso, seeking every once of sensation. “I want your fingers inside me! Deeper! Shove one in my ass! Oh my fucking God. OH MY FUCKING GOD!” She exploded in her loudest, most convulsive orgasm in years.

After a minute, in a hoarse voice she said, “Yeah, that’s what Kyle did. Only he got a little more life into it,” she added with a wicked chuckle. “Course, we still had to take care of his little virginity problem.” She pulled “Hunter” to his knees and guided his cock between her legs. He rubbed the tip against her clit, which was slick with her cum. The light touch made her shiver. She placed her hands on his butt and applied steady pressure as he slid inside her. She squeezed her pussy around his hardness. Of course she knew it was her husband inside her, but she also felt the thrill of taking a new cock for the first time in ages.

He started thrusting, pulling out nearly all the way and shoving into her with purpose. She clawed at his back and moaned. With each thrust, her pitch got higher and volume louder. He varied his pace and changed up his angles, driving her crazy. Good as it felt, she desired more control. He was nailing her so fiercely all she could do was receive and enjoy. When his dick popped out on an over-enthusiastic thrust, she took advantage of the moment to flip him on his back and mount him. “My turn to fuck you, buddy.” She slid down his pole to the hilt. Remembering she was telling a story, she added, “Was what I said to Kyle.”

She rode him as hard as he’d ridden her, then slowed to a teasing dance. She bounced her wet pussy lightly on the tip of his prick, then took him in deep and rotated her hips like a corkscrew, rubbing him over spots that hadn’t felt a dick in ages. She wanted to feel him shoot his wad inside her, but since she’d just drained his balls with her mouth, he seemed ready to go on all night. Fortunately she knew the magic position that almost always triggered his orgasm.

She dismounted. His look of dismay turned to a smile when she spun onto all fours and offered him her luscious backside. He took his cock in his hand and stroked it before he guided it into her wet tunnel. Every thrust drew a hoarse cry from deep in her guts. She reached back between her legs to rub her clit. Between his hard fucking and her own fingering, she soon burst out in her second orgasm of the evening. Her strong contractions squeezed his dick out of her pussy, but he grabbed her ass and shoved back in. She felt him plough even deeper than before. His fierce pumping as her spasms kept rolling triggered his own second orgasm. “Oh, Christ!” he screamed, as he poured his seed into her belly.

They collapsed on the bed and lay panting. After a minute, she turned toward him and propped her head on her hand. “Did you enjoy that, Hunter?”

His head lolled back. “Worth every fucking penny,” he murmured. She peeled off her teddy and lay against him, running her fingers up and down all his smooth places. She felt wonderfully satisfied and lost in a daze. As a consequence, she didn’t know how long it had been when she realized he’d fallen asleep. As a couple they’d always embodied the cliche that great sex makes men sleepy as hell and women awake as fuck. She mulled her options, but the contented smile on his face made her decide to leave well enough alone. Plus she knew he slept like the dead.

She found the remote on the bed table and turned the TV to one of the hotel’s porn channels. It would entertain her until she fell asleep and also be a fun thing for him to notice when he paid the bill. She took the vibrator from the tray and whiled away the time in orgasmic bliss, falling to sleep as the first rays of sun hit the windows.

She woke at 10:07, alone. Breakfast waited on a tray. A note from him said, “Best night ever. Going to give you a five-star review.” That’s right, she remembered. The email said that each was supposed to send in a review that would be shared with the other. His note went on: “Check out is 11. Hunter. PS Can’t wait for next time, whore.”

“Me, too,” she thought. “Fucker.”

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