The Escort Game Pt. 01

Martha's Excellent Orgasms

Martha woke up one recent morning to an email that could in no way have been legal. The anonymous note said several unnamed friends thought she had the necessary qualities to take advantage of a service that would connect her with individuals who were willing to pay well for a fun evening and blissful night. It would be an opportunity to exercise creativity, give and receive pleasure, escape routine, and make mad cash. If she responded favorably, they would periodically send notice of potential meet-ups. For the ones she accepted, she would put on an outfit that made her feel sexy 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 the service would be compensated separately.

If she wasn't interested, she could reply with a simple "no" and never hear from them again. If she chose to take the next step, she simply had to say yes and answer a few questions. On an impulse, she hit "reply," typed "yes," and scrolled down for the questions. 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? She 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 her prudence, you need to know she was ninety-nine 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 occasional 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 urging them to spice things up with role playing. She hadn't seen the point. "Why play games? Just come over here and fuck me," she'd said. Lately 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.

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 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 displayed posters with their sexy outfits worn by models who are often referred to as "plus size" but really should be called simply "women." She appreciated the fact the models looked like her. What closed the deal was a twenty-something man standing there 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 doe-eyed Millennial woman who worked in the shop 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 full breasts. She suspected her helper may have been mentally masturbating as well but wasn't going to ask. Martha had been trying on the frocks barefoot, and before she went to pay the woman 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, she became annoyed at Bryan for keeping her waiting, exposed to the hungry glances of other patrons, men and women alike. Her confidence that her husband was behind this scheme started to wane.

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 when it said she shouldn't wear her wedding ring. 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 so wasn't the client. Before that fact 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 mistaking her for a friend 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?" Bryan. The email had emphasized that what happened next would still be up to her. If she liked the client, she should say, "Monica and I are close." If not, she could reply, "Monica and I aren't speaking, and she knows why." The client would then be obliged to leave.

She gave him a once over and took a long pause, seeming to decide. Then she assured him that she and Monica were bosom buddies. 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. Not bad for a character in an erotic novel, she thought.

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 talk about anything but sex when that was their reason for meeting created a deliciously erotic tension between them. "Hunter" smoothly delivered a line of bullshit about how he worked in tech and was in town for meetings.

He slid an envelope across the bar. "Monica wants you to have this," he said. As directed by 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, to be honest, felt a little pissed to see it missing, 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 felt 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, loud 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 center stage. 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.

"Hunter" knocked once and stepped through the door. 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."

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 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. "I need you naked."

"Well," he said, looking flustered, "how about you...."

She laid a finger over his mouth. "No arguments." He closed his mouth and started unbuttoning his shirt.

What an Alpha-bitch, she thought. I love me.

She peeled his clothes off, 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. She just hadn't been looking lately. When every stitch lay on a pile on the floor, she sat on his lap and kissed him deeply. Their tongues toyed with each other.

"I have a confession," he said. She arched her eyebrows. "You're my first... escort."

She flashed a lustful smile. "Don't worry. I have enough experience for the both of us."

He clearly liked that. "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?"

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 from her own experience or as her character. To that end, it suggested she create a fantasy journal. She'd intended to jot down a few notes, but when she got going details bubbled out of 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 cum until he said, 'It's a deal.' Or the one 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-three-year-old former virgin. I fucked his brains out a couple days ago. His friends pooled their cash and hired me."

She wondered whether Bryan realized he was literally licking his lips as he listened. 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," 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."

"I started by warming up his cock." As she said that, she took Bryan's 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 and swirling it around the shaft. He groaned. Next, she licked his cock up and down like a lollipop. Then she kissed her way from the base to the tip and plunged the whole organ 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. "He said it felt great, but if he came in my mouth he'd still technically be a virgin. I asked who said he was only gonna cum once? The first time's always too quick." She flicked her tongue on the tip of his cock, making him moan. "Do you find that, Hunter? Isn't cumming twice in one night a special treat?" He nodded, enraptured. "What that young man needed was a long. Slow. Fuck." Her words were dirty enough on their own, but the way she drew them out was mind-blowing.

She sucked him into her mouth and went to work. She hadn't done much of this activity lately but was relieved to find that giving blow jobs was like riding a bicycle: you never forget how. She teased him for a couple of minutes before he muttered, "Christ" 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 at her red-hot center and the growing dark stain made by her own juices. She pulled aside the strip of lacy fabric that enveloped her crotch, revealing a clean-shaven pussy. She done that this afternoon, so it was something Bryan had never seen. His cock sprang back to life.

"I told him if he expected to get head, he'd better be able to give it. And I'm so nice I let him practice on me. He 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 dry 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 ounce 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 how it went." With a wicked chuckle, she added, "Only he got a little more life into it. Course, we still had to take care of his 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. "Slow and easy, stud," she said as he slid inside her. She squeezed her pussy around his hardness. Even though she knew it was her husband, she felt the thrill of taking a new cock for the first time in ages. This roleplaying thing wasn't bad.

He slowly pulled back and then thrust deep, getting faster and harder each time. She clawed at his back and moaned. Each time he plowed in, her pitch got higher and volume louder. He varied his pace and changed up his angles. She was so wet every slap of their hips was accompanied by a sloshing sound. She desired more control. He was nailing her so fiercely all she could do was receive and enjoy. She grabbed his shoulders and flipped him onto his back, her on top now, his dick still buried deep. "My turn to fuck you, buddy." Remembering she was telling a story, she added, "I said to him."

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 all the way and rotated her hips, rubbing him over spots that hadn't felt a dick in ages. She wanted to feel his spurting cock in her pussy, but since she'd just drained his balls with her mouth, he seemed ready to go on all night. Fortunately, she knew a trick.

She dismounted. His look of dismay turned to a smile when she spun around onto all fours and offered him her luscious backside. He took his cock in his hand and stroked it before guiding it into her wet tunnel. Every thrust drew a hoarse cry from deep in her gut. She reached back between her legs to rub her clit.

It wasn't long before she burst out in her second orgasm of the evening. Her strong contractions squeezed his dick out of her pussy. "Keep fucking me," she cried. "Fuck me hard!" He grabbed her hips and shoved back inside her. She felt him plough even deeper than before. His fierce pumping as her spasms kept rolling triggered his own second orgasm. He screamed and 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 over all his smooth places. She felt 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. 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. Enjoy your morning. Checkout time is 11. Going to give you a five-star review." That's right. The email said each was supposed to send in a review that would be shared with the other.

Thinking about what she'd say in hers made her horny all over again. Thank god he left the vibrator.

Stay tuned for Part Two of The Escort Game: Come Again, Martha