Thursday , December 8 2022

So You Wanna Be an Escort? PartTwo: Come Again, Martha

That morning in the hotel room, Martha felt nothing if not naughty. She ignored the check out time and luxuriated in a bath until noon. Then she took her bag and fished out the jeans she’d packed in order to avoid a walk of shame in her sexy dress. She’d bought the jeans at the same boutique, though, so they were form-fitting and did wonders for her ass. The t-shirt the sales girl had recommended did the same for her breasts and showed just enough skin above her waist to entice. What she’d forgotten were shoes. The skinny jeans and fuck-me pumps combo did attract some attention in the lobby. C’est la vie.

Bryan didn’t come home until the next morning, sticking to the business trip story he’d told her. In fact he texted her a couple of updates from wherever he was supposed to be. When he did return, neither of them spoke about Gigi and Hunter. They did, however, open a bottle of wine with dinner and skip dessert to fuck like bunnies into the wee hours.

The next day in her office, she got another email from the anonymous service. It was “Hunter’s” review of their encounter. He got the details right and made the experience sound nearly as steamy as it had felt. She wrote hers, praising him as “a truly great cocksman,” and sent it off. Her only surprise was how his review ended. She’d finished by answering the question “Would you entertain this client again?” with a hearty “Fuck, yeah!” His review, on the other hand, said while he’d enjoyed himself immensely, the experience inspired him to bring that passion back into his marriage. So, no, he wouldn’t be booking Gigi again.

She knew he was being thoughtful. After all, he was the one who’d wanted to role play. He seemed to be saying it had accomplished all he’d hoped. Gratitude was her expected response. They could, as she used to tell him, “just fuck.” But, damn, she wanted to meet up with him again like strangers and screw themselves senseless. The game had touched something in her that not only hadn’t come out in years, maybe it hadn’t even been there when she was younger and sex was a lark.

So she closed her office door — something she should’ve done earlier, by the way, since neither of their reviews was exactly safe for work — and wrote to the “service.” She said what a pleasant time she’d had on her first assignment. She understood that Hunter was not going to be a repeat client but wanted them to know that she was more than open to other bookings. “Surprise me!” she wrote, and hit “send.”

Bryan said nothing about the exchange for the rest of the week. Nor did she. On Wednesday she got an email from the service asking if she could meet a different client the following Saturday. For a couple of days she waited for Bryan to “happen” to have another business trip that weekend. No such luck. She was emailing with him, wasn’t she? What if the service turned out to be a real thing he’d hired on a one-time basis to act out his fantasy? She could be getting in over her head. Finally she told him she’d be away overnight Saturday to meet with a potential client. Hearing herself, she added, “For my graphic design studio!”

He smiled. “What else would it be for?” They both laughed. “Unless you’re starting a side hustle…” he added as he walked away, chuckling. She admired how well he portrayed your basic clueless husband from the softcore porn films they’d watched back in the day. She just hoped it was, in fact, acting.

Saturday morning she was back at the boutique, this time purchasing a midnight blue number that managed to put her boobs on glorious display while sticking to the kosher side of the fine line between classy and slutty. The same sales girl helped her out. Martha left the shop convinced the girl was headed in the back room to masturbate.

Waiting in the hotel, sans wedding ring, she got the attention of a series of well-dressed men. One with the courage to approach introduced himself as Marcus and offered to buy her a drink. This time she remembered the drill. Since he didn’t mention Monica, she let herself enjoy the flirtation while waiting for her “real” client to arrive. She told Marcus she was Gigi and wondered to herself if his name was any less bogus than hers. He told stories that made him sound like a world traveler. Who knows, maybe he was telling the truth. He was clearly hitting on her. He touched her hand a few times. Casually, of course.

After a while she glanced around the bar and saw Bryan, sitting at a table, staring at them. She flashed a wicked smile. He took that as encouragement to come over. “Excuse me,” he said. “Are you a friend of Monica’s?” She gave the proper response and invited him to sit.

“This is Marcus,” she said, introducing her new friend and would-be one night stand.

Bryan reached out to shake his hand. “Liam,” he said. Martha smiled at the name he’d chosen. How often had she told him if she ever had a free pass she’d use it on Liam Neeson? “Liam” ordered more drinks for all of them. Marcus did his best to be friendly. “Gigi” flirted shamelessly with both men. Her mixed attentions brought out the boastfulness in both. Marcus’s global adventures became even more dramatic. Liam held forth about the Silicon Valley company he’d founded and for which was in New York to broker a lucrative sale.

The experience reminded her of long-forgotten college parties, when she and her pals would vie to see who’d go home with whom. She knew feelings could get hurt, but also that it was exciting.

She remembered the night she’d spent flirting with a guy from her history class. He had good reason to think he was getting lucky until an ex of hers showed up at the party well past midnight. One steamy dance changed the game. Martha and her ex stumbled drunkenly upstairs and found a spare bedroom where they could fuck the night away. When they padded down the stairs the next morning clad only in t-shirts and shit-eating grins, they woke the guy from last night, who turned out to have slept on the sofa. He never spoke to her again, and she felt like shit. Sexually satisfied shit, but shit just the same.

In fairness, she remembered that her karmic debt had been repaid on another Saturday night when she thought she was going to hook-up with a guy that her friend Amy swore was the best sex she’d ever had. Amy also said that now she was engaged to somebody else, their relationship was over. Martha was on her way to his car after the party when his phone rang and a sobbing Amy begged him to come over. That was that.

She was mulling over those memories from before she met Bryan when she realized “Liam” had slid an envelope in front of her. “Monica wanted you to have this.” She swept it up from the bar and excused herself to the bathroom. In the stall she counted out the money, not because she needed to, of course, but because it excited her as much as it did the first time. She wondered about the look on Marcus’s face as she’d left the bar. What did he think the envelope was?

When she got back, the two guys were sitting silently. As she climbed back onto her bar stool, Marcus stood and said he had another appointment but was glad to have met her. “And Liam,” he added a little glumly. After his rival’s departure, “Liam” went on chatting about the fictitious business he was there to sell and to extoll the wonders of the beaches of Northern California, where he expected to spend his care-free, well-heeled days after the sale closed. She appreciated the trouble he’d gone to in making up the fantasy and asked encouraging questions, building up his manhood like a good escort should. Finally he asked quietly if she was ready to go. She nodded and got up. “I’ll tell Monica hello,” she called out, stealing his line from last time.

She walked through the door on her way to the elevator and was surprised when Marcus stepped out. “Oh, shit,” she thought, worried it might be a scene. He began by apologizing if he’d made her uncomfortable. She said he shouldn’t feel bad and started chattering about how Liam happened to know a friend who…. He interrupted her in a voice that was not unfriendly but no bullshit either. “It’s just that if I’d known you were a pro, we could’ve gone that way. I don’t judge. I’m sure you’re worth it. I guess this Liam guy booked ahead. Lucky him.” Just then the elevator came. He walked away. She stepped on, feeling a little shitty but also hornier than ever.

When “Liam” came through the door to the room he found her sprawled on the bed, naked. He stared at her for a moment. Then he sat on the edge of the bed, still fully clothed. She reached over to undress him, but he interrupted with an order: “Over my knee.” His tone brooked no disobedience, and she was there to please him. She lay over his lap, face down, her ripe ass exposed. He reached over to the tray and picked up the paddle. He brought it down on her ass with a loud thwack. She gasped. He did it again. This time she made no sound. When he did it a third time she sighed “fuck” under her breath.

“Who was the man I found you with tonight…after I booked you for myself?”

“I told you. His name’s Marcus.”

She felt another smack on her ass. “Does he have a big dick?” he asked.

“I’ve never seen him before. Like I said.” Another smack. “Ow!”

“Don’t say ‘ow.’ And don’t give me attitude.”

Two more smacks, and her ass was getting sore. So he was going to play it that way, huh? “Gigi” could do the same.

“The service lets us do that, you know,” she said, hitting just the right tone of brattiness. “We can let extra clients buy in, if both agree.” She was blithely making this shit up, but the email hadn’t said they couldn’t do it. Of course, Bryan had been the author. Would “Liam” call her bluff?

Instead, his voice took on a new tone. “Have you done that before, Gigi?”

The arousal she heard in his voice gave her the right answer. “Yes.”

“What was it? Two guys?”


“Did they both fuck you?”

“Not until I’d sucked both their dicks.”

“Where did the first guy fuck you?”

“In the hotel.”

She felt another smack on her tender ass. It took her a moment to catch her breath so she could speak. “In my pussy.”

He slid a finger into her sopping wet hole, massaging her pussy walls and flicking past her clit. Her butt gave an involuntary wiggle.

“Did he have a big cock?”

“Oh, yeah,” she said. She made it sound like she was talking about a delicious steak. Practically drooling. “Huge.”

She felt another finger slide into her. Then another, and another, until it felt like she was getting a well-oiled massage on her most private parts. Fisting was an experience she’d never tried. Her office buddy Emily swore by it, at least after a second martini loosened Emily’s lips. As his fingers worked their way around her dripping cunt, she started to appreciate Emily’s perspective.

“Where did the other guy fuck you?”

Martha was lost in the feeling and didn’t respond. He pulled his hand out of her cunt with a pop and slapped her ass with his sticky palm.

“Ouch!” she cried. So he spanked her again. “Ouch!” And again. Then she remembered the game. She sucked in her breath after his next blow but didn’t say a word. He gently massaged her ass.

“Where did the other guy fuck you?”

“In my ass.” He circled her anus with his finger and then slid it inside. Her pussy juices had him oiled up as if he’d used a whole bottle of lube. He penetrated easily. No pain. Even so, she quietly hoped he wasn’t going for four fingers. “He had a smaller cock, so it fit just right,” she said, trusting he’d catch the hint.

After a minute he withdrew his finger from her anus and resumed massaging her butt. She started to turn over, but he wouldn’t let her. She felt his thumb push into her ass. It was bigger than his finger but so well lubricated she felt only a nice, sensual pressure. Meanwhile, his fingers sought out her clit. He created a circular motion between his finger and thumb as they skillfully manipulated her ass and clit. She felt her climax rising deep inside and knew it would be a doozy. Grabbing for a pillow, she buried her face just as she let loose with a screaming orgasm that, if unmuffled, would’ve brought the house detective running.

When the waves of contractions slowed, her body felt loose as a rag doll. “What the fuck?” she wondered. How did he just give her the earth-moving feeling of a full-on threesome with only one hand? She really did marry a stud.

She slid off his lap onto her knees and started opening his belt. He reached up. She assumed he was taking off his jacket. Instead he pulled out his phone. “Here’s what I need you to do, Gigi,” he said. “I have to call a guy to finalize the deal I told you about. I want my cock in your mouth the whole time. Keep me sharp, you know? Don’t let me come until I say ‘It’s a deal.’ Got it?”

So now he was stealing her lines. Well played, “Liam.” She opened his pants and took his cock deep in her mouth. He pretended to dial the phone. At least she hoped he was pretending. He could’ve gotten a friend to play along, but what would he have said they were doing?

She ran her tongue up and down his cock as he proceeded with making his deal. He drew out the “negotiations,” obviously enjoying himself. She’d never spent this much time with his cock — or anybody’s — in her mouth. She enjoyed getting creative with how she varied her techniques. When she felt him about to come she’d back off momentarily, blowing on his shaft and balls with her cool breath. She reached inside her own pussy to lube her finger so she could slide it into his asshole. His eyes got wide, but he didn’t miss a beat in his “deal making.”

Finally he called out, “It’s a deal.” She took his cock deep in her mouth while tickling his balls with her fingernails. He cried out as he spurted and she swallowed eagerly.

This time neither one was sleepy. They spent the next hour pleasuring each other in ever more creative ways. Both lost count how many orgasms they enjoyed. At last they fell asleep in each other’s arms.

Bryan is one of those people who wakes up at the same time no matter what time they fall asleep, so “Liam” was gone when she awoke. This time she didn’t bother with the porn channel. She just played back the night before in her mind as she used the vibrator to get herself off one last time (or two) before check out.

She couldn’t wait to write the review.

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