Chapter 11: Grand Plan. Videos. Volunteers

We’d been back from St. Croix a week when Amber had an unusual situation develop. She got a call specifically asking that she verify that she was the ‘sexy little brunette’ on the Sensations Escort Service website. She confirmed that she was in her cute and coy way, even teasing about whether the male caller wasn’t also entranced by blondes and redheads, thinking of Kat and Edie.

The deep male voice chuckled, “No, I’m a brunette freak, plus you look like a girl I went to school with twenty years ago. I never had the courage to date her, but I had more fantasies about her than you can imagine. I said ‘had’ but I still have them. You are the answer to a prayer.”

“Well, my name is Amber. What’s yours?”

“Oh, I’m sorry. My name is Roger Moore, and I’m not or any relationship to the actor of the same name, although he was much older and I think he died not too long ago in any case. I’m fortyish, in reasonably good shape, and head my own software company as a majority shareholder. We deal in specialized software systems to support manufacturing operations. The website said you were interested in IT.”

“Well, Roger, what can I do for you? And, yes, I find the whole tech area fascinating.”

“I am newly single after a ten year marriage, and I have to make an important trip that I need a pseudo-wife for. I’m wondering whether you’d be interested?”

“More details, please,” Amber coaxed in a playful tone.

“OK. The trip starts on April eighth, and would go until the week of May fifteenth – so about five weeks. The travel would involve one long trip hopping from initially Australia to Indonesia to Japan to China and then to Russia before returning home. I have to negotiate deals in each of those places, hopefully, and there’d be all the interpersonal rigmarole with wining, dining, and entertaining to woo the people I want as potential business partners and customers as I piece together several large deals.”

“And my role would be?” Amber teased.

“My pseudo-wife. I need female companionship. I need a partner who knows how to behave in an international setting, including with people who you won’t understand a word they’re saying because of the language barrier.”

“Will I be expected to be THE entertainment for your potential business partners?”

“Nope. If anything they will be less likely to offer ME female companionship because YOU are present and wife-like or girlfriend-like. They might still make the offer, and if you’re interested we can decide on the spot whether to accept or not. I’ve been in those situations, and the women are usually outstanding, just as I feel you likely are.”

“How do you know about me?”

“Oh, yes. I asked my friend Martin Powell. I believe you know him and just spent some time with him down in the Caribbean.”

“I did. We did. I’ll have to thank him properly next time I see him.” She giggled at the sexual innuendo of her comment.

Amber thought, “Let me see if I can move around and shift to some of my partners the meetings and assignations I have in that timeframe. May I call you back or do you want to give me a day or so and call me again?” Amber made sure not to put any confines on her new mark. She also suggested they have a ‘date’ ahead of time to check out their chemistry, instead of finding they didn’t have any and then had to spend five weeks putting up with each other.

Roger willingly gave her a phone number and instructions about how to ask for him personally. He said, “I love the idea of a ‘date’ in the near future. As it is, I can hardly wait to see you. I know you’ll be just perfect. You’ve already exceeded my expectations.”

Amber’s next call was to Mike. She explained about the request.

Mike was silent for a long time, to the point that Amber felt compelled to fill the void.

Amber said, “Mike, I love you. I think of this as some kind of test or a hurdle to our moving forward, but it’s a decision that we have to make together. Roger’s request would have me away for about forty days. I’d make eighty-thousand dollars, and probably a sizeable tip if I act as a good companion to Roger’s business dealings – something you know I’m capable of doing and being. If I’m to use sex to help his deals, he knows the price goes up. I’ve not done ‘international’ before, although I have been to London for a week.” She paused and asked, “What do you want your girlfriend to do?”

Mike made some coughing noises and finally spoke, “Baby, I love you. I will miss you like crazy and I will be as jealous as all hell about this Roger Moore character. My big concern is losing touch with you and that we’ll drift apart. It’s bad enough with just my needing to be in Boston a lot and my crazy schedule, plus the two of us together going in different directions make it nigh on impossible to be together as I want to be ... but then this trip is only for five or six weeks.

“I’ve been to most of the places Roger wants to take you. From your description of your duties and role with him, besides the obvious of being his night-time companion, it sounds like you’ll have some time to be a tourist and that you’ll also be meeting, entertaining, and schmoozing with important business people in each of those countries. That’s a very rare opportunity.

“So, what do I want my girlfriend to do? I want her to accept the ‘assignment’ but please come back to me and be MY loving girlfriend, and maybe more. I also want you to tell me what you’re doing and where you are? Lots of communications.”

“Do you want me to be telling you the sexy stuff?” Amber ignored the implications of his comment about their relationship.

“Especially the sexy stuff,” he emphasized. “I don’t need more than a sentence or two about your travelogue, but I want pages – with pictures – about the sexy stuff; the who, what, why, where, when, and how. I want to know everything. I want you to make me miss you; sorry I ever let you go, and things that will make me impossibly horny. I want you to tell me true stories that will have me jerking off because the visual imagery of what you’ve done is irresistible and demands satisfaction of my arousal. Can you do that?”

Amber laughed, “I can try, Mr. Horndog. Maybe we can even Skype once in a while, or I can send a video I’ve taken, or maybe even do a live video porncast of some kind. I promise all those things, and I will miss you.”

Mike said, “Good. Now call Roger back and accept. I have a month to enjoy you before you go, so I’m going to be storing up lots of memories of you and me together doing fun and sexy stuff together.”

“You still picking me up for dinner and whatever?”

“Six-thirty, babe, depending on the winds the jet runs into on my way down to Florida. Bring your overnight bag. See you later at my hotel. I love you. I really love you.”

Amber noted that Mike had never been so effusive in declaring his love for her until that telephone call. There was even an oblique reference to her possibly becoming his wife. Maybe there were going to be some positives in their relationship from her forty day absence from Mike’s life; well, except for all the sexy things she could think of to send him or do to torment him each day.

Amber had her first ‘date’ with Roger a week later. He flew into Sarasota from Kansas City, took a room at the Ritz Hotel, and she met him for cocktails in the dark paneled bar in the top-end hotel. A quick glance informed her that she wasn’t the only working girl in the bar meeting a ‘date.’ Of course, also in the bar were Kat and Edie at a separate table, all but ignoring the pair, but keenly curious about the man that would cut such a pricey deal with an escort. She noted that they surreptitiously took pictures of the pair.

For her part, Amber had started to swoon as soon as her ‘date’ appeared at her table asking, “Are you Amber, per chance?”

Roger made a good first impression: his smile brightened the room; his handshake was warm and inviting; his dark eyes undressed and seduced her; and his welcoming words were inclusive and friendly. Amber felt at ease instantly and hoped she presented as well as he did. While a little chunky from too many good meals and glasses of fine wine, Roger declared that he was also an exercise freak that loved to jog and spend an hour in the gym most days.

Roger was what one might call a ‘go-getter.’ His eagerness about life and every facet of it poured from every pore of his handsome body, and later she learned that eagerness plus his competence in engineering, computers, and technology had allowed him to develop a thriving software company that he wanted to see attain an international presence.

He hoped that Amber would be joining him for the trip and the journey he was on; she confirmed that she would. Over drinks, the new couple went into their backgrounds a little deeper with each other. Like her roommates, Amber had become a skilled interviewer, able to get people to talk more and reveal a lot about themselves, including their fantasies, dreams, and vulnerabilities.

For his part, Roger obviously wanted to impress Amber, so spent considerable time responding to her questions by talking about himself, his business, and the upcoming trip and the hopes for what would happen in each country. Amber was more impressed by his attention and efforts to woo her, than by any specific feat he’d accomplished in his career.

Fundamentally, he was marketing his company’s prowess with software and large-scale business and manufacturing systems. He was still in the process of setting up meetings in the various countries, but the trip was coming together nicely, he said. Each weekend during the Grand Trip was for them to change to a new country and again start his marketing efforts anew.

Amber pleasantly surprised the handsome executive by applying her interests in computer systems and information technology. Her questions were not the naïve and simplistic ones, but complex that showed understanding of how IT was used in business for both routine operations as well as competitive advantage. The more Amber revealed, the surer Roger was that he had to have her on this trip.

Amber took the opportunity to outline some of the business contributions she’d made in her business consulting work, carefully omitting that most of it had been done incidental to being an escort or Mike’s girlfriend in a group sex setting. She never mentioned any company specifically, but told enough case studies so that Roger could see how she might be able to help him market and sell his company’s capabilities. He was so glad she had these stories to tell because they complemented what his company was trying to make happen for their potential customers.

After dinner in the expensive new restaurant atop the nearby Westin hotel, the couple made love for a couple of hours. While Amber had started to think of the engagement as a normal business ‘fuck’ it quickly became clear that both of them were putting more of their souls into the ‘date’ than just their lusty bodies. Amber relished the idea of being with this man for forty days or so. What a fun and even romantic assignment.

Amber also took the opportunity to see how her phone might work as an audio recording device. She surreptitiously put the device on Record and left it in the side compartment of her purse that she set on the dresser in Roger’s posh hotel room.

Roger proved to be an attentive lover. He took his time, emphasized foreplay with Amber and made sure she was ready for his advances. He truly made love to her breasts to the point Amber had a small orgasm, and then went down on her with enthusiasm she’d rarely experienced with a normal ‘date.’ When they finally coupled Amber put her best effort forward to please Roger, giving him a large ration of dirty talk that he obviously relished, and then making him change positions with her several times whenever she felt him nearing the edge of the orgasmic cliff.

Roger told her, “You are a wonderful woman. I like you on top of me – what do they call it, cowgirl? I like to fondle your breasts, to look at the expressions in your face as we fuck, to see your body moving over me, to feel your tits on my chest when you kiss me, and to watch my cock moving in and out of your cunny. You are one hot babe. I made the right decision in picking you.”

Amber teased, “Oh, I had competition?”

Roger laughed as he pumped into her body, “Not really. Martin knows my preferences in women. He assured me that you would be perfect. I guess you and he ... got together when you were on St. Croix.”

Amber teased, “Got together? I’d say we fucked each other’s brains out several times. As he must have told you, there were others around. We had no end of cocks and pussies to choose from. The week was a bit of an orgy.”

“He said you were outstanding, and he’s in love with your roommate, Edie. Is that right?”

“Yes, and Edie is also in love with him, but Martin wants her to keep working as an escort.” She decided to tease him a little, “Would you mind your girlfriend or wife continuing to work as an escort?”

Roger thought a moment, “You know, I think it would be really hot. I can imagine someone like you being devoted to me, but out fucking other gents. Very hot and sexy.” Amber was surprised as yet another male she knew opted for a slutty girlfriend.

Roger continued, “I’m not the jealous kind. My ex-wife had a string of affairs while we were married. I knew about them, even encouraged her. Later, I had a couple of flings, but that’s all they were. It made the sex that much better for the two of us.”

“Why divorce? It sounds like you both enjoyed the open marriage.”

“Ah, the world does not revolve around sex unfortunately. I guess overall we could chalk it up to significant personality differences. We’re still friends, so I’ve used the term ‘happily divorced.’ We’ve even continued to have occasional sex. We’re both just single and living apart.”

“Just out of curiosity, why didn’t you ask you ex to go on the trip with you?”

“For forty days? We’d kill each other,” he laughed. “We’d last about a day, and then the sarcasm would start. The jibes would start a few days later, and then the insults and verbal abuse. The taunts would get so bad we’d want to do physical damage to each other. We were pretty vitriolic in the end. I figure that process might take a week or so. THAT’S why I didn’t ask my ex-wife.” Roger continued to laugh, but Amber could tell there was more than an element of truth in what he’d said. So far, Amber thought he was pretty laid back.

“Damn,” muttered Amber. “The recording sucks.” About all she could hear of the recording she made of Roger and her fucking the night away the previous evening was a few occasional words, lots of muffled moans – mainly her, and then her muffled orgasmic screams.