Chapter 16: Dinner for Four

Diana babbled happily away in the elevator up to the fortieth floor of the Intercontinental hotel where there was a high-end restaurant and lounge. I knew enough once we got there to ask for a cocktail table on the east side of the building away from the sun. The shades would be down on the west side of the lounger anyway to block out the penetrating setting sun.

Diana and Gordon looked impressed. I was trying to pull off my ‘suave’ demeanor, which was hard to do being almost twenty-one. Allie was twenty-one, and Gordon and Diana were each about forty years old. Our relationship with each of them was difficult to explain, and if one’s thinking was clear, was patently obvious. Gordon wasn’t there yet. Diana knew all, or thought she did.

We sat and ordered drinks. I had excellent ID, so ordered a glass of wine. We quickly got served and I let the hostess know that we also had dinner reservations under two names in the dining room. She went off to confirm to the maître d’ that we were present and wanted a combined table.

Gordon graciously asked Diana what she was ‘up to’?

She replied, “Tonight or in general? Tonight, I’m going to get my lights fucked out by Adam, just as you are going to try to do the same thing with young Amy, here.

“In the larger picture, I have decided to become the executive director of the local woman’s resource center – a place dedicated to helping abused or neglected women recover from a bad relationship situation. Since I have some training in the area, and now first-hand experience thanks to my ex-husband, I thought that would work well.” She smiled smoothly at Gordon.

There was a long silence and then she burst out laughing. “Gordon, I admire your taste in women. Amy is gorgeous. You picked well. Amy, please excuse me for outing your escort relationship with your ‘client’. Gordon, Adam is my escort ‘date’ for the night. Adam, I guess you know Amy other than in some professional way?”

I rolled my eyes. The mire of what was happening was getting deep and difficult to slog through. I spoke, deciding to reveal our situation a bit. “Yes, we’re both students at the university in related fields. We also live together ... and are kind of engaged. We haven’t bought a ring yet.”

Gordon fell back in his chair as though somebody had punched him in the chest. He studied Amy and then me. Diana was laughing.

Gordon finally asked, “Is this a set-up of some kind? A shake down? Is there a hidden camera someplace watching my reaction?”

Amy gasped, “Oh, absolutely not. It was a coincidence that Ch ... errr, Adam and I were meeting our ‘dates’ at the same time in the same location. I didn’t know you knew Diana until I saw her come over and greet you. This is a popular venue for doing that. Adam has seen his ... friend about once a week for the past ten weeks or so. My ‘date’ with you is new. I promise there was nothing else going on, except that Diana knew you and then ... well, brought us all together.” She gestured around the table.

I stepped in, “I just want to confirm what Amy said. I didn’t even plan for us to interact at all. I was amazed when Diana said she knew you, and then before I could say much she took off across the lobby to see you.”

Diana was still laughing, “Interact! I like that word. I think we should all go and interact after we’ve had dinner.”

Gordon asked in a skeptical tone, “What does that mean?”

Diana whispered loudly so others in the lounge wouldn’t hear, “I think we should all go and fuck, fuck, fuck for the rest of the evening. Gordon, wouldn’t you like to fuck Amy AND me? I know for sure that Adam would enjoy fucking Amy and me, and I’d like fucking both of you men.”

Amy quickly said, “And so would I, just to set the record straight. What do you say, Gordon?” I liked that my girlfriend was playing the course as it lay, without trying to get any fancier.

Gordon broke into a grin. “This will be all right with Connie?”

I smiled, “I’ll be sure she’s all right with it tomorrow. It may be easier to get forgiveness than to get permission, if you get my drift.”

We toasted each other with our drinks, and after we were through our cocktails, we went to our dinner table.

Our dinner conversation still was slightly stilted. Gordon was curious about what made Amy and me get into the escort business. He wasn’t surprised by our financial problems, nor when we later both confessed to also doing adult videos.

Amy even had her earbuds with her. She set Gordon up on her cellphone to watch one of the videos we’d done together. It was a short ten-minute video. Diana was next to him and also watched much of it without sound looking at the screen from next to him, but also pressing one of her breasts into his bicep.

Allie whispered to me, “That’ll get the two of them in the mood. Porn usually has that effect on people – arousal.” She giggled.

Besides arousal, seeing the video also triggered a large number of questions from Gordon about our videography and how we started in the business. Amy and I were very open without mentioning Jake’s name. We talked about the mechanics of preparing for and doing a video, and what we knew of what happened after our day or so in front of the cameras.

Gordon asked, “Are the emotions you portray in the videos real or faked – or what proportion are faked? What about your orgasms? Is the cum they show real? How do you clean up after filming?”

He remembered that we were newly engaged, and that shifted his line of questions. “Do you mind your fiancée or fiancé having sex with somebody else? Do you think that’s going to impact your long-term relationship? Will you keep doing the videos or escorting after you get married or after you graduate from college?”

He had an endless stream of questions, many of them were thoughtful and some made us laugh. We did shock him with our answers occasionally. We both kept our answers salacious and racy.

Diana explained at one point, “Gordon doesn’t want to admit it, but he is married. I’m guessing that he needs a little recreational sex when he’s away from home like this.”

Gordon nodded. “I would love for my wife to be interested in sex the way you are Amy – and apparently you Diana, but there appears to be no hope. We were like rabbits when we got married, but then she found other interests, and, of course, there are our two children.”

I asked, “Don’t you think she has a guess as to what you’re doing by staying over on a Friday night before going home?”

He shrugged. “Maybe yes. Maybe no. If she asks, I’ll be straight with her and explain that I’ve tried everything I could to rekindle her interest. I’ve arranged sitters, parents, bought her flowers, candy, jewelry, and done a lot of wooing, but to no avail. I just don’t figure in her life the way I used to.”

“Does she work?”

“Part time. She believes that we can’t be working when the children are out of school. They might need chauffeuring or homework help or guidance or something. I think the motherhood gene took over her mind when she got pregnant. She forgot about the married gene, and that atrophied away. She knew more about obstetrics and gynecology than her doctor by the time she had to deliver our first. Even he was amazed.”

Diana postulated, “OCD?”

Gordon hemmed and hawed. “Yeah, but then I’m that way about business, too. I do try to park that at the office, especially on the weekends.”

Diana said, “Sounds like it’s time for counseling.”

Gordon studied his new friend. “I guess you’re right. Our youngest has ten more years before she would leave for college. A decade at this age is a long time to try to tolerate what our marriage has deteriorated into.”

I didn’t think the discussion about Gordon’s marriage was setting the stage very well for a sex-filled evening among the four of us, or even just Amy and Gordon, so I made several attempts to redirect the conversation to something more along that line of thought.

Amy got on my wavelength and helped. “I bet you never thought you’d get to fuck a college girl AND a hot MILF on your ‘date’, did you? Can you handle two of us?” She grinned as she threw down the gauntlet.

“Oh, I think I’ll do just fine,” he lobbed back at her.

The next I knew, Gordon had two moist thongs sitting between his forks and knife at the dinner table. That got his attention, and certainly put him in the mood to hurry through dinner.

Gordon had a mini-suite with a fabulous view of the city. I knew from experience how to lead the group in getting naked, and after I took that leadership role, it didn’t take much for the sexual and romantic side of the evening to start.

I focused on Diana, since she was my client. Amy was giving a world-class blowjob to Gordon and he looked like he’d been transported to some state of nirvana. He also looked harder than a piece of rebar.

I munched on Diana’s pussy just the way I knew that she liked. She liked me to nip the skin over her mons and then down her thighs before I focused in on her labia and last her clitoris. I added fingers just before I got to her clit and putting my tongue on her hot little button was like detonating an ICBM in a thermo-nuclear war. She exploded and the pieces went everywhere in the room. Even Gordon and Amy were impressed.

Diana lay panting, sweating, and extolling my virtues as a lover. I didn’t argue, but I did hear some whispering behind me. The next I knew; Amy was right at Diana’s pussy working to bring her to the brink again. Diana went right back into orbit on my fiancée’s mouth and fingers. Gordon was stroking his shaft as he watched the sapphic interaction.

Seconds later, Gordon plunged his cock into Amy Cox’s wet and very willing pussy. She was pushed hard into Diana’s cunt, and that just drove her into another orgasm. They separated and I started to fuck Diana right where Amy could reach with one of her hands and stroke her clit as I pistoned into the older woman’s body.

Amy eventually said, “Switch.” She nudged Gordon from her pussy, took hold of his cock, and steered it right into Diana’s gaping hole that I’d just vacated. He sank to full depth on his first thrust. Diana was wide-eyed, and loved the event. She pulled Gordon down to her, wrapped her legs around his mid-section, and they started to kiss like the world was about to end and only their passion could save it.