You sat across from me wearing what I assumed was one of your nicest evening dresses. It was pink and shimmering in the sun as the afternoon sun shone through the windows in my open office. You were made up tastefully. I always thought you looked like the kind of woman who wouldn’t need my matchmaking services. But, you weren’t looking for just any lame boyfriend – you never had trouble getting those. I had counted on that.
“I trust that you have read, thoroughly, my client’s terms and conditions.” You smiled and nodded, and your charm started to dawn on me. Normally, I can tell when one of my female clients is lying, but you were different. In that moment I started feeling like this match might work out exactly as intended. I like generating repeat business, but you made me think of the bigger picture.
“He has read mine?” you asked. I assured you that he had. It’s been my experience that men, even very particular ones, never fucking read the contracts. After the first few years of doing this work – without a partner – I started reading the contracts to them to save myself from future headaches. “And he’s fine with all the key points? I expect my independence.”
“He’s agreed to all of them, point by point,” I said. “He often travels for work alone,” I began, “and understands that you would want to do the same. As we discussed, and as you agreed, both solo vacations would take place while he travels for work.” You nodded, visibly recalling our negotiations about that point. “And he has already signed a purchase agreement on one of you preferred city apartments.” You smirked, and it’s like I could see the machinations churning behind your eyes. “He had no requested alterations.”
“And I had none for him,” you assured. For almost every other woman who’s walked into my office seeking a significantly older, more successful potential husband, I would have assumed that this would be the final one-on-one meeting. Not you. At least, I hoped it wouldn’t be. It’s not hard for me to remain professional, even with the most desperate women who meet with me.
My eyes never traced along the edges of their dresses over their thighs or down between their breasts. I never stumbled over words or lost focus during the “past sexual experiences” interview, no matter how dirty and enticing the stories were. My eyes never wandered from tattoos, piercings, or scars in the “bodily inspection.” For what it’s worth, yours were both dirty and enticing. I never saw dollar signs in my eyes, anticipating that any of them would ever be back at my glass table. I never hoped I could steal a match from my male clients. And, most importantly, I never felt my cock swell in my pants. None of that was true with you.
I always put in a clause about the “termination of a relationship” and how neither I, nor my business, are responsible for unforseen circumstances. Consequently, I refuse to match anyone who expects traditional fidelity with anyone else who I think could present an issue. But, never has anyone explicitly asked me, “Are there clauses specific to future indiscretions or infidelity?” You uncrossed and recrossed your legs when you asked.
“No,” I replied, “there are no specific clauses.” Trying not to show you my own interest in you, I leaned back and pressed my tie down along my shirt. “Why do you ask?”
“I’ve had experiences,” you replied. Your face didn’t say that you’d been cheated on; in fact, it didn’t give much away at all. That, in and of itself, intrigued me.
“Experiences we should have discussed in the ‘sexual experiences interview?'” I asked.
You studied me. “Either you never suspected anything,” you said, “Or he’s into non-monogamy of some kind.” I said nothing, and did my best not to give you any indication either way. We were now in a whole new interview, and you were succeeding. “Maybe you think he’s aloof and wouldn’t notice or care.”
“You asked him for solo vacations,” I replied. “I would imagine that he pictured you getting fucked by a tanner, younger man on a beach at least once.”
“Imagine? He did?” you asked, erotic skepticism hung in your voice. “Or you did?”
I have prepped myself for these sorts of scenarios. Even if I was fascinated by you, those preparations wouldn’t give away the game. “If I said that he had?”
“Good,” you replied, “It’s likely to happen.” Your tone was both sensual and matter-of-fact.
“And, if I said that I had?” I asked in the same plain tone as I had asked the previous question.
“You may have cum to the thought, I think,” you said. “But I would imagine that a man in your position as a matchmaker would call this whole thing off if that was a problem.”
“I’ve done it before,” I said. “Many times.”
“Then why are you and I sitting here alone instead of the three of us?”
“I have a feeling that you have more ambitions than merely marrying a rich, middle-aged businessman.”
“I do,” you replied. “I aim to get fucked on a beach. And in that apartment he bought for me. And I aim to keep him the whole time.”
I scratched my beard contemplatively. “What if you didn’t keep him?”
“Why would I dump him if I can have everything I want?”
“Because I think I can offer more than that,” I said. You scoffed, expecting me to try to take you for myself. “I have a proposition for you,” I said opening the file far to my left. I wrote the document in that file when I started this service as something of a business fantasy. I’ve always hoped to pull it out, but I’ve never had the right woman in front of me before.
“Don’t try to sell me on something,” you said, sounding like you were thinking that some sort of jig was up.
“I’m not going to sell you,” I said, sliding the contract to your side of the table. “You’re interesting and clever. I was just going to let you read the proposition for yourself.”
You looked at me, puzzled, as I leaned back. You noticed that I hadn’t touched by cock, bit my lip, or did anything else suggestive. Your curiosity piqued, and you grabbed the pages. You read methodically. A cruel, fascinated, opportunistic look came over you. You leaned in a way that let your nipple peek out of your dress.
“How does this affect my current match?” you asked.
“It doesn’t,” I replied. I could damn near feel your sensual excitement ramp up to its highest level.
“You expect me to cheat?” You asked, pointing at the contract. “You want me to break up other relationships and marriages, be bait willing to be photographed, and you’ll pay me to do it?”
“Pay you?” I asked rhetorically. “You’d be my business partner; you’re paying yourself and our firm.”
Your eyes darted back and forth like you could see the future and were scanning it for potential downsides you were uncomfortable with. You smirked, and I assumed that meant you saw none. “What do you get?”
“Besides pay,” I began, “I have my perks, but I never expect you to cross any uncomfortable line with me.”
You thought for a moment and looked at the pen you used to sign the male client’s contract with. “A matchbreaking service?” you said to yourself. You pushed your chair back and stood up. In that moment, I thought, only for a moment, that you would storm out the door. I feared that I shouldn’t have shown you that contract, or that I’d fallen into a trap of sorts.
“I’m quite comfortable with you,” you said as you slid the straps of your shimmering pink dress off your shoulders. The dress fell to the floor revealing your slender build, slightly tanned skin, and handful-sized breasts. The tattoo reading “Rest and Repose” in Latin stood out from your right collarbone, and the sun bathed you in a sexual glow.
You leaned forward, grabbed the pen, and signed the document. Fuck, my cock was hard and I could swear that I heard the ink dry as I lost myself gazing into your eyes. I’ve wanted nothing more than I wanted you in that moment.
“Is this one of the perks you hoped for?” you asked, standing back up and showing yourself off to me. You rubbed yourself all over.
“I had hoped for this,” I replied, “yes.”
“When will you take your first photos of me?” you asked.
“When we break up your match: not until you’re ready,” I replied. “When we break up someone else’s… How soon do you want to get started?”
“How soon do you want me to be sucking your cock while you watch videos of me cheating with a married man?”
I knew you would be a fantastic business partner in that exact moment, and, since then, you’ve never disappointed.