"I've started dropping hints about you to her," Jack told me, "but we've still got some work to do. Can you come by for a bit tonight?"
"Tonight?!" I replied, surprised. "You mean, she's..."
"No, she's away for a couple of days, Randy, but there's some more... evaluating, let's say." Even over the phone, I could hear the smile in Jack's voice. He was enjoying this, and at this point I wasn't sure which of us was more excited. Not that it mattered.
I agreed to come by; Jack had advised me to keep my schedule clear, so it wasn't a complete surprise, and as... unorthodox as this all was, he seemed a decent enough sort and I was enjoying this.
Jack had approached me the week before. He'd seen my profile on AFF and presented me with a tantalizing offer; he wanted to provide an unforgettable surprise for his wife, and he'd asked me to meet him for a drink to discuss it. I asked him about the wife, and he refused to give any details. "Not until I know for sure we're going ahead with this, but I can promise you'll be impressed."
Yes, I was flattered. Newly single at 42 (by amicable, mutual agreement), I'd been out of the scene for over a decade during my marriage. In the six months I'd been on my own (with half-time custody of our 9 year old boy), I had decided to "work on me" before going after anything. Went for a little counseling, hit the gym, and I was definitely starting to feel ready for a little fun. I'd dropped my spare tire and leaned myself down to 240 on my 6'4" frame with the help of P90X and workouts at a local MMA academy. I'd never be climbing in a ring, but my coordination was improving along with my muscle tone, and I was gaining some badly-needed confidence. I'd posted my AFF profile a few weeks before with a few, tasteful, discreet pics (and one decidely UNtasteful one; I didn't want my casual intentions to be mistaken). I'd chatted with a few women back and forth, but I hadn't found a situation I was completely comfortable with, and I wasn't desperate enough to jump.
Jack and I met for the first time at a sports bar on a quiet night. He was definitely a different physical type, maybe 5'6" and compact. He struck me as one of those wiry little fucks that would be easy to underestimate in a fight. Older than me, I figured him to be early-to-mid fifties, but active. I had a feeling he ran.
I introduced myself and he laughed "Really? Randy?" I smiled in response, "Yessir, really Randy. Take that any way you want."
We got a beer and found a quiet table. "First thing I want to make clear, Randy: I'm not gay, not bi. I'm not after your dick. This is all for my wife."
"Thanks," I said, "Won't deny the thought crossed my mind. This is a little, um, unusual."
Jack explained: he and his wife (who he still wouldn't name or describe aside from "athletic with a few curves") had been married close to 30 years, and while their kids had been growing up they'd both played it completely straight. A strong marriage, never a hint of infidelity. "Not that we NEVER fought," Jack laughed, "but I always felt VERY lucky."
Once the last of their three kids flew the nest, they traded their suburban home for a nice condo. Jack had a successful business, "wifey" had a successful corporate career, and once they were on their own they started indulging each other, tentatively looking for adventure, but together.
"So you're getting into swinging?" I asked.
"A little," Jack said, "but we're being careful. My wife arranged a... surprise for me a little while ago," the recollection made his eyes twinkle sharply, "and she went to a lot of effort. 'Due diligence', you might say."
I agreed with what he was saying. I hadn't been in "The Lifestyle", but I'd thought about it a lot, and read up as much as I could. I could understand it being a minefield, especially for a couple that valued discretion. I was flattered he'd even consider me for this.
After bullshitting about women and work for a while, I looked Jack in the eye, "You sure your wife will be into this?"
"Oh, you're her type, for sure. She's turned on by bigger guys, especially since I'm all she's had, pretty much ever. I just hope you understand, that 'due diligence' I was talking about is going to take more than a couple of beers."
"What do you need?" I asked, a little offended, "A fucking background check?"
Jack held his hands up, "No, not like that. Let's just say there are some pitfalls I want to avoid, and I hope you understand. Trust me, and let me evaluate you a bit. Nothing bad, don't worry. Like I say, trust me. If we do this right I promise you won't regret it. There's a couple of things I want to check out with you, and I'm gonna say it will take maybe a week. But it will be worth it for all of us. Really."
We shook hands, and agreed to meet at the YMCA for a workout the next night ("I want to see how much it takes to wind you," Jack said with a smile). He wasn't kidding, either. We ran a couple of miles on the track and did an interval training session, then a quick round of weights. He was in pretty decent shape, but I was stronger. I was grateful for the fight training, it definitely helped my wind. Jack discreetly checked me out in the locker room, of course. It's hard to be sure in the showers, but I was pretty confident that I was somewhat better-equipped. And I understood that Jack needed a little more confirmation that those AFF profile pics were really me.
As we left the Y, he said, "Okay, this is looking good so far. Bear in mind you're not the only guy I've ever checked this out with, but I'm comfortable with what I see. There's a couple more things I want to, um, 'evaluate'. Keep the next couple of nights clear, okay."
"Sure, Jack," I replied, shaking his hand. I respected the effort he was going to in making sure his wife's "surprise" would be a good one. Jack had explained that some of the younger guys he'd considered came across as inconsiderate and cocky (which was why he was looking at me, a guy only a few years younger than his wife), and a couple of others just seemed... off-kilter. Nothing specific, but kind of sleazy. Jack wasn't picking that vibe up from me, so he hoped I could be a little more patient.
So, two nights later he asked me over for a little more "evaluation", and I was still good with what he was doing, but when I got to his condo and he led me straight to the Master Bedroom, I cocked an eyebrow at him.
"I told you, Randy, I'm not after your dick. I've got a few puzzle pieces to fill in for you, though, and I'm going to push your comfort zone. You'll see why."
