Tim and I continued to chat, a little bit each day. Sometimes our chats were quick, casual, and non-sexual. Other times they were extremely sexual and ended up with me begging him to allow me to cum while he told me what he wanted to do to my wife.
After a couple weeks of this he said he had a very serious question and asked me (in chat) if I wanted to make this a reality or if I was just interested in online. I was impressed with how careful and not pushy he made what could have been a difficult conversation. He said many husbands liked to fantasize, sometimes show off pictures of their wife, and he said that for many people keeping it a fantasy was the right logical and sane choice. At no point did I feel any pressure.
But he said had to be up front about his interest and desires and those desires were to fuck my beautiful wife first in her wedding bed and then everywhere and any time he wanted. He said that since we had started talking he stopped looking for other options and had not considered any other sexual partners because cleanliness and STD tests were very important... another reminder that he would only have her without a condom. (I would later find out that he kept a roster of male friends who felt the same way so that he could share his conquests bareback, and another, larger, group that had interest in group sex. The larger group he couldn't vet quite so carefully, so condoms were used there, but I'm getting ahead of myself...)
He said he was willing to wait and be patient if I needed time, but just asked that I be honest if I knew for certain I was not interested in real time "play". So I was honest with him. I told him how much I wanted this. That it was all I had fantasized about for years. He already knew that the only way I came was watching porn and that nothing turned me on as much as seeing a cock cum inside a woman. He knew about my own inability to perform sexually, and that nearly all of my sexuality had come to revolve around the cuckold fantasy... and he also knew that I wanted to make that fantasy a reality.
But I also told him Michelle was very conservative and had only one boyfriend who even played with her tits before me, that she was a virgin before (and after) her wedding night, and that my cock was the only cock she had known. I told him as much as I wanted this I didn't want to destroy our relationship and that scared me... that I was worried about jealousy and other emotions, worried that reality would obviously not be the same as fantasy. Many things scared me but yes I wanted to make this real.
He said that honestly the seduction was a big part of the drive for him--seduction of a couple. As much as the final goal for him was complete ownership and use of a couple, not just a wife, (he was always reminding me of that and yes thinking about what I might end up doing also scared me more than a little) he said transforming and changing his couples was maybe the biggest turnon of all... taking a conservative, sexually inexperienced woman and making her into a raging whore... that was true ownership that excited him. In fact, even after doing this in real life with three couples, he said he had stroked himself to many orgasms thinking about doing these things to my wife.
So we agreed to meet in a bar for drinks and to discuss this in person. That meeting wasn't incredibly eventful but it was an important step to making it real. In person he was large and had an easy charisma. I could see that he probably had no problems finding sexual partners at all but he confessed his precise tastes made things a little more challenging for him and that he wasn't really interested in one night stands.
He did ask a lot of very specific sexual history questions at the bar. It was strange talking about these things in public. I don't think anyone knew what was going on but I was convinced everyone was watching us as we sat at a table in the back of the crowded bar late in the afternoon. My cock was often rock hard, and I knew I had leaked precum through my pants in a spot that would be obvious to anyone looking.
He asked a lot of detailed questions about our sex life, her sexual history, and what she liked. He asked very specific questions about how often we had sex and what had happened. I told him that I had had trouble staying hard and had tried viagra but it didn't really work. He asked if I was hard when I had been chatting with him late at night or if I get hard watching watching porn and I said yes. He asked if I was hard right then in the bar, and I admitted I was.
He asked if I thought there was any chance I was gay or bi and I said I honestly didn't think so. This became a very non judgmental and open conversation and he did give me something to think about--it really is shades of gray and maybe not black and white. He said the fact that I was open to sucking his cock, swallowing his cum, and getting fucked like a girl did probably mean I had some bi inclinations. I didn't know what to say but my cock was throbbing and dripping hearing him talk about that so casually.
He said he could see I was having trouble focusing and he sent me into the bathroom and told me to go cum. I went to the bathroom--this was not the first time I had cum in the bathroom in recent weeks. Many days at work I had to do the same thing... relieve some pressure... so I could focus on work. But this time I was amazed at how soaked my underwear was with precum. I rushed into an empty stall, locked the door, I came standing in the stall and shot my load directly into the toilet before cleaning myself up, wringing the precum out of my underwear, and then headed back to our table.
It was hard to meet his gaze when I returned because we both knew exactly what I had just done--what a very strange feeling. We talked a little bit more about possibilities and how I might want to see all of this happen. He said for him there was a range of things and arrangements that could interest him but he had been clear about what his non negotiables were: he would have her without a condom and would frequently cum in her pussy, he would like to have all of our holes but understood we were both anal virgins (hearing him say that made me forget to breathe), he expected us both to serve, and he was into some, maybe more than a little, dominance and humiliation.
He asked me not for the first time what my limits were and if I had really thought this through. Though we had discussed it before we both knew it was something I needed to consider so anytime it came up he said to give it some serious thought. And I had considered and had looked at some links and references he had given me so I had a better answer. I told him that I thought bathroom play... urine or poop... was out for either of us. He said he felt the same way... that good sex to him was sweaty and dirty sometimes but he didn't have any interest in bathroom play and in fact preferred his partners to have enemas before anal. In fact, he said, if we do this you should have several enema kits on hand the first time we meet.
So with that settled I said I didn't think any body modification was ok. He said how about if I have her get her nipple pierced? And from my cock's reaction I said i guess that would be ok. He said have you ever thought about her having a queen of spades tattoo somewhere not everyone can see it? Ok maybe that is ok too. This limit stuff is harder than I realized.
