Does your wife really sanction your activities?

Yes. Since we met when she was half of a client couple, she understood from the very beginning what I did and how good I was at it, not just the sex part, but the whole setting the tone and environment. Moreover, since she was curious, we started teaming up as appropriate, and then she eased into her own very successful escort business.

Does my wife consider my work “cheating?”

No more than I consider her work cheating. We know about every encounter we have in our line of business. See below for my rule on working with wives. The bottom line is I am not looking for another one, thank you very much. Communications and trust have been and still are the bedrock of our relationship. Look, if one day my wife tells me she has trapped some other poor bastard with her feminine wiles, then I will reluctantly wish her all the best. Will I feel like shit–yep. But her happiness is more important to me than anything else in the world. Always has and always will. I am a simple fool. Then a gain I got a very long kiss when she read this.

Have I ever worked for free?

Yes, though rarely and really only under some very extenuating circumstances. And in those few cases, see above, it was with my wife’s full consent. Best example was running into a young woman in tears in a hotel bar. Her husband just couldn’t understand she wasn’t cheating on him, so I offered to teach him a lesson. In hindsight, was it stupid? Yep, it was. It could have gone horribly wrong, especially when you read what my normal process is below. With her jealous husband waiting inside, I walked into a hotel room with his wife on my arm. Did it work out? Yes, and they became clients. But that is NOT how to do business. Seeing a theme here? Yeh, my wife does too. She calls me a charming, caring idiot.

Does she worry about things like STDs or pregnancies?

STDs. We both do to a certain extent. However, one of the luckiest things about my path, and by extension my wife’s, has been the exclusivity of our clientele. Ever since the beginning I have worked only by-word-of-mouth and the couples, or women I escort, are the only ones with which we are comfortable. And by now, we are hired by, or on retainer to, mostly high-end “landed gentry” or “young money” types. Not saying it couldn’t happen, but we take regular tests to be safe.

Pregnancies. My wife has been on birth control since forever, thankfully with no side effects. Of course, there was always a risk. And now we are both “distinguished” (cough), that’s less of a concern for her. In my case, when I was younger, I didn’t care. Cavalier? Stupid? Yep and yep. After we had kids, I got the old tubes tied, frozen peas for the win.

Are your clients typically the same age or younger?

All the above, plus older. Some of the older clients I had earlier as a young buck are still my clients. Then again, I just got back last month from taking a young (late 20s) wife to Europe for a week, sending pics and vids to her husband at a conference in Canada. It just depends.

What is the weirdest encounter I have had?

This was an easy one. This couple were repeat customers, and we had met in a room at an upscale resort in the Caribbean. While I was on the bed, getting his wife right to the edge, her husband was sitting on the couch, naked and stroking himself. Out of nowhere, he started to weep. We both looked over, and I thought he couldn’t take her being with me anymore–that happens, and I started to pull out. But his head was hanging down as sobs wracked his body. After a glance at his wife, I slid from her and walked to him. As soon as I sat, he crumpled to my shoulder and wailed, so I put my arm around him and placed my hand over his, keeping him hard.

At that point, I had no idea what might be troubling him. His wife comes back from the bathroom with a box of tissues for him and settles down next to me. Though worried, her hands worked on me. Weird, yes, but I wasn’t complaining. After a while, he gazed at us, sniffled, apologized, and told me his mother had died a year ago. He is a high-powered, fast-moving executive, and this was the first time he had some time to reflect. The grief just overwhelmed him. After another rushed apology, he dressed, told me to take care of his wife, and walked out. Later, after we were done, he returned, and we all ended up going to dinner, where they both talked of his mother while I shared some stuff about my mom. Group therapy, Tommy style. He still apologizes.

Do you have any rules that you won’t bend for clients?

Once I arrive, I am in charge. By that, I mean we have already had a meeting at some neutral location to discuss expectations. And, keep in mind that I have pretty much always received new clients by word of mouth, so they already understand the activities I offer. However, even with regular clients I haven’t seen in a while, I ensure we have a refresher meeting to clarify what will happen when I walk into the house, hotel room, yacht, whatever. Having said all that, there are often times when I am with a couple and get the idea one or the other is up for something that pushes their boundaries. For example, early in my career, I sensed the husband really wanted me to take his wife with me after I had fucked her in front of him. While she was reticent at first, when I asked him and he nodded, she was comfortable leaving with me. Not only did that become our routine, but, little did I know, that would become a fairly regular request once other couples become comfortable with me.

I am as discrete as you want me to be. If you want me to wear your wife around town, I will. Or not.

I am here for both partners. If one or the other gets uncomfortable, I stop. A little nervousness is one thing, but I can usually tell, especially by now, if one partner has changed their mind. I am there to help couples, and not ever hurt them. Then again, I broke my rule once. True story, that’s how I met my wife. She wanted to play more than her boyfriend. She stayed, and he left. I kept her ... Well, really, she enticed me, trapped me, and made me keep her.

Safety matters. I was not kidding about using safe words in the story. That was an eye-opener. For both partners. If the husband wants to call out, then he can. I work for them both. Also, I ensure locations, equipment, and activities are safe. At an outdoor event, for example, the couple liked bondage. Got that covered easy, but have you ever tried to find two pairs of saplings in the shade so the clients don’t get sunburned and close enough to restrain two people so they can see/hear each other? Oh, and not near anthills, or wasps? In that case, as in most, I also brought my own shackles, bindings, collars and blindfolds. Some folks, even with plenty of money, try to go cheap. Or just don’t know any better. It’s my job to know better.

No surprises. If I show up and things are not as we agreed, I leave. Yes, your sister-in-law is gorgeous. No, she was not part of the plan. True story. Did I play with her later? Yes, once we had all met and laid new ground rules.