I'm a happily married man. I have a wife and two kids. I love them all. She is usually very GGG and has indulged pretty much every kink I threw at her. (Except for male chastity devices.) We started the relationship actually pretty open about what we wanted. I basically told her I love bottoming. Nothing mixes like weed and anal. I'm not gay—at least I really don't think I am—but I like getting fucked. We peg often. Enter my long standing fascination with transgender women.

This interest, which I've kept hidden from literally everyone I've ever met, was discovered by my wife when I forgot to close a porn browser. She didn't know how to take it at first. She wasn't mad. It was more like she was sad because she couldn't be what I wanted. She eventually started asking me questions and it basically came down to me wanting to get fucked by a real cock but without the dude part. She processed this and eventually began to seem really understanding. She went as far to say that it must be really hard to feel trapped in a relationship with someone you love when you want something else. She made the decision that she would be totally okay with me going to see an escort and if I enjoyed it we could come up with some rules to abide by. For a few days I thought I had hit the jackpot.

But... this feeling of dread just washed over me. I did some research and quickly decided who would fit the bill in terms of looks and local. (I live in a world city so the choice is seemingly endless.) But as I got closer to the idea of initiating contact with a trans escort I started to think about what it could mean to our relationship. It made me have serious doubts about whether or not this was even something I wanted to do. So I began talking to my wife about it—as often as she would enthusiastically allow—and she didn't hide that she wasn't to keen on knowing specific details and that she would probably be a little jealous but she didn't want to hold me back from trying something that meant so much to me. Those words made me feel like a completely selfish piece of turd.

And now I'm at a standstill. I have a hall pass to try something I've always wanted but something internally is telling me to slow the fuck down. How can I make the right call?

Throw Me A Lifeline

Your letter reminded me of a story I shared with another reader—a woman whose husband gave her permission to be with another man one time—and I'm going to share it with you too...

I knew this straight couple. They were good together, they loved each other, and they had a strong sexual connection. (Spoiler alert: my use of the past tense.) The woman was all about monogamy, but her boyfriend had always wanted to have a threesome. She didn't want to be the reason he never got to do something he'd been fantasizing about since age 13, so she told her boyfriend that if the opportunity ever presented itself, he could go for it. So long as the sex was safe and he was honest with her, he could have a threesome one time.

The opportunity presented itself, the sex was safe, he was honest with her—and my friend spent a week ricocheting between devastated and furious before finally dumping her devastated and flummoxed boyfriend. During a drunken postmortem, my friend told me she wanted her boyfriend to be able to do it but didn't want him to actually do it. She didn't want to be the reason he couldn't; she wanted to be the reason he didn't. So her permission to have a threesome "one time" was a test (one he didn't know he was taking) and a trap (one he couldn't escape from).

I'm not saying your wife is setting a trap for you, TMAL. Unlike my old friend (full disclosure: my old ex-friend), I don't think your wife is consciously testing your love. But I fear that accepting your wife's offer—actually using that hall pass—will devastate your wife and doom your marriage. And you sense as much too, TMAL, which is why you're hesitating. You have the wife's okay to experience something your external organ has always wanted to experience—getting some actual dick in your ass without having to get in bed with an actual dude—but an internal organ is telling you to slow the fuck down. That internal isn't your gut. It's your heart.

And here's what your heart knows that your brain doesn't yet: you've done a terrible, terrible, TERRIBLE job of explaining this shit to your wife. When she said, "It must be really hard to feel trapped in a relationship with someone you love when you want something else," it doesn't sound like you stopped thinking about your dick/their dicks long enough for that statement to register. Nor does it sound like you fully processed this: "She was sad because she couldn't be what I wanted."

Dude.

You needed to drop everything and reassure your wife that she is what and who you want. She needed to be told—she was begging to be told—that you love her and that you don't feel trapped in your marriage and that this—your fascination with transgender women—doesn't negate your fascination with cis women or your attraction to this cis woman you married.

She needs to be told—again and again—that, yes, there's this other thing you've always wanted to experience, TMAL, but you'd never seriously contemplated experiencing it IRL until that open browser kicked off this conversation. It was a fantasy that you were content to keep a fantasy. Not pursuing it was a decision you made before you met your wife. Which means you didn't give up what really wanted to be with her. You didn't settle for her. She was what you really wanted. So you're not trapped—you're right where you always wanted to be. You're with her.

You say you're at a standstill, TMAL, and want to make the right call. You have a hall pass in your hands and the wife's permission to do something you've always wanted to do. But your wife's permission wasn't offered joyfully or in the spirit of sexual adventure or because there's a discreet need of yours that she can't meet. Your wife handed you that pass because she feels inadequate. I'll bet you that right now the memory of every pegging session is a torment to her—she likely thinks you were fantasizing about the woman you really wanted each and every time she pounded your ass.

So long as she feels this way, TMAL, a standstill is the right call.

Keep talking to your wife. Not about when you're going do this, but about whether you're ever going to do this. And not doing it, ever, needs to be on the table. So long as your wife sees your interest in being with a trans woman as a negation of who she is (your person) and who the two of you are (a sexually adventurous and sexually exclusive couple), actually using that hall pass presents a mortal threat to your marriage.

You might get there eventually, TMAL, if you can listen as well as talk. But for the moment... you need to stand down and standstill.