The following is a prequel to my earlier post, A Fantasy.

When I first told my best friend that I might become a woman, he did not freak out. At least, he didn’t look like he was freaking out. If he was freaking out inside, he covered it perfectly. He seemed completely calm.

In our earliest conversations on the subject, he mostly found the whole idea confusing. He obviously didn’t share any similar feelings of gender uncertainty, so I had to sort of explain things from the ground up. Even though he isn’t really a “guy’s guy” in any way, he’s still a guy, and the idea of someone not wanting to be a guy didn’t seem to quite make sense to him. But he stuck with me, asked questions, and was totally nonjudgmental.

Better still, he was willing to talk whenever I needed it, and I found those conversations to be immensely helpful, because I suddenly felt known and not rejected. It was a great relief to no longer be hiding this from him.

He’s on the more sensitive end of the guy scale, and over time, I started to think that he found the whole concept more provocative than he first let on.

Because we hang out together regularly, and sometimes do things you might see a gay couple doing (such as sightseeing or just walking together and talking), he gets a little freaked out sometimes. So we have a running gag where he says, “All the people here think we’re gay,” to which I respond, “So what? Who cares?”

But there was a moment, years before I came out to him, when he was especially vulnerable due to certain life circumstances. We had had a memorable conversation in which he confided that, of all his friends, I was the only one that he could imagine cuddling with on a couch. It was a sort of weird thing to say, and it came out of the blue. Given the circumstances, I knew that he was trying to communicate that he felt safe with me, and close to me, that he appreciated our long friendship, and that it was unlike any other that he has had.

After he said it, he had paused to gauge my reaction. Back then, I wasn’t thinking about coming out to anyone, but I didn’t want to mock him or dishonor his vulnerability. My reaction was only to say that I appreciated his feelings, and I didn’t comment at all on whether something like that could ever happen.

He quickly said that it wasn’t a gay thing, and I told him that I understood completely. I’ve known him long enough to realize that, if he has any gay tendencies (like his older brother), they are pretty weak. I’ve never really sensed anything that made me think he was hiding it, or interested in men at all. I could be wrong, of course. People hide things like that all the time — like me and my gender identity. But I don’t think I’m wrong on that count. He wasn’t gay, but he felt close to me, and our relationship was mature enough that he could tell me. I took that as a compliment, and have cherished it ever since.

Practically, I had to sort of stick that little moment in the back of my mind, but as time passed after I came out to him, it popped into my head more and more. And though he never said it, I think it was going through his mind as well. It became clear to me (and probably to him) that he had sensed my femininity, without knowing exactly what it was about, long before I ever said anything to him. And though I had no reason to think he was having fantasies about me, the reverse was a different matter.

The truth is that, at some point, I had started to have sexual fantasies about him — well not exactly about him, but which included him. Like many transwomen, I had fantasies about being sexual with men, but they were always faceless men, and the acts were merely physical things which allowed me to experience myself sexually as a woman.

But over time, my faceless man got a face, and to my great surprise, it was his. And the sexual acts, rather than being the whole of the fantasy, started to give way to just thinking about kissing, and hugging, and flirting, and eventually, yes, just cuddling with him on a couch!

It was a weird, sort of backwards progression, from the highly sexual, to the highly social. Eventually, the fantasy sex became the culmination of fantasy dates, until the idea of the date became more exciting than the physicality in which it might culminate. I was shocked to realize one day that I was more aroused by the idea of an honest emotional encounter with him than a purely physical one.

I began to fantasize about us traveling together, me as an out transwoman, presenting ourselves as a romantic couple everywhere we went, and then enjoying each other romantically before falling asleep together in big hotel beds. I fantasized about just being held, or kissed, or treated like someone that he considered special. I fantasized about being his date to his company Christmas party, and attending family picnics with his grown kids and ex-wife (who he has maintained a healthy and positive relationship with). I fantasized about dressing for him, and trying out perfumes until I found one that he really liked. I fantasized about pajamas, and nightgowns, and waking up with him pressed against me. I fantasized about mornings where I got dressed for work at his house, selecting from a closet full of women’s clothes that he let me keep there, then kissing him goodbye as we each went off to work.

By the time I came out to him, he was the subject of my every sexual fantasy, and many of them didn’t even involve sex (although that remained on the spectrum of fantasies).

I have never been attracted to him physically, and I’m still not. But the idea of the emotional intimacy made me want, in my fantasies, to offer him that physical intimacy, which I then imagined enjoying quite a bit. Not being gay, and literally never having been physically attracted to a man, this whole idea actually freaked me out a bit.

Being something new to my trans experience, I told my therapist all about it. She confirmed that it’s quite common for her clients to have such fantasies. But she could tell that the idea of being a straight woman was an unfamiliar one and scary for me, so she tried to reassure me that most of her male-to-female clients identified as lesbian, or occasionally bi, after transition. She said that, in her many years of experience, it was pretty rare to find someone’s sexuality flipped by the hormones.

But I knew in my heart that I was already, even before hormones, on a path to female heterosexuality. And I actually adjusted to the idea fairly quickly because, in my fantasies, I was overjoyed to feel safe, and loved, and cared for, and known as wholly female. It was entirely surprising to me that the presence of a man might have this effect, but my imagination was, I think, just extrapolating from where I was going as a transwoman.

And then came the most powerful fantasy I’ve ever had: That he wanted to marry me. It wasn’t a fantasy that I sought, but it just sort of tumbled into my mind one day. We were on a date, only he was more dressed up than usual, obviously nervous, and took me to a very nice restaurant. About halfway through the meal, he started stuttering and stammering, and I suddenly knew what was coming. The subject had come up casually before, so it was easy to say yes. Then my fantasy would shift immediately to the Justice of the Peace, with his daughter as my Maid of Honor, and his son as his Best Man, and then he was kissing the bride — me! — as we became husband and wife.

This quickly became my dominant fantasy, to the point of excluding almost everything else. The details varied each time. Sometimes I was post-op when we married, and sometimes I was completely pre-transition. Sometimes I imagined a small church, and other times a judge’s chambers. Sometimes I imagined myself in a full white wedding gown, and others a simple off-white, satin, tea length dress (but always dressed in women’s clothing). Sometimes I saw him in a tux, other times a suit, and still other times I couldn’t see anything but his face. Sometimes I imagined the honeymoon, or just the wedding night, or even our celebration in bed right after getting engaged.

It was the imagination of these “celebrations” which actually motivated me to visit my local adult fantasy store. I’m hesitating to say what I bought, but I will admit that I bought it because I wanted to be prepared (i.e. sufficiently accommodating) in the event that someday he wanted to make love to me before I had a proper vagina (which I may never have). Subsequently, my use of that item made the fantasies even more intense, though also more emotional. I regularly began to cry while imagining him wanting me to be his wife, in every sense of that word.

In short, I kind of got “bride brain,” another very new experience for me.

The fantasies were incredibly powerful, and changed me profoundly. I realized that being dressed as a woman caused me to think in different ways, and consider things that I would never consider any other time. I already knew I was trans, but now I also knew exactly where I was headed. It brought me great joy, and not a little bit of terror. I wanted to admit this all to him, but had a hard time even imagining the words I might use. The possibility of rejection was simply too great.

As time passed after I came out to him, our friendship remained stable, essentially unchanged by the revelation. Well, unchanged in most ways, but I saw a new tenderness in him whenever the subject came up. He didn’t want to talk about it all the time, though he never shied away from the subject when I brought it up. He asked questions, and even gave advice. He quickly accepted that transition was inevitable for me, and started to get used to that idea. It was the sweetest approach I could have hoped for.

And then one day, in real life, and much to my own surprise, I actually did start to flirt with him. A little. Tentatively. Playfully. And he was willing to come along for that ride.

When I told him that starting hormones might mean growing boobs, he asked if he’d ever get to touch them. “Maybe if you buy me a drink!” I answered.

When I mentioned that I had pictures of myself dressed, he was excited to see them, and his eyes grew wide as he told me how cute I looked.

“That was a while ago,” I admitted. “I’m not exactly that sweet young thing anymore…” He smiled.

When I told him that I was afraid I’d be an ugly woman, he said, “So what? Just be who you are.”

When he asked if I thought I would ever become attracted to men, I said that I didn’t know, but I could imagine it. He seemed intrigued.

When I told him that my wardrobe of female clothing was pretty tame — much like that of any other woman — he replied by saying, “You should show me sometime.”

Then he asked if I had any stilettos, and I said that of course I did.

He asked if I was blonde or brunette, and I said that he could choose!

Suddenly, my hopes of him actually being into this grew until they were almost overwhelming. So I packed a bag full of girl clothes that I could take with whenever I knew I’d see him alone. The first time I brought it with, I left it in the trunk of my car, but I told him it was there. He said, “Bring it out! Let’s see you!”

Unfortunately, the timing wasn’t right that night. His roommate was due back, and neither of us wanted to have to explain ourselves. But I had begun flirting with him, and he flirted back. Heaven!

But from that moment, I — well, actually, we, I think — began looking for opportunities for me to dress up for him, and show him what I looked like as a girl in real life. I couldn’t really tell at first whether he actually wanted to see me that way, or was just humoring me because he could tell that I wanted it. He played his cards pretty close to the vest. But I started to imagine that he was fantasizing about that happening just as much as I was.

And that is when I became obsessed with finding some way to experience at least a little of this in real life. Knowing that fantasy and reality often diverge in significant ways, I never assumed that this was something he would ever want or even consider. But I began to concoct a plan to get him into a bridal photo session, with me as his bride, just to see what might happen.

To get to that point, however, I knew that I would have to lay some more groundwork with him, so that’s what I put my mind to, and that’s exactly what happened.

To be continued…