Learning to assert my own boundaries and feeling my way back into a world of love


I’ve been “dating” a transgender woman.  She is beautiful and fragile in a way that I have found resonates throughout the trans community.  A not-quite-believing-I-am-here feeling.  She is a tremendously talented young woman, and one whose future is hers to claim.

I find tremendous solace in that she finds comfort in me.  There is nothing more fulfilling to me than being the source of someone else’s comfort.  I sometimes refer to it as my kink, and absolutely, in writing about service, this is never too far from the surface.  Ditto for friendship…so much of the value in friendship is being there for someone—and knowing that they will be there for you.

In other words, I like her.

But dating her has challenged me in many ways which are uncomfortable for me.  And this is particularly difficult to admit as a transgender person myself.  She is beautiful.  This is not boastful, it is a statement of fact, and her professional success in a glamorous world is an objective testament by any measure. I will not say more as it becomes too revealing–publicly identifiable.  

She transitioned as a teen, and perhaps only another trans person would ever clock she was AMAB.  She is possibly the best kisser I have ever encountered.  Her lips talk, move as if they have a life of their own, a mind of their own, a separate consciousness.  They are soft and gentle and exploring.  My first kiss with her erased all of the anxiety I felt as someone going through a divorce from a life partner—the ‘will I ever find someone again?’ feeling.

But I have to face my own prejudice.  Part of me holds back because of where I am in the dissolution of my marriage—not being ready—mainly to integrate someone publicly into my life.  But when she expressed a desire to meet my children, I felt ‘no’ and realised that this feeling is born of prejudice and shame.  Shame on me.

Under those circumstances, is it wrong of me to even dare to ask to ‘just be friends’?

In the meantime, I am dating.  And I find myself so utterly and deeply drawn to the potential that is there in every single date.  Is that a dangerous way to think?  In the sense that we envisage, manifest, fantasise about how our relations with a person might evolve?  One woman is a cougar, and for whom I have had the hots since I first met her through cooking.  We cooked together in a social setting, and boy was there electricity.  It happened again, and the electricity was real, and I let it lie because I was a married boy, a good boy, and good boys don’t stray.  But now I am free, and so is she.

She does not know that I am trans.  And I kind of just want to tell her.  My male friends tell me, ‘yes, tell her’.  Or, ‘you should show up to your date as you now are.  No better way to let her know’.  My female friends say, ‘let her in on it slowly.  Maybe paint your nails, but that’s it.  And if she asks, then tell her.  But if she doesn’t, just read the energy.  You’ll know if she is curious.  You have so much more to offer than being trans, don’t make that the heart of it’.  There is so much in the sex differences of the two types of advice.  Amiright?!

Another person is more of a potential friend, but she knows all about my journey—both as a submissive lover of sex workers, but also as a transgender person.  I shouldn’t really consider our rendezvous as a date, and I don’t, because I just like her as a fellow human…and there are so few magical humans who see me and know me all the way…and so they are very cherished people (even the ones who don’t like me anymore).  But I can’t help but see her as a date because of how impossibly glamourous she is.  There are some people that you just die to be arm candy for, and she is one of them.

And then there is a woman who I met professionally—not in the way often referred to on this web site…vanilla professionally is what I mean.  But she knows about me and submission and is a proponent of FLR.  Since my body is in a permanent state of chastity now, this could be quite interesting.  The potential for play is great.  Only I don’t fancy cuckolding because of the humiliation aspects…but knowing what lies ahead for me anatomically, and knowing that upcycling my whotsit into a vagina means that I will no longer ever have to play a male role in bed anymore, would I ever begrudge a woman I dated a romp in the hay with a virile, hot-blooded man?  Probably not.  Only, I would likely worry about her developing a case of the feels for such a person…and boy, respect for sex workers who do this and love getting off, and never develop the feels.   I have no idea how that is possible.

Back to my transgender friend.  We went on a date to one of London’s finest dining establishments, a total place to see and be seen.  The place.  As a 6’4” skinny trans-femme-to-be wearing a slinky dress, I was deeply touched to be placed at the most prominent and visible table in the house, the first one you see walking in the door. It was a colossal honour particularly since we didn’t have a booking, and hats off to the restaurant for taking such good care of me and for being so supportive in such a small, yet significant way. Bless them.

But my date was late.  And since I am painfully punctual as a consequence of marriage to someone who is painfully punctual, late doesn’t sit well with me.  And for anyone else, except for perhaps a Domme, I would have gotten up and left after 30 minutes.  But I waited for 90.  And then she came and we had a fabulous evening, but it affected me.  

It is a feeling of being disrespected.  And whoa, I am dangerous ground here because this feeling of being disrespected is one of the signs of narcissism.  But for me it is also a boundary.  It is the exact same boundary that backed me into a corner with ex-Mistress—of feeling discounted, disregarded.  I’m not sure she understood that even when I expressed it, but it was exactly the feeling that made me push back and challenge her boundaries, as it was the only way out for me.  I share this trait with narcissists—I don’t want to be disrespected.  Is that wrong?  It doesn’t feel wrong.  It feels healthy.

When my date arrived, I saw that she stayed outside and smoked a cigarette before coming in.  And that action spoke louder than her anodyne apology. I do know that people in the fashion world are “fabulous”, but is there ever an excuse for this? I can’t think so.  But I do like her.  Mostly I want to help her.  I have this weird feeling of mommy energy coming from me to her…But I realised also as I sat there, that I wouldn’t ask her out again.  At least not in the same way—on a date.  

Instead, I simply said, I will be at such and such a place at such and such a time if you care to join me.  That was for a lunch, for a dinner, for an event, for another event, whatever.  When someone has a casual relationship with time, especially other people’s time, it means that they have no problem with you sitting around wasting your time waiting while they do whatever is more important to them. Not good.  So this became a casual way of me asserting a boundary.  ‘I am not going to wait for you anywhere.  I’d like to see you, but only if you sync up with other plans’.  Is this wrong?  I do this because sitting alone waiting for someone is a slap…and as someone who is relentlessly energetic and needing to accomplish things, there is nothing worse than dead time.  And that is exactly what waiting is.

And what that means is that we don’t see each other.  Recently she didn’t show up to an event that I had invited her to…which was okay, because I met a ton of people there, and it was exactly why I had wanted to go…but the no-show was part of the pattern.  Later, she showed up unannounced at my hotel and called me from the lobby.  I hadn’t expected to hear from her, and clearly she wanted to come up. I declined to invite her up.  I don’t want to make space for people who are unreliable.   Is that wrong?

When I think of the greatest lesson learned from my experiences with sex workers, it is the concept of boundaries: knowing them and asserting them.  I’ve learned more in this way and in this aspect from them than I have from my therapists.  Therapists, on the other hand have given me two tools in relation to boundaries: acknowledging that I have always struggled to assert my boundaries starting with my parents and siblings growing up, bleeding into every relationship I have had, and secondly, feeling strong enough to assert my autonomy in this regard.

I can be miffed with ex-Mistress for letting boundary issues arise given her experience; I can be relieved that we are not entangled any longer and know I won’t ever see her again; and I can still love her and be grateful to her.  The things that we do, the experiences we have, all have the potential to enrich our lives—both the good ones and the bad ones…it is a question of perspective.  In my obsession with learning how to conduct myself with more grace and kindness, I am confronted with the reality of both how hard it is to let go of earthly wants and desires, but also just how delicious everything becomes when we let ourselves just be present, in the moment, floating.

5 thoughts

  1. what can i say? there is honestly a part of me that wishes i had your problems. “i get along with professionals” aka you have money, the trans girl you’re dating probably developed feelings for you and you’re dating 3 different people,
    hmm-ing and hah-ing over whether her showing up late means you’re being taken advantage of. i feel like your position of privilege gives you too many options, and too many societal blindspots, to really care about these people as individuals. maybe that just comes with the territory, or maybe you’re right and i’m just jealous enough of your privilege to poke petty holes in it, i’m not sure.

    Liked by 1 person

    1. That’s wonderful. I have a love/hate relationship with tucking. I don’t want anything to be there, but it hurts. Oh well. That’s wonderful about the orchid…I figured I would do the same, but now that I am thinking I will go straight to a vagina, I don’t think I want an extra intervention. Plus, I love what finasteride is doing to my mane–but people do say that the blockers are really bad for you.

      I have heard that topical finasteride is very effective for hair growth, but nobody in the US seems to offer it…have to figure out where to get it…

      Liked by 2 people

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