Misadventures with dating Apps and do they make me feel better or worse?

I seem to meet a ton of new people by just walking around.  Things as a man were not like this.  I guess as a tall man, with fairly strong features, and a generally quiet demeanor, I might have seemed unapproachable.  I might have been.  I just didn’t feel so inclined to talk to strangers.

That has changed.  Oestrogen has made me more social.  Being vulnerable, physically and emotionally, and boy, is that ever the essence of being “out” as a trans woman, has changed this dynamic fundamentally.  I engage with everyone.  It isn’t a conscious process.  I am only realising it for the first time now.  But I talk to people on the street, I talk to all the shopkeepers, I talk to taxi drivers.  It didn’t used to be that way.

In the small city I live in, there is a practical benefit to this.  I feel less and less stared at.  Less and less some “weird” thing.  Instead, the chatter seems to have subsided.  An Italian friend told me that I am “normalized” now, as if to say I am “their” trans.  A mascot of sorts.  I think I like that.

I also used to exist invisibly.  My wife was the constant presence here in the house, and in the community, and socially.  This is an unexpected blessing for her to be gone.  Even the neighbours have adopted me.  And after all, why not.  I am not a man in a dress.  At least not anymore.  I am one of those rare and special creatures who can’t live in their own bodies, who get reviled in the press, reviled by politicians who stoke bigotry and hate to gather votes, I am of a tribe of people who spark fear, mainly in men or those who seem to be invested in preserving male power.

Women, the more naturally curious of our species, seem unafraid to express their curiosity, and rope me in.  I get adopted everywhere I go.  It is a wonderful feeling.  It is like being a puppy.

I am no longer afraid of not finding someone.  My sense of possibility has kicked into overdrive.  This was all made possible by someone who just came onto me with intent to close.  She told me what she wanted, which was to tear my clothes off, and that triggered the healthy part of my need to please, and I just whimpered my way into her bed over an increasingly explicit meal.

Something has changed profoundly in me from oestrogen.  It has nothing to do with lowering my standards, which some cynics might opine that comes with age, or making oneself less conventionally attractive.  I admit, the majority of women who hit on me now are still thinking I am a man, just kind of David Bowie like.  Only the looming presence of a sex change is daunting for some.  I could see the disappointment in one woman’s face as I told her.  It reminds me of how many women who muse “why are all the hot/good men gay?”

I get the feeling, but don’t agree with the idea.  Good and bad exist everywhere.

As a man, I think I was afraid of the vagina.  I wonder how many men are?  One of the joys of having one of my own is that any vestigial fear of the vagina will be gone.  I can easily see myself taking lessons on how to please the female body.  And my sense of liberation from not having a penis is so utterly compelling to me, it is hard to get my head around it.  Why would I be relieved?  I didn’t have “performance anxiety” issues as a man.  I was “well-endowed” if only slightly above average.  Plus my male bits by standards of aesthetics were not bad.  I like them better in their reduced state.  “Atrophied” as my recent genito-urinary encounter wrote in my report.

No, there was something more fundamental going on.  Emotional.  Using my dick made me feel male.  And that was hard for a trans woman.  And yet, we always did.  I barely ever received…and by that I mean anal.  Never once pegged.  At least not yet.  When I think back of partners who never triggered these feelings, I realise that even though we always fu**ed eventually, PIV was never the point of sex, it was just the wild and rough finish.  Plus, they were so in it with me physically that it was hard to say who was fu**ing who.

I had a beautiful woman staying with me recently.  I find her bone-crushingly hot.  She is a merciless flirt with me too.  And she also knows what turns me on, and how I feel.  She toys with it relentlessly.  I don’t think I have ever met someone who likes to talk about sex as much as her.  And she loves to talk to me about her men.  Her man.  Maybe it’s weird, but maybe that’s what girls do together.  I don’t know because I don’t have references, but it felt like a very deep and open friendship—with everything on the table.  I can’t imagine having such explicit conversations as a man with anyone, but especially not another man.  I have been told that women go places in conversation that men just never do, and I think that was a bit what was going on.

And this is part of this larger pattern.  Female me is less threatening.  Female me is more accessible.  And I think that this has nothing to do with me per se, any actions, or way of behaving.  I feel the same.  It has everything to do with perception.

Not being a predator is the most fundamental part of my humanity.  It defined my life as a male, and it is still very much with me.  It would hurt to the point of feeling soul wrenching when a woman was scared of me—a stranger maybe, walking on the street at night, but also just casually.  Mostly, when they met me, talked to me, they could feel my energy, and know that it was safe to be with me.  But male-female dynamics have always been complex, and I was always attracted, and that is complicating.

The female-female dynamic that I am stepping into doesn’t have that complication.  To women, I am naturally less threatening.  I am the same person, but the simple fact that I don’t have a dick (or at least for the next few weeks one that works) seems to remove all fear.

I go every week for lessons in rope bondage.  The school has a vast network of nubile young women who like to be tied up.  I am learning that they like to be tied by me.  The feedback is that I am confident, and sensual, but mainly, that they all feel totally safe and respected.  As a slave, it might be weird to think I am doing the tying, but creating this sense in a woman is such a privilege.  To give her the space and freedom to express herself and to just feel, and know that there aren’t going to be consequences, chasing behaviour.

I was deeply attracted to one of them last week.  She was big and strong, very tall, muscular.  Gorgeous face, oozing power.  She was with someone and wasn’t enjoying herself.  She made eye contact with me.  I could imagine myself holding her as I tied her, nestling her between my legs as the rope slowly cut off more and more of her freedom of movement.

After the session, we all went out for a drink and she ended up sitting next to me.  She was intense, very dominant seeming.  “Give me your number,” she said, and then as if apologizing for being so forward, “that is, if you want to.”

“Yes, yes, of course,”  I said, and gave it to her.  She texted me immediately.  “This is X,” it read.

Two days later she wrote to me and told me what she wanted.  She had spoken amongst the other bunnies, and they had discussed what it was like to be tied by those of us who come with some regularity.  She has a boyfriend who doesn’t like this sort of thing but comes along reluctantly.  She wants to see if it feels right to be tied by me regularly.  I’d like that.  But she also knows that I’m a bunny too, and that I am submissive.  And I wonder if that makes her and the others feel safer.  I asked one of the bunnies I have tied at a bunny social—yes, we do get together as bunnies and talk about how to be good bunnies.  In case you are wondering, getting tied up is not a passive process.  As an experienced rigger would tell you, the bunny and his/her responses are central to the dynamic.

What goes in a slave’s mind as she ties someone?  To listen.  To be extra conscious of the pleasure given, and of the experience.  I ask if there is anything I shouldn’t do or should be aware of before we start.  I give explicit permission to be corrected, that their comfort and safety is the first priority, and that they should speak up about anything.  I ask if it is okay if my touch has an erotic charge to it.  This is what they want it seems.  Most of all, I have this burning desire to please.  And that, as a domme, is a good thing.  Perhaps we call it “Service Top”.

Knowing that I will obey them even as they are in bondage gives a sense of safety.  At least I think so.  What I know from having been tied is what that feels like, and when it feels really good.  And you can see it on someone’s face when they slip across the threshold from the here and now and into sub-space.  Am I becoming a domme?

This is an existential question, and one of the great challenges which lie ahead of me.  Which path will my life follow.  I realise I am not a chaser.  And that applies to everything.  The old Jack Welch saying, “control your destiny or someone else will” feels more and more like macho posturing.  One of my absolute closest women friends ascribes to this philosophy and commands me to go out and conquer.  And yet, I find when I do not, and simply show up, the universe seems to help.

I know it will be a good day when I find money on the street.  I do almost every day.  Pennies from heaven.

I developed a crush on an AirBnb host and I will write a semi-fictional account of our time together, which resulted in a gradual evolution away from host-guest to Mistress-slave.  Purely vanilla, but ever-so-flirty.  She got me onto a dating App, amazed that I had never used one. “If you want to have sex…” she said.

It was really helpful to have her live edits and help with picture selection.  I went from no likes to being overwhelmed by likes almost overnight.  The most intriguing thing about it is that it follows me.  So as I barrel around the globe, every town I am in seems to have people looking to meet.  Ironically, it was only when I got home that I ended up matching with someone I wanted to see, and who wanted to see me, and so we did.

I’ve never done that before, so suggested we meet someplace neutral like a coffee shop.  We did.  She was prettier in real life than on her pictures.  She said that helped her to deal with the stalkers.  I think we had a nice time and she asked to see me again.

We arranged for her to come to my town and planned tentatively to go hiking, something which she likes.  In the end, we changed our plans and went out to a nice restaurant in town, also went for coffee and went shopping, or rather, window shopping.  It was easy and natural.  We ended up in a café around the corner from my house as she had a craving for a Sicilian pastry and the only place I knew that had them was a Sicilian pastry and coffee place.

After, I asked if she would like to see my house.  It seemed natural enough and so walked to my house.  As we walked she talked about safety and the precautions she takes.  Always a first date in a neutral place.  Take a picture of their car license plate.  Find out what you can about the person and share that with a friend with a time window.  Don’t get into their car without taking a picture of the plate and them and sharing it.  It saddens me that such steps are necessary, but there is no price safety.

“You shouldn’t trust me,” she said, “I could be crazy. I could be a stalker.” And I’m thinking, ‘why are you saying this?’ I’m thinking, ‘no you’re not’, because I can feel it. But I am also wondering, ‘what happened to you?’ and ‘do I want to get involved with fixing this?’ or even ‘can I?’ and ‘will it hurt me?’ and suddenly I didn’t feel so safe.

I told her that I was too trusting, and that it might get me into trouble.  And that I needed to learn to do that.  Luckily, up until this point in life, I had escaped largely unscathed, but I credit that in part to a very strong sixth sense about situations.  I told her I trusted my gut.  She recounted a story of someone she dated through the App 6 times, including having him sleep over and have sex.  One day she wasn’t available, and he freaked out on her, demanded to know where she was, who she was with, and even came to her place.

Sidebar.  For those of you who are not women, this is life.  To be sexual at all is to invite entitled men, freaks, weirdos, even dangerous people.  And sadly, many men who are perfectly “normal” behave in this way.  It is one of the big scourges of modern life…that over half the population lives in fear.  This issue is core to my psyche.  It is deeply bound with who I am and how I came to be, and is very much one of the root reasons for me to change sex.  Not wanting to be a man is just as strong a force in me as wanting to be a woman, and this is one of the main reasons.

When we got to my front door, however, she said, “Oh I won’t be coming in.  I’ll just stand at the door and look in.”

“I wish you’d said that, I wouldn’t have brought us here.”

“It’s okay, I would never do that.”  A million thoughts went into my head, chief among them, ‘I won’t ever see you again’.  Just then, a call came from my dearest friend and healthcare proxy, my first and most important carer during surgery and post-op recovery.  She had a bunch of things on her mind about life, work, family.  I took the call, and I listened.  It was rude to not tell her I was with someone and I would call her back.  But I was feeling it.  And I wanted to convey without conveying, how I felt.

When I got off the phone, she stood briefly in the door and pointed things out as I stood at a safe distance inside the house, asking me about them.  I answered her questions, and then asked when her train was.  She said she should go, but before she did she said she would like to see me again.  I knew I had no interest at that point.  I had lost it.

I will write a separate post about this, but what was upsetting to me were two things: first, that I was not trusted after having spent the time with her, and second, that I was put into a position of being made to feel like a chaser, which is not at all how I ever want to feel, because it is everything I am not.  I simply concluded that there was a legacy of hurt inside of her, damage, that would be dangerous for me to be around.  Hurt people can be mean.  And it made me realise that I don’t have hurt people in my life…for whatever reason, but the people in my life have all healed themselves, have done the work, have grown up, or maybe this is just another face of privilege—the privilege of not being damaged.

Trust is a two-way street.

The other thing I concluded was that dating apps are not good for one’s self-esteem.  So little matching, so much swiping, and then from what my friends say who use the Apps all the time, a disappointing number of people who actually are worth meeting.  I seem to meet people everywhere, do I need more?  Maybe not.

As she left I picked up my phone and saw that I had a notification from X.  What followed was a steamy exchange between us about what she wanted from me, and that she was going to get it, and that she would come over.  We spoke for maybe 15 minutes.  That’s the kind of trust that I thrive on.  Its opposite makes me feel dirty.

How do all of you feel?  Men or women?

I tried another dating app too.  It was billed as slightly kinky.  I should have known to stay away from it.  They used my domme’s image and links to promote it, but when I asked her about it, she had never heard of them.  Major red flag.  I was on it for a few days, and was flooded with lewd and gross images, or downright aggressive sexual approaches.  I get a bit of that on Fet Life too—putting yourself out there as submissive and female, trans or not, invites all manner of predatory behaviour.

There was one person who seemed interesting and I responded.  The very next message she/they sent was a picture of a lot of dildos and other sex toys saying what she/they wanted to do to me.  I wrote back, “but honey, we haven’t even had coffee yet.”

Thus concludes my adventures with dating apps.  Deleted.