Community Conversation => Transsexual talk => Post operative life => Topic started by: echo7 on March 07, 2018, 07:29:20 PM Return to Full Version

Title: When to tell your man that you're trans?
Post by: echo7 on March 07, 2018, 07:29:20 PM
Please, I'm only interested in hearing responses from transsexual women who are currently in, or have had, a successful long-term romantic relationship with a man.

My question is, When did you tell your date/boyfriend/husband that you're trans?  Did you tell him before the first date?  After the first date?  After several dates?  Before sex? Just before it became a serious relationship? After engagement?  Or even after marriage? And do you think your timing was okay, or do you wish you had told him later, or earlier?

I'm currently struggling with this question myself...
Title: Re: When to tell your man that you're trans?
Post by: Mallory on March 08, 2018, 10:13:28 AM
I tell them all, both men and women, that I'm trans before the first date.
Title: Re: When to tell your man that you're trans?
Post by: Julia1996 on March 08, 2018, 12:37:41 PM
I've been in a relationship for almost 2 years now. I told him after we had been dating for a month.
Title: Re: When to tell your man that you're trans?
Post by: Sophia Sage on March 09, 2018, 02:11:28 PM
I've never disclosed, even in a 6-year relationship with a man.
Title: Re: When to tell your man that you're trans?
Post by: Devlyn on March 09, 2018, 02:24:11 PM
Quote from: Sophia Sage on March 09, 2018, 02:11:28 PM
I've never disclosed, even in a 6-year relationship with a man.

If someone did that to me and i found out, I would  run, not walk out of the relationship.

Not because I'm anti-transgender.

Not because I feel the person shouldn't make their own decisions.

I'd run because the person felt entitled to make my decisions for me.

Hugs, Devlyn
Title: Re: When to tell your man that you're trans?
Post by: herekitten on March 09, 2018, 03:30:21 PM
It was different timing for the few I have told. Some I never even went there because I had no interest in them beyond friendship. But then there are those whom I bonded with mentally/physically and I know it was going further -- then the dreaded subject had to be dredged up. So never for some, and maybe after a month or two or three for the few whom I felt were worth sharing my life.
Title: Re: When to tell your man that you're trans?
Post by: echo7 on March 09, 2018, 06:40:10 PM
How did you ladies tell your guy?  In person? Or over phone/text? And did you give a long explanation or did you keep it short?
Title: Re: When to tell your man that you're trans?
Post by: Julia1996 on March 09, 2018, 08:36:41 PM
Quote from: echo7 on March 09, 2018, 06:40:10 PM
How did you ladies tell your guy?  In person? Or over phone/text? And did you give a long explanation or did you keep it short?

I told Tristan in person. I gave a medium length explanation.  I toyed with the idea of yelling him in a text because I had had a bad experience telling a guy in the past and I wasnt sure how he was going to react. But I thought it was something that I needed to tell him in person.
Title: Re: When to tell your man that you're trans?
Post by: Sophia Sage on March 12, 2018, 09:53:23 AM
Quote from: Devlyn Marie on March 09, 2018, 02:24:11 PM
If someone did that to me and i found out, I would  run, not walk out of the relationship.

If any of my lovers had brought up the issue, I would be the one leaving the relationship.  I would only have an open narrative with another transitioner, and even then only with someone who practices non-disclosure as a rule. 

QuoteI'd run because the person felt entitled to make my decisions for me.

I do not believe that anyone else gets the right to choose how to gender me.  I will be gendered solely on my embodiment, presentation, and behavior... not through some kind of ritualized narrative request. 

Title: Re: When to tell your man that you're trans?
Post by: echo7 on March 12, 2018, 08:49:38 PM
I was really hoping to avoid instances of thread-crapping here, which is why I asked in the first sentence of my original post for some courtesy.  Please respect my desire to have a productive and helpful conversation here, and please try to avoid redirecting the discussion toward a different topic.  Thank you.  :)

Thank you for the responses thus far, and also to those who have sent private messages to me about their experiences.

My dilemma is this - I'm hoping to find a long-term relationship; really a future husband.  But I'm not exactly young anymore, and so time is not on my side.  I don't want to spend months or even years dating a man, only to have him leave the moment I tell him I'm trans.  So maybe it'd be better if I told him early.  Or even very early.

On the other hand, if I tell him too early, maybe he won't want to get to know me in the first place.  While trans women are becoming more accepted in society, I feel like there's still a huge stigma against straight cis men who date/marry trans women.  So maybe if I tell him after we've gotten to know each other and maybe even after we've fallen in love, he'd be ok with my being trans.  But if I told him too early, he wouldn't even want to get to know me better.

I don't know what to do.  Anyone else willing to share what worked for them?
Title: Re: When to tell your man that you're trans?
Post by: Julia1996 on March 12, 2018, 09:57:47 PM
Tristan and I had been dating for a month when I told him. He wasn't immediately accepting. It was a big shock for him and he said he needed to think about it. I figured that was the last I would hear from him but a week later he wanted to talk. He had done some research online about trans people. He said he really liked me and he wanted us to keep dating and since I was having surgery soon he was willing to wait. I honestly don't think he would have been as willing to accept me being trans if he hadn't had that month to get to know me. In my opinion it's better to let a guy get to know you a little before you drop the trans bomb on him.

I asked Tristan to give me an honest answer and I asked him if he would still have wanted to go out with me if I had told him I was trans when he first asked me out and he said honestly, no he wouldn't. He had never met a trans girl before, knew nothing about us and had misconceptions about trans women just like lots of guys do. Again I believe it was the month he had to get to know me that helped him be more accepting. I am not saying to "fool" some guy sexually,  I'm just saying I believe it's helpful to let him get to know you a little as a person before telling him.
Title: Re: When to tell your man that you're trans?
Post by: Miss Clara on March 12, 2018, 11:02:17 PM
I have no personal experience, so my comments may not be worth much, but I'll give you my thoughts.  I think you are right about the risks of revealing your status too early vs waiting too long.  So how do you decide the right time to tell all?  It's very hard to know, but there are some guiding principles.

You want a person to love you for the qualities you possess that will lead to a lasting relationship.  It takes time to get to know a stranger beyond the superficial.  You both need that time.  If his interest in you is very shallow, learning that you are trans will probably end the relationship right away.  Budding relationships frequently end prematurely on discovering some potentially messy complication.  What's to lose?  Since you pass convincingly as a woman, I would hold off tell your date in the early going.

Eventually you reach a point where you have to tell him.  When you do, you should not lose heart based on his initial reaction to learning that you are trans.  It's not unusual for a man to take a step back or run for the hills.  It's not necessarily a bad thing.  It tells you that up to that point he saw you as an attractive woman, which you are, and that his interest in you was for reasons other than your being transsexual.  That's a good thing. 

I would take full advantage of the initial weeks of a new relationship to establish a bond with this person whom you might some day marry based on things that really matter.  I would hold off on having sex on the first or second or even the third date.  Longer if you can manage it.  If a guy really likes you he'll be patient, and it will give you time to feel out the depth of his feelings for you.  When there's no putting it off any longer and you feel he's entitled to know the details of your past, you want him to be aware of what he's giving up should he decide to walk.  A good man who loves you will be reluctant to throw away someone who he values regardless of gender issues.  If he walks away for good, you know that he was never the right person for you from the start.  If, however, he's willing to stick it out and work through any misgivings for the sake of preserving your developing relationship, then you know you have found a man worth your time.
Title: Re: When to tell your man that you're trans?
Post by: Sophia Sage on March 13, 2018, 11:01:28 AM
Quote from: echo7 on March 12, 2018, 08:49:38 PMI don't want to spend months or even years dating a man, only to have him leave the moment I tell him I'm trans.  So maybe it'd be better if I told him early.  Or even very early.

On the other hand, if I tell him too early, maybe he won't want to get to know me in the first place.  While trans women are becoming more accepted in society, I feel like there's still a huge stigma against straight cis men who date/marry trans women.  So maybe if I tell him after we've gotten to know each other and maybe even after we've fallen in love, he'd be ok with my being trans.  But if I told him too early, he wouldn't even want to get to know me better.

Let's assume you're going to disclose and take non-disclosure off the table.

Do you plan on practicing non-disclosure in the rest of your life, or are you going to be living with an open narrative of being trans?  If the latter, you should tell up front, before dating, because anyone that's interested in getting to know you is going to find out sooner or later, and it's best to weed out the people who won't understand you as soon as possible.  Also, this is the ethical position for someone who is out -- because being out has social consequences not just for the person who is out, but for their partners, too.

If on the other hand you practice non-disclosure as a general rule, wait until the relationship is serious.  It may take weeks or months, not years, to determine this.  In the meantime you get to find out if you're compatible -- in conversation, in values, in sex, and in the practical material reality in which you live your lives.  When you come out, it will be an act of intimacy, an intimacy earned through the building of a relationship. (Don't wait until the marriage proposal, which has its own rules of engagement.)  And hopefully you won't end up making yourself out to your entire social circle because you've determined, through the time you've invested in this relationship, that if he does bail on you he's not also going to try and ruin you.

Never forget that coming out as trans (which is true for all instances of coming out) is tacitly a request to be treated differently.  At what point in this potential romantic relationship is the best time to do that?  Maybe it's at whatever point you decide you want to be treated differently, which may not be something you can really plan in advance. 
Title: Re: When to tell your man that you're trans?
Post by: Barb99 on March 13, 2018, 12:20:57 PM
I've been dating post op for about 16 months now. In that time I've had one relationship that I thought might go somewhere so I told him on our 3rd date. He said he was ok with it but we have not dated since. We still talk once in a while but a serious relationship is just not going to happen.

I believe that had I waited until we got to know each other better we would still be dating. Since that time I have decided not to tell until the relationship gets serious, exactly when that is I don't know. I guess I will have to judge that at the time.
Title: Re: When to tell your man that you're trans?
Post by: Barb99 on March 13, 2018, 12:24:12 PM
Quote from: Sophia Sage on March 13, 2018, 11:01:28 AM

If on the other hand you practice non-disclosure as a general rule, wait until the relationship is serious.  It may take weeks or months, not years, to determine this.  In the meantime you get to find out if you're compatible -- in conversation, in values, in sex, and in the practical material reality in which you live your lives.  When you come out, it will be an act of intimacy, an intimacy earned through the building of a relationship. (Don't wait until the marriage proposal, which has its own rules of engagement.)  And hopefully you won't end up making yourself out to your entire social circle because you've determined, through the time you've invested in this relationship, that if he does bail on you he's not also going to try and ruin you.


This is exactly how I feel and how I live.
Title: Re: When to tell your man that you're trans?
Post by: Northern Star Girl on March 13, 2018, 12:32:51 PM
I have been full-time for almost a year and a half.... I feel that I look, dress, and act undeniably female and pass 100% so guys (and gals) do not have a clue. 
I feel that once I am on a date that goes beyond hand-holding, hugging, and casual kissing that is definitely the time to reveal my secret past.   Otherwise it is not being fair (or even not being kind and considerate) to my date.
Danielle
Title: Re: When to tell your man that you're trans?
Post by: herekitten on March 13, 2018, 03:11:55 PM
Echo, I've never felt there was a methodology for talking about what is between your legs.  It is so different for each of us and the unique situations we find ourselves in or for whatever other reason life throws our way. I can only speak from my experience because everyone has a different opinion -- all worthy of listening to. I've had three marriages in my life and I'll share with you:
Marriage 1 - I was barely 18. He was in the Marine Corps. We dated about two months before I 'told' him about those parts of me. Never used the word trans, man, boy, male, masculine (its just not me). Just that the stars did not align in my favor upon my birth. He was charming. He was so in love. As much as I was. He was also very horny  >:-)
Marriage 2 - This marriage found me a bit wiser and a bit more financially independent. I was a very picky choosy girl. We dated about three to five months but I knew all along he was the 'one'. One night, I just decided this was it. Ugh! I did not want this perfect man to view me any differently. Again, never used the words man boy trans.  I took a breath and 'told' him. He did not understand. Finally the light went off. We were married for 18 years.
Marriage 3 - What can I say, the third time is the charm. Truly. I am without words to describe my Love. I told him before we even met. The days of the internet were just dawning and AOL was at its highpoint. I met him accidently on line attempting to join a 'chat room' that was full.  Upon our meeting in person, there were no walls, no curtains, no mysteries or anything to hide. I could just Be.  Every man pales in comparison when I think of him -- ooh, I'm thinking of him now  :laugh:

My only piece of advice is that if you want to make an omelet -- you gotta break some eggs!! Go get that man!

PS:  Still preop - but not for long YAY.
Title: Re: When to tell your man that you're trans?
Post by: Megan. on March 13, 2018, 03:34:21 PM
Although I didn't really know what I was at the time, keeping my feelings away from the person who became my wife (now Ex) cost me my marriage and a life with my children.
I would always advise honesty as early in any relationship as possible, to save them and you from any pain down the road. X

Sent from my MI 5s using Tapatalk

Title: Re: When to tell your man that you're trans?
Post by: alex82 on March 17, 2018, 11:06:31 PM
One night stands, never.

As a plan, when and if it feels appropriate for that person to know.

For the man I'm seeing now, before either of us were interested in each other, and while he was still living with his girlfriend. We happened to end up in deep discussion on a night out and that was one of many things we talked about.

There was a natural entry into the discussion because we were talking about our children, and mine is relatively newborn. It was an arrangement with a friend and we divide up the week equally, he was talking about his own young children and custody arrangements because his relationship was breaking down.
Title: Re: When to tell your man that you're trans?
Post by: softbutchharley on March 19, 2018, 04:40:18 PM
Quote from: echo7 on March 07, 2018, 07:29:20 PM
Please, I'm only interested in hearing responses from transsexual women who are currently in, or have had, a successful long-term romantic relationship with a man.

My question is, When did you tell your date/boyfriend/husband that you're trans?  Did you tell him before the first date?  After the first date?  After several dates?  Before sex? Just before it became a serious relationship? After engagement?  Or even after marriage? And do you think your timing was okay, or do you wish you had told him later, or earlier?

I'm currently struggling with this question myself...
Hi there echo :)
1) I had sport sex a few times pre op and disclosed first date . I would NEVER even start to go in a sexual direction pre op . No way... People do not deserve that IMO .
2) I dated several for short periods POST op - never disclosed, tho one was very "tuned in" and a friend of the community, and the other 2 I had known previous to my starting transition. From start to finish, my transition was about 18 months, mainly due to surgery healings. A long time pre,  and since, I have attempted to work on me inside.
3) I have had several long term lesbian relationships ( year or better) and am in my third one now at 7 years. Never disclosed.....the gals knew from meeting me pretty much, but no disclosure or discussion about "it" .  :)
I guess this is not too helpful with the specific requirements of your post, but I believe my experience touches a few.
TY for sharing here, and I hope my experience (all I have to share) helps.
J
Title: Re: When to tell your man that you're trans?
Post by: ForeverLacey on March 23, 2018, 10:50:56 AM
I let everyone know at the time interest was developed. I believe it is fair for guys to know and honestly, I don't want to be a name on Transgender Day of Remembrance.
Title: Re: When to tell your man that you're trans?
Post by: Alanna1990 on March 23, 2018, 11:01:57 AM
Quote from: echo7 on March 07, 2018, 07:29:20 PM
Please, I'm only interested in hearing responses from transsexual women who are currently in, or have had, a successful long-term romantic relationship with a man.

My question is, When did you tell your date/boyfriend/husband that you're trans?  Did you tell him before the first date?  After the first date?  After several dates?  Before sex? Just before it became a serious relationship? After engagement?  Or even after marriage? And do you think your timing was okay, or do you wish you had told him later, or earlier?

I'm currently struggling with this question myself...

I'm married so I think I can be of help here, always be clear about it, some men can be real charming until they know about it, telling everybody gets rid of the people that are not worth it, before you date him is the best time,

something like this: "yeah, I'd love to go out with you, but I have to tell you something important, I'm transgender",

most will tell you, "uhhh, sorry I didn't know, I'm not interested, sorry", discard them obviously.

others will tell you, "really?? you look amazing!, we should date anyways", I'd date them but never expect something important happening there, they may just be curious about dating somebody like us.

and finally, "ok, so... saturday night?", like my dear husband :icon_love:
he's never shown any concern or anything regarding the topic, he treats me like a princess and lets me be myself, no uncomfortable questions about anything, he's just a man dating a woman.

my point is, choose to date somebody who doesn't give two dimes about your private parts, they're hard to come by, exactly like us, so it's worth the effort.
Title: Re: When to tell your man that you're trans?
Post by: Devlyn on March 23, 2018, 11:40:29 AM
Quote from: Alanna1990 on March 23, 2018, 11:01:57 AM
I'm married so I think I can be of help here, always be clear about it, some men can be real charming until they know about it, telling everybody gets rid of the people that are not worth it, before you date him is the best time,

something like this: "yeah, I'd love to go out with you, but I have to tell you something important, I'm transgender",

most will tell you, "uhhh, sorry I didn't know, I'm not interested, sorry", discard them obviously.

others will tell you, "really?? you look amazing!, we should date anyways", I'd date them but never expect something important happening there, they may just be curious about dating somebody like us.

and finally, "ok, so... saturday night?", like my dear husband :icon_love:
he's never shown any concern or anything regarding the topic, he treats me like a princess and lets me be myself, no uncomfortable questions about anything, he's just a man dating a woman.

my point is, choose to date somebody who doesn't give two dimes about your private parts, they're hard to come by, exactly like us, so it's worth the effort.

Amen! We're too special to waste our time on a partner who wouldn't appreciate the treasure that is us.  :)

Hugs, Devlyn
Title: Re: When to tell your man that you're trans?
Post by: Allison S on March 23, 2018, 02:31:39 PM
I wouldn't waste my time telling a stranger. That actuslly could be dangerous... I would first see if we even click on a personal level. If we did, and I feel like I'm comfortable, I would tell the guy. I may never see him again, but if that's the case than we weren't meant to be.

Trans or not, everyone's a treasure. If some guy, or any person, can't overlook something like that than they're not worth the time or effort in the long run anyway.

Sent from my SM-G930T using Tapatalk

Title: Re: When to tell your man that you're trans?
Post by: Rumples on March 24, 2018, 03:34:53 PM
I keep myself to myself.  During the first year of my first real relationship, my family decided it was their business to casually inform my then partner. It was then held over my head as our relationship span of of control and exploded in slow motion. After we split, because I didn't come back when they clicked my fingers they just tossed it out there. Luckily, I had left town by this point.

My current partner of over 10 years found out by mistake when she was doing some cleaning a few months into our relationship.  No problems, she said she would never have guessed and just asked a few general questions.

Personal choice, I wouldn't go out of my way to, as to me, it's non of their concern. 
Title: Re: When to tell your man that you're trans?
Post by: Ellement_of_Freedom on March 31, 2018, 04:52:54 PM
Quote from: echo7 on March 12, 2018, 08:49:38 PM
On the other hand, if I tell him too early, maybe he won't want to get to know me in the first place.  While trans women are becoming more accepted in society, I feel like there's still a huge stigma against straight cis men who date/marry trans women.  So maybe if I tell him after we've gotten to know each other and maybe even after we've fallen in love, he'd be ok with my being trans.  But if I told him too early, he wouldn't even want to get to know me better.

Quote from: Julia1996 on March 12, 2018, 09:57:47 PM
I asked Tristan to give me an honest answer and I asked him if he would still have wanted to go out with me if I had told him I was trans when he first asked me out and he said honestly, no he wouldn't. He had never met a trans girl before, knew nothing about us and had misconceptions about trans women just like lots of guys do. Again I believe it was the month he had to get to know me that helped him be more accepting. I am not saying to "fool" some guy sexually,  I'm just saying I believe it's helpful to let him get to know you a little as a person before telling him.

My sentiments exactly. Until the stigma doesn't exist anymore, I think it's necessary for them to get to know us without the trans label hanging over our heads. Once we have shown them that we're just like any other girl, then I think it's an appropriate time to tell.

I actually lose a lot of sleep over this topic on a regular basis...
Title: Re: When to tell your man that you're trans?
Post by: Spunky Brewster on April 09, 2018, 05:18:20 PM
I'm in a nearly five-year long relationship with a man come June 5. I'm 35 now. I started transitioning three months before I met him in one of the worst areas of Philadelphia you can imagine. Here is a link to where we met!: https://philly.curbed.com/2017/12/19/16792862/kensington-philadelphia-bridge-mural-photos

At that point in my transition, I barely passed; it had only been three months, and I had a very short pixie cut. I also dressed very andro. But, he said he saw me from afar and couldn't figure out if I was a boy or a girl, but that I looked really pleasant. In any event, we really hit off. And I'm really shy, especially around men. But he was funny and nice. So, we went back to his house and sat on his steps in West Philly til the wee hours of the morning. I ended up sleeping on his couch. At some point that night, I told him I was trans. (I'm actually intersex, but the difference means nothing to me, so I just say trans until I really know someone, as it is really confusing). He said he though so but didn't want to be rude.

I never thought I'd hear from him again but he texted several days later. Then, out of nowhere, I got a settlement check from TD Bank for overdrafts. You need money in a new friendship. I was poor. Dirt poor. Then, we started hanging out all the time. We moved in together by September and slept in the same bed. We weren't dating and he said he would never date me. Which, I accepted.

I don't know what happened but about nine months after we met, we had sex. Then, we didn't do it for awhile. Finally, we really started hooking up and I would say our relationship officially started around September 2014--15 months after we met.

My advice: tell the person upfront, especially if you don't "pass" well. If you do, only put it off for so long. Secrets kill relationships. And this secret may kill you. Maybe you could put it off longer, but I would always disclose before any "hooking up" beyond hand holding/hugging. If you kiss, tell him. Do you want to live with a secret forever. That seems exhausting.

BTW, my BF is from the Applachian Mountains in NE PA. He is fairly religious and conservative, though more apolitical. But, it works for us and he is totally in love with me. My life has been a nightmare. Did you look at the link? That's where I'm from. It's the heroin capital of America. Yet, five years after transitioning, every dream I ever had has come true: surgery, I'm super pretty, I have a loving amazing BF, and everything is going my way. If it can happen to me, it can happen to you.

However, if you really want a husband, you need to tell the truth. Unless, that is, you are willing to lie to someone about who you are day in, day out, hoping he never finds out. It's not 1980. What happens if he runs a search? remember, many guys, especially ones over 30, are much more open-minded these days. But guys are extremely insecure. All of them. Even if you don't pass to well, practice your voice until you get it right. This is prolly the most important thing of all. No straight man wants to hear his woman sounding like Barry Baritone. If you can get voice surgery and need it, do it. If not, go to a voice therapist.

I'm lucky, but I can sound like a man sometimes when I get mad. It's the only tell I have. Yet, if I don't get upset, I'm fine. Just practice. Always use your feminine voice. Not a falsetto. even if it is a bit deep, that isn't the end. If you can get it up to 160 hrz., you're gold. Mine registers at 180-220, but like I said I'm lucky. It also can go as low as 90, so yeah. I can't stress this enough.
Title: Re: When to tell your man that you're trans?
Post by: SaphRose on April 09, 2018, 05:37:49 PM
Hello, I'm a stealth girl, who's been in a relationship with a man for the past year.

My boyfriend and I met on a dating app, where I clearly stated I was trans on my profile to avoid wasting time.  He knew before he even messaged me what the situation was.  It came up only once, he acknowledged that he understood who I was, and that was that.  However, he did tell me when he first saw me on there he had no idea I was trans but that when he found it, it really didn't sway his opinion one way or the other.

We were best friends for 7 months before dating, and during our whole friendship we were flirty and made it obvious we liked each other in that way, we started dating when we were both ready about a year ago, and now we're still together and we live together with two fur babies. :3

I told him off the bat, while it was passive and not directly stated to him, I think the way it worked out was perfect.  I never really had to have "that" conversation with him, which I'm not sure how I would've handled that. I think waiting to tell him would've made things more complicated, but honestly my boyfriend is the very openminded and compassionate type so that sort of thing would've never bothered him in the first place.

There is no really right time to tell someone, but I'm going to just let you know this:  The longer you wait and the more you get to know someone, the harder it'll be to tell them.  It's always best in my opinion, to be straightforward with that kind of thing as to not hurt anyone — but most importantly to not put you in a harmful situation emotionally or physically.  Every man is different, and it really depends on the dynamic of your relationship and who he is as a person which can dictate your timing.
Title: Re: When to tell your man that you're trans?
Post by: Spunky Brewster on April 09, 2018, 08:01:27 PM
Quote from: SaphRose on April 09, 2018, 05:37:49 PM
We were best friends for 7 months before dating, and during our whole friendship we were flirty and made it obvious we liked each other in that way, we started dating when we were both ready about a year ago, and now we're still together and we live together with two fur babies. :3

I told him off the bat, while it was passive and not directly stated to him, I think the way it worked out was perfect.  I never really had to have "that" conversation with him, which I'm not sure how I would've handled that. I think waiting to tell him would've made things more complicated, but honestly my boyfriend is the very openminded and compassionate type so that sort of thing would've never bothered him in the first place.

We have very similar situations with men. Though I met mine on the street, well, actually a small bridge, he knew very fast as I had only been on HRT for a few months and we were best friends before we started "dating." I just put our anniversary as the day we met, but it's hard to pin down an actual date.

Moreover, I don't know what I would do if i had to have the conversation. I feel incredibly lucky. I think your route is the best way to go for most people: dating sites. You put it up there and see what happens. I do think it is a lot easier for trans women who pass extremely well and don't just "pass." I hate to be all I'm so pretty, cause I think I'm pretty ugly, but the world tells me otherwise.

However, if my BF dumped me, God forbid, and I had one night stands. I would not disclose. I have no reason to do so. My surgeon is amazed at how my vagina looks, as is my BF. My BF was there when they removed the catheter and bandage and he saw my seven-day-old franken-pussy. OMG. I was aghast for a month. My boobs were gigantic. My vag looked like someone sliced me open. I felt like I was butchered. But, six months later, it is amazing. There would be no way you would ever be able to know without an actual gynecological exam with a speculum. They don't bother me that much, though they look medieval.

No guy would be able to tell the difference. No way. No how. But, I do have to use lube, so there is that.