Author Topic: Crazy over this woman. How to tell her I'm trans...?  (Read 470 times)

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Offline PraetorianRhapsody

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Crazy over this woman. How to tell her I'm trans...?
« on: December 07, 2017, 06:08:17 pm »
So for starters... I'm here looking for advice, opinions, etc. This situation I'm in has gotten complicated over the last month and it's time I sort this out, I just need to figure out a plan.

To set the stage... I'm 31 years old, almost 3 years on testosterone, 3 months out of a ten year relationship, and scheduled for top surgery in January 2018..

I work at a county jail where I'm the day shift sergeant (supervisor). About two months ago I hired a girl who is actually one of my employee's daughters, we'll call this girl "M". M's mother is also one of the officers I supervise. M's mother and I have a pretty close friendship. We have worked together for several years and she even was someone I've confided in about my recent breakup and my transition. Mom told me that her daughter was moving home from Nevada and was looking for a job. So naturally, I suggested she come apply at the jail and we'd see if she was a fit. Turns out "M" was an incredibly good fit and I hired her.

The day I met "M" I could tell she found me attractive and even following our initial meeting her mother went out of her way to tell me that "M doesn't care for the night shift Sergeant... but she REALLY likes you."

Now, don't get me wrong.. I found this girl extremely attractive. But I wasn't looking to get into a relationship or even pursue a female because of my relationship BS I was going through. I could tell from the day I met her she found me attractive and over the course of a few weeks she was adding me on Facebook/Instagram (I did not hide my transition videos/photos, everything was out there), messaging me compliments, having lengthy conversations with me, etc.

Setting the stage further... EVERYONE at the jail has seen me transition and knows I'm FTM, including the inmates. I've been working at the jail for five years now.

Moving forward a few weeks, I was having very rough patch with my relationship and M's mother and I decided to go out and have a few drinks together. "M" was invited along to DD. Well, a few drinks later and "M" and I are alone at a table in the bar, having a beer, sitting dangerously close, and we openly admit to one another that we found each other attractive.

Things just escalated from there. We went for drinks a few times, I hung out at her house... then one night she kissed me. BAM! Fireworks. Then every time we'd hang out... more kissing.

Now.. I assumed that she knew about my medical history. And I'm not entirely sure she doesn't know. There are days when I think she does and days when I'm not sure.

One night she invited me out for drinks and we're sitting together.. I has an opportunity to ask her "So, what did your mother tell you about me before you met me?" Her reply was "Does it matter?"

Well, I took that a subtle hint that she knew. Things... hot and heavy happened later that night in a drunken blur.

M and I have really connected over the past month. I sleep over on occasion, she's met some of my family, etc. But the big "Transgender" acknowledgement has not officially happened.

I am feel like I'm starting to catch real feelings for her... She's one of the most incredible people I've ever met. But now I'm terrified of hurting her, should she for some reason not know...

I keep trying to find the courage and the right moment to approach her about it but it never seems to come. I know that if she can't handle me being trans then it wasn't meant to be to begin with.. but I don't want to hurt her all the same. What's worse is I'm a dumb @$$ and got involved with someone I work with. I don't want to make things awkward for her.

So I'm sitting here as we speak... she's texting me all kinds of sweet things... and I don't know what to do. I've thought, should I just leave her alone? Tell her we can't hang out anymore? Should I approach her and ask her if she knows? I'm so worried she's going to think I intentionally lied to her to deceive her.. but that's not the case at all.

Things that make me think she knows:

- The "Does it matter" comment
- She never touches my chest
- She has never tried to reach into my pants
- Everyone around her knows
- She never tries to take my clothes off, or questions me about why I sleep fully clothed
- She seems open about LGBT issues (Her brother is gay)

Things that make me think she doesn't know:

- We don't talk about it

I'm losing my mind! Ugh!

I'm sorry for the long post but this situation is soooo complicated! I really just need some ideas about how to approach her about this? Any input is very much appreciated!

Offline LanaR

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #1 on: December 07, 2017, 07:54:19 pm »
Hi there and welcome to the forum.

I don't want to be a Debby Downer, but aren't there some serious ethical and disciplinary issues you need to address re. dating someone you; a) employed and; b) presumably would expect to follow your instructions without question?

Sorry if that's only confused things more, but it's the first thing I thought when I read your story.

Lana

Offline PraetorianRhapsody

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #2 on: December 07, 2017, 08:24:12 pm »
I absolutely agree with you which is what is making this even more difficult. It's why I'm looking for advice. I feel like I'm falling down a rabbit hole.

Offline JessC

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #3 on: December 07, 2017, 08:56:52 pm »
Just be very careful going forward. As long as there aren't guidelines or rules that state you can't date within your workplace, I don't think there's much of an issue so long as you treat her the same at work as anyone else. Save intimacy for outside the workplace (coming from another law enforcement background).

At some point in time, you need to just go ahead and ask what she knows about your identity. It's better to get things sorted out now. She will most likely appreciate your honesty, and who cares if you find out she already knows - that's just a good thing!

Let us know how it goes. Best of luck.

PS: Law enforcement careers attract other law enforcement careers, generally speaking...just saying. ;)

Offline LanaR

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #4 on: December 07, 2017, 09:02:44 pm »
I can certainly sympathise with the dilemma you find yourself in, but I am at a lose as what to suggest that will help you move forward. Perhaps someone wiser than myself will have some suggestions.

Offline Lady Sarah

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #5 on: December 07, 2017, 09:20:23 pm »
In the event the whole "dating a coworker" thing is not an issue, ask M's mother if M knows. I'm sure M has talked to her mother about the matter if she knows. That way, you won't break her heart by springing it on her.
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Offline Floof

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #6 on: December 08, 2017, 03:29:28 am »
If the subject is so difficult for you to bring up directly, Lady Sarah's suggestion seems sensible to me.

Personally, I'd just spring it.. I do even with friends fairly early on, but then I'm also kinda weird and don't pass well so people can tell anyway! That said, dropped hints certainly make it seem she definitely knows, but I think its best to be direct and clear the air.. Preferably know from her own mouth how she feels about it!
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Offline Jailyn

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #7 on: December 08, 2017, 04:10:15 pm »
Look if you like her then the conversation doesn't need to be hard. You don't have to break it off. Let her decide what she wants or who rather. Ask her out on a date and plan to tell her or you can tell her in a letter. Just be honest and straight forward. Most people will not think you are deceiving them, some will think that but, most will not. You are male you are just unique. You are not crossdressing, which I would view as somewhat deceiving saying you are male. Find a way that is comfortable for you to tell her so that you are less stressed about it. The worst you can do is not being able to convey it. Then finish it off by how you feel about her.

Offline PraetorianRhapsody

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Re: Crazy over this woman. How to tell her I'm trans...?
« Reply #8 on: January 03, 2018, 04:11:02 pm »
So.. I wanted to come back to this post and give everyone an update. Firstly, thank you everyone for the advice!

Secondly... New Years Eve we were sitting at our usual hang out, having a conversation, and the topic of "what your mother told you about me" came up again. I had been stressed out for weeks and sick over this whole thing. She then told me "You've asked me this before.. and what did I tell you?" I said "you told me it doesn't matter". She then reminded me "It doesn't". I told her I needed her to be specific because it did matter to me. She then explained that her mother had told her I was Transgender long before she met me. I told her that I had been sick over wondering if she knew and she told me I was being silly and that of course she knew and I should have just asked her so I wasn't so sick about it.

I think my heart swelled about 10x when I learned that she knew the entire time. She is exactly the woman I thought she was and I'm smitten! It was the best way imaginable to start my New Year. Since then I've been able to fully connect with her and I'm entirely content. This woman is incredible!