Your most outrageous / amusing / moment in your transition journey ?

[Drexy/Drex]

Do tell : ) lets have a laugh
Mine is not strictly transition but I should contribute something
For me so far it was being dolled many years ago up by a trans and cis woman , when they let me look in the mirror, I couldnt recognise myself   thought wow I'd nail her instead they finished the job for me.....

[Mariah]

To this day it is the day that I got my ears pierced at Claire's and the spot where they do it is up against the window so on lookers can watch from behind. Needless to say I'm still amused to this day whatever they found to be so interesting and peculiar about me getting my ears pierced. Oh well, I guess I will always wonder what they were thinking. Hugs
Mariah

[Michelle_P]

Probably my recent shoe purchase...

It's now boot season, so naturally I need boots.  I went into a low price shoe store catering to women at a nearby mall, poked through the stock, and found a couple likely candidates in size 10. (Yeah, borderline for shoe store shopping.)  I sat down on a bench near the cashier and tried on a pair.  Nope, pinches.  The other pair, though, fit like a glove.  Perfect!

I stepped up to the counter with that pair, and without thinking pulled out my debit card.  Uh.  Out of order...  no card reader for me.  The cashier reache out and I handed her the card.  She swiped it, then said "I need to see an ID."

DOOM! In big fiery letters, even.  I thought "Here we go...", pulled out my old drivers license with a 15 year old image of me, 80 pounds heavier, and entirely the wrong gender, and handed it to the clerk.

Trying to make the best of it, I grinned, and said "It's a little out of date" or something like that.  She looked down at the ID, looked up at me grinning at her, looked back down at the ID and started giggling.  I think I made some remark about there having been a few changes, and we completed the transaction.

Humor seems to be the best way to defuse situations like this.

I said that I thought I'd wear the boots out, and she asked "Are you sure?"  I promised not to fall over, she smiled, and gave me a bag for my old shoes.

I guarantee this won't be the last time this happens, as I'm going to be full time for a while before my new ID is ready.  I gather that humiliation is supposed to be an element of the Real Life Experience from what my endocrinologist tells me.  Onward!

[Steph Eigen]

I don't know that I agree, Michelle.  Your anecdote about the trip to the bank after laser hair removal was a scream!

[Dee Marshall]

Michelle, I would almost bet that was DSW.

[Sinclair]

Probably my recent shoe purchase...

It's now boot season, so naturally I need boots.  I went into a low price shoe store catering to women at a nearby mall, poked through the stock, and found a couple likely candidates in size 10. (Yeah, borderline for shoe store shopping.)  I sat down on a bench near the cashier and tried on a pair.  Nope, pinches.  The other pair, though, fit like a glove.  Perfect!

I stepped up to the counter with that pair, and without thinking pulled out my debit card.  Uh.  Out of order...  no card reader for me.  The cashier reache out and I handed her the card.  She swiped it, then said "I need to see an ID."

DOOM! In big fiery letters, even.  I thought "Here we go...", pulled out my old drivers license with a 15 year old image of me, 80 pounds heavier, and entirely the wrong gender, and handed it to the clerk.

Trying to make the best of it, I grinned, and said "It's a little out of date" or something like that.  She looked down at the ID, looked up at me grinning at her, looked back down at the ID and started giggling.  I think I made some remark about there having been a few changes, and we completed the transaction.

Humor seems to be the best way to defuse situations like this.

I said that I thought I'd wear the boots out, and she asked "Are you sure?"  I promised not to fall over, she smiled, and gave me a bag for my old shoes.

I guarantee this won't be the last time this happens, as I'm going to be full time for a while before my new ID is ready.  I gather that humiliation is supposed to be an element of the Real Life Experience from what my endocrinologist tells me.  Onward!

*smiles* Love reading your posts ... makes me feel normal, I can relate. 

[Polo1962]

so.....not EXACTLY a moment regarding my actual transition but a moment that JUST happen that blew my mind because I don't RECALL it at ALL. I just got back from the store and my father (90 years old) had requested that I pick up some "Old Spice" aftershave (they don't carry it and he'd said to just pick up anything).
I did. I don't know why I stared at it so long and then got it.....it didn't seem quite up to snuff for my father.
It was "Skin Bracer" by Mennen. I unloaded the groceries as usual and put his things in front of him.
He said: "SKIN BRACER! BY MENNEN! I REMEMBER THIS, WE GOT YOU SOME OF THIS WHEN YOU WERE A KID!"
.....uh.......I'm sorry, WHAT??? I have no recollection of that. Interesting. I requested men's aftershave as a child AND MY PARENTS BOUGHT IT FOR ME! How cool is that?!
(btw, 6 times 6??? you're killing me here) 
>>> FTM, doesn't take much....but the fat globs hanging off my pecs will be gone soon

[Michelle_P]

Steph mentioned my little trip to the bank.  That was a monumental muckup on my part, where I sort of forgot how I was presenting when I went into a bank branch.  Details, details...

https://www.susans.org/forums/index.php/topic,214287.msg1897854.html#msg1897854

[Sophia Sage]

So I'm at this fundraiser a few months ago, making the rounds, and get into conversation with a lovely couple -- she's in a wheelchair, he's a bit short, so I end up standing at an awkward angle as I'm a little taller than average.  And then it comes out, her big question:

"So when are you due?"

She's pointing at my belly, and as tempting as it was, I had to fess up that no, I was not pregnant, I'd just gained some ungainly weight and my top was apparently unflattering.  And she's all apologetic, and I'm like half wishing I was pregnant, but at this point I'm just a wee bit old to be having kids.  Whew.  Anyways, it showed me that it was definitely time to start exercising and dieting!

[Vervain]

I mentioned this in my introduction post, but while I was assigned female at birth, my father raised me as male to an extreme degree. I'm honestly really, really, really glad that puberty blockers were not as easy to get when I was young, or my father probably would have begun transition against my wishes as a child. Anyway, I wasn't allowed to wear make-up or anything like that as a girl, and I couldn't live as female until I moved out at 18.

So, I moved into a household where one of my housemates was a very strong-willed woman who loved cosmetics and was horrified by what my father had done. She dolled up my face with gothic-style make-up, and I loved it.

Well... I tried to mimic the application myself, except, I didn't get it quite right. I'm afraid I looked rather clown-ish, and I went to V wailing about what had I done wrong? She couldn't stop laughing, but eventually took me into the bathroom, and helped me remove the eyeliner that I had somehow managed to get all over my eyelids, the eyeshadow that I had brushed into my eyebrows, and the lipstick that looked more like I had been having a serious make-out session with someone. She then sat me down and explained how to apply it and watched me do it to show me how to do it correctly.

But, wow, the first application I did was mortifying at the time. I look back at it now and laugh, because it was just SO overdone... and not in the overly dramatic gothic style I was trying for, either!

[CarlyMcx]

Last weekend in Las Vegas.  I was at the Fremont Street experience with my wife and a couple of her relatives.  I was in androgynous mode, wearing an oversize men's t-shirt over a camisole top, and a pair of women's Hollister skinny jeans, and a Coach man-bag over one shoulder.  I should note that my hair is now about 6 inches long, far beyond the short men's haircuts I wore most of my adult life.

My wife, her relatives and I were watching one of the live bands, a pretty good copy band that was grinding out Black Eyed Peas and Pit Bull songs, and we were dancing to the music, when this drunk, shirtless, homeless dude comes up and starts trying to dance with me!

That was the best pass I got all weekend.

[karenpayneoregon]

A week after bottom surgery I visited a near by mall, had to use the rest room and had to go standing up because of the colostomy bag required for the first week. There were several woman there that when I came out looked at me funny. I thought, one of them must have seen me facing the opposite direction from the toilet and not sitting down.

I smiled, lifted up my dress enough that they could see the bag and the giggled, went on my way.

Funny that I was living full time for two years prior to surgery and always used the womans restroom, sitting down and now I had the proper anatomy and could not and those ladies must likely figured me for a cross dresser.

[Jacqueline]

so.....not EXACTLY a moment regarding my actual transition but a moment that JUST happen that blew my mind because I don't RECALL it at ALL. I just got back from the store and my father (90 years old) had requested that I pick up some "Old Spice" aftershave (they don't carry it and he'd said to just pick up anything).
I did. I don't know why I stared at it so long and then got it.....it didn't seem quite up to snuff for my father.
It was "Skin Bracer" by Mennen. I unloaded the groceries as usual and put his things in front of him.
He said: "SKIN BRACER! BY MENNEN! I REMEMBER THIS, WE GOT YOU SOME OF THIS WHEN YOU WERE A KID!"
.....uh.......I'm sorry, WHAT??? I have no recollection of that. Interesting. I requested men's aftershave as a child AND MY PARENTS BOUGHT IT FOR ME! How cool is that?!
(btw, 6 times 6??? you're killing me here) 
>>> FTM, doesn't take much....but the fat globs hanging off my pecs will be gone soon

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[DawnOday]

None so far with transition. But when my first wife and I went to a college dance and ended up in the park and doing the nasty. The police helicopter with it's bazillion watt search light hovering overhead and I was past the point of no return. When the officer in the helicopter said. Get Off. I did just that. We ended up getting only a parking ticket. Thank the Lord because the alternative could have been statutory rape as she was 17 and I was 20. We married four years later.

[BeverlyAnn]

Since transition has just started recently I don't have anything humorous since.  However, I have had a couple of funny incidents in the past. 
Once during Pride in Atlanta my wife and I were walking through the park.  I was wearing denim shorts (shaved legs), t-shirt, earrings and my wife's white ball cap with my pony tail pulled out through the opening in the back of the hat.  So basically in male mode.  The Atlanta Feminist Women's Health Center was giving out stickers "Carpe Boobum" to remind women to do their monthly breast exam.  As my wife and I were walking past the booth, one of the women stepped out and said, "Hello ladies," and put the stickers on each of our shirts.  We still have that sticker on the bathroom mirror.

Another time I was helping a coworker, who knows I am trans, build a porch railing.  She and I decided to head around the corner to get a couple of Cokes at the store.  I was sweaty and covered in sawdust, no hat, nothing feminine except gold ball earrings.  When I was walking up to the door I passed three kids about 12-13 years old.  As I went in the door, I heard one of the kids say, "Hey, that was a lady!"  My friend overheard that from the car and was still laughing when I got back to the car.

[Drexy/Drex]

The other night at the wet mess after work there were about 20 of us sitting at one of the tables ....recently  one of the guys had his wife join our team  so this guy goes to introduce his wife to me in front of everybody ..turns to his wife to introduce me ...and says to her this is my wife mark !!!! I dont what he was thinking but it cracked the whole table up !!!!