What's your most embarrassing transition experience?

[Julia1996]

Hi everyone.  I think most of us have an experience in early transition that seems like the end of the world at the time but is actually really funny to look back on.

Mine was an unfortunate experience at Walmart. Of course it was at Walmart, where else would an embarrassing moment happen?  I had just started hrt and my chest was still flat as a board. I wore a bra and put silicone breast forms in it. I was with my dad at Walmart and I bent down to reach for something and I don't know if the bra was too loose or what but both breast forms fell out and hit the floor with a slap. Of course that had to happen when there were 2 guys in the aisle with us. They were dying the were laughing so hard. I ran out of the store and bolted for the car. It was awful! I started crying. A couple of minutes later my dad got in the car and he handed me my breast forms. He was crying too because he was laughing so hard. I got really mad at him for laughing. When we got home my brother asked me what was wrong and why I was crying. My dad told him what happened. He said he was sorry that had happened and he hugged me. I thought at least he had some sympathy but then I felt his body convulsing. The big jerk was laughing! My dad told me I couldn't get mad at them for laughing because I knew good and well if I had seen that happen to someone I would have died laughing. I have to admit he was right. My dad told me not to worry about it and that I would never see any of the people who saw it happen again. Of course being the jerk Tyler can sometimes be, he reminded me that they have security cameras all over that store and that the security guys were probably still rewinding what happened and laughing. Then he said the next time I went in that Walmart they would probably track my every move to see if anything else was going to fall off while I was there.  That made my dad start laughing again.

So then a few months ago I got a fake cameltoe. My dad started laughing and said he hoped it didn't fall out on the floor like my breastforms had done. That made my brother start laughing and he said he could picture someone picking it up and saying " pardon me miss, I believe you dropped your pussy". Then they both died laughing.  You know, stuff like this is much funnier when it happens to other people.

[Devlyn]

Surprisingly, dropping my pants in front of various medical students doesn't make the list. 

[Kylo]

I don't want to be boring but nothing funny-embarrassing has happened to me yet.

Except maybe my own mother picking up and saying I got the wrong number thanks to my voice (I hope).

[Daisy Jane]

Good timing on this one because it just happened! Saturday night I was out sitting at the bar of a very corporate restaurant because I wanted some wings and a drink or two. I was sitting by myself because I'm new to the area and haven't made any friends yet. I ended up spending more time there than I intended because the girl behind the bar (we'll call her J) started chatting me up whenever she wasn't too busy.

Eventually this guy walks in and sits two seats away from me. Apparently he had been there earlier in the night because J said "You're back!" The guy started talking to me and we had a little conversation. When I asked for my bill I could see him out of the corner of my eye squirming uncomfortably in his chair, the look awkwardly at his beer, and then I heard him mumble to himself, "Oh lord have mercy!" Typically I'm oblivious to picking up signs that someone is interested in me, but I could spot this one a mile away, and I'm starting to wonder if the reason he came back is because he saw me before he left.

J hands me the bill and she asks, "Are you leaving me?" I told her not quite yet, but I wanted to pay up. I hit the bathroom and then sat back down at the bar. The guy wasn't there anymore and  J asks if the guy is bothering me. I said it's fine because the guy seemed harmless. After a couple more minutes he gets really awkward again. I knew this was gonna get a little uncomfortable but I could see he was dealing with some internal struggles
Him: So uhh <pause> Oh Lord <pause>
Me: What's up?
Him: I uhh, I'm really attracted to trans girls and...
I put my hand up to stop him
Me: I'm a lesbian.
His face turns a little red
Him: Ohh. I'm sorry. I feel stupid and ->-bleeped-<-ed up.
Me: It's ok.
Him: I've never told anyone before. I just have these feelings and urges and I feel these.
I suggested he would probably find it helpful to speak with a therapist to work out his feelings before he tries to meet anyone else. Then he started asking me questions about being trans and kind of word-vomiting about his current town being homophobic, his feelings, frequent apologies, etc. J overheard a lot of the conversation and was super uncomfortable. She told him multiple times that his questions were problematic and eventually she said, "This is so uncomfortable! It reminds me of when people ask me questions about being black!"
This conversation went on like one of the cringey scenes from American Pie, but for like 20 minutes. After very nicely  telling him several times that he needs to speak to a therapist he took a hint and left.

J closed up and asked if I wanted to hit the local dive with her. When we got there and sat down, one of the super drunk girls at the table reached over J and slapping my right boob repeatedly while shouting "Boobies! Boobies! Boobies!" J smacks her hand away and yells at her, then apologizes to me. I said, "It's ok. Not nearly as uncomfortable as the guy from earlier."

The end.

[KathyLauren]

Gosh, I lead such a boring life! 

My most embarassing moment was dead-naming myself to someone.  I had met her before in male mode, but she clearly didn't recognize me in girl mode.  So it should have been an easy pass.  Then I go and out myself with my old name!  D'oh! 

[DawnOday]

It seems whether wearing woman's shoe's or mens shoe's I still attract toilet paper to the bottom of my shoe.

[FreyaG]

Just the other week, I went in the wrong restroom at church by force of habit.  I don't know if anybody saw, but I definitely felt stupid.

[Danielle79]

Six months after starting HRT, I went to a local coffee house on a Friday afternoon with my son, then just short of a year old.

Sitting near me was a couple with a child, who looked about three. I noticed that the child was staring in my direction, but I figured he was looking at my son. He looked perplexed, like he couldn't quite figure out what he was looking at.

All of a sudden he shouted out, loud as could be, "that's a mama and that's her baby!" The thing is, I was in boy mode, in khakis and a button down shirt from work. I did have a pony tail, and my face was definitely becoming more androgynous from the estrogen, but I didn't think I was anywhere near male fail.

Anyway, his father pipes up, "no son, that's a daddy." No, the child insisted, "that's a mama and that's her baby!" That kid was absolutely sure of it. He kept saying it louder and louder, and everyone else in the coffee house started staring in our direction. The mom kept whispering, "I'm sorry, I'm sorry," and I just kept repeating, "it's okay." I hear the father say, "us guys have to stick together," pointing in my direction. It took all the strength I had not to burst out laughing when I heard that. He seemed perplexed that I didn't back him up with some grand display of manhood.

After about a minute of this, I decided it was best if I left, so I picked up my son, said one more "it's okay" to the mom, and left the coffee house. It wasn't until I got to my car that I finally felt safe to start laughing hysterically. That poor kid, he was right, but there was no way for me to say that without making the whole situation ten times more awkward than it already was.

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[Allison S]

I was walking in the cold with my hat, for some reason feeling myself. I decided since I'm feeling good I'll look people in the eye for once because that's something I always avoid. So I pass this guy and he's staring right at me as we pass each other. I'm wondering what could've caught his attention so much and thought I look good.

Turns out I had a piece of rolled up snot covered tissue stuck on to my nose. I felt so embarrassed and defeated. Who knows for how long I was walking around like that

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