Ever suspect a friend of yours is a dresser?

Back in high school I had a good friend. He was one of the popular boys and we would hang out after school now and then.

Over the years, several little things happened that makes me think we might have shared other interests than what was out in the open.
The following two events especially made me curious:

- The whole class was together for a costume party at one of our teachers home. Sometime late in the evening, my friend was talking to his female cousin who was also in our class. She had already changed out of her costume which was something overly girly, including a long skirt and a cute top. All of a sudden she started helping him put it all on, and next thing you know, she was doing makeup on him and putting on lashes. Fun party, good music, and we all had a few drinks by then (I did not grow up in the US, just so you know), so nobody paid much attention to this .. other than me! I was sitting watching this play out with great interest.
What I distinctly remember, was that he was visibly shaking while he was being "transformed" and I recognized that excitement and nervousness from myself when I was dressing or applying makeup in secret.
He stayed in the outfit the rest of the evening, and was swirling and being girly, but not the comic "Look at me I got balloon boobs!" typical boy playing girl style, no he was into it.

We never talked about it.


- We were on a school trip to a big city in another country and he and I had gotten separated from the rest. We were just wandering around a shopping area in town and walked past a bridal shop with 2 gorgeous white dresses in the window.
He stopped and stood there for a few minutes, just staring at the dresses and then suddenly said "You and I would be so pretty walking around in those dresses"!

There was no "Ha Ha Funny" moment, just silence. I can't remember, but I don't think I said anything back, but I sure was thinking!
A moment later we wandered off, and nothing else was said.

I haven't seen or talked to him in many years and don't know what happened to him, but I always wondered if something was going on there.
As I am writing this, I can't help but think there is the possibility that he might actually read this and recognize the stories, and connect the dots! Wouldn't that be interesting!

What do you think?

And, have you had anything similar happen that gave you a hint that a friend might be just a little bit off of the average male gender point?

- Suzie

That's a fascinating story. I have not had anything like that happen.

But, I think I was probably the friend in that scenario once, a decade before I started dressing. I'd been to an local upscale mall and one of the major department stores had a Ralph Lauren section. I noticed a rack of little black dresses and had to stop. I wasn't looking for myself as I hadn't considered dressing like that at that point. The changes in my wife's figure would not have allowed her to wear that particular style. I had to stop and i nonchalantly checked the prices which were in the hundreds of dollars twenty years ago. i was shocked.

I was at a family gathering a while later and somehow i mentioned that I'd seen these dresses and how expensive they were. My nephew quickly made a comment about how he didn't know I was into that kind of thing and I just stammered something that I can't recall. I was always into shopping with my wife and I think I was satisfied in those days by getting my 'feminine' needs met by proxy back then. Later, not so much...

I did work with an engineer once who lost a fantasy football group bet which required him to either pay a certain amount or wear a dress to a sports club. He chose a red dress and I heard he was totally cool with spending the evening that way. I wasn't there but word got around. Ya' just never know...

I had a "boy friend" when I was 13 who used to bring a bag of his sister's things when he would come over to visit. Bras, panties, slips, pantyhose and cute little dresses.

We would dress up and lay in bed and hold each other and make out. I loved it. Lasted about a year and they moved out of the area and I never saw or heard from him again.

Sure was fun, and the only other person I ever dressed up in front of (besides my wife). But no...never encountered anyone I ever knew irl that actually crossdressed. Would sure love to though.

Suzie, It sounds to me that you are right on the money with your friend. It would be interesting to know what he is up to now.

When I was nine years old, (fourth grade), a male friend came over to play after school. We had swings and a jungle gym in the back yard - and a golf course was our playland beyond our yard.

He wanted to play Barbies. I thought nothing of it, brought out my Barbies, we dressed them up, pretended that Barbie had the job that fit her outfit (nurse, flight attendant, doctor - Barbie could be anything and everything). His mom picked him up and I realized one of my Barbies was missing. Later his mom called and said Tom had my Barbie and she would drop it back off.

No big deal - but he never came over again and we really weren't friends again more (his choice).

He committed suicide in high school. I was devastated.

Now thinking back of that incident now as adult, I wonder if he had some gender dysphoria going on. I often think of how conflicted he must have been as a nine year old child.

No one that I considered a friend. I remember a girl friend from high school commenting on the somewhat obviously feminine traits of a younger classmate. She mentioned visiting his home and specifically how he had decorated his room in a decidedly feminine manner, although nothing was mentioned about his clothing preferences. She was not hypercritical of his apparent femininity, but if she had spoken somewhat positively about it, I might have been tempted to share my own secret.

Oh no Char, what a terribly sad story! I am so sorry to have caused you to remember.
Who knows what might have caused him to end it, but it certainly sounds like he might have been struggling with some inner conflicts for a long time.

Well, now that I already have tears in my eyes, I will share this sad story that I overheard my parents talk about one evening when I was very young. My dad was devastated and I know it left a significant scar.

Someone at the office where my dad worked had come in one day completely dressed as a woman, purse and all. For some reason the purse was an extra big deal, which I don't really understand, but it stood out as making it extra bad as my parents were talking about the incident.

He had requested a conversation with their manager and had asked to be transferred to a different job where he could work as a woman while still being around the colleagues he loved to work with. He didn't care what the job was, anything all the way to cleaning lady, as long as he was allowed to dress and be treated as a woman.
The manager told him absolutely no, and then made fun of him in front of the whole office.
The next day he did not show up for work and someone found him that evening.

I don't know, but I have always had a feeling that this event was part of the reason my parents reacted poorly to figuring out that I had a thing for girls clothes. It has had a direct effect on me over the years and made me, if not understand then at least know, that this thing in us can be so powerful and that negative reactions to it from others can have devastating effects.
I know all too well that several here have seen how badly it can go.

Sad to hear that. But on a brighter note, maybe your friend will pop up on this site.

Hi Suzie:hugs:. Many _ Many years ago I had a friend that I wasn't sure if he was Gay, Strait OR a CDer,

I really never found out for sure, >Orchid**O:daydreaming:O**

I have a large male friend group. There was a bet over a sports final where two opposing groups bet the losers would show up to our local water hole in drag. After the final, the loosing group showed up dressed. Three of the group didn't look that good, one did. When I commented on his looks, he stated it wasn't his first time dressed. I didn't push it any further. Interestingly enough, his girl friend broke up with him that afternoon.

Uh oh Jamie, that was probably not so good.
I have to admit I laughed a little when I read your story, but I guess it might not have been that funny.

Girl friend goes "Oh, That explains it!"

It is the old dilemma, and the reason I have never gone out dressed as a girl on Halloween, well one of the reasons. I don't want to make a mockery of "being a woman", but if I do it as good as I am capable of, there is going to be a lot of raised eye brows!

Edit: I did actually dress as a girl for a costume party one time in my early twenties, it was held at a local bar and when I arrived, they refused to let me in because I was not wearing a costume!
It took a good bit of arguing, AND me finally pulling off my wig, before one of the bouncers suddenly got a really weird look on his face and went "Oh Shit! Sorry dude, I didn't realize .. "

It as a fun night, and I did not pay for a single drink!

Hi, Susie.

Re the second event you describe in your opening post, i.e. that at the bridal shop, I'm intrigued: do you think it might be possible that YOUR friend had actually wondered similarly about you and that his words had been a way of testing the water?

I cannot think of any occasion when I was prompted to wonder about a friend or acquaintance of my own but I suppose statistically (but which estimates of crossdresser frequency is right - who knows?) I probably do know or have known someone who is also a dresser. You've got me really wondering now....

Fi.

Fiona,

I suppose that is possible, but thinking back on the situation, I think there would have been other hints if that was the case. I could certainly have slipped up and missed removing some makeup or polish or something, but I was extremely careful not leaving any evidence of my dressing back then, still am, so I dont think that was it.
Good suggestion though, thanks!

I ran into someone at a support group meeting. I commented she reminded me of someone I worked with
Not that I thought it was her. Then he takes out his work ID. I couldn't belive we've work together for w
10 years. She recognized me at an event 8 years prior and never said anything till then. Big company so we don't work side by side. She's always been nice to me when we do

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Originally Posted by Suzie Petersen

Edit: I did actually dress as a girl for a costume party one time in my early twenties, it was held at a local bar and when I arrived, they refused to let me in because I was not wearing a costume!
It took a good bit of arguing, AND me finally pulling off my wig, before one of the bouncers suddenly got a really weird look on his face and went "Oh Shit! Sorry dude, I didn't realize .. "

It as a fun night, and I did not pay for a single drink!

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I've gone to my Meetup outings in a girl costume probably a dozen times. But I don't go out as a regular girl. I go out in some kind of fantasy girl costume. I've been a Hooter's waitress, Wonder Woman, a mermaid, a Geisha girl, a harem dancer, Victor/Victoria (a mon pretending to be a woman pretending to be a man), among others. I love developing the costumes.

Once, there was a group of GG flight attendants waiting for their ride to the local airport. I walked up to them and said, "I really like your costumes."