Has dressing sexy ever put you in an awkward situation?

By dressing sexy, I mean wearing clothing out in public for the no-doubt-about-it purpose of flaunting your body, telling the world "I want you to look at me and desire me."

Awkward situation could mean many things: Running into your priest, having an old (also old in age) schoolteacher stare at you lecherously, etc. Basically an situatuion where your manner of dress caused you to think "Oh shit, not now, please not now."

Being a guy my situations have been very limited. I've never been caught wearing my wife's panties or anything like that. About the worse was when I was in college. I did a lot of running, & used to frequently wear running shorts as shorts. Don't laught too hard, back then running shorts were fashionable for women & men (try not to think of Richard Simmons), esp. at college. Running shorts didn't hide much, depending on what was in them, and erections were really obvious. Not a good combination unless "Check out this!" was the intent, and it certainly wasn't for me. There were a few times where I had conversations while holding my book bag in a strategic location. One afternoon my GF & I were kissing goodbye, which turned into some lingering, which lead to....you get the idea. When I stood up to leave, a group of students inside the bulding who had been watching us started applauding. I simply turned to them, nodded, and slowly gave my best bow from the waist.

Then I got the hell out of there as quickly as possible.

 

I wasn't dressed sexy by any means—not that I ever really did in those days—but thirteen years ago I was walking up the sidewalk on New York Avenue in Washington D.C. and was mistaken for a prostitute.

Oh, and I was wearing shorts and a t-shirt. What the what, now?

 

In my case, don't think dressing sexy is even possible.

 

Rogue, at one of my previous jobs we often used bicycle messengers. Nearly every guy wore shorts over their bicycle shorts, for modesty & because many of their deliveries were to investment firms, law offices, banks, etc.

One fellow persisted in wearing only the bike shorts, and was frequently reported for dressing inappropriately. He claimed that the extra shorts were uncomfortable. It was pretty clear that he wanted & liked the attention.

One time my wife went to the local liquor store wearing brightly colored bike shorts & an oversized t-shirt, which covered her pretty well (no camel toe, no see-thru ass). A patrol car stopped in the parking lot, & the police questioned her, they thought that she was a working girl. They eventually told her return home, and in the future be more careful about how she dressed.

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One night my & wife decided to go out. She intentionally chose a short, tight dress that showed plenty of cleavage (cut went almost went to the arreolas) & leg. That dress got us some very strong drinks at the restaurant. The very young Asian bartender couldn't keep his eyes off her breasts (back then 38C) despite trying not to stare, and it didn't hurt that my wife is naturally friendly & chatty.

The bad part is we ran into my then boss & his wife. They were staunch new right christians.

 

My wife used to receive a lot of unwanted attention even when she dressed modestly.

I'm a guy. I like women. I look. I know and practice the difference between looking and staring. Sometimes I'm surprised at how women react to being looked at, in general & I don't mean lecherous staring. I've seen some women, intentionally dressed totally hot, get in a serious huff over a quick look and I've seen women get POd when guys don't look.

 

I no longer dress over-the-top sexy (occasionally I will show some cleavage) but I used to often when I was younger. I don't recall ever feeling awkward because of something I was wearing. I've pretty much always been aware of where I was on the 'sexy scale' when it comes to something I'm putting on my body.

But like Damnitall said, you don't have to be wearing revealing clothing to be made to feel uncomfortable by attention in public. Quite the contrary.

 

One thing I've learned is, if caught taking a gentlemans look, a small smile of appreciation usually works better than looking guilty or quickly looking away.

 

I use to dress over the top sexy as well, when I was younger. Now, not at all, except for the bedroom sometimes.

Thinking about awkward positions and sexy dress always reminds me of thongs. Can't wear them, never could. Anytime I tried, I always felt I needed to fix my underwear. I'd go to the women's washroom to fix it, then realize... "oh, right!"

 

That reminds me of a Friends episode where they're having Thanksgiving dinner, and everyone is asked to name something for which they're thankful, Joey mentions thongs. Also saw one of the comedy showcase programs where a woman said the first she saw a pair of thongs she was like "What the hell is this? Underwear? This ain't underwear."

I'm certainly thankful that my wife (and other women) took to thongs like butter to bread.

 

Come on you know that's not how it happened. I've never taught at a university level and one's ever confused me with a professor, certainly not their own. Pfft.

 

I'm everywhere and anyone. Like Batman. Without the money of Bruce Wayne, the special gadgets or any special skills. But yeah, other than that "I'm Batman."

 

I think that the young bartender was doing more than drooling.

 

not on topic, but this one is for Tully

 

A related story. I was with my wife at the hosp waiting for her to get called to complete some paperwork. Sitting across from us were two no-doubt-about-it lesbians. An attractive young girl with a nice body, still high school probably, was there with her mother. She was wearing her volleyball outfit (volleyball was printed across the seat of her shorts, very attention getting). When she noticed the two women looking at her (not lecherously) she became very self-conscious.

 

Time to boil down what "awkward" means.

Generally the creepy guy, the unwanted stares are not due to the staring but due to who is staring. An ugly old man, creepy, a hot young guy, not creepy.

As man, its only come up a few times and I can't say it ever bothered me. I get a bit more of it at swinger functions being everyone is a potential play mate. I've joke I can turn women heads, but only if they are over 55, and I have and I can't say I was creeped out. Sex and sexuality is what it is, my wife and I don't care if you look, just don't touch.

 

When I was about 12 or 13 I was in Scouts. I used to volunteer at the Canadian National Exhibition where we would offer our services to help push people around in wheelchairs. I had to wear my Scout uniform which included shorts and knee socks. I had a creepy old guy follow me around wanting to talk. He came back to the office looking for me and would hang around.

Not sure if it was the socks or the fact that I was pre-teen blonde blue eyed boy... It was very creepy.