"The Bet" Fact or Fiction ?

[Kelly DeWinter]

Sometimes I read a post about someone losing a bet and having to "Dress Up" as "punishment" and my inner skeptic comes out, This is NOT to say it doesn't happen. Today I ran across an old newspaper clipping where
a 2 police officers saw a lady in distress with her car, stopped to render assistance and were surprised to find instead of a lady , a man in a skirt. (auto hood up,working on engine) They arrested him on a bogus charge.

"Father of two Keith Res' s saucy outfit was complete with black panties, suspender belt and wig. He explained: " I'd dressed up to win a bet. It was childish.""

This article file date was 1980, but I believe it was from a 1975 newspaper.


Fireman Caught.jpg

I guess what we can take is that members of the TG community need to stop betting. LOL

Poor gal was also suspended from the Fire Department.

[Beverley Sims]

And, what about the footballer's dress up days because the also 'lost' the bet.


I only had one opportunity to 'lose' the bet, I was sixteen at the time.

I used to bet on race horses also and I lost all the time. :-)

[Robertacd]

Not saying that "the bet" never happens, but I am willing to bet %99.9999999 of the time that excuse is used, it's a lie.

And I will spend the day in DRAG if I lose that bet. ;p

As I said before, everyone knows that guys who are into forced feminization don't really need to be forced.

[Nikki A.]

Then again let's look at the bright side. Today this wouldn't even be an issue.

[Tracii G]

Its a common theme or excuse used by closet CDers that want to come out but just don't have the guts to head out the door.
Before anyone gets mad and has a snowflake fit we have all been there at that point in time where we were too afraid to walk out the door.
If you claim it was easy then I tend to disbelieve that too.
Its nerve wracking and scary to say the least.
The I lost a bet claim is a classic one and it has a 99% chance of being a lie.
It sounds plausible to them but not to many people here.

I would say just there is no reason to lie about your desire to dress and relate your fears to the folks here and get help overcoming them.

[Cristy2]

This article file date was 1980, but I believe it was from a 1975 newspaper.

It is hard to say for sure because up til the late 1990's and early 2000's it was not only against the law, it was a jailable offense and a huge fine to be caught crossdressed in public in most big cities and states. Thankfully many of those cities and states have officially repealed the laws, but in some places they are still very much in effect, just not enforced anymore.

So, back to the news paper story, it could have very well have been a silly bet, but it also could have been a guy lying his xxx off to keep from going to jail for crossdressing.

[Jodie_Lynn]

I'm not going to say it doesn't happen. In fact, the host of a YouTube channel that I watch, promised to do the show in drag if they were able to raise a certain amount for a charity. The goal was met, he honored his promise.


That being said, the "I lost a bet" trope has been used in about a gazillion fantasy stories on certain sites, and is probably the "go to" excuse for a lot of crossdressers who get exposed in RL.
Again, I'm not saying it doesn't happen, but I am e-x-t-r-e-m-e-l-y cynical when it is mentioned as a reason for dressing.

[Stephanie47]

How about the men who walk in heels for the annual "Walk in my Heels" fund raising events for cancer? The women in my office would watch the guys and try to figure out who was a cross dresser based on how adept the man was in walking.

[Tracii G]

The walk in heels is different its not a made up story nobody believes.
In my city I have never know CDing to be against the law.
Back in the 1920s there were drag shows and several well known transvestites.
Even thru the 50's some transvestites were quite famous around town.
During the early 60s as a kid we would ride our bicycles down town because thats where the cool stores were we didn't have any malls at the time and we would see them out walking in dresses and big hats.
It was never a big deal just part of the city's history.

[Jodie_Lynn]

How about the men who walk in heels for the annual "Walk in my Heels" fund raising events for cancer? The women in my office would watch the guys and try to figure out who was a cross dresser based on how adept the man was in walking.

What about them? It would seem, if one were going to do a charity event, one would want to practice in unfamiliar footwear.
You can't raise any funds if you snap your ankle in the first 50 feet.

[lingerieLiz]

I didn't know it was illegal until I was talking to a cop one day and he mentioned running someone in for wearing a dress. I guess I was just very lucky over the years.

[Michellebej]

I take almost the opposite stance.

I agree that it is rare, but a real occurrence.

Where I disagree is automatically thinking anytime I hear it that it's not true.

I was a criminal interviewer for a number of years, and the truly weird things I heard that turned out to be true; taught me early on to never discount someone's story out of hand.

[Beverley Sims]

One such law used years ago was, carrying articles of disguise.

Another all embracing law was 'Soliciting'.

If you were caught with a 'Red Foxx' recording you could be locked away, these days these recordings are on the internet for all to enjoy.

As Bob Dylan said, 'The Times They Are A Changin'.

[Teresa]

Kelly,
Maybe I wouldn't do it for a bet but I would do it if I could raise money for charity . I've found fund raising so much fun !

[alwayshave]

9-10 years ago, at my favorite watering hole, a bet on a NHL series led two opposing groups to bet the loser had to show up at the bar in drag. The losers did in fact show up in drag, one of the guys looked so good, that his long time girlfriend broke up with him that day. He made the comment to me it was not his first time dressed. So it does happen.

[MarinaTwelve200]

What about them? It would seem, if one were going to do a charity event, one would want to practice in unfamiliar footwear.
You can't raise any funds if you snap your ankle in the first 50 feet.

Indeed, In reading up on "womanless beauty contests", before we had one in church, it was recommended in many places to Rehearse always wearing the HEELS (if nothing else) so one will be used to them and less likely to have an embarrassing, or worse, accident. I am glad I did, as even having some experience, I NEWLY discovered a HARDWOOD FLOOR is like walking on ICE, Thank god they put carpet on the stage and runway----I nearly lost it, a couple of times, the first time We walked on the gym floor on the way to the stage.

[Molly Wells]

I've never used the bet excuse although I might have if I found myself unexpectedly having to make an explanation or excuse for dressing. I've been out in public many times but only "caught" once by a friend many years ago.
Interestingly though, I am in my late 60's and have decided to let my hair grow long. Right now it is to the bottom of my collar in the back and below my ears on the sides. I decided to go to the salon and get it trimmed and neatened up a bit as I let it grow. This was the first time I had seen this stylist and told her I was letting it grow. She asked why I decided to let it grow... "did you lose a bet?" I told her no, just want to. I am fortunate enough to still have a full head of hair and told her, "if you got it, flaunt it!"
Molly

[Crissy 107]

Pretty crazy that it was ever illegal, I had no idea about that actually happening.

[Robbiegirl]

Maybe this isn't quite the same but i swear with at least 3 different girlfriends I lost Bets where they were supposed to put on a Lingerie show for me if they lost and I would do what ever they wanted if I lost. Well in all three cases they choose to turn the tables on me and made me wear their nighties and lacy bra and Panty sets. It was great fun !

Now you have to understand that i liked girls that were a bit curvy and I am not that well endowed so fit was never the issue. Also I am well known for my sense of humor so these gals now I have a great playful side and would put on a fun show for them.

Since these girls were a bit curvy they all mentioned how much easier it was for me to model since there was no expectation of me having to look good. That being said since i was a runner and in very good shape it did bother me that they thought I looked a little too good in their frilly items. And yes The Bra was always stuffed with socks, LOL

[LilSissyStevie]

You should always follow "I lost a bet" with "and that ain't no lie" or "That's my story and I'm sticking to it" so that it's more believable.

[Leslie Mary S]

. . . Snip . . .
And yes The Bra was always stuffed with socks, LOL

How many packages of socks did you have to use? grin

[docrobbysherry]

Oh please!

Another T rationalization that every man wants to try on women's clothes? And that after they do, they're hooked for life?

[Majella St Gerard]

Once when I was out in man in a dress mode, a fellow walked up to me and asked if I had lost a bet, I just looked him up and down and said "no did you?"

[Leslie Mary S]

I have on three occasions made one of those bets. I intentionally picked the team I thought would loose. (he he). Well, low and behold, the under dog team pulled if off and won. The person I was betting with had to dress out all day in an Auburn blouse. Now I do not have anyone to make such bets with.

[MonicaPVD]

I lost a bet once. The only thing was I was already dressed.