Have you ever lost a bet to a girlfriend as a way to introduce them to Crossdressing

[Robbiegirl]

For me this has always been a fun and funny experince ! I just never had the guts to tell them how much I really enjoyed it. Also since I tend to like women who are abit curvy, thier clothes always fit !

I have been in 5 situations with Vanilla Girlfriends where I lost bets (on purpose) and have had to model their Lingerie. In almost every situation their actions were the same.

1. Evil Grin as they handed you the lingerie you had to wear
2. The lingerie was always the girliest items they had which I had never seen them wear
3. The joy in thier eyes as they put you into a bra, adjusted the straps and then snaped it in the back on purpose
4. The gushing array of compliments on How "adorable and cute" you looked in Bras, Panties, and Babydolls
5. The Constant Giggling
6. And worst of all the continued asking of the question " do you like wearing women's lingerie ? Would you like to wear my Bras and Panties to work ?
7. And when you think it can't get worse they yell Smile and the flash of the camera goes off!
Please add anything I missed or is different in your experinces

If nothing else I always thought they could see that it can be fun and not threatening

[RADER]

My first wife would holler and scream to get the clothes off, wanted to know what was the matter
with me. and if I should be committed to a mental institution.
O' Yes, those where trying times.
Rader

[Brandy Mathews]

Never done that but it is good idea. Sounds like fun.
Hugs,
Bree :)

[pamela7]

not quite, i did use a bet as a reason to come out to a colleague, and from there could come out to others.

[kimdl93]

No. Honestly, I've never been involved in a 'bet' that in any way involved CDing. I guess I've lived a sheltered life.

[Beverley Sims]

When younger.......
I would get introduced in more subtle ways.....
Then I got married.

[Closeted Kat]

I have not, but wished I could. I'm too shy and have few female friends. also i'm larger than all of them...
-kat

[Nadine Spirit]

I guess I've lived a sheltered life.

Lol, me too!

[valeriesue]

I only had this kind of bet once but I ended up winning the bet so I did not get to dress up but what I won was well worth not getting to dressed up for it.

[giuseppina]

I've seen some posts and threads like this one

http://www.crossdressers.com/forums/showthread.php?13841-How-to-tell-your-partner&highlight=

that say it isn't a good idea to joke around with a prospective life partner about crossdressing. Yes, the thread is 9 years old, but the message still applies.

The gist of the above thread is "Tell your partner simply and honestly with no joking around." Your partner will appreciate it.

[Sarah-RT]

Yeah did that once when I was 12 maybe with a GG childhood friend. We had a sleep over and she did ballet so after 'losing' at something I got to wear her tutu and leotard

When we went to bed she slept in her parents room and I was given her room so I wore the skirt to bed

[Jessie James]

Not quite a bet but when I was around 4-5 years old, my older sister said she would give me $5 if I would let her dress me up. I agreed and she dressed me up in a white frilly dress, blonde curly wig with a bow and she put full makeup on me. She had also called one of the older neighbor boys (whom I was friends with) over to our house and introduced me as a new girl in the neighborhood. I got into the act and said "Hiya big boy!" :battingeyelashes: I don't remember ever receiving that $5 but I didn't care.

Jessie~☆

[emma-louise]

Never done it myself but love the idea x

[Lily Catherine]

Never been close to losing such a bet; 70 push-ups was the worst I got from betting thus far. I kinda feel that's taking long-term cross-dressing a bit too lightly, considering that it's with a prospective life partner of all people. Otherwise, as far as coming out to close friends goes, it's a legitimate possibility to 'come out' by this means. Of course, their reactions to you cross-dressed are a totally different story... :straightface:

[Jenniferathome]

And losing such a bet does nothing to inform your partner that you are a cross dresser. I think this notion of "introducing" cross dressing via trickery or some planned leakage is absurd. Cross dressing is not in the lexicon of the average female. It is a leap to get to "cross dressing" not a gentle step.

To to anyone who plans on telling your spouse, do it in guy mode, and do it completely.

[Robbiegirl]

We are all different! For me this was a way to open the conversation and for them to realize this could be fun ! A couple took notice and commented that I seemed to be enjoying it a bit too much. Since the sex was always great afterword the women could at least tell That I was totally Hetro !

[NicoleScott]

I wonder what the bet was that E.T. lost. Did he lose on purpose? Was E.T. not a he?

[Maxie]

In high school I lost a bet on purpose so I could wear a cheerleader uniform to a post game party.

[SherriePall]

Never because I am a sore loser.

[Tina_gm]

Any man who takes a bet to dress as a woman is certain to lose that bet....:heehee:

[rachael.davis]

There is a nice "underwear that's funterwear" shop I like, the ladies that work there joked that in couple of days they would be inundated with men who had lost a world series bet with their wife/girlfriend and now had to dress up as (whatever) for Halloween.
I said "and you believe it"?
One of them said "for a couple of hundred dollar sale there are lots of things I'll believe"