Has anyone had any unusual bets with their wife, girlfriend or others?

[Lea]

My wife and have started a bet that will run from March 1st till June 1.

In the past I have dressed only when I felt like it. If I was not in the mood or was lazy and did not want to go through the process of changing I did not change.

While I do have the option when I want to dress until June 1 the wife can also tell me when to change.

A few rules are in place. Such as it has to be at least for a five hour period and it will not interfere with our non-cross-dressing plans.

It is a complete change with makeup and a wig. Pants are occasionally allowed.

While we have just started this she has been having me dress on one of my days off and about four nights a week after work. The first night we started we painted our toe nails the same color.

We also had a five day mini vacation planned. A coworker of my wife was promoted so they canceled her vacation. I was informed that I was not to cancel my vacation and that I would be dressing the five days that we were scheduled to be gone. While five days in a row inside the house will be hard I am looking forward to it. We are going out of town this weekend and we will be shopping for nails for me to wear during the five days.

If I make it and dress every time I am told the wife does not win anything but she does not lose anything. However if she wins she wins forty dollars.

Wish me luck.

What are some of the other bets you have been involved in?

Lea

[Karren H]

When I was young I used to make bets with myself. If I lost I had to go home and dress. I lost a lot... Most. ALL!! Lol. How's that for unusual?

[~Joanne~]

Why are all these questions on the forum aimed at the out and about girls? just once I would like a question asking me how big my closet is, what's it made of, is there sitting room in it, what color it is etc, etc, etc lmfao good luck with your bet

[janedresser]

So I see I'm not the only one who likes to be 'supervised'. So, the bet is she can eventually get you to refuse to dress, and thus lose the bet. If I were you I would have offered more the $40 if you lose. Have fun, I know I would!

[Senneca]

Why are all these questions on the forum aimed at the out and about girls? just once I would like a question asking me how big my closet is, what's it made of, is there sitting room in it, what color it is etc, etc, etc lmfao good luck with your bet


Why does anyone have to ask you those questions on this forum if you wish to discuss them here? Start a thread about them.

[Jeninus]

Why does anyone have to ask you those questions on this forum if you wish to discuss them here? Start a thread about them.

Not to worry, this was taken care of.

[Alice B]

What a great bet. Wish my wife would propose it on me.

[RADER]

About 3 months ago, I bought on a whim a size 20 form off E bay for $ 100.00.
When my wife saw them she had me immediately order a size J bra to hold them.
When it came, she had me wear the bra and form 24/7 on a bet for one week,
yes 7 whole days. Well I did it, thank God it was cold enough to wear a heavy
coat to hide those rather large breast.
I now understand what GG go through with huge breast. I admit, I had fun wearing them.
Rader

[Chickhe]

Sounds like fun, but doesn't a bet usually mean you win something if you make it? For example, you get breast augmentation for a year and your wife pays you $100000.

[Aloha Jayne]

Why are all these questions on the forum aimed at the out and about girls? just once I would like a question asking me how big my closet is, what's it made of, is there sitting room in it, what color it is etc, etc, etc lmfao good luck with your bet

Excuse me Miss Joanne. Just how big is your closet and what is it made of? And is there sitting room? Oh btw, what color is it?

Ok, that was fun.

[RADER]

Sounds like fun, but doesn't a bet usually mean you win something if you make it? For example, you get breast augmentation for a year and your wife pays you $100000.

NO that would be to easy; I won a trip this summer to any 2 Railroad museums I want, And she has to enjoy the trip. LOL


Excuse me Miss Joanne. Just how big is your closet and what is it made of? And is there sitting room? Oh btw, what color is it?


Ok, that was fun.

About 8 years ago, I saw that my closet was way to small, So I built a 1400 SQ FT addition to the "Closet"
My wife took up 2 of the 3 closets I built in the addition, But I have a lot more room to roam around in,

Rader

[~Joanne~]

Why does anyone have to ask you those questions on this forum if you wish to discuss them here? Start a thread about them.

I wasn't being serious ;) Jeninus and scarlet decided to help me out in that department anyways lol


Not to worry, this was taken care of.

See? lol


Excuse me Miss Joanne. Just how big is your closet and what is it made of? And is there sitting room? Oh btw, what color is it?

Ok, that was fun.

No, not really, all it did was put me on the spot and my closet has has low self esteem issues and doesn't like me talking about them lol

if you really want the answers though...looky here: http://www.crossdressers.com/forums/showthread.php?170573-A-thread-for-Miss-Joanne.-Perfect-closet-%29

[Jillian Faith]

My wife and I bet occasionally with the winner getting a new purse, dress or pair of heels!

[ConnieD]

This happened to me several years ago. I like the women's hairstyles from the 50s-60s and often asked my wife to wear her hair like that. Finally we made a bet that the loser would wear their hair however the winner stipulated and would keep it that way for one week. Well, I lost. My wife then turned the tables and said I had to wear my hair like the women did in the
50s-60s! This didn't seem too bad, but then I didn't know I was headed to the salon for a cut and wet set followed by almost an hour under a dryer. After teasing and hairspray I was done. Of course it rained that day and my "do" got messed up. So my wife puts me in curlers and I have to sleep in them, but there was very little sleep time with a head full of curlers. I made it through the week, but I have a whole new respect for the women of that era, I couldn't do it. Way too much time and you never get any real sleep. I still admire the hairstyles, but I don't ask my wife to do her hair like that anymore.

[Veronica Lacey]

Hi Lea...

Sounds like a very entertaining exercise for you both (more for you, of course.)

No bets here as my wife is only partially supportive. What she did permit is that I take some time off and have three days in the house to myself while she is away visiting her parents (that is this weekend.) All my male clothes are locked up and the keys rather difficult to obtain. I must wear only items in my femme wardrobe. Not quite as spontaneous as your arrangement but it will certainly do for a decidely closeted cd like myself.

Let us know how things go.

Veronica