Did you ever lose bets to women on purpose where you ended up in thier clothes

[Robbiegirl]

OMG ! Growing up I had so many fun experiences with Girls and then women where I lost bets. I will just start with the first that involved my two sisters and my poor best friend when I was about 8. I fell on purpose in a race and as a result my two sisters got to dress us in one of thier many Ballerina costumes. I mean everything including makeup tights ballet slippers. And of course they picked the prettest full tutus they had.We had to take a lesson from them in front of thier squeeling and giggling girlfriends. I pretended to hate it but loved every second

[jennloves55]

Oh yes I would have loved that too. I lost one to my SO one time so that I had to dress for a drag show to raise money for a local charity. I was really upset about that. lol If she only knew.

[AngieStone]

Robbiegirl I was never smart enough to come up with that great idea!

[vallerie lacy]

Some girls have all the luck. I can only dream of that happening.

[Karren H]

You should go to Vegas and bet against yourself.... you could make enough money to go buy yourself a whole new wardrobe and one for every girl you ever lost a bet to! lol

[JocelynJames]

Never any sisters,5 brothers( I guess I was the sister!!) My ex once wanted me to dress as a cheerleader for Halloween and then backed out when I was "too interested"

[Danica]

What a great story! How excitingly fun that must have been. Wish I had thought of that years ago when I played with the cute neighbourhood girls. Back in college, when I was dating my ex-wife, she dared me to put on her panties. At that time, I was suppressing my dressing, but I took her up on that dare and suffice to say the results were amazingly delightful. The pink fog was unleashed and I come out to her shortly thereafter. There were ups and downs after that, but that is one unexpected evening that I still remember with fondness.

[Cheryl Ann Owens]

Way back in my junior year of high school I was dating a gal while supressing my CD feelings. One day she told me she'd like to make up my "pretty blue eyes." I almost choked wanting to say "Yes, Yes, Yes!" but the supression took over. Damn! I should have let her! It may have gone way beyond there because she was very, let's say, liberal about trying anything. Someone kick me!

Cheryl

[Cheryl T]

Oh Yes...when I was young (like 11 or so) I'd make bets with my female cousin and purposely lose to have to wear her shoes. She had these adorable patent leather Mary Jane's and I just loved wearing them.

[Robbiegirl]

When ever I made one of these bets I would kind of set them up for what I wanted.

Like i would make a tennis bet and then tell them they had to wear their tennis dress the rest of the day while they served me ! Back then the dresses came with show panties with ruffles. Of course an evil grin would come accross their face as they told me " fine but if you lose you have to wear the dress and the panties "

[JRZSHORE]

Very clever and what fun

[Linda Leigh]

what a great idea and fun. I would have never thought of that

[RADER]

About 5 years ago, I bought some forms from "Janet's Closet"
When they came, I could not wait to try them out; So when i put
on my bra and forms, It gave me a solid "C" look. I showed them off to
my wife and she started laughing, saying you would not want to wear them
all the time. O I would if I could, and wish they where bigger.
She then asked me how big to them come, I saw that I saw a size 24 on line.
OK, You get them but You Must Wear Them For 2 weeks strait, no taking them off.
Well I did, had to get a size "J" bra, but i did wear them for the 2 weeks.
I won the bet; I got to pick where we where going on Vacation.
WOW, those boobs where heavy.
Rader

[monalisa]

I bet a girl on who would win a college basketball game and the loser had to wear a french maid outfit and wait on the winner for 2 hours. I felt like I won when I was in the maid's outfit. She still enjoys reminding me and asks me if I want to bet again which I love to.

[brassieres]

I never had that opportunity to lose a bet wear I had to dress as a girl.

[Courtney Ramona]

Never lost a bet mainly because no one ever bet me to do anything like that. But one year a friend said I should be a girl for halloween. I was like NO WAY!!!! But on the inside I was like finally Let's do this! so the summer goes by."With her never shutting up about it!" Fall rolls around and "I finally gave in." lol, So you can guess what was for halloween that year! I mean I was forced into really .

Not really a bet but good enough for me.

[MissTee]

No, but oh how I wish.

[Beverley Sims]

No it was always the women betting against each other to see whose clothes I would be dressed in for the night.

[Robbiegirl]

As I got older the bets always involved that the ladies would have to put on a lingerie show for me ! OMG ! The wonderful Babydoll nighties back then were so girly and all had ruffly panties ! I also looked and felt like a princess having to walk around in the long silky Olga Night gowns. Again it was so much fun for them and if they only knew how much I was loving it

[Kate Simmons]

Not really but I always seemed to have the knack for winning at strip poker.

[kimdl93]

Let's imagine the details of this situation...who suggests such a bet? You or a GG? I honestly have never encountered such a circumstance. I doubt that most GGs devote a lot of time to thinking of games that might get a male into their pants...or clothes.

[brassieres]

Let's imagine the details of this situation...who suggests such a bet? You or a GG? I honestly have never encountered such a circumstance. I doubt that most GGs devote a lot of time to thinking of games that might get a male into their pants...or clothes.

Yeah, women generally do not want men in their clothes, unless it is to embarrass them. Sometimes I would taunt women online about how pantyhose cannot be uncomfortable and that they are over stating their case just to get a rise out of them and see what they would say.

[Flirty_Fantasies]

What excellent ideas! I'm totally enthused about these strategies. Thanks, Girls!

Happy New Year to all!

Janelle

[giuseppina]

You`re mischievous, brassieres.

[Foxy Lady]

Many years ago my sister-in-law was out with my wife and me and she spent a good part of the day complaing about her girdle. After a while I started teasing her and after a while she said she bets I couldn't wear abra and girdle for an hour. I told her if she bought them I would wear them. She then said I would have to wear nylons a skirt and top, I eagerly agreed. I spent the following weekend fully dressed and in heaven. It was after that my wife told her I cross dress.