Boys always lose...
First experience was me only watching like 5 girls storm our room with three other guys. They played strip . but i was too shy back then and refused. Who wins, chooses who strips. The girls were losing a bit, each a piece or two... then they got a row of wins and focused one guy, made him strip naked, ending the game. Kinda lame, but it worked for them.
Then with my first girlfriend i played once a strip card game. I took an extra item to make sure i win. She won twice, then lost whatever she could down to her underwear(if i didnt allow her to count the belt, she would have to take her bra off, but i was too confident). With my shirt still on (4 items) i was like "Gj man, next stop bra... she will totally get naked today." The more I was shocked after the four games when i got naked and she was still wearing that damn bra.
Then i played with a friend. We played a card game and after a few games i told her that if it were for clothing, she would have won. She insisted that if it was for real, it would be the other way around. We decided to try it. I had 8 items on (not even an intention), she had only four. i only lost once before i got her naked. Then we played for forfeits if she lost again. But this time, i lost all 7 items in a row and had to do a forfeit in the eight. That was really embarrassing. If she had socks on, which you normally have, she would not even get naked. But i still enjoyed watching her breasts he whole time i were losing.
With my second girlfriend i played many times, but never managed to make her loose her panties. She got me naked every single time and took advantage of that. She loved to trap me somewhere in a corner a make me with her hand. Btw as soon as we were not playing for clothes, i was winning mostly. And we played games where you only win by luck.
She even told me she played with two girls against four boys and although mathematickly they should lose like 2:1, the boys got all naked with one girl in her undies and the two mostly dressed.
With my current girlfriend we are only planning to play. She played only once in her life and beat the guy quiet terribly. But luckily, she usually gets nervous when we meet and looses everything so i hope this will be my first victory ever!