It is a matter of slight embarrassment to me that my first writeup on E2 was on the subject of strip poker. It probably gives some insight into the mind of my sixteen year old self. Nonetheless, there it is and it has remained here this last decade for nearly two decades (fuck me!) It was revised sometime around 2010 and I might give it another go at some point.
On the origins of the game
Poker, in one variant or another has probably existed for as long as there have been playing cards. It is afterall at its simplest merely a game of guessing whether your partner has a better hand than yourself.1 It is therefore more a game of body language and concealed emotion than of the fall of the cards themselves. A skilful player can bluff on a bad and still come out on top. Consequently, the most important element of a good game of poker is risk. A player with less to risk, who does not care passionately about whether they win or lose the next hand will be far more inscrutable than one who has everything on the table. Equally the mechanic of the game itself is not so compelling as to maintain an interest in the game on its own, it is the thrill of risking a high stake on one hand that gives the game its timeless quality.
Arguably then, poker is best played for high stakes, however, most people are not in a position to stake a fortune on a pair of jacks. For one thing, it requires a fortune which most people do not possess. Young people in particular rarely have a call on sufficiently significant resources. There are other risks however that they may be persuaded to take. After all, the acquisition of material possessions is for many people a secondary consideration – coming just after the acquisition of a romantic and consequently sexual partner. It is natural then that a game like poker that is so focussed on understanding the emotions and reactions of the opponent would become linked with sexuality. Strip poker, it is suggested, was born of this.2
Rules
The problem with strip poker when compared to poker played for money is that there is little room for raising the stakes. A person can only wear so much and even if shoes, socks, belts, etc3 are counted separately rather than as pairs, no-one is likely to be dressed in more than nine or ten items. Furthermore, winning back items of clothing is usually impractical. Now, obviously if you're basically just playing as an elaborate way to get naked then this won't matter too much, and you can just play a straightforward game of 5 card stud where clothes are bet, potentially everything on a single hand. In fact I suspect the majority of games are played like this.
If you do want a longer game and one with genuine skill then you have a variety of options. A simple way to play is to bet chips as usual and in addition to the winner getting the chips, the loser (or losers) removes an item of clothing. If the chips don't already represent money they can represent clothes – five chips lets you buy back a lost garment for example. You could, if you are really taking it seriously, assign different chip values to particular items.
Cheating
As you might imagine, a lot of cheating goes on in this game. From taking advantage of another player's misconception that two-pair beats a full house to genuine losers refusing to part with some essential protection from the element, whether through bodily insecurity or the sudden realisation that one's underwear is a little worse for wear.
There are really two ways to deal with this. Firstly make sure everyone really is willing to play and they aren't just going along with it. Seriously. Consent is incredibly important. Establish, if you like, how far people are expected to go. Secondly, make it a part of the game. Obviously, no-one should be pressured into doing anything they don't want to, but a little friendly teasing and cajoling is very much part of the spirit of it, but only once the game has begun and should not be taken too far. If someone decides that actually it's gotten uncomfortable, let them back away with good grace. And give them their clothes back.
1For a discussion on the history of poker see Wikipedia - History of Poker Poker, although the unique qualities of the game may have evolved in the 19th century, it is clearly descended from earlier betting games.
2Wikipedia ibid suggests that the Strip variant of the game emerged in the brothels of New Orleans in the 19th century and the term was first used for a non-sexual game amongst boys in the 1920s. I suspect that this is a pedantic interpretation of the term 'Strip Poker' and that card games where clothes are the stake date back far longer.
3Earrings and jewelry is definitely cheating. With the possible exception of nipple rings.