The Stories

Daffy and the Transvestite

The participants in the story are Matt "they call him Daffy 'cause he crazy" Dabney and Max and Evan Steel.

It was Cape Cod, Summer of '98 or '99 (probably '98). Matt Dabney, Evan and Max were in a bar in Provincetown on Cape Cod during one of their annual summer vacations there. To give a little background, Provincetown is a mixture of tourists and gay people, mainly gay men. The night started at a local type bar where the drinks were pretty cheap. Literally a couple doors over from the local bar is the big bar/local hangout, the Governor Bradford. There is a big bar, stage, chess tables, etc... two levels, and onstage is a cross-dresser/transvestite, hosting a karaoke night. So they'd been talking about getting on stage and doing wild shit with the transvestite for a while.

So anyway, they're at this other bar this night, and Matt (in a somewhat drunken state) says, "Hey, guys, I'm thinking of going on stage and doing a song." And Evan and Max were like, "Ok, cool, we'll go too." And Matt was like, "Actually, you know, I'm going to go up and flirt with him/her, and stuff like that." And Evan and Max were like, "You don't have the balls to do that (no pun intended)." After a few minutes, Max said something like, "Matt, I'll pay you $10 to go up there and flirt with her." And Evan said, "I'll throw in $10." Eventually the ante was raised to about $30. Presumably it was $15 from Max and $15 from Evan, but Evan contends that it was more like $25 from Max and $5 from him, as Evan had only the $5. Either way, the boys continued to the Governor Bradford.

After hanging out at the Bradford (it was pretty close to being a full house), Matt put in to go up on stage and do a song on the Karaoke ("Swing Low Sweet Chariot", for the record). When it got to his turn, he got up there and bellowed the song out (he was pretty drunk). Then, the flamboyant and loud and annoying host(ess) "Ana" (prounced in the Spanish way, not the American) was taking over again, Matt in his microphone goes, "Wait, wait, hold on a sec..." And now Matt has the spotlight. The place gets quiet, and Matt moves into action. As well as can be remembered the conversation went like this:

[Matt finishes song and crowd claps]
[Ana begins to pick a name out of the bucket for the next karaoke singer]
Matt: Wait, hold on a sec. What's your name?
Ana: Ana.
Matt: Are you single?
Ana: What do you think?
Matt: Well, I'm hoping your single. Otherwise I wouldn't be asking.
Matt: So what time do you get off?
---here it gets cloudy. Ana says something about going out to his car or something like that.
[after a couple more lines between the two.....]
Evan: [from the back of the bar] He's being bad! Spank him!
Ana: What? You want me to spank him?
The crowd: YEAH!!!!
Ana: OK.
[Matt bends over and leans on the stool on stage. Ana gives him a nice hard whack on the bottom and the crowd goes wild!]
Crowd: YEAH!!!!!!
Evan: [from the back of the bar] Spank him back!!!
Crowd: YEAH!!!!!
[Ana bends over and leans on the same stool and Matt proceeds to spank his bottom. Matt then leaves the stage gets the much deserved congratulations from Max and Ev.]

Dabney and Evan agree that although Ana was obviously a transvestite, if he were a girl, he would be a good looking girl. As much of the Provincetown population was gay, there must have been a good number of people who felt that Matt's come-ons were truly heartfelt. There are a myriad of other things that make this story funny aside from the simple inane events of the situation. Thus it is a great stories classic.