Truth or Dare in a hot tub [MF] [FF] [MM]

The folks over at /r/gaystoriesgonewild thought some of you guys might appreciate this, so here goes:

A while back, I wrote a story about back in the early ’00s and a truth or dare game. Those games are always good for a chuckle or two..and I haven’t played one since…well, since back before the wife and I were married. But as it turns out, you’re never too old for kid games.

My wife is on one of those ‘deal of the week’ email things for vacations. Usually, they’re kind of shit-shows, due to the travel dates being some of the worst times possible. She’d actually found one that ended up being a pretty good deal, a pretty good destination, and pretty good timing.

Things were going to work out very well, until she let me know that we’d be going down at the same time as one of her friends and her husband.

[M]y [f]irst Craigslist experience

I work about an hour from home, so I have a long drive to work every day in the early dark mornings. Mostly country roads with few other drivers. Many times I have jerked off while driving to keep myself awake and entertained. Usually I’ll cum in an old sock and chuck it out the window. A few times I’ve even brought my fleshlight and fucked it while driving. No better way to start the day than with a powerful orgasm!

Well, I’ve grown tired of doing the work myself, and I make decent money now, so I decided to look at other options. Specifically, I’ve been looking on Craigslist for erotic massages and the like. There’s not much to choose from out in the boonies, but they’re around. Eventually I found a promising listing from a woman servicing guys out of her home. She required a quick meet and greet at a local Mc Donald’s before giving out the exact location of her house. So after emailing her what I’m looking for, we set up a meet.