Craigslist casual encounters weirdness: December 2015 (Boston MA) edition

The Thinker by Rodin

Today to spice things up and also because I’m getting a bit bored with these monthly postings, I’m moving my gaze east to Boston, about two hours away from me by car. With its larger, denser and more ethnic population it’s likely to be a wilder sort of place. Or perhaps people in Beantown are too busy ingesting their Dunkin Donuts (which overrun the area) than to attempt weird Craigslist hookups. Anyhow, I intend to find out.

First, let’s take a look at my Craigslist traffic for November. There were at least 199 web page views for these posts last month, up from last month. But overall traffic for this site was also up in November to 2746 page views, so the percent of Craigslist traffic dropped to an anemic 7.2%.

Anyhow, looking at the first page of casual encounters postings today, I can get a sense of who’s advertising. I see:

  • 46 men looking for a woman
  • 35 men looking for a man
  • 4 men looking for a couple
  • 2 men looking for a transvestite/transgender
  • 1 group of men looking for a man
  • 5 women looking for men
  • 0 women looking for a woman
  • 2 women looking for a couple
  • 2 couples looking for a couple
  • 2 transvestite/transgenders looking for a man

So maybe there are more heterosexual men in Boston than I expected. Usually men looking for men beat out the men looking for women. As a liberal area I would expect Bostonians to be open minded and kinky. Let’s find out:

  • She’s a young woman from South Boston and wants to turn a straight woman gay with her strap on. I don’t quite understand this logic but with her large derriere there at least should be plenty of inertia behind each thrust.
  • Women might want to avoid this 40-year-old black man from Boston. While it’s impossible to know how many sexual partners someone has had, it’s not a good thing when a poster shows pictures of himself having unprotected sex with a woman. Despite his “all natural” approach he does say he is disease free. If I were a woman considering him, I’d insist on a condom anyhow — maybe two at once.
  • She’s 30 and has “the biggest set of girls you have ever seen”. I’m guessing this means she makes Dolly Parton look underendowed. Men, if you like your women supersized above the waist, check her out.
  • He gets “a boner rubbing down a straight guy” but won’t make a move on you otherwise unless you want him to. By definition he won’t attract a straight guy, which may be why he is open to giving you a massage.
  • She is probably a he and is apparently the one flagging pretty much any ad. I guess it’s good to have an avocation but this is definitely an exercise in futility.
  • Are you an exotic dancer with a slim body that wants to dance (presumably for free) with a 63-year-old man from Wakefield? The proper response to this question is “Ha ha ha!” It’s not too hard to figure out this is the ad least likely to get a response tonight.
  • And speaking of us older men, here’s a 57-year-old married man from Woburn who is looking for a couple. He has a very odd submissive request that involves using a blindfold. Of course he can’t host!
  • What’s with all the older men posting today? He’s 58, married and from Medford and wants a couple, but really just the wife to play with but with her hubby watching. He says he’s into older women but I’m guessing he’s not that into them but figures at best that’s all he can attract. I’m trying to figure this out. First of all, at 58 what constitutes an older woman? Someone in their seventies or 80s? Maybe he figures it isn’t cheating if the husband is present?
  • But wait, there’s more horny older men. Here’s a 59 year old man looking for anyone to give him a hand job because wifey won’t put out.
  • Guys, she’s 27, Puerto Rican and wants to meet a husband’s naked body virtually on Skype. No you don’t get to see her and probably can’t hear her either so she is probably a he.
  • This 37-year-old man from Lowell better be ready to dial 911 because he wants a man to rip open his rectum. Let’s hope he is writing metaphorically.
  • He’s 35 and looking for a woman into incest, dogs, toilet play and diaper play. He really wants to be naughty, so he better anticipate coal in his stocking.
  • Usually Craigslist people want a big one but here’s a 44-year-old gay man from the Merrimack Valley into small ones.
  • Her idea of a casual encounter is a short-term place to stay near Chelsea.
  • She wants a job: a submissive boss who she can basically abuse. Expect her to come in late and leave early.
  • This is strange: She is 28 and wants a threesome with a man and woman who don’t know each other. She could probably make a go of this if she advertised for two men, but it’s filed under Women for Women. Oh, and she has to be the center of attention.
  • There is a lot of debate if “squirting” is real, i.e. not urine. She’s looking for a woman to show her how to squirt. I guess there is no Dummies book but if it’s just urination I have to think she can handle that already.

More in 2016.

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