The Thinker

Craigslist casual encounters weirdness: March 2016 (Worcester, MA) edition

In my monthly samplings of weird but reasonably local Craigslist casual encounters postings, I’ve missed Worcester (it’s pronounced “wooster”), Massachusetts. It’s about an hour east of where we are living. I don’t think about it principally because I haven’t visited it, just driven through it instead. But it is Massachusetts’ second largest city with close to 200,000 people. Situated a bit outside Boston’s outer beltway, it’s had a reputation for being a faded industrial city, one of many here in the Northeast. It also has its own Craigslist community so it’s likely to have plenty of people into weird stuff. I’ll get to that in a minute.

But first, let’s take a look at my February Craigslist post statistics. It’s been a very slow month for fans of my Craigslist posts. I can document at only 156 web hits in February, but site traffic in general was very slow last month. There were just 1514 web page views, so my Craigslist traffic was just ten percent of total traffic. 69 of those hits were for my popular May 2015 post about Hartford’s Craigslist casual encounters postings.

There is a light snow falling here today. Let’s see if this is suppressing the creativity of posters in the Worcester area. Pulling up the first page of posts I see:

  • 25 men looking for a woman
  • 61 men looking for man
  • 4 men looking for a couple
  • 2 men looking for a transgender
  • 5 women looking for a man
  • 0 women looking for a woman or a couple
  • 0 couples looking for anyone
  • 1 transgender looking for a man

So right off the bat it looks like men will be dominating the posts this month. Here we go!

  • Do you know what a tribute is? I mean in the kinky world of Craigslist. I had to look it up but it apparently involves a man jerking off on a picture of a hot woman and perhaps sending it to the woman hoping she will be aroused. If I were a woman and received one of these I would be calling the cops not to mention running for the Purex! In any event here’s a definitely weird post from a 52-year-old man from Acton looking for a man who will jerk him off on a picture of his wife. Curiously you have to do this while he is actually watching her, albeit surreptitiously, clothed or naked. Wow! This is exactly the sort of gem that makes this area so special! Just when you think you have seen it all, something new pops up. And it was the first post at the top of the page!
  • Even if you are “gurl” friendly, you will want to avoid this ugly “woman” from Milford. “She” gives you plenty of pictures just in case the first one isn’t enough to convince you to hurry to the next ad. Maybe you should choose this 37-year-old gurl.
  • I’m definitely behind on how sex reassignment surgery is done. Not feeling the inclination myself, it’s a mystery to me how the surgeons do this magic. Apparently in male to female surgery, the surgeon gets to shape the new woman’s private parts including her most sensitive spot, the clitoris. And that’s what this 51-year-old Worcester man is looking for: a new woman with an extra large clitoris. Presumably nature doesn’t provide this naturally to many women. It also helps if you are a “squirter”. Anyhow, if you got one, hit him up! He’d best not wait by his mailbox for replies.
  • He’s 52, divorced, from Shrewsbury and has a sandbox he wants a woman to play in with him. Ladies, bring your plastic shovel and bucket!
  • This is strange: a man looking for a couple so the woman can watch while he deep throats her husband. All this plus he’s 58. He must be particular however as you must live in Worcester.
  • If you are a 23-year-old male virgin perhaps making your first sexual experience with a couple is not a bad way to get introduced to sex. It’s unclear what role if any the husband has in this other than as voyeur. Just in case the couple ad doesn’t work out he also has a more traditional ad.
  • He’s 46-years-old, a recent widower and actually from Rhode Island and needs a fuck buddy while presumably he works through his grief. Or maybe since he’s looking he’s beyond that stage. Anyhow, unlike most of these posters he looks like a normal guy, so hit him up, ladies.
  • There are lots of bad things that can happen in a casual encounter, but a lot that can be avoided. Here’s a gay 45-year-old man from Winchendon who wants you to bring a camera so you can join him in taking pictures of them naked. As I’ve noted before, testosterone makes men suggest crazy things and this is definitely one of them.
  • He’s 42 and from Webster and is looking for Jennifer Sherman so that he can peak at her through her window again. I do hope this was consensual last time. Any Jennifer Shermans in the Webster area should lie low for a while and if asked say it must have been that other Jennifer Sherman. Which brings up another unwritten rule for these encounters: if you are stupid enough to go through with them, never tell him your last name.
  • He’s young, from Worcester, has nice abs and wants to see you (a woman) gain weight. No, really!
  • She 27 and really likes dominant men, so much so that her dominant husband is not dominant enough. So hubby needs help from a second super dominant man to finally put her in her place.
  • In a similar vein, here’s a couple from Worcester looking for a gay or bi guy to join them because she gets off on seeing man on man, or at least a man enjoying her husband. That sounds fair given that so many men are into watching lesbians. The ultimate goal here is double penetration of the same orifice.

While few women are posting in Worcester, I am impressed by the weird postings mostly from men in Worcester, so it’s definitely worth a return visit.

More in April.

 

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