Craigslist Weirdo Of The Week – Tranny Bob

Kevin recently asked me to take over the craigslist personal ad feature and I greatly obliged. But before we begin, allow me to introduce myself.

The name is Jason Winder and I’m obsessed with the internet. I spend nearly ten hours a day on the net with only work and sleep to keep me from rounding out the other fourteen. My basis for reality is somewhat slipping as of late as a result of spending life online.

I compare it to the old HBO program, “Dream On” starring Brian Benben as a man who grew up watching so much television that, in adulthood, his concepts of relationships and human understanding were based solely on TV clips.

This is how I am right now with the Internet. As a consequence, I have learned to read people quite well and, hell, these weirdos are much more disturbed than I am and I like that.

When I showed Kevin some of my saved profiles, he vomited violently and after an awkward two days of silence, he called and begged me to take over craigslist duties. While holding my phone sandwiched between my ear and shoulder, penis in my right hand and camera in my left, I told him I would be delighted.

I sent him a picture of the scene to mark the occasion. He uses it as his desktop background.

So, in keeping within the boundaries of my own depravity, I will now take the chance to share some profiles. Where most others would scoff at these individuals, I extend my hand to them in respect.

Let’s begin with a man I’ve dubbed, “Tranny Bob”.

After all my searching, I have decided to bestow upon “Tranny Bob” the prestigious title of craigslist.org weirdo of the week. While I’m sure there are plenty of similar weirdos posting their sick selves online, the creepy look in his eyes just does it for me.

Tranny Bob actually posted two profiles this week but for the sake of keeping things a little less vulgar on this website, I am just featuring this one. His other profile includes two additional pictures which give his suitors a preview of what his cock and balls look like adorned in panties (hint: they don’t fit). I was eating at the time and had to stop.

Quick lesson: don’t eat while looking at craigslist personal ads.

Without really tearing this guy apart, as much as I would like to, I really want his simple sentence and “more-than-a-thousand-words” pictures to speak for themselves.

In his defense, he does look like a red-headed human version of Miss Piggy. And many people, like myself, found her to be a very sexy Muppet. So if you apply that logic to Tranny Bob then by all means, he is a hot Muppet.

Just look at those boobs and nice long legs. The caked-on makeup is kind of frightening but whatever makes him happy, makes me happy. Just as long as he doesn’t molest me on the playground.

I will not, at this point, further discuss his clothing PREFERENCE but rather his other hobby: camping while in drag. If you ask me, the two go hand in hand.

How awesome would it be if you came across this guy and his buddy frolicking in the woods while wearing women’s clothing? Not awesome at all, actually. It would be terrifying.

Picture this: A newly-married, god-fearing couple and their two young boys, both under the age of ten, go on their annual camping trip. Harmless fun, right? It is, until, while walking in the woods they come across these two, making out in high heels and holding onto each other’s fishing rods.

It would not be a pleasant scene. The dad could convince the youngest one that it was Bigfoot and the idiot would be believe him. The older one, on the other hand, would understand what’s going on and thereby lose faith in humanity, God and himself. Cut to ten years later and now he has a cross-dressing/camping fetish.

See, Tranny Bob thinks what he is doing is harmless – dressing up in drag, going camping with a buddy, doing the whole brokeback thing but he is really hurting America. People don’t need to see this. It ruined a family I just made up!

If Tranny Bob wants to go camping while in drag, he can set up a tent in his living-room, spark up the old fireplace, play some John Denver and finger-bang his fellow craigslist drag buddy.

I mean if I have to do it, then why shouldn’t he?

Just a thought.