I am off of work today, so if you comment and I don’t respond it is because I am failing miserably at this.

With that out of the way, it is time to talk about Will. As I said last week, this is a more “adult” story and many not be suitable for young ears. Or at work. So I’ll throw a quick NSFW on here and call it good.

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So the story begins about two years ago. I am driving on the turnpike with my wife and we have Will on the phone talking about when he is going to come back to Florida to visit. He tends to live half the year in Maine and half the year in Florida, and it was about time for him to come back.

Well we also started talking to him about his past “conquests” because generally we get some pretty funny info about Will’s love life out of asking. Today was the jackpot.

We start talking about his first time and he quickly informs me that his first sexual encounter was not the one I was led to believe. Then he realizes that I don’t know it, so he tries to hide the details. But being super proud of his 19-year old self, he starts to tell the story.

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His father has made a career out of buying, fixing and selling houses. He is quite good at it. So Will often gets tasked with odd jobs around the houses his father owns. One day he was shoveling snow off the driveway of one of the apartment buildings his father owns and a lady who was renting there came outside and started cat calling him. Like legit whistling and saying very sexual things. He just laughs it off and plays along.

A week later he is shoveling again, and sure enough out she comes to ogle him. He finally just turns to her and goes, “you want this... Prove it.”

So she opens her door and he goes inside. He is scared shitless at this point. He did not expect her to go through with it. Not one to back down, he sits on the couch and she proceeds to give him, in his own words “The best BJ I have ever had.”

At this point, I am actually almost proud of young Will. That was a ballsy move. Then he lets out a little bit more info. Turns out every week after that he would shovel her driveway and get his little “present” afterwards. Then he started going a couple of times a week.

And in a totally Will move, he even inquired to his father (who is divorced) if he has ever... you know... with that particular resident. His father says hell no.

The kicker here, Will is 19, the lady who he has been seeing turns out to be 45. Not terrible, she’s only just over twice his age. I’ve seen worse. THE REAL KICKER - she has dentures.

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Yes Will told us that she had dentures and the reason it was the best he ever had was because he would ask her to take them out. I am going to let that sink in for a second.

Anyway, it turns out this little “affair” went on for a couple of years. She finally broke it off, not because she wanted to stop, but for another reason. A very Will reason.

Thing is, she expected Will to hang out with her for a little bit (10 minutes or so) and talk to her after they were done each time. She enjoyed having the company. This was far too much for young Will. He had places to go, TV to go watch on his own.

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Will completely admits that he just didn’t want to talk to her. Not even for the best he ever had. And the best part was the last thing he told us about his 45-year old maiden.

“Yeah, she expected me to talk to her after. Who does that? I looked her up a little while back. Turns out she was just lonely.”

Will, crushing 45-year old women’s dreams since 2007.

This story later caused another friend of ours to look me dead in the eye and say, “Wow, you should write a book. The story of Will: It’s kind of like a bad porno.”

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Don’t forget to tune in next week, when the story will again be about our 45-year old maiden and Will. And next week’s story is one of my favorite Will stories of all time. It is the second best story I have about Will, in my opinion anyway. And everyone I ever tell it to can never look at Denny’s the same way.

Enjoy this photo by the way. It is the default young Will doosh photo we use for photoshopping. In fact, I encourage any and all photoshopping with this photo.


If you missed a week, I got you covered.