Boston UBER Confessions: The craziest stories from Boston’s best UBER driver



Boston’s Best UBER Driver has something to share….Buckle up, grab your popcorn and get ready for Boston’s 1st edition of UBER CONFESSIONS right here on WTP Sports.

After driving around Boston for 2 1/2 years on weekends for UBER paying the bills with 2 kids in college, one can assume I’d have some pretty good stories to tell. That simple answer is…Holy crap do I ever.

Picking up a lot of Boston’s college students can be quite the show let me tell you at 2am on a Friday or Saturday night. One weekend night I had the pleasure of picking up 2 very attractive gals who were extremely inebriated to say the least after a long night of partying at one of Boston’s finest drinking establishments.

 After the proverbial chit chat these 2 fine ladies commented ” you have the coolest UBER ride in Boston and the back seat of your Dodge Ram 1500 is big enough to have sex without having to get all twisted up like a pretzel”. So of course, kidding around I agreed with them and let them know that whatever happens in the UBER stays in the UBER just like you see on TV about those tourist commercials for Las Vegas.


So with a little nudge down the right path with 2 of Boston’s finest college students, I assured them and agreed of course that a big back seat and tinted windows it would be easy to “get busy” and nobody would even be able to tell. All I can say is…oh shit I was not expecting what happened next. 

Not only did they start making out (etc.), but it was the finest rug munching session worthy of a porn movie and could have been a nice pay day for them if they wanted to star in one.

 Don’t worry folks, I do get a nice detail inside and out on a weekly basis at one of Boston’s best car washes. But holy shit – I could have driven nails in a 2 x 4 piece of wood with my man hammer after watching that show if I wasn’t a happily married guy. 

The best part of this story is…I got the same 2 awesome chicks the very next weekend at the same bar at the same closing time and I got 2 big hugs and lots of giggles. I even got a Rated G video of them singing and dancing in my truck so you sicko’s lose out. Go to a porn site you crazy bastards. But I assure you if I pick them up a 3rd time I’m going to offer to be their manager, director and producer and we’ll all be rich damn it.


Anyone that is familiar with Boston neighborhoods knows that the area on Mass. Ave from the Back Bay train station all the way down to Boston City Hospital in the South End is nicknamed ” Methadone Mile” so you can only imagine who and what you can see as an UBER driver late at night in that area. Although I can’t lay claim to this story since it’s from an UBER driver buddy of mine (who will remain anonymous) who gave me this next story.  

As my buddy was waiting to pick up a rider in this area, what can next be described is simple. Methadone Mile ? Check ! 2am ? check ! Random drug induced lady of the evening jumping into an UBER ? check ! Random drug induced lady of the evening thinking she’s meeting a “John” ? check ! Then random drug induced lady of the evening starts unzipping his pants and starts fondling his staff as he holds back his laugh. He’s a married guy so he politely said “WHOA” I think you have me confused with someone else. She then apologizes and leaves his vehicle. Can’t make this stuff up – it really happens.


This next story is a classic. I’m heading to a Boston neighborhood at 3am to pick up “Peter”. It’s literally a downpour monsoon going on outside with the weather when all of a sudden a woman gets in the front seat. Puzzled I figured it was a girlfriend that hooked up with a guy at bar a little earlier and he was kind enough to call an UBER for her. NOPE !! It was another one of Boston’s ladies working in the worlds oldest profession after making her money. I set the destination which is 15 minutes away and she proceeds to tell me all about how “It’s her vagina and if she can make the cash – it’s her choice”.  Whatever. 

Then she proceeds to go into all sorted details about where all the Ho’s and Pimps hang out (Victoria’s Diner) in Boston late at night while they’re waiting for their phones to ring with drunk guys who couldn’t hook up at the bar with someone. After listening for a good 10 minutes to her life story and stopping at an all night gas station for cigarettes I’m then told I’m cute and do I have a girlfriend (Code for do I want to pay for sex). I figured I’d play along with her as we’re pulling up to what can be described as her pimps house in one of Boston’s finest neighborhoods NOT. So I respond “No I don’t have a girlfriend”. She then ask “Would you like one”. I replied “Yeah, I’d love a girlfriend but I have to ask my wife first”. 

Needless to say I went straight to that fine car wash in Boston in the morning and got a double detail for Boston’s Best UBER Ride.


You’re wondering why there’s a picture of Barney The Purple Dinosaur here on WTP Sports’ UBER Confessions of a Boston UBER driver. It’s how I get all the 5 star ratings folks. I can’t make this crap up but I tell all the millennial college students in Boston that one of my other jobs in life was one of the voices of Barney himself. I do sound like Barney – scary I know. You can’t make that up unless you can back it up !!!


Until next time. Enjoy these UBER CONFESSIONS of Boston’s Best UBER ride. I’m thinking of buying a dashboard GO-PRO to capture some of this stuff for next time. Who knows – maybe I’ll get my directorial debut if I pick up the hot carpet munchers again. God knows, I know where they like to get all liquored up hehe.





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